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-01dbb772c5e249108f0b191ed17a2c0c | ord-5c78bd6caf8a486a9043ac61fe6070d4 | COC(=O)c1cc(N=Nc2ccc(O)c(CC(=O)O)c2)cc(C(=O)OC)c1>>O=C(O)Cc1cc(N=Nc2cc(C(=O)O)cc(C(=O)O)c2)ccc1O | Cl.COC(=O)C=1C=C(C=C(C1)C(=O)OC)N=NC=1C=CC(=C(C1)CC(=O)O)O.[OH-].[Na+].C(C)O>>C(=O)(O)C=1C=C(C=C(C1)C(=O)O)N=NC=1C=CC(=C(C1)CC(=O)O)O | C[O:15][C:13]([c:12]1[cH:11][c:10]([N:9]=[N:8][c:7]2[cH:6][c:5]([CH2:4][C:2](=[O:1])[OH:3])[c:24]([OH:25])[cH:23][cH:22]2)[cH:21][c:17]([C:18](=[O:19])[O:20]C)[cH:16]1)=[O:14]>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][c:7]([N:8]=[N:9][c:10]2[cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21]... | COC(=O)c1cc(N=Nc2ccc(O)c(CC(=O)O)c2)cc(C(=O)OC)c1 | O=C(O)Cc1cc(N=Nc2cc(C(=O)O)cc(C(=O)O)c2)ccc1O | null | null | O | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(N=Nc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | null | [] | null | null | null | null | 12 g of 5-(3,5-bis-(methoxycarbonyl)-phenylazo)-2-hydroxyphenylacetic acid, 350 ml of water and 7 g of sodium hydroxide were boiled for 1 hour. 50 ml of ethanol was added, and the solution was diluted with water to 500 ml. The hot solution was acidified with hydrochloric acid to pH 2 and cooled. The crystals were filte... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | O | null | null | COC(=O)c1cc(N=Nc2ccc(O)c(CC(=O)O)c2)cc(C(=O)OC)c1>O>O=C(O)Cc1cc(N=Nc2cc(C(=O)O)cc(C(=O)O)c2)ccc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9c82aae6872744659c78caf24f2a0ad6 | CCCCCCCCCCCCCCCCCC(=O)Cl.COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C.C[Si](C)(C)C(C(N)=O)[Si](C)(C)C>>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1 | O.N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OC)C(=O)OC(C)(C)C.C[Si](C)(C)C(C(=O)N)[Si](C)(C)C.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCCCC | Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].O=C(O[C:39]([CH3:36])([CH3:38])[CH3:40])[NH:20][C@@H:21]([CH3:22])[C:23](=[O:24])[NH:25][C@H:26]([CH2:27][CH2:28][C:29](=[O:30])[OH:31])[C:32](=[O:33])[O:34][CH3:35].C[Si](C)(... | CCCCCCCCCCCCCCCCCC(=O)Cl.COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C.C[Si](C)(C)C(C(N)=O)[Si](C)(C)C | CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 79687e5242406d951d7886a91bed1f19dbc2bca5d0e30d5496a256a9346dedfe | fcaa19b137429f92b8346d5f48791a190e230bf573cce3aba467a16e8d190d3f | c1ccccc1 | C-[Si](-C)(-[CH3;D1;+0:1])-C(-C(-N)=O)-[Si](-C)(-C)-[CH3;D1;+0:2].Cl-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]-[C:6].O=C(-O-[C;H0;D4;+0:7](-[CH3;D1;+0:8])(-[CH3;D1;+0:9])-[CH3;D1;+0:10])-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])-[C:14](=[O;D1;H0:15])-[#7:16]-[C:17]-[C:18](=[O;D1;H0:19])-[#8:20]-[CH3;D1;+0:21]>>[C:6]-[C:5]-[C;H0;D3;... | 196.4 | [{"value": 196.4, "product": "N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | L-Ala-D-Glu(OH)OBzl (1) (942 mg) was suspended in methylene chloride (40 ml), and bis(trimethylsilyl)acetamide (1.20 g) was added to the suspension under stirring. The resulting solution was treated with stearoyl chloride (900 mg) at ambient temperature and left for an hour. Evaporation of the solvent gave an oily resi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbamic ester.Ester.Ether.Primary amide.Silyl protective group.Silyl protective group.Boc | Ester.Secondary amide | null | c1ccccc1 | c1ccccc1 | HCl | C(Cl)Cl | null | null | CCCCCCCCCCCCCCCCCC(=O)Cl.COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C.C[Si](C)(C)C(C(N)=O)[Si](C)(C)C>C(Cl)Cl>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cb80480d56a947c299041233295b2f80 | CCN(CC)CC.CCOC(C)=O.COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C.N#CC(=NOC(=O)OCc1ccccc1)c1ccccc1>>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)ON=C(C#N)C1=CC=CC=C1.CC(=O)C.N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OC)C(=O)OC(C)(C)C.C(C)N(CC)CC.C(C)(=O)OCC.CC(=O)C>>N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCCCC | N([CH2:5][CH3:6])([CH2:8][CH3:7])[CH2:9][CH3:10].CC(=O)O[CH2:2][CH3:1].CO[C:32]([C@H:26]([NH:25][C:23]([C@@H:21]([NH:20][C:18](OC(C)([CH3:3])[CH3:4])=[O:19])[CH3:22])=[O:24])[CH2:27][CH2:28][C:29](=[O:30])[OH:31])=[O:33].N#C[C:17](=NOC(=O)[O:34][CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1)[c:16]1[cH:11][cH:12][c... | CCN(CC)CC.CCOC(C)=O.COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C.N#CC(=NOC(=O)OCc1ccccc1)c1ccccc1 | CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1 | null | null | O | C-C Coupling | OtherReaction | 4a9b44a97d0825ad133e04f968f43e586a6a2f1aedc9a93b20947f82d74efb97 | b5d0b90a6f4148262c9e5836e06b3e8e6957025f553178e7c59f86821fe08133 | c1ccccc1 | C-C(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2].C-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5](-[C:6])-[#7:7]-[C:8](=[O;D1;H0:9])-[C:10]-[#7:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-O-C(-C)(-[CH3;D1;+0:14])-[CH3;D1;+0:15].N#C-[C;H0;D3;+0:16](=N-O-C(=O)-[O;H0;D2;+0:17]-[C:18]-[c:19])-[c;H0;D3;+0:20]1:[cH;D2;+0:21]:[cH;D2;+0:22]:[cH;D2;+0:23]:[cH... | 94.7 | [{"value": 94.7, "product": "N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-mesoDAP-(L)-GlyOH (1) (1.2 g) in water (5 ml) was added triethylamine (0.96 g) and a solution of benzyloxycarbonyloxyimino-2-phenylacetonitrile (0.69 g) in acetone (5 ml) at 0° C. with stirring and the mixture was stirring over night at room temperature. After evapolation ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ester.Ether.Ether.Nitrile.Tertiary amine.Boc | Ester.Secondary amide | c1ccccc1 | null | c1ccccc1 | HO- | O | null | null | CCN(CC)CC.CCOC(C)=O.COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C.N#CC(=NOC(=O)OCc1ccccc1)c1ccccc1>O>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-34b5a02bca8a409287c4f086e8e5d348 | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1.O=C1CCC(=O)N1O>>CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCc1ccccc1 | N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC.ON1C(CCC1=O)=O.C1(CCCCC1)N=C=NC1CCCCC1>>N([C@@H](C)C(=O)N[C@H](CCC(ON1C(=O)CCC1=O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC | O[C:27]([CH2:26][CH2:25][C@@H:24]([NH:23][C:21]([C@@H:19]([NH:18][C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17])[CH3:20])=[O:22])[C:37](=[O:38])[O:39][CH2:40][c:41]1[cH:42][cH:43][cH:44][cH:45][cH:46]1)=[O:28].[OH:29][N:30]1[C:31](=[O:32])[... | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1.O=C1CCC(=O)N1O | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCc1ccccc1 | null | null | C(Cl)(Cl)Cl.O1CCCC1 | Protection | OtherReaction | a1b3ee4184fc00a0730e4c14eca3a5fbe87fccb44744074c13ef1bfbfabde8ad | e66168e1cfeb6611d93ee4c49193aae81e56c700a9fe46743dc42eed291ed0f9 | O=C(CCCC(=O)ON1C(=O)CCC1=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-1-[OH;D1;+0:12]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:12]-[#7:11]1-[C:6](=[O;D1;H0:5])-[C:7]-[C:8]-[C:9]-1=[O;D1;H0:10] | 7,846.1 | [{"value": 7846.1, "product": "N([C@@H](C)C(=O)N[C@H](CCC(ON1C(=O)CCC1=O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of palmitoyl-L-Ala-D-Glu(OH)OBzl (1)(1.84 g) in a mixture of tetrahydrofuran (20 ml) and chloroform (30 ml) were added N-hydroxysuccinimide (425 mg) and dicyclohexylcarbodiimide (728 mg). The reaction mixture was kept for 18 hours at room temperature and the precipitate was filtered off and washed with ch... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1CC[NH]C1.c1ccccc1 | HO- | C(Cl)(Cl)Cl.O1CCCC1 | null | 18 | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1.O=C1CCC(=O)N1O>C(Cl)(Cl)Cl.O1CCCC1>CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d88a184952ed4e1682e3d74fe14b493c | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1.O=C(O)C(F)(F)F>>CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCc1ccccc1 | FC(C(=O)O)(F)F.N([C@@H](C)C(=O)N[C@H](CCC(O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC>>N([C@@H](C)C(=O)N[C@H](CCC(ON1C(=O)CCC1=O)=O)C(=O)OCC1=CC=CC=C1)C(=O)CCCCCCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[NH:18][C@@H:19]([CH3:20])[C:21](=[O:22])[NH:23][C@H:24]([CH2:25][CH2:26][C:27](=[O:28])[OH:29])[C:37](=[O:38])[O:39][CH2:40][c:41]1[cH:42][cH:43][cH:44][cH:45][cH:46]1.F[C:33](F)(F)[C:31](=[O:3... | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1.O=C(O)C(F)(F)F | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCc1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 9d3882c6f12a0d957247cb9225c824b01f6b123c7e5aaf01a4ad60230ac408bf | 36f812227431b4b24986bca594ef04a41a9f0a5ee5ecfdc1ed90862121d89990 | O=C(CCCC(=O)ON1C(=O)CCC1=O)OCc1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[#7:9]1-[C:10](=[O;H0;D1;+0:4])-[C:11]-[CH2;D2;+0:1]-[C;H0;D3;+0:2]-1=[O;D1;H0:3] | null | [] | null | null | 20 | MINUTE | Trifluoroacetic acid (15 ml) was added to Boc-L-Ala-D-Glu-(OH)OBzl (1)(3.26 g) and the mixture was stirred for 20 minutes at room temperature, concentrated in vacuo and washed with diisopropylether. The oil was dissolved in a mixture of water (15 ml) and sodium bicarbonate was added until the pH of the solution became ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Carboxylic acid | Tertiary amide.Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | null | null | null | 0.333333 | CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1.O=C(O)C(F)(F)F>>CCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-eb26a125028f488199001eac7c1803da | CC(C)(C)O.CC(Cl)OC(=O)Cl>>CC(Cl)OC(=O)OC(C)(C)C | C(C)(C)(C)O.ClC(=O)OC(C)Cl.N1=CC=CC=C1>>C(OC(C)Cl)(OC(C)(C)C)=O | [OH:7][C:8]([CH3:9])([CH3:10])[CH3:11].Cl[C:5]([O:4][CH:2]([CH3:1])[Cl:3])=[O:6]>>[CH3:1][CH:2]([Cl:3])[O:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11] | CC(C)(C)O.CC(Cl)OC(=O)Cl | CC(Cl)OC(=O)OC(C)(C)C | null | null | ClCCl | Acylation | Schotten-Baumann to ester | eac78f0277d3f2b491018dfae1981b579de8768cdcc1514a8c4792e129567220 | 85f668b80fab38c365fc662c1a9c233064a6757d7f126fae63f41481cb03e343 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[OH;D1;+0:9]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:6](-[C;D1;H3:5])(-[C;D1;H3:7])-[C;D1;H3:8] | null | [] | null | null | null | null | In a reactor cooled to +5° C., there are introduced 600 ml of dicloromethane, 43.7 g (0.59 mole) of tert-butanol and 94.7 g (0.66 mole) of α-chloroethyl chloroformate. 