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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-29c8827cd31c428e880bc3405a0f7ad5 | CC(=O)OCCC1C=CC=CC1(C)C.[Cl-]>>CC(=O)OCCC1C=CC(C(=O)CCCCl)=CC1(C)C | C(C)(=O)OCCC1C(C=CC=C1)(C)C.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)(=O)OCCC1C(C=C(C=C1)C(CCCCl)=O)(C)C | [CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH:7]1[CH:8]=[CH:11][CH:10]=[CH:17][C:18]1([CH3:9])[CH3:13].[Cl-:16]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH:7]1[CH:8]=[CH:9][C:10]([C:11](=[O:12])[CH2:13][CH2:14][CH2:15][Cl:16])=[CH:17][C:18]1([CH3:19])[CH3:20] | CC(=O)OCCC1C=CC=CC1(C)C.[Cl-] | CC(=O)OCCC1C=CC(C(=O)CCCCl)=CC1(C)C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 5ef5cb71810a57035c6dedc7f99e0099f05c9d4f665b03f4f662851409342c28 | 1610e973d7338028dc2e0b177fb2ac8357f539786af7f37ca444fafdb64bb9fb | C1=CCCC=C1 | [C:1]-[C:2]1-[CH;D2;+0:3]=[CH;D2;+0:4]-[CH;D2;+0:5]=[C:6]-[C;H0;D4;+0:7]-1(-[CH3;D1;+0:8])-[CH3;D1;+0:9].[Cl-;H0;D0:10]>>[C:1]-[C:2]1-[CH;D2;+0:3]=[CH;D2;+0:9]-[C;H0;D3;+0:5](-[C;H0;D3;+0:4](=[O;D1;H0:11])-[CH2;D2;+0:8]-[C:12]-[C:13]-[Cl;H0;D1;+0:10])=[C:6]-[C;H0;D4;+0:7]-1(-[C;D1;H3:14])-[C;D1;H3:15] | null | [] | 0 | CELSIUS | 2 | HOUR | Charge a flask with aluminum chloride (223 g, 1.68 mol) and methylene chloride (200 mL). Place under a nitrogen atmosphere, cool to 0°-5° C. and add, by dropwise addition, ω-chlorobutyryl chloride (188.6 g, 1.34 mol). After acid chloride addition is complete, add, by dropwise addition, 2,2-dimethylphenethyl acetate (12... | 10.6084/m9.figshare.5104873.v1 | null | Conjugated diene | Primary halide.Ketone | C1=CCCC=C1 | C1=CCCC=C1 | C1=CCCC=C1 | null | C(Cl)Cl | 0 | 2 | CC(=O)OCCC1C=CC=CC1(C)C.[Cl-]>C(Cl)Cl>CC(=O)OCCC1C=CC(C(=O)CCCCl)=CC1(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5dd5b0600d7347a69a18856ca56c7906 | CC(=O)OCCC1C=CC(C(=O)CCCCl)=CC1(C)C.OC(c1ccccc1)(c1ccccc1)C1CCNCC1>>CC(=O)OCCC1C=CC(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)=CC1(C)C | C(C)(=O)OCCC1C(C=C(C=C1)C(CCCCl)=O)(C)C.C1(=CC=CC=C1)C(O)(C1CCNCC1)C1=CC=CC=C1.C(O)([O-])=O.[K+].[I-].[K+]>>C(C)(=O)OCCC1C(C=C(C=C1)C(CCCN1CCC(CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)O)=O)(C)C | Cl[CH2:15][CH2:14][CH2:13][C:11]([C:10]1=[CH:36][C:37]([CH3:38])([CH3:39])[CH:7]([CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3])[CH:8]=[CH:9]1)=[O:12].[NH:16]1[CH2:17][CH2:18][CH:19]([C:20]([OH:21])([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[CH2:34][CH2:35]1>>[CH3:1][C:2](=[O:3])[... | CC(=O)OCCC1C=CC(C(=O)CCCCl)=CC1(C)C.OC(c1ccccc1)(c1ccccc1)C1CCNCC1 | CC(=O)OCCC1C=CC(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)=CC1(C)C | null | null | O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC(C(c2ccccc2)c2ccccc2)CC1)C1=CCCC=C1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5])-[C:9]-[C:10] | null | [] | null | null | null | null | Mix 4-(4-chloro-1-oxobutyl)-2,2-dimethylphenethyl acetate (99.5 g, 0.335 mol), α,α-diphenyl-4-piperidinemethanol (101.8 g, 0.335 mol), potassium hydrogen carbonate (83.8 g, 0.838 mol), potassium iodide (1.00 g, 0.006 mol), toluene (600 mL) and water (220 mL). Stir at reflux for 72 hours, add toluene (200 mL) and deioni... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1=CCCC=C1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | O.C1(=CC=CC=C1)C | null | null | CC(=O)OCCC1C=CC(C(=O)CCCCl)=CC1(C)C.OC(c1ccccc1)(c1ccccc1)C1CCNCC1>O.C1(=CC=CC=C1)C>CC(=O)OCCC1C=CC(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)=CC1(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4b6a70144d674624b9c58662f50c1c4a | CC(=O)OCCC1C=CC(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)=CC1(C)C>>CC1(C)C=C(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)C=CC1CCO | C(C)(=O)OCCC1C(C=C(C=C1)C(CCCN1CCC(CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)O)=O)(C)C.[OH-].[Na+]>>OC(C1CCN(CC1)CCCC(=O)C1=CC(C(CCO)C=C1)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 | CC(=O)[O:36][CH2:35][CH2:34][CH:33]1[C:2]([CH3:1])([CH3:3])[CH:4]=[C:5]([C:6](=[O:7])[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:15]([OH:16])([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[CH2:29][CH2:30]2)[CH:31]=[CH:32]1>>[CH3:1][C:2]1([CH3:3])[CH:4]=[C:5]([C:6](=... | CC(=O)OCCC1C=CC(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)=CC1(C)C | CC1(C)C=C(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)C=CC1CCO | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(CCCN1CCC(C(c2ccccc2)c2ccccc2)CC1)C1=CCCC=C1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | 68 | CELSIUS | null | null | Dissolve 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl acetate (69.0 g, 0.131 mol) in methanol (2.5 L) and add 10% aqueous sodium hydroxide (769 mL, 1.92 mol). Stir at reflux for 1.5 hours, cool to 68° C. and evaporate the solvent in vacuo to a residue (700 mL). Add chloroform (1 L) a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1=CCCC=C1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | CO | 68 | null | CC(=O)OCCC1C=CC(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)=CC1(C)C>CO>CC1(C)C=C(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)C=CC1CCO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-29726a5e871f429b913072c32bc61abe | CC1(C)C=C(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)C=CC1CCO>>CC(C)(C=O)c1ccc(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 | OOS(=O)[O-].[K+].OC(C1CCN(CC1)CCCC(=O)C1=CC(C(CCO)C=C1)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)C.C(C(=O)Cl)(=O)Cl>>OC(C1CCN(CC1)CCCC(=O)C1=CC=C(C=C1)C(C=O)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][C:2]1([CH3:3])[CH:6]([CH2:36][CH2:4][OH:5])[CH:7]=[CH:8][C:9]([C:10](=[O:11])[CH2:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:19]([OH:20])([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[CH2:33][CH2:34]2)=[CH:35]1>>[CH3:1][C:2]([CH3:3])([CH:4]=[O:5])[c:6]1[cH:7]... | CC1(C)C=C(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)C=CC1CCO | CC(C)(C=O)c1ccc(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 | null | null | O.C(C)N(CC)CC.C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 0b92622e17cbcd5037c213ae72b0962476efef86e5859a8abce2e0a32dc664eb | f3548b67daf322ebbb684ef4651a567bc61dc1096a4d22fc7de614d6c8911d3e | O=C(CCCN1CCC(C(c2ccccc2)c2ccccc2)CC1)c1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[CH;D3;+0:9](-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[OH;D1;+0:12])-[CH;D2;+0:13]=[CH;D2;+0:14]-1>>[C:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:10]:[c;H0;D3;+0:9](-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[CH;... | null | [] | -55 | CELSIUS | 15 | MINUTE | Dissolve oxalyl chloride (1.57 g, 12.4 mmol) in methylene chloride (17 mL), cool to -55° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution of dimethylsulfoxide (1.77 g, 1.61 mL) in methylene chloride (4.5 mL). Stir for 15 minutes and add, by dropwise addition, a solution of 4-[4-[4-(hydrox... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol | Aldehyde.Ketone | C1=CCCC=C1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | null | O.C(C)N(CC)CC.C(Cl)Cl | -55 | 0.25 | CC1(C)C=C(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)C=CC1CCO>O.C(C)N(CC)CC.C(Cl)Cl>CC(C)(C=O)c1ccc(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f974a4c16b9e4bb6abc70ae4b17f78a7 | CCOC(=O)C(C)(C)c1ccc(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1>>CCOC(=O)C(C)(C)c1ccc([C@@H](O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 | B([C@@H]1C[C@@H]2C[C@H]([C@H]1C)C2(C)C)([C@@H]3C[C@@H]4C[C@@H]([C@H]3C)C4(C)C)Cl.OC(C1CCN(CC1)CCCC(=O)C1=CC=C(C=C1)C(C(=O)OCC)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1.O.OO>>OC(C1CCN(CC1)CCC[C@H](O)C1=CC=C(C=C1)C(C(=O)OCC)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][CH:21]([C:22]([OH:23])([c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)[CH2:36][CH2:37]2)[cH:38][cH:39]1>>[CH3:1][CH2:2][O:3][C:4](=[O:... | CCOC(=O)C(C)(C)c1ccc(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 | CCOC(=O)C(C)(C)c1ccc([C@@H](O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(CCCCN2CCC(C(c3ccccc3)c3ccccc3)CC2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 3 | DAY | Dissolve (-)-B-chlorodiisopinocamphenylborane (2.5 g, 7.8 mmol) in anhydrous tetrahydrofuran (5 mL). Add a solution of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid, ethyl ester (2 g, 3.54 mmol) in anhydrous tetrahydrofuran (5 mL). Stir at room temperature for 3 days and cool... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | null | O1CCCC1 | null | 72 | CCOC(=O)C(C)(C)c1ccc(C(=O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1>O1CCCC1>CCOC(=O)C(C)(C)c1ccc([C@@H](O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-39cd18b1fe7e4c7ebb46840142616584 | CCCCCCCCCCC=CC1CC(=O)OC1=O.NCC(O)CO>>CCCCCCCCCCC=CC(O)C(O)C=N.O=C(O)CCC(=O)O | NCC(CO)O.C(=CCCCCCCCCCC)C1C(=O)OC(C1)=O>>C(CCC(=O)O)(=O)O.C(=CCCCCCCCCCC)C(C(C=N)O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH:22]1[C:20](=[O:19])[O:26][C:24](=[O:25])[CH2:23]1.[CH2:13]([OH:14])[CH:15]([OH:16])[CH2:17][NH2:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][CH:13]([OH:14])[CH:15]([OH:16])[CH:17]=[NH... | CCCCCCCCCCC=CC1CC(=O)OC1=O.NCC(O)CO | CCCCCCCCCCC=CC(O)C(O)C=N.O=C(O)CCC(=O)O | null | C[O-].[Na+] | null | Acylation | OtherReaction | 866cb6fbda0ea9751d0ba3f97ddb34fb1646f6085e65347e43178c34a0e896ad | 64d8d2098a6368c38c70da8cd200033d1f0cfb65017bf3991df4107bcebc8f1f | null | [C:1]-[C:2]=[CH;D2;+0:3]-[CH;D3;+0:4]1-[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[C;H0;D3;+0:9]-1=[O;D1;H0:10].[NH2;D1;+0:11]-[CH2;D2;+0:12]-[C:13](-[O;D1;H1:14])-[CH2;D2;+0:15]-[O;D1;H1:16]>>[C:1]-[C:2]=[CH;D2;+0:3]-[CH;D3;+0:15](-[O;D1;H1:16])-[C:13](-[O;D1;H1:14])-[CH;D2;+0:12]=[NH;D1;+0:11].[O;D1;H0:10]=[C;H0;D3;+0:... | 172.6 | [{"value": 94.9, "product": "C(CCC(=O)O)(=O)O.C(=CCCCCCCCCCC)C(C(C=N)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 172.6, "product": "C(CCC(=O)O)(=O)O.C(=CCCCCCCCCCC)C(C(C=N)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | null | null | A 100 ml four necked round bottom flask equipped with a mechanical stirrer, thermometer, nitrogen inlet and short path distillation head was charged with 3-amino-1,2-propandiol (8.0 g, 8.78×10-2 mole), dodecenyl succinic anhydride (23.4 g, 8.78×10-2 mole) and sodium methoxide (0.05 g, 9.26×10-4 mole). The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol.Primary amine | Carboxylic acid.Carboxylic acid.Unsubstituted imine.Secondary alcohol | C1CCOC1 | null | null | Other | C[O-].[Na+] | 135 | null | CCCCCCCCCCC=CC1CC(=O)OC1=O.NCC(O)CO>C[O-].[Na+]>CCCCCCCCCCC=CC(O)C(O)C=N.O=C(O)CCC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-57751326651f4ba2b298994bf5add7b7 | CC(C)N(C(=O)CCl)c1ccc(F)cc1>>CC(C)N(C(=O)CO)c1ccc(F)cc1 | ClCC(=O)N(C1=CC=C(C=C1)F)C(C)C.C([O-])([O-])=O.[Na+].[Na+]>>OCC(=O)N(C1=CC=C(C=C1)F)C(C)C | Cl[CH2:7][C:5]([N:4]([CH:2]([CH3:1])[CH3:3])[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)=[O:6]>>[CH3:1][CH:2]([CH3:3])[N:4]([C:5](=[O:6])[CH2:7][OH:8])[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1 | CC(C)N(C(=O)CCl)c1ccc(F)cc1 | CC(C)N(C(=O)CO)c1ccc(F)cc1 | null | null | null | Functional Group Interconversion | Primary alkyl halide to alcohol | 4c480ae19804ad5cf02c2cb44a1909d952eb2f0debe381a021a63e61ede789dc | 05def2467bf3ab45f9f8ab94784b02043dfccd675fa03a71edc68bf348b4f536 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6]>>[C:5]-[#7:4](-[c:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;D1;H1:7] | null | [] | 100 | CELSIUS | null | null | In a 500 ml flask, 23.0 g (0.1 mol) of N-chloroacetyl-N-isopropyl-4-fluoroaniline and 11.7 g (0.11 mol) of sodium carbonate in 340 ml of solvent or solvent mixture are heated with stirring to reflux temperature (100° C.). The reaction is monitored by gas chromatography (sampling after in each case 1 hour). The results ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary alcohol | null | null | c1ccccc1 | null | null | 100 | null | CC(C)N(C(=O)CCl)c1ccc(F)cc1>>CC(C)N(C(=O)CO)c1ccc(F)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ce568f1ccd5b44b58402f591866b07a9 | CC(C)N(C(=O)CCl)c1ccc(F)cc1.O>>CC(C)N(C(=O)CO)c1ccc(F)cc1 | ClCC(=O)N(C1=CC=C(C=C1)F)C(C)C.C([O-])([O-])=O.[Na+].[Na+].O>>OCC(=O)N(C1=CC=C(C=C1)F)C(C)C | Cl[CH2:7][C:5]([N:4]([CH:2]([CH3:1])[CH3:3])[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)=[O:6].[OH2:8]>>[CH3:1][CH:2]([CH3:3])[N:4]([C:5](=[O:6])[CH2:7][OH:8])[c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1 | CC(C)N(C(=O)CCl)c1ccc(F)cc1.O | CC(C)N(C(=O)CO)c1ccc(F)cc1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 231253c55c0f42174a17340b823c6702155eb165c3d2f7b555bb09f54b91b1a3 | e7141d94960d4874394ef66bcefdd72176a955fa44e71bb38bf7656b1bd4e11a | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6].[OH2;D0;+0:7]>>[C:5]-[#7:4](-[c:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[OH;D1;+0:7] | null | [] | null | null | 2.5 | HOUR | In a suitable apparatus (500 ml flask), 23.0 g (0.1 mol) of N-chloroacetyl-N-isopropyl-4-fluoroaniline and 11.7 g (0.11 mol) of sodium carbonate are refluxed (100° C.) in a solution of 140 ml of water and 200 ml of N-methylpyrrolidone. After 2.5 hours, the solvent mixture is stripped off in vacuo and the residue distil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary alcohol | null | null | c1ccccc1 | HCl | CN1C(CCC1)=O | null | 2.5 | CC(C)N(C(=O)CCl)c1ccc(F)cc1.O>CN1C(CCC1)=O>CC(C)N(C(=O)CO)c1ccc(F)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2920997f3a2d4e0aba7221e2957419ed | COC(Cl)C(=O)Nc1ccccc1>>COC(O)C(=O)Nc1ccccc1 | COC(C(=O)NC1=CC=CC=C1)Cl.C([O-])([O-])=O.[Na+].[Na+].CN1C(CCC1)=O>>COC(C(=O)NC1=CC=CC=C1)O | Cl[CH:3]([O:2][CH3:1])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][CH:3]([OH:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | COC(Cl)C(=O)Nc1ccccc1 | COC(O)C(=O)Nc1ccccc1 | null | null | O | Functional Group Interconversion | Secondary alkyl halide to alcohol | 89b376ffbf98d68c037321a30c742697262e8db91a374c4fc674cc25a2b2bec2 | bf43f45c65ec95e8e76680d730ef70bf9925388db70f78a9bf8ea68162bde734 | c1ccccc1 | Cl-[CH;D3;+0:1](-[#8:2]-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]>>[C;D1;H3:3]-[#8:2]-[CH;D3;+0:1](-[O;D1;H1:8])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7] | 70 | [{"value": 70.0, "product": "COC(C(=O)NC1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 250 ml flask, 10 g (0.05 mol) of 2-methoxy-chloroacetanilide (prepared from chloroacetyl chloride and 2-methoxyaniline) and 6 g (0.55 mol) of sodium carbonate are heated at 100° C. in a solvent mixture of 100 ml of N-methylpyrrolidone and 70 ml of water. A GC check after a reaction time of 6 hours reveals a yield ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Ether.Secondary alcohol | null | null | c1ccccc1 | null | O | null | null | COC(Cl)C(=O)Nc1ccccc1>O>COC(O)C(=O)Nc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6f6d381a5fb84cd8a0fb16856abfd593 | O=C(n1ccnc1)n1ccnc1>>O=C(n1ccnc1)n1ccnc1 | C(=O)(N1C=NC=C1)N1C=NC=C1.C(=O)(OC(C)(C)C)N[C@@H](CC1=CC=CC=C1)C(=O)O>>C(=O)(OC(C)(C)C)N[C@@H](CC1=CC=CC=C1)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1 | [O:20]=[C:21]([n:22]1[cH:23][cH:24][n:25][cH:26]1)[n:27]1[cH:28][cH:29][n:30][cH:31]1>>[O:20]=[C:21]([n:22]1[cH:23][cH:24][n:25][cH:26]1)[n:27]1[cH:28][cH:29][n:30][cH:31]1 | O=C(n1ccnc1)n1ccnc1 | O=C(n1ccnc1)n1ccnc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(n1ccnc1)n1ccnc1 | null | null | [] | null | null | null | null | In an argon atmosphere and under anhydrous conditions, 2.42 moles (391.8 g) of 1,1'-carbonyldiimidazole (CDI) and 3 liters of dry THF were mixed in a reactor. 1.89 moles (502.3 g) of Boc-phenylalanine was then added in five portions to the reactor to form a carbonyldiimidazole Boc-phenylalanine solution. Vigorous gas e... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1c[nH]cn1.c1c[nH]cn1 | null | C1CCOC1 | null | null | O=C(n1ccnc1)n1ccnc1>C1CCOC1>O=C(n1ccnc1)n1ccnc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1806ca5a65b346d78786c713a3316193 | CC(=O)N(c1ccc(C)cc1)c1c(C)cc(-c2cc(C)c(N(c3ccc(C)cc3)c3ccc(C)cc3)c(C)c2)cc1C.Ic1ccc2ccc3cccc4ccc1c2c34>>Cc1ccc(N(c2ccc(C)cc2)c2c(C)cc(-c3cc(C)c(N(c4ccc(C)cc4)c4ccc5ccc6cccc7ccc4c5c67)c(C)c3)cc2C)cc1 | CC1=CC=C(C=C1)N(C1=C(C=C(C=C1C)C1=CC(=C(N(C(C)=O)C2=CC=C(C=C2)C)C(=C1)C)C)C)C1=CC=C(C=C1)C.IC1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34>>CC1=CC=C(C=C1)N(C1=C(C=C(C=C1C)C1=CC(=C(N(C2=CC=C3C=CC4=CC=CC5=CC=C2C3=C45)C4=CC=C(C=C4)C)C(=C1)C)C)C)C1=CC=C(C=C1)C | CC(=O)[N:24]([c:23]1[c:15]([CH3:16])[cH:17][c:18](-[c:19]2[cH:20][c:21]([CH3:22])[c:14]([N:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:55][cH:54]3)[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]3)[c:48]([CH3:49])[cH:50]2)[cH:51][c:52]1[CH3:53])[c:25]1[cH:26][cH:27][c:28]([CH3:29])[cH:30][cH:31]1.I[c:32]1[cH:33][cH:34][c:35... | CC(=O)N(c1ccc(C)cc1)c1c(C)cc(-c2cc(C)c(N(c3ccc(C)cc3)c3ccc(C)cc3)c(C)c2)cc1C.Ic1ccc2ccc3cccc4ccc1c2c34 | Cc1ccc(N(c2ccc(C)cc2)c2c(C)cc(-c3cc(C)c(N(c4ccc(C)cc4)c4ccc5ccc6cccc7ccc4c5c67)c(C)c3)cc2C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b19edf8ea6dccfc143ce0d73cc76d9935d1e32ea082d490767b915ee9f282649 | da441520990db3b7dfc8421b343d1a69dceb643d35ca5c86f0c23a5d017d38e3 | c1ccc(N(c2ccccc2)c2ccc(-c3ccc(N(c4ccccc4)c4ccc5ccc6cccc7ccc4c5c67)cc3)cc2)cc1 | C-C(=O)-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:5]1:[c;H0;D3;+0:6](-[C;D1;H3:7]):[c:8]:[c:9](-[c:10]2:[c:11]:[c;H0;D3;+0:12](-[C;D1;H3:13]):[c;H0;D3;+0:14](-[#7:15](-[c:16])-[c:17]):[c;H0;D3;+0:18](-[C;D1;H3:19]):[c:20]:2):[c:21]:[c;H0;D3;+0:22]:1-[C;D1;H3:23].I-[c;H0;D3;+0:24](:[c:25]:[c:26]):[c:27](:[c:28]):... | null | [] | null | null | null | null | The thus obtained N,N,N'-tris(4-methylphenyl)-N'-acetyl-3,3',5,5'-tetramethylbenzidine was hydrolyzed, and the hydrolyzed product and 1-iodo-pyrene were subjected to the same Ullmann reaction as in Preparation Example 1-6, whereby N,N,N'-tris(4-methylphenyl)-N'-(1-pyrenyl)-3,3',5,5'-tetramethylbenzidine (m.p. 198.0°-19... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Tertiary amine | c1ccccc1.c1ccccc1.c1cc2ccc3cccc4ccc(c1)c2c34 | c1ccccc1.c1ccccc1.c1cc2ccc3cccc4ccc(c1)c2c34 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cc2ccc3cccc4ccc(c1)c2c34 | HI | null | null | null | CC(=O)N(c1ccc(C)cc1)c1c(C)cc(-c2cc(C)c(N(c3ccc(C)cc3)c3ccc(C)cc3)c(C)c2)cc1C.Ic1ccc2ccc3cccc4ccc1c2c34>>Cc1ccc(N(c2ccc(C)cc2)c2c(C)cc(-c3cc(C)c(N(c4ccc(C)cc4)c4ccc5ccc6cccc7ccc4c5c67)c(C)c3)cc2C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e78636ac392648f09d0669cfa8fe54aa | CI.[O-][N+]12CCN(CC1)CC2>>CO[N+]12CCN(CC1)CC2 | [NH+]12CC[NH+](CC1)CC2.OO.F[B-](F)(F)F.[Na+].N12CC[N+](CC1)(CC2)[O-].IC>>F[B-](F)(F)F.CO[N+]12CCN(CC1)CC2 | I[CH3:1].[O-:2][N+:3]12[CH2:4][CH2:5][N:6]([CH2:7][CH2:8]1)[CH2:9][CH2:10]2>>[CH3:1][O:2][N+:3]12[CH2:4][CH2:5][N:6]([CH2:7][CH2:8]1)[CH2:9][CH2:10]2 | CI.