dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b746986bccd04349ac80aca4a1d8e6ff | COc1ccc2[nH]c3c(-c4ccccc4)cc4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1cc(-c1ccccc1)c1[nH]c3ccc(O)cc3c21 | COC1=CC=2C=3C4=C(C=C(C3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O.B(Br)(Br)Br>>OC1=CC=2C=3C4=C(C=C(C3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O | C[O:22][c:21]1[cH:20][cH:19][c:18]2[nH:17][c:16]3[c:9](-[c:10]4[cH:11][cH:12][cH:13][cH:14][cH:15]4)[cH:8][c:7]4[c:6]([c:25]3[c:24]2[cH:23]1)[C:4](=[O:5])[NH:3][C:2]4=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[cH:8][c:9](-[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[nH:17][c:18]3[cH:19][cH:20][c:21]([OH:... | COc1ccc2[nH]c3c(-c4ccccc4)cc4c(c3c2c1)C(=O)NC4=O | O=C1NC(=O)c2c1cc(-c1ccccc1)c1[nH]c3ccc(O)cc3c21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1cc(-c1ccccc1)c1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 89 | [{"value": 89.0, "product": "OC1=CC=2C=3C4=C(C=C(C3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of 820 prepared as described in example 419 with BBr3 using the procedure described in example 80 gave (821) (89%), mp 335–345° C. 1H NMR δ [(CD3)2SO] 11.50 (s, 1H), 11.10 (s, 1H), 9.26 (d, J=2.4 Hz, 1H), 8.30 (d, J=2.4 Hz, 1H), 7.77–7.75 (m, 2H), 7.65–7.61 (m, 3H), 7.56–7.52 (m, 1H), 7.46 (d, J=8.7 Hz, 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | Other | null | null | null | COc1ccc2[nH]c3c(-c4ccccc4)cc4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1cc(-c1ccccc1)c1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bee6cc81798b48a8bd4bd2aec5f1ffac | COc1ccc2[nH]c(C=O)cc2c1>>CCC(=O)c1cc2cc(OC)ccc2[nH]1 | COC=1C=C2C=C(NC2=CC1)C=O.C(C)[Mg]Br>>COC=1C=C2C=C(NC2=CC1)C(CC)=O | [CH:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[nH:15]1>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[nH:15]1 | COc1ccc2[nH]c(C=O)cc2c1 | CCC(=O)c1cc2cc(OC)ccc2[nH]1 | null | null | null | Miscellaneous | OtherReaction | c3182bd139a48ca70cd0f50d0a14037e192e16b1061c0b9712f88c98d2a5a24d | 400b634e76686fc7fad4b6c270f7adcc668a541586c918f6a2b1db4bcddf835a | c1ccc2[nH]ccc2c1 | [O;D1;H0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[C;D1;H3:7]-[C:8]-[C;H0;D3;+0:2](=[O;D1;H0:1])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 82 | [{"value": 82.0, "product": "COC=1C=C2C=C(NC2=CC1)C(CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-methoxy-1H-indole-2-carbaldehyde with ethylmagnesium bromide using the procedure described in example 404 gave (822) (82%), mp 170–171.5° C. 1H NMR δ [(CD3)2SO] 11.56 (s, 1H), 7.34 (d, J=9.1 Hz, 1H), 7.22 (d, J=1.7 Hz, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.93 (d, J=9.1, 2.4 Hz, 1H), 3.77 (s, 3H), 2.96 (q, J=7.3 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Ketone | null | null | c1ccc2[nH]ccc2c1 | Other | null | null | null | COc1ccc2[nH]c(C=O)cc2c1>>CCC(=O)c1cc2cc(OC)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c1675234c70240b48ae826e8c683167a | CCc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(OC)cc13)C(=O)NC2=O>>CCc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(O)cc13)C(=O)NC2=O | C(C)C1=C(C2=C(C=3C=4C=C(C=CC4NC13)OC)C(NC2=O)=O)C2=CC=CC=C2.B(Br)(Br)Br>>C(C)C1=C(C2=C(C=3C=4C=C(C=CC4NC13)O)C(NC2=O)=O)C2=CC=CC=C2 | C[O:20][c:19]1[cH:18][cH:17][c:16]2[nH:15][c:14]3[c:3]([CH2:2][CH3:1])[c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[c:11]4[c:12]([c:13]3[c:22]2[cH:21]1)[C:23](=[O:24])[NH:25][C:26]4=[O:27]>>[CH3:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[c:12]([c:13]3[c:14]1[nH:15][c:16]1[cH:17][cH:18][c:19](... | CCc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(OC)cc13)C(=O)NC2=O | CCc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(O)cc13)C(=O)NC2=O | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97 | [{"value": 97.0, "product": "C(C)C1=C(C2=C(C=3C=4C=C(C=CC4NC13)O)C(NC2=O)=O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of (825) prepared as described in example 423 with BBr3 using the procedure described in example 80 gave (826) (97%), mp 190–196° C. 1H NMR δ [(CD3)2SO] 11.63 (s, 1H), 10.81 (s, 1H), 9.21 (s, 1H), 8.31 (d, J=2.4 Hz, 1H), 7.48–7.40 (m, 4H), 7.31–7.29 (m, 2H), 7.06 (dd, J=8.7, 2.4 Hz, 1H), 2.74 (q, J=7.4 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | Other | null | null | null | CCc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(OC)cc13)C(=O)NC2=O>>CCc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(O)cc13)C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-79ef9e4d9baf47909d82b5c863d6a907 | COCCOc1ccccc1/C=C/c1cc2cc(OCc3ccccc3)ccc2[nH]1.O=C1C=CC(=O)N1>>COCCOc1ccccc1-c1cc2[nH]c3ccc(OCc4ccccc4)cc3c2c2c1C(=O)NC2=O | C(C1=CC=CC=C1)OC=1C=C2C=C(NC2=CC1)\C=C\C1=C(C=CC=C1)OCCOC.C1(C=CC(N1)=O)=O>>C(C1=CC=CC=C1)OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)OCCOC)C(NC4=O)=O | [CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1/[CH:12]=[CH:13]/[c:14]1[nH:15][c:16]2[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][c:29]2[cH:30]1.[CH:31]1=[CH:32][C:33](=[O:34])[NH:35][C:36]1=[O:37]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c... | COCCOc1ccccc1/C=C/c1cc2cc(OCc3ccccc3)ccc2[nH]1.O=C1C=CC(=O)N1 | COCCOc1ccccc1-c1cc2[nH]c3ccc(OCc4ccccc4)cc3c2c2c1C(=O)NC2=O | null | null | null | Functional Group Interconversion | OtherReaction | cd603450aa7a57e4b62436ecbb89ceeb2ed0f6bb962ef67f12fcd9fa5f0e9fd1 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OCc4ccccc4)cc3c21 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](/[CH;D2;+0:5]=[CH;D2;+0:6]/[c:7]1:[#7;a:8]:[c:9](:[c:10]):[c:11](:[c:12]):[cH;D2;+0:13]:1):[c:14]:[c:15].[O;D1;H0:16]=[C:17]1-[#7:18]-[C:19](=[O;D1;H0:20])-[CH;D2;+0:21]=[CH;D2;+0:22]-1>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]2:[#7;a:8]:[c:9](:[c:10]):... | 46 | [{"value": 46.0, "product": "C(C1=CC=CC=C1)OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)OCCOC)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of (852) with maleimide using the procedure described in method 4a gave the adduct (CIII; Ar=2-(2-methoxyethoxy)phenyl, R10═H (853), which was used without further purification. Aromatisation of (853) with MnO2 using the procedure described in example 79 gave (854) (46%) as an orange solid, mp 157–159° C., whi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | null | null | null | null | COCCOc1ccccc1/C=C/c1cc2cc(OCc3ccccc3)ccc2[nH]1.O=C1C=CC(=O)N1>>COCCOc1ccccc1-c1cc2[nH]c3ccc(OCc4ccccc4)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d994210277644129c424413fa4c52d0 | Br.COc1cc([N+](=O)[O-])ccc1CO.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | COC1=C(C=CC(=C1)[N+](=O)[O-])CO.Br.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].COC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)[N+](=O)[O-] | [BrH:32].O[CH2:12][c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10]1.[P:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10][c:11]1[CH2:12][P+:13](... | Br.COc1cc([N+](=O)[O-])ccc1CO.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | null | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bbb792e2dbaac6137f4ab4b2ad2edf8b90c54de5f7db3b319a5444b78b4405dc | 5700379a096deb40e2dc50b293f55a01cfe36aa58cf97bdfa006d0b7ff21038e | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[BrH;D0;+0:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:5].[c:3]:[c:2](-[CH2;D2;+0:1]-[P+;H0;D4:8](-[c:7](:[c:6]):[c:15])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:4] | 84 | [{"value": 84.0, "product": "[Br-].COC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | Bromination of (2-methoxy-4-nitrophenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, except that the conditions for the displacement were 3 days at 20° C. followed by 1 day at 55° C., gave the phosphonium salt (582... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | null | 72 | Br.COc1cc([N+](=O)[O-])ccc1CO.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1>COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8cb584bc0fb4a4fa0534eb7424f8082 | COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cc2cc(OCc3ccccc3)ccc2[nH]1>>COc1cc([N+](=O)[O-])ccc1/C=C/c1cc2cc(OCc3ccccc3)ccc2[nH]1 | [Li+].CC(C)[N-]C(C)C.C(C1=CC=CC=C1)OC=1C=C2C=C(NC2=CC1)C=O.[Br-].COC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)[N+](=O)[O-].[Li+].CC(C)[N-]C(C)C>>C(C1=CC=CC=C1)OC=1C=C2C=C(NC2=CC1)\C=C\C1=C(C=C(C=C1)[N+](=O)[O-])OC | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:12][c:11]2[c:3]([O:2][CH3:1])[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10]2)cc1.O=[CH:13][c:14]1[cH:15][c:16]2[cH:17][c:18]([O:19][CH2:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[cH:27][cH:28][c:29]2[nH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10][c:11]1... | COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cc2cc(OCc3ccccc3)ccc2[nH]1 | COc1cc([N+](=O)[O-])ccc1/C=C/c1cc2cc(OCc3ccccc3)ccc2[nH]1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C/c1cc2cc(OCc3ccccc3)ccc2[nH]1)\c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[c:6]:[c:7](-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]>>[c:6]:[c:7](/[CH;D2;+0:8]=[CH;D2;+0:1]/[c:2](:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | 5 | HOUR | The aldehyde (846) was reacted with (2-methoxy-4-nitrobenzyl) (triphenyl)phosphonium bromide (582) prepared as described in example 432 using the procedure described in method 2, except that the LDA and aldehyde were (sequentially) added at 0° C., the ratio of LDA;aldehyde was 1.5:1 and the reaction time was 5 h, to gi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | 5 | COc1cc([N+](=O)[O-])ccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cc2cc(OCc3ccccc3)ccc2[nH]1>>COc1cc([N+](=O)[O-])ccc1/C=C/c1cc2cc(OCc3ccccc3)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4168c7d6c6a6492c9e5012519517523b | COC(=O)C(Br)C(=O)OC.COc1cc(Br)c(O)c(C=O)c1>>COC(=O)c1cc2cc(OC)cc(Br)c2o1 | C([O-])([O-])=O.[K+].[K+].BrC=1C(=C(C=O)C=C(C1)OC)O.BrC(C(=O)OC)C(=O)OC>>BrC1=CC(=CC=2C=C(OC21)C(=O)OC)OC | COC(=O)[CH:5](Br)[C:3]([O:2][CH3:1])=[O:4].O=[CH:6][c:7]1[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([Br:14])[c:15]1[OH:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([Br:14])[c:15]2[o:16]1 | COC(=O)C(Br)C(=O)OC.COc1cc(Br)c(O)c(C=O)c1 | COC(=O)c1cc2cc(OC)cc(Br)c2o1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 32ded934f05d4f6cceec6913aa96d38e2eac1cec5795bb0d513cc400f5981804 | c735ca162108d7c1f879bd8345f950c882b35bd1ae1f5af6bd4a52a28e11b349 | c1ccc2occc2c1 | Br-[CH;D3;+0:1](-C(=O)-O-C)-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].O=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[cH;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:11]):[o;H0;D2;+0:10]:1 | 56 | [{"value": 56.0, "product": "BrC1=CC(=CC=2C=C(OC21)C(=O)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "BrC1=CC(=CC=2C=C(OC21)C(=O)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution containing 3-Bromo-2-hydroxy-5-methoxy-benzaldehyde (94.7 g, 0.410 mol) and dimethyl bromomalonate (103 g, 0.492 mol) in toluene (1.2 L) was added freshly powdered potassium carbonate (85 g, 0.615 mol) and tetra-n-butylammonium bromide (13.2 g, 0.041 mol). The reaction was heated at reflux under a Dean-St... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Ester.Ester.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2occc2c1 | c1ccc2occc2c1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | null | null | COC(=O)C(Br)C(=O)OC.COc1cc(Br)c(O)c(C=O)c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>COC(=O)c1cc2cc(OC)cc(Br)c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d80c8c706d54d52b27d08212a2f23ba | CCOP(=O)(Cc1ccccc1Cl)OCC.COc1cc(Br)c2oc(C=O)cc2c1>>COc1cc(Br)c2oc(/C=C/c3ccccc3Cl)cc2c1 | O.ClC1=C(CP(OCC)(OCC)=O)C=CC=C1.BrC1=CC(=CC=2C=C(OC21)C=O)OC.[H-].[Na+]>>BrC1=CC(=CC=2C=C(OC21)\C=C\C2=C(C=CC=C2)Cl)OC | CCOP(=O)(OCC)[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18].O=[CH:10][c:9]1[o:8][c:7]2[c:5]([Br:6])[cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]2[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[o:8][c:9](/[CH:10]=[CH:11]/[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[Cl:18])[cH:19][c:20]2[cH:21]1 | CCOP(=O)(Cc1ccccc1Cl)OCC.COc1cc(Br)c2oc(C=O)cc2c1 | COc1cc(Br)c2oc(/C=C/c3ccccc3Cl)cc2c1 | null | null | O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C/c1cc2ccccc2o1)\c1ccccc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[#8;a:8]:[c:9]>>[c:3]:[c:2](/[CH;D2;+0:1]=[CH;D2;+0:5]/[c:6](:[c:7]):[#8;a:8]:[c:9]):[c:4] | 84 | [{"value": 84.0, "product": "BrC1=CC(=CC=2C=C(OC21)\\C=C\\C2=C(C=CC=C2)Cl)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "BrC1=CC(=CC=2C=C(OC21)\\C=C\\C2=C(C=CC=C2)Cl)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of diethyl 2-chlorobenzylphosphonate (4.91 g, 0.018 mol) and 7-bromo-5-methoxybenzofuran-2-carbaldehyde (11.27 g, 0.016 mol) in tetrahydrofuran (80 mL) was added sodium hydride (60% dispersion in mineral oil, 0.74 g, 0.0185 mol). After 5 min. the reaction mixture was warmed to 60° C. for 1 h. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccc2occc2c1.c1ccccc1 | HO- | O1CCCC1 | 60 | null | CCOP(=O)(Cc1ccccc1Cl)OCC.COc1cc(Br)c2oc(C=O)cc2c1>O1CCCC1>COc1cc(Br)c2oc(/C=C/c3ccccc3Cl)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d8a90849f4246fb9111f17d245c4b45 | COc1cc(Br)c2oc(/C=C/c3ccccc3Cl)cc2c1.O=C1C=CC(=O)N1>>COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3 | BrC1=CC(=CC=2C=C(OC21)\C=C\C2=C(C=CC=C2)Cl)OC.C1(C=CC(N1)=O)=O.C1(C=CC(N1)=O)=O.[Sn](Cl)Cl.[Sn](Cl)Cl>>BrC1=CC(=CC2=C1OC1=C2C2C(NC(C2C(C1)C1=C(C=CC=C1)Cl)=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[o:8][c:9](/[CH:28]=[CH:20]/[c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[Cl:27])[cH:10][c:11]2[cH:12]1.[CH:13]1=[CH:19][C:17](=[O:18])[NH:16][C:14]1=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[o:8][c:9]3[c:10]([c:11]2[cH:12]1)[CH:13]1[C:14](=[O:15])[NH:16][C:17](=[O:18])... | COc1cc(Br)c2oc(/C=C/c3ccccc3Cl)cc2c1.O=C1C=CC(=O)N1 | COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3 | null | null | null | C-C Coupling | OtherReaction | 6dd5016b57052fef3431158cc9c5852a3a2b640ad9a8141262dfdadefdee73dd | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1NC(=O)C2C(c3ccccc3)Cc3oc4ccccc4c3C12 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1.[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11](/[CH;D2;+0:12]=[CH;D2;+0:13]/[c:14](:[c:15]):[c:16]):[#8;a:17]:[c:18]:1:[c:19]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[CH;D3;+0:7]-1-[c;H0;D3;+0:10]1:[c:9](:[c:8]):[c:18](:[c:19]):[#8;a:17]:... | null | [] | 150 | CELSIUS | null | null | A solution of (859) (4.89 g, 0.0185 mol) prepared as described in example 441, maleimide (1.44 g, 0.02 mol) and tin(II) chloride (2.8 g, 0.02 mol) in xylenes (40 mL) was heated to 150° C. overnight. After the addition of more maleimide (1.44 g, 0.02 mol) and tin(II) chloride (1.44 g, 0.01 mol) the reaction was again he... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2occc2c1.C1=CCNC1 | c1ccc2c3c(oc2c1)CCC1CNCC31 | c1ccccc1.c1ccc2c3c(oc2c1)CCC1CNCC31 | null | null | 150 | null | COc1cc(Br)c2oc(/C=C/c3ccccc3Cl)cc2c1.O=C1C=CC(=O)N1>>COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6037c376f6cf4a77b61b13054950d1d6 | COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3>>COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | BrC1=CC(=CC2=C1OC1=C2C2C(NC(C2C(C1)C1=C(C=CC=C1)Cl)=O)=O)OC>>BrC1=CC(=CC2=C1OC1=C2C=2C(NC(C2C(=C1)C1=C(C=CC=C1)Cl)=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[o:8][c:9]3[c:21]([c:22]2[cH:23]1)[CH:20]1[CH:19]([CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[CH2:10]3)[C:27](=[O:28])[NH:26][C:24]1=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[o:8][c:9]3[cH:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[Cl:18])[c... | COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3 | COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | null | O=[Mn]=O | null | Oxidation | OtherReaction | cf97701b58d36476a23845a75084dcd5a05d075528976394b21eb25d2adaa107 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1oc3ccccc3c21 | [Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7]2:[#8;a:8]:[c:9]:[c:10]:[c:11]:2-[CH;D3;+0:12]2-[C:13](=[O;D1;H0:14])-[#7:15]-[C:16](=[O;D1;H0:17])-[CH;D3;+0:18]-1-2):[c:19]:[c:20]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]2:[#8;a:8]:[c:9]:[c:10]:[c:11]:2:... | 67 | [{"value": 67.0, "product": "BrC1=CC(=CC2=C1OC1=C2C=2C(NC(C2C(=C1)C1=C(C=CC=C1)Cl)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Aromatisation of (860) prepared as described in example442 with MnO2 using the procedure described in example 79 gave the dibenzofuran (861) as a yellow solid (67%). 1H NMR δ [(CD3)2SO] 8.22 (d, J=2.6 Hz, 1H), 8.14 (s, 1H), 7.62 (m, 2H), 7.48 (m, 3H), 3.98 (s, 3H). MH−:458,457,456,454.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c(oc2c1)CCC1CNCC31 | c1ccc2c(c1)oc1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)oc1ccc3c(c12)CNC3 | null | O=[Mn]=O | null | null | COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3>O=[Mn]=O>COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-792bed4399df4e62adb87dcc88912b45 | COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1oc3c(Br)cc(O)cc3c21 | BrC1=CC(=CC2=C1OC1=C2C=2C(NC(C2C(=C1)C1=C(C=CC=C1)Cl)=O)=O)OC.B(Br)(Br)Br>>BrC1=CC(=CC2=C1OC1=C2C=2C(NC(C2C(=C1)C1=C(C=CC=C1)Cl)=O)=O)O | C[O:24][c:23]1[cH:22][c:20]([Br:21])[c:19]2[o:18][c:17]3[cH:16][c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[Cl:15])[c:7]4[c:6]([c:27]3[c:26]2[cH:25]1)[C:4](=[O:5])[NH:3][C:2]4=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15])[cH:16][c:17]1[o:18][c:19]3[c:20](... | COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1oc3c(Br)cc(O)cc3c21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1oc3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "BrC1=CC(=CC2=C1OC1=C2C=2C(NC(C2C(=C1)C1=C(C=CC=C1)Cl)=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of (861) prepared as described in example 442 with BBr3 using the procedure described in example 80 gave (862) (98%) which was used without further purification. 1H NMR δ [(CD3)2SO] 8.04 (d, J=2.3 Hz, 1H), 7.91 (s, 1H), 7.56 (d, J=8 Hz, 1H), 7.45 (m, 3H), 7.2 (d, J=2.5 Hz, 1H). MH−:443.9, 441.9, 439.9.