57 g (0.72 mole) of pyridine are then added dropwise and with stirring while the temperature is maintained at between 10° and 20° C. The mixture is stir... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Tertiary alcohol | Carbonic Ester | null | null | null | HCl | ClCCl | null | null | CC(C)(C)O.CC(Cl)OC(=O)Cl>ClCCl>CC(Cl)OC(=O)OC(C)(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c4542c72534e465fbfebfb91c898577a | C1CCNCC1.CC(Cl)OC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1CCCCC1 | N1CCCCC1.C(=O)([O-])[O-].[K+].[K+].C(OC(C)Cl)(OC(C)(C)C)=O>>C(C)(C)(C)OC(=O)N1CCCCC1 | [NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.CC(Cl)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | C1CCNCC1.CC(Cl)OC(=O)OC(C)(C)C | CC(C)(C)OC(=O)N1CCCCC1 | null | null | C1CCOC1 | Protection | Boc amine protection of secondary amine | 75e102b122a4a7a02da3ae4e2dcc8358b69efe231b6c70fd0fe46094e3f46d25 | bdffcbfd2f9dfa9a6777281c9c0c2e6d7c7d67c4aae26b320b5d0a73afda621c | C1CCNCC1 | C-C(-Cl)-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].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[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])-[C:11]-[C:12] | null | [] | null | null | null | null | The procedure is as in Example 7, but with 8.5 g (0.1 mole) of piperidine, 60 ml of THF, 20 ml of saturated aqueous K2CO3 solution and 0.11 mole of α-chloroethyl tert-butyl carbonate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carbonic Ester.Secondary amine.Boc | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | C1CCOC1 | null | null | C1CCNCC1.CC(Cl)OC(=O)OC(C)(C)C>C1CCOC1>CC(C)(C)OC(=O)N1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-18ed9719ba5540d59af2fe55eab3dddb | CC(C)(C)OC(=O)OC(Cl)C(Cl)(Cl)Cl.c1c[nH]cn1>>CC(C)(C)OC(=O)c1ncc[nH]1 | C(OC(C)(C)C)(OC(C(Cl)(Cl)Cl)Cl)=O.N1C=NC=C1.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)C=1NC=CN1 | ClC(O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])C(Cl)(Cl)Cl.[cH:8]1[n:9][cH:10][cH:11][nH:12]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[n:9][cH:10][cH:11][nH:12]1 | CC(C)(C)OC(=O)OC(Cl)C(Cl)(Cl)Cl.c1c[nH]cn1 | CC(C)(C)OC(=O)c1ncc[nH]1 | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts acylation | 816926b19e95b508018b448b7a2db217b2d160cb2dbf98aa6d7bdd10b1c1e54d | f06009d448893fe81afd5b89761f51e5f5ed2dc0f5de3026d91db5775be0da30 | c1c[nH]cn1 | Cl-C(-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])-C(-Cl)(-Cl)-Cl.[#7;a:8]1:[c:9]:[c:10]:[#7;a:11]:[cH;D2;+0:12]: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])-[c;H0;D3;+0:12]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | null | [] | 20 | CELSIUS | 1 | HOUR | 5 g (17.5 mmol) of tert-butyl 1,2,2,2-tetrachloroethyl carbonate dissolved in 10 ml of THF are added at 0° C. to a solution of imidazole (1.2 g; 17.6 mmol) in THF (20 ml) in the presence of 5M aqueous potassium carbonate solution (5 ml). The mixture is stirred for 1 hour at 20° C., and the organic phase is decanted and... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary halide.Carbonic Ester.Boc | Ester | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HCl | C1CCOC1 | 20 | 1 | CC(C)(C)OC(=O)OC(Cl)C(Cl)(Cl)Cl.c1c[nH]cn1>C1CCOC1>CC(C)(C)OC(=O)c1ncc[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3c480d95de8546edb218b0eba0488c82 | CC(Cl)OC(=O)Cl.CC1(C)Cc2cccc(O)c2O1>>CC(Cl)OC(=O)Oc1cccc2c1OC(C)(C)C2 | ClC(C)OC(=O)Cl.CC1(OC2=C(C1)C=CC=C2O)C.N1=CC=CC=C1>>C(OC(C)Cl)(OC1=CC=CC=2CC(OC21)(C)C)=O | Cl[C:5]([O:4][CH:2]([CH3:1])[Cl:3])=[O:6].[OH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[O:14][C:15]([CH3:16])([CH3:17])[CH2:18]2>>[CH3:1][CH:2]([Cl:3])[O:4][C:5](=[O:6])[O:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[O:14][C:15]([CH3:16])([CH3:17])[CH2:18]2 | CC(Cl)OC(=O)Cl.CC1(C)Cc2cccc(O)c2O1 | CC(Cl)OC(=O)Oc1cccc2c1OC(C)(C)C2 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 18e63da6830cc445f43af5e9dc21618a6276c35c0e735b25c948aaaf35c35656 | 9d4bf8407389b23766af8e91d21ef1aae6a051b3a051fef2f77a7ae83951845d | c1ccc2c(c1)CCO2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#8:5]-[c:6]:[c:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]):[c:9] | 84 | [{"value": 84.0, "product": "C(OC(C)Cl)(OC1=CC=CC=2CC(OC21)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 3 | HOUR | 21.5 g (0.15 mole) of 1-chloroethylchloroformate are added in a single portion to a solution of 2,3-dihydro-2,2-dimethyl-7-benzofuranol (24.6 g; 0.15 mole) in dichloromethane (150 ml). The mixture is cooled to between 0° and 5° C., and 12 g (0.15 mole) of pyridine are added dropwise. The mixture is stirred for 3 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccc2c(c1)CCO2 | HCl | ClCCl | 20 | 3 | CC(Cl)OC(=O)Cl.CC1(C)Cc2cccc(O)c2O1>ClCCl>CC(Cl)OC(=O)Oc1cccc2c1OC(C)(C)C2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d4106ac42a79474482487a508c64ea90 | CC(Cl)OC(=O)Oc1cccc2c1OC(C)(C)C2.CN(C)c1ccccc1>>CNC(=O)Oc1cccc2c1OC(C)(C)C2 | C(OC(C)Cl)(OC1=CC=CC=2CC(OC21)(C)C)=O.CN(C1=CC=CC=C1)C>>CNC(OC1=CC=CC=2CC(OC21)(C)C)=O | CC(Cl)O[C:3](=[O:4])[O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[O:12][C:13]([CH3:14])([CH3:15])[CH2:16]2.C[N:2](c1ccccc1)[CH3:1]>>[CH3:1][NH:2][C:3](=[O:4])[O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[O:12][C:13]([CH3:14])([CH3:15])[CH2:16]2 | CC(Cl)OC(=O)Oc1cccc2c1OC(C)(C)C2.CN(C)c1ccccc1 | CNC(=O)Oc1cccc2c1OC(C)(C)C2 | null | null | N1=CC=CC=C1 | Protection | OtherReaction | 56c67ed9f08d552b4f5ab0709744a6a0554bc94205da239257b331d0aa710c25 | 1febf5cbaa5b41f12a569b80f68c4e08babe232eeb75eb42efb69ed3b6bc21f1 | c1ccc2c(c1)CCO2 | C-C(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].C-[N;H0;D3;+0:5](-[C;D1;H3:6])-c1:c:c:c:c:c:1>>[C;D1;H3:6]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4] | null | [] | null | null | null | null | The procedure is as in (a) followed by (b), but pyridine is replaced by N,N-dimethylaniline and the intermediate carbonate is not distilled. Starting with 16.4 g of 2,3-dihydro-2,2-dimethyl-7-benzofuranol, 16.8 g (76%) of CARBOFURAN are then obtained, M.p. 147° C.
Conditions: See reaction.notes.procedure_details.
Worku... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether.Ether.Tertiary amine | Carbamic ester | c1ccccc1 | null | c1ccc2c(c1)CCO2 | HCl | N1=CC=CC=C1 | null | null | CC(Cl)OC(=O)Oc1cccc2c1OC(C)(C)C2.CN(C)c1ccccc1>N1=CC=CC=C1>CNC(=O)Oc1cccc2c1OC(C)(C)C2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-15c439ed99fb49c6bfd27dedef4a3286 | CN.O=C(Cl)OC(Cl)C(Cl)(Cl)Cl>>CNC(=O)OC(Cl)C(Cl)(Cl)Cl | CN.ClC(=O)OC(C(Cl)(Cl)Cl)Cl>>CNC(OC(C(Cl)(Cl)Cl)Cl)=O | [CH3:1][NH2:2].Cl[C:3](=[O:4])[O:5][CH:6]([Cl:7])[C:8]([Cl:9])([Cl:10])[Cl:11]>>[CH3:1][NH:2][C:3](=[O:4])[O:5][CH:6]([Cl:7])[C:8]([Cl:9])([Cl:10])[Cl:11] | CN.O=C(Cl)OC(Cl)C(Cl)(Cl)Cl | CNC(=O)OC(Cl)C(Cl)(Cl)Cl | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C;D1;H3:5] | null | [] | null | null | 2 | HOUR | 34.7 ml (0.4 mmol) of methylamine (in 40% strength aqueous solution) are added dropwise to a solution maintained at 0° C. of 49.4 g (0.2 mole) of 1,2,2,2-tetrachloroethyl chloroformate in dichloromethane (150 ml). The mixture is then stirred for 2 hours at room temperature. The organic phase is washed with 2×100 ml of ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | null | HCl | ClCCl | null | 2 | CN.O=C(Cl)OC(Cl)C(Cl)(Cl)Cl>ClCCl>CNC(=O)OC(Cl)C(Cl)(Cl)Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a75633828b0a48b69e9a6ab1c8a89eba | O=C(Cl)OCCCl.c1c[nH]cn1>>CC(Cl)OC(=O)c1ncc[nH]1 | ClC(=O)OCCCl.N1C=NC=C1.ClCCl.O>>ClC(C)OC(=O)C=1NC=CN1 | Cl[C:5]([O:4][CH2:2][CH2:1][Cl:3])=[O:6].[cH:7]1[n:8][cH:9][cH:10][nH:11]1>>[CH3:1][CH:2]([Cl:3])[O:4][C:5](=[O:6])[c:7]1[n:8][cH:9][cH:10][nH:11]1 | O=C(Cl)OCCCl.c1c[nH]cn1 | CC(Cl)OC(=O)c1ncc[nH]1 | null | null | null | Functional Group Interconversion | OtherReaction | 7a66bfe59b3e87f9ced1393a7eb8c64227e0adcdc77dc061f59255ab9be37ce7 | 2079e2b380c74a553dd6ae396541b903f289ebf8d747377df9f4c7bff95f3907 | c1c[nH]cn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[Cl;H0;D1;+0:6].[#7;a:7]1:[c:8]:[c:9]:[#7;a:10]:[cH;D2;+0:11]:1>>[CH3;D1;+0:5]-[CH;D3;+0:4](-[Cl;H0;D1;+0:6])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:11]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | null | [] | null | null | 4 | HOUR | 28.6 g (0.2 mole) of chloroethyl chloroformate are added dropwise to a solution of 27.2 g (0.4 mole) of imidazole in 200 ml of dichloromethane cooled in a water bath. The mixture is stirred at room temperature for 4 hours, and 50 ml of iced water are then added. The organic phase is washed with 2×50 ml of water and the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Ether | Secondary halide.Ester | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HCl | null | null | 4 | O=C(Cl)OCCCl.c1c[nH]cn1>>CC(Cl)OC(=O)c1ncc[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0c0661338a584907b09ee85e49489e40 | CC(C)(C)OC(=O)OC(Cl)C(Cl)(Cl)Cl.N[C@@H](CC(=O)O)C(=O)O>>CC(C)(C)OC(=O)N[C@@H](CC(=O)O)C(=O)O | N[C@@H](CC(=O)O)C(=O)O.O1CCOCC1.O.C(C)N(CC)CC.C(OC(C)(C)C)(OC(C(Cl)(Cl)Cl)Cl)=O>>C(C)(C)(C)OC(=O)N[C@@H](CC(=O)O)C(=O)O | ClC(O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])C(Cl)(Cl)Cl.