[O-][N+]12CCN(CC1)CC2 | CO[N+]12CCN(CC1)CC2 | null | null | C(C)#N.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | cfc4d393b18fb7b5f05de5e040c37ca84bbb5ffbae4c339ecdbeec57febd1df9 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | C1C[NH+]2CCN1CC2 | I-[CH3;D1;+0:1].[C:2]-[#7;+:3](-[O-;H0;D1:4])(-[C:5])-[C:6]>>[C:2]-[#7;+:3](-[O;H0;D2;+0:4]-[CH3;D1;+0:1])(-[C:5])-[C:6] | null | [] | null | null | 8 | HOUR | 1-fluoro-4-methoxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazoniabicyclo[2.2.2]octane N-oxide is prepared by the reaction of 1,4-Diazoniabicyclo[2.2.2]octane with hydrogen peroxide as described by Farkas in J. Chem. Eng. Data (1968) 13, 278. 1,4-Diazabicyclo[2.2.2]octane N-oxide (12.8 g, 10 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH+]2CCN1CC2 | I- | C(C)#N.C1CCOC1 | null | 8 | CI.[O-][N+]12CCN(CC1)CC2>C(C)#N.C1CCOC1>CO[N+]12CCN(CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9dab11d5aff5437cb48a5714a3f1d62a | CO[N+]12CCN(CC1)CC2.FB(F)F.FF>>CO[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F | F[B-](F)(F)F.CO[N+]12CCN(CC1)CC2.B(F)(F)F.FF>>F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CC1)(CC2)OC | [CH3:1][O:2][N+:3]12[CH2:4][CH2:5][N:6]([CH2:8][CH2:9]1)[CH2:10][CH2:11]2.[F:17][B:18]([F:19])[F:21].[F:7][F:20]>>[CH3:1][O:2][N+:3]12[CH2:4][CH2:5][N+:6]([F:7])([CH2:8][CH2:9]1)[CH2:10][CH2:11]2.[F:17][B-:18]([F:19])([F:20])[F:21] | CO[N+]12CCN(CC1)CC2.FB(F)F.FF | CO[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F | null | null | C(C)#N | Functional Group Addition | OtherReaction | 9a2b2ee8108a10e239d78a2d3fd320889b8b6d409487df4d172792fde2b0eef9 | ebfc24bc16327acaf052273ff375d776ddf266b8dcfd4f3c222c8ab0d1a45110 | C1C[NH+]2CC[NH+]1CC2 | [C:1]1-[C:2]-[#7;+:3]2-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[C:7]-[C:8]-2.[F;D1;H0:9]-[B;H0;D3;+0:10](-[F;D1;H0:11])-[F;D1;H0:12].[F;H0;D1;+0:13]-[F;H0;D1;+0:14]>>[F;D1;H0:9]-[B-;H0;D4:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;H0;D1;+0:13].[F;H0;D1;+0:14]-[N+;H0;D4:6]12-[C:1]-[C:2]-[#7;+:3](-[C:4]-[C:5]-1)-[C:8]-[C:7]-2 | null | [] | null | null | null | null | A solution of 1-methoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate (23 g, 10 mmole) and boron trifluoride gas (6.7 g, 10 mmole) in acetonitrile (125 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10 % V/V, 12 mmole). The reaction was evaporated, the remaining solid washed with DME... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1C[NH+]2CCN1CC2 | C1C[NH+]2CC[NH+]1CC2 | C1C[NH+]2CC[NH+]1CC2 | null | C(C)#N | null | null | CO[N+]12CCN(CC1)CC2.FB(F)F.FF>C(C)#N>CO[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f9e0c9f2c0c944d59a70ae8393a741c1 | C1CN2CCN1CC2.CC(=O)Cl.F[B-](F)(F)F.OO.[O-][N+]12CCN(CC1)CC2>>CC(=O)O[N+]12CCN(CC1)CC2.CC(=O)O[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F.F[B-](F)(F)F.F[B-](F)(F)F.[O-][N+]12CCN(CC1)CC2 | N12CCN(CC1)CC2.OO.F[B-](F)(F)F.[Na+].N12CC[N+](CC1)(CC2)[O-].C(C)(=O)Cl>>N12CC[N+](CC1)(CC2)[O-].F[B-](F)(F)F.F[B-](F)(F)F.C(C)(=O)O[N+]21CC[N+](CC2)(CC1)F.F[B-](F)(F)F.C(C)(=O)O[N+]12CCN(CC1)CC2 | [CH2:13]1[CH2:14][N:17]2[CH2:18][CH2:44][N:45]1[CH2:46][CH2:47]2.Cl[C:2]([CH3:1])=[O:3].[F:21][B-:27]([F:26])([F:30])[F:35].[OH:15][OH:16].[O-:4][N+:5]12[CH2:6][CH2:7][N:8]([CH2:9][CH2:10]1)[CH2:11][CH2:12]2>>[CH3:1][C:2](=[O:3])[O:4][N+:5]12[CH2:6][CH2:7][N:8]([CH2:9][CH2:10]1)[CH2:11][CH2:12]2.[CH3:13][C:14](=[O:15])... | C1CN2CCN1CC2.CC(=O)Cl.F[B-](F)(F)F.OO.[O-][N+]12CCN(CC1)CC2 | CC(=O)O[N+]12CCN(CC1)CC2.CC(=O)O[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F.F[B-](F)(F)F.F[B-](F)(F)F.[O-][N+]12CCN(CC1)CC2 | null | null | C(C)#N.C1CCOC1 | Acylation | OtherReaction | 703c3e1e589061a99cc1c70990e32ab70a1d8cce27928de70c74f5b1c58602fb | d71a2e2e42314dfb8171251fc474d0e072bc1e5b43f7f690eafed5883d419b35 | C1C[NH+]2CCN1CC2.C1C[NH+]2CCN1CC2.C1C[NH+]2CC[NH+]1CC2 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#7;+:5](-[O-;H0;D1:6])(-[C:7])-[C:8].[C:9]1-[CH2;D2;+0:10]-[N;H0;D3;+0:11]2-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[N;H0;D3;+0:14]-1-[CH2;D2;+0:15]-[CH2;D2;+0:16]-2.[F;D1;H0:17]-[B-;H0;D4:18](-[F;D1;H0:19])(-[F;H0;D1;+0:20])-[F;H0;D1;+0:21].[OH;D1;+0:22]-[OH;D1;+0:23]>>[CH3;D1;... | null | [] | null | null | 8 | HOUR | 1-acetoxy-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazabicyclo[2.2.2]octane N-oxide is prepared by the reaction of 1,4-diazabicyclo[2.2.2]octane with hydrogen peroxide as described by Farkas in J. Chem. Eng. Data (1968) 13,278. 1,4-Diazabicyclo[2.2.2]octane N-oxide (12.8 g, 10 mmol) in THF ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amine.Tertiary amine.Peroxide | Tertiary amine | C1CN2CCN1CC2 | C1C[NH+]2CC[NH+]1CC2.C1C[NH+]2CCN1CC2 | C1C[NH+]2CCN1CC2.C1C[NH+]2CC[NH+]1CC2.C1C[NH+]2CCN1CC2 | null | C(C)#N.C1CCOC1 | null | 8 | C1CN2CCN1CC2.CC(=O)Cl.F[B-](F)(F)F.OO.[O-][N+]12CCN(CC1)CC2>C(C)#N.C1CCOC1>CC(=O)O[N+]12CCN(CC1)CC2.CC(=O)O[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F.F[B-](F)(F)F.F[B-](F)(F)F.[O-][N+]12CCN(CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ab4216995e4549fa8ff7ec48a60a94aa | CC(=O)O[N+]12CCN(CC1)CC2.FB(F)F.FF>>CC(=O)O[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F | F[B-](F)(F)F.C(C)(=O)O[N+]12CCN(CC1)CC2.B(F)(F)F.FF>>F[B-](F)(F)F.F[B-](F)(F)F.C(C)(=O)O[N+]12CC[N+](CC1)(CC2)F | [CH3:1][C:2](=[O:3])[O:4][N+:5]12[CH2:6][CH2:7][N:8]([CH2:10][CH2:11]1)[CH2:12][CH2:13]2.[F:19][B:20]([F:21])[F:23].[F:9][F:22]>>[CH3:1][C:2](=[O:3])[O:4][N+:5]12[CH2:6][CH2:7][N+:8]([F:9])([CH2:10][CH2:11]1)[CH2:12][CH2:13]2.[F:19][B-:20]([F:21])([F:22])[F:23] | CC(=O)O[N+]12CCN(CC1)CC2.FB(F)F.FF | CC(=O)O[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F | null | null | C(C)#N | Functional Group Addition | OtherReaction | 9a2b2ee8108a10e239d78a2d3fd320889b8b6d409487df4d172792fde2b0eef9 | ebfc24bc16327acaf052273ff375d776ddf266b8dcfd4f3c222c8ab0d1a45110 | C1C[NH+]2CC[NH+]1CC2 | [C:1]1-[C:2]-[#7;+:3]2-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[C:7]-[C:8]-2.[F;D1;H0:9]-[B;H0;D3;+0:10](-[F;D1;H0:11])-[F;D1;H0:12].[F;H0;D1;+0:13]-[F;H0;D1;+0:14]>>[F;D1;H0:9]-[B-;H0;D4:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;H0;D1;+0:13].[F;H0;D1;+0:14]-[N+;H0;D4:6]12-[C:1]-[C:2]-[#7;+:3](-[C:4]-[C:5]-1)-[C:8]-[C:7]-2 | null | [] | null | null | null | null | A solution of 1-acetoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate (25.8 g, 10 mmole) and boron trifluoride gas (6.7 g, 10 mmole) in acetonitrile (125 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10% V/V, 12 mmole). The reaction was evaporated, the remaining solid washed with di... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1C[NH+]2CCN1CC2 | C1C[NH+]2CC[NH+]1CC2 | C1C[NH+]2CC[NH+]1CC2 | null | C(C)#N | null | null | CC(=O)O[N+]12CCN(CC1)CC2.FB(F)F.FF>C(C)#N>CC(=O)O[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-25a11841b6164cf5bb6272caa2ef15ea | O=C(Cl)c1ccccc1.[O-][N+]12CCN(CC1)CC2>>O=C(c1ccccc1)[N+]12CCN(CC1)CC2 | N12CCN(CC1)CC2.OO.F[B-](F)(F)F.[Na+].N12CC[N+](CC1)(CC2)[O-].C(C1=CC=CC=C1)(=O)Cl>>F[B-](F)(F)F.C(C1=CC=CC=C1)(=O)[N+]12CCN(CC1)CC2 | Cl[C:7](=[O:6])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[O-][N+:14]12[CH2:15][CH2:16][N:17]([CH2:18][CH2:19]1)[CH2:20][CH2:21]2>>[O:6]=[C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[N+:14]12[CH2:15][CH2:16][N:17]([CH2:18][CH2:19]1)[CH2:20][CH2:21]2 | O=C(Cl)c1ccccc1.[O-][N+]12CCN(CC1)CC2 | O=C(c1ccccc1)[N+]12CCN(CC1)CC2 | null | null | C(C)#N.C1CCOC1 | Acylation | OtherReaction | 71de880c97bc17218c5bab0f660222c3e955b05414245d94c1c935c2fb2ce037 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(c1ccccc1)[N+]12CCN(CC1)CC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O-]-[N+;H0;D4:6]12-[C:7]-[C:8]-[#7:9](-[C:10]-[C:11]-1)-[C:12]-[C:13]-2>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[N+;H0;D4:6]12-[C:7]-[C:8]-[#7:9](-[C:10]-[C:11]-1)-[C:12]-[C:13]-2 | null | [] | null | null | 8 | HOUR | 1-benzoyl-4-fluoro-1,4-diazoniabicvclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazabicyclo[2.2.2]octane N-oxide is prepared by the reaction of 1,4-diazabicyclo[2.2.2]octane with hydrogen peroxide as described by Farkas in J. Chem. Eng. Data (1968) 13, 278. 1,4-Diazabicyclo[2.2.2]octane N-oxide (12.8 g, 10 mmool) in TH... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | C1C[NH+]2CCN1CC2 | C1C[NH+]2CCN1CC2 | c1ccccc1.C1C[NH+]2CCN1CC2 | Other | C(C)#N.C1CCOC1 | null | 8 | O=C(Cl)c1ccccc1.[O-][N+]12CCN(CC1)CC2>C(C)#N.C1CCOC1>O=C(c1ccccc1)[N+]12CCN(CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6e157c5c567247129f5adc0a91e8d8c5 | FB(F)F.FF.F[B-](F)(F)F.O=C(c1ccccc1)[N+]12CCN(CC1)CC2>>F[B-](F)(F)F.F[B-](F)(F)F.O=C(c1ccccc1)[N+]12CC[N+](F)(CC1)CC2 | F[B-](F)(F)F.C(C1=CC=CC=C1)(=O)[N+]12CCN(CC1)CC2.B(F)(F)F.FF>>F[B-](F)(F)F.F[B-](F)(F)F.C(C1=CC=CC=C1)(=O)[N+]12CC[N+](CC1)(CC2)F | [F:1][B:2]([F:3])[F:5].[F:9][F:23].[F:4][B-:7]([F:6])([F:8])[F:10].[O:11]=[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[N+:19]12[CH2:20][CH2:21][N:22]([CH2:24][CH2:25]1)[CH2:26][CH2:27]2>>[F:1][B-:2]([F:3])([F:4])[F:5].[F:6][B-:7]([F:8])([F:9])[F:10].[O:11]=[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[N+:1... | FB(F)F.FF.F[B-](F)(F)F.O=C(c1ccccc1)[N+]12CCN(CC1)CC2 | F[B-](F)(F)F.F[B-](F)(F)F.O=C(c1ccccc1)[N+]12CC[N+](F)(CC1)CC2 | null | null | C(C)#N | Functional Group Addition | OtherReaction | 9a2b2ee8108a10e239d78a2d3fd320889b8b6d409487df4d172792fde2b0eef9 | ebfc24bc16327acaf052273ff375d776ddf266b8dcfd4f3c222c8ab0d1a45110 | O=C(c1ccccc1)[N+]12CC[NH+](CC1)CC2 | [C:1]1-[C:2]-[N;H0;D3;+0:3]2-[C:4]-[C:5]-[#7;+:6]-1-[C:7]-[C:8]-2.[F;D1;H0:9]-[B-;H0;D4:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;H0;D1;+0:13].[F;D1;H0:14]-[B;H0;D3;+0:15](-[F;D1;H0:16])-[F;D1;H0:17].[F;H0;D1;+0:18]-[F;H0;D1;+0:19]>>[F;D1;H0:14]-[B-;H0;D4:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;H0;D1;+0:13].[F;D1;H0:9]-[B-;H0;... | null | [] | null | null | null | null | A solution of 1-benzoyl-4-aza-1-azoniabicyclo[2.2.2]octane tetrafiuoroborate (32 g, 10 mmole) and boron trifluoride gas (6.7 g, 10 mmole) in acetonitrile (125 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10 % V/V, 12 mmole). The reaction was evaporated, the remaining solid washed with DME... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1C[NH+]2CCN1CC2 | C1C[NH+]2CC[NH+]1CC2 | c1ccccc1.C1C[NH+]2CC[NH+]1CC2 | null | C(C)#N | null | null | FB(F)F.FF.F[B-](F)(F)F.O=C(c1ccccc1)[N+]12CCN(CC1)CC2>C(C)#N>F[B-](F)(F)F.F[B-](F)(F)F.O=C(c1ccccc1)[N+]12CC[N+](F)(CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-68b57b6ecab2412e9371a6258170f21b | O=S(=O)(O)[N+]12CC[N+](F)(CC1)CC2>>O=S(=O)(O)[N+]12CCN(CC1)CC2 | F[B-](F)(F)F.[Na+].N12CCN(CC1)CC2.F[B-](F)(F)F.F[B-](F)(F)F.F[N+]21CC[N+](CC2)(CC1)S(=O)(=O)O.ClS(=O)(=O)O>>F[B-](F)(F)F.S(=O)(=O)(O)[N+]12CCN(CC1)CC2 | F[N+:13]12[CH2:12][CH2:11][N+:10]([S:7](=[O:6])(=[O:8])[OH:9])([CH2:15][CH2:14]1)[CH2:17][CH2:16]2>>[O:6]=[S:7](=[O:8])([OH:9])[N+:10]12[CH2:11][CH2:12][N:13]([CH2:14][CH2:15]1)[CH2:16][CH2:17]2 | O=S(=O)(O)[N+]12CC[N+](F)(CC1)CC2 | O=S(=O)(O)[N+]12CCN(CC1)CC2 | null | null | C(C)#N.C1CCOC1 | Functional Group Interconversion | OtherReaction | 6fad9925d768aa43937f17c1eab71b6cb2435e24e29b514483b2e873f02a536c | 2fd09f345dff7e8b2bfcfb03c428878723839bdf04c463136343b38e7680dfc7 | C1C[NH+]2CCN1CC2 | F-[N+;H0;D4:1]12-[C:2]-[C:3]-[#7;+:4](-[C:5]-[C:6]-1)-[C:7]-[C:8]-2>>[C:3]1-[C:2]-[N;H0;D3;+0:1]2-[C:6]-[C:5]-[#7;+:4]-1-[C:7]-[C:8]-2 | null | [] | null | null | 8 | HOUR | 1-Fluoro-4-sulfo-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazabicyclo[2.2.2]octane (11 g, 10 mmol) in THF (100 mL) is reacted with chlorosulfonic acid (11.6 g, 10 mmol) until the reaction is complete by TLC. The reaction is evaporated, diluted with acetonitrile (100 mL) and sodium tetrafluoroborate ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1C[NH+]2CC[NH+]1CC2 | C1C[NH+]2CCN1CC2 | C1C[NH+]2CCN1CC2 | Other | C(C)#N.C1CCOC1 | null | 8 | O=S(=O)(O)[N+]12CC[N+](F)(CC1)CC2>C(C)#N.C1CCOC1>O=S(=O)(O)[N+]12CCN(CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8bd507f610d45d4aca5b13728993610 | FB(F)F.FF.O=S(=O)(O)[N+]12CCN(CC1)CC2>>F[B-](F)(F)F.O=S(=O)(O)[N+]12CC[N+](F)(CC1)CC2 | F[B-](F)(F)F.S(=O)(=O)(O)[N+]12CCN(CC1)CC2.B(F)(F)F.FF>>F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CC1)(CC2)S(=O)(=O)O | [F:1][B:2]([F:3])[F:5].[F:4][F:19].[O:11]=[S:12](=[O:13])([OH:14])[N+:15]12[CH2:16][CH2:17][N:18]([CH2:20][CH2:21]1)[CH2:22][CH2:23]2>>[F:1][B-:2]([F:3])([F:4])[F:5].[O:11]=[S:12](=[O:13])([OH:14])[N+:15]12[CH2:16][CH2:17][N+:18]([F:19])([CH2:20][CH2:21]1)[CH2:22][CH2:23]2 | FB(F)F.FF.O=S(=O)(O)[N+]12CCN(CC1)CC2 | F[B-](F)(F)F.O=S(=O)(O)[N+]12CC[N+](F)(CC1)CC2 | null | null | C(C)#N | Functional Group Addition | OtherReaction | 9a2b2ee8108a10e239d78a2d3fd320889b8b6d409487df4d172792fde2b0eef9 | ebfc24bc16327acaf052273ff375d776ddf266b8dcfd4f3c222c8ab0d1a45110 | C1C[NH+]2CC[NH+]1CC2 | [C:1]1-[C:2]-[N;H0;D3;+0:3]2-[C:4]-[C:5]-[#7;+:6]-1-[C:7]-[C:8]-2.[F;D1;H0:9]-[B;H0;D3;+0:10](-[F;D1;H0:11])-[F;D1;H0:12].[F;H0;D1;+0:13]-[F;H0;D1;+0:14]>>[F;D1;H0:9]-[B-;H0;D4:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;H0;D1;+0:14].[F;H0;D1;+0:13]-[N+;H0;D4:3]12-[C:2]-[C:1]-[#7;+:6](-[C:5]-[C:4]-1)-[C:7]-[C:8]-2 | null | [] | null | null | null | null | A solution of 1-sulfo-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate (28 g, 10 mmole) and boron trifluoride gas (6.7 g, 10 mmole) in acetonitrile (125 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10% V/V, 12 mmole). The reaction was evaporated, the remaining solid washed with DME an... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1C[NH+]2CCN1CC2 | C1C[NH+]2CC[NH+]1CC2 | C1C[NH+]2CC[NH+]1CC2 | null | C(C)#N | null | null | FB(F)F.FF.O=S(=O)(O)[N+]12CCN(CC1)CC2>C(C)#N>F[B-](F)(F)F.O=S(=O)(O)[N+]12CC[N+](F)(CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7aa01f68f6ca4bfb93c17f6e95f142b9 | CS(=O)(=O)[N+]12CC[N+](F)(CC1)CC2>>CS(=O)(=O)[N+]12CCN(CC1)CC2 | F[B-](F)(F)F.[Na+].N12CCN(CC1)CC2.F[B-](F)(F)F.F[B-](F)(F)F.F[N+]21CC[N+](CC2)(CC1)S(=O)(=O)C.CS(=O)(=O)Cl>>F[B-](F)(F)F.CS(=O)(=O)[N+]12CCN(CC1)CC2 | F[N+:8]12[CH2:7][CH2:6][N+:5]([S:2]([CH3:1])(=[O:3])=[O:4])([CH2:10][CH2:9]1)[CH2:12][CH2:11]2>>[CH3:1][S:2](=[O:3])(=[O:4])[N+:5]12[CH2:6][CH2:7][N:8]([CH2:9][CH2:10]1)[CH2:11][CH2:12]2 | CS(=O)(=O)[N+]12CC[N+](F)(CC1)CC2 | CS(=O)(=O)[N+]12CCN(CC1)CC2 | null | null | O1CCCC1.C(C)#N | Functional Group Interconversion | OtherReaction | 6fad9925d768aa43937f17c1eab71b6cb2435e24e29b514483b2e873f02a536c | 2fd09f345dff7e8b2bfcfb03c428878723839bdf04c463136343b38e7680dfc7 | C1C[NH+]2CCN1CC2 | F-[N+;H0;D4:1]12-[C:2]-[C:3]-[#7;+:4](-[C:5]-[C:6]-1)-[C:7]-[C:8]-2>>[C:5]1-[C:6]-[N;H0;D3;+0:1]2-[C:2]-[C:3]-[#7;+:4]-1-[C:7]-[C:8]-2 | null | [] | null | null | 8 | HOUR | 1-Fluoro-4-methanesulfonyl-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazabicyclo[2.2.2]octane (11 g, 10 mmol) in tetrahydrofuran (100 mL) is reacted with methanesulfonyl chloride (11.5 g, 10 mmol) until the reaction is complete by TLC. The reaction is evaporated, diluted with acetonitrile (100 mL) an... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1C[NH+]2CC[NH+]1CC2 | C1C[NH+]2CCN1CC2 | C1C[NH+]2CCN1CC2 | Other | O1CCCC1.C(C)#N | null | 8 | CS(=O)(=O)[N+]12CC[N+](F)(CC1)CC2>O1CCCC1.C(C)#N>CS(=O)(=O)[N+]12CCN(CC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aa05a8bb5ab643cdbd1c7d8827e3a981 | CCC1(CC)C[N+]2(P(=O)(O)O)CC[N+]1(F)CC2>>CCC1(CC)CN2CC[N+]1(P(=O)(O)O)CC2 | F[B-](F)(F)F.[Na+].[NH+]12CC[NH+](CC1)CC2.F[B-](F)(F)F.F[B-](F)(F)F.C(C)C2([N+]1(CC[N+](C2)(CC1)P(=O)(O)O)F)CC.P(=O)(OCC)(OCC)Cl>>F[B-](F)(F)F.C(C)C1([N+]2(CCN(C1)CC2)P(=O)(O)O)CC | F[N+:10]12[C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[CH2:6][N+:7]([P:11](=[O:12])([OH:13])[OH:14])([CH2:8][CH2:9]1)[CH2:16][CH2:15]2>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[CH2:6][N:7]2[CH2:8][CH2:9][N+:10]1([P:11](=[O:12])([OH:13])[OH:14])[CH2:15][CH2:16]2 | CCC1(CC)C[N+]2(P(=O)(O)O)CC[N+]1(F)CC2 | CCC1(CC)CN2CC[N+]1(P(=O)(O)O)CC2 | null | null | C(C)#N.C1CCOC1 | Functional Group Interconversion | OtherReaction | 6fad9925d768aa43937f17c1eab71b6cb2435e24e29b514483b2e873f02a536c | 2fd09f345dff7e8b2bfcfb03c428878723839bdf04c463136343b38e7680dfc7 | C1C[NH+]2CCN1CC2 | F-[N+;H0;D4:1]12-[C:2]-[C:3]-[N+;H0;D4:4](-[P;H0;D4;+0:5](=[O;D1;H0:6])(-[O;D1;H1:7])-[O;D1;H1:8])(-[C:9]-[C:10]-1(-[C:11])-[C:12])-[C:13]-[C:14]-2>>[C:11]-[C:10]1(-[C:12])-[C:9]-[N;H0;D3;+0:4]2-[C:3]-[C:2]-[N+;H0;D4:1]-1(-[P;H0;D4;+0:5](=[O;D1;H0:6])(-[O;D1;H1:7])-[O;D1;H1:8])-[C:14]-[C:13]-2 | null | [] | null | null | 8 | HOUR | Diethyl 1-Fluoro-4-phosphono-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazoniabicyclo[2.2.2]octane (11 g, 10 mmol) in THF (100 mL) is reacted with diethyl chlorophosphate (17.3 g, 10 mmol) until the reaction is complete by TLC. The reaction is evaporated, diluted with acetonitrile (100 mL) and sodium... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1C[NH+]2CC[NH+]1CC2 | C1C[NH+]2CCN1CC2 | C1C[NH+]2CCN1CC2 | Other | C(C)#N.C1CCOC1 | null | 8 | CCC1(CC)C[N+]2(P(=O)(O)O)CC[N+]1(F)CC2>C(C)#N.C1CCOC1>CCC1(CC)CN2CC[N+]1(P(=O)(O)O)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3db210e326114ffbb72dd55072cee33b | C=C(C)c1ccccc1.O[N+]12CC[N+](F)(CC1)CC2>>CC(O)(CF)c1ccccc1 | CC(=C)C1=CC=CC=C1.O.F[B-](F)(F)F.F[B-](F)(F)F.O[N+]12CC[N+](CC1)(CC2)F>>FCC(C)(C1=CC=CC=C1)O | [CH3:1][C:2](=[CH2:4])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.F[N+]12CC[N+]([OH:3])(CC1)CC2>>[CH3:1][C:2]([OH:3])([CH2:4][F:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | C=C(C)c1ccccc1.O[N+]12CC[N+](F)(CC1)CC2 | CC(O)(CF)c1ccccc1 | null | null | C(C)#N.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 46b7695be5005273e85897ed2f48c198c50649ae503a8f1bd0e858144904e1df | c553246979db295cb69b2b4e0150b7fc8770a228924e032e0183857e216e6eb5 | c1ccccc1 | F-[N+]12-C-C-[N+](-[OH;D1;+0:1])(-C-C-1)-C-C-2.[C;D1;H3:2]-[C;H0;D3;+0:3](=[CH2;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D4;+0:3](-[OH;D1;+0:1])(-[CH2;D2;+0:4]-[F;D1;H0:8])-[c:5](:[c:6]):[c:7] | 71.3 | [{"value": 71.0, "product": "FCC(C)(C1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "FCC(C)(C1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of alpha-methylstyrene (0.13 mL, 1 mmole) and water (0.02 mL, 1.1 mmole) in acetonitrile (10 mL) was added 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (330 mg, 1.02 mmole 1.02 equ.) and the reaction stirred at room temperature for 24 h. The mixture was diluted with ether (2... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | Primary halide.Tertiary alcohol | C1C[NH+]2CC[NH+]1CC2 | null | c1ccccc1 | HF | C(C)#N.CCOCC | null | 24 | C=C(C)c1ccccc1.O[N+]12CC[N+](F)(CC1)CC2>C(C)#N.CCOCC>CC(O)(CF)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-083499c985844daa96570d10ad6ea15e | CC(=O)OC(C)(C)C.C[Si](C)(C)C#CC=N[Si](C)(C)C>>CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C | C[Si](N=CC#C[Si](C)(C)C)(C)C.C(C)(=O)OC(C)(C)C.