Co... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)oc1ccc3c(c12)CNC3 | Other | null | null | null | COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1oc3c(Br)cc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38c5ff3602ab40bb85dea69ba1ea2eba | CCCC[C]([Sn])=C(CCCC)CCCC.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1oc3c(Br)cc(O)cc3c21>>C=Cc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | BrC1=CC(=CC2=C1OC1=C2C=2C(NC(C2C(=C1)C1=C(C=CC=C1)Cl)=O)=O)O.C(CCC)C(=C(CCCC)CCCC)[Sn]>>ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C(=CC(=C1)O)C=C | CCCC[C]([Sn])=[C:2](CCCC)[CH2:1]CCC.Br[c:3]1[cH:4][c:5]([OH:6])[cH:7][c:8]2[c:9]1[o:10][c:11]1[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[Cl:20])[c:21]3[c:22]([c:23]21)[C:24](=[O:25])[NH:26][C:27]3=[O:28]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[cH:7][c:8]2[c:9]1[o:10][c:11]1[cH:12][c:13](-[c:14]3[cH:15][... | CCCC[C]([Sn])=C(CCCC)CCCC.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1oc3c(Br)cc(O)cc3c21 | C=Cc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | null | null | C-C Coupling | OtherReaction | 9fb2ff1933202b4914d3a6a42be05ae45f2692c6f8f5da684224fa04f8169f25 | 27ac22ec7469bd7f39cc3c50746346e388051103704091d8380f391d425a4ebf | O=C1NC(=O)c2c1c(-c1ccccc1)cc1oc3ccccc3c21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7].C-C-C-C-[C;H0;D3;+0:8](-[CH2;D2;+0:9]-C-C-C)=[C](-[Sn])-C-C-C-C>>[CH2;D1;+0:9]=[CH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7] | 79 | [{"value": 79.0, "product": "ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C(=CC(=C1)O)C=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of (862) prepared as described in example 443 with tributylvinyltin using the procedure described in example 309 gave (863) (79%). 1H NMR δ [(CD3)2SO] 9.80 (s, 1H), 8.04 (d, J=2.7 Hz, 1H), 7.91 (s, 1H), 7.56 (d, J=8 Hz, 1H), 7.45 (m, 3H), 7.2 (d, J=2.5 Hz, 1H), 6.96 (dd, J=18,1 Hz, 1H), 6.25 (d, J=18 Hz, 1H), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Vinyl | c1ccc2c(c1)oc1ccc3c(c12)CNC3 | c1ccc2c(c1)oc1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)oc1ccc3c(c12)CNC3 | HBr.Sn | null | null | null | CCCC[C]([Sn])=C(CCCC)CCCC.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1oc3c(Br)cc(O)cc3c21>>C=Cc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62cae9a2d35848e7979fc9f2cc564996 | C=Cc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>>CCc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C(=CC(=C1)O)C=C.CO.[H][H]>>ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C(=CC(=C1)O)CC | [CH2:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[cH:7][c:8]2[c:9]1[o:10][c:11]1[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[Cl:20])[c:21]3[c:22]([c:23]21)[C:24](=[O:25])[NH:26][C:27]3=[O:28]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([OH:6])[cH:7][c:8]2[c:9]1[o:10][c:11]1[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][c:1... | C=Cc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | CCc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | [Ni] | O1CCCC1 | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1oc3ccccc3c21 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5](:[c:6]):[#8;a:7]:[c:8]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](:[c:6]):[#8;a:7]:[c:8] | 59 | [{"value": 59.0, "product": "ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C(=CC(=C1)O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.9, "product": "ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C(=CC(=C1)O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (863) (0.054 g, 0.167 mmol) prepared as described in example 444 in a methanol:tetrahydrofuran mixture (1:1, 4 mL) was hydrogenated over Raney nickel (100 mg) and hydrogen. The product was purified by column chromatography using a gradient of 0–100% ethyl acetate in dichloromethane to give (864) (0.032 g,... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccc2c(c1)oc1ccc3c(c12)CNC3 | null | [Ni].O1CCCC1 | null | null | C=Cc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>[Ni].O1CCCC1>CCc1cc(O)cc2c1oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbb86781c71a49fe91ef221d735a96d5 | CCOC(C)=O.O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(O)cc3c21.O=P(Cl)(Cl)Cl.OCc1ccccc1>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(OCc4ccccc4)OCc4ccccc4)cc3c21 | C(C1=CC=CC=C1)O.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O.P(=O)(Cl)(Cl)Cl.C(C)(=O)OCC.P(=O)(Cl)(Cl)Cl>>P(=O)(OCC1=CC=CC=C1)(OCC1=CC=CC=C1)OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O | O=[C:34]([O:33][CH2:40][CH3:39])[CH3:36].[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[cH:15][c:16]1[nH:17][c:18]3[cH:19][cH:20][c:21]([OH:22])[cH:41][c:42]3[c:43]21.Cl[P:23](Cl)(Cl)=[O:24].[OH:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[O:1]=[C:2]1[NH:3][C:4... | CCOC(C)=O.O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(O)cc3c21.O=P(Cl)(Cl)Cl.OCc1ccccc1 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(OCc4ccccc4)OCc4ccccc4)cc3c21 | null | null | Cl.N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 3564037784ef5adcbf4996ababa00184a6ac0ce1ac23150c586eabd6d65739ee | aaaabb170071aca3e9fd224388668bb2934e6895454ffea304179cbd1d4ecf81 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(OCc4ccccc4)OCc4ccccc4)cc3c21 | Cl-[P;H0;D4;+0:1](-Cl)(-Cl)=[O;D1;H0:2].O=[C;H0;D3;+0:3](-[CH3;D1;+0:4])-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7].[OH;D1;+0:8]-[C:9]-[c:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[P;H0;D4;+0:1](-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14])(-[O;H0;D2;+0:8]-[C:9]-[c:10])-[O;H0;D2;+0:5]-[CH2;D2;+0:3]-[c:15]1:[cH;D... | 32 | [{"value": 32.0, "product": "P(=O)(OCC1=CC=CC=C1)(OCC1=CC=CC=C1)OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (I; Ar=phenyl) (0.50 g, 1.52 mmol) in pyridine (30 mL) under nitrogen was added phosphorous oxychloride (140 □L, 1.52 mmol) dropwise. After 40 minutes stirring at room temperature a further portion of phosphorous oxychloride (40 □L) was added a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Aromatic alcohol | null | null | c1ccccc1 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3.c1ccccc1.c1ccccc1 | HCl | Cl.N1=CC=CC=C1 | null | 0.333333 | CCOC(C)=O.O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(O)cc3c21.O=P(Cl)(Cl)Cl.OCc1ccccc1>Cl.N1=CC=CC=C1>O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(OCc4ccccc4)OCc4ccccc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50297983814043f68e5ed0382c170795 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(OCc4ccccc4)OCc4ccccc4)cc3c21>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(O)O)cc3c21 | P(=O)(OCC1=CC=CC=C1)(OCC1=CC=CC=C1)OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O>>P(=O)(OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O)(O)O | c1ccc(C[O:25][P:23]([O:22][c:21]2[cH:20][cH:19][c:18]3[nH:17][c:16]4[cH:15][c:8](-[c:9]5[cH:10][cH:11][cH:12][cH:13][cH:14]5)[c:7]5[c:6]([c:29]4[c:28]3[cH:27]2)[C:4](=[O:5])[NH:3][C:2]5=[O:1])(=[O:24])[O:26]Cc2ccccc2)cc1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[cH:1... | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(OCc4ccccc4)OCc4ccccc4)cc3c21 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(O)O)cc3c21 | null | [Pd] | CO.O1CCCC1 | Deprotection | OtherReaction | c42b4ea08bf8d136f49f4998ca3ab0462c7f6d385e485a4db39263d266e16e35 | ecac314cca8b931f5bfebb391dc97e333d1eca60b386dbe5c9a60f4d76cdb838 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | [#8:1]-[#15:2](=[O;D1;H0:3])(-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1)-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[#8:1]-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:4])-[OH;D1;+0:5] | 71 | [{"value": 71.0, "product": "P(=O)(OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O)(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "P(=O)(OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O)(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of the dibenzyl phosphate (336) (100 mg, 0.17 mmol) prepared as described in example 447 in methanol/tetrahydrofuran (3:1, 70 mL) was hydrogenated at 60 psi over Pd-C (5%, catalytic) with stirring for 3 hours. The reaction mixture was then filtered through celite and concentrated in vacuo. Trituration from e... | 10.6084/m9.figshare.5104873.v1 | null | null | Phosphate ester | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | Other | [Pd].CO.O1CCCC1 | null | 3 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(OCc4ccccc4)OCc4ccccc4)cc3c21>[Pd].CO.O1CCCC1>O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccc(OP(=O)(O)O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff6f51d07f50479399583ee3c6d0baf6 | CCOC(C)=O.COc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2C(C)=O)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC.C([O-])(O)=O.[K+].C(C)(=O)OCC>>C(C)(=O)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)OC | CCO[C:23]([CH3:24])=[O:25].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]1[nH:22]2)[C:26](=[O:27])[NH:28][C:29]3=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:1... | CCOC(C)=O.COc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2C(C)=O)C(=O)NC3=O | null | Cl(=O)(=O)(=O)O | C(C)(=O)OC(C)=O | Acylation | Ester with secondary amine to amide | 688ef3ba587db9845836f6f39d0d689534634b0b181724fb8b57c1ecd30f2b8a | 0753fc31027d62a96c7ff310f5ec44d489d03b7b6f621c1f23d0138c4910340d | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]1:[c:6]:[c:7]:[c:8](:[c:9]):[nH;D2;+0:10]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[n;H0;D3;+0:10]1:[c:5](:[c:4]):[c:6]:[c:7]:[c:8]:1:[c:9] | 80 | [{"value": 80.0, "product": "C(C)(=O)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of carbazole (33) (45 mg, 0.12 mmol) prepared as described in example 79 in acetic anhydride (4.0 mL) was added 35% perchloric acid (2 drops). The resulting solution was stirred at room temperature for 30 minutes before being poured onto ice water, basified by the addition of solid potassium bicarbonate a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | HO- | Cl(=O)(=O)(=O)O.C(C)(=O)OC(C)=O | null | 0.5 | CCOC(C)=O.COc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>Cl(=O)(=O)(=O)O.C(C)(=O)OC(C)=O>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2C(C)=O)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-afddef511fda484ca8479efad51022a6 | CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2[nH]1>>O=[N+]([O-])c1ccc2[nH]c(CO)cc2c1 | [BH4-].[Na+].C(=O)(N1C=NC=C1)N1C=NC=C1.[N+](=O)([O-])C=1C=C2C=C(NC2=CC1)C(=O)OCC.[OH-].[K+]>>[N+](=O)([O-])C=1C=C2C=C(NC2=CC1)CO | CCO[C:10]([c:9]1[nH:8][c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:14][c:13]2[cH:12]1)=[O:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9]([CH2:10][OH:11])[cH:12][c:13]2[cH:14]1 | CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2[nH]1 | O=[N+]([O-])c1ccc2[nH]c(CO)cc2c1 | null | null | CO.O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2[nH]ccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 40 | MINUTE | To a solution of ethyl 5-nitro-1H-indole-2-carboxylate (9.8 g, 42.0 mmol) in methanol (300 mL) was added a solution of 2 M potassium hydroxide (31 mL, 63.0 mmol). The reaction mixture was heated at reflux for 2 h and then the hot solution was filtered, poured onto ice, and acidified. The resultant fine pale brown preci... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2[nH]ccc2c1 | HO- | CO.O | null | 0.666667 | CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2[nH]1>CO.O>O=[N+]([O-])c1ccc2[nH]c(CO)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-820acf7a65ad4819a1d9f74c3a84cfc8 | O=[N+]([O-])c1ccc2[nH]c(CO)cc2c1>>O=Cc1cc2cc([N+](=O)[O-])ccc2[nH]1 | [N+](=O)([O-])C=1C=C2C=C(NC2=CC1)CO>>[N+](=O)([O-])C=1C=C2C=C(NC2=CC1)C=O | [OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]2[nH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]2[nH:14]1 | O=[N+]([O-])c1ccc2[nH]c(CO)cc2c1 | O=Cc1cc2cc([N+](=O)[O-])ccc2[nH]1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2[nH]ccc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 57.4 | [{"value": 57.0, "product": "[N+](=O)([O-])C=1C=C2C=C(NC2=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "[N+](=O)([O-])C=1C=C2C=C(NC2=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of crude (5-nitro-1H-indol-2-yl)methanol (3.60 g, 18.7 mmol) in chloroform (200 mL) was heated at 50° C. with manganese dioxide (20 g, 0.23 mol) for 3 h. The reaction mixture was then filtered through Celite and concentrated to give 5-nitro-1H-indole-2-carbaldehyde (904) (2.04 g, 57% through two steps). 1H N... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2[nH]ccc2c1 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | O=[N+]([O-])c1ccc2[nH]c(CO)cc2c1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>O=Cc1cc2cc([N+](=O)[O-])ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e267445cc72d435f96613a64bd3211d4 | Clc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cc2cc([N+](=O)[O-])ccc2[nH]1>>O=[N+]([O-])c1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1 | [N+](=O)([O-])C=1C=C2C=C(NC2=CC1)C=O.[Cl-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1>>ClC1=C(C=CC=C1)C=CC=1NC2=CC=C(C=C2C1)[N+](=O)[O-] | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])cc1.O=[CH:10][c:9]1[nH:8][c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][c:20]2[cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9]([CH:10]=[CH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[Cl:18])[cH:19][c:20]2[cH... | Clc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cc2cc([N+](=O)[O-])ccc2[nH]1 | O=[N+]([O-])c1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1cc2ccccc2[nH]1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[c:6]:[c:7](-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]>>[c:6]:[c:7](-[CH;D2;+0:8]=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | Reaction of the aldehyde (904) prepared as described in example 454 with 2-chlorobenzyltriphenylphosphonium chloride using the procedure described in example 37(at room temperature) gave the diene (905) as a mixture of E/Z isomers as a yellow solid (95%). Crystallisation from aqueous methanol yielded the pure E-isomer ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | Clc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cc2cc([N+](=O)[O-])ccc2[nH]1>>O=[N+]([O-])c1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99082dca256848d8960916f5a3b9bcd8 | O=C1C=CC(=O)N1.O=[N+]([O-])c1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>>O=C1NC(=O)C2C(c3ccccc3Cl)Cc3[nH]c4ccc([N+](=O)[O-])cc4c3C12 | ClC1=C(C=CC=C1)C=CC=1NC2=CC=C(C=C2C1)[N+](=O)[O-].C1(C=CC(N1)=O)=O>>ClC1=C(C=CC=C1)C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)[N+](=O)[O-] | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]=[CH:28]1.[CH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14])=[CH:15][c:16]1[nH:17][c:18]2[cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][c:26]2[cH:27]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH:6]2[CH:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[Cl:14])[CH2:15][c:16]3[nH:17][c:18... | O=C1C=CC(=O)N1.O=[N+]([O-])c1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1 | O=C1NC(=O)C2C(c3ccccc3Cl)Cc3[nH]c4ccc([N+](=O)[O-])cc4c3C12 | null | null | null | C-C Coupling | OtherReaction | dae1f4ad01a61f64ca47d979a23d024f40c181c790ce9b938fc44c63223a6fc0 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1NC(=O)C2C(c3ccccc3)Cc3[nH]c4ccccc4c3C12 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1.[c:8]:[c:9](-[CH;D2;+0:10]=[CH;D2;+0:11]-[c:12]1:[#7;a:13]:[c:14](:[c:15]):[c:16](:[c:17]):[cH;D2;+0:18]:1):[c:19]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[CH;D3;+0:7]-1-[c;H0;D3;+0:18]1:[c:12](:[#7;a:13]:[c:14](:[c:15]):[c:1... | 74 | [{"value": 74.0, "product": "ClC1=C(C=CC=C1)C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of the diene (905) prepared as described in example 455 with maleimide using the procedure described in example 68 gave the adduct (917) (74%) as a dark solid which was immediately aromatised.
Conditions: See reaction.notes.procedure_details.
Workup: prepared | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCNC1.c1ccc2[nH]ccc2c1 | c1ccc2c3c(nc2c1)CCC1CNCC31 | c1ccccc1.c1ccc2c3c(nc2c1)CCC1CNCC31 | null | null | null | null | O=C1C=CC(=O)N1.O=[N+]([O-])c1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>>O=C1NC(=O)C2C(c3ccccc3Cl)Cc3[nH]c4ccc([N+](=O)[O-])cc4c3C12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17b7dca0d68344b3a6052000b5c2298a | Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O.O=CO>>O=CNc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | NC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O.C(=O)O>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9]3[cH:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[Cl:18])[c:19]4[c:20]([c:21]3[c:22]2[cH:23]1)[C:24](=[O:25])[NH:26][C:27]4=[O:28].O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9]3[cH:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[Cl:18])[c:1... | Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O.O=CO | O=CNc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 54 | [{"value": 54.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Amine (919) prepared as described in example 467 and formic acid were reacted using the procedure described in example 468 with a reaction time of 4 h to give the formamide (921) (54%) as a yellow powder, mp 293–297° C. 1H NMR δ [(CD3)2SO] 12.11 (s, 0.5H), 12.08 (s, 1H), 11.12 (s, 0.5H), 11.08 (s, 1H), 10.34 (s, 1H), 1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HO- | null | null | null | Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O.O=CO>>O=CNc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f9bd3b0dcd2418e9894710a2a8be279 | CC(=O)O.Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>>CC(=O)Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | NC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O.C(C)(=O)O>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC(C)=O | O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[nH:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[c:20]4[c:21]([c:22]3[c:23]2[cH:24]1)[C:25](=[O:26])[NH:27][C:28]4=[O:29]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[nH:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][... | CC(=O)O.Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | CC(=O)Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 43 | [{"value": 43.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Amine (919) prepared as described in example 467 and acetic acid were reacted using the procedure described in example 468 with a reaction time of 4 h to give the acetamide (926) (43%) as a yellow powder, mp 240–245° C. 1H NMR δ [(CD3)2SO] 12.04 (br s, 1H), 11.07 (br s, 1H), 10.10 (s, 1H), 8.95 (d, J=2.1 Hz, 1H), 7.90 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HO- | null | null | null | CC(=O)O.Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>>CC(=O)Nc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f54c01cc7bf4ef68d7dd7fbd24d551f | Cn1c2ccc(NC=O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>CNc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2C)C(=O)NC3=O | COB(OC)OC.ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC=O)C.O1CCCC1>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC)C | O=[CH:1][NH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]1[n:22]2[CH3:23])[C:24](=[O:25])[NH:26][C:27]3=[O:28]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[... | Cn1c2ccc(NC=O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | CNc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2C)C(=O)NC3=O | null | null | CO | Reduction | OtherReaction | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | O=[CH;D2;+0:1]-[#7:2]-[c:3]>>[CH3;D1;+0:1]-[#7:2]-[c:3] | 52.3 | [{"value": 45.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.3, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)NC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Borane methylsulphide complex (0.074 mL, 0.78 mmol) and trimethylborate (0.089 mL, 0.78 mmol) were added at 0° C. under an atmosphere of nitrogen to a solution of amide (920) (0.105 g, 0.26 mmol) prepared as described in example 469 dry tetrahydrofuran (10 mL) After stirring at 0° C. for 30 min. the solution was allowe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | CO | 0 | 0.5 | Cn1c2ccc(NC=O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>CO>CNc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2C)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14e0c74bf2f440979f708a0c4bc3f41a | C[CH2][Sn]([CH2]C)([CH2]C)[CH2]C.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1[nH]c3ccc(OS(=O)(=O)C(F)(F)F)cc3c21>>C=Cc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | C(C)[Sn](CC)(CC)CC.FC(S(=O)(=O)OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)(F)F.[SnH4]>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)C=C | C[CH2][Sn]([CH2]C)([CH2]C)[CH2:2][CH3:1].O=S(=O)(O[c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][c:10](-[c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[Cl:17])[c:18]4[c:19]([c:20]3[c:21]2[cH:22]1)[C:23](=[O:24])[NH:25][C:26]4=[O:27])C(F)(F)F>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][c:10](-[c:11]4[cH:12][cH:13][... | C[CH2][Sn]([CH2]C)([CH2]C)[CH2]C.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1[nH]c3ccc(OS(=O)(=O)C(F)(F)F)cc3c21 | C=Cc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | null | null | null | C-C Coupling | OtherReaction | 563448ba3dce6bf7ee76e851eefce3dc8fcc2af1197d0cfee20ac388b61d7e61 | d5293e19f461de14317f6ded2c6505389fa55e397efa2e2b882f6761246e9ba3 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[CH2]-[Sn](-[CH2;D2;+0:1]-[CH3;D1;+0:2])(-[CH2]-C)-[CH2]-C.F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6](:[#7;a:7]):[c:8]:[c:9]:1>>[#7;a:7]:[c:6]1:[c:5]:[c:4]:[c;H0;D3;+0:3](-[CH;D2;+0:1]=[CH2;D1;+0:2]):[c:9]:[c:8]:1 | null | [] | null | null | null | null | Compound (616) was prepared from (615) prepared as described in example 479 (using the procedure described in example 309, with tetraethyl tin as the stannane to give a yellow oil. 1H NMR δ [(CD3)2SO] 11.71 (s, 1H), 11.48 (br, 1H), 8.23 (s, 1H), 8.78, (s, 1H), 7.99 (s, 1H), 7.62–7.43 (m, 5H), 7.2–7.1 (m, 1H), 6.10 (d, ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Tin | Vinyl | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | TfOH.HO-.Sn | null | null | null | C[CH2][Sn]([CH2]C)([CH2]C)[CH2]C.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1[nH]c3ccc(OS(=O)(=O)C(F)(F)F)cc3c21>>C=Cc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a88dd9b299e453abb8cca072f727e81 | CCOC(=O)CC(C)=O.N#CCC(N)=O>>Cc1c(O)cnc(O)c1C#N | P(=O)(Cl)(Cl)Cl.C(C)OC(CC(=O)C)=O.C(#N)CC(=O)N>>C(#N)C=1C(=NC=C(C1C)O)O | CCO[C:3](=[O:4])[CH2:5][C:2](=O)[CH3:1].[NH2:6][C:7](=[O:8])[CH2:9][C:10]#[N:11]>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][n:6][c:7]([OH:8])[c:9]1[C:10]#[N:11] | CCOC(=O)CC(C)=O.N#CCC(N)=O | Cc1c(O)cnc(O)c1C#N | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 58b19fd52453da574bcc3b76afc6cd3a75f4a5fd06fe35b2b231201f803400a4 | 214869d8c56cfda39a214771e48594e4871d6b04186a4be6361daff7202048a2 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C;D1;H3:5].