[NH2:8][C@@H:9]([CH2:10][C:11](=[O:12])[OH:13])[C:14](=[O:15])[OH:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][C:11](=[O:12])[OH:13])[C:14](=[O:15])[OH:16] | CC(C)(C)OC(=O)OC(Cl)C(Cl)(Cl)Cl.N[C@@H](CC(=O)O)C(=O)O | CC(C)(C)OC(=O)N[C@@H](CC(=O)O)C(=O)O | null | null | O | Protection | Boc amine protection of primary amine | 37e16d190b68c39ece6a89d1e9e4bc58f5dd27899c2544e0166ffa6b73bc7e8b | 9b9f365a0cb67affe811fedbc86b1fc402c859f95b93eed7848b69aa4ee65fbd | null | Cl-C(-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])-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:8]-[C:9](-[C:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[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])-[NH;D2;+0:8]-[C:9](-[C:10]-[C:11... | 60 | [{"value": 60.0, "product": "C(C)(C)(C)OC(=O)N[C@@H](CC(=O)O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "C(C)(C)(C)OC(=O)N[C@@H](CC(=O)O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.33 g (10 mmol) of L-aspartic acid in a dioxane/water (1:1) mixture (30 ml), 4.2 ml (30 mmol) of triethylamine are added, and the mixture is stirred until solution is complete (approximately 10 min). 2.85 g (10 mmol) of tert-butyl 1,2,2,2-tetrachloroethyl carbonate are then added and the mixture is st... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary halide.Carbonic Ester.Primary amine | Carbamic ester | null | null | null | HCl | O | null | null | CC(C)(C)OC(=O)OC(Cl)C(Cl)(Cl)Cl.N[C@@H](CC(=O)O)C(=O)O>O>CC(C)(C)OC(=O)N[C@@H](CC(=O)O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9b0ce90354764aed88d683b8b0a391d1 | CC(Cl)OC(=O)OCc1ccco1.CCOC(=O)CN>>CCOC(=O)CNC(=O)OCc1ccco1 | C(OC(C)Cl)(OCC1=CC=CO1)=O.NCC(=O)OCC.O.[Na+].[Cl-]>>C(C1=CC=CO1)OC(=O)NCC(=O)OCC | CC(Cl)O[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][o:16]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH2:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][o:16]1 | CC(Cl)OC(=O)OCc1ccco1.CCOC(=O)CN | CCOC(=O)CNC(=O)OCc1ccco1 | null | null | C([O-])([O-])=O.[K+].[K+].C1CCOC1 | Protection | OtherReaction | 1723d7f7b61a78407ccc5d039d02c2aeebdda75282911635d78cfcb3c9298d34 | 1c0a2d114da0b035f9f98045bd1694b901b7743334178af36300fbe86a79443c | c1ccoc1 | C-C(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[NH2;D1;+0:10]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:7](=[O;D1;H0:8])-[#8:6]-[C:5] | 66 | [{"value": 66.0, "product": "C(C1=CC=CO1)OC(=O)NCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "C(C1=CC=CO1)OC(=O)NCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 2.05 g (10 mmol) of α-chloroethyl furfuryl carbonate are added to a solution of 1.03 g (10 mmol) of ethyl glycinate in 6 ml of THF and 4 ml of 0.5M potassium carbonate solution maintained at between 5° and 10° C. The mixture is allowed to come to room temperature and is stirred for 18 hours. 50 ml of water saturated wi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carbonic Ester.Primary amine | Carbamic ester | null | null | c1ccoc1 | HCl | C([O-])([O-])=O.[K+].[K+].C1CCOC1 | null | 18 | CC(Cl)OC(=O)OCc1ccco1.CCOC(=O)CN>C([O-])([O-])=O.[K+].[K+].C1CCOC1>CCOC(=O)CNC(=O)OCc1ccco1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0390e1237c0d4ce1b863fbe6e79e9218 | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1SCC.O=C(OO)c1cccc(Cl)c1>>CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1S(=O)CC | C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(SCCOCC)SC(C)=O)=O.ClC1=CC(=CC=C1)C(=O)OO>>C(C)S(=O)C1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(SCCOCC)SC(C)=O)=O | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][S:6][C:7]([S:8][C:9]([CH3:10])=[O:11])=[C:12]([C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1)[N:26]1[C:27](=[O:28])[CH2:29][CH:30]1[S:31][CH2:33][CH3:34].O=C(O[OH:32])c1cccc(Cl)c1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][S:6][C:7]([S:8][C:9](... | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1SCC.O=C(OO)c1cccc(Cl)c1 | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1S(=O)CC | null | null | C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | C=C(C(=O)OCc1ccccc1)N1CCC1=O | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6])-[#7:7]1-[C:8](=[O;D1;H0:9])-[C:10]-[C:11]-1-[S;H0;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6])-[#7:7]1-[C:8](=[O;D1;H0:9])-[C:10]-[C:11]-1-[S;H0;D3;+0:12](=[O;H0;D1;+0:1])-[C:13]-[C;D1;H3:14] | null | [] | 0 | CELSIUS | 1 | HOUR | A solution of 1.4 g p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate in 75 ml. methylene chloride was cooled to 0° C. under a nitrogen atmosphere. A solution of 0.551 g m-chloroperbenzoic acid in 25 ml methylene chloride was added dropwise, then the reaction mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccccc1.C1C[NH]C1 | HCl | C(Cl)Cl | 0 | 1 | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1SCC.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1S(=O)CC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-869be1612db248ec8bde7c16dc757fd7 | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1S(=O)CC.O=C(Cl)C(=O)Cl>>CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | C(C)S(=O)C1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(SCCOCC)SC(C)=O)=O.C(C(=O)Cl)(=O)Cl>>ClC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(SCCOCC)SC(C)=O)=O | CCS(=O)[CH:30]1[N:26]([C:12](=[C:7]([S:6][CH2:5][CH2:4][O:3][CH2:2][CH3:1])[S:8][C:9]([CH3:10])=[O:11])[C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]2)[C:27](=[O:28])[CH2:29]1.O=C(Cl)C(=O)[Cl:31]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][S:6][C:7]([S:8][C:9]([CH3:10])=[O:11])=[... | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1S(=O)CC.O=C(Cl)C(=O)Cl | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 7248405afe644c1a2ee565511a16c79f1d77d1fea282d76d510569ecda874877 | 48879576de8a8b2fa13623a529cb30f8c6008d5356f01cd965e9e2a3019acb11 | C=C(C(=O)OCc1ccccc1)N1CCC1=O | C-C-S(=O)-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-1-[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])=[C:10](-[#16:11])-[#16:12]-[C:13](-[C;D1;H3:14])=[O;D1;H0:15].Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:16]>>[#16:11]-[C:10](-[#16:12]-[C:13](-[C;D1;H3:14])=[O;D1;H0:15])=[C:6](-[#7:5]1-[C:3](=[O;D1;H0:4])-[C:2]-[CH;D3;+0:1]-1-[Cl;H0;D1;+0:... | null | [] | null | null | null | null | A solution of 1.2 g p-nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate in 50 ml methylene chloride was cooled to -50° C. under a nitrogen atmosphere. Oxalyl chloride (0.196 ml) was added dropwise at -50° C., then the reaction mixture was allowed to warm to -15°. After 1 hou... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Sulfoxide | Secondary halide | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1 | HCl | C(Cl)Cl | null | null | CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1S(=O)CC.O=C(Cl)C(=O)Cl>C(Cl)Cl>CCOCCSC(SC(C)=O)=C(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5cd096596a2f40b4833d1c38618339f5 | CCOCCSC(=S)[S-].CCSC1CC(=O)N1C(Cl)C(=O)OCc1ccc([N+](=O)[O-])cc1>>CCOCCSC(=S)SC(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1SCC | C(SCCOCC)([S-])=S.[K+].C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])Cl)=O>>C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])SC(=S)SCCOCC)=O | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][S:6][C:7](=[S:8])[S-:9].Cl[CH:10]([C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23]1)[N:24]1[C:25](=[O:26])[CH2:27][CH:28]1[S:29][CH2:30][CH3:31]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][S:6][C:7](=[S:8])[S:9][CH:10]([C:11](=[O:12])[O:13][CH2:14]... | CCOCCSC(=S)[S-].CCSC1CC(=O)N1C(Cl)C(=O)OCc1ccc([N+](=O)[O-])cc1 | CCOCCSC(=S)SC(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1SCC | null | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 38b34234eb49e03ae7a1fdde3465828940ad611ca2c7820b3bbcd591b148f6ec | 745f2b0be08dc7d77c5c1355128858f853bce6044c19247ba807d27934f437f4 | O=C(CN1CCC1=O)OCc1ccccc1 | Cl-[CH;D3;+0:1](-[#7:2]1-[C:3]-[C:4]-[C:5]-1=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[#16:11]-[C:12](-[S-;H0;D1:13])=[S;D1;H0:14]>>[#16:11]-[C:12](=[S;D1;H0:14])-[S;H0;D2;+0:13]-[CH;D3;+0:1](-[#7:2]1-[C:3]-[C:4]-[C:5]-1=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 30.9 | [{"value": 30.9, "product": "C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])SC(=S)SCCOCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 3.58 g potassium 2-ethoxyethyl trithiocarbonate and 3.7 g benzyltriethylammonium chloride in 100 ml methylene chloride was cooled to 0° C. under a nitrogen atmosphere and a solution of 5.3 g of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate in 50 ml methylene chloride was added dropwise.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Thiocarbonyl | Ester.Thiocarbonyl | null | null | c1ccccc1.C1C[NH]C1 | Other | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.C(Cl)Cl | null | 1 | CCOCCSC(=S)[S-].CCSC1CC(=O)N1C(Cl)C(=O)OCc1ccc([N+](=O)[O-])cc1>[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.C(Cl)Cl>CCOCCSC(=S)SC(C(=O)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1SCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e72d089519f840f3b1c92dc784c5a6a9 | CCSC1CC(=O)N1C(O)C(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(Cl)Cl>>CCSC1CC(=O)N1C(Cl)C(=O)OCc1ccc([N+](=O)[O-])cc1 | S(=O)(Cl)Cl.C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])O)=O.CC1=NC(=CC=C1)C>>C(C)SC1CC(N1C(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])Cl)=O | O[CH:9]([N:8]1[CH:4]([S:3][CH2:2][CH3:1])[CH2:5][C:6]1=[O:7])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23]1.O=S(Cl)[Cl:10]>>[CH3:1][CH2:2][S:3][CH:4]1[CH2:5][C:6](=[O:7])[N:8]1[CH:9]([Cl:10])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21... | CCSC1CC(=O)N1C(O)C(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(Cl)Cl | CCSC1CC(=O)N1C(Cl)C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | null | O1CCCC1 | Functional Group Interconversion | Alcohol to chloride_SOCl2 | 120bceabcea6bdd11eaba1f0010d1a819949b303a9b0a1a6f1466a187cd61a7d | 5eacb98c50d3e231ab89acc1b6d4d18d9e568f456953b3682de2c7e4e6b85c60 | O=C(CN1CCC1=O)OCc1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[#7:3]1-[C:4]-[C:5]-[C:6]-1=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:2](-[Cl;H0;D1;+0:1])-[#7:3]1-[C:4]-[C:5]-[C:6]-1=[O;D1;H0:7] | null | [] | null | null | 15 | MINUTE | To a stirred solution of 6.8 g. of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate in 200 ml. of tetrahydrofuran at 0°-5° C. was added 2.98 ml. of 2,6-dimethylpyridine. This was followed by dropwise addition of a solution of 1.73 ml. of thionyl chloride in 20 ml. of tetrahydrofuran, over a 5-minute pe... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Secondary halide | null | null | C1C[NH]C1.c1ccccc1 | HCl | O1CCCC1 | null | 0.25 | CCSC1CC(=O)N1C(O)C(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(Cl)Cl>O1CCCC1>CCSC1CC(=O)N1C(Cl)C(=O)OCc1ccc([N+](=O)[O-])cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-19f79d6d3da9450dae07f2e0f2b882be | CCOCCS.S=C=S>>CCOCCSC(=S)[S-] | CC(C)([O-])C.[K+].C(C)OCCS.C(=S)=S>>C(SCCOCC)([S-])=S.[K+] | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][SH:6].[C:7](=[S:8])=[S:9]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][S:6][C:7](=[S:8])[S-:9] | CCOCCS.S=C=S | CCOCCSC(=S)[S-] | null | null | O1CCCC1 | Functional Group Addition | OtherReaction | 5f4f81b7522510854c92122b358f666f31255d660e00e3337608c3c2cc3fe429 | 0fb8dc55a0761aaea061c344d8eb684ac3fd7c35d8be8b5acd462a6820bdca01 | null | [C:1]-[C:2]-[SH;D1;+0:3].[S;D1;H0:4]=[C;H0;D2;+0:5]=[S;H0;D1;+0:6]>>[C:1]-[C:2]-[S;H0;D2;+0:3]-[C;H0;D3;+0:5](-[S-;H0;D1:6])=[S;D1;H0:4] | null | [] | 25 | CELSIUS | 1 | HOUR | To a solution of 6.79 g potassium t-butoxide in 300 ml of anhydrous tetrahydrofuran cooled to 0° C. under a nitrogen atmosphere was added 6.42 g of 2-mercaptoethyl ethyl ether. The resulting slurry was stirred at 25° C. for 1 hour, then 4.4 ml. of carbon disulfide was added dropwise at 0° C. The resulting solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Aliphatic thiol | Thiocarbonyl | null | null | null | null | O1CCCC1 | 25 | 1 | CCOCCS.S=C=S>O1CCCC1>CCOCCSC(=S)[S-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-00472b5c1cba4539a1ade37a830760de | CC(=O)O.O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CCl>>CC(=O)OCc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O | C(C)(=O)O.C(C)(=O)[O-].[K+].ClCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O.ClCCl>>C(C)(=O)OCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O | [CH3:1][C:2](=[O:3])[OH:4].Cl[CH2:5][c:6]1[n:7][c:8]([CH:9]([Cl:10])[Cl:11])[cH:12][n:13][c:14]1[N:15]1[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]1=[O:25]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][c:8]([CH:9]([Cl:10])[Cl:11])[cH:12][n:13][c:14]1[N:15]1[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][c... | CC(=O)O.O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CCl | CC(=O)OCc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C1c2ccccc2C(=O)N1c1cnccn1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:1-[#7:8](-[C:9]=[O;D1;H0:10])-[C:11]=[O;D1;H0:12].[C;D1;H3:13]-[C:14](=[O;D1;H0:15])-[OH;D1;+0:16]>>[C;D1;H3:13]-[C:14](=[O;D1;H0:15])-[O;H0;D2;+0:16]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:1-[#7:8](-[C:9]=[O;D1;H0:10])-[C:11]=[O;D1;H0:12] | 77 | [{"value": 77.0, "product": "C(C)(=O)OCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 50 ml of absolute glacial acetic acid and 35 g of potassium acetate were added to a solution of 57.7 g (0.16 mole) of 65% strength 3-chloromethyl-5-dichloromethyl-2-phthalimidopyrazine in 1,000 ml of dimethyl sulfoxide, and the mixture was then stirred for three days at room temperature. Thereafter, 1,000 ml of dichlor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1cnccn1.c1ccc2c(c1)C[NH]C2 | HCl | CS(=O)C | null | 72 | CC(=O)O.O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CCl>CS(=O)C>CC(=O)OCc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-25cf147f10cf48b9989fcb580416b649 | CC(=O)OCc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O>>O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO | C(C)(=O)OC.C(C)(=O)OCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC(C=1N=C(C(=NC1)N1C(C=2C(C1=O)=CC=CC2)=O)CO)Cl | CC(=O)[O:22][CH2:21][c:20]1[c:12]([N:11]2[C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[C:9]2=[O:10])[n:13][cH:14][c:15]([CH:16]([Cl:17])[Cl:18])[n:19]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[c:12]1[n:13][cH:14][c:15]([CH:16]([Cl:17])[Cl:18])[n:19][c:20]1[CH2:21][OH:22] | CC(=O)OCc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O | O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C1c2ccccc2C(=O)N1c1cnccn1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[c:3](:[#7;a:4]):[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:3](-[C:2]-[OH;D1;+0:1]):[#7;a:4] | 54 | [{"value": 54.0, "product": "ClC(C=1N=C(C(=NC1)N1C(C=2C(C1=O)=CC=CC2)=O)CO)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "ClC(C=1N=C(C(=NC1)N1C(C=2C(C1=O)=CC=CC2)=O)CO)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 15 g (0.04 mole) of 3-acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine, 150 ml of methanol and 0.15 g of p-toluenesulfonic acid was heated to the boil, and a mixture of methanol and methyl acetate was slowly distilled off in the course of 5 hours. The mixture was then evaporated down to one-third of it... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2c(c1)C[NH]C2.c1cnccn1 | HO- | CO | null | null | CC(=O)OCc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O>CO>O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0e6c16dd3649420f8ec300810a013520 | O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO>>O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O | [Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1.OCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O>>C(=O)C=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O | [OH:1][CH2:2][c:3]1[n:4][c:5]([CH:6]([Cl:7])[Cl:8])[cH:9][n:10][c:11]1[N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22]>>[O:1]=[CH:2][c:3]1[n:4][c:5]([CH:6]([Cl:7])[Cl:8])[cH:9][n:10][c:11]1[N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22] | O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO | O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C1c2ccccc2C(=O)N1c1cnccn1 | [O;D1;H0:1]=[C:2]-[#7:3](-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1-[CH2;D2;+0:10]-[OH;D1;+0:11])-[C:12]=[O;D1;H0:13]>>[O;D1;H0:1]=[C:2]-[#7:3](-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1-[CH;D2;+0:10]=[O;H0;D1;+0:11])-[C:12]=[O;D1;H0:13] | 78 | [{"value": 76.0, "product": "C(=O)C=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "C(=O)C=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | 5.1 g of pyridinium chlorochromate were added a little at a time to a solution of 4 g of 3-hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine in 80 ml of dichloromethane at 35° C., after which the mixture was stirred for 40 minutes and filtered over silica gel, and the filtrate was evaporated down. 3.1 g (76%) of col... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cnccn1.c1ccc2c(c1)C[NH]C2 | null | ClCCl | null | 0.666667 | O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO>ClCCl>O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e962f65fda1a436697d07c873020f372 | NO.O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O>>O=C1c2ccccc2C(=O)N1C1N=CC(C(Cl)Cl)=NC1=NO | C(=O)C=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O.Cl.NO.O>>N(O)=C1C(N=CC(=N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O | [NH2:21][OH:22].O=C[c:20]1[c:12]([N:11]2[C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[C:9]2=[O:10])[n:13][cH:14][c:15]([CH:16]([Cl:17])[Cl:18])[n:19]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH:12]1[N:13]=[CH:14][C:15]([CH:16]([Cl:17])[Cl:18])=[N:19][C:20]1=[N:21][OH:22] | NO.O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O | O=C1c2ccccc2C(=O)N1C1N=CC(C(Cl)Cl)=NC1=NO | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 6b3f184e4728d25b133818806556fb16066cbca25a6ba9e791fb15e323a0f1ad | 39209ce76115b920d674ca536c6ba4e72d7a2b3dfb7f42642512f35ff765fe85 | N=C1N=CC=NC1N1C(=O)c2ccccc2C1=O | O=C-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4](-[Cl;D1;H0:5])-[Cl;D1;H0:6]):[cH;D2;+0:7]:[n;H0;D2;+0:8]:[c;H0;D3;+0:9]:1-[#7:10]1-[C:11](=[O;D1;H0:12])-[c:13]:[c:14]-[C:15]-1=[O;D1;H0:16].[NH2;D1;+0:17]-[O;D1;H1:18]>>[Cl;D1;H0:5]-[C:4](-[Cl;D1;H0:6])-[C;H0;D3;+0:3]1=[N;H0;D2;+0:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:... | 67.4 | [{"value": 65.0, "product": "N(O)=C1C(N=CC(=N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.4, "product": "N(O)=C1C(N=CC(=N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 15 | MINUTE | A solution of 10 g of 3-formyl-5-dichloromethyl-2-phthalimidopyrazine in 50 ml of dimethyl sulfoxide was heated at 50° C., 7 g of hydroxylamine hydrochloride were added, and the mixture was stirred for 15 minutes at 70° C. Thereafter, 700 ml of water were added to the reaction solution, the mixture was filtered and the... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Substituted dicarboximide.Primary amine | Substituted imine.Substituted imine.Substituted dicarboximide.Oxime | c1cnccn1 | C1=NCCN=C1 | c1ccc2c(c1)C[NH]C2.C1=NCCN=C1 | HO- | CS(=O)C | 70 | 0.25 | NO.O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O>CS(=O)C>O=C1c2ccccc2C(=O)N1C1N=CC(C(Cl)Cl)=NC1=NO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8989c551d2d14ccc86118bea21ea1108 | COC(OC)c1cnc(N2C(=O)c3ccccc3C2=O)c(C#N)n1>>COC(OC)c1cnc(N)c(C#N)n1 | O.NN.C(#N)C=1C(=NC=C(N1)C(OC)OC)N1C(C=2C(C1=O)=CC=CC2)=O>>NC1=NC=C(N=C1C#N)C(OC)OC | O=C1c2ccccc2C(=O)[N:10]1[c:9]1[n:8][cH:7][c:6]([CH:3]([O:2][CH3:1])[O:4][CH3:5])[n:14][c:11]1[C:12]#[N:13]>>[CH3:1][O:2][CH:3]([O:4][CH3:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[c:11]([C:12]#[N:13])[n:14]1 | COC(OC)c1cnc(N2C(=O)c3ccccc3C2=O)c(C#N)n1 | COC(OC)c1cnc(N)c(C#N)n1 | null | null | CO | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1cnccn1 | O=C1-[N;H0;D3;+0:1](-[c:2]2:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:2-[C:8]#[N;D1;H0:9])-C(=O)-c2:c:c:c:c:c:2-1>>[N;D1;H0:9]#[C:8]-[c:7]1:[#7;a:6]:[c:5]:[c:4]:[#7;a:3]:[c:2]:1-[NH2;D1;+0:1] | 75.1 | [{"value": 75.0, "product": "NC1=NC=C(N=C1C#N)C(OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "NC1=NC=C(N=C1C#N)C(OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.2 g of hydrazine hydrate were added dropwise to a suspension of 2 g of 3-cyano-5-dimethoxymethyl-2-phthalimidopyrazine in 40 ml of absolute methanol at 40° C. Immediately after the addition, the solution became clear, and crystals were precipitated after a few minutes. Chromatography over silica gel gave 0.9 g (75%) ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1cnccn1 | HO- | CO | null | null | COC(OC)c1cnc(N2C(=O)c3ccccc3C2=O)c(C#N)n1>CO>COC(OC)c1cnc(N)c(C#N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e68e567d6ece4a128886cf5a849df771 | CC(=O)O.O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CCl>>O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO | C(C)(=O)O.C(C)(=O)[O-].