[Li]>>NC(CC(=O)OC(C)(C)C)C#C[Si](C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH3:8].C[Si](C)(C)[N:10]=[CH:9][C:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([NH2:10])[C:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16] | CC(=O)OC(C)(C)C.C[Si](C)(C)C#CC=N[Si](C)(C)C | CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C | null | null | null | C-C Coupling | OtherReaction | e12b58a1278d56f6b0b0849c9cdbc204c745bf3e4107d2078c5c79261445d74d | cfce763bd5eadcead5800269e2dbdd0bf805187ef1e73fdb1b582edfe017430a | null | C-[Si](-C)(-C)-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[C:3]#[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:13]-[C:14](-[CH3;D1;+0:15])=[O;D1;H0:16]>>[C;D1;H3:6]-[#14:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[C:4]#[C:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[CH2;D2;+0:15]-[C:14](=[O;D1;H0:1... | null | [] | null | null | null | null | The present invention relates to a novel process for the preparation of ethyl 3S-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-pentynoate having the following structural formula ##STR1## and the pharmaceutically acceptable acid addition salt thereof which comprises treating (trimethylsilyl) acetylene ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Silyl protective group | Ester.Primary amine | null | null | null | Other | null | null | null | CC(=O)OC(C)(C)C.C[Si](C)(C)C#CC=N[Si](C)(C)C>>CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0336511949d74665bed4608e05b7d128 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | C1(CCC(=O)O1)=O.Cl.Cl.NC1=CC=C(C(=N)N)C=C1.CN(C)C1=NC=CC=C1.CN(C)C=O>>NN=CC1=CC=C(C=C1)NC(CCC(=O)O)=O | [NH2:1][C:3](=[NH:2])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:16][cH:17]1.[C:9]1(=[O:10])[CH2:11][CH2:12][C:13](=[O:14])[O:15]1>>[NH2:1][N:2]=[CH:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[CH2:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17]1 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1 | NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | null | null | N1=CC=CC=C1 | Protection | OtherReaction | 8e75bdde89622f8a79182425dce03ce5da54a59b1e74cfa93c1444de0bccfe22 | bbca7274612101b244a95a65cae326386be2318abf182063d6ec3133b746838d | c1ccccc1 | [NH2;D1;+0:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]:[c:10]:1.[O;D1;H0:11]=[C;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-1>>[NH2;D1;+0:1]-[N;H0;D2;+0:3]=[CH;D2;+0:2]-[c:4]1:[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:12](=[O;D1;H0:11])-[C:13]-[C:14]-[C:15](=[... | 88 | [{"value": 88.0, "product": "NN=CC1=CC=C(C=C1)NC(CCC(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | U.S. Pat. No. 5,344,957 discloses a process for preparing ethyl 3S 3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-pentynoate having the following formula ##STR2## This process is described as follows: 4-Aminobenzamidine di-HCl (25 g, 120 mmol), which is commercially available, particularly from Aldri... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine.Primary amine | Hydrazone.Carboxylic acid.Secondary amide | C1CCOC1 | null | c1ccccc1 | null | N1=CC=CC=C1 | 100 | 1 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>N1=CC=CC=C1>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5a6738c6e3e64ced845e39bbb9e836f6 | C#C[C@@H](N)CC(=O)OCC.NN=Cc1ccc(NC(=O)CCC(=O)O)cc1>>C#C[C@H](CC(=O)OCC)NC(=O)CCC(=O)Nc1ccc(C=NN)cc1 | N[C@@H](CC(=O)OCC)C#C.CN(C)C1=NC=CC=C1.CN1CCOCC1.ClC(=O)OCC(C)C.C(C)(C)N(CC)C(C)C.Cl.NN=CC1=CC=C(C=C1)NC(CCC(=O)O)=O>>NN=CC1=CC=C(C=C1)NC(CCC(=O)N[C@@H](CC(=O)OCC)C#C)=O | [CH:1]#[C:2][C@H:3]([CH2:4][C:5](=[O:6])[O:7][CH2:8][CH3:9])[NH2:10].O[C:11](=[O:12])[CH2:13][CH2:14][C:15](=[O:16])[NH:17][c:18]1[cH:19][cH:20][c:21]([CH:22]=[N:23][NH2:24])[cH:25][cH:26]1>>[CH:1]#[C:2][C@H:3]([CH2:4][C:5](=[O:6])[O:7][CH2:8][CH3:9])[NH:10][C:11](=[O:12])[CH2:13][CH2:14][C:15](=[O:16])[NH:17][c:18]1[c... | C#C[C@@H](N)CC(=O)OCC.NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | C#C[C@H](CC(=O)OCC)NC(=O)CCC(=O)Nc1ccc(C=NN)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5](-[#7:6])=[O;D1;H0:7].[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]#[C;D1;H1:15]>>[#7:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12](-[C:14]#[C;D1;H1:15])-[C:11]-[C:9](-[#8:8])=[O;D1;H0:10] | null | [] | null | null | 1 | HOUR | 4-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid hydrochloride was added to dry DMF (35 ml) followed by N-methylmorpholine (0.39 g, 1 eq.) and isobutyl chloroformate (0.53 g, 3.9 mmol) at 25° C. The mixture was stirred for 5 min. (S)-ethyl 3-amino-4-pentynoate was added followed by diisopropylethylamine and a c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C)C=O | null | 1 | C#C[C@@H](N)CC(=O)OCC.NN=Cc1ccc(NC(=O)CCC(=O)O)cc1>CN(C)C=O>C#C[C@H](CC(=O)OCC)NC(=O)CCC(=O)Nc1ccc(C=NN)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f3d8672c7b4740019655c7da6ddf3f18 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | Cl.Cl.NC1=CC=C(C(=N)N)C=C1.C1(CCC(=O)O1)=O.N1=CC=CC=C1>>Cl.NN=CC1=CC=C(C=C1)NC(CCC(=O)O)=O | [NH2:2][C:4](=[NH:3])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:17][cH:18]1.[C:10]1(=[O:11])[CH2:12][CH2:13][C:14](=[O:15])[O:16]1>>[NH2:2][N:3]=[CH:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH2:13][C:14](=[O:15])[OH:16])[cH:17][cH:18]1 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1 | NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | null | null | null | Protection | OtherReaction | 8e75bdde89622f8a79182425dce03ce5da54a59b1e74cfa93c1444de0bccfe22 | bbca7274612101b244a95a65cae326386be2318abf182063d6ec3133b746838d | c1ccccc1 | [NH2;D1;+0:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]:[c:10]:1.[O;D1;H0:11]=[C;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-1>>[NH2;D1;+0:1]-[N;H0;D2;+0:3]=[CH;D2;+0:2]-[c:4]1:[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:12](=[O;D1;H0:11])-[C:13]-[C:14]-[C:15](=[... | null | [] | null | null | null | null | treating 4-aminobenzamidine dihydrochloride with succinic anhydride and pyridine in the presence of an aprotic solvent to give 4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid, monohydrochloride;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine.Primary amine | Hydrazone.Carboxylic acid.Secondary amide | C1CCOC1 | null | c1ccccc1 | null | null | null | null | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-83206fb71f6a4ec4b4672167c536c0a0 | C[Si](C)(C)C#CC=O.C[Si](C)(C)[N-][Si](C)(C)C>>C[Si](C)(C)C#CC=N[Si](C)(C)C | C[Si](C)(C)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si](C#CC=O)(C)C.C[Si](C#CC=O)(C)C>>C[Si](N=CC#C[Si](C)(C)C)(C)C | O=[CH:7][C:6]#[C:5][Si:2]([CH3:1])([CH3:3])[CH3:4].C[Si](C)(C)[N-:8][Si:9]([CH3:10])([CH3:11])[CH3:12]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][CH:7]=[N:8][Si:9]([CH3:10])([CH3:11])[CH3:12] | C[Si](C)(C)C#CC=O.C[Si](C)(C)[N-][Si](C)(C)C | C[Si](C)(C)C#CC=N[Si](C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | faa9f772dbb5a322de6abb99039ea64dd15f25da575ca90a6647b0f75551cbe9 | 0931318a6f4f3dcd59c6eec5ddf0be00c2acf33bccb0313556ca2ced61107d8c | null | C-[Si](-C)(-C)-[N-;H0;D2:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].O=[CH;D2;+0:6]-[C:7]#[C:8]-[#14:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:3]-[#14:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[N;H0;D2;+0:1]=[CH;D2;+0:6]-[C:7]#[C:8]-[#14:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12] | null | [] | null | null | 1 | HOUR | Lithium bis(trimethylsilyl)amide is placed in a reaction vessel to which 3-(trimethylsilyl)-2-propynal of step 1 is added in an aprotic solvent. During the addition of 3-(trimethylsilyl)-2-propynal the pot temperature should be maintained between -40° to -20° C. to ensure stability of the intermediate imine. To the res... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Silyl protective group | null | null | null | null | HO- | null | null | 1 | C[Si](C)(C)C#CC=O.C[Si](C)(C)[N-][Si](C)(C)C>>C[Si](C)(C)C#CC=N[Si](C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e29c9d8d80024715a14e3f5f379de7a0 | CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C>>CCOC(=O)CC(N)C#C[Si](C)(C)C | C1(=CC=C(C=C1)S(=O)(=O)O)C.NC(CC(=O)OC(C)(C)C)C#C[Si](C)(C)C>>NC(CC(=O)OCC)C#C[Si](C)(C)C | C[C:2](C)([CH3:1])[O:3][C:4](=[O:5])[CH2:6][CH:7]([NH2:8])[C:9]#[C:10][Si:11]([CH3:12])([CH3:13])[CH3:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([NH2:8])[C:9]#[C:10][Si:11]([CH3:12])([CH3:13])[CH3:14] | CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C | CCOC(=O)CC(N)C#C[Si](C)(C)C | null | null | C(C)O | Miscellaneous | OtherReaction | 65c8f61c086a235ce6692c51186a0187b2fa4d47add33293a3d7824255d1a4bf | 019584698d6f4e780dc33c58bbe427f505956c44d516240fec11049769c33a01 | null | C-[C;H0;D4;+0:1](-C)(-[C;D1;H3:2])-[#8:3]-[C:4](-[C:5])=[O;D1;H0:6]>>[C:5]-[C:4](=[O;D1;H0:6])-[#8:3]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | The p-toluenesulfonic acid salt of (±)1,1-dimethylethyl 3-amino-5-(trimethylsilyl)-4-pentynoate is prepared by treating p-toluenesulfonic acid with (±)1,1-dimethylethyl 3-amino-5-(trimethylsilyl)-4-pentynoate, the product of step 2, in the presence of MTBE/heptane. The resulting reaction mixture is then heated to 55°-6... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Ester | null | null | null | Other | C(C)O | null | null | CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C>C(C)O>CCOC(=O)CC(N)C#C[Si](C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5568f7cc89bc405daea99df6a1ff9237 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | Cl.Cl.NC1=CC=C(C(=N)N)C=C1.C1(CCC(=O)O1)=O.CN(C=O)C>>NN=CC1=CC=C(C=C1)NC(CCC(=O)O)=O | [NH:1]=[C:3]([NH2:2])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:16][cH:17]1.[C:9]1(=[O:10])[CH2:11][CH2:12][C:13](=[O:14])[O:15]1>>[NH2:1][N:2]=[CH:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[CH2:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17]1 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1 | NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | null | null | N1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 0efda3125923bf2a936eb2c1eba12d21a060ae26fe0a0928161c20c9f96e5340 | c8bb9095a4bf98a907a33f4867f07e829799a21a0b4989f34ef70774121d881a | c1ccccc1 | [NH2;D1;+0:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]:[c:10]:1.[O;D1;H0:11]=[C;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-1>>[NH2;D1;+0:3]-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:4]1:[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:12](=[O;D1;H0:11])-[C:13]-[C:14]-[C:15](=[... | null | [] | null | null | null | null | Treatment of 4-aminobenzamidine dihydrochloride, which is commercially available, with succinic anhydride in the presence of N,N-dimethylformamide and pyridine gives 4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid, as a mixture of the zwitterion and the hydrochloride. The product is isolated from the crude rea... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine.Primary amine | Hydrazone.Carboxylic acid.Secondary amide | C1CCOC1 | null | c1ccccc1 | null | N1=CC=CC=C1 | null | null | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>N1=CC=CC=C1>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-51f57e41c82d40279e4c1b4a9b0d5bcf | CC(=O)OC(C)(C)C.C[Si](C)(C)C#CC=O.C[Si](C)(C)[N-][Si](C)(C)C>>CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C | C[Si](C)(C)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si](C#CC=O)(C)C.C(C)(=O)OC(C)(C)C>>NC(CC(=O)OC(C)(C)C)C#C[Si](C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH3:8].O=[CH:9][C:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16].C[Si](C)(C)[N-:10][Si](C)(C)C>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]([NH2:10])[C:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16] | CC(=O)OC(C)(C)C.C[Si](C)(C)C#CC=O.C[Si](C)(C)[N-][Si](C)(C)C | CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C | null | null | CC(C)(C)OC | Heteroatom Alkylation and Arylation | OtherReaction | 8f88de56d244d42c012e215fa78f141749b5e7458e721caa832eb07cda06f187 | ae288c239c1d5608cd0bd4aefb24be1419ca1dc0f2c1f82fdf34fcc78a01803d | null | C-[Si](-C)(-C)-[N-;H0;D2:1]-[Si](-C)(-C)-C.O=[CH;D2;+0:2]-[C:3]#[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:13]-[C:14](-[CH3;D1;+0:15])=[O;D1;H0:16]>>[C;D1;H3:6]-[#14:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[C:4]#[C:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[CH2;D2;+0:15]-[C:... | null | [] | -20 | CELSIUS | 10 | MINUTE | To a 500 mL, 3-neck round bottom flask equipped with a mechanical stirrer and under a blanket of nitrogen was charged 110 mL of lithium bis(trimethylsilyl)amide (1.0M solution in THF) while maintaining the internal temperature at -20° C. using an isopropanol/dry ice bath. Once the desired temperature was attained, 20.1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Silyl protective group.Silyl protective group | Ester.Primary amine | null | null | null | HO- | CC(C)(C)OC | -20 | 0.166667 | CC(=O)OC(C)(C)C.C[Si](C)(C)C#CC=O.C[Si](C)(C)[N-][Si](C)(C)C>CC(C)(C)OC>CC(C)(C)OC(=O)CC(N)C#C[Si](C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c3ffda7153b1440c87f670af1d6f0837 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | Cl.Cl.NC1=CC=C(C(=N)N)C=C1.C1(CCC(=O)O1)=O.CN(C)C=O.Cl>>Cl.NN=CC1=CC=C(C=C1)NC(CCC(=O)O)=O | [NH2:2][C:4](=[NH:3])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:17][cH:18]1.[C:10]1(=[O:11])[CH2:12][CH2:13][C:14](=[O:15])[O:16]1>>[NH2:2][N:3]=[CH:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH2:13][C:14](=[O:15])[OH:16])[cH:17][cH:18]1 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1 | NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 | null | null | N1=CC=CC=C1.CC(=O)C | Protection | OtherReaction | 8e75bdde89622f8a79182425dce03ce5da54a59b1e74cfa93c1444de0bccfe22 | bbca7274612101b244a95a65cae326386be2318abf182063d6ec3133b746838d | c1ccccc1 | [NH2;D1;+0:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]:[c:10]:1.[O;D1;H0:11]=[C;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-1>>[NH2;D1;+0:1]-[N;H0;D2;+0:3]=[CH;D2;+0:2]-[c:4]1:[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:12](=[O;D1;H0:11])-[C:13]-[C:14]-[C:15](=[... | null | [] | 100 | CELSIUS | 30 | MINUTE | A mixture of 2.2 g of 4-aminobenzamidine dihydrochloride, 1.1 g of succinic anhydride and 10 mL of DMF was stirred at ambient temperature for 15 min at which time 0.83 mL of pyridine was added all at once. The resulting heterogeneous mixture was warmed to 100° C. and maintained at 100° C. for 1.5 h. The disappearance o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine.Primary amine | Hydrazone.Carboxylic acid.Secondary amide | C1CCOC1 | null | c1ccccc1 | null | N1=CC=CC=C1.CC(=O)C | 100 | 0.5 | N=C(N)c1ccc(N)cc1.O=C1CCC(=O)O1>N1=CC=CC=C1.CC(=O)C>NN=Cc1ccc(NC(=O)CCC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-137e77f4fa5648b798903d6feabaa5a7 | CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1>>CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@@H](N)Cc1ccccc1 | C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(C)=O)O>>N[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(C)=O)O | c1ccc(C[N:17](Cc2ccccc2)[C@H:16]([C@H:14]([CH2:13][C@@H:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[OH:15])[CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)cc1>>[CH3:1][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)[CH2:13][C@H:14]([OH:15])[C@@H:16]([NH... | CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 | CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@@H](N)Cc1ccccc1 | null | [C].[Pd] | CO | Deprotection | OtherReaction | 2d0141567e42eb1f1e525678ba93b1f94e67edd4ce8af946d59aa7922040fcc6 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | c1ccc(CCCCCCc2ccccc2)cc1 | [C:1]-[C:2](-[C:3])-[N;H0;D3;+0:4](-C-c1:c:c:c:c:c:1)-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](-[C:3])-[NH2;D1;+0:4] | null | [] | 30 | CELSIUS | 30 | HOUR | To a solution of 100 g of (2S,3S,5S)-2-(N,N-dibenzylamino)-5-acetylamino-1,6-diphenyl-3-hexanol in 500 ml of methanol, was added 5 g of 5%-palladium-carbon (product of N. E. Chemcat), and the reaction mixture was stirred at 30° C. for 30 hours under a hydrogen atmosphere of 10 atm.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | [C].[Pd].CO | 30 | 30 | CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1>[C].[Pd].CO>CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@@H](N)Cc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-642869a01d1f43c7ae05158689444f52 | CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1>>N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 | Cl.C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)NC(C)=O)O.[OH-].[Na+]>>C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N)O | CC(=O)[NH:1][C@@H:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[CH2:10][C@H:11]([OH:12])[C@H:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[N:21]([CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[NH2:1][C@@H:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH... | CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 | N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 | null | null | C(CCC)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(CCCC[C@H](Cc2ccccc2)N(Cc2ccccc2)Cc2ccccc2)cc1 | C-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)[C@H](C[C@H](CC1=CC=CC=C1)N)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": ... | null | null | null | null | To 40 ml of 4N hydrochloric acid, was added 10.86 g of (2S,3S,5S)-2-(N,N-dibenzylamino)-5-acetylamino-1,6-diphenyl-3-hexanol, and the resulting solution was refluxed for 6 hours and cooled to room temperature. To the reaction mixture, was added 30 ml of n-butanol, and the resulting mixture was neutralized with dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(CCC)O | null | null | CC(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1>C(CCC)O>N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-33ca35d87a6942beb4ed170777c2d51f | CC(=O)Cl.NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1>>CC(=O)NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 | C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(C=C(CC1=CC=CC=C1)N)=O.N1=CC=CC=C1.C(C)(=O)Cl>>C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(C=C(CC1=CC=CC=C1)NC(C)=O)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][C:5](=[CH:6][C:7](=[O:8])[C@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[N:17]([CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5](=[CH:6][... | CC(=O)Cl.NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 | CC(=O)NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 | null | null | C1(=CC=CC=C1)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 67a4a916abe1047968b46c9f8f63822c89bf28a1a4f499fb1f5fb567edb4070f | 178c607e9acb60b2ba315fc0f5a1f8155b3bc47827f60f3f62cd4667d5360363 | O=C(C=CCc1ccccc1)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH2;D1;+0:6])=[C:7]-[C:8]=[O;D1;H0:9]>>[C:4]-[C:5](=[C:7]-[C:8]=[O;D1;H0:9])-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 90.6 | [{"value": 89.4, "product": "C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(C=C(CC1=CC=CC=C1)NC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(C=C(CC1=CC=CC=C1)NC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 25 | CELSIUS | 16 | HOUR | (2S)-2-(N,N-dibenzylamino)-5-amino-1,6-diphenyl-4-hexene-3-one (100.0 g, 214.1 mmol) was dissolved in toluene (500 ml), to which pyridine (10 ml, 124.3 mmol) was added under a nitrogen stream. Acetyl chloride (25.7 g, 321.1 mmol) was slowly added to the resultant mixture while chilling with ice water so as not to raise... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide | Enamine.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 25 | 16 | CC(=O)Cl.NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1>C1(=CC=CC=C1)C>CC(=O)NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0cdbbab9e64b4da2a8e03a5d6bc2a79d | CCOC(=O)Cl.NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1>>CCOC(=O)C(=CC(=O)[C@H](C(N)c1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 | O.C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](CC1=CC=CC=C1)C(C=C(CC1=CC=CC=C1)N)=O.N1=CC=CC=C1.ClC(=O)OCC>>C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](C(C1=CC=CC=C1)N)C(C=C(CC1=CC=CC=C1)C(=O)OCC)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[C:6](=[CH:7][C:8](=[O:9])[C@H:10]([CH2:11][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[N:19]([CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)([NH2:12])[CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1>>[CH3:1][CH2:2][O:3][C:4]... | CCOC(=O)Cl.NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 | CCOC(=O)C(=CC(=O)[C@H](C(N)c1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | db6f5c3cfeadf4fff3cfe6cffbb776d4b32881b4238bb6843ad6df8c0f9670bc | 25f92354a650be3ddc791d7169fe2a9226bea5d9cb1418b2ac81fe7c4e3ca864 | O=C(C=CCc1ccccc1)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#7:5]-[C:6](-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:11](=[O;D1;H0:12])-[C:13]=[C;H0;D3;+0:14](-[NH2;D1;+0:15])-[C:16]-[c:17]>>[#7:5]-[C:6](-[C:11](=[O;D1;H0:12])-[C:13]=[C;H0;D3;+0:14](-[C:16]-[c:17])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[CH;D3;+0:7](-[NH2;D1;+0:15])-... | 28.5 | [{"value": 28.5, "product": "C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@@H](C(C1=CC=CC=C1)N)C(C=C(CC1=CC=CC=C1)C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 12 | HOUR | A solution of 5 g of (2S)-2-(N,N-dibenzylamino)-5-amino-1,6-diphenyl-4-hexene-3-one in toluene (100 ml) was chilled with ice water. To the solution, 5 ml of pyridine and 5 ml of ethyl chloroformate were gradually added. The reaction mixture was stirred at 70° C. for 12 hours, and then chilled with ice water. 5 ml of wa... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide.Ether | Ester.Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 70 | 12 | CCOC(=O)Cl.NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1>C1(=CC=CC=C1)C>CCOC(=O)C(=CC(=O)[C@H](C(N)c1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9172f8c663b2415390d899a38b676f70 | CN.O=Cc1ccc(Oc2ccccc2)cc1>>CNCc1ccc(Oc2ccccc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.CN.C(C)(=O)OCC>>CNCC1=CC=C(C=C1)OC1=CC=CC=C1 | [CH3:1][NH2:2].O=[CH:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1 | CN.O=Cc1ccc(Oc2ccccc2)cc1 | CNCc1ccc(Oc2ccccc2)cc1 | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C;D1;H3:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 80 | [{"value": 80.0, "product": "CNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Phenoxybenzaldehyde (10.0 g, 0.05 mol), excess methylamine and 1.5 g of 10% Pd/C in 200 mL of methanol were stirred under an atmosphere of hydrogen for 16 hours. After removal of the catalyst by filtration through Celite®, the filtrate was concentrated under reduced pressure to give the crude product as an oil. Chrom... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].CO | null | null | CN.O=Cc1ccc(Oc2ccccc2)cc1>[Pd].CO>CNCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-794cb843b0f04a4eac209e5d6c1d7157 | CC(C)CN.O=Cc1ccc(Oc2ccccc2)cc1>>CC(C)CNCc1ccc(Oc2ccccc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C(C(C)C)N.[H][H]>>C(C(C)C)NCC1=CC=C(C=C1)OC1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O=[CH:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1 | CC(C)CN.O=Cc1ccc(Oc2ccccc2)cc1 | CC(C)CNCc1ccc(Oc2ccccc2)cc1 | null | [Pd] | CCOCC.C(C)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "C(C(C)C)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Phenoxybenzaldehyde (10.0 g, 0.05 mmol), excess isobutylamine and 1.0 g of 10% Pd/O in 200 mL of ethanol were stirred under an inert atmosphere for 16 hours followed by an atmosphere of hydrogen for 16 hours. After removal of the catalyst by filtration through Celite®, the filtrate was concentrated under reduced pres... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].CCOCC.C(C)O | null | null | CC(C)CN.O=Cc1ccc(Oc2ccccc2)cc1>[Pd].CCOCC.C(C)O>CC(C)CNCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2bdfd002906946eb81b3659d396dc2d6 | CC(=O)[O-].O=Cc1ccc(Oc2ccccc2)cc1.[NH4+]>>c1ccc(Oc2ccc(CNCc3ccc(Oc4ccccc4)cc3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C(C)(=O)[O-].[NH4+]>>O(C1=CC=CC=C1)C1=CC=C(CNCC2=CC=C(C=C2)OC2=CC=CC=C2)C=C1 | O=[C:1]([CH3:14])[O-:17].O=[CH:10][c:9]1[cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][cH:22][cH:21][cH:20][cH:19]2)[cH:27][cH:26]1.[NH4+:11]>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH2:12][c:13]3[cH:14][cH:15][c:16]([O:17][c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][cH:25]3)[cH:26][cH:27]2)[... | CC(=O)[O-].O=Cc1ccc(Oc2ccccc2)cc1.[NH4+] | c1ccc(Oc2ccc(CNCc3ccc(Oc4ccccc4)cc3)cc2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1c1753321a7adbd0a71cb8e5cd05c74769d92c1b141a5a3e9a4e96879adc415b | bed79f2434676d7a8014849d2eda77259897e8fe2565b91f0a1da9d939060402 | c1ccc(Oc2ccc(CNCc3ccc(Oc4ccccc4)cc3)cc2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[O-;H0;D1:3].O=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]-[#8:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c:12]:[c:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:1.[NH4+;D0:16]>>[c:8]-[#8:9]-[c;H0;D3;+0:10]1:[c:17]:[c:18]:[cH;D2;+0:1]:[c:19]:[cH;D2;+0:15]:1.[c:6]:[c:5](-[CH2;D2;+0:4]-[NH;D2;+0:16]-[C:20]-[c:21]1:[... | null | [] | null | null | null | null | 4-Phenoxybenzaldehyde was reacted with ammonium acetate to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Ether.Ether.Secondary amine | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(=O)[O-].O=Cc1ccc(Oc2ccccc2)cc1.[NH4+]>>c1ccc(Oc2ccc(CNCc3ccc(Oc4ccccc4)cc3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9b1496cf769e4354b5369132fdaaf338 | C#CCN.O=Cc1ccc(Oc2ccccc2)cc1>>C#CCNCc1ccc(Oc2ccccc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C(C#C)N.C(#N)[BH3-].[Na+]>>C(C#C)NCC1=CC=C(C=C1)OC1=CC=CC=C1 | [CH:1]#[C:2][CH2:3][NH2:4].O=[CH:5][c:6]1[cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>>[CH:1]#[C:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1 | C#CCN.O=Cc1ccc(Oc2ccccc2)cc1 | C#CCNCc1ccc(Oc2ccccc2)cc1 | null | null | C(C)(=O)O.CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H1:5]#[C:6]-[C:7]-[NH2;D1;+0:8]>>[C;D1;H1:5]#[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 93.6 | [{"value": 93.0, "product": "C(C#C)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "C(C#C)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 4-Phenoxybenzaldehyde (5.0 g, 25.2 mmol) and propargylamine (1.46 g, 26.5 mmol) were dissolved in 100 mL of 1% acetic acid in methanol under an atmosphere of dry nitrogen. Sodium cyanoborohydride (1.66 g, 26.5 mmol) was added, and stirring was continued for 18 hours at which time the solvent was removed under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)O.CO | null | 18 | C#CCN.O=Cc1ccc(Oc2ccccc2)cc1>C(C)(=O)O.CO>C#CCNCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-da791c1d03e640cea0191e88eb7cbea9 | O=Cc1ccc(Oc2ccccc2)cc1>>OCc1ccc(Oc2ccccc2)cc1 | [NH4+].[Cl-].O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.B>>O(C1=CC=CC=C1)C1=CC=C(CO)C=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1 | O=Cc1ccc(Oc2ccccc2)cc1 | OCc1ccc(Oc2ccccc2)cc1 | null | null | C(C)(=O)OCC.C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(Oc2ccccc2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 92 | [{"value": 92.0, "product": "O(C1=CC=CC=C1)C1=CC=C(CO)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 0° C. solution of 4-phenoxybenzaldehyde (5.0 g, 25.2 mmol) in 10 mL THF under an atmosphere of dry N2 was treated with borane (1.0M in THF, 11.25 mL) for 1 hour. A saturated NH4Cl solution was added, and the mixture was diluted with ethyl acetate. The organic layer was washed with 1M HCl, 5% NaHCO3 and brine, dried a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC.C1CCOC1 | null | null | O=Cc1ccc(Oc2ccccc2)cc1>C(C)(=O)OCC.C1CCOC1>OCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6545934050254b01a1132ea181e193e4 | O=C(O)c1ccc(OC2C=CCCC2)cc1>>OCc1ccc(OC2C=CCCC2)cc1 | C1(C=CCCC1)OC1=CC=C(C(=O)O)C=C1.CN1CCOCC1.C(C(C)C)OC(=O)Cl>>C1(C=CCCC1)OC1=CC=C(CO)C=C1 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1 | O=C(O)c1ccc(OC2C=CCCC2)cc1 | OCc1ccc(OC2C=CCCC2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | C1=CC(Oc2ccccc2)CCC1 | O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 18 | [{"value": 18.0, "product": "C1(C=CCCC1)OC1=CC=C(CO)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.0, "product": "C1(C=CCCC1)OC1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 10 | MINUTE | 4-(Cyclohex-2-enyloxy)benzoic acid (25 g, 115 mmol) was dissolved in 250 mL dry tetrahydrofuran and cooled to -10° C. under an atmosphere of dry nitrogen. N-Methylmorpholine (12.6 mL, 115 mmol) and isobutylchloroformate (15.9 mL, 115 mmol) were added. After 10 minutes at -10° C., the mixture was warmed to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.C1=CCCCC1 | Other | O1CCCC1 | -10 | 0.166667 | O=C(O)c1ccc(OC2C=CCCC2)cc1>O1CCCC1>OCc1ccc(OC2C=CCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-12c32416dd51410dbbe39f4fd84d7649 | OCc1ccc(OC2C=CCCC2)cc1>>O=Cc1ccc(OC2C=CCCC2)cc1 | C1(C=CCCC1)OC1=CC=C(CO)C=C1.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>C1(C=CCCC1)OC1=CC=C(C=O)C=C1 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH:9]=[CH:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1 | OCc1ccc(OC2C=CCCC2)cc1 | O=Cc1ccc(OC2C=CCCC2)cc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1=CC(Oc2ccccc2)CCC1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 77.6 | [{"value": 77.0, "product": "C1(C=CCCC1)OC1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "C1(C=CCCC1)OC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | The alcohol resulting from Example 37A (4.24 g, 20.7 mmol) was dissolved in 250 mL of methylene chloride under an atmosphere of dry nitrogen. Pyridinium chlorochromate (5.62 g, 26.1 mmol) was added over 5 minutes. After stirring at ambient temperature 72 hours, the mixture was filtered through Celite® and concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.C1=CCCCC1 | null | C(Cl)Cl | null | 72 | OCc1ccc(OC2C=CCCC2)cc1>C(Cl)Cl>O=Cc1ccc(OC2C=CCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-46ec9658e6fe46a7a019861f41f306d6 | OCCCCCc1ccccc1>>O=CCCCCc1ccccc1 | C1(=CC=CC=C1)CCCCCO.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>C1(=CC=CC=C1)CCCCC=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | OCCCCCc1ccccc1 | O=CCCCCc1ccccc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 57 | [{"value": 57.0, "product": "C1(=CC=CC=C1)CCCCC=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 5-phenylpentanol (15.0 g, 91 mmol) in methylene chloride was added pyridinium chlorochromate (24.6 g, 114 mmol) under an atmosphere of dry nitrogen at room temperature. After 18 hours, the mixture was filtered through a bed of Celite®, and purified by flash chromatography on silica gel eluting with 10%... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | null | 18 | OCCCCCc1ccccc1>C(Cl)Cl>O=CCCCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-39484ed599c04b63b91693a7e1f09678 | CCCN.O=C(Cl)c1ccccc1>>CCCNC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)Cl.C(CC)N>>C(CC)NC(C1=CC=CC=C1)=O | [CH3:1][CH2:2][CH2:3][NH2:4].Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CCCN.O=C(Cl)c1ccccc1 | CCCNC(=O)c1ccccc1 | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | 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:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 96 | [{"value": 96.0, "product": "C(CC)NC(C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzoyl chloride (10 mL, 86.2 mmol) in ethyl acetate (200 mL) was treated with propylamine. The precipitate was removed by filtration, and the solution was washed with 1M HCl, 5% NaHCO3, and brine, dried over MgSO4 and concentrated in vacuo to give the title compound in 96% yield.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(C)(=O)OCC | null | null | CCCN.O=C(Cl)c1ccccc1>C(C)(=O)OCC>CCCNC(=O)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9b5e667c8e17468295849f3310e72ee5 | O=Cc1ccc(F)cc1.Oc1ccc2c(c1)OCO2>>O=Cc1ccc(Oc2ccc3c(c2)OCO3)cc1 | FC1=CC=C(C=O)C=C1.C1OC=2C=C(C=CC2O1)O.[H-].[Na+].Cl>>C1OC=2C=C(OC3=CC=C(C=O)C=C3)C=CC2O1 | F[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:18][cH:17]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[O:14][CH2:15][O:16]2>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[O:14][CH2:15][O:16]3)[cH:17][cH:18]1 | O=Cc1ccc(F)cc1.Oc1ccc2c(c1)OCO2 | O=Cc1ccc(Oc2ccc3c(c2)OCO3)cc1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccc3c(c2)OCO3)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 67.7 | [{"value": 67.0, "product": "C1OC=2C=C(OC3=CC=C(C=O)C=C3)C=CC2O1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.7, "product": "C1OC=2C=C(OC3=CC=C(C=O)C=C3)C=CC2O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 12 | HOUR | A solution of 3,4-methylenedioxyphenol (7.0 g, 50.7 mmol) in anhydrous DMSO (20 mL) was added dropwise over 30 minutes to a stirred suspension of 60% oil dispersion sodium hydride (2.02 g, 50 mmol) in anhydrous DMSO (40 mL) under a nitrogen atmosphere. Upon completion of addition, a solution of p-fluorobenzaldehyde (6.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)OCO2 | HF | O.CS(=O)C | 150 | 12 | O=Cc1ccc(F)cc1.Oc1ccc2c(c1)OCO2>O.CS(=O)C>O=Cc1ccc(Oc2ccc3c(c2)OCO3)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8aab07cc7dad4fb2b3690f8d873e9752 | C=O.COc1cccc(CCN)c1>>COc1ccc2c(c1)CCNC2 | COC=1C=C(CCN)C=CC1.C=O>>COC=1C=C2CCNCC2=CC1 | O=[CH2:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:9][CH2:10][NH2:11])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][NH:11][CH2:12]2 | C=O.COc1cccc(CCN)c1 | COc1ccc2c(c1)CCNC2 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 70d5c5fa4829c190686519bd59ebafece61109628b82676e21fcfe08888b2885 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc2c(c1)CCNC2 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[c:9]:[c:8]:[c;H0;D3;+0:7]1:[c:5](:[c:6])-[C:4]-[C:3]-[NH;D2;+0:2]-[CH2;D2;+0:1]-1 | 52 | [{"value": 52.0, "product": "COC=1C=C2CCNCC2=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A mixture of m-methoxyphenethylamine (25 g, 0.165 mol), 37% formaldehyde (12.7 mL) and water (12.7 mL) was stirred for 20 minutes. The reaction mixture was heated at 95°-100° C. for 1.5 hours, cooled, diluted with ice-water, and extracted with toluene (3x). The combined organic extracts were washed with saturated sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1ccccc1 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | HO- | O | null | 0.333333 | C=O.COc1cccc(CCN)c1>O>COc1ccc2c(c1)CCNC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-16b07fe1a84947d183d74da1474fda1b | Cc1ccccc1O.O=Cc1ccc(F)cc1>>Cc1ccccc1Oc1ccc(C=O)cc1 | CCCCCC.C(C)(=O)OCC.FC1=CC=C(C=O)C=C1.C1(=CC=CC=C1O)C.[H-].[Na+]>>CC1=C(OC2=CC=C(C=O)C=C2)C=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[OH:8].F[c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15][cH:16]1 | Cc1ccccc1O.O=Cc1ccc(F)cc1 | Cc1ccccc1Oc1ccc(C=O)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | null | [] | null | null | 1 | HOUR | A solution of o-cresol (5.4 g, 50.7 mmol) in DMSO (10 mL) was added dropwise to a stirred mixture of 60% oil dispersion sodium hydride (2.02 g, 50.5 mmol) in DMSO (20 mL). After stirring for 1 hour at ambient temperature, a solution of p-fluorobenzaldehyde (5.36 mL, 50 mmol) in DMSO (10 mL) was added dropwise. After th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CS(=O)C | null | 1 | Cc1ccccc1O.O=Cc1ccc(F)cc1>CS(=O)C>Cc1ccccc1Oc1ccc(C=O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7ea1fd831cca4e038981a8eb07c45074 | CCCN.O=Cc1cccc(Oc2ccccc2)c1>>CCCNCc1cccc(Oc2ccccc2)c1 | O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.C(CC)N.[BH4-].[Na+]>>C(CC)NCC1=CC(=CC=C1)OC1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][NH2:4].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1>>[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | CCCN.O=Cc1cccc(Oc2ccccc2)c1 | CCCNCc1cccc(Oc2ccccc2)c1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C(C)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 57.3 | [{"value": 57.0, "product": "C(CC)NCC1=CC(=CC=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "C(CC)NCC1=CC(=CC=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 3-Phenoxybenzaldehyde (2.00 mL, 2.29 g, 11.6 mmol), n-propylamine (0.95 mL, 0.68 g, 11.5 mmol), and p-toluenesulfonic acid monohydrate (15 mg, 0.08 mmol) were dissolved in absolute ethanol (15 mL), then heated to 80° C. in a sealed tube for 2.5 hours. The reaction was cooled to room temperature, transfered to a round-b... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)O | 80 | null | CCCN.O=Cc1cccc(Oc2ccccc2)c1>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)O>CCCNCc1cccc(Oc2ccccc2)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ff389deafe3148fab9bbadbf4d1fa850 | CCCCCC.CCOC(=O)c1ccc(O)cc1.CCOC(C)=O>>CCOC(=O)c1ccc(Oc2ccc(C=O)o2)cc1 | C(C)OC(C1=CC=C(C=C1)O)=O.CCCCCC.CCOC(=O)C>>C(C)OC(=O)C1=CC=C(OC2=CC=C(O2)C=O)C=C1 | CCCCC[CH3:13].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:18][cH:19]1.[CH2:11]([CH3:12])[O:17][C:15]([CH3:14])=[O:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([CH:15]=[O:16])[o:17]2)[cH:18][cH:19]1 | CCCCCC.CCOC(=O)c1ccc(O)cc1.CCOC(C)=O | CCOC(=O)c1ccc(Oc2ccc(C=O)o2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7104fd98c71b74fadb6cf4b9187d3b9292997db6bf5268ec6b7986c5aa1a0938 | 3396f4937f87ec8a556badb56081de99359f3116e3c34f4ecab53a49455e0335 | c1ccc(Oc2ccco2)cc1 | C-C-C-C-C-[CH3;D1;+0:1].