[N;D1;H0:6]#[C:7]-[CH2;D2;+0:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[O;H0;D1;+0:11]>>[C;D1;H3:5]-[c;H0;D3;+0:4]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[cH;D2;+0:3]:[n;H0;D2;+0:10]:[c;H0;D3;+0:9](-[OH;D1;+0:11]):[c;H0;D3;+0:8]:1-[C:7]#[N;D1;H0:6] | null | [] | null | null | null | null | Amine was generated by the condensation of ethylacetoacetate with cyanoacetamide followed by reaction with phosphorus oxychloride to provide 3-cyano-2,5-dihydroxy-4-methylpyridine. Hydrogenation with palladium dichloride gave the 3-cyano-4-methylpyridine which was hydrogenated with Raney nickel in ammonia and ethanol t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amide | Aromatic alcohol.Aromatic alcohol | null | c1ccncc1 | c1ccncc1 | HO- | null | null | null | CCOC(=O)CC(C)=O.N#CCC(N)=O>>Cc1c(O)cnc(O)c1C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f95d46d5137142fabbbcce6cfc995bcd | CC(C)(C)OC(=O)N1CSC(C)(C)[C@H]1C(=O)O.N[C@@H]1C=CCCC1.O=P(Cl)(Oc1ccccc1)Oc1ccccc1>>CC1(C)SCN[C@@H]1C(=O)NCCCl | CS(=O)(=O)O.C(C)(C)(C)OC(=O)N1CSC([C@H]1C(=O)O)(C)C.[C@H]1(C=CCCC1)N.P(=O)(OC1=CC=CC=C1)(OC1=CC=CC=C1)Cl>>ClCCNC(=O)[C@H]1NCSC1(C)C | CC(C)(C)OC(=O)[N:6]1[CH2:5][S:4][C:2]([CH3:1])([CH3:3])[C@H:7]1[C:8](O)=[O:9].C1=C[C@@H:11]([NH2:10])[CH2:12]CC1.O=P(Oc1ccccc1)(Oc1ccccc1)[Cl:13]>>[CH3:1][C:2]1([CH3:3])[S:4][CH2:5][NH:6][C@@H:7]1[C:8](=[O:9])[NH:10][CH2:11][CH2:12][Cl:13] | CC(C)(C)OC(=O)N1CSC(C)(C)[C@H]1C(=O)O.N[C@@H]1C=CCCC1.O=P(Cl)(Oc1ccccc1)Oc1ccccc1 | CC1(C)SCN[C@@H]1C(=O)NCCCl | null | null | CCOC(=O)C | Acylation | OtherReaction | 20b524a36952aefc73436c067736891209bafaeae608c4aac1e40bdb4249cf6f | 8bc59b97eefa535f9a111bcf04a164db67aad44309b592bb9dfaaf6d468a6f72 | C1CSCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[#16:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].O=P(-[Cl;H0;D1;+0:8])(-O-c1:c:c:c:c:c:1)-O-c1:c:c:c:c:c:1.[NH2;D1;+0:9]-[C@@H;D3;+0:10]1-C=C-C-C-[CH2;D2;+0:11]-1>>[Cl;H0;D1;+0:8]-[CH2;D2;+0:11]-[CH2;D2;+0:10]-[NH;D2;+0:9]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[#16:3]-[... | null | [] | 0 | CELSIUS | 1 | HOUR | The title compound was prepared as follows. (R)-5,5-Dimethyl-thiazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 1 (1.95 g, 7.47 mmol) was dissolved in EtOAc (25 mL) and cooled to 0° C. Diphenyl chlorophosphate (1.71 mL, 8.23 mmol) was added followed by TEA (1.14 mL, 8.23 mmol). The reaction was stirred at 0° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Primary halide.Secondary amide.Secondary amine | C1CSC[NH]1.C1=CCCCC1.c1ccccc1.c1ccccc1 | C1CSCN1 | C1CSCN1 | HO- | CCOC(=O)C | 0 | 1 | CC(C)(C)OC(=O)N1CSC(C)(C)[C@H]1C(=O)O.N[C@@H]1C=CCCC1.O=P(Cl)(Oc1ccccc1)Oc1ccccc1>CCOC(=O)C>CC1(C)SCN[C@@H]1C(=O)NCCCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b6d776091c04501be0f6521d969c849 | COC(=O)[C@H]1N(C(=O)OC(C)(C)C)CC(F)(F)C1(C)C>>CC(C)(C)OC(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)O | COC([C@H]1N(CC(C1(C)C)(F)F)C(=O)OC(C)(C)C)=O.[Li+].[OH-]>>FC1(C([C@H](N(C1)C(=O)OC(C)(C)C)C(=O)O)(C)C)F | C[O:19][C:17]([C@H:16]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]([F:11])([F:12])[C:13]1([CH3:14])[CH3:15])=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C:10]([F:11])([F:12])[C:13]([CH3:14])([CH3:15])[C@H:16]1[C:17](=[O:18])[OH:19] | COC(=O)[C@H]1N(C(=O)OC(C)(C)C)CC(F)(F)C1(C)C | CC(C)(C)OC(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)O | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CCNC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 50 | CELSIUS | null | null | To a solution of methyl ester F4 (4.7 g, 16 mmol) in methanol (100 mL) was added a solution of LiOH (6.8 g, 160 mmol) in water (50 mL) and the solution was heated at 50° C. for 14 h. The methanol was removed in vacuo and the remaining solution was diluted with water (200 mL). The aqueous solution was extracted with eth... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1 | Other | CO.O | 50 | null | COC(=O)[C@H]1N(C(=O)OC(C)(C)C)CC(F)(F)C1(C)C>CO.O>CC(C)(C)OC(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d385b842dcb8486f8120e8156d84ee72 | Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc3[nH]ccc23)CSC1(C)C>>C(=NC1CCCCC1)=NC1CCCCC1 | C(C1=CC=CC=C1)[C@@H]([C@@H](C(=O)N1CSC([C@H]1C(NCC1=C(C=CC=C1)C)=O)(C)C)O)NC(=O)C=1C=2C=CNC2C=CC1.C(C(=O)Cl)(=O)Cl>>C1CCC(CC1)N=C=NC2CCCCC2 | CC1(C)SCN(C(=O)[C@@H](O)[C@H](C[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[NH:2]C(=O)c2cccc3[nH]ccc23)[C@@H]1[C:1](=O)[NH:9]C[c:3]1[c:4](C)[cH:5][cH:6][cH:7][cH:8]1>>[C:1](=[N:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)=[N:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc3[nH]ccc23)CSC1(C)C | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | 538ddd674bde18b53fb4ccafefa5341c3540f86a87a989dcee7517203db670b8 | d9ec5c57131455454104568e26fb4fab11286122808261cdbde5f0eed14d6297 | C(=NC1CCCCC1)=NC1CCCCC1 | C-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6]:1-C-[NH;D2;+0:7]-[C;H0;D3;+0:8](=O)-[C@H]1-N(-C(=O)-[C@@H](-O)-[C@H](-C-[c;H0;D3;+0:9]2:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:2)-[NH;D2;+0:15]-C(=O)-c2:c:c:c:c3:[nH]:c:c:c:2:3)-C-S-C-1(-C)-C>>[C;H0;D2;+0... | null | [] | null | null | null | null | The synthesis of compounds with the general structure 27 is as follows. The boc-protected thiazolidine carboxylic acid 1 is converted to amino-ketones 26 with requisite grignard reagents 25 in the presence of oxalyl chloride. Final compounds 27 are obtained by a DCC-mediated coupling of 26 and 4 followed by deprotectio... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amide.Tertiary amide.Secondary alcohol.Monosulfide | null | C1CSCN1.c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | C1CCCCC1.C1CCCCC1 | C1CCCCC1.C1CCCCC1 | Other | null | null | null | Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc3[nH]ccc23)CSC1(C)C>>C(=NC1CCCCC1)=NC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5384d80117d446df9b0c3b20dba41e15 | C=CC[CH2][Mg][Br].Cc1c(O)cccc1C(=O)NC(Cc1ccccc1)C(O)C(=O)N1CC(F)(F)C(C)(C)C1C(=O)NCC(C)C.Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc3[nH]ccc23)CSC1(C)C>>C=CCCC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(O)c2C)CSC1(C)C | C(C1=CC=CC=C1)[C@@H]([C@@H](C(=O)N1CSC([C@H]1C(NCC1=C(C=CC=C1)C)=O)(C)C)O)NC(=O)C=1C=2C=CNC2C=CC1.Cl.O1CCOCC1.C1CCC(CC1)N=C=NC2CCCCC2.C(C(C)C)NC(=O)C1N(CC(C1(C)C)(F)F)C(C(C(CC1=CC=CC=C1)NC(C1=C(C(=CC=C1)O)C)=O)O)=O.C=1C=CC2=C(C1)N=NN2O.C(C(=O)Cl)(=O)Cl.NC(=O)N.C(CC=C)[Mg]Br>>C(C1=CC=CC=C1)[C@@H]([C@@H](C(=O)N1CSC([C@H]... | [Br][Mg][CH2:4][CH2:3][CH:2]=[CH2:1].CC(C)CNC(=O)C1N(C(=O)C(O)C(Cc2ccccc2)[NH:21][C:22](=[O:23])[c:24]2[cH:25][cH:26][cH:27][c:28]([OH:29])[c:30]2[CH3:31])CC(F)(F)C1(C)C.Cc1ccccc1CN[C:5](=[O:6])[C@H:7]1[N:8]([C:9](=[O:10])[C@@H:11]([OH:12])[C@@H:13](NC(=O)c2cccc3[nH]ccc23)[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:... | C=CC[CH2][Mg][Br].Cc1c(O)cccc1C(=O)NC(Cc1ccccc1)C(O)C(=O)N1CC(F)(F)C(C)(C)C1C(=O)NCC(C)C.Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc3[nH]ccc23)CSC1(C)C | C=CCCC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(O)c2C)CSC1(C)C | null | CN(C)C=O | CO.CCOC(=O)C.C1=CC=CC=C1 | C-C Coupling | OtherReaction | 3ea2ba0f4e00afeaf7d035af0d20bb04b51393f46f861eaf234b1d38b28b80e7 | 2fce7fb9501f126448a0631d65141b902678e094a286cc295865f4eb4efad0f3 | O=C(N[C@H](CC(=O)N1CCSC1)Cc1ccccc1)c1ccccc1 | C-C(-C)-C-N-C(=O)-C1-N(-C(=O)-C(-O)-C(-C-c2:c:c:c:c:c:2)-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4])-C-C(-F)(-F)-C-1(-C)-C.C-c1:c:c:c:c:c:1-C-N-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[#16:9]-[C:10]-[#7:11]-1-[C:12](=[O;D1;H0:13])-[C:14](-[O;D1;H1:15])-[C@@H;D3;+0:16](-N-C(=O)-c1:c:c:c:c2:[nH]:c:c:c:1:2)-[C:17]-[c:18].[B... | null | [] | 0 | CELSIUS | 1 | HOUR | The title compound was prepared as follows. (R)-5,5-Dimethyl-thiazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 1 (1.0 g, 3.80 mmol) was dissolved in benzene (10 mL) and cooled to 0° C. with magnetic stirring. Two drops of DMF were added followed by a drop wise addition of oxalyl chloride (0.33 mL, 3.80 mmol). When ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Tertiary halide.Tertiary halide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Tertiary amide.Secondary alcohol | Ketone.Secondary amide | C1CCNC1.c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | C1CSC[NH]1.c1ccccc1.c1ccccc1 | HF.Br-.Mg | CN(C)C=O.CO.CCOC(=O)C.C1=CC=CC=C1 | 0 | 1 | C=CC[CH2][Mg][Br].Cc1c(O)cccc1C(=O)NC(Cc1ccccc1)C(O)C(=O)N1CC(F)(F)C(C)(C)C1C(=O)NCC(C)C.Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc3[nH]ccc23)CSC1(C)C>CN(C)C=O.CO.CCOC(=O)C.C1=CC=CC=C1>C=CCCC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(O)c2C)CSC1(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ddaf3aaea1c482daa89be5ed34bc6fa | CC(C)(C)OC(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)O.NCC(F)(F)F>>CC1(C)[C@@H](C(=O)NCC(F)(F)F)NCC1(F)F | FC(CN)(F)F.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.CCN(CC)CC.C(C)(C)(C)OC(=O)N1[C@@H](C(C(C1)(F)F)(C)C)C(=O)O>>FC(CNC(=O)[C@H]1NCC(C1(C)C)(F)F)(F)F | CC(C)(C)OC(=O)[N:13]1[C@H:4]([C:5](O)=[O:6])[C:2]([CH3:1])([CH3:3])[C:15]([F:16])([F:17])[CH2:14]1.[NH2:7][CH2:8][C:9]([F:10])([F:11])[F:12]>>[CH3:1][C:2]1([CH3:3])[C@@H:4]([C:5](=[O:6])[NH:7][CH2:8][C:9]([F:10])([F:11])[F:12])[NH:13][CH2:14][C:15]1([F:16])[F:17] | CC(C)(C)OC(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)O.NCC(F)(F)F | CC1(C)[C@@H](C(=O)NCC(F)(F)F)NCC1(F)F | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 8899da95932e3324f1403e459ddb4b49454b709b00c364f61cbcfd02ca1e98f0 | 9f74be20683ae20656a7135e9a9eaad2dfa782f75ac656d32f38d1324fe876ad | C1CCNC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[F;D1;H0:8]-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[C:12]-[NH2;D1;+0:13]>>[F;D1;H0:8]-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 107 | [{"value": 93.9, "product": "FC(CNC(=O)[C@H]1NCC(C1(C)C)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 107.0, "product": "FC(CNC(=O)[C@H]1NCC(C1(C)C)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | NEt3 (75.2 g, 743 mmol) was slowly added to a 10° C. solution of (2S)-4,4-difluoro-3,3-dimethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (98.3 g, 352 mmol), chlorodiphenylphosphate (101 g, 376 mmol), and ethyl acetate (1.0 L). The mixture was warmed to ambient temperature for 45 min., and was then cooled to... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | HO- | C(C)(=O)OCC | null | 24 | CC(C)(C)OC(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)O.NCC(F)(F)F>C(C)(=O)OCC>CC1(C)[C@@H](C(=O)NCC(F)(F)F)NCC1(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-880511a3a6614ec2a76016bac450f560 | CC(=O)Oc1cccc(C(=O)Cl)c1C.N[C@@H](Cc1ccccc1)[C@H](O)C(=O)O>>CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)C(=O)O)c1C | N[C@H]([C@@H](C(=O)O)O)CC1=CC=CC=C1.[Na+].[Cl-].Cl.CCN(CC)CC.ClC(=O)C=1C(=C(C=CC1)OC(C)=O)C>>C(C)(=O)OC=1C(=C(C(=O)N[C@H]([C@@H](C(=O)O)O)CC2=CC=CC=C2)C=CC1)C | Cl[C:10]([c:9]1[cH:8][cH:7][cH:6][c:5]([O:4][C:2]([CH3:1])=[O:3])[c:26]1[CH3:27])=[O:11].[NH2:12][C@@H:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C@H:21]([OH:22])[C:23](=[O:24])[OH:25]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][c:15]2[cH:16][cH:17][cH:... | CC(=O)Oc1cccc(C(=O)Cl)c1C.N[C@@H](Cc1ccccc1)[C@H](O)C(=O)O | CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)C(=O)O)c1C | null | null | C1CCOC1.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C:6]-[C:7](-[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 92 | [{"value": 92.0, "product": "C(C)(=O)OC=1C(=C(C(=O)N[C@H]([C@@H](C(=O)O)O)CC2=CC=CC=C2)C=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "C(C)(=O)OC=1C(=C(C(=O)N[C@H]([C@@H](C(=O)O)O)CC2=CC=CC=C2)C=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 6 | CELSIUS | 45 | MINUTE | (2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyric acid (185 g; 948 mmol) was added to a 5-L flask and was suspended in THF (695 mL). H2O (695 mL) was poured in, followed by NEt3 (277 mL; 1990 mmol). After stirring for 45 min, the solution was cooled to 6° C. A solution of acetic acid 3-chlorocarbonyl-2-methyl-phenyl ester (20... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1.O | 6 | 0.75 | CC(=O)Oc1cccc(C(=O)Cl)c1C.N[C@@H](Cc1ccccc1)[C@H](O)C(=O)O>C1CCOC1.O>CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)C(=O)O)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30a35cd5f5af40f8affe617172750c0a | CC(=O)OC(C)=O.CC(=O)Oc1cccc(C(=O)Cl)c1C.N[C@@H](Cc1ccccc1)[C@H](O)C(=O)O>>CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](OC(C)=O)C(=O)O)c1C | CCN(CC)CC.ClC(=O)C=1C(=C(C=CC1)OC(C)=O)C.C(C)(=O)OC(C)=O.CS(=O)(=O)O.ClC(=O)C=1C(=C(C=CC1)OC(C)=O)C.N[C@H]([C@@H](C(=O)O)O)CC1=CC=CC=C1.Cl.N[C@H]([C@@H](C(=O)O)O)CC1=CC=CC=C1.[Na+].[Cl-]>>C(C)(=O)O[C@H](C(=O)O)[C@H](CC1=CC=CC=C1)NC(C1=C(C(=CC=C1)OC(C)=O)C)=O | CC(=O)O[C:23]([CH3:24])=[O:25].Cl[C:10]([c:9]1[cH:8][cH:7][cH:6][c:5]([O:4][C:2]([CH3:1])=[O:3])[c:29]1[CH3:30])=[O:11].[NH2:12][C@@H:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C@H:21]([OH:22])[C:26](=[O:27])[OH:28]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[NH:12][C@@H:13]([C... | CC(=O)OC(C)=O.CC(=O)Oc1cccc(C(=O)Cl)c1C.N[C@@H](Cc1ccccc1)[C@H](O)C(=O)O | CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](OC(C)=O)C(=O)O)c1C | null | null | C1CCOC1.O | Acylation | OtherReaction | 1f40141642d499a910e2be29a5c356b8d1916b798e754a7bf29128c868fd726f | 9d0de0954dbd386424958adc515d1e2b9ac348539dd05e192e9ae13648a42d14 | O=C(NCCc1ccccc1)c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].Cl-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](-[OH;D1;+0:13])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8])-[C:12](-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](-[C;D1;H3:2... | 74.8 | [{"value": 74.5, "product": "C(C)(=O)O[C@H](C(=O)O)[C@H](CC1=CC=CC=C1)NC(C1=C(C(=CC=C1)OC(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.8, "product": "C(C)(=O)O[C@H](C(=O)O)[C@H](CC1=CC=CC=C1)NC(C1=C(C(=CC=C1)OC(C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A mixture of (2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyric acid (110 kg, 563 mol), NaCl (195 kg), and THF (413 L) was charged with NEt3 (120 kg, 1183 mol) and H2O (414 L) at ambient temperature. The resulting mixture was cooled to 0° C. Acetic acid 3-chlorocarbonyl-2-methyl-phenyl ester (120 kg, 563 mol) was added to a se... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Anhydride.Secondary alcohol.Primary amine | Ester.Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1.O | 0 | 1 | CC(=O)OC(C)=O.CC(=O)Oc1cccc(C(=O)Cl)c1C.N[C@@H](Cc1ccccc1)[C@H](O)C(=O)O>C1CCOC1.O>CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](OC(C)=O)C(=O)O)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6441064f6441478a86d1aabab4cdf806 | CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](OC(C)=O)C(=O)O)c1C.CC1(C)[C@@H](C(=O)NCC(F)(F)F)NCC1(F)F>>Cc1c(O)cccc1C(=O)N[C@@H](Cc1ccccc1)[C@H](O)C(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)NCC(F)(F)F | [OH-].[K+].Cl.FC(CNC(=O)[C@H]1NCC(C1(C)C)(F)F)(F)F.C(=O)([O-])[O-].[K+].[K+].N1=CC=CC=C1.C(C)(=O)O[C@H](C(=O)O)[C@H](CC1=CC=CC=C1)NC(C1=C(C(=CC=C1)OC(C)=O)C)=O.O=S(Cl)Cl>>FC(CNC(=O)[C@H]1N(CC(C1(C)C)(F)F)C([C@H]([C@H](CC1=CC=CC=C1)NC(C1=C(C(=CC=C1)O)C)=O)O)=O)(F)F | CC(=O)[O:4][c:3]1[c:2]([CH3:1])[c:8]([C:9](=[O:10])[NH:11][C@@H:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C@H:20]([O:21]C(C)=O)[C:22](O)=[O:23])[cH:7][cH:6][cH:5]1.[NH:24]1[CH2:25][C:26]([F:27])([F:28])[C:29]([CH3:30])([CH3:31])[C@H:32]1[C:33](=[O:34])[NH:35][CH2:36][C:37]([F:38])([F:39])[F:40]>>[CH3:1][... | CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](OC(C)=O)C(=O)O)c1C.CC1(C)[C@@H](C(=O)NCC(F)(F)F)NCC1(F)F | Cc1c(O)cccc1C(=O)N[C@@H](Cc1ccccc1)[C@H](O)C(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)NCC(F)(F)F | null | O=S(Cl)Cl | CO.C(C)#N | Acylation | OtherReaction | 97699d63ad0156c1a1922ec37bbe5330b0f1de394b80c3f48d07ee3a874d43b8 | b9650ab476311935d7fb14152448c8cf415d0d87f9bb64ac304f365987b4eb40 | O=C(N[C@H](CC(=O)N1CCCC1)Cc1ccccc1)c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](-O)=[O;D1;H0:5].C-C(=O)-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9].[C:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[C:14]1-[C:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[C:3]-[C:2](-[OH;D1;+0:1])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:18]1-[C:17]-[C:16]-[C:15]-[C:14]-1-[C:12](=[O;D1;H0:13])-[... | 96.9 | [{"value": 96.9, "product": "FC(CNC(=O)[C@H]1N(CC(C1(C)C)(F)F)C([C@H]([C@H](CC1=CC=CC=C1)NC(C1=C(C(=CC=C1)O)C)=O)O)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 25 | MINUTE | Pyridine (149 g, 1.89 mol) was added to a solution of (2S,3S)-2-acetoxy-3-(3-acetoxy-2-methyl-benzoylamino)-4-phenyl-butyric acid (193 g, 468 mmol) and acetonitrile (1.6 L) at ambient temperature, and the mixture was then cooled to 10° C. A solution of SOCl2 (62.3 g, 523 mmol) and acetonitrile (50 mL) was added over 15... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ester.Secondary amine | Tertiary amide.Secondary alcohol.Aromatic alcohol | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1 | HO- | O=S(Cl)Cl.CO.C(C)#N | 10 | 0.416667 | CC(=O)Oc1cccc(C(=O)N[C@@H](Cc2ccccc2)[C@H](OC(C)=O)C(=O)O)c1C.CC1(C)[C@@H](C(=O)NCC(F)(F)F)NCC1(F)F>O=S(Cl)Cl.CO.C(C)#N>Cc1c(O)cccc1C(=O)N[C@@H](Cc1ccccc1)[C@H](O)C(=O)N1CC(F)(F)C(C)(C)[C@H]1C(=O)NCC(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7bbfff702a9544b2a0b294e530bca861 | [Li][CH2]CCC>>C1=c2ccccc2=c2cc3c(cc21)=c1ccccc1=C3 | [OH-].[Na+].C(CCC)[Li]>>C1=CC=CC2=C3C=C4C(C=C3C=C12)=C1C=CC=CC1=C4 | [Li][CH2:4][CH2:5][CH2:6][CH3:1]>>[CH:1]1=[c:2]2[cH:3][cH:4][cH:5][cH:6][c:7]2=[c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]21)=[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1=[CH:20]3 | [Li][CH2]CCC | C1=c2ccccc2=c2cc3c(cc21)=c1ccccc1=C3 | null | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC | CS(=O)C | C-C Coupling | OtherReaction | 3c06a7115f226f9aa9df56c17c54ed3166880417664e7a0651f2ce81914ab4b3 | 221a06c8330d414f5c9deb6ca3e77f4b5d95a05764651f7786566c89564d6ddd | C1=c2ccccc2=c2cc3c(cc21)=c1ccccc1=C3 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[Li]>>[c:5]:[c:6]1:[c:7]=[c:8]2:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:9]:[c:10]:2=[CH;D2;+0:1]-1 | null | [] | null | null | null | null | Monomers of Formula IV, wherein —Ar1(Ey)a- is Formula XXXV, XXXVI, XXXVII, or XXXVIII may be made as illustrated by the preparation of a 2,8-dibromo-6,12-dihydroindeno[1,2-b]fluorene using the process of Reaction Scheme X. In step (1), Suzuki coupling of 2-(2,5-dimethylphenyl)-4,4,5,5-tetramethyl [1,3,2]dioxaborolane w... | 10.6084/m9.figshare.5104873.v1 | null | Alkyl lithium | null | null | C1=c2ccccc2c2cc3c(cc21)c1ccccc1=C3 | C1=c2ccccc2c2cc3c(cc21)c1ccccc1=C3 | Li | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.CS(=O)C | null | null | [Li][CH2]CCC>[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.CS(=O)C>C1=c2ccccc2=c2cc3c(cc21)=c1ccccc1=C3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90306718fb4f43d4831ccc3ff610a7d0 | CCCCCCCCOc1ccc(C(=O)NN)cc1.O=C(Cl)c1ccc(Cl)cc1Cl>>CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1 | ClC1=C(C(=O)Cl)C=CC(=C1)Cl.C(CCCCCCC)OC1=CC=C(C(=O)NN)C=C1.C(C)N(CC)CC.C(Cl)(Cl)Cl>>ClC1=C(C(=O)NNC(C2=CC=C(C=C2)OCCCCCCCC)=O)C=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[NH:16][NH2:17])[cH:28][cH:29]1.Cl[C:18](=[O:19])[c:20]1[cH:21][cH:24][c:22]([Cl:23])[cH:25][c:26]1[Cl:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[NH:... | CCCCCCCCOc1ccc(C(=O)NN)cc1.O=C(Cl)c1ccc(Cl)cc1Cl | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1 | null | null | null | Acylation | OtherReaction | 761b799dbc756f3fe5f321871eaaf931865e8f9c851e146dd5f1cd87b5610884 | 69be17fc76b847fa5c08d79e6fe47e57636ae6f1f852dce1c8c4d295b8fab938 | O=C(NNC(=O)c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[Cl;D1;H0:7]):[cH;D2;+0:8]:[c:9]:1-[Cl;D1;H0:10].[NH2;D1;+0:11]-[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]>>[Cl;D1;H0:7]-[c;H0;D3;+0:6]1:[cH;D2;+0:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]):[c:9](-... | null | [] | null | null | null | null | Under a blanket of nitrogen, 8.8 g (0.087 mol) 2,4-dichlorobenzoyl chloride was added to a solution of 23.0 g (0.087 mol) 4-octoxybenzoyl hydrazine and 12.13 ml (8.8 g, 0.087 mol) freshly distilled triethylamine in 348 ml dry chloroform. After about one hour of stirring a dense white precipitate of the required product... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine.Aromatic halide | Acylhydrazine.Acylhydrazine.Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | null | null | null | CCCCCCCCOc1ccc(C(=O)NN)cc1.O=C(Cl)c1ccc(Cl)cc1Cl>>CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-670b7034e20343f0812079471845ed0c | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1>>CCCCCCCCOc1ccc(-c2nnc(-c3cc(Cl)ccc3Cl)o2)cc1 | ClC1=C(C(=O)NNC(C2=CC=C(C=C2)OCCCCCCCC)=O)C=C(C=C1)Cl.P(=O)(Cl)(Cl)Cl>>ClC1=C(C=C(C=C1)Cl)C=1OC(=NN1)C1=CC=C(C=C1)OCCCCCCCC | O=[C:14]([c:13]1[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:28][cH:27]1)[NH:15][NH:16][C:17]([c:18]1[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]1[Cl:25])=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[n:15][n:16][c:17](-... | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1 | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Cl)ccc3Cl)o2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1ccc(-c2nnc(-c3ccccc3)o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14])... | 89.3 | [{"value": 89.0, "product": "ClC1=C(C=C(C=C1)Cl)C=1OC(=NN1)C1=CC=C(C=C1)OCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "ClC1=C(C=C(C=C1)Cl)C=1OC(=NN1)C1=CC=C(C=C1)OCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Into a 250 ml flask fitted with a mechanical stirrer and thermometer was introduced 30 g (0.0686 mol) 2,5-dichloro-N′-[4-(octyloxy)benzoyl]benzohydrazide and 181 ml phosphorus oxychloride. This was refluxed and stirred for 8 hrs. About 100 ml of phosphorus oxychloride was distilled off under reduced pressure. The coole... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1ccccc1.c1nnco1.c1ccccc1 | HO- | null | null | 8 | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1>>CCCCCCCCOc1ccc(-c2nnc(-c3cc(Cl)ccc3Cl)o2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e956bcbc77624831a78facc22d0c414d | O=C(NNC(=O)c1c(F)c(F)c(F)c(F)c1F)c1cc(Cl)ccc1Cl>>Fc1c(F)c(F)c(-c2nnc(-c3cc(Cl)ccc3Cl)o2)c(F)c1F | ClC1=C(C(=O)NNC(C2=C(C(=C(C(=C2F)F)F)F)F)=O)C=C(C=C1)Cl>>ClC1=C(C=C(C=C1)Cl)C=1OC(=NN1)C1=C(C(=C(C(=C1F)F)F)F)F | O=[C:8]([c:7]1[c:5]([F:6])[c:3]([F:4])[c:2]([F:1])[c:23]([F:24])[c:21]1[F:22])[NH:9][NH:10][C:11]([c:12]1[cH:13][c:14]([Cl:15])[cH:16][cH:17][c:18]1[Cl:19])=[O:20]>>[F:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7](-[c:8]2[n:9][n:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[cH:16][cH:17][c:18]3[Cl:19])[o:20]2)[c:21]([F:22])[c:23]1[... | O=C(NNC(=O)c1c(F)c(F)c(F)c(F)c1F)c1cc(Cl)ccc1Cl | Fc1c(F)c(F)c(-c2nnc(-c3cc(Cl)ccc3Cl)o2)c(F)c1F | null | null | O=P(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1ccc(-c2nnc(-c3ccccc3)o2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11])-[c;H0;D3;+0:12](:[c:13](-[F;D1;H0:14]):[c:15]):[c:16](-[F;D1;H0:17]):[c:18]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[... | 81 | [{"value": 81.0, "product": "ClC1=C(C=C(C=C1)Cl)C=1OC(=NN1)C1=C(C(=C(C(=C1F)F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "ClC1=C(C=C(C=C1)Cl)C=1OC(=NN1)C1=C(C(=C(C(=C1F)F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the general method of Part B of Example 2, the reaction of 21.0 g (0.05377 mol) 2,5-dichloro-N′-(pentafluorobenzoyl)benzohydrazide in POCl3 gave a product which was recrystallized from ethanol/water to give 16.59 g (81% yield) of 2-(2,5-dichlorophenyl)-5-(pentafluorophenyl)-1,3,4-oxadiazole (10).