[K+].ClCC=1C(=NC=C(N1)C(Cl)Cl)N1C(C=2C(C1=O)=CC=CC2)=O.ClCCl>>ClC(C=1N=C(C(=NC1)N1C(C=2C(C1=O)=CC=CC2)=O)CO)Cl | CC(=O)[OH:22].Cl[CH2:21][c:20]1[c:12]([N:11]2[C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[C:9]2=[O:10])[n:13][cH:14][c:15]([CH:16]([Cl:17])[Cl:18])[n:19]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[c:12]1[n:13][cH:14][c:15]([CH:16]([Cl:17])[Cl:18])[n:19][c:20]1[CH2:21][OH:22] | CC(=O)O.O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CCl | O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | dcda08c3a2df177b88cf2633dca6c592556d271991617ee7f8f5c291332482db | 73605e1c48f69a0b692de7bd8edcecdd32045375b4fa5443073a7ab513760941 | O=C1c2ccccc2C(=O)N1c1cnccn1 | C-C(=O)-[OH;D1;+0:1].Cl-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1-[#7:9](-[C:10]=[O;D1;H0:11])-[C:12]=[O;D1;H0:13]>>[O;D1;H0:13]=[C:12]-[#7:9](-[c:8]1:[#7;a:7]:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[CH2;D2;+0:2]-[OH;D1;+0:1])-[C:10]=[O;D1;H0:11] | 47 | [{"value": 47.0, "product": "ClC(C=1N=C(C(=NC1)N1C(C=2C(C1=O)=CC=CC2)=O)CO)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 50 ml of glacial acetic acid and 35 g of potassium acetate were added to a solution of 57.7 g (0.16 mole) of 65% strength 3-chloromethyl-5-dichloromethyl-2-phthalimidopyrazine in 1,000 ml of a 95:5 dimethyl sulfoxide/water mixture. The mixture was stirred for three days at room temperature, after which 1,000 ml of dich... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Primary alcohol | null | null | c1ccc2c(c1)C[NH]C2.c1cnccn1 | HCl | CS(=O)C.O | null | 72 | CC(=O)O.O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CCl>CS(=O)C.O>O=C1c2ccccc2C(=O)N1c1ncc(C(Cl)Cl)nc1CO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ae89461366744f8aa04b8314f2a33939 | CO.N=C(N)N.Nc1ccnc(N)n1>>N#Cc1cnc2nc(N)nc(N)c2c1 | NC1=NC=CC(=N1)N.NC(=N)N.CO.Cl>>NC=1N=C(C2=C(N1)N=CC(=C2)C#N)N | O[CH3:2].[NH:1]=[C:8]([NH2:9])[NH2:10].N[c:14]1[cH:3][cH:4][n:5][c:6]([NH2:12])[n:7]1>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[n:7][c:8]([NH2:9])[n:10][c:11]([NH2:12])[c:13]2[cH:14]1 | CO.N=C(N)N.Nc1ccnc(N)n1 | N#Cc1cnc2nc(N)nc(N)c2c1 | null | [Pd].Cl[Pd]Cl | CCN(CC)CC.C(C)O.CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 91b4866c3b161f7a208a3bee41df2dac0d574663f05354223179b2100d22bbfa | 58f037c0e173eb90165a8f54fb237e652cce581733f0de7cc15c3f4078bab34e | c1cnc2ncncc2c1 | N-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3]:[#7;a:4]:[c;H0;D3;+0:5](-[NH2;D1;+0:6]):[n;H0;D2;+0:7]:1.O-[CH3;D1;+0:8].[N;D1;H2:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[NH;D1;+0:12]>>[N;D1;H2:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[c:13](-[NH2;D1;+0:6]):[c:14]2:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C;H0;D2;+0:8]#[N;H0;D1;+0:12]):[c:3]:[#7;a:4... | 95 | [{"value": 95.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C#N)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Referring now to Scheme I, compounds 3 and 4 were prepared by reported procedures, which proved to be readily adaptable to large-scale preparations. The reductive dechlorination Steps to give 5 and 6 were done in DMF--MeOH (N,N-dimethylformamide-methyl alcohol) solution containing 5% Pd on BaCO3. This method differs sl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Primary amine.Methanol | Nitrile.Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | null | [Pd].Cl[Pd]Cl.CCN(CC)CC.C(C)O.CN(C)C=O | null | null | CO.N=C(N)N.Nc1ccnc(N)n1>[Pd].Cl[Pd]Cl.CCN(CC)CC.C(C)O.CN(C)C=O>N#Cc1cnc2nc(N)nc(N)c2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f59a2889ea174bf0ac3472c52a9f95d2 | N#Cc1cc(C#N)c(Cl)nc1N>>N#Cc1cnc(N)c(C#N)c1 | NC1=NC(=C(C=C1C#N)C#N)Cl>>NC1=NC=C(C=C1C#N)C#N | Cl[c:4]1[n:5][c:6]([NH2:7])[c:3]([C:2]#[N:1])[cH:11][c:8]1[C:9]#[N:10]>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH2:7])[c:8]([C:9]#[N:10])[cH:11]1 | N#Cc1cc(C#N)c(Cl)nc1N | N#Cc1cnc(N)c(C#N)c1 | null | null | C1CCCCC1.CCOC(=O)C | Miscellaneous | Aromatic dehalogenation | 7e204a847916e0c4c140c562819111cd0e4a9bc61594eac7c0805ff63a367ef2 | f004e58a958e83ed69c0f163c54d2c11d46ff03ec9dbfbb5a519e7e4cb2f94a4 | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-[N;D1;H2:4]):[c;H0;D3;+0:5](-[C:6]#[N;D1;H0:7]):[c:8]:[c;H0;D3;+0:9]:1-[C:10]#[N;D1;H0:11]>>[N;D1;H0:11]#[C:10]-[c;H0;D3;+0:9]1:[c:8]:[c;H0;D3;+0:5](-[C:6]#[N;D1;H0:7]):[cH;D2;+0:1]:[#7;a:2]:[c;H0;D3;+0:3]:1-[N;D1;H2:4] | 73 | [{"value": 73.0, "product": "NC1=NC=C(C=C1C#N)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Amino-3,5-dicyanopyridine (5) was prepared from 3 using the procedure described below for the preparation of 5 except that 5 was recrystallised from MeCN [methyl cyanide; acetonitrile) (instead of EtOH). The yield was 73% (7.00 g from 12.0 g (67.2 mmol) of 3] of product homogeneous on TLC (cyclohexane-EtOAc, 1:1); mp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C1CCCCC1.CCOC(=O)C | null | null | N#Cc1cc(C#N)c(Cl)nc1N>C1CCCCC1.CCOC(=O)C>N#Cc1cnc(N)c(C#N)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-717477a32b7f4cc0977022329f06cd51 | Cc1c(C#N)c(N)nc(Cl)c1C#N>>Cc1c(C#N)cnc(N)c1C#N | NC1=NC(=C(C(=C1C#N)C)C#N)Cl.CO.C1CCCCC1.CCOC(=O)C>>NC1=NC=C(C(=C1C#N)C)C#N | Cl[c:6]1[c:3]([C:4]#[N:5])[c:2]([CH3:1])[c:10]([C:11]#[N:12])[c:8]([NH2:9])[n:7]1>>[CH3:1][c:2]1[c:3]([C:4]#[N:5])[cH:6][n:7][c:8]([NH2:9])[c:10]1[C:11]#[N:12] | Cc1c(C#N)c(N)nc(Cl)c1C#N | Cc1c(C#N)cnc(N)c1C#N | null | [Pd] | CN(C)C=O | Functional Group Interconversion | Aromatic dehalogenation | ea85ec2fde5700c76b45764563e70d433b50e38e1af4209f646f155266c8ec96 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | 86 | [{"value": 86.0, "product": "NC1=NC=C(C(=C1C#N)C)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrogenolysis of 4 (10.0 g, 52.0 mmol) in DMF (150 mL)-MeOH (75 mL) containing 5% Pd on BaCO3 (10.0 g) was carried out in a Parr shaker with H2 pressure kept near 3.5 kg/cm2 (50 psi) for six hours. The mixture was then filtered (Celite mat), and evaporated to dryness (final conditions <1 mm, bath to 45° C.) The residu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | [Pd].CN(C)C=O | null | null | Cc1c(C#N)c(N)nc(Cl)c1C#N>[Pd].CN(C)C=O>Cc1c(C#N)cnc(N)c1C#N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-01537abe3d964860950784242d6215b3 | N#Cc1cnc(N)c(C#N)c1.N=C(N)N>>N#Cc1cnc2nc(N)nc(N)c2c1 | C1CCCCC1.CCOC(=O)C.NC(=N)N.Cl.C[O-].[Na+].NC1=NC=C(C=C1C#N)C#N>>NC=1N=C(C2=C(N1)N=CC(=C2)C#N)N | [N:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH2:7])[c:13]([C:11]#[N:12])[cH:14]1.N[C:8]([NH2:9])=[NH:10]>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[n:7][c:8]([NH2:9])[n:10][c:11]([NH2:12])[c:13]2[cH:14]1 | N#Cc1cnc(N)c(C#N)c1.N=C(N)N | N#Cc1cnc2nc(N)nc(N)c2c1 | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | 4a09d814c35ed57344475f361bf7e51991fe644e5fefeb06eaebd40f1ce7c451 | 1aa7191beb21c0c960b18631a0bd52edc8e0a5e54fb7edd4fc42913ae18d9901 | c1cnc2ncncc2c1 | N-[C;H0;D3;+0:1](-[N;D1;H2:2])=[NH;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[#7;a:10]:[c:11]>>[N;D1;H2:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:5](-[NH2;D1;+0:4]):[c:6](:[c:7]):[c:8](:[#7;a:10]:[c:11]):[n;H0;D2;+0:9]:1 | 95 | [{"value": 95.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C#N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C#N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Guanidine·HCl (2.66 g, 27.8 mmol) was added to a solution of NaOMe (sodium methoxide) (1.50 g, 27.8 mmol) in absolute EtOH (180 mL). The mixture was stirred at 20°-23° C. for 15 minutes before 5 (2.00 g, 13.9 mmol) was added. After a 24-hour reflux period with rapid stirring, TLC (cyclohexane-EtOAc, 1:1) showed absence... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Primary amine | Primary amine | c1ccncc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | Other | CCO | null | null | N#Cc1cnc(N)c(C#N)c1.N=C(N)N>CCO>N#Cc1cnc2nc(N)nc(N)c2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-97248722c0404b71aece60e2bbc0ba59 | Cc1c(C=O)cnc2nc(N)nc(N)c12>>Cc1c(CO)cnc2nc(N)nc(N)c12 | [BH4-].[Na+].NC=1N=C(C2=C(N1)N=CC(=C2C)C=O)N.[BH4-].[Na+].C(C)(=O)[O-].NC=1N=C(C2=C(N1)N=CC(=C2C)C=O)N>>NC=1N=C(C2=C(N1)N=CC(=C2C)CO)N | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][n:7][c:8]2[n:9][c:10]([NH2:11])[n:12][c:13]([NH2:14])[c:15]12>>[CH3:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][n:7][c:8]2[n:9][c:10]([NH2:11])[n:12][c:13]([NH2:14])[c:15]12 | Cc1c(C=O)cnc2nc(N)nc(N)c12 | Cc1c(CO)cnc2nc(N)nc(N)c12 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1cnc2ncncc2c1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4]:[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8] | null | [] | 70 | CELSIUS | 2 | HOUR | NaBH4 (500 mg, 13.2 mmol) was added in portions during a 10 minute interval to a stirred suspension of crude 13 (2.73 g), in MeOH (500 mL) at 20°-23° C. Stirring was continued for two hours, then NaBH4 (500 mg) was again added as before. After the mixture had been stirred overnight, HPLC (acetate buffer of pH 3.6-MeOH,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1cnc2ncncc2c1 | null | CO | 70 | 2 | Cc1c(C=O)cnc2nc(N)nc(N)c12>CO>Cc1c(CO)cnc2nc(N)nc(N)c12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ec77ee8ce6d54d51817a1b5b60ea9228 | CCOC(=O)CC[C@H](NC(=O)c1ccc(N(CC)Cc2cnc3nc(N)nc(N)c3c2C)cc1)C(=O)OCC>>CCN(Cc1cnc2nc(N)nc(N)c2c1C)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | Cl.