[CH3;D1;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:5](-[CH3;D1;+0:6])=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[CH;D2;+0:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[o;H0;D2;+0:4]:1 | null | [] | null | null | null | null | Using ethyl-4-hydroxybenzoate, the title compound was prepared by the method of Example 52A, except chromatography using 3:1 hexane-EtOAc was used for purification. 1H NMR (CDCl3) δ 9.45 (s, 1H), 8.10 (m, 2H), 7.25 (d, 1H), 7.19 (m, 2H), 5.75 (d, 1H), 4.40 (q, 2H), 1.41 (t, 3H). MS (DCl/NH3) m/e 261 (M+H)+, 278 (M+H+NH... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol | Aldehyde.Ether | null | c1ccoc1 | c1ccccc1.c1ccoc1 | Other | null | null | null | CCCCCC.CCOC(=O)c1ccc(O)cc1.CCOC(C)=O>>CCOC(=O)c1ccc(Oc2ccc(C=O)o2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a164abf20dbc49c9b6d478b635237038 | N#Cc1ccc(CBr)cc1.c1cc[nH]c1>>N#Cc1ccc(Cn2cccc2)cc1 | N1C=CC=C1.BrCC1=CC=C(C#N)C=C1>>C(#N)C1=CC=C(CN2C=CC=C2)C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:14][cH:13]1.[nH:8]1[cH:9][cH:10][cH:11][cH:12]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1 | N#Cc1ccc(CBr)cc1.c1cc[nH]c1 | N#Cc1ccc(Cn2cccc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ed81cee7c9cb1b5c2931f1dacbfdcf63d83b311ec7685759e6b229eee13149ed | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2cccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]1:[c:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[c:9]:1):[c:4] | null | [] | null | null | null | null | Using pyrrole and 4-(bromomethyl)benzonitrile and the method of Example 53A, except using DMF as the solvent, provided N-(4-cyanobenzyl)pyrrole. 1H NMR (CDCl3) δ 7.62 (m, 2H), 7.14 (m, 2H), 6.69 (m, 2H), 6.24 (m, 2H), 5.15 (s, 2H). MS (DCl/NH3) m/e 183 (M+H)+, 200 (M+H+NH3)+.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | HBr | CN(C)C=O | null | null | N#Cc1ccc(CBr)cc1.c1cc[nH]c1>CN(C)C=O>N#Cc1ccc(Cn2cccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3544623d1de2487d8d6e88d0e1269194 | Cc1cc([N+](=O)[O-])ccc1F.Oc1ccccc1>>Cc1cc([N+](=O)[O-])ccc1Oc1ccccc1 | C1(=CC=CC=C1)O.FC1=C(C=C(C=C1)[N+](=O)[O-])C>>CC=1C=C(C=CC1OC1=CC=CC=C1)[N+](=O)[O-] | F[c:10]1[c:2]([CH3:1])[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9]1.[OH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Cc1cc([N+](=O)[O-])ccc1F.Oc1ccccc1 | Cc1cc([N+](=O)[O-])ccc1Oc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | null | [] | 60 | CELSIUS | null | null | Using phenol and 2-fluoro-5-nitrotoluene and the procedures described in Example 52A, except the reaction was heated to 60° C. overnight and vacuum distilled at 4.5 mm Hg, 174°-5° C., provided 3-methyl-4-phenoxynitrobenzene. 1H NMR (CDCl3) δ 8.16 (dd, 1H), 8.00 (dd, 1H), 7.42 (m, 2H), 7.23 (m, 1H), 7.05 (m, 2H), 6.78 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | null | 60 | null | Cc1cc([N+](=O)[O-])ccc1F.Oc1ccccc1>>Cc1cc([N+](=O)[O-])ccc1Oc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bf5fec9254e74095aecd364f22ab9d66 | Cc1cc([N+](=O)[O-])ccc1Oc1ccccc1>>Cc1cc(N)ccc1Oc1ccccc1 | CC=1C=C(C=CC1OC1=CC=CC=C1)[N+](=O)[O-]>>CC=1C=C(N)C=CC1OC1=CC=CC=C1 | O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:7][cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:6][cH:7][c:8]1[O:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | Cc1cc([N+](=O)[O-])ccc1Oc1ccccc1 | Cc1cc(N)ccc1Oc1ccccc1 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The nitro compound prepared above was reduced under H2 using 10% Pd/C catalyst in MeOH to give 3-methyl-4-phenoxyaniline. 1H NMR (CDCl3) δ 7.27 (m, 2H), 6.97 (m, 1H), 6.83 (m, 2H), 6.80 (d, 1H), 6.60 (d, 1H), 6.52 (m, 1H), 3.53 (br s, 2H), 2.11 (s, 3H). MS (DCl/NH3) m/e 200 (M+H)+, 217 (M+H+NH3)+.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | Cc1cc([N+](=O)[O-])ccc1Oc1ccccc1>CO>Cc1cc(N)ccc1Oc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-78415148fab842c09273602b43e2f3b1 | Cc1ccccc1.Cc1ccccc1>>Cc1cc(C#N)ccc1Oc1ccccc1 | C(=O)([O-])[O-].[Na+].[Na+].C1(=CC=CC=C1)C.[Cu]C#N.C1(=CC=CC=C1)C.[C-]#N.[Na+].Cl>>CC=1C=C(C#N)C=CC1OC1=CC=CC=C1 | C[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[CH3:1][c:2]1[cH:3][cH:4][cH:7][cH:8][cH:9]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]1[O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | Cc1ccccc1.Cc1ccccc1 | Cc1cc(C#N)ccc1Oc1ccccc1 | null | null | O.CCOC(=O)C | Functional Group Addition | OtherReaction | 730ee5532fe1f1ce5c58196fdc3360f032e552c00ead134d454a825569253024 | 4a1296dad504a96af019461213ce7f58054a77f45cd7ebae5dca5fc0a14c6fc6 | c1ccc(Oc2ccccc2)cc1 | C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c;H0;D3;+0:9](-[C:13]#[N;D1;H0:14]):[c:10]:[c:11]:[c;H0;D3;+0:12]:1-[#8:15]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 17 | [{"value": 17.0, "product": "CC=1C=C(C#N)C=CC1OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 15 | MINUTE | The amine prepared above (2.75 g, 13.8 mmol) was added to 2N HCl (20 mL), then cooled to 5° C., giving a thick purple slurry. A solution of sodium nitrite (0.84 g, 14.2 mmol) in water (2 mL) was added dropwise, keeping the reaction temperature -5° C. Addition of another small portion of sodium nitrite to the reaction r... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether.Nitrile | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | O.CCOC(=O)C | 5 | 0.25 | Cc1ccccc1.Cc1ccccc1>O.CCOC(=O)C>Cc1cc(C#N)ccc1Oc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6e2150c708be4e9c8308fb78a619353c | BrCc1ccccc1>>NCC#CCc1ccccc1 | Cl.C(CCC)[Li].CN1C(N(CCC1)C)=O.C(C1=CC=CC=C1)Br>>C1=CC=C(C=C1)CC#CCN | Br[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][CH2:2][C:3]#[C:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | BrCc1ccccc1 | NCC#CCc1ccccc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 2569c956eb207516196f38f21640355fb8efa7b14d1f525c5e46b02591a81f3e | 8205b8f338a7a2aacc6723bbce15376aca47212df9472230d75ceaa516c0eb32 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C:5]#[C:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 59 | [{"value": 59.0, "product": "C1=CC=C(C=C1)CC#CCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.6, "product": "C1=CC=C(C=C1)CC#CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | The compound resulting from Example 60A (4.35 g of -75% pure material, -16.5 mmol) was dissolved in THF (87 mL), cooled to 0° C., then n-butyllithium (16.5 mL of 1.6M hexanes solution) was added dropwise, followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1 H)-pyrimidinone (3.20 mL, 3.39 g, 26.5 mmol) and benzyl bromide (3.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary amine.Alkyne | null | null | c1ccccc1 | Br- | C1CCOC1 | 0 | 3 | BrCc1ccccc1>C1CCOC1>NCC#CCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d70c7cbd86ba4263a4a1b2bc04c28803 | CCC(=O)Cl.Nc1ccc(Nc2ccccc2)cc1>>CCC(=O)Nc1ccc(Nc2ccccc2)cc1 | C(CC)(=O)Cl.C1(=CC=CC=C1)NC1=CC=C(C=C1)N.C(=O)(O)[O-].[Na+]>>C1(=CC=CC=C1)NC1=CC=C(C=C1)NC(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1 | CCC(=O)Cl.Nc1ccc(Nc2ccccc2)cc1 | CCC(=O)Nc1ccc(Nc2ccccc2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Nc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 75 | [{"value": 75.0, "product": "C1(=CC=CC=C1)NC1=CC=C(C=C1)NC(CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "C1(=CC=CC=C1)NC1=CC=C(C=C1)NC(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A stirred mixture of 1.84 g (10.0 mmol, 1 eq.) of commercial N-phenyl-1,4-phenylenediamine (a black solid) and 1.18 g (14.0 mmol, 1.4 eq.) of NaHCO3 in 40 mL of CH2Cl2 was cooled to 0° C. To this suspension was added a solution of 0.96 mL (11.0 mmol, 1.1 eq.) of propionyl chloride in 10 mL of CH2Cl2 dropwise. The ice b... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 1 | CCC(=O)Cl.Nc1ccc(Nc2ccccc2)cc1>C(Cl)Cl>CCC(=O)Nc1ccc(Nc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d9b649ba151849c18f73f4aaffbe6ca0 | CCCN.O=C(O)c1ccc(Nc2ccccc2)cc1>>CCCNC(=O)c1ccc(Nc2ccccc2)cc1 | C(C)(=O)OCC.C1(=CC=CC=C1)NC1=CC=C(C(=O)O)C=C1.C(CC)N.CCN=C=NCCCN(C)C.Cl>>C(CC)NC(C1=CC=C(C=C1)NC1=CC=CC=C1)=O | [CH3:1][CH2:2][CH2:3][NH2:4].O[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1 | CCCN.O=C(O)c1ccc(Nc2ccccc2)cc1 | CCCNC(=O)c1ccc(Nc2ccccc2)cc1 | null | CN(C)C=1C=CN=CC1 | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 40.1 | [{"value": 40.0, "product": "C(CC)NC(C1=CC=C(C=C1)NC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.1, "product": "C(CC)NC(C1=CC=C(C=C1)NC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 1.06 g (5.0 mmol, 1 eq.) of 4-phenylaminobenzoic acid, prepared by the method of Portnaya, et al., Zhur. Obshchei. Khim., 30: 2693 (1960), n-propylamine (0.82 mL, 10.0 mmol, 2 eq.) and 0.061 g (0.5 mmol, 0.1 eq.) of DMAP in THF at 0° C. was added 1.05 g (5.5 mmol, 1.1 eq.) of EDCl. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C1CCOC1 | null | 8 | CCCN.O=C(O)c1ccc(Nc2ccccc2)cc1>CN(C)C=1C=CN=CC1.C1CCOC1>CCCNC(=O)c1ccc(Nc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f184d13018f8412282d80e43650a7fd1 | COC(=O)c1ccc(CBr)cc1.Oc1ccccc1>>COC(=O)c1ccc(COc2ccccc2)cc1 | O.COC(C1=CC=C(C=C1)CBr)=O.C(=O)([O-])[O-].[K+].[K+].C1(=CC=CC=C1)O>>COC(C1=CC=C(C=C1)COC1=CC=CC=C1)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][cH:17]1.[OH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1 | COC(=O)c1ccc(CBr)cc1.Oc1ccccc1 | COC(=O)c1ccc(COc2ccccc2)cc1 | null | null | CN(C)C=O | 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:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 88 | [{"value": 88.0, "product": "COC(C1=CC=C(C=C1)COC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "COC(C1=CC=C(C=C1)COC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred mixture of 5.72 g (25.0 mmol, 1.0 eq.) of methyl-4-bromomethylbenzoate and 3.80 g (27.5 mmol, 1.1 eq.) of K2CO3 in 10 mL of DMF at ambient temperature was added a solution of 2.59 g (27.5 mmol, 1.1 eq.) of phenol in 10 mL of DMF dropwise, and the mixture stirred overnight. The reaction mixture was poured i... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 8 | COC(=O)c1ccc(CBr)cc1.Oc1ccccc1>CN(C)C=O>COC(=O)c1ccc(COc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bdaa0213a3154c3a8a7f150b0134379b | O=Cc1ccc(Oc2ccccc2)cc1>>C=Cc1ccc(Oc2ccccc2)cc1 | [Br-].CC(C)([O-])C.[K+].O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1>>O(C1=CC=CC=C1)C1=CC=C(C=C)C=C1 | O=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1 | O=Cc1ccc(Oc2ccccc2)cc1 | C=Cc1ccc(Oc2ccccc2)cc1 | null | null | CCCCCC.C1CCOC1 | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | To a suspension of methyltriphenylphosphium bromide (7.85 g, 22 mmol) in THF (10 mL) was added potassium tert-butoxide (1.0M solution in THF, 22 mL). After 30 minutes, 4-phenoxybenzaldehyde (3.96 g, 20 mmol) was added to the above mixture. The reaction was diluted with equal volume of hexane after 20 minutes and filter... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | c1ccccc1.c1ccccc1 | null | CCCCCC.C1CCOC1 | null | 0.5 | O=Cc1ccc(Oc2ccccc2)cc1>CCCCCC.C1CCOC1>C=Cc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-77770289c7dd46c3b7cbc1fbd1ef978e | CCC(=O)Cl.NCCc1ccc(Oc2ccccc2)cc1>>CCC(=O)NCCc1ccc(Oc2ccccc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=C1)CCN.C(CC)(=O)Cl>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CCNC(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | CCC(=O)Cl.NCCc1ccc(Oc2ccccc2)cc1 | CCC(=O)NCCc1ccc(Oc2ccccc2)cc1 | null | null | N1=CC=CC=C1.C(Cl)Cl.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Oc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4] | null | [] | null | null | 6 | HOUR | To the solution of crude amine resulting from Example 67E in methylene chloride (20 mL) and pyridine (5 mL) was added propionyl chloride (3.0 mL, 34 mmol). After 6 hours, the reaction was diluted with ethyl acetate (80 mL), washed with water (20 mL), 10% aqueous hydrochloric acid (20 mL), water (20 mL), saturated coppe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1.C(Cl)Cl.C(C)(=O)OCC | null | 6 | CCC(=O)Cl.NCCc1ccc(Oc2ccccc2)cc1>N1=CC=CC=C1.C(Cl)Cl.C(C)(=O)OCC>CCC(=O)NCCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1e8863cc88274d67b74a0a19be798263 | COCCN.O=Cc1ccc(Oc2ccccc2)cc1>>COCc1cc(Oc2ccccc2)ccc1CN | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.COCCN.C(C)(=O)O.C(#N)[BH3-].[Na+]>>COCC1=C(CN)C=CC(=C1)OC1=CC=CC=C1 | C([CH2:3][O:2][CH3:1])[NH2:18].O=[CH:17][c:16]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[CH2:17][NH2:18] | COCCN.O=Cc1ccc(Oc2ccccc2)cc1 | COCc1cc(Oc2ccccc2)ccc1CN | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 4991e4e1f72094ced95531db86136435cf52ba0194d645a9cc05901e56271586 | 9982f654bbc9e9dae5c9ac37ebf5db5c314e84c710d51804e496254773ca8125 | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[C;D1;H3:7]-[#8:8]-[CH2;D2;+0:9]-C-[NH2;D1;+0:10]>>[C;D1;H3:7]-[#8:8]-[CH2;D2;+0:9]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[CH2;D2;+0:1]-[NH2;D1;+0:10]):[c:3] | null | [] | null | null | 1 | HOUR | A mixture of 4-phenoxybenzaldehyde (1.98 g, 10 mmol) and 2-methoxyethylamine (0.751 g, 10 mmol) in ethanol (10 mL) was stirred for 1 hour. Acetic acid (1 mL) and sodium cyanoborohydride (1M in THF, 10 mL) were added, and the reaction was stirred for 14 hours. The reaction was then partitioned between ether and 10% aque... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine | Ether.Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C(C)O | null | 1 | COCCN.O=Cc1ccc(Oc2ccccc2)cc1>C(C)O>COCc1cc(Oc2ccccc2)ccc1CN |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9f45dad8c60d489d95c63e01bee5ba95 | CSCCN.O=Cc1ccc(Oc2ccccc2)cc1>>CSCCNCc1ccc(Oc2ccccc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.CSCCN>>CSCCNCC1=CC=C(C=C1)OC1=CC=CC=C1 | [CH3:1][S:2][CH2:3][CH2:4][NH2:5].O=[CH:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1>>[CH3:1][S:2][CH2:3][CH2:4][NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1 | CSCCN.O=Cc1ccc(Oc2ccccc2)cc1 | CSCCNCc1ccc(Oc2ccccc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "CSCCNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.5, "product": "CSCCNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Example 68A, 4-phenoxybenzaldehyde (1.98 g, 10 mmol) and 2-methylthioethylamine (0.912 g, 10 mmol) were combined to give the title compound (2.53 g, 93%) 1H NMR (300 MHz, CDCl3) δ 7.32 (m, 4 H), 7.09. (t, 1 H), 6.97 (m, 4 H), 3.80 (s, 2 H), 2.84 9t, 2 H), 2.68 (t, 2 H), 2.10 (s, 3 H... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | CSCCN.O=Cc1ccc(Oc2ccccc2)cc1>>CSCCNCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2584b6a8aff64f61a562814a6a8d559d | CCSCCN.O=Cc1ccc(Oc2ccccc2)cc1>>CCSCCNCc1ccc(Oc2ccccc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.Cl.C(C)SCCN>>C(C)SCCNCC1=CC=C(C=C1)OC1=CC=CC=C1 | [CH3:1][CH2:2][S:3][CH2:4][CH2:5][NH2:6].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[CH3:1][CH2:2][S:3][CH2:4][CH2:5][NH:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | CCSCCN.O=Cc1ccc(Oc2ccccc2)cc1 | CCSCCNCc1ccc(Oc2ccccc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 95 | [{"value": 95.0, "product": "C(C)SCCNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.6, "product": "C(C)SCCNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Example 68A, 4-phenoxybenzaldehyde (1.98 g, 10 mmol) and 2-(ethylthio)ethylamine hydrogen chloride (1.42 g, 10 mmol) were combined to give the title compound (2.72 g, 95%). 1H NMR (300 MHz, CDCl3), δ 7.33 (m, 4 H), 7.09 (t, 1 H), 6.98 (m, 4 H), 3.78 (s, 2 H), 2.84 (t, 2 H), 2.71 (t,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | CCSCCN.O=Cc1ccc(Oc2ccccc2)cc1>>CCSCCNCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bd793c39aa344d96bb53fd572d791e4d | ClCc1ccccc1.NCCS>>NCCSCc1ccccc1 | Cl.NCCS.C(C1=CC=CC=C1)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C1=CC=CC=C1)SCCN | Cl[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH2:2][CH2:3][SH:4]>>[NH2:1][CH2:2][CH2:3][S:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | ClCc1ccccc1.NCCS | NCCSCc1ccccc1 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | A suspension of 2-aminoethanethiol hydrochloride (2.27 g, 20.0 mmol), benzyl chloride (2.42 mL, 21.0 mmol) and cesium carbonate (19.5 g, 60 mmol) in DMF (100 mL) was stirred overnight. The reaction mixture was then diluted with ethyl acetate (200 mL) and filtered into a separation funnel. The solid residue was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1 | HCl | CN(C)C=O.C(C)(=O)OCC | null | 8 | ClCc1ccccc1.NCCS>CN(C)C=O.C(C)(=O)OCC>NCCSCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-101e2eade719414ba492ff8051d17790 | COc1cccc(CCN)c1.O=Cc1ccc(OCc2ccccc2)cc1>>COc1cccc(CCNCc2ccc(Oc3ccccc3)cc2)c1 | [BH4-].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=O)C=C1.COC=1C=C(CCN)C=CC1.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O(C1=CC=CC=C1)C1=CC=C(CNCCC2=CC(=CC=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH2:9][NH2:10])[cH:25]1.O=[CH:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]2c[cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH2:9][NH:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][c:17]3[cH:18][cH:19][cH:20][cH:21]... | COc1cccc(CCN)c1.O=Cc1ccc(OCc2ccccc2)cc1 | COc1cccc(CCNCc2ccc(Oc3ccccc3)cc2)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 189c28e0326d824612a8e258278496428776190cedef9869983dcd51a751d8f8 | b12310d36a7ae840c25126c459f67e71dde00afb1ee9822eebc7ad8fbac3d557 | c1ccc(CCNCc2ccc(Oc3ccccc3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]-[#8:6]-[CH2;D2;+0:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c:10]:[c:11]:[cH;D2;+0:12]:c:1.[C:13]-[C:14]-[NH2;D1;+0:15]>>[C:13]-[C:14]-[NH;D2;+0:15]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]-[#8:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[cH;D2;+0:12]:[c:11]:[c:10]:[cH;D2;+0:9]:1 | 76.2 | [{"value": 76.0, "product": "O(C1=CC=CC=C1)C1=CC=C(CNCCC2=CC(=CC=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.2, "product": "O(C1=CC=CC=C1)C1=CC=C(CNCCC2=CC(=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-benzoxybenzaldehyde (2.5 g, 12.6 mmol), 3-methoxyphenethylamine (1.9 g, 12.6 mmol), a catalytic amount of p-toluenesulfonic acid monohydrate in absolute ethanol (12 mL) was stirred at 80° C. for 1.5 hours. After cooling to room temperature, NaBH4 (0.49 g, 13.0 mmol) was added in portions. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine | Ether.