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1ccccc1.c1nnco1.c1ccccc1 | HO- | O=P(Cl)(Cl)Cl | null | null | O=C(NNC(=O)c1c(F)c(F)c(F)c(F)c1F)c1cc(Cl)ccc1Cl>O=P(Cl)(Cl)Cl>Fc1c(F)c(F)c(-c2nnc(-c3cc(Cl)ccc3Cl)o2)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07d99d444aa441219797fc1437284320 | Brc1ccc2c(c1)Cc1ccccc1-2.CCCCCCCCBr.CS(C)=O>>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(Br)cc21 | BrC1=CC=2CC3=CC=CC=C3C2C=C1.CS(=O)C.[OH-].[Na+].C(CCCCCCC)Br>>BrC1=CC=2C(C3=CC=CC=C3C2C=C1)(CCCCCCCC)CCCCCCCC | [CH2:9]1[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2-[c:24]2[cH:25][cH:26][c:27]([Br:28])[cH:29][c:30]21.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O=S([CH3:1])[CH3:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[... | Brc1ccc2c(c1)Cc1ccccc1-2.CCCCCCCCBr.CS(C)=O | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(Br)cc21 | null | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC | CCCCCC.O.CCOCC | C-C Coupling | OtherReaction | a284a36a784c7165747eb6ac3a315190aa52b86f84973e6a9f01c74222570118 | 1f732f111e1d2a1aa9984a12e1a044f7d6e06bb6903521843bac3d9b100c13f6 | c1ccc2c(c1)Cc1ccccc1-2 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].O=S(-[CH3;D1;+0:4])-[CH3;D1;+0:5].[c:6]:[c:7]1:[c:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:12]1(-[C:13]-[CH2;D2;+0:5]-[C:14]-[C:15])-[c:7](:[c:6]):[c:8]-[c:9]:[c:10]-1:[c:11].[C:16]-[C:17]-[CH3;D1;+0:4] | 155.4 | [{"value": 78.0, "product": "BrC1=CC=2C(C3=CC=CC=C3C2C=C1)(CCCCCCCC)CCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 155.4, "product": "BrC1=CC=2C(C3=CC=CC=C3C2C=C1)(CCCCCCCC)CCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 3L flask fitted with a mechanical stirrer was charged with 2-bromofluorene (45 g, 183.6 mmole) and 150 mL DMSO. Under a N2 atmosphere was added 80 mL of a 50% aqueous NaOH solution and 2.72 g of benzyltriethylammonium chloride (2.72 g, 11.98 mmole). This was stirred for 2 h at RT. With vigorous mechanical stirring, n... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Sulfoxide | null | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | Br- | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.CCCCCC.O.CCOCC | null | 2 | Brc1ccc2c(c1)Cc1ccccc1-2.CCCCCCCCBr.CS(C)=O>[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.CCCCCC.O.CCOCC>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b79823c605fd4e4aba08c8d0627802ac | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccccc21.O=C=O>>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)O)cc21 | Cl.C(CCCCCCC)C1(C2=CC=CC=C2C=2C=CC=CC12)CCCCCCCC.C(CCC)[Li].C(=O)=O>>C(CCCCCCC)C1(C2=CC=CC=C2C=2C=CC(=CC12)C(=O)O)CCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2-[c:24]2[cH:25][cH:26][cH:27][cH:31][c:32]21.[C:28](=[O:29])=[O:30]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH2:10][CH2:11][C... | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccccc21.O=C=O | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)O)cc21 | null | null | O1CCCC1 | Acylation | OtherReaction | 0ce4771e15c1f239ede6b9a501e04e5332d9a12b56839f196f5d625690ef7799 | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccc2c(c1)Cc1ccccc1-2 | [O;D1;H0:1]=[C;H0;D2;+0:2]=[O;H0;D1;+0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | -60 | CELSIUS | 1 | HOUR | Into a flask fitted with a nitrogen inlet and rubber septum were introduced 2-bromo,-9,9-dioctylfluorene (34.18 g, 72.8 mmole) and dry tetrahydrofuran (300 mL). The solution was cooled to −60° C. and n-butyl lithium (29.1 mL, 2.5M in hexanes, 72.8 mmole) added via a syringe. The reaction mixture was observed to turn re... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | null | O1CCCC1 | -60 | 1 | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccccc21.O=C=O>O1CCCC1>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)O)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b9e1cfe9f4f47438fab95b35771d0d9 | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)O)cc21.O=S(Cl)Cl>>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)Cl)cc21 | C(CCCCCCC)C1(C2=CC=CC=C2C=2C=CC(=CC12)C(=O)O)CCCCCCCC.S(=O)(Cl)Cl.S(=O)(Cl)Cl>>C(CCCCCCC)C1(C2=CC=CC=C2C=2C=CC(=CC12)C(=O)Cl)CCCCCCCC | O[C:28]([c:27]1[cH:26][cH:25][c:24]2[c:32]([cH:31]1)[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1-2)=[O:29].O=S(Cl)[Cl:30]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1([CH2:10... | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)O)cc21.O=S(Cl)Cl | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)Cl)cc21 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)Cc1ccccc1-2 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 9,9-Dioctyl-9H-fluorene-2-carboxylic acid (32.36 g, 74.5 mmole) was refluxed in thionyl chloride (93 g, 782 mmole) for 8 hrs. Unreacted thionyl chloride was distilled off and the residue material used without further purification.
Conditions: See reaction.notes.procedure_details.
Workup: was distilled off; the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12 | HCl | null | null | null | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)O)cc21.O=S(Cl)Cl>>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)Cl)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b6dfbab97d24624aa2762b3813fda4c | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)Cl)cc21.NNC(=O)c1cc(Cl)ccc1Cl>>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)NNC(=O)c3cc(Cl)ccc3Cl)cc21 | ClC1=C(C(=O)NN)C=C(C=C1)Cl.C(C)N(CC)CC.C(CCCCCCC)C1(C2=CC=CC=C2C=2C=CC(=CC12)C(=O)Cl)CCCCCCCC>>ClC1=C(C(=O)NNC(=O)C2=CC=3C(C4=CC=CC=C4C3C=C2)(CCCCCCCC)CCCCCCCC)C=C(C=C1)Cl | Cl[C:28]([c:27]1[cH:26][cH:25][c:24]2[c:43]([cH:42]1)[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1-2)=[O:29].[NH2:30][NH:31][C:32](=[O:33])[c:34]1[cH:35][c:36]([Cl:37])[cH:38][cH:39][c:40]1[Cl:4... | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)Cl)cc21.NNC(=O)c1cc(Cl)ccc1Cl | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)NNC(=O)c3cc(Cl)ccc3Cl)cc21 | null | null | CCCCCCC.ClCCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | O=C(NNC(=O)c1ccc2c(c1)Cc1ccccc1-2)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[c:10])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | DAY | 2,5-Dichlorobenzohydrazide (one equivalent) and triethylamine (one equivalent) were warmed in 500 mL of 1,2-dichloroethane until the solid material had dissolved. On cooling, 9,9-dioctyl-9H-fluorene-2-carbonyl chloride (one equivalent) was added and the mixture stirred at RT for two days. The insolubles were filtered o... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccc2c(c1)Cc1ccccc12.c1ccccc1 | HCl | CCCCCCC.ClCCCl | null | 48 | CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)Cl)cc21.NNC(=O)c1cc(Cl)ccc1Cl>CCCCCCC.ClCCCl>CCCCCCCCC1(CCCCCCCC)c2ccccc2-c2ccc(C(=O)NNC(=O)c3cc(Cl)ccc3Cl)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7768084908b14dee8441d1827dd3fcea | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Br)ccc3Br)o2)cc1.O=C(Cl)c1cc(Cl)cc(Cl)c1>>CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)cc(Cl)c2)cc1 | BrC1=C(C=C(C=C1)Br)C=1OC(=NN1)C1=CC=C(C=C1)OCCCCCCCC.ClC=1C=C(C(=O)Cl)C=C(C1)Cl>>ClC=1C=C(C(=O)NNC(C2=CC=C(C=C2)OCCCCCCCC)=O)C=C(C1)Cl | Brc1ccc(Br)c(-c2[o:15][c:14](-[c:13]3[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:29][cH:28]3)[n:16][n:17]2)c1.Cl[C:18](=[O:19])[c:20]1[cH:21][c:22]([Cl:23])[cH:24][c:25]([Cl:26])[cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13](... | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Br)ccc3Br)o2)cc1.O=C(Cl)c1cc(Cl)cc(Cl)c1 | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)cc(Cl)c2)cc1 | null | null | null | Acylation | OtherReaction | 288c2066a1396b17c0ec0e1051646df7119eda51df2944b050847bb325c4ecb6 | ca7cf5c2c3f17186f59d512d2024f294526cf9392bb5b46798280be1bc1d55f1 | O=C(NNC(=O)c1ccccc1)c1ccccc1 | Br-c1:c:c:c(-Br):c(-c2:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[o;H0;D2;+0:9]:2):c:1.Cl-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]>>[O;D1;H0:11]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:9])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])... | 60 | [{"value": 60.0, "product": "ClC=1C=C(C(=O)NNC(C2=CC=C(C=C2)OCCCCCCCC)=O)C=C(C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (1) in Example 3, the reaction of 3,5-dichlorobenzoyl chloride (20.0 g, 0.010 mole) with 4-octoxybenzoyl hydrazide (25.24 g, 0.010 mole) gave the intermediate 3,5-dichloro-N′-[4-(octyloxy)benzoyl]benzohydrazide (25 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Aromatic halide | Acylhydrazine.Acylhydrazine | c1ccccc1.c1nnco1 | null | c1ccccc1.c1ccccc1 | HCl.Br- | null | null | null | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Br)ccc3Br)o2)cc1.O=C(Cl)c1cc(Cl)cc(Cl)c1>>CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)cc(Cl)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1059742cd73b4077bc4e555f101e0dca | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Br)ccc3Br)o2)cc1.O=C(Cl)c1cc(Br)cc(Br)c1>>CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Br)cc(Br)c2)cc1 | BrC1=C(C=C(C=C1)Br)C=1OC(=NN1)C1=CC=C(C=C1)OCCCCCCCC.BrC=1C=C(C(=O)Cl)C=C(C1)Br>>BrC=1C=C(C(=O)NNC(C2=CC=C(C=C2)OCCCCCCCC)=O)C=C(C1)Br | Brc1ccc(Br)c(-c2[o:15][c:14](-[c:13]3[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:29][cH:28]3)[n:16][n:17]2)c1.Cl[C:18](=[O:19])[c:20]1[cH:21][c:22]([Br:23])[cH:24][c:25]([Br:26])[cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13](... | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Br)ccc3Br)o2)cc1.O=C(Cl)c1cc(Br)cc(Br)c1 | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Br)cc(Br)c2)cc1 | null | null | null | Acylation | OtherReaction | 288c2066a1396b17c0ec0e1051646df7119eda51df2944b050847bb325c4ecb6 | ca7cf5c2c3f17186f59d512d2024f294526cf9392bb5b46798280be1bc1d55f1 | O=C(NNC(=O)c1ccccc1)c1ccccc1 | Br-c1:c:c:c(-Br):c(-c2:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[o;H0;D2;+0:9]:2):c:1.Cl-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]>>[O;D1;H0:11]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:9])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])... | 36 | [{"value": 36.0, "product": "BrC=1C=C(C(=O)NNC(C2=CC=C(C=C2)OCCCCCCCC)=O)C=C(C1)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (1) in Example 3, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octoxybenzoyl hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Aromatic halide | Acylhydrazine.Acylhydrazine | c1ccccc1.c1nnco1 | null | c1ccccc1.c1ccccc1 | HCl.Br- | null | null | null | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Br)ccc3Br)o2)cc1.O=C(Cl)c1cc(Br)cc(Br)c1>>CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Br)cc(Br)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62b08a787a1c47d9ad468eaa7c37bca6 | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1.COc1ccc(N)cc1>>CCCCCCCCOc1ccc(-c2nnc(-c3cc(Cl)ccc3Cl)n2-c2ccc(OC)cc2)cc1 | ClC1=C(C(=O)NNC(C2=CC=C(C=C2)OCCCCCCCC)=O)C=C(C=C1)Cl.COC1=CC=C(C=C1)N.P(Cl)(Cl)Cl.C(Cl)Cl.CN(C)C=O>>ClC1=C(C=C(C=C1)Cl)C1=NN=C(N1C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OCCCCCCCC | O=[C:14]([c:13]1[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:36][cH:35]1)[NH:15][NH:16][C:17](=O)[c:18]1[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]1[Cl:25].[NH2:26][c:27]1[cH:28][cH:29][c:30]([O:31][CH3:32])[cH:33][cH:34]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8... | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1.COc1ccc(N)cc1 | CCCCCCCCOc1ccc(-c2nnc(-c3cc(Cl)ccc3Cl)n2-c2ccc(OC)cc2)cc1 | null | null | ClC1=C(C=CC=C1)Cl | Aromatic Heterocycle Formation | OtherReaction | dd6aff0a7fa936aa4206620fc45281159b3db63e711bd694b764463daf82cbcc | 1f5c57f9ffab8a5214b697412c1715772187bdfe92c542c30f8b933239b9a67f | c1ccc(-c2nnc(-c3ccccc3)n2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[Cl;D1;H0:9]):[c:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[NH2;D1;+0:16]-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21]>>[Cl;D1;H0:9]-[c:8](:[c:10]):[c;H0;D3;+0:5](-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[... | 34 | [{"value": 34.0, "product": "ClC1=C(C=C(C=C1)Cl)C1=NN=C(N1C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.9, "product": "ClC1=C(C=C(C=C1)Cl)C1=NN=C(N1C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | Into a 1L round-bottomed flask fitted with a mechanical stirrer, reflux condenser and nitrogen inlet were introduced 2,5-dichloro-N′-[4-(octyloxy)benzoyl]benzohydrazide (40 g, 0.09146 mole, 1 equivalent), p-anisidine (67.60 g, 0.5487 mole, 6 equivalents) and 300 mL 1,2-dichlorobenzene. Mechanical stirring resulted in p... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Primary amine | null | null | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1.c1ccccc1.c1ccccc1 | HO- | ClC1=C(C=CC=C1)Cl | 180 | null | CCCCCCCCOc1ccc(C(=O)NNC(=O)c2cc(Cl)ccc2Cl)cc1.COc1ccc(N)cc1>ClC1=C(C=CC=C1)Cl>CCCCCCCCOc1ccc(-c2nnc(-c3cc(Cl)ccc3Cl)n2-c2ccc(OC)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b216441cd7154d13b5ba6ea06150db8a | Brc1ccc(N(c2ccccc2)c2ccccc2)cc1.CC(C)OB1OC(C)(C)C(C)(C)O1>>CC1(C)OB(c2ccc(N(c3ccccc3)c3ccccc3)cc2)OC1(C)C | C(C)(C)OB1OC(C(O1)(C)C)(C)C.C(CCC)[Li].CC(=O)C.C(=O)=O.BrC1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1>>C1(=CC=CC=C1)N(C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 | Br[c:6]1[cH:7][cH:8][c:9]([N:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1.CC(C)O[B:5]1[O:4][C:2]([CH3:1])([CH3:3])[C:26]([CH3:27])([CH3:28])[O:25]1>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([N:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)... | Brc1ccc(N(c2ccccc2)c2ccccc2)cc1.CC(C)OB1OC(C)(C)C(C)(C)O1 | CC1(C)OB(c2ccc(N(c3ccccc3)c3ccccc3)cc2)OC1(C)C | null | null | C1CCOC1 | Miscellaneous | Preparation of boronic ethers | 92f0efbef99902c051a9cb9dac0843fdf28aedf7deea272cb0c3285e02b5842d | f1d1202adfbfb63cdbea2fa31eb5766b49914acb653b77a04e8043b460a99de7 | c1ccc(N(c2ccccc2)c2ccc(B3OCCO3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)-O-[B;H0;D3;+0:6]1-[#8:7]-[C:8]-[C:9]-[#8:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[B;H0;D3;+0:6]1-[#8:7]-[C:8]-[C:9]-[#8:10]-1):[c:4]:[c:5] | 72.8 | [{"value": 72.8, "product": "C1(=CC=CC=C1)N(C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "C1(=CC=CC=C1)N(C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 12 | HOUR | n-Butyllithium was added dropwise via syringe to a −78° C. (acetone-dry ice cooling bath) solution of 4-bromo-N,N-diphenylaniline (24 g, 0.074 mole) in 175 ml dry THF. Stirring was continued at −78° C. for an hour and then at −50° C. for an hour. The mixture was cooled to −78° C. and 2-isopropoxy-4,4,5,5-tetramethyl-1,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic ester | c1ccccc1.[B]1OCCO1 | [B]1OCCO1.c1ccccc1 | [B]1OCCO1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C1CCOC1 | -78 | 12 | Brc1ccc(N(c2ccccc2)c2ccccc2)cc1.CC(C)OB1OC(C)(C)C(C)(C)O1>C1CCOC1>CC1(C)OB(c2ccc(N(c3ccccc3)c3ccccc3)cc2)OC1(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2dbec03729041cdb275660146cddfe5 | Brc1ccc(N(c2ccccc2)c2ccccc2)cc1.CCCCCCCCC1(CCCCCCCC)c2cc(B3OC(C)(C)C(C)(C)O3)ccc2-c2ccc(B3OC(C)(C)C(C)(C)O3)cc21>>CCCCCCCCC1(CCCCCCCC)c2cc(B3OC(C)(C)C(C)(C)O3)ccc2-c2ccc(-c3ccc(N(c4ccccc4)c4ccccc4)cc3)cc21 | BrC1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C(CCCCCCC)C1(C2=CC(=CC=C2C=2C=CC(=CC12)B1OC(C(O1)(C)C)(C)C)B1OC(C(O1)(C)C)(C)C)CCCCCCCC.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C>>C(CCCCCCC)C1(C2=CC(=CC=C2C=2C=CC(=CC12)C1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1)B1OC(C(O1)(C)C)(C)C)CCCCCCCC | Br[c:37]1[cH:38][cH:39][c:40]([N:41]([c:42]2[cH:43][cH:44][cH:45][cH:46][cH:47]2)[c:48]2[cH:49][cH:50][cH:51][cH:52][cH:53]2)[cH:54][cH:55]1.CC1(C)OB([c:36]2[cH:35][cH:34][c:33]3[c:57]([cH:56]2)[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:1... | Brc1ccc(N(c2ccccc2)c2ccccc2)cc1.CCCCCCCCC1(CCCCCCCC)c2cc(B3OC(C)(C)C(C)(C)O3)ccc2-c2ccc(B3OC(C)(C)C(C)(C)O3)cc21 | CCCCCCCCC1(CCCCCCCC)c2cc(B3OC(C)(C)C(C)(C)O3)ccc2-c2ccc(-c3ccc(N(c4ccccc4)c4ccccc4)cc3)cc21 | null | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C.CCCCCC.CC(=O)C.O | C-C Coupling | Suzuki coupling with boronic esters | 858fc14d0faff550373a6534bd7775e643e4c7e4118d9fd345d43107c7cb35ce | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(N(c2ccccc2)c2ccc(-c3ccc4c(c3)Cc3cc(B5OCCO5)ccc3-4)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C1(-C)-O-B(-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-O-C-1(-C)-C>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | null | [] | null | null | 8 | HOUR | 4-Bromo-N,N-diphenylaniline (19.44 g, 60 mmole, 1 equiv), 2-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76.9 g, 120 mmole, 2 equiv), Aliquat™ 336 (tricaprylylmethylammonium chloride) (6 g, 15 mmole, 0.25 equiv) and 2M sodium carbonate solution (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccccc1.B1OCCO1.c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12.c1ccccc1 | [B]1OCCO1.c1ccc2c(c1)Cc1ccccc12.c1ccccc1.c1ccccc1.c1ccccc1 | HBr.B | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.CCCCCC.CC(=O)C.O | null | 8 | Brc1ccc(N(c2ccccc2)c2ccccc2)cc1.CCCCCCCCC1(CCCCCCCC)c2cc(B3OC(C)(C)C(C)(C)O3)ccc2-c2ccc(B3OC(C)(C)C(C)(C)O3)cc21>CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-895ac0d05bb4491a9c8ea71c95f01699 | c1ccc2ccccc2c1>>c1ccc2ccccc2c1 | C(C=C)#N.[Na][Na].C1=CC=CC2=CC=CC=C12.[Na]>>C1=CC=CC2=CC=CC=C12.[Na] | [cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11]1>>[cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11]1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | null | C1CCOC1.O1CCCC1.C1=CC=CC=C1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2ccccc2c1 | null | null | [] | null | null | null | null | In this example, a triblock copolymer (PAN-PEO-PAN) consisting of polyethylene oxide (PEO) chain and polyacrylonitrile (PAN) chains is synthesized by living anion polymerization. Using a polyethylene oxide macromer (disodium salt of polyethylene oxide) as a reaction initiator, acrylonitrile is polymerized. Tetrahydrofu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ccccc2c1 | null | C1CCOC1.O1CCCC1.C1=CC=CC=C1 | null | null | c1ccc2ccccc2c1>C1CCOC1.O1CCCC1.C1=CC=CC=C1>c1ccc2ccccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b29dfb38e38e4655b60cb3c4a305e099 | CC(C)=CCCC(C)=CC(C)O.O.c1ccncc1>>CCCC(=O)OC(C)C=C(C)CCC=C(C)C | CC(=CC(C)O)CCC=C(C)C.N1=CC=CC=C1.O>>C(CCC)(=O)OC(C)C=C(CCC=C(C)C)C | [OH:6][CH:7]([CH3:8])[CH:9]=[C:10]([CH3:11])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:16])[CH3:17].[OH2:5].c1[cH:1]n[cH:2][cH:3][cH:4]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[O:6][CH:7]([CH3:8])[CH:9]=[C:10]([CH3:11])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:16])[CH3:17] | CC(C)=CCCC(C)=CC(C)O.O.c1ccncc1 | CCCC(=O)OC(C)C=C(C)CCC=C(C)C | null | null | C(C)(C)(C)OC | Acylation | OtherReaction | f790ec7b0fd3b982c3d39b4a19f6c2dd50f79014af302c044031965b79c42b1f | 37f9d0c402085ae7a53dbce85561bce6850cbef4177e39b629509223b5de2bec | null | [C:1]-[C:2](-[C;D1;H3:3])=[C:4]-[C:5](-[C;D1;H3:6])-[OH;D1;+0:7].[OH2;D0;+0:8].[cH;D2;+0:9]1:c:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:n:1>>[C:1]-[C:2](-[C;D1;H3:3])=[C:4]-[C:5](-[C;D1;H3:6])-[O;H0;D2;+0:7]-[C;H0;D3;+0:10](=[O;H0;D1;+0:8])-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH3;D1;+0:9] | 76 | [{"value": 76.0, "product": "C(CCC)(=O)OC(C)C=C(CCC=C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 90 | MINUTE | A flask was charged with 4,8-dimethyl-3,7-nonadien-2-ol CAS 67845-50-5 (20 grams), buryric anhydride (25 grams) and pyridine (12.5 grams). The mixture was stirred and heated to 100° C. The reaction was held at 100° C.±1° C. for 90 minutes and then cooled to room temperature. The reaction mixture was diluted with water ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ester | c1ccncc1 | null | null | Other | C(C)(C)(C)OC | 100 | 1.5 | CC(C)=CCCC(C)=CC(C)O.O.c1ccncc1>C(C)(C)(C)OC>CCCC(=O)OC(C)C=C(C)CCC=C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7afa7b65fe894f658bd2a222ed482b09 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCCCCCCC/C=C\CCCCCCCC(=O)Cl.CCN(C(C)C)C(C)C.NC1CCN(CCCN(CCO)CCO)CC1>>CCCCCCCC/C=C\CCCCCCCC(=O)OCCN(CCCN1CCC(N)CC1)CCOC(=O)CCCCCCC/C=C\CCCCCCCC | Cl.NC1CCN(CC1)CCCN(CCO)CCO.C(C)N(C(C)C)C(C)C.C(CCCCCCC\C=C/CCCCCCCC)(=O)Cl.Cl.C(C)(C)(C)OC(=O)OC(=O)OC(C)(C)C>>NC1CCN(CC1)CCCN(CCOC(CCCCCCC\C=C/CCCCCCCC)=O)CCOC(CCCCCCC\C=C/CCCCCCCC)=O | O=[C:46](O[C:37](O[C:52]([CH3:39])([CH3:51])[CH3:53])=[O:38])O[C:47]([CH3:45])([CH3:48])[CH3:54].Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].N([CH2:40][CH3:49])([CH:41]([CH3:42])[CH3:44])[CH:43]([CH3:50])[CH3:55].