[OH-].[Na+].COC([C@@H](NC(C1=CC=C(C=C1)N(C)CC1=C(C2=C(N=C(N=C2N)N)N=C1)C)=O)CCC(=O)OC)=O.C(C)OC([C@@H](NC(C1=CC=C(C=C1)N(CC)CC1=C(C2=C(N=C(N=C2N)N)N=C1)C)=O)CCC(=O)OCC)=O>>NC=1N=C(C2=C(N1)N=CC(=C2C)CN(C2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)CC)N | CC[O:30][C:28]([CH2:27][CH2:26][C@H:25]([NH:24][C:22]([c:21]1[cH:20][cH:19][c:18]([N:3]([CH2:2][CH3:1])[CH2:4][c:5]2[cH:6][n:7][c:8]3[n:9][c:10]([NH2:11])[n:12][c:13]([NH2:14])[c:15]3[c:16]2[CH3:17])[cH:35][cH:34]1)=[O:23])[C:31](=[O:32])[O:33]CC)=[O:29]>>[CH3:1][CH2:2][N:3]([CH2:4][c:5]1[cH:6][n:7][c:8]2[n:9][c:10]([N... | CCOC(=O)CC[C@H](NC(=O)c1ccc(N(CC)Cc2cnc3nc(N)nc(N)c3c2C)cc1)C(=O)OCC | CCN(Cc1cnc2nc(N)nc(N)c2c1C)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | null | null | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(NCc2cnc3ncncc3c2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 97 | [{"value": 97.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2C)CN(C2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)CC)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[4-[[(2,4-Diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]ethylamino]benzoyl-L-glutamic acid (21, 5-Methyl-5-deaza-10-ethylaminopterin) was prepared by saponification of 19 as described for the conversion of 18 to 20; yield 97% (56 mg from 60 mg, 0.109 mmol), of 19·0.6H2O, homogeneous by HPLC. Spectral data: mass,... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CCOC(=O)CC[C@H](NC(=O)c1ccc(N(CC)Cc2cnc3nc(N)nc(N)c3c2C)cc1)C(=O)OCC>>CCN(Cc1cnc2nc(N)nc(N)c2c1C)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-097ce1f06049442d8b63f92135cc032e | CCC(C)CCCCCBr.N#Cc1ccc(O)cc1>>CC[C@H](C)CCCCCOc1ccc(C#N)cc1 | C(C(C)CC)O.C([O-])([O-])=O.[K+].[K+].C(#N)C1=CC=C(C=C1)O.BrCCCCCC(CC)C>>C[C@H](CCCCCOC1=CC=C(C#N)C=C1)CC | Br[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:3]([CH2:2][CH3:1])[CH3:4].[OH:10][c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][C@H:3]([CH3:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]1 | CCC(C)CCCCCBr.N#Cc1ccc(O)cc1 | CC[C@H](C)CCCCCOc1ccc(C#N)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Add 5.75 g of 4-cyanophenol 10 g of 1 brom-6-methyl octane synthesized of available active amyl alcohol, 6.67 g of anhydrous potassium carbonate, 30 ml of N,N-dimethyl formamide into 100 ml four-mouth flask under nitrogen atmosphere, allow to react for 8 hours at 110° C. After the reaction, filter the insoluble matter,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | null | null | CCC(C)CCCCCBr.N#Cc1ccc(O)cc1>CN(C=O)C>CC[C@H](C)CCCCCOc1ccc(C#N)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1ff5c11c42b04a318b57cf8f518bbb02 | CCCCCCCCC(C(=O)OCC)C(=O)OCC.CC[C@H](C)CCCCCOc1ccc(C(=N)N)cc1>>CCCCCCCCc1c(O)nc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1O | S(O)(O)(=O)=O.[Na].C(CCCCCCC)C(C(=O)OCC)C(=O)OCC.C[O-].[Na+].Cl.C[C@H](CCCCCOC1=CC=C(C(=N)N)C=C1)CC>>C(CCCCCCC)C=1C(=NC(=NC1O)C1=CC=C(C=C1)OCCCCC[C@H](CC)C)O | CCO[C:10]([CH:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:31](OCC)=[O:32])=[O:11].[NH2:12][C:13]([c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]([CH3:25])[CH2:26][CH3:27])[cH:28][cH:29]1)=[NH:30]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[c:10]... | CCCCCCCCC(C(=O)OCC)C(=O)OCC.CC[C@H](C)CCCCCOc1ccc(C(=N)N)cc1 | CCCCCCCCc1c(O)nc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2ncccn2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C:4]-[C:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-C-C.[NH2;D1;+0:8]-[C;H0;D3;+0:9](=[NH;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:5]-[C:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:1... | null | [] | null | null | null | null | Pour 1.15 g sodium metal, and 33 ml dry methanol into 100 ml four-mouth flask; add 5 g of optically active (s)-4-(6-methyloctyloxy)benzamidine hydrochloric acid salt, then pour 4.55 g of diethyl n-octylmalonate into this sodium methylate solution and then allow to react for 18 hours under heat and reflux conditions. Af... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | CO | null | null | CCCCCCCCC(C(=O)OCC)C(=O)OCC.CC[C@H](C)CCCCCOc1ccc(C(=N)N)cc1>CO>CCCCCCCCc1c(O)nc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e62665853a104cb08a8caeb3781bea61 | CCCCCCCCc1c(Cl)nc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1Cl>>CCCCCCCCc1cnc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1 | C(CCCCCCC)C=1C(=NC(=NC1Cl)C1=CC=C(C=C1)OCCCCC[C@H](CC)C)Cl.[O-2].[Mg+2].C(C)O>>C(CCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)OCCCCC[C@H](CC)C | Cl[c:10]1[c:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:30](Cl)[n:29][c:12](-[c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([CH3:24])[CH2:25][CH3:26])[cH:27][cH:28]2)[n:11]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][n:11][c:12](-[c:13]... | CCCCCCCCc1c(Cl)nc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1Cl | CCCCCCCCc1cnc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1 | null | [C].[Pd] | O | Reduction | OtherReaction | fcc37c9c611ca40bb9c411eab4802374f0106d75bef4c7f56886315f511a7627 | 0ecff68b4ffbd9fa417ba42b220387f06d93399a1e61c4d05eaeeacbdad5d93b | c1ccc(-c2ncccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c;H0;D3;+0:6](-Cl):[c:7]:1-[C:8]>>[C:8]-[c:7]1:[cH;D2;+0:1]:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[cH;D2;+0:6]:1 | null | [] | null | null | null | null | Pour 1.88 g of optically active (s)-5-n-octyl-2-[4-(6-methyloctyloxy)phenyl]-4,6-dichloro-pyrimidine, 0.4 g of 10% palladium-carbon, 0.55 g of magnesium oxide, 60 ml of ethanol, and 45 ml of water, into a 200 ml flask, then add hydrogen under oil bath conditions at 50° C., until the logical amount of hydrogen has been ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | Other | [C].[Pd].O | null | null | CCCCCCCCc1c(Cl)nc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1Cl>[C].[Pd].O>CCCCCCCCc1cnc(-c2ccc(OCCCCC[C@@H](C)CC)cc2)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ae7c4249e17a4e4bb669f0513f28a2f7 | CCCCCCCCBr.CC[C@H](C)CCCCCc1cnc(-c2ccc(O)cc2)nc1>>CCCCCCCCOc1ccc(-c2ncc(CCCCC[C@@H](C)CC)cn2)cc1 | BrCCCCCCCC.C[C@H](CCCCCC=1C=NC(=NC1)C1=CC=C(C=C1)O)CC.[H-].[Na+]>>C(CCCCCCC)OC1=CC=C(C=C1)C1=NC=C(C=N1)CCCCC[C@H](CC)C | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[n:15][cH:16][c:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([CH3:24])[CH2:25][CH3:26])[cH:27][n:28]2)[cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13](-[... | CCCCCCCCBr.CC[C@H](C)CCCCCc1cnc(-c2ccc(O)cc2)nc1 | CCCCCCCCOc1ccc(-c2ncc(CCCCC[C@@H](C)CC)cn2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ncccn2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Pour 0.33 g of sodium hydride (about 50% oil suspension), 3 ml of dry N,N-dimethylformamide into a 30 ml three-mouth flask equipped with a cooling tube, thermometer, dripping funnel, and calcium chloride tube. Next, slowly drip 1.71 g of optically active (s)-4-[5-(6-methyl octyl)-2-pyrimidinyl]phenol which is dissolved... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1cncnc1 | HBr | CN(C=O)C | null | null | CCCCCCCCBr.CC[C@H](C)CCCCCc1cnc(-c2ccc(O)cc2)nc1>CN(C=O)C>CCCCCCCCOc1ccc(-c2ncc(CCCCC[C@@H](C)CC)cn2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0f56b0f450a745bdbb47e42936a87fa7 | CCC(C)C(=O)O.CCCCCCCCCCCOc1cnc(-c2ccc(O)cc2)nc1>>CCCCCCCCCCCOc1cnc(-c2ccc(OC(=O)[C@@H](C)CC)cc2)nc1 | CC(C(=O)O)CC.C(CCCCCCCCCC)OC=1C=NC(=NC1)C1=CC=C(C=C1)O>>C(CCCCCCCCCC)OC=1C=NC(=NC1)C1=CC=C(C=C1)OC([C@H](CC)C)=O | O[C:22](=[O:23])[CH:24]([CH3:25])[CH2:26][CH3:27].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][n:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([OH:21])[cH:28][cH:29]2)[n:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:1... | CCC(C)C(=O)O.CCCCCCCCCCCOc1cnc(-c2ccc(O)cc2)nc1 | CCCCCCCCCCCOc1cnc(-c2ccc(OC(=O)[C@@H](C)CC)cc2)nc1 | null | CN(C1=CC=NC=C1)C | C(Cl)(Cl)Cl | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | c1ccc(-c2ncccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[C:5]-[C;D1;H3:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:4]-[C@@H;D3;+0:3](-[C:5]-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 70 | [{"value": 70.0, "product": "C(CCCCCCCCCC)OC=1C=NC(=NC1)C1=CC=C(C=C1)OC([C@H](CC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pour 0.328 g of 2-methylbutanoic acid synthesized from (s)-amylalcohol ([α]D23 -5.8° (neat)), 1.1 g of 4-(5-n-undecyloxy-2-pyrimidinyl)phenol, 8 ml of anhydrous chloroform and 0.662 g of 4-dimethylaminopyridine, S,S'-dicyclohexylcarbodimide into a 25 ml flask and allow to react for one whole day at room temperature. Af... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1cncnc1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)(Cl)Cl | null | null | CCC(C)C(=O)O.CCCCCCCCCCCOc1cnc(-c2ccc(O)cc2)nc1>CN(C1=CC=NC=C1)C.C(Cl)(Cl)Cl>CCCCCCCCCCCOc1cnc(-c2ccc(OC(=O)[C@@H](C)CC)cc2)nc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8a8737a6ccae4f179fddb28772f1de1a | O=[N+]([O-])c1ccc(F)cc1.Oc1ccc(Cl)cc1F.Oc1ccc(Cl)cc1F>>COC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2F)cc1 | ClC1=CC(=C(C=C1)O)F.ClC1=C(C(=CC=C1)F)O.ClC1=C(C(=CC=C1)F)O.FC1=CC=C(C=C1)[N+](=O)[O-].ClC1=C(C(=C(C=C1)O)F)Cl.ClC1=CC(=C(C=C1)O)F.[Na+].[Cl-].[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>>COC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Cl)F)=O | O=[N+]([O-])[c:5]1[cH:1][cH:21][c:11](F)[cH:10][cH:6]1.F[c:22]1cc(Cl)c[cH:9][c:8]1[OH:7].