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)O | null | 1 | COc1cccc(CCN)c1.O=Cc1ccc(OCc2ccccc2)cc1>C(C)O>COc1cccc(CCNCc2ccc(Oc3ccccc3)cc2)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-738e7cb49cf74664a77d5d70d96138ca | O=Cc1ccc(Oc2ccccc2)cc1>>OCc1ccc(Oc2ccccc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>O(C1=CC=CC=C1)C1=CC=C(CO)C=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1 | O=Cc1ccc(Oc2ccccc2)cc1 | OCc1ccc(Oc2ccccc2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(Oc2ccccc2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 98.9 | [{"value": 98.9, "product": "O(C1=CC=CC=C1)C1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of 4-phenoxybenzaldehyde (10.0 g, 50 mmol) and 10 mL dry THF was added dropwise to a 0° C. suspension of lithium aluminum hydride (2.1 g, 55.3 mmol) and 100 mL dry THF. The reaction mixture was stirred for 1 hour at 0° C., then was quenched successively with 2.1 mL H20, 2.1 mL 10% NaOH, and 6.3 mL H2O. The r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | null | C1CCOC1 | 0 | 1 | O=Cc1ccc(Oc2ccccc2)cc1>C1CCOC1>OCc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c41fabd17d2d4faaae41576009c8479f | CC(C)[C@H]1COC(=O)N1C(=O)[C@H](C)CCCc1ccccc1.O>>C[C@H](CCCc1ccccc1)C(=O)O | S(=O)([O-])[O-].[Na+].[Na+].C1(=CC=CC=C1)CCC[C@H](C(=O)N1C(OC[C@@H]1C(C)C)=O)C.O[Li].O>>C1(=CC=CC=C1)CCC[C@H](C(=O)O)C | CC(C)[C@H]1COC(=O)N1[C:12]([C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[O:13].[OH2:14]>>[CH3:1][C@H:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C:12](=[O:13])[OH:14] | CC(C)[C@H]1COC(=O)N1C(=O)[C@H](C)CCCc1ccccc1.O | C[C@H](CCCc1ccccc1)C(=O)O | null | null | O.C1CCOC1 | Acylation | OtherReaction | 82c452b9ba01785a7ca901365b7309634888b0ab41fdc45f59a8d97d4e4842e2 | d7ed181e654e8ac131125bbdc5aee5dc90548ccf7549838daacff3be49378f55 | c1ccccc1 | C-C(-C)-[C@@H]1-C-O-C(=O)-N-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C;D1;H3:5].[OH2;D0;+0:6]>>[C:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:6] | 68.9 | [{"value": 68.9, "product": "C1(=CC=CC=C1)CCC[C@H](C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | (4S)-3-((2R)-5-Phenyl-2-methyl-1 -oxopentyl)-4-isopropyl-1,3-oxazolidin -2-one (0.25 g, 0.83 mmol), prepared by the method described in J. Org. Chem. 59: 2261, (1994), was dissolved in 4.2 mL of 4:1 THF:H2O, cooled to 0° C. and purged with N2. 30% Hydrogen peroxide (0.34 mL) was added dropwise, followed by a dropwise a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide | Carboxylic acid | C1COCN1 | null | c1ccccc1 | HO- | O.C1CCOC1 | 0 | 1 | CC(C)[C@H]1COC(=O)N1C(=O)[C@H](C)CCCc1ccccc1.O>O.C1CCOC1>C[C@H](CCCc1ccccc1)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4b0ce23bdeb74629ad420da9020a3807 | CCCN.CCN(CC)CC.CCN=C=NCCCN(C)C.On1nnc2ccccc21>>CCCNC(=O)[C@H](C)CCCc1ccccc1 | CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.C=1C=CC2=C(C1)N=NN2O.O.C(CC)N>>C1(=CC=CC=C1)CCC[C@H](C(=O)NCCC)C | [CH3:1][CH2:2][CH2:3][NH2:4].CCN(CC)[CH2:9][CH3:10].CN(C)CC[CH2:11]N=[C:5]=N[CH2:7][CH3:8].n1n[c:13]2[c:12](n1[OH:6])[cH:17][cH:16][cH:15][cH:14]2>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[C@H:7]([CH3:8])[CH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CCCN.CCN(CC)CC.CCN=C=NCCCN(C)C.On1nnc2ccccc21 | CCCNC(=O)[C@H](C)CCCc1ccccc1 | null | null | C1CCOC1 | Acylation | OtherReaction | e4b17fe5e22be45fa0ec9d3fb4c88e4f86f6d3f2b0969f5c9eb47cc82e3aff35 | 2c6d744ece3ec8bfb720c63fcceb1ab9cf70f9a699e4ed9396119e07c32d7313 | c1ccccc1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-N(-C)-C-C-[CH2;D2;+0:3]-N=[C;H0;D2;+0:4]=N-[CH2;D2;+0:5]-[C;D1;H3:6].[C:7]-[C:8]-[NH2;D1;+0:9].[OH;D1;+0:10]-n1:n:n:[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16]:2:1>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:4](=[O;H0;D1;+0:10])-[C@H;D3;+0:5](-[C;D1;H3:6])-[CH2;D2;+0... | null | [] | null | null | 24 | HOUR | A solution of the compound resulting from Example 82A (0.12 g, 0.63 mmol), n-propylamine (0.052 mL, 0.63 mmol), EDCl (0.14 g, 0.73 mmol), HOBT (0.02 g, 1.4 mmol), Et3N (0.10 mL, 0.73 mmol), and 3.5 mL anydrous THF was stirred at room temperature for 24 hours. Water was added, and the mixture was extracted with EtOAc (3... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine.Tertiary amine | Secondary amide | c1ccc2[nH]nnc2c1 | c1ccccc1 | c1ccccc1 | Other | C1CCOC1 | null | 24 | CCCN.CCN(CC)CC.CCN=C=NCCCN(C)C.On1nnc2ccccc21>C1CCOC1>CCCNC(=O)[C@H](C)CCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-feaac4267df546c792d0547b62a1969a | c1ccc(-c2cccnc2)cc1>>c1ccc(C2CCCNC2)cc1 | C1(=CC=CC=C1)C=1C=NC=CC1.Cl>>C1(=CC=CC=C1)C1CNCCC1 | [cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][n:9][cH:10]2)[cH:11][cH:12]1>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8][NH:9][CH2:10]2)[cH:11][cH:12]1 | c1ccc(-c2cccnc2)cc1 | c1ccc(C2CCCNC2)cc1 | null | O=[Pt]=O | O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc(C2CCCNC2)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1):[c:10]:[c:11]>>[c:1]:[c:2]:[c;H0;D3;+0:3](-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[NH;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-1):[c:10]:[c:11] | 90.3 | [{"value": 90.3, "product": "C1(=CC=CC=C1)C1CNCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 24 | HOUR | A mixture of 3-phenylpyridine (8.0 g, 51.5 mmol), PtO2 (0.8 g), 234 mL of H2O, and 16 mL of concentrated HCl was hydrogenated in a Parr shaker at room temperature for 24 hours. The mixture was filtered, and the filtrate was cooled to 0° C. and was basified with 10N NaOH solution. The mixture was extracted (4×) with CH2... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | null | O=[Pt]=O.O | 0 | 24 | c1ccc(-c2cccnc2)cc1>O=[Pt]=O.O>c1ccc(C2CCCNC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a9cb6e4061fd47429f9ca4cb6f7de7c1 | CC(C)(C)OC(=O)OC(=O)[O-].O=C1CCNCC1>>CC(C)(C)OC(=O)N1CCC(=O)CC1 | Cl.O.N1CCC(CC1)=O.C([O-])(O)=O.[Na+].C(=O)(OC(C)(C)C)OC(=O)[O-]>>C(C)(C)(C)OC(=O)N1CCC(CC1)=O | O=C([O-])O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH2:14]1 | CC(C)(C)OC(=O)OC(=O)[O-].O=C1CCNCC1 | CC(C)(C)OC(=O)N1CCC(=O)CC1 | null | null | C(C)(=O)OCC | Protection | Boc amine protection of secondary amine | 89b6f5da18cce2ceeb2275e0cf856176bfb61327da3eb64755fd7748291720d1 | 94226cf5c3bba13e4d3d11ce3d1edf3253d2a0a588e2936ded4f0148bd13453e | O=C1CCNCC1 | O=C(-[O-])-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[O;D1;H0:8]=[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[C:9](=[O;D1;H0:8])-[C:10]-[C:11]-1 | 86 | [{"value": 86.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.2, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Piperidone monohydrate hydrochloride (5 g, 0.033 mol) was added to 50 mL distilled water and stirred until dissolved. To this solution was added solid sodium bicarbonate (3 g, 0.035 mol) followed by tert-butyl dicarbonate (7.2 g, 0.033 mol), and the resulting clear solution was stirred for 20 hours at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Acid.Carbonic Ester.Secondary amine | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HO- | C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)OC(=O)[O-].O=C1CCNCC1>C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCC(=O)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f2de4ea21ddf47a4ae1d1a025ccb0681 | NCC1CC1.O=Cc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(CNCC3CC3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C1(CC1)CN.C(#N)[BH3-].[Na+]>>C1(CC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1 | [NH2:11][CH2:12][CH:13]1[CH2:14][CH2:15]1.O=[CH:10][c:9]1[cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][cH:2][cH:1][cH:19][cH:18]2)[cH:17][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH2:12][CH:13]3[CH2:14][CH2:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1 | NCC1CC1.O=Cc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(CNCC3CC3)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccc(CNCC3CC3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 78.4 | [{"value": 78.0, "product": "C1(CC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "C1(CC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-Phenoxybenzaldehyde (3.0 g, 15.1 mmol) and cyclopropylmethylamine (1.1 g, 15.1 mmol) were dissolved in methanol (85 mL) under a nitrogen at room temperature. Sodium cyanoborohydride (0.95 g, 15.1 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in eth... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CC1 | Other | CO | null | 48 | NCC1CC1.O=Cc1ccc(Oc2ccccc2)cc1>CO>c1ccc(Oc2ccc(CNCC3CC3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ec70a866ca114f8db510886501039075 | NCc1ccc(F)cc1.O=Cc1ccc(Oc2ccccc2)cc1>>Fc1ccc(CNCc2ccc(Oc3ccccc3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.FC1=CC=C(CN)C=C1.C(#N)[BH3-].[Na+]>>FC1=CC=C(CNCC2=CC=C(C=C2)OC2=CC=CC=C2)C=C1 | [F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH2:7])[cH:22][cH:23]1.O=[CH:8][c:9]1[cH:10][cH:11][c:12]([O:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[cH:22][cH:23]1 | NCc1ccc(F)cc1.O=Cc1ccc(Oc2ccccc2)cc1 | Fc1ccc(CNCc2ccc(Oc3ccccc3)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCc2ccc(Oc3ccccc3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C:6]-[c:7]):[c:4] | 97.6 | [{"value": 97.0, "product": "FC1=CC=C(CNCC2=CC=C(C=C2)OC2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "FC1=CC=C(CNCC2=CC=C(C=C2)OC2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-Phenoxybenzaldehyde (1.0 g, 5.0 mmol) and 4-fluorobenzylamine (631 mg, 5.0 mmol) were dissolved in methanol (17 mL) under a nitrogen at room temperature. Sodium cyanoborohydride (317 mg, 5.0 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in ether, w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | CO | null | 48 | NCc1ccc(F)cc1.O=Cc1ccc(Oc2ccccc2)cc1>CO>Fc1ccc(CNCc2ccc(Oc3ccccc3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b2b29368f8524ef8a54a46dbbda5d4cb | CC(=O)Cl.c1ccc2c(c1)oc1ccccc12>>CC(=O)c1ccc2oc3ccccc3c2c1 | [Cl-].[Al+3].[Cl-].[Cl-].C1=CC=CC=2OC3=C(C21)C=CC=C3.C(C)(=O)Cl>>C(C)(=O)C1=CC2=C(OC3=C2C=CC=C3)C=C1 | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]2[o:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[cH:16]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[o:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[cH:16]1 | CC(=O)Cl.c1ccc2c(c1)oc1ccccc12 | CC(=O)c1ccc2oc3ccccc3c2c1 | null | null | ClC(C)Cl | C-C Coupling | Friedel-Crafts acylation | c40366efee1488dbb44fc1c893f264444d0d6eba9933be54bddf291a724d8b26 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2c(c1)oc1ccccc12 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8;a:4]:[c:5]1:[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:1>>[#8;a:4]:[c:5]1:[c:6]:[c:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9]:[c:10]:1 | 28.3 | [{"value": 28.0, "product": "C(C)(=O)C1=CC2=C(OC3=C2C=CC=C3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.3, "product": "C(C)(=O)C1=CC2=C(OC3=C2C=CC=C3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Aluminum chloride (23.8 g, 178.4 mmol) was added portionwise to a solution of dibenzofuran (30.0 g, 178.4 mmol) and acetyl chloride (14.0 g, 178.4 mmol) in dichloroethane at 0° C. After 8 hours, the reaction was quenched with 6N HCl. The layers were separated and the methylene chloride layer was dried (MgSO4), filtered... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)oc1ccccc12 | c1ccc2c(c1)oc1ccccc12 | c1ccc2c(c1)oc1ccccc12 | HCl | ClC(C)Cl | null | 8 | CC(=O)Cl.c1ccc2c(c1)oc1ccccc12>ClC(C)Cl>CC(=O)c1ccc2oc3ccccc3c2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-16dc2ea20903429ca8b50e928cc61352 | C[C@@H](N)c1cccc2ccccc12.O=Cc1ccc(Oc2ccccc2)cc1>>C[C@@H](NCc1ccc(Oc2ccccc2)cc1)c1cccc2ccccc12 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C1(=CC=CC2=CC=CC=C12)[C@@H](C)N.C(#N)[BH3-].[Na+]>>C1(=CC=CC2=CC=CC=C12)[C@@H](C)NCC1=CC=C(C=C1)OC1=CC=CC=C1 | [CH3:1][C@@H:2]([NH2:3])[c:18]1[cH:19][cH:20][cH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12.O=[CH:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[CH3:1][C@@H:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1)[c:18]1[... | C[C@@H](N)c1cccc2ccccc12.O=Cc1ccc(Oc2ccccc2)cc1 | C[C@@H](NCc1ccc(Oc2ccccc2)cc1)c1cccc2ccccc12 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccc(CNCc3cccc4ccccc34)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](-[NH2;D1;+0:7])-[c:8]>>[C;D1;H3:5]-[C:6](-[c:8])-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 77 | [{"value": 77.0, "product": "C1(=CC=CC2=CC=CC=C12)[C@@H](C)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "C1(=CC=CC2=CC=CC=C12)[C@@H](C)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-Phenoxybenzaldehyde (2.34 g, 11.8 mmol) and (2R)-2-(1-naphthyl)eth-2-ylamine (2.02 g, 11.8 mmol) were dissolved in methanol (39 mL) under a nitrogen at room temperature. Sodium cyanoborohydride (742 mg, 11.8 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated and the residue was suspe... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | Other | CO | null | 48 | C[C@@H](N)c1cccc2ccccc12.O=Cc1ccc(Oc2ccccc2)cc1>CO>C[C@@H](NCc1ccc(Oc2ccccc2)cc1)c1cccc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-54dca33b1e734c0db0f0cf1ae93a633a | NC1CCCC1.O=Cc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(CNC3CCCC3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C1(CCCC1)N.C(#N)[BH3-].[Na+]>>C1(CCCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1 | [NH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.O=[CH:10][c:9]1[cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][cH:2][cH:1][cH:20][cH:19]2)[cH:18][cH:17]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[cH:19][cH:20]1 | NC1CCCC1.O=Cc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(CNC3CCCC3)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccc(CNC3CCCC3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8] | 83 | [{"value": 83.0, "product": "C1(CCCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "C1(CCCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-Phenoxybenzaldehyde (5.0 g, 25.1 mmol) and cyclopentylamine (2.5 g, 25 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (1.57 g, 25.0 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in ether, washed... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CCCC1 | Other | CO | null | 48 | NC1CCCC1.O=Cc1ccc(Oc2ccccc2)cc1>CO>c1ccc(Oc2ccc(CNC3CCCC3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a49a6c730e16434c9a15d096a5231002 | NC1CCCCC1.O=Cc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(CNC3CCCCC3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C1(CCCCC1)N.C(#N)[BH3-].[Na+]>>C1(CCCCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1 | [NH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1.O=[CH:10][c:9]1[cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][cH:2][cH:1][cH:21][cH:20]2)[cH:19][cH:18]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][cH:21]1 | NC1CCCCC1.O=Cc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(CNC3CCCCC3)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccc(CNC3CCCCC3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8] | 91 | [{"value": 91.0, "product": "C1(CCCCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "C1(CCCCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-Phenoxybenzaldehyde (5.0 g, 25.0 mmol) and cyclohexylamine (2.5 g, 25 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (1.57 g, 25.0 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated and the residue was suspended in ether, washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | Other | CO | null | 48 | NC1CCCCC1.O=Cc1ccc(Oc2ccccc2)cc1>CO>c1ccc(Oc2ccc(CNC3CCCCC3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-177cb84a92d74866aee80467cbd5f6da | NC1CCC1.O=Cc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(CNC3CCC3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C1(CCC1)N.C(#N)[BH3-].[Na+]>>C1(CCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1 | [NH2:11][CH:12]1[CH2:13][CH2:14][CH2:15]1.O=[CH:10][c:9]1[cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][cH:2][cH:1][cH:19][cH:18]2)[cH:17][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH:12]3[CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1 | NC1CCC1.O=Cc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(CNC3CCC3)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccc(CNC3CCC3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8] | 89 | [{"value": 89.0, "product": "C1(CCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "C1(CCC1)NCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-Phenoxybenzaldehyde (5.0 g, 25.0 mmol) and cyclobutylamine (1.8 g, 25.0 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (1.57 g, 25.0 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in ether, washe... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CCC1 | Other | CO | null | 48 | NC1CCC1.O=Cc1ccc(Oc2ccccc2)cc1>CO>c1ccc(Oc2ccc(CNC3CCC3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ea73044c63c247cfa1553acc1af2b233 | O=C(NCc1ccc(Oc2ccccc2)cc1)C1CCC1>>c1ccc(Oc2ccc(CNCC3CCC3)cc2)cc1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].O(C1=CC=CC=C1)C1=CC=C(CNC(=O)C2CCC2)C=C1>>C1(CCC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1 | O=[C:12]([NH:11][CH2:10][c:9]1[cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][cH:2][cH:1][cH:20][cH:19]2)[cH:18][cH:17]1)[CH:13]1[CH2:14][CH2:15][CH2:16]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH2:12][CH:13]3[CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[cH:19][cH:20]1 | O=C(NCc1ccc(Oc2ccccc2)cc1)C1CCC1 | c1ccc(Oc2ccc(CNCC3CCC3)cc2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(Oc2ccc(CNCC3CCC3)cc2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4](-[C:5])-[C:6]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4](-[C:5])-[C:6] | 99.7 | [{"value": 99.0, "product": "C1(CCC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "C1(CCC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A cooled (0° C.) solution of N-(4-phenoxybenzyl)cyclobutanecarboxamide (0.60 g, 2.1 mmol) in THF (7 mL) was treated with 1M solution of LAH in THF (2.1 mL). The solution was refluxed for 2 hours then cooled to 0° C. and quenched with Na2SO4 ·10 H2O. The suspension was diluted with THF and filtered through a pad of celi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccccc1.C1CCC1 | Other | C1CCOC1 | 0 | null | O=C(NCc1ccc(Oc2ccccc2)cc1)C1CCC1>C1CCOC1>c1ccc(Oc2ccc(CNCC3CCC3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b2a826512b824df4ae4a6b01e3820472 | NCC1CCCC1.O=Cc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(CNCC3CCCC3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C1(CCCC1)CN.C(#N)[BH3-].[Na+]>>C1(CCCC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1 | [NH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1.O=[CH:10][c:9]1[cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][cH:2][cH:1][cH:21][cH:20]2)[cH:19][cH:18]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH2:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][cH:21]1 | NCC1CCCC1.O=Cc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(CNCC3CCCC3)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Oc2ccc(CNCC3CCCC3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 80 | [{"value": 80.0, "product": "C1(CCCC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "C1(CCCC1)CNCC1=CC=C(C=C1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-Phenoxybenzaldehyde (3.0 g, 15.1 mmol) and cyclopentylmethylamine (1.49 g, 15.1 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (0.95 g, 15.1 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in ethe... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CCCC1 | Other | CO | null | 48 | NCC1CCCC1.O=Cc1ccc(Oc2ccccc2)cc1>CO>c1ccc(Oc2ccc(CNCC3CCCC3)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-770f231ad0d14d08a4aa547b1860528e | CC(Br)C(=O)Br.O=C1NC2(CCCCC2)Oc2ccccc21>>CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | O.BrC(C(=O)Br)C.N1=CC=CC=C1.C12(CCCCC1)OC1=C(C(N2)=O)C=CC=C1>>BrC(C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C | Br[C:4]([CH:2]([CH3:1])[Br:3])=[O:5].[NH:6]1[C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[O:15][C:16]12[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2>>[CH3:1][CH:2]([Br:3])[C:4](=[O:5])[N:6]1[C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[O:15][C:16]12[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2 | CC(Br)C(=O)Br.O=C1NC2(CCCCC2)Oc2ccccc21 | CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 4a3efee96a9973879eeb72f215a5a85ed9172eb3952927c00f1672e7e7b6a8c1 | e29a64466fcb555fb959b52b849753bd313d8497b31291df296f9d5ed0601ef6 | O=C1NC2(CCCCC2)Oc2ccccc21 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Br;D1;H0:4])-[C;D1;H3:5].[C:6]-[C:7]1(-[C:8])-[#8:9]-[c:10]:[c:11]-[C:12](=[O;D1;H0:13])-[NH;D2;+0:14]-1>>[Br;D1;H0:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[C:12](=[O;D1;H0:13])-[c:11]:[c:10]-[#8:9]-[C:7]-1(-[C:6])-[C:8] | null | [] | null | null | 6 | HOUR | A solution of 89.1 ml of 2-bromopropionyl bromide in 95 ml of methylene chloride and a solution of 61.13 g of pyridine in 95 ml of methylene chloride are added dropwise to a suspension of 140 g of spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one in 190 ml of methylene chloride under nitrogen atmosphere at -5... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amide | Substituted dicarboximide | c1ccc2c(c1)CNC1(CCCCC1)O2 | c1ccc2c(c1)C[NH]C1(CCCCC1)O2 | c1ccc2c(c1)C[NH]C1(CCCCC1)O2 | HBr | C(Cl)Cl | null | 6 | CC(Br)C(=O)Br.O=C1NC2(CCCCC2)Oc2ccccc21>C(Cl)Cl>CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6dfd1fb11b584d67aa30d6766dd60e4c | CC(=O)O[C@H]1NC(=O)[C@@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C.CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2>>C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | C(C)(=O)O[C@@H]1[C@H](C(N1)=O)[C@@H](C)O[Si](C)(C)C(C)(C)C.BrC(C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C.P(=O)([O-])([O-])[O-]>>[Si](C)(C)(C(C)(C)C)O[C@H](C)[C@H]1C(N[C@@H]1[C@H](C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C)=O | CC(=O)O[C@@H:15]1[C@@H:11]([C@@H:2]([CH3:1])[O:3][Si:4]([CH3:5])([CH3:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[C:12](=[O:13])[NH:14]1.Br[CH:16]([CH3:17])[C:18](=[O:19])[N:20]1[C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[O:29][C:30]12[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2>>[CH3:1][C@@H:2]([O:3][Si:4]([CH3:5])... | CC(=O)O[C@H]1NC(=O)[C@@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C.CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | null | [Zn] | O1CCCC1 | C-C Coupling | OtherReaction | 934d5c8109d8b272cd290a8e3b850f0fc7fd702da7fa841c7bbaaad80dd67ba4 | 8caaaad4471a10cdfb4eb5c6637347c9bb8c538dc7d343b47106bac44b31c4f6 | O=C1C[C@@H](CC(=O)N2C(=O)c3ccccc3OC23CCCCC3)N1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]-[#8:9].C-C(=O)-O-[C@H;D3;+0:10]1-[#7:11]-[C:12](=[O;D1;H0:13])-[C:14]-1-[C:15]>>[#8:9]-[C:8]-[#7:5](-[C:3](=[O;D1;H0:4])-[C@H;D3;+0:1](-[C;D1;H3:2])-[C@H;D3;+0:10]1-[#7:11]-[C:12](=[O;D1;H0:13])-[C:14]-1-[C:15])-[C:6]=[O;D1;H0:7] | 74.6 | [{"value": 74.6, "product": "[Si](C)(C)(C(C)(C)C)O[C@H](C)[C@H]1C(N[C@@H]1[C@H](C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g of (3R,4R)-4-acetoxy-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-azetidinone, 1.8 g of 3-(2-bromopropionyl)-spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one and 0.68 g of zinc powders are added to 15 ml of tetrahydrofuran and the mixture is refluxed for 30 minutes. After cooling, the reaction mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | null | C1CNC1 | C1CNC1 | C1CNC1.c1ccc2c(c1)C[NH]C1(CCCCC1)O2 | HBr | [Zn].O1CCCC1 | null | null | CC(=O)O[C@H]1NC(=O)[C@@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C.CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2>[Zn].O1CCCC1>C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-df9f93fd55044e27a55e018b59104c98 | C=CCOC(=O)CN1C(=O)[C@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2.O=P(Cl)(c1ccccc1)c1ccccc1>>C=CCOC(=O)C1=C(OP(=O)(c2ccccc2)c2ccccc2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)C(=O)N12 | C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl.C(C=C)OC(=O)CN1C([C@@H]([C@H]1[C@H](C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C)[C@@H](C)O[Si](C)(C)C(C)(C)C)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].P(=O)([O-])([O-])[O-].C[Si](C)(C)Cl>>C(C=C)OC(=O)C1=C([C@@H]([C@H]2N1C([C@@H]2[C@@H](C)O[Si](C)(C)C(C)(C)C)=O)C)OP(=O)(C2=CC=CC=C2)C2=CC=CC=C2 | O=C1c2ccccc2OC2(CCCCC2)N1[C:8](=[O:9])[C@H:24]([CH3:25])[C@@H:26]1[C@@H:27]([C@@H:28]([CH3:29])[O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[C:38](=[O:39])[N:40]1[CH2:7][C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6].Cl[P:10](=[O:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:2... | C=CCOC(=O)CN1C(=O)[C@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2.O=P(Cl)(c1ccccc1)c1ccccc1 | C=CCOC(=O)C1=C(OP(=O)(c2ccccc2)c2ccccc2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)C(=O)N12 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 137f1afc2fa09b0b68fc33051ed46013e316704cb51a783aab249bf57603ffa3 | 4dbd335fe3986212ab042fae91fe667ffa5e097df1f2314090d80422a11bf8f6 | O=C1C[C@H]2CC(OP(=O)(c3ccccc3)c3ccccc3)=CN12 | Cl-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8].O=C1-N(-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11](-[C;D1;H3:12])-[C:13]2-[C:14]-[C:15](=[O;D1;H0:16])-[#7:17]-2-[CH2;D2;+0:18]-[C:19](=[O;D1;H0:20])-[#8:21]-[C:22]-[C:23]=[C;D1;H2:24])-C2(-C-C-C-C-C-2)-O-c2:c:c:c:c:c:2-1>>[C;D1;H2:24]=[C:23]-[C:22]... | 89.2 | [{"value": 89.2, "product": "C(C=C)OC(=O)C1=C([C@@H]([C@H]2N1C([C@@H]2[C@@H](C)O[Si](C)(C)C(C)(C)C)=O)C)OP(=O)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -50 | CELSIUS | 2 | MINUTE | A solution of 1.2 g of 3-{(2R)-2-[(3S,4R)-1-allyloxycarbonylmethyl-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one in 6 ml of tetrahydrofuran is added dropwise to 4.4 ml of 1M sodium bis(trimethylsilyl)amide solution (solvent:tetrahydrofu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Substituted dicarboximide | Enamine.Ester | c1ccc2c(c1)CNC1(CCCCC1)O2 | C1=CN2CC[C@H]2C1 | c1ccccc1.c1ccccc1.C1=CN2CC[C@H]2C1 | HCl | O1CCCC1 | -50 | 0.033333 | C=CCOC(=O)CN1C(=O)[C@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)[C@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2.O=P(Cl)(c1ccccc1)c1ccccc1>O1CCCC1>C=CCOC(=O)C1=C(OP(=O)(c2ccccc2)c2ccccc2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)C(=O)N12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5b13a10d0eaf45bda3b64b36e98e4245 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2.OO>>C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@H]1[C@@H](C)C(=O)O | [Si](C)(C)(C(C)(C)C)O[C@H](C)[C@H]1C(N[C@@H]1[C@H](C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C)=O.OO.[OH-].[Li+].S(=O)([O-])[O-].[Na+].[Na+]>>[Si](C)(C)(C(C)(C)C)O[C@H](C)[C@H]1C(N[C@H]1[C@H](C(=O)O)C)=O | O=C1c2ccccc2OC2(CCCCC2)N1[C:18]([C@@H:16]([C@@H:15]1[C@@H:11]([C@@H:2]([CH3:1])[O:3][Si:4]([CH3:5])([CH3:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[C:12](=[O:13])[NH:14]1)[CH3:17])=[O:19].O[OH:20]>>[CH3:1][C@@H:2]([O:3][Si:4]([CH3:5])([CH3:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[C@H:11]1[C:12](=[O:13])[NH:14][C@H:15]1[C@@H:16]([C... | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2.OO | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@H]1[C@@H](C)C(=O)O | null | null | O1CCCC1.O | Acylation | OtherReaction | f6981d0d335014fde43e7a57c474643e0e54a441995d98ebecb3f7156f15f743 | 5274a55d4b8d76963ac90069b4bae7fcca82bab65f7971fea72524f2d2221649 | O=C1CCN1 | O-[OH;D1;+0:1].O=C1-N(-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[C:6]-[#7:7])-C2(-C-C-C-C-C-2)-O-c2:c:c:c:c:c:2-1>>[#7:7]-[C:6]-[C:4](-[C;D1;H3:5])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | To a solution of 500 mg of 3-[(2R)-2-[(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one in 20 ml of a mixture of tetrahydrofuran and water are added 0.9 ml of 30% aqueous hydrogen peroxide and 84 mg of lithium hydroxide in this orde... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Substituted dicarboximide.Peroxide | Carboxylic acid | c1ccc2c(c1)CNC1(CCCCC1)O2 | null | C1CNC1 | HO- | O1CCCC1.O | null | 1 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2.OO>O1CCCC1.O>C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@H]1[C@@H](C)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3fb4f783a47b4440a5964fe51d2b85da | CC(=O)O[C@H]1NC(=O)[C@@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C.CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2>>C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | C(C)(=O)O[C@@H]1[C@H](C(N1)=O)[C@@H](C)O[Si](C)(C)C(C)(C)C.BrC(C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C.BrCCBr.Cl.[NH4+].II.[Mg].BrCCBr>>[Si](C)(C)(C(C)(C)C)O[C@H](C)[C@H]1C(N[C@@H]1[C@H](C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C)=O | CC(=O)O[C@@H:15]1[C@@H:11]([C@@H:2]([CH3:1])[O:3][Si:4]([CH3:5])([CH3:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[C:12](=[O:13])[NH:14]1.Br[CH:16]([CH3:17])[C:18](=[O:19])[N:20]1[C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[O:29][C:30]12[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2>>[CH3:1][C@@H:2]([O:3][Si:4]([CH3:5])... | CC(=O)O[C@H]1NC(=O)[C@@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C.CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 934d5c8109d8b272cd290a8e3b850f0fc7fd702da7fa841c7bbaaad80dd67ba4 | 8caaaad4471a10cdfb4eb5c6637347c9bb8c538dc7d343b47106bac44b31c4f6 | O=C1C[C@@H](CC(=O)N2C(=O)c3ccccc3OC23CCCCC3)N1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]-[#8:9].C-C(=O)-O-[C@H;D3;+0:10]1-[#7:11]-[C:12](=[O;D1;H0:13])-[C:14]-1-[C:15]>>[#8:9]-[C:8]-[#7:5](-[C:3](=[O;D1;H0:4])-[C@H;D3;+0:1](-[C;D1;H3:2])-[C@H;D3;+0:10]1-[#7:11]-[C:12](=[O;D1;H0:13])-[C:14]-1-[C:15])-[C:6]=[O;D1;H0:7] | 80.4 | [{"value": 80.4, "product": "[Si](C)(C)(C(C)(C)C)O[C@H](C)[C@H]1C(N[C@@H]1[C@H](C(=O)N1C(C2=C(OC13CCCCC3)C=CC=C2)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | null | null | A mixture of 10 ml of tetrahydrofuran and a small amount of iodine is added to 437 mg of magnesium piece at a room temperature and 0.75 g of 1,2-dibromoethane are added dropwise thereto with stirring. When the exothermic reaction starts and the mixture begins to reflux, a solution of 1.51 g of 1,2-dibromoethane in 3 ml... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | null | C1CNC1 | C1CNC1 | C1CNC1.c1ccc2c(c1)C[NH]C1(CCCCC1)O2 | HBr | O1CCCC1 | 5 | null | CC(=O)O[C@H]1NC(=O)[C@@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C.CC(Br)C(=O)N1C(=O)c2ccccc2OC12CCCCC2>O1CCCC1>C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=O)N1C(=O)c2ccccc2OC12CCCCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ef0f13707ef34c53bd28617536850e4e | CCCCC(=O)CCCC.NC(=O)c1ccccc1O>>CCCCC1(CCCC)NC(=O)c2ccccc2O1 | C(CCC)C(=O)CCCC.C(C=1C(O)=CC=CC1)(=O)N.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(CCC)C1(OC2=C(C(N1)=O)C=CC=C2)CCCC | O=[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][CH2:8][CH3:9].[NH2:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[OH:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([CH2:6][CH2:7][CH2:8][CH3:9])[NH:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19]1 | CCCCC(=O)CCCC.NC(=O)c1ccccc1O | CCCCC1(CCCC)NC(=O)c2ccccc2O1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 3b4fe11943bc84131838449824c33d8fe0b015f531fb0ebdde090ed1985125bc | 15b8d6e5520705f94c812c68b8535efbbcb5e83561a4735812823115f98573f8 | O=C1NCOc2ccccc21 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[C:3]-[C:2]-[C;H0;D4;+0:1]1(-[C:4]-[C:5])-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](:[c:12])-[O;H0;D2;+0:11]-1 | 92.5 | [{"value": 92.5, "product": "C(CCC)C1(OC2=C(C(N1)=O)C=CC=C2)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 20 g of dibutylketone, 19.3 g of salicylamide and 2.7 g of p-toluenesulfonic acid monohydrate is added to 300 ml of toluene and the mixture is refluxed overnight by making use of a dehydrator of Dean Stark. After cooling, the reaction mixture is washed, dried and evaporated to remove the solvent. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amide.Aromatic alcohol | Ether.Secondary amide | null | c1ccc2c(c1)CNCO2 | c1ccc2c(c1)CNCO2 | HO- | C1(=CC=CC=C1)C | null | null | CCCCC(=O)CCCC.NC(=O)c1ccccc1O>C1(=CC=CC=C1)C>CCCCC1(CCCC)NC(=O)c2ccccc2O1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5e4ae90f66b74d139519af7c403855c6 | CNc1ccccc1C(=O)C(=O)O.N>>CNc1ccccc1C(N)=O | CNC=1C(=CC=CC1)C(=O)C(=O)O.O.N>>C(N)(=O)C1=C(NC)C=CC=C1 | O=C(O)[C:9]([c:8]1[c:3]([NH:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:11].[NH3:10]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9]([NH2:10])=[O:11] | CNc1ccccc1C(=O)C(=O)O.N | CNc1ccccc1C(N)=O | null | null | C(C)O | Acylation | OtherReaction | 0644747e3653e03bbd4c6934b952689b181e4b636a04a0e3fb4e4ad3e13c88a7 | 153ec722dad78a6fb85fb5179e9232e2bc15f11ce4479962db767f01e6b4e03d | c1ccccc1 | O-C(=O)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 84.8 | [{"value": 84.8, "product": "C(N)(=O)C1=C(NC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 10.0 g of N-methylisatic acid are added gradually to 140 ml of water at a room temperature and 9.6 g of aqueous ammonia are added dropwise thereto. The mixture is warmed to a temperature of 80° C. during 45 minutes and ethanol is added thereto until the reaction mixture becomes colorless. Then, the reaction mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Primary amide | null | null | c1ccccc1 | HO- | C(C)O | 80 | null | CNc1ccccc1C(=O)C(=O)O.N>C(C)O>CNc1ccccc1C(N)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8ffa93c5ef86417abed9b6bb2c6c17f9 | BrCc1ccccc1.O=[N+]([O-])C1CCCCC1>>O=[N+]([O-])C1(Cc2ccccc2)CCCCC1 | [N+](=O)([O-])C1CCCCC1.C(C1=CC=CC=C1)Br.[H-].[Na+]>>C(C1=CC=CC=C1)C1(CCCCC1)[N+](=O)[O-] | Br[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[O:1]=[N+:2]([O-:3])[CH:4]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[O:1]=[N+:2]([O-:3])[C:4]1([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | BrCc1ccccc1.O=[N+]([O-])C1CCCCC1 | O=[N+]([O-])C1(Cc2ccccc2)CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 4017d0837c741071e92555abe57e582cc596960fc1f0e1439cf05f2f1d366a99 | ece99c5888cee1df1d5b922963d1d81ef8e6789bc50587c1ae41a9ed1b3d07b6 | c1ccc(CC2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH;D3;+0:7](-[#7;+:8](-[O;-;D1;H0:9])=[O;D1;H0:10])-[C:11]-[C:12]>>[C:5]-[C:6]-[C;H0;D4;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[#7;+:8](-[O;-;D1;H0:9])=[O;D1;H0:10])-[C:11]-[C:12] | null | [] | null | null | null | null | Nitrocyclohexane and benzylbromide are subjected to condensation reaction in the presence of sodium hydride to obtain 1-benzyl-1-nitrocyclohexane. The product is reduced with lithium aluminum hydride to obtain 1-benzyl-1-aminocyclohexane. The product is reacted with methyl chloroformate to obtain 1-benzyl-1-methoxycarb... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitro group | Nitro group | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCc1ccccc1.O=[N+]([O-])C1CCCCC1>>O=[N+]([O-])C1(Cc2ccccc2)CCCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5422d02ba274468e9cbcc2a86183416e | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.OC1C2CC3CC(C2)CC1C3>>O=C(Cl)OC1C2CC3CC(C2)CC1C3 | C12C(C3CC(CC(C1)C3)C2)O.ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O.N1=CC=CC=C1>>C12C(C3CC(CC(C1)C3)C2)OC(=O)Cl | ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)[Cl:3])=[O:1].[OH:4][CH:5]1[CH:6]2[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11]2)[CH2:12][CH:13]1[CH2:14]3>>[O:1]=[C:2]([Cl:3])[O:4][CH:5]1[CH:6]2[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11]2)[CH2:12][CH:13]1[CH2:14]3 | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.OC1C2CC3CC(C2)CC1C3 | O=C(Cl)OC1C2CC3CC(C2)CC1C3 | null | null | C(Cl)Cl | Acylation | OtherReaction | 60794a39c0440c00ffe5af45ae1081850b5b3af5d64dc511aaf170d549f5caf2 | 9d38fe5aab6982b32703d33609e218d4ba6d7a679c958162c14445bc8a2a5539 | C1C2CC3CC1CC(C2)C3 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-[Cl;H0;D1;+0:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:3])=[O;D1;H0:2])-[C:7] | null | [] | null | null | 2 | HOUR | To a stirred solution of 2-adamantanol (0.912 g, 6 mmol) in dry CH2Cl2 (15 mL) was added bis(trichloromethyl)carbonate (0.653 g), pyridine in dry CH2Cl2 (10 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for two hours. The solvent was removed in vacuo at 30° C., taken up in ethyl acetate (... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Secondary alcohol | Acyl halide.Ether | null | null | C1C2CC3CC1CC(C2)C3 | HCl | C(Cl)Cl | null | 2 | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.OC1C2CC3CC(C2)CC1C3>C(Cl)Cl>O=C(Cl)OC1C2CC3CC(C2)CC1C3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d93af08881164c99bf70705b0ae41ad0 | COC(=O)[C@](C)(N)Cc1c[nH]c2ccccc12.O=C(Cl)OC1C2CC3CC(C2)CC1C3>>COC(=O)[C@@](C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 | C12C(C3CC(CC(C1)C3)C2)OC(=O)Cl.COC([C@](N)(CC1=CNC2=CC=CC=C12)C)=O.C(C)N(CC)CC>>COC([C@](NC(=O)OC1C2CC3CC(CC1C3)C2)(CC2=CNC3=CC=CC=C23)C)=O | [CH3:1][O:2][C:3](=[O:4])[C@@:5]([CH3:6])([CH2:7][c:8]1[cH:9][nH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12)[NH2:17].Cl[C:18](=[O:19])[O:20][CH:21]1[CH:22]2[CH2:23][CH:24]3[CH2:25][CH:26]([CH2:27]2)[CH2:28][CH:29]1[CH2:30]3>>[CH3:1][O:2][C:3](=[O:4])[C@@:5]([CH3:6])([CH2:7][c:8]1[cH:9][nH:10][c:11]2[cH:12][cH:13][c... | COC(=O)[C@](C)(N)Cc1c[nH]c2ccccc12.O=C(Cl)OC1C2CC3CC(C2)CC1C3 | COC(=O)[C@@](C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 | null | null | C1CCOC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(NCCc1c[nH]c2ccccc12)OC1C2CC3CC(C2)CC1C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[C;D1;H3:7])(-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:6](-[C:5])(-[C;D1;H3:7])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | 89 | [{"value": 89.0, "product": "COC([C@](NC(=O)OC1C2CC3CC(CC1C3)C2)(CC2=CNC3=CC=CC=C23)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "COC([C@](NC(=O)OC1C2CC3CC(CC1C3)C2)(CC2=CNC3=CC=CC=C23)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution of 2-adamantylchloroformate (0.965 g, 4.5 mmol) in dry THF (10 mL) was added a solution of α-methyl-D-tryptophan methyl ester (0.928 g, 4 mmol) in dry THF (20 mL) followed by a solution of triethylamine (0.808 g, 8 mmol) in dry THF (20 mL) dropwise. After 15 minutes, the reaction mixture was filte... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | HCl | C1CCOC1 | null | 0.25 | COC(=O)[C@](C)(N)Cc1c[nH]c2ccccc12.O=C(Cl)OC1C2CC3CC(C2)CC1C3>C1CCOC1>COC(=O)[C@@](C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f453f1c2f5cf421d8b90d3c2e43c436c | COC(=O)[C@@](C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3>>C[C@](Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O | COC([C@](NC(=O)OC1C2CC3CC(CC1C3)C2)(CC2=CNC3=CC=CC=C23)C)=O.[Li+].[OH-]>>C12C(C3CC(CC(C1)C3)C2)OC(=O)N[C@](CC2=CNC3=CC=CC=C23)(C(=O)O)C | C[O:29][C:27]([C@@:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28]>>[CH3:1][C@:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)([NH:13][C:14](=[O:15]... | COC(=O)[C@@](C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 | C[C@](Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O | null | null | O1CCOCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCCc1c[nH]c2ccccc12)OC1C2CC3CC(C2)CC1C3 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 90 | [{"value": 90.0, "product": "C12C(C3CC(CC(C1)C3)C2)OC(=O)N[C@](CC2=CNC3=CC=CC=C23)(C(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "C12C(C3CC(CC(C1)C3)C2)OC(=O)N[C@](CC2=CNC3=CC=CC=C23)(C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of N-[(2-adamantyloxy)carbonyl]-α-methyl-D-tryptophan methyl ester (1.36 g, 3.3 mmol) in aqueous 1,4-dioxan (1:2) (20 mL) was added an excess of LiOH (0.210 g, 5 mmol) and stirred at room temperature overnight. After removing the solvent in vacuo the residue was chromatographed using 5% MeOH:95% C... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | Other | O1CCOCC1 | null | 8 | COC(=O)[C@@](C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3>O1CCOCC1>C[C@](Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a69ca275761d4c46a111a322f087a9f1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.NCCc1ccccc1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1ccccc1 | C1=CC=C(C=C1)CCN.C1(CCCCC1)N=C=NC1CCCCC1.C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)NC(CC1=CNC2=CC=CC=C12)(C(=O)O)C.FC1=C(C(=C(C(=C1O)F)F)F)F>>C1=CC=CC=2C3=CC=CC=C3C(C12)COC(NC(C(NCCC1=CC=CC=C1)=O)(C)CC1=CNC2=CC=CC=C12)=O | O[C:31]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH2:17][CH:18]1[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2-[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21)=[O:32].[NH2:33][CH2:34][CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1>>[CH3:1][C:2]([CH2:3][c:... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.NCCc1ccccc1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1ccccc1 | null | null | C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccc1)OCC1c2ccccc2-c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | 75 | [{"value": 75.0, "product": "C1=CC=CC=2C3=CC=CC=C3C(C12)COC(NC(C(NCCC1=CC=CC=C1)=O)(C)CC1=CNC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.3, "product": "C1=CC=CC=2C3=CC=CC=C3C(C12)COC(NC(C(NCCC1=CC=CC=C1)=O)(C)CC1=CNC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 0 | CELSIUS | 10 | MINUTE | To a solution of N-[(9H-fluoren-9-ylmethyloxy)-carbonyl]-α-methyl-DL-tryptophan (8.80 g, 20 mmol) in dry ethyl acetate (350 mL) was added pentafluorophenol (3.68 g, 20 mmol) and stirred for 10 minutes. The reaction mixture was cooled to 0° C. and a solution of dicyclohexylcarbodiimide (20 mmol) in ethyl acetate (25 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HO- | C(C)(=O)OCC | 0 | 0.166667 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.NCCc1ccccc1>C(C)(=O)OCC>CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6f4a8f6f927b494c8555f6160b05f82a | CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1ccccc1>>CC(N)(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccc1 | C1=CC=CC=2C3=CC=CC=C3C(C12)COC(NC(C(NCCC1=CC=CC=C1)=O)(C)CC1=CNC2=CC=CC=C12)=O>>NC(C(=O)NCCC1=CC=CC=C1)(CC1=CNC2=CC=CC=C12)C | O=C(OCC1c2ccccc2-c2ccccc21)[NH:3][C:2]([CH3:1])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12)[C:14](=[O:15])[NH:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][C:2]([NH2:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12)[C:14](=[O:15])[NH:16][CH2:17][CH... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1ccccc1 | CC(N)(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccc1 | null | null | CN(C)C=O.N1CCCCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 6b8c76d50ec667b483b13f7e325104eed6ba06fddb821da46e405c5dce0a3de5 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(CCc1c[nH]c2ccccc12)NCCc1ccccc1 | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8]>>[C:8]-[#7:7]-[C:5](=[O;D1;H0:6])-[C:2](-[C:3])(-[C;D1;H3:4])-[NH2;D1;+0:1] | null | [] | null | null | 12 | HOUR | (±)-9H-Fluoren-9-ylmethyl[1-(1H-indol-3-yl-methyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl]carbamate (10 g, 18.4 mmol) was dissolved in a 20% piperidine in DMF solution (50 mL) and stirred for 12 hours at room temperature. The solvent was removed in vacuo and chromatographed over silica gel using CH2Cl2 then 5% Me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | CN(C)C=O.N1CCCCC1 | null | 12 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)NCCc1ccccc1>CN(C)C=O.N1CCCCC1>CC(N)(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f39fa40df6d94eeeb92c097c78f691fa | CCOC(=O)c1cc2ccccc2[nH]1.Cc1ccc(S(=O)(=O)Cl)cc1>>CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1 | [H-].[Na+].C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)OC(=O)C=1NC2=CC=CC=C2C1>>C(C)OC(=O)C=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[nH:14]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21]([CH3:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21]([CH3... | CCOC(=O)c1cc2ccccc2[nH]1.Cc1ccc(S(=O)(=O)Cl)cc1 | CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1 | null | null | C1CCOC1 | Acylation | OtherReaction | 1f9175819c9c0179267ecae12f340317ed0385d3996f36daaf36cb61a5ef4625 | b7cf703ff8ec1befb0c6e5230d29d7904f3e22c3606b15633c7e7a7fc4abca48 | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[c:13]:[c:14](:[c:15]):[nH;D2;+0:16]:1>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[c:13]:[c:14](:[c:15]):[n;H0;D3;+0:16]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 30 | CELSIUS | null | null | To a stirred suspension of sodium hydride (3.7 g, 120 mmol, 80% in paraffin oil) in dry THF (75 mL), a solution of indol-2-carboxylic acid ethyl ester (18.9 g, 100 mmol) in dry THF (75 mL) was added in 1 hour with stirring while the inner temperature was maintained under 30° C. The reaction mixture was stirred for 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HCl | C1CCOC1 | 30 | null | CCOC(=O)c1cc2ccccc2[nH]1.Cc1ccc(S(=O)(=O)Cl)cc1>C1CCOC1>CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-386fbb8af4ca43cdb25308b3915df4f2 | CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1>>Cc1ccc(S(=O)(=O)n2c(CO)cc3ccccc32)cc1 | COCCO[AlH2-]OCCOC.[Na+].C(C)OC(=O)C=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C.[OH-].[Na+]>>OCC=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C | CCO[C:11]([c:10]1[n:9]([S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]2)(=[O:7])=[O:8])[c:19]2[c:14]([cH:13]1)[cH:15][cH:16][cH:17][cH:18]2)=[O:12]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[c:10]([CH2:11][OH:12])[cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[cH:20][cH:21]1 | CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1 | Cc1ccc(S(=O)(=O)n2c(CO)cc3ccccc32)cc1 | null | null | C1CCOC1 | Functional Group Interconversion | Reduction of ester to primary alcohol | cd99347e3144bc4f081bc664a4bc5a11d1e392f7cea47a5adad92bcd498ccf56 | a2b5cf843cfeb048c76ac4cbf0bd8ccab026fcad80259b78e012cdb6ac2f5934 | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5](-[#16:6]):[c:7]>>[#16:6]-[#7;a:5](:[c:7]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | 99.1 | [{"value": 98.0, "product": "OCC=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.1, "product": "OCC=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1 | HOUR | To stirred solution of Red-Al (sodium dihydro-bis(2-methoxyethoxy)aluminate ≈70% in toluene) (30 mL) in dry THF (100 mL) cooled at 5° C. and under nitrogen was added dropwise and at this temperature a solution of compound of step 1 (26,8 g, 78 mmol) in dry THF (75 mL). After stirring one hour at 5° C. and then one hour... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cc2ccccc2[nH]1 | HO- | C1CCOC1 | 5 | 1 | CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1>C1CCOC1>Cc1ccc(S(=O)(=O)n2c(CO)cc3ccccc32)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-266e50a932c6448ca0b6e09d8c15259d | BrBr.Cc1ccc(S(=O)(=O)n2c(CO)cc3ccccc32)cc1>>Cc1ccc(S(=O)(=O)n2c(CBr)cc3ccccc32)cc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrBr.OCC=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C>>BrCC=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C | Br[Br:12].O[CH2:11][c:10]1[n:9]([S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]2)(=[O:7])=[O:8])[c:19]2[c:14]([cH:13]1)[cH:15][cH:16][cH:17][cH:18]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[c:10]([CH2:11][Br:12])[cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[cH:20][cH:21]1 | BrBr.Cc1ccc(S(=O)(=O)n2c(CO)cc3ccccc32)cc1 | Cc1ccc(S(=O)(=O)n2c(CBr)cc3ccccc32)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | Br-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5](-[#16:6]):[c:7]>>[#16:6]-[#7;a:5](:[c:7]):[c:3](-[CH2;D2;+0:2]-[Br;H0;D1;+0:1]):[c:4] | 75 | [{"value": 75.0, "product": "BrCC=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.9, "product": "BrCC=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of triphenylphosphine (20.2 g, 77 mmol) in dry CH2Cl2 (80 mL) was added dropwise a solution of bromine (11.9 g, 77 mmol) in dry CH2Cl2 (40 mL). The stirring was continued for one hour and then a solution of compound of step 2 (23.2 g, 77 mmol) in dry CH2Cl2 (40 mL) was added dropwise. The resulting mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.c1cc2ccccc2[nH]1 | HBr | C(Cl)Cl | null | 1 | BrBr.Cc1ccc(S(=O)(=O)n2c(CO)cc3ccccc32)cc1>C(Cl)Cl>Cc1ccc(S(=O)(=O)n2c(CBr)cc3ccccc32)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3c31591d8d9c4f3eb5de5bcf47f0d752 | COC(=O)CBr.NCCc1ccccc1>>COC(=O)CNCCc1ccccc1 | C1(=CC=CC=C1)CCN.BrCC(=O)OC>>C1(=CC=CC=C1)CCNCC(=O)OC | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | COC(=O)CBr.NCCc1ccccc1 | COC(=O)CNCCc1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 308780347cfd56717124ea78bf2bc5de380db774d7ce948246e279dfd7d8998b | d2327a8d30a39f085182e5e2f77f5b022ac99c077866b86103acfec639a8f73d | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5] | 124.2 | [{"value": 61.0, "product": "C1(=CC=CC=C1)CCNCC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 124.2, "product": "C1(=CC=CC=C1)CCNCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirred solution of 2-phenylethylamine (9.68 g, 40 mmol) in toluene (50 mL) was added methyl bromoacetate (6.12 g, 20 mmol) dropwise at room temperature and was left stirring for 18 hours. The reaction mixture was filtered before removing the solvent in vacuo and the residue was purified by chromatography over sil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | HBr | C1(=CC=CC=C1)C | null | 18 | COC(=O)CBr.NCCc1ccccc1>C1(=CC=CC=C1)C>COC(=O)CNCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ab45568062e14e43bc0af4cc036d0a63 | CC(C(=O)[O-])N(CCc1ccccc1)C(=O)C(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)N(CCc1ccccc1)CC(=O)O | CC(N(CCC1=CC=CC=C1)C(C(NC(=O)OC1C2CC3CC(CC1C3)C2)CC2=CNC3=CC=CC=C23)=O)C(=O)[O-].O1CCOCC1>>N1C=C(C2=CC=CC=C12)CC(C(=O)N(CC(=O)O)CCC1=CC=CC=C1)(NC(=O)OC1C2CC3CC(CC1C3)C2)C | [CH3:1][CH:38]([N:29]([C:27]([CH:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28])[CH2:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[C:39](=[O:40])[O-:41]>>[CH3:1][C:2]([... | CC(C(=O)[O-])N(CCc1ccccc1)C(=O)C(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)N(CCc1ccccc1)CC(=O)O | null | null | O | Miscellaneous | OtherReaction | a6b8ab131e7f70f6daa606d152ad1c80317c30ce07f436c723a799e222d8098f | d003579d88c8e6390ed4fac608b8ce68d334559ff02e2f3d9c9936750b60a874 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccc1)OC1C2CC3CC(C2)CC1C3 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[CH;D3;+0:5](-[#7:6]-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13])-[CH;D3;+0:14](-[CH3;D1;+0:15])-[C:16](-[O-;H0;D1:17])=[O;D1;H0:18]>>[#7;a:1]:[c:2]:[c:3]-[C:4]-[C;H0;D4;+0:5](-[CH3;D1;+0:15])(-[#7:6]-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13])-[CH... | null | [] | null | null | 8 | HOUR | To a stirred solution of methyl N-[α-methyl-N-[(tricyclo[3.3.1.13,7 ]dec-2-yloxycarbonyl)-DL-tryptophyl]-N-(2-phenylethyl)glycinate (285 mg, 0.5 mmol) in dioxane (10 mL) and water (5 mL) was added lithium hydroxide-1-hydrate (42 mg, 1.0 mmol) and the resulting mixture was stirred overnight at room temperature. The reac... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | O | null | 8 | CC(C(=O)[O-])N(CCc1ccccc1)C(=O)C(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3>O>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)N(CCc1ccccc1)CC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-89ae05b32ec94fadbcc22995fc36e11b | COC(=O)CCCCCCBr.NCCc1ccccc1>>COC(=O)CCCCCCNCCc1ccccc1 | C1(=CC=CC=C1)CCN.C(C)N(CC)CC.BrCCCCCCC(=O)OC>>C1(=CC=CC=C1)CCNCCCCCCC(=O)OC | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:11][CH2:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | COC(=O)CCCCCCBr.NCCc1ccccc1 | COC(=O)CCCCCCNCCc1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 26.2 | [{"value": 20.0, "product": "C1(=CC=CC=C1)CCNCCCCCCC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.2, "product": "C1(=CC=CC=C1)CCNCCCCCCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 2-phenylethylamine (1.09 g, 9 mmol) and triethylamine (1.37 g, 13.5 mmol) in toluene (50 mL) was added methyl 7-bromoheptanoate (2.0 g, 9 mmol) and refluxed overnight. The reaction mixture was filtered and concentrated. Flash column chromatography over silica gel using 100% ethyl acetate yielded a yello... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HBr | C1(=CC=CC=C1)C | null | null | COC(=O)CCCCCCBr.NCCc1ccccc1>C1(=CC=CC=C1)C>COC(=O)CCCCCCNCCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ec6145a255664335915be7c1b2524232 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1c[nH]c2ccccc12>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1c[nH]c2ccccc12 | NCCC1=CNC2=CC=CC=C12.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.O.ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1>>N1C=C(C2=CC=CC=C12)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][nH:34][c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]12>>[CH3:1][C:2]([CH2:3][... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1c[nH]c2ccccc12 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1c[nH]c2ccccc12 | null | null | CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1c[nH]c2ccccc12)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | null | [] | null | null | 2 | HOUR | A solution of 0.50 g (1.26 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.19 g (1.41 mmol) of 1-hydroxybenzotriazole hydrate in 20 mL of anhydrous EtOAc (under a N2 atmosphere) was treated in one portion with 0.34 g (1.65 mmol) of 1,3-dicyclohexylcarbodiimide. The mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CCOC(=O)C | null | 2 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1c[nH]c2ccccc12>CCOC(=O)C>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1c[nH]c2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d6658f2698654fc0a437607638f2d895 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1csc2ccccc12>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1csc2ccccc12 | Cl.NCCC=1C2=C(SC1)C=CC=C2.CCN(CC)CC.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>S1C2=C(C(=C1)CCNC(C(C)(CC1=CNC3=CC=CC=C13)NC(OC1C3CC4CC(CC1C4)C3)=O)=O)C=CC=C2 | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][s:34][c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]12>>[CH3:1][C:2]([CH2:3][c... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1csc2ccccc12 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1csc2ccccc12 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1csc2ccccc12)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | null | [] | null | null | 2 | HOUR | A solution of 0.50 g (1.26 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.18 g (1.33 mmol) of 1-hydroxybenzotriazole hydrate in 8 mL of anhydrous DMF (under a N2 atmosphere) was treated in one portion with 0.27 g (1.41 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2sccc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C)C=O | null | 2 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1csc2ccccc12>CN(C)C=O>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1csc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3716252ef2a643b6ab21d4714a4aaae6 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1nc2ccccc2[nH]1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1nc2ccccc2[nH]1 | C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.Cl.Cl.N1C(=NC2=C1C=CC=C2)CCN>>N1C(=NC2=C1C=CC=C2)CCNC(C(C)(CC2=CNC1=CC=CC=C21)NC(OC2C1CC3CC(CC2C3)C1)=O)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[n:33][c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]2[nH:40]1>>[CH3:1][C:2]([CH2:3][c... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1nc2ccccc2[nH]1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1nc2ccccc2[nH]1 | null | null | C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1nc2ccccc2[nH]1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | null | [] | null | null | null | null | Following the procedure of Example 70, the title compound was prepared from 0.50 g (1.26 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.33 g (1.41 mmol) of 1H-benzimidazole-2-ethanamine dihydrochloride with 0.5 mL of added triethylamine. The purified product after chromatography was obtained as a white fo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2[nH]cnc2c1.C1C2CC3CC1CC(C2)C3 | HO- | C(C)N(CC)CC | null | null | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1nc2ccccc2[nH]1>C(C)N(CC)CC>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1nc2ccccc2[nH]1 |
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