[OH:2... | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCCCCCCC/C=C\CCCCCCCC(=O)Cl.CCN(C(C)C)C(C)C.NC1CCN(CCCN(CCO)CCO)CC1 | CCCCCCCC/C=C\CCCCCCCC(=O)OCCN(CCCN1CCC(N)CC1)CCOC(=O)CCCCCCC/C=C\CCCCCCCC | null | null | ClCCl | Acylation | OtherReaction | 9dbf3844cc0e0e2441cfde045ee2a732ffc64689c070e533acacde7f797c4cfd | 495d92168bdc4e83330a776b46acfe20e795d5c47b1b7abf885c2953cf50f78c | C1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].O=[C;H0;D3;+0:5](-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-O-[C;H0;D4;+0:8](-[CH3;D1;+0:9])(-[CH3;D1;+0:10])-[CH3;D1;+0:11])-O-[C;H0;D4;+0:12](-[CH3;D1;+0:13])(-[CH3;D1;+0:14])-[CH3;D1;+0:15].[CH3;D1;+0:16]-[CH;D3;+0:17](-[CH3;D1;+0:18])-N(-[CH2;D2;+0:19]-[CH3;D1;+0:20])-[CH;D3;+0:21](... | null | [] | null | null | 6 | HOUR | A suspension of 4.5 g (4 mmol) of the 2-{[3-(4-amino-piperidin-1-yl)-propyl]-(2-hydroxy-ethyl)-amino}-ethanol-hydrochloride described in example 10 in 100 ml dichloromethane is admixed with 3.5 g N-ethyl-diisopropylamine and 0.87 g (4 mmol) pyrocarbonic acid di-t-butyl ester, it is refluxed for 18 h, a solution of 2.4 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Anhydride.Carbonic Ester.Carbonic Ester.Primary alcohol.Primary alcohol.Tertiary amine.Boc.Boc | Ester.Ester | null | null | C1CC[NH]CC1 | HCl | ClCCl | null | 6 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCCCCCCC/C=C\CCCCCCCC(=O)Cl.CCN(C(C)C)C(C)C.NC1CCN(CCCN(CCO)CCO)CC1>ClCCl>CCCCCCCC/C=C\CCCCCCCC(=O)OCCN(CCCN1CCC(N)CC1)CCOC(=O)CCCCCCC/C=C\CCCCCCCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eba59b58661c4797b82e6da436495a6a | C1CCC2CCCCC2C1.CC1C=CCCC1CO>>C=C.C=CC(=O)OC.CC1=CCCCC1 | CC1C=CCCC1CO.C1CCCC2CCCCC12.C(C=C)(=O)OC>>C=C.C(C=C)(=O)OC.COC(C=C)=O.CC1=CCCCC1 | C1C[CH2:20][CH2:21]C2C1C[CH2:1][CH2:2][CH2:14]2.[CH2:9]1[CH:10]([CH2:11][OH:12])[CH:16]([CH3:15])[CH:17]=[CH:18][CH2:19]1>>[CH2:1]=[CH2:2].[CH2:9]=[CH:10][C:11](=[O:12])[O:13][CH3:14].[CH3:15][C:16]1=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21]1 | C1CCC2CCCCC2C1.CC1C=CCCC1CO | C=C.C=CC(=O)OC.CC1=CCCCC1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | e03f654a54717e856a6b117dae7161cc4f856418505a90dd13bcedbf77815f32 | c5e5e990b49042ec3fbbbea463ce70a03f7c1bfbab0c0aa06abcd9bc9aff55c7 | C1=CCCCC1 | C1-C-C2-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-C-2-[CH2;D2;+0:4]-[CH2;D2;+0:5]-1.[C;D1;H3:6]-[CH;D3;+0:7]1-[CH;D2;+0:8]=[CH;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[CH;D3;+0:12]-1-[CH2;D2;+0:13]-[OH;D1;+0:14]>>[C;D1;H3:6]-[C;H0;D3;+0:7]1=[CH;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-1.[CH2;D... | null | [] | 170 | CELSIUS | null | null | 550 ml of decalin® was placed in a flask. To this was added 350 g of Chevron EMAC SP-2260 which has 24 weight % of methyl acrylate (0.9767 moles of methyl acrylate) and 0.48 g of Irganox®1076 (0.1 mole). The temperature of the mixture was gradually raised while stirring. When the temperature reached approximately 120° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ester.Vinyl.Ethylene | C1CCC2CCCCC2C1.C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1 | Other | C(Cl)(Cl)Cl | 170 | null | C1CCC2CCCCC2C1.CC1C=CCCC1CO>C(Cl)(Cl)Cl>C=C.C=CC(=O)OC.CC1=CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cda3828502ec4ec5b4a279b75eb3511f | Brc1ccc2c3c(cccc13)C=C2.c1ccc(-c2oc(-c3ccccc3)c3ccccc23)cc1>>Brc1ccc2c3c(cccc13)-c1c-2c(-c2ccccc2)c2ccccc2c1-c1ccccc1 | C1(=CC=CC=C1)C=1OC(=C2C=CC=CC12)C1=CC=CC=C1.BrC1=CC=C2C=CC=3C=CC=C1C32>>BrC1=C2C=CC=C3C=4C(=C5C(=C(C4C(C=C1)=C32)C3=CC=CC=C3)C=CC=C5)C5=CC=CC=C5 | [Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]13)[CH:12]=[CH:13]2.o1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[c:27]1-[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]13)-[c:12]1[c:13]... | Brc1ccc2c3c(cccc13)C=C2.c1ccc(-c2oc(-c3ccccc3)c3ccccc23)cc1 | Brc1ccc2c3c(cccc13)-c1c-2c(-c2ccccc2)c2ccccc2c1-c1ccccc1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | c0057313ccf14c0588a7076e0b2c718491335f4654089f675311b2f85a180fc7 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2c3c(c(-c4ccccc4)c4ccccc24)-c2cccc4cccc-3c24)cc1 | [c:1]:[c:2](-[c;H0;D3;+0:3]1:o:[c;H0;D3;+0:4](-[c:5](:[c:6]):[c:7]):[c:8](:[c:9]):[c:10]:1:[c:11]):[c:12].[c:13]:[c:14]1:[c;H0;D3;+0:15](:[c:16]:[c:17])-[CH;D2;+0:18]=[CH;D2;+0:19]-[c;H0;D3;+0:20]:1:[c:21]:[c:22]>>[c:13]:[c:14]1:[c;H0;D3;+0:15](:[c:16]:[c:17])-[c;H0;D3;+0:18]2:[c;H0;D3;+0:19](:[c;H0;D3;+0:4](-[c:5](:[c... | 78.3 | [{"value": 78.3, "product": "BrC1=C2C=CC=C3C=4C(=C5C(=C(C4C(C=C1)=C32)C3=CC=CC=C3)C=CC=C5)C5=CC=CC=C5", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 5 g (18.5 mmol) of diphenylisobenzofuran and 4.3 g (18.5 mmol) of 5-bromoacenaphthylene in toluene were agitated for 24 hours at the reflux temperature. The solvent was distilled off in vacuum, after which the residue was dissolved in 500 ml of acetic acid. An aqueous 40% hydrobromic acid solution, 50 cm3, was added to... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2cccc3cccc1c23.c1ccc2cocc2c1 | c1ccc2cc3c(cc2c1)c1cccc2cccc3c21 | c1ccccc1.c1ccccc1.c1ccc2cc3c(cc2c1)c1cccc2cccc3c21 | HO- | C1(=CC=CC=C1)C | 80 | null | Brc1ccc2c3c(cccc13)C=C2.c1ccc(-c2oc(-c3ccccc3)c3ccccc23)cc1>C1(=CC=CC=C1)C>Brc1ccc2c3c(cccc13)-c1c-2c(-c2ccccc2)c2ccccc2c1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ecdbda356a6f4cedb55b2effebef9de2 | Cc1cccc(I)c1.Nc1ccc(N(c2ccccc2)c2ccccc2)cc1>>Cc1cccc(N(c2ccccc2)c2ccc(Nc3ccccc3)cc2)c1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)N(C1=CC=C(C=C1)N)C1=CC=CC=C1.IC=1C=C(C=CC1)C>>C1(=CC=CC=C1)N(C1=CC=C(C=C1)NC1=CC=CC=C1)C=1C=C(C=CC1)C | I[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:27]1.[N:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][c:17]([NH2:18])[cH:25][cH:26]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17]([NH:18][c:19... | Cc1cccc(I)c1.Nc1ccc(N(c2ccccc2)c2ccccc2)cc1 | Cc1cccc(N(c2ccccc2)c2ccc(Nc3ccccc3)cc2)c1 | null | [Cu] | C1CCCC2CCCCC12 | Heteroatom Alkylation and Arylation | OtherReaction | 983ae3a54fa0a225ab4b923349e136039cd2d0ae94bb4e2f54749204f0cdbb5e | 554f2b1f51560c027b3299c2553740485ed806c9efc0f064d29380b1afd24651 | c1ccc(Nc2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[c:10](-[N;H0;D3;+0:11](-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]):[c:20]:[c:21]:1>>[c:13]:[c:12](-[N;H0;D3;+0:11](-[c:10]1:[c:9]:[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]):[c:21]:[c:20... | 48.6 | [{"value": 48.6, "product": "C1(=CC=CC=C1)N(C1=CC=C(C=C1)NC1=CC=CC=C1)C=1C=C(C=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 200 ml reaction vessel 26 grams of N,N-diphenyl-1,4-phenylenediamine and 22 grams of 3-iodotoluene were heated together with 0.3 grams of activated copper powders, 50 grams of potassium carbonate and 50 ml of decalin at an oil bath temperature of 200° C. for 24 hours in an Ar atmosphere. After the completion of th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Tertiary amine | Secondary amine.Tertiary amine | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HI | [Cu].C1CCCC2CCCCC12 | null | null | Cc1cccc(I)c1.Nc1ccc(N(c2ccccc2)c2ccccc2)cc1>[Cu].C1CCCC2CCCCC12>Cc1cccc(N(c2ccccc2)c2ccc(Nc3ccccc3)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55ee4330953246a9a99fcfd9784870dc | CCOC(=O)C(Cl)C(C)=O.Nc1nc[nH]n1>>Cc1nc2ncnn2c(O)c1Cl | NC1=NNC=N1.C(C)OC(C(C(=O)C)Cl)=O>>ClC1=C(N2N=CN=C2N=C1C)O | CCO[C:9](=[O:10])[CH:11]([C:2](=O)[CH3:1])[Cl:12].[NH2:3][c:4]1[n:5][cH:6][nH:7][n:8]1>>[CH3:1][c:2]1[n:3][c:4]2[n:5][cH:6][n:7][n:8]2[c:9]([OH:10])[c:11]1[Cl:12] | CCOC(=O)C(Cl)C(C)=O.Nc1nc[nH]n1 | Cc1nc2ncnn2c(O)c1Cl | null | null | CS(=O)C.CCOCC.CO.C(C)(=O)O.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 75dcea11612c9e0127b99543424125c099f59910f685718c1a8327bb00a448e1 | 5982d21050cdd10eaa2085de3b27e8a365b6320a01662492189af05c1caf6382 | c1cnc2ncnn2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[n;H0;D2;+0:12]:1>>[C;D1;H3:6]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:7]:[c:8]2:[#7;a:9]:[c:10]:[n;H0;D2;+0:11]:[n;H0;D3;+0:12]:2:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:3]:1-[Cl;D1... | null | [] | null | null | 15 | MINUTE | 3-Amino-1,2,4-triazole (4.2 g, 0.05 mol) and ethyl-2-chloro-acetoacetate (12.64 g, 0.0768 mol) were refluxed in acetic acid (15 ml) under a nitrogen atmosphere. The reaction mixture first turned into a clear yellow solution and after about 15 minutes a solid started precipitating. Reflux continued for one hour. The cru... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Aromatic halide.Aromatic alcohol | c1nnc[nH]1 | c1cnc2ncnn2c1 | c1cnc2ncnn2c1 | HO- | CS(=O)C.CCOCC.CO.C(C)(=O)O.CN(C)C=O | null | 0.25 | CCOC(=O)C(Cl)C(C)=O.Nc1nc[nH]n1>CS(=O)C.CCOCC.CO.C(C)(=O)O.CN(C)C=O>Cc1nc2ncnn2c(O)c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1674ca12e1f4271b7def85a3223021c | BrBr.Cc1cc(O)n2ncnc2n1>>Cc1nc2ncnn2c(O)c1Br | OC=1N2N=CN=C2N=C(C1)C.BrBr.O>>BrC1=C(N2N=CN=C2N=C1C)O | Br[Br:12].[CH3:1][c:2]1[n:3][c:4]2[n:5][cH:6][n:7][n:8]2[c:9]([OH:10])[cH:11]1>>[CH3:1][c:2]1[n:3][c:4]2[n:5][cH:6][n:7][n:8]2[c:9]([OH:10])[c:11]1[Br:12] | BrBr.Cc1cc(O)n2ncnc2n1 | Cc1nc2ncnn2c(O)c1Br | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 4e3406de9a4800f640bca4b1687c48fa4b9544115f8ed2823671e0e46f252c68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2ncnn2c1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:[c:10](-[O;D1;H1:11]):[cH;D2;+0:12]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:12]1:[c:3](-[C;D1;H3:2]):[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:[c:10]:1-[O;D1;H1:11] | 83 | [{"value": 82.0, "product": "BrC1=C(N2N=CN=C2N=C1C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "BrC1=C(N2N=CN=C2N=C1C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A suspension of 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene (15.0 g, 0.1 mol) in acetic acid (100 ml) was treated dropwise at 20° C. with a solution of bromine (16.172 g, 0.102 mol) in acetic acid (20 ml). As the reaction progressed, the suspended crystals dissolved and new crystals of brominated product were formed. Af... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2ncnn2c1 | c1cnc2ncnn2c1 | c1cnc2ncnn2c1 | HBr | C(C)(=O)O | null | 2 | BrBr.Cc1cc(O)n2ncnc2n1>C(C)(=O)O>Cc1nc2ncnn2c(O)c1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3d3933bb35bf467b93b0e9c374f0a8b2 | COCCOCCl.Oc1ccc(I)cc1>>COCCOCOc1ccc(I)cc1 | CCOCC.COCCOCCl.IC1=CC=C(C=C1)O.[H-].[Na+]>>COCCOCOC1=CC=C(C=C1)I | Cl[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:7][c:8]1[cH:9][cH:10][c:11]([I:12])[cH:13][cH:14]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([I:12])[cH:13][cH:14]1 | COCCOCCl.Oc1ccc(I)cc1 | COCCOCOc1ccc(I)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of 4-iodophenol (10 g, 45.45 mmol) in 200 ml of anhydrous tetrahydrofuran was treated at 0° C. with sodium hydride (2.36 g, 60% dispersion, 59.09 mmol) for 5 minutes. To the resulting mixture, methoxyethoxymethyl chloride (8.3 ml, 72.73 mmol) was slowly added over a 5-minute period. The mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | O1CCCC1 | 0 | 0.5 | COCCOCCl.Oc1ccc(I)cc1>O1CCCC1>COCCOCOc1ccc(I)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e59131b79bd04d71ba5590af6c25b9b8 | COc1ccc(Br)cc1.O=C1Nc2ccccc2C1=O>>COc1ccc(N2C(=O)C(=O)c3ccccc32)cc1 | [H-].[Na+].N1C(=O)C(=O)C2=CC=CC=C12.BrC1=CC=C(C=C1)OC>>COC1=CC=C(C=C1)N1C(=O)C(=O)C2=CC=CC=C12 | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1.[NH:7]1[C:8](=[O:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[C:8](=[O:9])[C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]32)[cH:18][cH:19]1 | COc1ccc(Br)cc1.O=C1Nc2ccccc2C1=O | COc1ccc(N2C(=O)C(=O)c3ccccc32)cc1 | null | [Cu](I)I | C(C)(=O)OCC.CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling | a6140d1302c1424aae9fd07d1a1cdfb4f8078cc053096587236f0e3c31860bdd | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C1C(=O)N(c2ccccc2)c2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-1=[O;D1;H0:13] | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of isatin (2.5 g, 0.017 mol) in anhydrous DMF (50 ml) was cooled to 0° C. under a nitrogen atmosphere and treated with sodium hydride (0.5 g, 1.2 equivalents). A purple solution was formed which was stirred at 0° C. for 30 minutes and then warmed to room temperature. 4-Bromoanisole (2.13 ml, 1 equivalent) wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Tertiary amide | c1ccccc1.c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HBr | [Cu](I)I.C(C)(=O)OCC.CN(C)C=O | 0 | 0.5 | COc1ccc(Br)cc1.O=C1Nc2ccccc2C1=O>[Cu](I)I.C(C)(=O)OCC.CN(C)C=O>COc1ccc(N2C(=O)C(=O)c3ccccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f33cc32c4cf4ebcbe5ac5bfe604c53b | COc1ccc(N2C(=O)C(=O)c3ccccc32)cc1>>COc1ccc2nc3ccccc3c(C(=O)O)c2c1 | COC1=CC=C(C=C1)N1C(=O)C(=O)C2=CC=CC=C12.[OH-].[K+]>>COC1=CC2=C(C3=CC=CC=C3N=C2C=C1)C(=O)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[C:14](=[O:17])[C:15]2=[O:16])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]([C:15](=[O:16])[OH:17])[c:18]2[cH:19]1 | COc1ccc(N2C(=O)C(=O)c3ccccc32)cc1 | COc1ccc2nc3ccccc3c(C(=O)O)c2c1 | null | null | null | Miscellaneous | OtherReaction | 7ce3db86dfbd20a18a0adb31e0150ddd0046692b095993a49b024fc4569bb129 | e3464cf1e9dfcbeb79d9b3809bd2c6c589ab22ada5d52ba3ef1df9da4d2d8a60 | c1ccc2nc3ccccc3cc2c1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7](:[c:8])-[N;H0;D3;+0:9]-1-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:4])-[c;H0;D3;+0:3]1:[c:5](:[c:6]):[c:7](:[c:8]):[n;H0;D2;+0:9]:[c:10](:[c:11]):[c;H0;D3;+0:12]:1:[c:13]:[c:14] | null | [] | null | null | 4 | HOUR | The crude N-(4-methoxyphenyl)isatin from the above was suspended in 10% aqueous potassium hydroxide (150 ml) and refluxed under a nitrogen atmosphere. After 4 hours, the reflux was stopped and the reaction was filtered while still hot. The filtrate was diluted with water (˜150 ml) and ice. This solution was then acidif... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide | Carboxylic acid | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccc2nc3ccccc3cc2c1 | c1ccc2nc3ccccc3cc2c1 | null | null | null | 4 | COc1ccc(N2C(=O)C(=O)c3ccccc32)cc1>>COc1ccc2nc3ccccc3c(C(=O)O)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c38a67482a74a60b22a9dd04f69b8a7 | BrCc1ccccc1.Oc1ccc(Br)cc1>>Brc1ccc(OCc2ccccc2)cc1 | BrC1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)Br | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[Br:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:14][cH:15]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1 | BrCc1ccccc1.Oc1ccc(Br)cc1 | Brc1ccc(OCc2ccccc2)cc1 | null | null | CC(=O)C.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | null | null | 4-Bromophenol (2 g, 0.0116 mol) in acetone (40 ml) was treated with potassium carbonate (1.91 g, 1.2 equivalents) and benzyl bromide (1.44 ml, 1.05 equivalents). The reaction was refluxed under nitrogen. After 5–6 hours of reflux, the reaction was cooled to room temperature and diluted with an equal volume of ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(=O)C.O.C(C)(=O)OCC | null | null | BrCc1ccccc1.Oc1ccc(Br)cc1>CC(=O)C.O.C(C)(=O)OCC>Brc1ccc(OCc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e3a377f9f97467ab5412975fa58ae7c | Brc1cccc(C2OCCO2)c1.O=C1Nc2ccccc2C1=O>>O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21 | BrC=1C=C(C=CC1)C1OCCO1.CO.[H-].[Na+].N1C(=O)C(=O)C2=CC=CC=C12>>O1C(OC=C1)C=1C=C(C=CC1)N1C(=O)C(=O)C2=CC=CC=C12 | Br[c:6]1[cH:7][cH:8][cH:9][c:10]([CH:11]2[O:12][CH2:13][CH2:14][O:15]2)[cH:16]1.[O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([CH:11]3[O:12][CH:13]=[CH:14][O:15]3)[cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | Brc1cccc(C2OCCO2)c1.O=C1Nc2ccccc2C1=O | O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21 | null | [Cu]I | C(Cl)(Cl)Cl.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 93f5a2c2e5e4c9b14b9bc8f83a730160c3fc67c49d749f704142771907329373 | 1d937d7149881ab21c35c386ba54ae401a9ffca81b338b7fa4a76e646bc2031b | O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]1-[#8:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[#8:8]-1):[c:9]:[c:10].[O;D1;H0:11]=[C:12]1-[c:13]:[c:14](:[c:15])-[NH;D2;+0:16]-[C:17]-1=[O;D1;H0:18]>>[O;D1;H0:11]=[C:12]1-[c:13]:[c:14](:[c:15])-[N;H0;D3;+0:16](-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]2-[#8:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-[#8:8]-2):[c:9... | null | [] | 0 | CELSIUS | 1.5 | HOUR | Isatin (3.2 g, 0.0218 mol) was dissolved in anhydrous DMF (75 ml) and cooled in an ice-bath under a nitrogen atmosphere. To this cold solution, sodium hydride (0.575 g, 0.0239 mol) was added and the reaction was stirred at 0° C. for 1.5 hours. This solution was then treated with 2-(3-bromophenyl)-1,3-dioxolane (5 g, 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Secondary amide | Ether.Ether.Tertiary amide | c1ccccc1.C1COCO1.c1ccc2c(c1)CCN2 | c1ccccc1.C1=COCO1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.C1=COCO1.c1ccc2c(c1)CC[NH]2 | HBr | [Cu]I.C(Cl)(Cl)Cl.CN(C)C=O | 0 | 1.5 | Brc1cccc(C2OCCO2)c1.O=C1Nc2ccccc2C1=O>[Cu]I.C(Cl)(Cl)Cl.CN(C)C=O>O=C1C(=O)N(c2cccc(C3OC=CO3)c2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0600565ad9de48fdad4dbd63e40730ff | O=C1NC(=O)C(Cc2ccccc2)N1.O=P(O)(O)O>>NC(=O)N[C@@H](Cc1ccccc1)C(=O)O | C1=CC=C(C=C1)CC2C(=O)NC(=O)N2.OP(=O)(O)O>>C(N)(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O | [NH:1]1[C:2](=[O:3])[NH:4][CH:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[C:13]1=[O:14].O=P(O)(O)[OH:15]>>[NH2:1][C:2](=[O:3])[NH:4][C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13](=[O:14])[OH:15] | O=C1NC(=O)C(Cc2ccccc2)N1.O=P(O)(O)O | NC(=O)N[C@@H](Cc1ccccc1)C(=O)O | null | null | null | Acylation | OtherReaction | a7932018eec3a52a9b1c995af46f98b2d2f6bd991550773506431a0ec742af9c | 41324414e6d00bf220929af228275fd3db2cf54b13006b2efe6df2d15ff13fc3 | c1ccccc1 | O-P(-O)(=O)-[OH;D1;+0:1].[O;D1;H0:2]=[C;H0;D3;+0:3]1-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[CH;D3;+0:8]-1-[C:9]-[c:10]>>[NH2;D1;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[C@@H;D3;+0:8](-[C:9]-[c:10])-[C;H0;D3;+0:3](=[O;D1;H0:2])-[OH;D1;+0:1] | null | [] | null | null | 30 | MINUTE | The assay of the D-hydantoinase activity was conducted by incubating a reaction mixture containing 120 mg/dl D-5-benzylhydantoin (BH), 50 mM KPB (pH 8.0) and an enzyme solution at 37° C. for 30 minutes, adding 9 volumes of 1.1 mMCuSO4, 11.1 mM H3PO4, centrifuging at 20,000G for 10 minutes to remove the pellet, and then... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Unsubstituted dicarboximide | Carboxylic acid.Urea | C1CNCN1 | null | c1ccccc1 | HO- | null | null | 0.5 | O=C1NC(=O)C(Cc2ccccc2)N1.O=P(O)(O)O>>NC(=O)N[C@@H](Cc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4d3555b93c149829f74e9af8dc1177c | C=COCCCl.O=C1NC(=O)c2ccccc21>>C=COCCc1cccc2c1C(=O)NC2=O | C1(C=2C(C(N1)=O)=CC=CC2)=O.[K].C(=C)OCCCl.O.NN>>C(=C)OCCC1=C2C(C(=O)NC2=O)=CC=C1 | Cl[CH2:5][CH2:4][O:3][CH:2]=[CH2:1].[cH:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[NH:14][C:15]2=[O:16]>>[CH2:1]=[CH:2][O:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12](=[O:13])[NH:14][C:15]2=[O:16] | C=COCCCl.O=C1NC(=O)c2ccccc21 | C=COCCc1cccc2c1C(=O)NC2=O | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C=O)C.C(Cl)Cl | C-C Coupling | Friedel-Crafts alkylation with halide | e62c96d80dd96a606cc3508553cba3f632c3fdc2db184e48cc240274f1e9d1be | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | O=C1NC(=O)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]=[C;D1;H2:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-1:[cH;D2;+0:13]:[c:14]:[c:15]>>[C;D1;H2:5]=[C:4]-[#8:3]-[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:12]1:[c:11]-[C:9](=[O;D1;H0:10])-[#7:8]-[C:7]-1=[O;D1;H0:6] | null | [] | 100 | CELSIUS | 6 | HOUR | Amine-containing enol ether copolymers (i.e. Poly(alkyl enolether-co-vinyloxy ethylamine) Polymers: 2-(vinyloxy)ethyl phthalimide (ImVE) was prepared by reacting 2-chloroethyl vinyl ether (25 g, 0.24 mol) with potassium phthalimide (25 g, 0.135 mol) in dimethyl foramide (75 mL) using tetra-n-butyl ammonium bromide as a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C=O)C.C(Cl)Cl | 100 | 6 | C=COCCCl.O=C1NC(=O)c2ccccc21>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C=O)C.C(Cl)Cl>C=COCCc1cccc2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-578df404b51c42d4ba39c716919cc8b2 | CCCCCCCCCCCCCCCCOCCCO.Nc1ncnc2c1ncn2CCOCP(=O)(O)O>>CCCCCCCCCCCCCCCCOCCCOP(=O)(O)COCCn1cnc2c(N)ncnc21 | C1=NC(=C2C(=N1)N(C=N2)CCOCP(=O)(O)O)N.C(CCCCCCCCCCCCCCC)OCCCO.C1CCC(CC1)N=C=NC2CCCCC2>>CCCCCCCCCCCCCCCCOCCCOP(=O)(COCCN1C=NC2=C1N=CN=C2N)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][OH:21].O[P:22](=[O:23])([OH:24])[CH2:25][O:26][CH2:27][CH2:28][n:29]1[cH:30][n:31][c:32]2[c:33]([NH2:34])[n:35][cH:36][n:37][c:38]12>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][... | CCCCCCCCCCCCCCCCOCCCO.Nc1ncnc2c1ncn2CCOCP(=O)(O)O | CCCCCCCCCCCCCCCCOCCCOP(=O)(O)COCCn1cnc2c(N)ncnc21 | null | null | N1=CC=CC=C1 | Miscellaneous | OtherReaction | f468963cd150795c559ea97eef415e4c6e817d5e41b8e41bf56e6fc6478dce9b | 0450d2d3d6169ebd913d75de6102597ba0029b73d4e4cd2ca50ccc23bda73392 | c1ncc2nc[nH]c2n1 | O-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[O;D1;H1:3])-[C:4]-[#8:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:4]-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[O;D1;H1:3])-[O;H0;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | 18 | HOUR | To a mixture of adefovir (1.36 g, 5 mmol) and 3-hexadecyloxy-1-propanol (1.8 g, 6 mmol) in dry pyridine was added DCC (2.06 g, 10 mmol). The mixture was heated to reflux and stirred 18 h then cooled and filtered. The filtrate was concentrated under reduced pressure and the residue was applied to a short column of silic... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ncnc2[nH]cnc12 | HO- | N1=CC=CC=C1 | null | 18 | CCCCCCCCCCCCCCCCOCCCO.Nc1ncnc2c1ncn2CCOCP(=O)(O)O>N1=CC=CC=C1>CCCCCCCCCCCCCCCCOCCCOP(=O)(O)COCCn1cnc2c(N)ncnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0cafb7267e3a476788662141fc2d8f29 | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O>>Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O | [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C(=O)NC(=O)C(=C1)C)OCCON(C)C)O.F.F.F.C(C)N(CC)CC.C(C)N(CC)CC.CO>>CN(OCCO[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C(=O)NC(=O)C(=C1)C)C | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:9][CH2:8][C@H:7]1[O:6][C@@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:23](=[O:24])[nH:22][c:20]2=[O:21])[C@H:12]([O:13][CH2:14][CH2:15][O:16][N:17]([CH3:18])[CH3:19])[C@@H:10]1[OH:11]>>[CH3:1][c:2]1[cH:3][n:4]([C@@H:5]2[O:6][C@H:7]([CH2:8][OH:9])[C@@H:10]([OH:11])[C@H:12]2[O:13][CH2:14][CH2:15]... | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O | Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O | null | null | C1CCOC1.C(Cl)Cl | Deprotection | Alcohol deprotection from silyl ethers | 5607047bc82bb27c5a65769b01ea0774767f4428c871f65da0b6352111d7a6e9 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#8:4])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 92.5 | [{"value": 92.5, "product": "CN(OCCO[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C(=O)NC(=O)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.4, "product": "CN(OCCO[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C(=O)NC(=O)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1 | null | c1cncnc1.C1CCOC1 | Other | C1CCOC1.C(Cl)Cl | null | 24 | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O>C1CCOC1.C(Cl)Cl>Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27b58087e3844fdf8b955fa933d6ceab | CCC(=O)c1cccc(Cl)c1.[Br-]>>CC(Br)C(=O)c1cccc(Cl)c1 | ClC=1C=C(C=CC1)C(CC)=O.[Br-].[Br-].O1CCOCC1.N1(CCOCC1)O.CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C.Cl>>BrC(C(=O)C1=CC(=CC=C1)Cl)C | [CH3:1][CH2:2][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1.[Br-:3]>>[CH3:1][CH:2]([Br:3])[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1 | CCC(=O)c1cccc(Cl)c1.[Br-] | CC(Br)C(=O)c1cccc(Cl)c1 | null | null | O.O1CCOCC1 | Functional Group Interconversion | Bromination | c4e4001f7df68217305f4e3df4c72011ad7e2bce5a268f8554ebe23f061baf28 | fe149a07f370bdd2ea40b2dff4f3462711fb34a60b8733c443efdeb5ab4d5c53 | c1ccccc1 | [Br-;H0;D0:1].[C;D1;H3:2]-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]>>[Br;H0;D1;+0:1]-[CH;D3;+0:3](-[C;D1;H3:2])-[C:4](=[O;D1;H0:5])-[c:6] | 85 | [{"value": 85.0, "product": "BrC(C(=O)C1=CC(=CC=C1)Cl)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The racemate of the morpholinol metabolite of bupropion hydrochloride ((+/−)-(2R*,3R*)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride) may be synthesized by the following process. To 3′-chloropropiophenone (10.0 g, 0.06 mol) in dioxane (50 mL) was added a solution of dioxane dibromide (14.9 g, 0.06 mol)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary halide | null | null | c1ccccc1 | null | O.O1CCOCC1 | null | 2 | CCC(=O)c1cccc(Cl)c1.[Br-]>O.O1CCOCC1>CC(Br)C(=O)c1cccc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d55caad6b3ba44ea8fbfd252d937eada | CC(Br)C(=O)c1cccc(Cl)c1.CC(C)(N)CO>>C[C@H]1NC(C)(C)CO[C@]1(O)c1cccc(Cl)c1 | BrC(C(=O)C1=CC(=CC=C1)Cl)C.NC(CO)(C)C>>ClC=1C=C(C=CC1)[C@@]1([C@H](NC(CO1)(C)C)C)O | Br[CH:2]([CH3:1])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1.[NH2:3][C:4]([CH3:5])([CH3:6])[CH2:7][OH:8]>>[CH3:1][C@H:2]1[NH:3][C:4]([CH3:5])([CH3:6])[CH2:7][O:8][C@:9]1([OH:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1 | CC(Br)C(=O)c1cccc(Cl)c1.CC(C)(N)CO | C[C@H]1NC(C)(C)CO[C@]1(O)c1cccc(Cl)c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | b509ec51bcd651e93ed0f185bf10ca72590b708c09c767be3c11a2d10398c2d6 | d174e740e497dbea85dd778938d93b1551a7b01ef9268cd3ba86b3559a5a4a0c | c1ccc(C2CNCCO2)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[NH2;D1;+0:11])-[C:12]-[OH;D1;+0:13]>>[C;D1;H3:2]-[C@H;D3;+0:1]1-[NH;D2;+0:11]-[C:9](-[C;D1;H3:8])(-[C;D1;H3:10])-[C:12]-[O;H0;D2;+0:13]-[C@;H0;D4;+0:3]-1(-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | 75 | [{"value": 75.0, "product": "ClC=1C=C(C=CC1)[C@@]1([C@H](NC(CO1)(C)C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "ClC=1C=C(C=CC1)[C@@]1([C@H](NC(CO1)(C)C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 2-bromo-3′-chloropropiophenone (19.3 g, 0.08 mol) in MeOH (100 mL) was added dropwise a solution of 2-amino-2-methyl-1-propanol (27.8 g, 0.31 mol) in methanol (200 mL) at ambient temperature. The mixture was stirred for 18 h and concentrated in vacuo. The residue was partitioned between water and dieth... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Primary alcohol.Primary amine | Ether.Tertiary alcohol.Secondary amine | null | C1COCCN1 | C1COCCN1.c1ccccc1 | HBr | CO | null | 18 | CC(Br)C(=O)c1cccc(Cl)c1.CC(C)(N)CO>CO>C[C@H]1NC(C)(C)CO[C@]1(O)c1cccc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-171d418044a4472297102e1e9fd895e3 | CCOC1=CC(=O)CCC1.[Br][Mg][c]1ccccc1>>O=C1C=C(c2ccccc2)CCC1 | Cl.C(C)OC1=CC(CCC1)=O.C1(=CC=CC=C1)[Mg]Br>>C1(=CC=CC=C1)C1=CC(CCC1)=O | CCO[C:4]1=[CH:3][C:2](=[O:1])[CH2:13][CH2:12][CH2:11]1.[Br][Mg][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]1[CH:3]=[C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][CH2:13]1 | CCOC1=CC(=O)CCC1.[Br][Mg][c]1ccccc1 | O=C1C=C(c2ccccc2)CCC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 533855bcf25ac7a90be114df3910e2c24f9f19983e33b96616958cf4dad453c7 | d40970f17bb42dabc39bca313882d788a234a292f4219978b608ad1911b3aef8 | O=C1C=C(c2ccccc2)CCC1 | C-C-O-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1.[Br]-[Mg]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[O;D1;H0:4]=[C:3]1-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])=[C:2]-1 | null | [] | null | null | 1 | HOUR | At 0° C., 3-ethoxycyclohex-2-enone (2 g, 14.3 mmol) in THF (2 mL) was added phenylmagnesium bromide (1.0 M solution in THF, 15.0 mL) slowly. After the addition, the reaction mixture was warmed up to room temperature and stirred for 1 hr. Then 1N HCl solution (15.16 mL) was added to quench the reaction and the organic l... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ether | null | C1=CCCCC1.c1ccccc1 | C1=CCCCC1.c1ccccc1 | C1=CCCCC1.c1ccccc1 | HBr.Mg | C1CCOC1 | null | 1 | CCOC1=CC(=O)CCC1.[Br][Mg][c]1ccccc1>C1CCOC1>O=C1C=C(c2ccccc2)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-252ad776d6b649efaee5e0abcd5fe44a | O=C1C=C(c2ccccc2)CCC1.[C-]#N>>N#CC1(c2ccccc2)CCCC(=O)C1 | C1(=CC=CC=C1)C1=CC(CCC1)=O.[C-]#N.[K+].Cl.CN(C)C.C([O-])(O)=O.[Na+]>>O=C1CC(CCC1)(C#N)C1=CC=CC=C1 | [C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)=[CH:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10]1.[N:1]#[C-:2]>>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][CH2:12][C:13](=[O:14])[CH2:15]1 | O=C1C=C(c2ccccc2)CCC1.[C-]#N | N#CC1(c2ccccc2)CCCC(=O)C1 | null | null | O.CN(C)C=O | C-C Coupling | OtherReaction | ee9e7e4e4f7950f93fdeea77670480c36599c80a03abb2c2e00a8087ccff4dee | 491da00d5858e1f2efb2cb52ad5e0bdc63f42de65d8d378a501175351ff676a5 | O=C1CCCC(c2ccccc2)C1 | [C-;H0;D1:1]#[N;D1;H0:2].[O;D1;H0:3]=[C:4]1-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])=[CH;D2;+0:12]-1>>[N;D1;H0:2]#[C;H0;D2;+0:1]-[C;H0;D4;+0:8]1(-[c:9](:[c:10]):[c:11])-[C:7]-[C:6]-[C:5]-[C:4](=[O;D1;H0:3])-[CH2;D2;+0:12]-1 | 92 | [{"value": 92.0, "product": "O=C1CC(CCC1)(C#N)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 93 | CELSIUS | null | null | A mixture of 3-phenylcyclohex-2-enone (14.3 mmol), potassium cyanide (1.92 g) and trimethylamine hydrochloride (2.06 g, 21.5 mmol) in H2O (10 mL) and DMF (57 mL) was heated at 93° C. for 6 hr. After cooling down to room temperature, saturated sodium bicarbonate was added and the organic layer was separated. The aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Nitrile | C1=CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | null | O.CN(C)C=O | 93 | null | O=C1C=C(c2ccccc2)CCC1.[C-]#N>O.CN(C)C=O>N#CC1(c2ccccc2)CCCC(=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41317c7bf9bf4f5cb8d294b70d2cc084 | N#CC1(c2ccccc2)CCCC(=O)C1.OCCO>>N#CC1(c2ccccc2)CCCC2(C1)OCCO2 | O=C1CC(CCC1)(C#N)C1=CC=CC=C1.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>C1OC2(CC(CCC2)(C#N)C2=CC=CC=C2)OC1 | [N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][CH2:12][C:13](=[O:15])[CH2:14]1.O[CH2:16][CH2:17][OH:18]>>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][CH2:12][C:13]2([CH2:14]1)[O:15][CH2:16][CH2:17][O:18]2 | N#CC1(c2ccccc2)CCCC(=O)C1.OCCO | N#CC1(c2ccccc2)CCCC2(C1)OCCO2 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 87830b95e8a201d62318c70ccec6a054912fe58024d4e2b4b3794a96ad0f84ae | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | c1ccc(C2CCCC3(C2)OCCO3)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[C:9]>>[C:4]-[C:5]-[C;H0;D4;+0:6]1(-[C:8]-[C:9])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1 | 48 | [{"value": 48.0, "product": "C1OC2(CC(CCC2)(C#N)C2=CC=CC=C2)OC1", "details": "PERCENTYIELD", "is_desired": false}] | 111 | CELSIUS | 8 | HOUR | The mixture of 3-oxo-1-phenylcyclohexanecarbonitrile (2.62 g), ethylene glycol (3.65 mL) and pyridinium p-toluene sulfonate (1 spatula) in benzene (40 mL) was stirred at 111° C. with Dean-Stark apparatus overnight. After cooling down to room temperature, the mixture was washed with saturated sodium bicarbonate and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | C1CCCCC1 | C1CCC2(CC1)OCCO2 | c1ccccc1.C1CCC2(CC1)OCCO2 | HO- | C1=CC=CC=C1 | 111 | 8 | N#CC1(c2ccccc2)CCCC(=O)C1.OCCO>C1=CC=CC=C1>N#CC1(c2ccccc2)CCCC2(C1)OCCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11d6b4e2d7e343d0996c130ebd1192a0 | N#CC1(c2ccccc2)CCC2OCCOC2C1>>O=CC1(c2ccccc2)CCCC2(C1)OCCO2 | C([O-])(O)=O.[Na+].Cl.C1OC2CC(CCC2OC1)(C#N)C1=CC=CC=C1.CC(C)C[AlH]CC(C)C>>C1OC2(CC(CCC2)(C=O)C2=CC=CC=C2)OC1 | N#[C:2][C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][CH:12]2[CH:13]([CH2:14]1)[O:18][CH2:17][CH2:16][O:15]2>>[O:1]=[CH:2][C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][CH2:12][C:13]2([CH2:14]1)[O:15][CH2:16][CH2:17][O:18]2 | N#CC1(c2ccccc2)CCC2OCCOC2C1 | O=CC1(c2ccccc2)CCCC2(C1)OCCO2 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | ea5c713695bfdde5db79544569d959eb31e0b73808683a348b07a9fb1ab0806a | dcffb0529c0841166f9e210fcd803426c1c51001841f94e426771dac8ca54349 | c1ccc(C2CCCC3(C2)OCCO3)cc1 | N#[C;H0;D2;+0:1]-[C:2]1(-[c:3])-[C:4]-[C:5]-[CH;D3;+0:6]2-[O;H0;D2;+0:7]-[C:8]-[C:9]-[#8:10]-[CH;D3;+0:11]-2-[C:12]-1>>[O;D1;H0:13]=[CH;D2;+0:1]-[C:2]1(-[c:3])-[C:4]-[C:5]-[CH2;D2;+0:6]-[C;H0;D4;+0:11]2(-[#8:10]-[C:9]-[C:8]-[O;H0;D2;+0:7]-2)-[C:12]-1 | 85 | [{"value": 85.0, "product": "C1OC2(CC(CCC2)(C=O)C2=CC=CC=C2)OC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | At −78° C., 3-ethylenedioxy-1-phenylcyclohexanecarbonitrile (1.66 g, 6.83 mmol) in toluene (20 mL) was added DIBAL-H (1.0 M solution in toluene, 8.88 mL) slowly and was stirred for 1 hr. The reaction mixture was warmed up to room temperature and was added 1N HCl solution (2.60 mL) and was stirred for 1 hr. Saturated so... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitrile | Aldehyde.Ether.Ether | C1CCC2OCCOC2C1 | C1CCC2(CC1)OCCO2 | c1ccccc1.C1CCC2(CC1)OCCO2 | null | C1(=CC=CC=C1)C | null | 1 | N#CC1(c2ccccc2)CCC2OCCOC2C1>C1(=CC=CC=C1)C>O=CC1(c2ccccc2)CCCC2(C1)OCCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9407348f39345a99bf82818614ddce5 | CC1C2(CCCC1(C=O)c1ccccc1)OCCO2>>OCC1(c2ccccc2)CCCC2(C1)OCCO2 | CC1C(CCCC12OCCO2)(C=O)C2=CC=CC=C2.[BH4-].[Na+]>>C1OC2(CC(CCC2)(C2=CC=CC=C2)CO)OC1 | C[CH:14]1[C:3]([CH:2]=[O:1])([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][CH2:12][C:13]12[O:15][CH2:16][CH2:17][O:18]2>>[OH:1][CH2:2][C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][CH2:12][C:13]2([CH2:14]1)[O:15][CH2:16][CH2:17][O:18]2 | CC1C2(CCCC1(C=O)c1ccccc1)OCCO2 | OCC1(c2ccccc2)CCCC2(C1)OCCO2 | null | null | CO | Miscellaneous | OtherReaction | b3e84632f74a4ec28268cff09540b6480e4d5d1b36fe8eadb1bea830cb1b4415 | 43cf4997d6e2488d8c69ca8bc684124ace6515563d3e08dcc47ef2a56dd17cc0 | c1ccc(C2CCCC3(C2)OCCO3)cc1 | C-[CH;D3;+0:1](-[C:2]1(-[C:3])-[#8:4]-[C:5]-[C:6]-[#8:7]-1)-[C:8](-[c:9])(-[CH;D2;+0:10]=[O;H0;D1;+0:11])-[C:12]>>[C:12]-[C:8](-[c:9])(-[CH2;D2;+0:10]-[OH;D1;+0:11])-[CH2;D2;+0:1]-[C:2]1(-[C:3])-[#8:4]-[C:5]-[C:6]-[#8:7]-1 | 87 | [{"value": 87.0, "product": "C1OC2(CC(CCC2)(C2=CC=CC=C2)CO)OC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.6, "product": "C1OC2(CC(CCC2)(C2=CC=CC=C2)CO)OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of methyl 3,3-ethylenedioxy-1-phenylcyclohexanecarbaldehyde (1.43 g, 5.81 mmol) in methanol (25 mL) at 0° C. was added sodium borohydride (221 mg) in portions, and the resulting suspension was stirred at room temperature overnight. The reaction was quenched with saturated sodium bicarbonate and methanol w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | c1ccccc1.C1CCC2(CC1)OCCO2 | Other | CO | null | 8 | CC1C2(CCCC1(C=O)c1ccccc1)OCCO2>CO>OCC1(c2ccccc2)CCCC2(C1)OCCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85e3a2687cd244519163a64ff49e61c4 | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCC3(C2)OCCO3)cc(C(F)(F)F)c1>>O=C1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)C1 | C([O-])(O)=O.[Na+].ClCCl.C1OC2(CC(CCC2)(C2=CC=CC=C2)COCC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)OC1.Cl>>FC(C=1C=C(COCC2(CC(CCC2)=O)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][CH2:5][C:6]([CH2:7][O:8][CH2:9][c:10]1[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]1)([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH2:30]2>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][C:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11][c:12]([C:13]([F:14])([F:1... | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCC3(C2)OCCO3)cc(C(F)(F)F)c1 | O=C1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)C1 | null | null | CC(=O)C | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCCC(COCc2ccccc2)(c2ccccc2)C1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | 92.3 | [{"value": 92.0, "product": "FC(C=1C=C(COCC2(CC(CCC2)=O)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "FC(C=1C=C(COCC2(CC(CCC2)=O)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1-(((3,3-ethylenedioxy-1-phenylcyclohexyl)methoxy)methyl)-3,5-bis(trifluoromethyl)benzene (990 mg, 2.09 mmol) in acetone (4 mL) at room temperature were added 1N HCl solution (3.13 mL) and the resulting mixture was stirred at reflux for 2 hr. After cooling down, saturated sodium bicarbonate and dichlor... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | C1CCCCC1.c1ccccc1.c1ccccc1 | HO- | CC(=O)C | null | null | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCC3(C2)OCCO3)cc(C(F)(F)F)c1>CC(=O)C>O=C1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f97e407b89e84fd9945ecbbef00955b6 | O=C1CC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CCCN1>>FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1 | FC(C=1C=C(COCC2(CC(NCCC2)=O)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F>>FC(C=1C=C(COCC2(CCNCCC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F | O=[C:22]1[NH:21][CH2:20][CH2:19][CH2:18][C:11]([CH2:10][O:9][CH2:8][c:7]2[cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:30][c:25]([C:26]([F:27])([F:28])[F:29])[cH:24]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:23]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][CH2:10][C:11]2([c:12]3[cH:13][cH:14][cH:15][cH:... | O=C1CC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CCCN1 | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1 | null | null | C(C)OCC | Reduction | Reduction of secondary amides to amines | a76e26501478492bb816aa38270aa626822e461354a50020ad385e42ae7fa756 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(COCC2(c3ccccc3)CCCNCC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[C:3] | null | [] | 65 | CELSIUS | 1 | HOUR | The mixture of Isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepan-2-one (90 mg, 0.20 mmol) in borone.THF complex solution (1.5 M in diethyl ether, 1.08 mL) was stirred at room temperature overnight and then at 65° C. for 1 hr. After cooling down, the mixture was concentrated under vacuum and metha... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1CCCNCC1 | C1CCCNCC1 | c1ccccc1.c1ccccc1.C1CCCNCC1 | Other | C(C)OCC | 65 | 1 | O=C1CC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CCCN1>C(C)OCC>FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c45a7a9c1bb48d9913c24128571cdaf | C=O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>>CN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | FC(C=1C=C(COCC2(CCNCCC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F.C=O.C(=O)O>>FC(C=1C=C(COCC2(CCN(CCC2)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][CH2:5][C:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]2)([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11][c:12]([C:13]([F:1... | C=O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1 | CN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | b08f9797f972874990f9efa29640dafa98a4e6636d62a3ea5b594947c4ef7ed8 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(COCC2(c3ccccc3)CCCNCC2)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | 67 | [{"value": 67.0, "product": "FC(C=1C=C(COCC2(CCN(CCC2)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.6, "product": "FC(C=1C=C(COCC2(CCN(CCC2)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 8 | HOUR | The mixture of Isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg), paraformaldehyde (3 mg) and formic acid (2.2 mg) in chloroform (0.1 mL) was stirred at 65° C. for overnight. After cooling down, the mixture was concentrated under vacuum and filtered through anion exchange cartridge to get... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1.c1ccccc1 | Other | C(Cl)(Cl)Cl | 65 | 8 | C=O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>C(Cl)(Cl)Cl>CN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a45246cc5f84d0cb90ea4bcf20c2b8c | CC(=O)O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>>CCN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | FC(C=1C=C(COCC2(CCNCCC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F.[BH4-].[Na+].C(C)(=O)O>>FC(C=1C=C(COCC2(CCN(CCC2)CC)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F | O=[C:2](O)[CH3:1].[NH:3]1[CH2:4][CH2:5][CH2:6][C:7]([CH2:8][O:9][CH2:10][c:11]2[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]2)([c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][C:7]([CH2:8][O:9][CH2:10][c:11]2[cH:12][... | CC(=O)O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1 | CCN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3c60de4847eea4bb797568ef1c3322e89351896e4db1746c887f1df86bc53ccb | 5fb52ddc67e52a472f28d69e60f3ac94989e70b5307ac3fa95fe53e87c1d2696 | c1ccc(COCC2(c3ccccc3)CCCNCC2)cc1 | O-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:6]-[C:7] | 56 | [{"value": 56.0, "product": "FC(C=1C=C(COCC2(CCN(CCC2)CC)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg), in glacial acetic acid (0.05 mL) was added sodium borohydride (2 mg) in two portions. After addition, the mixture was stirred at room temperature for overnight. The mixture was concentrated under vacuum. Then saturated sodium bicarbonate ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amine | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1.c1ccccc1 | Other | null | null | 8 | CC(=O)O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>>CCN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-063a518b9b59485c8f6e95e9593b3357 | CCN1CCCC(CCOCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>>CCN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | FC(C=1C=C(COCCC2(CCN(CCC2)CC)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F.FC(C=1C=C(COCC2(CCNCCC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F>>FC(C=1C=C(COCC2(CCN(CCC2)CC)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F | FC(F)(F)c1cc(COC[CH2:8][C:7]2([c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[CH2:6][CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:32][CH2:31]2)cc(C(F)(F)F)c1.c1ccc(C2(C[O:9][CH2:10][c:11]3[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]3)CCCNCC2)cc1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5... | CCN1CCCC(CCOCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1 | CCN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ea3ea856acc4828df846817b3921946d16629db41029456a067cf54ba0f14aaa | 820e1fcaf1e9815d6fcbf81186f53aee1cc2efc4c63a06b5c19417978392de23 | c1ccc(COCC2(c3ccccc3)CCCNCC2)cc1 | F-C(-F)(-F)-c1:c:c(-C-O-C-[CH2;D2;+0:1]-[C:2](-[c:3])(-[C:4])-[C:5]):c:c(-C(-F)(-F)-F):c:1.[c:6]-[C:7]-[O;H0;D2;+0:8]-C-C1(-c2:c:c:c:c:c:2)-C-C-C-N-C-C-1>>[C:4]-[C:2](-[c:3])(-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[C:7]-[c:6])-[C:5] | 62 | [{"value": 62.0, "product": "FC(C=1C=C(COCC2(CCN(CCC2)CC)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Isomer B of 4-((3,5-bis(trifluoromethyl)benzyloxy)ethyl)-1-ethyl-4-phenylazepane was made from Isomer B of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane in the same manner as described above to give the product as a clear sticky oil (2 mg, 62% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Trifluoro group.Ether.Ether.Secondary amine | Ether | c1ccccc1.c1ccccc1.C1CCCNCC1 | null | C1CCC[NH]CC1.c1ccccc1.c1ccccc1 | HF | null | null | null | CCN1CCCC(CCOCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>>CCN1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55ba5bde656147629274f122dc38c215 | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1.O=CC1CC1>>FC(F)(F)c1cc(COCC2(c3ccccc3)CCCN(CC3CC3)CC2)cc(C(F)(F)F)c1 | FC(C=1C=C(COCC2(CCNCCC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F.C1(CC1)C=O.C(#N)[BH3-].[Na+]>>FC(C=1C=C(COCC2(CCN(CCC2)CC2CC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F | [F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][CH2:10][C:11]2([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18][CH2:19][CH2:20][NH:21][CH2:26][CH2:27]2)[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]1.O=[CH:22][CH:23]1[CH2:24][CH2:25]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][CH2:10][C:11]2... | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1.O=CC1CC1 | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCN(CC3CC3)CC2)cc(C(F)(F)F)c1 | null | FC(C(=O)O)(F)F | CO | Heteroatom Alkylation and Arylation | reductive amination | 12ef0d68a332972a959e884007c636a69fc775b16af027831e7d60fec7fb61bb | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(COCC2(c3ccccc3)CCCN(CC3CC3)CC2)cc1 | O=[CH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1)-[C:8]-[C:9] | 41.5 | [{"value": 41.0, "product": "FC(C=1C=C(COCC2(CCN(CCC2)CC2CC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.5, "product": "FC(C=1C=C(COCC2(CCN(CCC2)CC2CC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | Mixture of isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg) and cyclopropanecarbaldehyde (1.4 mg) in methanol (0.15 mL) was stirred at room temperature for 0.5 hr, then sodium cyanoborohydride (1.0 M solution in THF, 0.02 mL) was added followed by 1 drop of trifluoroacetic acid. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCCNCC1 | C1CCC[NH]CC1 | c1ccccc1.c1ccccc1.C1CCC[NH]CC1.C1CC1 | Other | FC(C(=O)O)(F)F.CO | null | 0.5 | FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1.O=CC1CC1>FC(C(=O)O)(F)F.CO>FC(F)(F)c1cc(COCC2(c3ccccc3)CCCN(CC3CC3)CC2)cc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9a402b306ff49baa560b3a2cd76a8ad | CC(C)=O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>>CC(C)N1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | FC(C=1C=C(COCC2(CCNCCC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F.CC(=O)C.C(#N)[BH3-].[Na+]>>FC(C=1C=C(COCC2(CCN(CCC2)C(C)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F | O=[C:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH2:6][CH2:7][C:8]([CH2:9][O:10][CH2:11][c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]2)([c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:32][CH2:33]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH2:7][C:8]([CH2:9][O:10][CH2:11... | CC(C)=O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1 | CC(C)N1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 | null | FC(C(=O)O)(F)F | CO | Heteroatom Alkylation and Arylation | reductive amination | 7dc8497912f406c4e17dac031f00821c0222f9ff062f52522f26c91253787644 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(COCC2(c3ccccc3)CCCNCC2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:7]-[C:8] | 76 | [{"value": 76.0, "product": "FC(C=1C=C(COCC2(CCN(CCC2)C(C)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "FC(C=1C=C(COCC2(CCN(CCC2)C(C)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | Mixture of isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg) and acetone (1.2 mg) in methanol (0.15 mL) was stirred at room temperature for 0.5 hr, then sodium cyanoborohydride (1.0 M solution in THF, 0.02 mL) was added followed by 1 drop of trifluoroacetic acid. The mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1.c1ccccc1 | Other | FC(C(=O)O)(F)F.CO | null | 0.5 | CC(C)=O.FC(F)(F)c1cc(COCC2(c3ccccc3)CCCNCC2)cc(C(F)(F)F)c1>FC(C(=O)O)(F)F.CO>CC(C)N1CCCC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)(c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-340bd4cb505843e790e3606da1ccd98b | CO.Cn1cc(C[C@@H](N)C(=O)O)c2ccccc21.O=S(Cl)Cl>>COC(=O)[C@H](N)Cc1cn(C)c2ccccc12.Cl | S(=O)(Cl)Cl.CN1C=C(C[C@@H](N)C(=O)O)C2=CC=CC=C12.CO>>Cl.COC([C@H](N)CC1=CN(C2=CC=CC=C12)C)=O | [CH3:1][OH:2].O[C:3](=[O:4])[C@H:5]([NH2:6])[CH2:7][c:8]1[cH:9][n:10]([CH3:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12.O=S(Cl)[Cl:18]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([NH2:6])[CH2:7][c:8]1[cH:9][n:10]([CH3:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12.[ClH:18] | CO.Cn1cc(C[C@@H](N)C(=O)O)c2ccccc21.O=S(Cl)Cl | COC(=O)[C@H](N)Cc1cn(C)c2ccccc12.Cl | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc2[nH]ccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[N;D1;H2:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[C:5]-[C:4](-[N;D1;H2:6])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:8]-[C;D1;H3:7].[ClH;D0;+0:1] | null | [] | null | null | 20 | HOUR | Thionyl chloride (1.3 mL, 18.4 mmol) was added dropwise to a suspension of 1-methyl-D-tryptophan (2.0 g, 9.2 mmol) in MeOH (30 mL) at 0° C. under a nitrogen blanket. The resulting mixture was warmed slowly to room temperature and stirred for a total of 20 hours. The solvent was removed under reduced pressure and tritur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1c[nH]c2ccccc12 | HCl | null | null | 20 | CO.Cn1cc(C[C@@H](N)C(=O)O)c2ccccc21.O=S(Cl)Cl>>COC(=O)[C@H](N)Cc1cn(C)c2ccccc12.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-60599b28a97246d789c0834951f8bbc5 | Clc1ccc(Cl)nn1.O=C(O)C1CCC1>>Clc1cc(C2CCC2)c(Cl)nn1 | S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+].S(O)(O)(=O)=O.ClC=1N=NC(=CC1)Cl.N.C1(CCC1)C(=O)O>>ClC=1N=NC(=CC1C1CCC1)Cl | [Cl:1][c:2]1[cH:3][cH:4][c:9]([Cl:10])[n:11][n:12]1.O=C(O)[CH:5]1[CH2:6][CH2:7][CH2:8]1>>[Cl:1][c:2]1[cH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8]2)[c:9]([Cl:10])[n:11][n:12]1 | Clc1ccc(Cl)nn1.O=C(O)C1CCC1 | Clc1cc(C2CCC2)c(Cl)nn1 | null | [N+](=O)([O-])[O-].[Ag+] | O | C-C Coupling | OtherReaction | 76ea7cc66280bd5591cff3dd86dc4f23071be46a2a9e2e733495062a762bb1cd | f96cdbfbd3979fc19377157a3b073c6b979862e16c815ce1feb7d13f6831561f | c1cc(C2CCC2)cnn1 | O-C(=O)-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1.[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[#7;a:8]:[c:9](-[Cl;D1;H0:10]):[c:11]:[cH;D2;+0:12]:1>>[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[#7;a:8]:[c:9](-[Cl;D1;H0:10]):[c:11]:[c;H0;D3;+0:12]:1-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1 | 82 | [{"value": 82.0, "product": "ClC=1N=NC(=CC1C1CCC1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "ClC=1N=NC(=CC1C1CCC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 5 | MINUTE | Concentrated sulphuric acid (53.6 ml, 1.0 mol) was added carefully to a stirred suspension of 3,6-dichloropyridazine (50.0 g, 0.34 mol) in water (1.25 l). This mixture was then heated to 70° C. (internal temperature) before the addition of cyclobutane carboxylic acid (35.3 ml, 0.37 mol). A solution of silver nitrate (1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccnnc1.C1CCC1 | c1ccnnc1.C1CCC1 | c1ccnnc1.C1CCC1 | HO- | [N+](=O)([O-])[O-].[Ag+].O | 70 | 0.083333 | Clc1ccc(Cl)nn1.O=C(O)C1CCC1>[N+](=O)([O-])[O-].[Ag+].O>Clc1cc(C2CCC2)c(Cl)nn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26548357d3fb4ca6b89c4b2d9219dad3 | Clc1cc(C2CCC2)c(Cl)nn1.NNC(=O)c1ccccc1>>Clc1nn2c(-c3ccccc3)nnc2cc1C1CCC1 | ClC=1N=NC(=CC1C1CCC1)Cl.C(C1=CC=CC=C1)(=O)NN.Cl.C(C)N(CC)CC>>ClC=1C(=CC=2N(N1)C(=NN2)C2=CC=CC=C2)C2CCC2 | Cl[c:14]1[n:4][n:3][c:2]([Cl:1])[c:16]([CH:17]2[CH2:18][CH2:19][CH2:20]2)[cH:15]1.O=[C:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][NH2:13]>>[Cl:1][c:2]1[n:3][n:4]2[c:5](-[c:6]3[cH:7][cH:8][cH:9][cH:10][cH:11]3)[n:12][n:13][c:14]2[cH:15][c:16]1[CH:17]1[CH2:18][CH2:19][CH2:20]1 | Clc1cc(C2CCC2)c(Cl)nn1.NNC(=O)c1ccccc1 | Clc1nn2c(-c3ccccc3)nnc2cc1C1CCC1 | null | null | CC=1C=CC(=CC1)C | Aromatic Heterocycle Formation | OtherReaction | 79ddefd422ebc8c345a9ef0f4da625e92f8efa9b906e7813129e2a0f01aacc3f | 15eece34175da314702a52f60efb76be180411dc7b9ff57dc38c1e1c5f1072c8 | c1ccc(-c2nnc3cc(C4CCC4)cnn23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[n;H0;D2;+0:6]:1.O=[C;H0;D3;+0:7](-[NH;D2;+0:8]-[NH2;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[n;H0;D2;+0:9]:[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[n;H0;D3;+0:6]:2:1):[c:13]:[c:14] | 34 | [{"value": 34.0, "product": "ClC=1C(=CC=2N(N1)C(=NN2)C2=CC=CC=C2)C2CCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,6-dichloro-4-cyclobutylpyridazine from above (55.7 g, 0.27 mol), benzoic hydrazide (41.1 g, 0.30 mol) and triethylamine hydrochloride (41.5 g, 0.30 mol) in p-xylene (0.4 l) was stirred and heated at reflux under a stream of nitrogen for 24 hours. Upon cooling the volatiles were removed in vacuo. The resi... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aromatic halide | null | c1ccnnc1 | c1cnn2cnnc2c1 | c1ccccc1.c1cnn2cnnc2c1.C1CCC1 | HCl | CC=1C=CC(=CC1)C | null | null | Clc1cc(C2CCC2)c(Cl)nn1.NNC(=O)c1ccccc1>CC=1C=CC(=CC1)C>Clc1nn2c(-c3ccccc3)nnc2cc1C1CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9fa064f3e1f3429d9c2af7fa8d1def04 | CN(C)CC(C)(C)CN.Clc1nn2c(-c3ccccc3)nnc2cc1C1CCC1>>CN(C)CC(C)(C)CNc1nn2c(-c3ccccc3)nnc2cc1C1CCC1 | ClC=1C(=CC=2N(N1)C(=NN2)C2=CC=CC=C2)C2CCC2.CN(CC(CN)(C)C)C>>C1(CCC1)C1=CC=2N(N=C1NCC(CN(C)C)(C)C)C(=NN2)C2=CC=CC=C2 | [CH3:1][N:2]([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH2:9].Cl[c:10]1[n:11][n:12]2[c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[n:20][n:21][c:22]2[cH:23][c:24]1[CH:25]1[CH2:26][CH2:27][CH2:28]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[CH2:8][NH:9][c:10]1[n:11][n:12]2[c:13](-[c:14]3[cH:15][cH:16... | CN(C)CC(C)(C)CN.Clc1nn2c(-c3ccccc3)nnc2cc1C1CCC1 | CN(C)CC(C)(C)CNc1nn2c(-c3ccccc3)nnc2cc1C1CCC1 | null | null | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 0e9d44a418934ea3b35a3d9445e3714842206ef5d6205c04162d300e73d21050 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2nnc3cc(C4CCC4)cnn23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4]:[#7;a:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1-[C:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:10]-[c:9]1:[c:8]:[c:7]2:[#7;a:6]:[#7;a:5]:[c:4]:[#7;a:3]:2:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C:11] | null | [] | null | null | null | null | 6-Chloro-7-cyclobutyl-3-phenyl-[1,2,4]triazolo[4,3-b]pyridazine (100 mg) and N,N,2,2-tetramethyl-1,3-propanediamine (2 ml) were heated together in a sealed tube at 70° C. for 16 hours. Cooled and water (5 ml) added. Precipitate filtered, washed (water, ether) and dried. 1H NMR (250 MHz, DMSO) δ 1.20 (6H, s), 2.10 (1H, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnn2cnnc2c1 | c1cnn2cnnc2c1 | c1ccccc1.c1cnn2cnnc2c1.C1CCC1 | HCl | O | null | null | CN(C)CC(C)(C)CN.Clc1nn2c(-c3ccccc3)nnc2cc1C1CCC1>O>CN(C)CC(C)(C)CNc1nn2c(-c3ccccc3)nnc2cc1C1CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70419371049d4118a56e44f216f0f529 | C1CCOC1.[C-]#N>>C1CCN(N2CCCCC2)CC1 | C[Mg+].[Br-].C1CCOC1.[C-]#N>>N1(CCCCC1)N1CCCCC1 | O1[CH2:6][CH2:7][CH2:8][CH2:9]1.[C-:1]#[N:4]>>[CH2:1]1[CH2:2][CH2:3][N:4]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:11][CH2:12]1 | C1CCOC1.[C-]#N | C1CCN(N2CCCCC2)CC1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 9600a9cdded5511790358526068404cbecb05dc975e3e20b9e9c495fb2a6c36a | 6cd3a1be197917c19b234e2654f9156c137b6cde288d4b64eaca612bd8f3872f | C1CCN(N2CCCCC2)CC1 | O1-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1.[C-;H0;D1:5]#[N;H0;D1;+0:6]>>[C:7]1-[CH2;D2;+0:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[#7:8]-1-[N;H0;D3;+0:6]1-[C:9]-[C:10]-[CH2;D2;+0:5]-[C:11]-[C:12]-1 | 79 | [{"value": 79.0, "product": "N1(CCCCC1)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 18 | HOUR | The cyanide (4.87 g, 15 mmol) was taken up in THF (75 ml). CH3MgBr (25 ml of a 3.0 M solution in Et2O) was added to the reaction mixture at 0° C. The solution was allowed to warm to 25° C. and was stirred at that temperature for 18 h. The solution was partitioned between 25 wt % aqueous solution of sodium citrate and E... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Hydrazine | C1CCOC1 | C1CC[NH]CC1.C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1 | null | CCOCC | 25 | 18 | C1CCOC1.[C-]#N>CCOCC>C1CCN(N2CCCCC2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a62cf4c9ffc84cf08a93f17d6e865c73 | CCOC(=O)C(N)=S.NNC=O>>CCOC(=O)C(=N)N(N)C=O | CCOC(=O)C(=S)N.C(=O)NN>>C(C)OC(C(=N)N(N)C=O)=O | S=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH2:7].[NH:8]([NH2:9])[CH:10]=[O:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[NH:7])[N:8]([NH2:9])[CH:10]=[O:11] | CCOC(=O)C(N)=S.NNC=O | CCOC(=O)C(=N)N(N)C=O | null | null | null | Protection | OtherReaction | c4b27c1213158e1bfc886814f12fcb53784c11c9ec9029618b3f1d81de62fc12 | 9617686fe76c15f2d8bd8bebff1aafad40c1d3c1e0f2a03f7c137b07e88e012d | null | S=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[N;D1;H2:7]-[NH;D2;+0:8]-[C:9]=[O;D1;H0:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[NH;D1;+0:2])-[N;H0;D3;+0:8](-[N;D1;H2:7])-[C:9]=[O;D1;H0:10] | 76.3 | [{"value": 76.0, "product": "C(C)OC(C(=N)N(N)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "C(C)OC(C(=N)N(N)C=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | A mixture of ethyl thioxamate (10.55 g, 79.2 mmol) and formylhydrazine (5.00 g, 83.2 mmol) was heated at 65° C. for 30 minutes and stirred in accordance with a method described in Collect. Czech Chem. Commun., 1984, 49, p 2492. After cooling, the precipitated crystal was collected by filteration and washed with ethanol... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ester.Thioamide | Acylhydrazine.Ester | null | null | null | Other | null | 65 | null | CCOC(=O)C(N)=S.NNC=O>>CCOC(=O)C(=N)N(N)C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b7b68e3c87e41339a24a58d40a683c6 | CCOC(=O)C(=N)N(N)C=O>>CCOC(=O)c1nc[nH]n1 | C(C)OC(C(=N)N(N)C=O)=O.COCCOCCOC>>C(C)OC(=O)C1=NNC=N1 | O=[CH:8][N:9]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[NH:7])[NH2:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][nH:9][n:10]1 | CCOC(=O)C(=N)N(N)C=O | CCOC(=O)c1nc[nH]n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 82cbfa315e066aa83edf1b332d93acee2b702a3b766354eed45936fa371ff6f0 | 8d9b5f7a99988769acbbac4ca3c0ce13a2919628fe63b34f32e3cf03e6a6610e | c1nc[nH]n1 | O=[CH;D2;+0:1]-[N;H0;D3;+0:2](-[NH2;D1;+0:3])-[C;H0;D3;+0:4](=[NH;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[nH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:5]:1 | 85 | [{"value": 85.0, "product": "C(C)OC(=O)C1=NNC=N1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of (N-Formylhydrazino)-imino acetic acid ethyl ester (9.62 g, 60.4 mmol) in diglyme (40 ml) was refluxed for 30 minutes. After cooling, the precipitated crystal was collected by filteration and washed with hexane to give 1H-1,2,4-triazol-3-carboxylic acid ethyl ester (7.28 g). Yield: 85%.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ester | Ester | null | c1nnc[nH]1 | c1nnc[nH]1 | HO- | null | null | null | CCOC(=O)C(=N)N(N)C=O>>CCOC(=O)c1nc[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7128cd1309b044118228bc991451e2cd | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1nc[nH]n1>>c1ccc(C(c2ccccc2)(c2ccccc2)n2cncn2)cc1 | O.N1N=CN=C1.[H-].[Na+].C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1N=CN=C1 | Cl[C:5]([c:4]1[cH:3][cH:2][cH:1][cH:24][cH:23]1)([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[nH:18]1[cH:19][n:20][cH:21][n:22]1>>[cH:1]1[cH:2][cH:3][c:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]2[cH:19][n:20][cH:21][n:22]2... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1nc[nH]n1 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cncn2)cc1 | null | null | CN(C)C=O.CCCCCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f37436bb10fcbe3c1fd9dd9deea86bed803d17db8f946b27cfa130fbd1907998 | 677f263b618a481bcdc02c85060e6c44b1f44f328207057cd4782b98754b7773 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cncn2)cc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#7;a:11]1:[c:12]:[nH;D2;+0:13]:[#7;a:14]:[c:15]:1>>[c:9]:[c:8](-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[n;H0;D3;+0:13]1:[#7;a:14]:[c:15]:[#7;a:11]:[c:12]:1):[c:10] | 47 | [{"value": 47.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1N=CN=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1N=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium hydride (60% dispersion in mineral oil, 13.8 g, 345 mmol) was washed with hexane and suspended in DMF (150 ml). At an ice bath temperature, 1,2,4-triazole (total; 20.7 g, 300 mmol) was added thereto in four divisions. After stirring for 30 minutes, to the mixture was added tritylchloride (total; 83.7 g, 300 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | c1nc[nH]n1 | c1nc[nH]n1 | c1ccccc1.c1ccccc1.c1ccccc1.c1nc[nH]n1 | HCl | CN(C)C=O.CCCCCC | null | 0.5 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1nc[nH]n1>CN(C)C=O.CCCCCC>c1ccc(C(c2ccccc2)(c2ccccc2)n2cncn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c10e714fc7e148e69733375bd5af3226 | CC(=O)c1ccc[nH]1.Fc1ccc(CBr)cc1>>CC(=O)c1cccn1Cc1ccc(F)cc1 | FC1=CC=C(CBr)C=C1.[H-].[Na+].C(C)(=O)C=1NC=CC1>>C(C)(=O)C=1N(C=CC1)CC1=CC=C(C=C1)F | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][nH:8]1.Br[CH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][n:8]1[CH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | CC(=O)c1ccc[nH]1.Fc1ccc(CBr)cc1 | CC(=O)c1cccn1Cc1ccc(F)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 161a14961e9f1b305dfb4891994ad58540b58501680f8eb4ba76ad15e1e7cb96 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2cccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 99.7 | [{"value": 99.7, "product": "C(C)(=O)C=1N(C=CC1)CC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of sodium hydride (60% in mineral oil, 1.32 g, 33 mmol) in DMF (30 ml) was added at an ice bath temperature a solution of 2-acetylpyrrole (3.27 g, 30 mmol) in DMF (5 ml). The mixture was stirred at room temperature for 15 minutes and cooled again. To the solution was added dropwise a solution of 4-fluor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1.c1ccccc1 | HBr | CN(C)C=O | null | 0.25 | CC(=O)c1ccc[nH]1.Fc1ccc(CBr)cc1>CN(C)C=O>CC(=O)c1cccn1Cc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-adb81272ca584cc785975b5ebb402ce7 | BrCc1ccccc1.O=Cc1ccc[nH]1>>O=Cc1cccn1Cc1ccccc1 | C(C1=CC=CC=C1)Br.[H-].[Na+].C(=O)C=1NC=CC1>>C(C1=CC=CC=C1)N1C(=CC=C1)C=O | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][nH:7]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][n:7]1[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | BrCc1ccccc1.O=Cc1ccc[nH]1 | O=Cc1cccn1Cc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 161a14961e9f1b305dfb4891994ad58540b58501680f8eb4ba76ad15e1e7cb96 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2cccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[O;D1;H0:5]=[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 97.2 | [{"value": 97.2, "product": "C(C1=CC=CC=C1)N1C(=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of sodium hydride (60% in mineral oil, 4.8 g, 120 mmol) in DMF (100 ml) was added dropwise at an ice bath temperature a solution of 2-formylpyrrole (9.5 g, 100 mmol) in DMF (10 ml). The mixture was stirred for 15 minutes at room temperature and cooled again. To the mixture was added dropwise a solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1.c1ccccc1 | HBr | CN(C)C=O | null | 0.25 | BrCc1ccccc1.O=Cc1ccc[nH]1>CN(C)C=O>O=Cc1cccn1Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69dcbe63ba36463aa189ba6520443fe6 | CCOP(=O)(CC(=O)OC)OCC.O=Cc1cccn1Cc1ccccc1>>COC(=O)C=Cc1cccn1Cc1ccccc1 | C(C1=CC=CC=C1)N1C(=CC=C1)C=O.[H-].[Na+].C(C)OP(OCC)(=O)CC(=O)OC>>C(C1=CC=CC=C1)N1C(=CC=C1)C=CC(=O)OC | CCOP(=O)(OCC)[CH2:5][C:3]([O:2][CH3:1])=[O:4].O=[CH:6][c:7]1[cH:8][cH:9][cH:10][n:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][n:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CCOP(=O)(CC(=O)OC)OCC.O=Cc1cccn1Cc1ccccc1 | COC(=O)C=Cc1cccn1Cc1ccccc1 | null | null | CN(C)C=O | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(Cn2cccc2)cc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].O=[CH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9](-[C:10]):[c:11]>>[C:10]-[#7;a:9](:[c:11]):[c:7](-[CH;D2;+0:6]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:8] | 65.1 | [{"value": 65.1, "product": "C(C1=CC=CC=C1)N1C(=CC=C1)C=CC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of sodium hydride (60% in mineral oil, 960 mg, 24 mmol) in DMF (20 ml) was added dropwise at an ice bath temperature a solution of diethyl(methoxycarbonylmethyl)phosphonate (5.04 g, 24 mmol) in DMF (1 ml). The mixture was stirred for 15 minutes at room temperature and cooled again. To the mixture was ad... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccc[nH]1.c1ccccc1 | HO- | CN(C)C=O | null | 0.25 | CCOP(=O)(CC(=O)OC)OCC.O=Cc1cccn1Cc1ccccc1>CN(C)C=O>COC(=O)C=Cc1cccn1Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f8ffdd4a3dcd491a8cc70900384a71ec | CCOP(=O)(CC(=O)OC)OCC.O=Cc1ccn(Cc2ccccc2)c1>>COC(=O)C=Cc1ccn(Cc2ccccc2)c1 | C(C1=CC=CC=C1)N1C=C(C=C1)C=O.[H-].[Na+].C(C)OP(OCC)(=O)CC(=O)OC>>C(C1=CC=CC=C1)N1C=C(C=C1)C=CC(=O)OC | CCOP(=O)(OCC)[CH2:5][C:3]([O:2][CH3:1])=[O:4].O=[CH:6][c:7]1[cH:8][cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | CCOP(=O)(CC(=O)OC)OCC.O=Cc1ccn(Cc2ccccc2)c1 | COC(=O)C=Cc1ccn(Cc2ccccc2)c1 | null | null | CN(C)C=O | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(Cn2cccc2)cc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].O=[CH;D2;+0:6]-[c:7]1:[c:8]:[#7;a:9](-[C:10]):[c:11]:[c:12]:1>>[C:10]-[#7;a:9]1:[c:8]:[c:7](-[CH;D2;+0:6]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:12]:[c:11]:1 | 83 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)N1C=C(C=C1)C=CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "C(C1=CC=CC=C1)N1C=C(C=C1)C=CC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of sodium hydride (60% in mineral oil, 311 mg, 7.8 mmol) in DMF (15 ml) was added dropwise at an ice bath temperature a solution of diethyl(methoxycarbonylmethyl)phosphonate (1.64 g, 7.8 mmol) in DMF (3 ml). The mixture was stirred for 30 minutes at room temperature and cooled again. To the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1cc[nH]c1.c1ccccc1 | HO- | CN(C)C=O | null | 0.5 | CCOP(=O)(CC(=O)OC)OCC.O=Cc1ccn(Cc2ccccc2)c1>CN(C)C=O>COC(=O)C=Cc1ccn(Cc2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a974fa5d025a477aaee1506f61791129 | O=S(=O)(Cl)c1ccccc1.c1cc[nH]c1>>O=S(=O)(c1ccccc1)n1cccc1 | C1(=CC=CC=C1)S(=O)(=O)Cl.[H-].[Na+].N1C=CC=C1>>C1(=CC=CC=C1)S(=O)(=O)N1C=CC=C1 | Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[nH:10]1[cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][cH:12][cH:13][cH:14]1 | O=S(=O)(Cl)c1ccccc1.c1cc[nH]c1 | O=S(=O)(c1ccccc1)n1cccc1 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | 386dff74aa0346e7145b20a4012c3b0d9b352dd97b63b297ab0f82a11c551988 | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=S(=O)(c1ccccc1)n1cccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[n;H0;D3;+0:11]1:[c:7]:[c:8]:[c:9]:[c:10]:1 | 736.9 | [{"value": 81.0, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 736.9, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of sodium hydride (60% in mineral oil, 2.4 g, 60 mmol) in DMF (100 ml) was added dropwise at an ice bath temperature a solution of pyrrole (3.35 g, 50 mmol) in DMF (5 ml). The mixture was stirred for 30 minutes at room temperature and cooled again. To the mixture was added dropwise a soluton of benzenes... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | HCl | CN(C)C=O | null | 0.5 | O=S(=O)(Cl)c1ccccc1.c1cc[nH]c1>CN(C)C=O>O=S(=O)(c1ccccc1)n1cccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fed017dcf7f8447fae2645dbb6325d21 | O=C(Cl)c1ccc(F)cc1.O=S(=O)(c1ccccc1)n1cccc1>>O=C(c1ccc(F)cc1)c1cccn1S(=O)(=O)c1ccccc1 | FC1=CC=C(C(=O)Cl)C=C1.B(F)(F)F.C1(=CC=CC=C1)S(=O)(=O)N1C=CC=C1>>C1(=CC=CC=C1)S(=O)(=O)N1C(=CC=C1)C(C1=CC=C(C=C1)F)=O | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1.[cH:10]1[cH:11][cH:12][cH:13][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23... | O=C(Cl)c1ccc(F)cc1.O=S(=O)(c1ccccc1)n1cccc1 | O=C(c1ccc(F)cc1)c1cccn1S(=O)(=O)c1ccccc1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | e822db33d5c478fdbb060e8fef14a2f90f9dbcacd07de404cce4bd16efdc1443 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1cccn1S(=O)(=O)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#16:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1>>[#16:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 33 | [{"value": 19.8, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C(=CC=C1)C(C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.0, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C(=CC=C1)C(C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 4-fluorobenzoylchloride (1.74 g, 11 mmol) in dichloromethane (2ml) was added dropwise a solution of boron trifluoride diethyletherate (3.4 ml, 27.6 mmol) in dichloromethane (20 ml). The mixture was stirred for 10 minutes at room temperature. Subsequently, to the mixture was added dropwise a solution of... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1cc[nH]c1 | c1ccc[nH]1 | c1ccccc1.c1ccc[nH]1.c1ccccc1 | HCl | ClCCl | null | 0.166667 | O=C(Cl)c1ccc(F)cc1.O=S(=O)(c1ccccc1)n1cccc1>ClCCl>O=C(c1ccc(F)cc1)c1cccn1S(=O)(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6991e5618fb54c83871f08fecd22030d | O=C(O)c1ccc(Cc2ccc(F)cc2)o1.O=S(Cl)Cl>>O=C(Cl)c1ccc(Cc2ccc(F)cc2)o1 | FC1=CC=C(CC2=CC=C(O2)C(=O)O)C=C1.S(=O)(Cl)Cl>>FC1=CC=C(CC2=CC=C(O2)C(=O)Cl)C=C1 | O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[o:16]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[o:16]1 | O=C(O)c1ccc(Cc2ccc(F)cc2)o1.O=S(Cl)Cl | O=C(Cl)c1ccc(Cc2ccc(F)cc2)o1 | null | null | CN(C)C=O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc(Cc2ccco2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[#8;a:6]:[c:7]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[#8;a:6]:[c:7] | 100.6 | [{"value": 100.6, "product": "FC1=CC=C(CC2=CC=C(O2)C(=O)Cl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To 5-(4-fluorobenzyl)-2-furan carboxylic acid (450 mg, 2 mmol) were added thionylchloride (1 ml, 13.7 mmol) and DMF (0.025 ml). The mixture was stirred for 30 minutes at room temperature. The excess amount of thionylchloride was evaporated. The precipitated residue was washed with n-hexane to give crude 5-(4-fluorobenz... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccoc1.c1ccccc1 | HCl | CN(C)C=O | null | 0.5 | O=C(O)c1ccc(Cc2ccc(F)cc2)o1.O=S(Cl)Cl>CN(C)C=O>O=C(Cl)c1ccc(Cc2ccc(F)cc2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-719ecd62b0b94a0fbbe448ddbdc6e91c | CC(=O)c1ccc(Cc2ccc(F)cc2)o1.CCOC(=O)C[Si](C)(C)C>>C=C(O[Si](C)(C)C)c1ccc(Cc2ccc(F)cc2)o1 | C(C)(=O)C=1OC(=CC1)CC1=CC=C(C=C1)F.C(C)OC(C[Si](C)(C)C)=O>>FC1=CC=C(CC2=CC=C(O2)C(=C)O[Si](C)(C)C)C=C1 | [CH3:1][C:2](=[O:3])[c:8]1[cH:9][cH:10][c:11]([CH2:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[o:20]1.CCOC(=O)C[Si:4]([CH3:5])([CH3:6])[CH3:7]>>[CH2:1]=[C:2]([O:3][Si:4]([CH3:5])([CH3:6])[CH3:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[o:20]1 | CC(=O)c1ccc(Cc2ccc(F)cc2)o1.CCOC(=O)C[Si](C)(C)C | C=C(O[Si](C)(C)C)c1ccc(Cc2ccc(F)cc2)o1 | null | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1CCOC1 | Acylation | OtherReaction | 0f0b9904a4358b3ba8199f6928b04f50037e5c72b9920af3fbcdecbd5601cf76 | 40cb05552a16441c3106c7e1251cdef68c53a280e5dade33ab37da6a8cbcb1d2 | c1ccc(Cc2ccco2)cc1 | C-C-O-C(=O)-C-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[#8;a:10]:[c:11]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:7]-[C;H0;D3;+0:6](=[CH2;D1;+0:5])-[c:8](:[c:9]):[#8;a:10]:[c:11] | 88 | [{"value": 88.0, "product": "FC1=CC=C(CC2=CC=C(O2)C(=C)O[Si](C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "FC1=CC=C(CC2=CC=C(O2)C(=C)O[Si](C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 2-acetyl-5-(4-fluorobenzyl)furan (10 g, 46 mmol) and trimethylsilylacetic acid ethyl ester (10.9 g, 68 mmol) in anhydrous THF (30 ml) was cooled at −20° C. To a solution was added anhydrous tetrabutylammoniumfluoride (0.2 g). The reaction mixture was gradually warmed up to room temperature and stirred for... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Silyl protective group | Vinyl.Silyl protective group | null | null | c1ccoc1.c1ccccc1 | HO- | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1CCOC1 | null | 0.25 | CC(=O)c1ccc(Cc2ccc(F)cc2)o1.CCOC(=O)C[Si](C)(C)C>[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1CCOC1>C=C(O[Si](C)(C)C)c1ccc(Cc2ccc(F)cc2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8400f85c019d454b882269b9507c637d | N[C@H](CO)Cc1ccccc1.O=Cc1ccccc1>>OC[C@H](Cc1ccccc1)NCc1ccccc1 | N[C@@H](CC1=CC=CC=C1)CO.C(C)(=O)O.C(#N)[BH3-].[Na+].C(C1=CC=CC=C1)=O>>C(C1=CC=CC=C1)N[C@@H](CC1=CC=CC=C1)CO | [OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH2:11].O=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | N[C@H](CO)Cc1ccccc1.O=Cc1ccccc1 | OC[C@H](Cc1ccccc1)NCc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CCNCc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[C:7])-[NH2;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 81 | [{"value": 81.0, "product": "C(C1=CC=CC=C1)N[C@@H](CC1=CC=CC=C1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "C(C1=CC=CC=C1)N[C@@H](CC1=CC=CC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 18 | HOUR | L-Phenylalaninol (89.51 g, 0.592 moles) was dissolved in 375 mL of methanol under inert atmosphere, 35.52 g (0.592 moles) of glacial acetic acid and 50 mL of methanol was added followed by a solution of 62.83 g (0.592 moles) of benzaldehyde in 100 mL of methanol. The mixture was cooled to approximately 15° C. and a sol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | CO | 15 | 18 | N[C@H](CO)Cc1ccccc1.O=Cc1ccccc1>CO>OC[C@H](Cc1ccccc1)NCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44a383223fe44b849e78edd1e0e8a2be | N[C@H](CO)Cc1ccccc1.O=Cc1ccccc1>>OC[C@H](Cc1ccccc1)NCc1ccccc1 | N[C@@H](CC1=CC=CC=C1)CO.C(C1=CC=CC=C1)=O.[H][H]>>C(C1=CC=CC=C1)N[C@@H](CC1=CC=CC=C1)CO | [OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH2:11].O=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[OH:1][CH2:2][C@H:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | N[C@H](CO)Cc1ccccc1.O=Cc1ccccc1 | OC[C@H](Cc1ccccc1)NCc1ccccc1 | null | [Pt] | C(C)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CCNCc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[C:7])-[NH2;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 48.1 | [{"value": 48.0, "product": "C(C1=CC=CC=C1)N[C@@H](CC1=CC=CC=C1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.1, "product": "C(C1=CC=CC=C1)N[C@@H](CC1=CC=CC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | L-Phenylalaninol (5 g, 33 mmoles) and 3.59 g (33.83 mmoles) of benzaldehyde were dissolved in 55 mL of 3A ethanol under inert atmosphere in a Parr shaker and the mixture was warmed to 60° C. for 2.7 hours. The mixture was cooled to approximately 25° C. and 0.99 g of 5% platinum on carbon was added and the mixture was h... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pt].C(C)O | 60 | null | N[C@H](CO)Cc1ccccc1.O=Cc1ccccc1>[Pt].C(C)O>OC[C@H](Cc1ccccc1)NCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c94109cc2e8b43969e418606a386899d | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](CO)Cc1ccccc1>>CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1 | C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)CO)CC1=CC=CC=C1.CC1(CCCC(N1[O])(C)C)C.[Br-].[Na+].C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)C=O)CC1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C@H:16]([CH2:17][OH:18])[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C@H:16]([CH:17]=[O:18])[CH2:19]... | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](CO)Cc1ccccc1 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1 | null | null | O.C(C)(=O)OCC.C1(=CC=CC=C1)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(CCNCc2ccccc2)cc1 | [C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH2;D2;+0:11]-[OH;D1;+0:12]>>[C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12] | 100.3 | [{"value": 100.0, "product": "C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)C=O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.3, "product": "C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)C=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | To a solution of 0.32 g (0.94 mmoles) of N-(t-butoxycarbonyl)-N-benzyl-L-phenylalaninol in 2.8 mL of toluene was added 2.4 mg (0.015 mmoles) of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (TEMPO), 0.1 g (0.97 mmoles) of sodium bromide, 2.8 mL of ethyl acetate and 0.34 mL of water. The mixture was cooled to 0° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccccc1 | null | O.C(C)(=O)OCC.C1(=CC=CC=C1)C | 0 | 0.166667 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](CO)Cc1ccccc1>O.C(C)(=O)OCC.C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b344c2b7bf4c4f08a7044e05b3ab4726 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](CO)Cc1ccccc1>>CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1 | C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)CO)CC1=CC=CC=C1.C(C)N(CC)CC.O>>C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)C=O)CC1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C@H:16]([CH2:17][OH:18])[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C@H:16]([CH:17]=[O:18])[CH2:19]... | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](CO)Cc1ccccc1 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1 | null | null | CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(CCNCc2ccccc2)cc1 | [C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH2;D2;+0:11]-[OH;D1;+0:12]>>[C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12] | 100 | [{"value": 100.0, "product": "C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)C=O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)C=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2.38 g (6.98 mmoles) of N-(t-butoxycarbonyl)-N-benzyl-L-phenylalaninol in 3.8 mL (27.2 mmoles) of triethylamine at 10° C. was added a solution of 4.33 g (27.2 mmoles) of sulfur trioxide pyridine complex in 17 mL of dimethyl sulfoxide. The mixture was warmed to room temperature and stirred for one hour.... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccccc1 | null | CS(=O)C | null | 1 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](CO)Cc1ccccc1>CS(=O)C>CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbab15fbd2be46918a88f7a0972b05d8 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1>>CC(C)(C)OC(=O)N(Cc1ccccc1)[C@@H](Cc1ccccc1)[C@H]1CO1 | C(C)(C)(C)OC(=O)N([C@@H](CC1=CC=CC=C1)C=O)CC1=CC=CC=C1.[I-].C[S+](C)C.CC(C)([O-])C.[K+]>>C(C)(C)(C)OC(=O)N(CC1=CC=CC=C1)[C@H]([C@H]1CO1)CC1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C@@H:16]([CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH:24]=[O:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C@@H:16]([CH2:17][c:18]1[cH:19]... | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@@H](Cc1ccccc1)[C@H]1CO1 | null | null | O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2d8c350316fb727aeda6536184083b71a9b20f0ee07455d6d3abcb377b9f555a | e21ccb4bcf9a71eccf327a93a1fa5572944710ed52ebac44dc7df03f0c63c123 | c1ccc(CN[C@@H](Cc2ccccc2)[C@H]2CO2)cc1 | [C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12]>>[C:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C@H;D3;+0:11]1-[C:13]-[O;H0;D2;+0:12]-1 | 99.7 | [{"value": 99.7, "product": "C(C)(C)(C)OC(=O)N(CC1=CC=CC=C1)[C@H]([C@H]1CO1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 0.90 g (4.42 mmoles) of trimethylsulfonium iodide in 18 mL of acetonitrile was added 0.495 g (4.42 mmoles) of potassium t-butoxide. A solution of 1.0 g (2.95 mmoles) of N-(t-butoxycarbonyl)-N-benzyl-L-phenylalaninal in 7 mL of acetonitrile was added and the mixture was stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Ether | null | C1CO1 | c1ccccc1.c1ccccc1.C1CO1 | Other | O.C(C)#N | null | 1 | CC(C)(C)OC(=O)N(Cc1ccccc1)[C@H](C=O)Cc1ccccc1>O.C(C)#N>CC(C)(C)OC(=O)N(Cc1ccccc1)[C@@H](Cc1ccccc1)[C@H]1CO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de7cfce9039d48c5931678ece174a054 | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | ClCC(=O)CCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1 | O=C(CCl)[CH2:14][Cl:15].O=[C:12]([C@@H:4]([NH:3][C:2](=[O:1])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[OH:13]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@H:12]([OH:13])[CH2:14][Cl:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH... | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1 | O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 | null | null | CO.O1CCCC1 | C-C Coupling | OtherReaction | be975736ea4dc284d6befa072d9777b891132a86c932e209ec3849b788893253 | 1c7c048f8a75ee2977c3642525e5bc0c5f72d9781847729e637668c64f734260 | O=C(NCCc1ccccc1)OCc1ccccc1 | Cl-C-C(=O)-[CH2;D2;+0:1]-[Cl;D1;H0:2].O=[C;H0;D3;+0:3](-[O;D1;H1:4])-[C:5](-[C:6])-[#7:7]-[C:8]=[O;D1;H0:9]>>[C:6]-[C:5](-[#7:7]-[C:8]=[O;D1;H0:9])-[C@H;D3;+0:3](-[O;D1;H1:4])-[CH2;D2;+0:1]-[Cl;D1;H0:2] | 43 | [{"value": 43.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.8, "product": "C(C1=CC=CC=C1)OC(=O)N[C@H]([C@@H](CCl)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 75.0 g (0.226 mol) of N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone in a mixture of 807 mL of methanol and 807 mL of tetrahydrofuran at −2° C., was added 13.17 g (0.348 mol, 1.54 equiv.) of solid sodium borohydride over one hundred minutes. The solvents were removed under reduced pressure at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid.Ketone | Primary halide.Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | HCl | CO.O1CCCC1 | 60 | null | O=C(CCl)CCl.O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1>CO.O1CCCC1>O=C(N[C@@H](Cc1ccccc1)[C@H](O)CCl)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ae0c5722f76466c92866d5ed37fa793 | C1CCNC1.CC(C)(C)OC(=O)CBr>>O=C(O)CN1CCCC1 | BrCC(=O)OC(C)(C)C.Cl.N1CCCC1>>Cl.N1(CCCC1)CC(=O)O | [NH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1.CC(C)(C)[O:4][C:3](=[O:2])[CH2:5]Br>>[O:2]=[C:3]([OH:4])[CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1 | C1CCNC1.CC(C)(C)OC(=O)CBr | O=C(O)CN1CCCC1 | null | null | C1CCOC1.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 43a84de835faf6f51ae14eb3c7f5f4c7470809d55775224233b013941814d67c | 6b6be5f7180fc31350aca7745a263bf1841954130aec6ae006fa2b524bf8eee0 | C1CCNC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C(-C)(-C)-C.[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 97.4 | [{"value": 97.4, "product": "Cl.N1(CCCC1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 19.6 grams (101 mmol) of t-butyl bromoacetate in 150 mL of THF was cooled in an ice bath and treated dropwise over about 0.5 hour with a solution of 14.4 grams (202 mmol) of pyrrolidine in 75 mL of THF, to produce a white precipitate. The bath was removed and the reaction slurry stirred for two hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine.Boc | Carboxylic acid.Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HBr | C1CCOC1.O1CCOCC1 | null | 2 | C1CCNC1.CC(C)(C)OC(=O)CBr>C1CCOC1.O1CCOCC1>O=C(O)CN1CCCC1 |
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