[OH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]1[F:20]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]2[F:20])[cH:21][cH:22]1 | O=[N+]([O-])c1ccc(F)cc1.Oc1ccc(Cl)cc1F.Oc1ccc(Cl)cc1F | COC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2F)cc1 | null | null | CS(=O)C | Acylation | OtherReaction | a776a8683d28654e58f45ae675e548b46d15281896074843aa88ca157abf261f | f349f833ad04cb89796cc34133cd7b9b734057215e1d693111caa205736c1542 | c1ccc(Oc2ccccc2)cc1 | Cl-c1:c:[cH;D2;+0:1]:[c:2](-[OH;D1;+0:3]):[c;H0;D3;+0:4](-F):c:1.F-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[N+](=O)-[O-]):[cH;D2;+0:9]:[cH;D2;+0:10]:1.[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[CH3;D1;+0:9]-[#8:15]-[C:16](=[O;D1;H0:17])-[CH;D3;+0:8](-[CH3;D1;+0:7])-[O;H0;D2;+0:3]-[c:2]1:[cH;D2;+0:4]:[cH;D... | null | [] | 100 | CELSIUS | 30 | MINUTE | To a stirred mixture of potassium carbonate (25.04 g; 0.18 mol) in DMSO (200 ml) under argon atmosphere was added an 8:2 mixture (25 g; 0.171 mol) (from Step 2A) of 4-chloro-2-fluorophenol (~20 g; 0.136 mol) and 2-chloro-6-fluorophenol (~5 g; 0.034 mol). To this mixture was added 4-fluoronitrobenzene (18.05 g; 0.128 mo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Nitro group.Aromatic alcohol.Aromatic alcohol | Ester.Ether.Ether | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CS(=O)C | 100 | 0.5 | O=[N+]([O-])c1ccc(F)cc1.Oc1ccc(Cl)cc1F.Oc1ccc(Cl)cc1F>CS(=O)C>COC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1f1e5d760a08437fbcdac96714805542 | COC(=O)C(C)Br.Oc1ccc(Oc2ccc(Br)cc2F)cc1>>COC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | O.BrC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F.BrC(C(=O)OC)C.C([O-])([O-])=O.[K+].[K+]>>COC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O | Br[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[OH:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[F:20])[cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[F:20])[cH:21][cH:22]1 | COC(=O)C(C)Br.Oc1ccc(Oc2ccc(Br)cc2F)cc1 | COC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a60236748d2543bdb97e5465447a595cd9bb5fef4e3fe96ed6af652af51cd157 | 94a54f0a6e629a85ca32b8fd3cf243ab64283e31ecfe8705ffe0df2304c488b4 | c1ccc(Oc2ccccc2)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 18 | HOUR | A mixture of the 4-(4-bromo-2-fluorophenoxy)phenol (5.66 g, 0.02 mol) from Step V, methyl 2-bromoproprionate (3.34 g, 0.02 mol) and potassium carbonate (3.06 g, 0.22 mol) in DMSO (30 ml) was stirred, under an atmosphere of nitrogen, at room temperature for 18 hours. The mixture was poured into water (300 ml), and the r... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CS(=O)C | null | 18 | COC(=O)C(C)Br.Oc1ccc(Oc2ccc(Br)cc2F)cc1>CS(=O)C>COC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0f78ba915f35468eaf7efcfa90a652a9 | COC(=O)C(C)O.Oc1ccc(Oc2ccc(Br)cc2F)cc1>>COC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | CS(=O)(=O)[O-].C(C(O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+].BrC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F>>COC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O | O[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[OH:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[F:20])[cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[F:20])[cH:21][cH:22]1 | COC(=O)C(C)O.Oc1ccc(Oc2ccc(Br)cc2F)cc1 | COC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | dcfcc873dea6ee5e165c0ecd29b721f7fe5378b92b644a66f7b493dd677cb7f9 | 23ac5fc1d8cc7460c5f165241138db5f1d60f846b59bf6c4b239ddd29d58ddda | c1ccc(Oc2ccccc2)cc1 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 189.6 | [{"value": 189.6, "product": "COC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the 4-(4-bromo-2-fluorophenoxy)phenol (2.83 g, 0.01 mol), the methanesulfonate of S methyl lactate (18.2 g, 0.01 mol), and potassium carbonate (1.67 g, 0.012 mol) in DMSO (70 ml) was stirred at room temperature for 40 hours, then poured into water (700 ml). The mixture was extracted with ether (2×200 ml). ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1 | HO- | CS(=O)C.O | null | null | COC(=O)C(C)O.Oc1ccc(Oc2ccc(Br)cc2F)cc1>CS(=O)C.O>COC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-127bab2712c94c40b71146c91e151657 | COC(=O)C(C)Oc1ccc(O)cc1.O=[N+]([O-])c1ccc(F)c(F)c1>>COC(=O)C(C)Oc1ccc(Oc2ccc([N+](=O)[O-])cc2F)cc1 | FC=1C=C(C=CC1F)[N+](=O)[O-].OC1=CC=C(OC(C(=O)OC)C)C=C1.C([O-])([O-])=O.[K+].[K+]>>FC1=C(OC2=CC=C(OC(C(=O)OC)C)C=C2)C=CC(=C1)[N+](=O)[O-] | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:23][cH:24]1.F[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]1[F:22]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]2[F:22])... | COC(=O)C(C)Oc1ccc(O)cc1.O=[N+]([O-])c1ccc(F)c(F)c1 | COC(=O)C(C)Oc1ccc(Oc2ccc([N+](=O)[O-])cc2F)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](-[F;D1;H0:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | 98.2 | [{"value": 98.0, "product": "FC1=C(OC2=CC=C(OC(C(=O)OC)C)C=C2)C=CC(=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.2, "product": "FC1=C(OC2=CC=C(OC(C(=O)OC)C)C=C2)C=CC(=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 3,4-difluoronitrobenzene (13.5 g, 0.85 mol), methyl 2-(4-hydroxyphenoxy)propionate (23.1 g, 0.085 mol), and potassium carbonate (12.5 g, 0.09 mol) in DMSO (200 ml) was heated in an oil bath (120° bath temperature) for one hour. After cooling the reaction mixture was poured into ice water (1000 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CS(=O)C | null | null | COC(=O)C(C)Oc1ccc(O)cc1.O=[N+]([O-])c1ccc(F)c(F)c1>CS(=O)C>COC(=O)C(C)Oc1ccc(Oc2ccc([N+](=O)[O-])cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-53fcb22988bf4f00ace4b323695f617b | CCOC(=O)CCC(C)Br.Oc1ccc(Oc2ccc(Cl)cc2F)cc1>>CCOC(=O)CCC(C)Oc1ccc(Oc2ccc(Cl)cc2F)cc1 | C1(=CC=CC=C1)O.Cl.[Br-].C([O-])([O-])=O.ClC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F.BrC(CCC(=O)OCC)C.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC(=C(OC2=CC=C(OC(CCC(=O)OCC)C)C=C2)C=C1)F | Br[CH:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:9].[OH:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]2[F:23])[cH:24][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]([CH3:9])[O:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:... | CCOC(=O)CCC(C)Br.Oc1ccc(Oc2ccc(Cl)cc2F)cc1 | CCOC(=O)CCC(C)Oc1ccc(Oc2ccc(Cl)cc2F)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(Oc2ccccc2)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | 130 | CELSIUS | null | null | A stirred mixture of 4-(4-chloro-2-fluorophenoxy)phenol (2.3 g, 0.0103 mol), ethyl 4-bromopentanoate (2.01 g, 0.0103 mol), and potassium carbonate (1.46 g, 0.105 mol) in DMF (20 ml) was heated in an oil bath at 130° C. for one hour. Additional bromide (0.5 g) and carbonate (0.5 g) were added each hour for the next four... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | 130 | null | CCOC(=O)CCC(C)Br.Oc1ccc(Oc2ccc(Cl)cc2F)cc1>CN(C)C=O>CCOC(=O)CCC(C)Oc1ccc(Oc2ccc(Cl)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b5402a5a3ee14b03bfb946e023674692 | COC(=O)C=C(OC)C(C)Br.Oc1ccc(Oc2ccc(Br)cc2F)cc1>>COC(=O)C=C(OC)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | BrC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F.BrC(C(=CC(=O)OC)OC)C.C([O-])([O-])=O.[K+].[K+].C(C)#N>>BrC1=CC(=C(OC2=CC=C(OC(C(=CC(=O)OC)OC)C)C=C2)C=C1)F | Br[CH:9]([C:6](=[CH:5][C:3]([O:2][CH3:1])=[O:4])[O:7][CH3:8])[CH3:10].[OH:11][c:12]1[cH:13][cH:14][c:15]([O:16][c:17]2[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]2[F:24])[cH:25][cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([O:7][CH3:8])[CH:9]([CH3:10])[O:11][c:12]1[cH:13][cH:14][c:15]([O:16][c:17]2[cH:18][cH:19][c:20](... | COC(=O)C=C(OC)C(C)Br.Oc1ccc(Oc2ccc(Br)cc2F)cc1 | COC(=O)C=C(OC)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(Oc2ccccc2)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](-[#8:4])=[C:5]-[C:6](-[#8:7])=[O;D1;H0:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]=[C:3](-[#8:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 58.2 | [{"value": 58.0, "product": "BrC1=CC(=C(OC2=CC=C(OC(C(=CC(=O)OC)OC)C)C=C2)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.2, "product": "BrC1=CC(=C(OC2=CC=C(OC(C(=CC(=O)OC)OC)C)C=C2)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 12.0 g (42.4 mmol) 4-(4-bromo-2-fluorophenoxy)phenol, 9.5 g (42.4 mmol) methyl 4-bromo-3-methoxy-2-pentenoate, 6.45 g (46.6 mmol) potassium carbonate and 180 ml acetonitrile was heated at reflux for 16 hours. The mixture was poured into water and extracted with ether. The combined ether extracts were washe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | O | null | null | COC(=O)C=C(OC)C(C)Br.Oc1ccc(Oc2ccc(Br)cc2F)cc1>O>COC(=O)C=C(OC)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-06486a43573049c0972d0737d58446eb | COC(=O)C=C(OC)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1>>COC(=CCO)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | C(C)(=O)O.CC(C)C[AlH]CC(C)C.BrC1=CC(=C(OC2=CC=C(OC(C(=CC(=O)OC)OC)C)C=C2)C=C1)F.CCOCC>>BrC1=CC(=C(OC2=CC=C(OC(C(=CCO)OC)C)C=C2)C=C1)F | CO[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:7]([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]2[F:22])[cH:23][cH:24]1)=[O:6]>>[CH3:1][O:2][C:3](=[CH:4][CH2:5][OH:6])[CH:7]([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]2[F:22])[... | COC(=O)C=C(OC)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | COC(=CCO)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | null | null | C1(=CC=CC=C1)C.O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Oc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]=[C:4](-[#8:5])-[C:6]>>[#8:5]-[C:4](-[C:6])=[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 74 | [{"value": 74.0, "product": "BrC1=CC(=C(OC2=CC=C(OC(C(=CCO)OC)C)C=C2)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "BrC1=CC(=C(OC2=CC=C(OC(C(=CCO)OC)C)C=C2)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | To a solution of 4.5 g (10.6 mmol) 4-(4-(4-bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester in 25 ml toluene at -78° C. was added dropwise over a period of 30 min, 16.5 ml of 1.5M DIBAL-H in toluene, keeping the temperature below -60° C. The mixture was stirred for 21/2 hours at -78° C. To the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C1(=CC=CC=C1)C.O | -78 | 2 | COC(=O)C=C(OC)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1>C1(=CC=CC=C1)C.O>COC(=CCO)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fd27dcb7b04c492084da2155de44a546 | COC(=CCO)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1>>C=CC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | BrC1=CC(=C(OC2=CC=C(OC(C(=CCO)OC)C)C=C2)C=C1)F.O>>BrC1=CC(=C(OC2=CC=C(OC(C(C=C)=O)C)C=C2)C=C1)F | C[O:4][C:3](=[CH:2][CH2:1]O)[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[F:20])[cH:21][cH:22]1>>[CH2:1]=[CH:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[F:20])[cH:21][cH:22]1 | COC(=CCO)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | C=CC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | a8d662f969f46443ee3d205eeaa2aad04bcbbc6b5518b3c0c35fba920e940fa2 | 95556fd158731d9953abb86a3541dbd9e9215d18e7d86c5830e4933fdf09f92c | c1ccc(Oc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[CH;D2;+0:3]-[CH2;D2;+0:4]-O)-[C:5](-[#8:6])-[C;D1;H3:7]>>[#8:6]-[C:5](-[C;D1;H3:7])-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[CH;D2;+0:3]=[CH2;D1;+0:4] | 69 | [{"value": 69.0, "product": "BrC1=CC(=C(OC2=CC=C(OC(C(C=C)=O)C)C=C2)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.9, "product": "BrC1=CC(=C(OC2=CC=C(OC(C(C=C)=O)C)C=C2)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | To a solution of 30 ml of 35% HClO4 and 15 ml CH2Cl2 at 0° C. was added 3.0 g (7.55 mmol) 4-(4-(4-bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-penten-1-ol in 15 ml CH2Cl2. The mixture was stirred at 0° C. for 45 min, then poured into water and extracted with ether. The combined ether extracts were washed with water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ketone.Vinyl | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | 0 | 0.75 | COC(=CCO)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1>C(Cl)Cl>C=CC(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0e96676273d2437282408c24a90f4b9f | CC(=O)CC(C)=O.CC(Oc1ccc(Oc2ccc(Br)cc2F)cc1)C(=O)Cl>>CC(=O)C(C(C)=O)C(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | BrC1=CC(=C(OC2=CC=C(OC(C(=O)Cl)C)C=C2)C=C1)F.CC(CC(C)=O)=O.C1=CC=CC=C1.[Na]>>C(C)(=O)C(C(C)=O)C(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O | [CH3:1][C:2](=[O:3])[CH2:4][C:5]([CH3:6])=[O:7].Cl[C:8](=[O:9])[CH:10]([CH3:11])[O:12][c:13]1[cH:14][cH:15][c:16]([O:17][c:18]2[cH:19][cH:20][c:21]([Br:22])[cH:23][c:24]2[F:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[CH:4]([C:5]([CH3:6])=[O:7])[C:8](=[O:9])[CH:10]([CH3:11])[O:12][c:13]1[cH:14][cH:15][c:16]([O:17][c:18]2[... | CC(=O)CC(C)=O.CC(Oc1ccc(Oc2ccc(Br)cc2F)cc1)C(=O)Cl | CC(=O)C(C(C)=O)C(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | null | null | CCOCC.O | C-C Coupling | OtherReaction | 526e6fbc0e961d2a07a8bee2a7a532eb48246fde37e16e5fd7c1b5060d3c2076 | d1ef8d6a572be6944eed6d1e50ba23f9d6e95602669b67dac90442aed5304e90 | c1ccc(Oc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4])-[C;D1;H3:5].[C;D1;H3:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12]>>[#8:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:9](-[C:7](-[C;D1;H3:6])=[O;D1;H0:8])-[C:10](-[C;D1;H3:11])=[O;D1;H0:12] | 16 | [{"value": 16.0, "product": "C(C)(=O)C(C(C)=O)C(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 1.7 g (17 mmol) of 2,4-pentanedione, 30 ml of benzene and 0.26 g (11.3 mmol) of sodium was warmed at reflux for 3 hours. The reaction mixture was cooled to room temperature and a solution of 10 mmol of 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propanoyl chloride was added dropwise. The resulting mixture was wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Ketone | Ketone.Ketone.Ketone | null | null | c1ccccc1.c1ccccc1 | HCl | CCOCC.O | null | 8 | CC(=O)CC(C)=O.CC(Oc1ccc(Oc2ccc(Br)cc2F)cc1)C(=O)Cl>CCOCC.O>CC(=O)C(C(C)=O)C(=O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-203e66a3104e4a1aa4c270e295862ca4 | CC(C=O)Oc1ccc(Oc2ccc(Br)cc2F)cc1.CCOC(C)=O>>CCOC(=O)CC(O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | C(CCC)[Li].BrC1=CC(=C(OC2=CC=C(OC(C=O)C)C=C2)C=C1)F.C(C)(C)NC(C)C.C(C)(=O)OCC.[NH4+].[Cl-]>>C(C)OC(CC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)O)=O | [CH:7](=[O:8])[CH:9]([CH3:10])[O:11][c:12]1[cH:13][cH:14][c:15]([O:16][c:17]2[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]2[F:24])[cH:25][cH:26]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[CH:9]([CH3:10])[O:11][c:12]1[cH:13][cH:14][c:15]([O:16][c:17]2[cH:18][cH:19][c:20]... | CC(C=O)Oc1ccc(Oc2ccc(Br)cc2F)cc1.CCOC(C)=O | CCOC(=O)CC(O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 | null | null | CCCCCC.CCOCC | C-C Coupling | OtherReaction | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | c1ccc(Oc2ccccc2)cc1 | [#8:1]-[C:2](-[C;D1;H3:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5].[C:6]-[#8:7]-[C:8](-[CH3;D1;+0:9])=[O;D1;H0:10]>>[#8:1]-[C:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[CH2;D2;+0:9]-[C:8](=[O;D1;H0:10])-[#8:7]-[C:6] | 70 | [{"value": 70.0, "product": "C(C)OC(CC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 1.54 ml (11 mmol) of diisopropylamine in 20 ml of ether was cooled under N2 to -78° C. and 6.9 ml (11 mmol) of 1.6M n-butyllithium in hexane was slowly added. After 15 min of -78° C. 0.97 g (11 mmol) of ethyl acetate in 3 ml of ether was added dropwise. The resulting mixture was stirred at -78° C. for 15 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | null | CCCCCC.CCOCC | null | 0.25 | CC(C=O)Oc1ccc(Oc2ccc(Br)cc2F)cc1.CCOC(C)=O>CCCCCC.CCOCC>CCOC(=O)CC(O)C(C)Oc1ccc(Oc2ccc(Br)cc2F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fb27c21061f54078be4fc125c2783746 | O=C1Cc2c(Cl)ccc(Cl)c2N1.O=C1Cc2cccc(C3CC3)c2N1>>O=C1Cc2ccc(Cl)cc2N1 | C1(CC1)C=1C=CC=C2CC(NC12)=O.FC1=C2CC(NC2=CC(=C1)F)=O.BrC=1C=CC=C2CC(NC12)=O.CC=1C=CC=C2CC(NC12)=O.ClC1=C2CC(NC2=C(C=C1)Cl)=O.FC=1C=C2CC(NC2=C(C1)F)=O.C1(CCCCC1)C=1C=CC=C2CC(NC12)=O.FC=1C=CC=C2CC(NC12)=O.C(CCC)C=1C=C2CC(NC2=C(C1)F)=O>>ClC1=CC=C2CC(NC2=C1)=O | O=C1C[c:10]2[c:4](Cl)[cH:5][cH:6][c:7]([Cl:8])[c:9]2N1.c1cc(C2CC2)c2c(c1)[CH2:3][C:2](=[O:1])[NH:11]2>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[NH:11]1 | O=C1Cc2c(Cl)ccc(Cl)c2N1.O=C1Cc2cccc(C3CC3)c2N1 | O=C1Cc2ccc(Cl)cc2N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 38442a974c2a8dde1e00166c906a36ef22d9d4944d31152b70b4b12c04f86abf | 7f6fbbbe780e833dd4ad214bddfac885434f3ca11622b2c0bf81fe85651fcf44 | O=C1Cc2ccccc2N1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[Cl;D1;H0:5]):[c;H0;D3;+0:6]2:[c;H0;D3;+0:7]:1-C-C(=O)-N-2.[O;D1;H0:8]=[C:9]1-[CH2;D2;+0:10]-c2:c:c:c:c(-C3-C-C-3):c:2-[NH;D2;+0:11]-1>>[Cl;D1;H0:5]-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1]2:[c;H0;D3;+0:7](:[cH;D2;+0:6]:1)-[NH;D2;+0:11]-[C:9](=[O;D1;H0:8])-[CH2;D2;+0:10]-2 | null | [] | null | null | null | null | In an analogous manner 4- and 6-fluoro- and bromooxindoles are prepared, as well as 7-fluorooxindole, 7-bromooxindole, 7-methyloxindole, 4,6-difluorooxindole, 4,7-dichlorooxindole, 5,7-difluorooxindole, 5-n-butyl-7-fluorooxindole, 7-cyclohexyloxindole and 7-cyclopropyloxindole.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide.Secondary amide | Secondary amide | c1ccc2c(c1)CCN2.C1CC1.c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HCl | null | null | null | O=C1Cc2c(Cl)ccc(Cl)c2N1.O=C1Cc2cccc(C3CC3)c2N1>>O=C1Cc2ccc(Cl)cc2N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-67d46a104ad240b9a00c308bf07eb4cb | Nc1ccc(F)c(Cl)c1.O=C(Cl)CCl>>O=C(CCl)Nc1ccc(F)c(Cl)c1 | ClC=1C=C(N)C=CC1F.N1=CC=CC=C1.ClCC(=O)Cl>>ClCC(=O)NC1=CC(=C(C=C1)F)Cl | [NH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([Cl:12])[cH:13]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([Cl:12])[cH:13]1 | Nc1ccc(F)c(Cl)c1.O=C(Cl)CCl | O=C(CCl)Nc1ccc(F)c(Cl)c1 | null | null | C1(=CC=CC=C1)C | 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]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 88 | [{"value": 88.0, "product": "ClCC(=O)NC1=CC(=C(C=C1)F)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To 130 ml. of toluene was added, with stirring, 24.0 g. (0.165 mole) of 3-chloro-4-fluoroaniline and 13.5 ml. (0.166 mole) of pyridine. The resulting solution was cooled to ca 0° C. and 13.2 ml. (0.166 mole) of 2-chloroacetyl chloride was added. The reaction mixture was stirred at room temperature for 5 hours and then ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | Nc1ccc(F)c(Cl)c1.O=C(Cl)CCl>C1(=CC=CC=C1)C>O=C(CCl)Nc1ccc(F)c(Cl)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-648f109ece9742c68f0c921925e57cde | O=C(CCl)Nc1ccc(F)c(Cl)c1>>O=C1Cc2cc(F)c(Cl)cc2N1 | ClCC(=O)NC1=CC(=C(C=C1)F)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>ClC1=C(C=C2CC(NC2=C1)=O)F | Cl[CH2:3][C:2](=[O:1])[NH:12][c:11]1[cH:4][cH:5][c:6]([F:7])[c:8]([Cl:9])[cH:10]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([F:7])[c:8]([Cl:9])[cH:10][c:11]2[NH:12]1 | O=C(CCl)Nc1ccc(F)c(Cl)c1 | O=C1Cc2cc(F)c(Cl)cc2N1 | null | null | null | Functional Group Interconversion | OtherReaction | 6ab2dca96c05f47f8dd3d6dbe49c7d399a1afbe6dfa21b42d4808f5071f12d2d | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | O=C1Cc2ccccc2N1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:3]=[C:2]1-[#7:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9])-[CH2;D2;+0:1]-1 | 7 | [{"value": 7.0, "product": "ClC1=C(C=C2CC(NC2=C1)=O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A 26.63 g. sample of the N-(2-chloro)-2-chloro-4-fluoroaniline was thoroughly mixed with 64 g. of anhydrous aluminum chloride, and the mixture was heated at 210°-230° C. for 8.5 hours. The reaction mixture was then poured onto a mixture of ice an 1N hydrochloric acid, with stirring. Stirring was continued for 30 minute... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HCl | null | null | 0.5 | O=C(CCl)Nc1ccc(F)c(Cl)c1>>O=C1Cc2cc(F)c(Cl)cc2N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-348a42addcd841a49c39a0b63d7106f4 | CCCCSc1ccccc1N.CCCSc1ccc(N)cc1.CSc1ccccc1N>>CCCc1ccc2c(c1)CC(=S)N2.Cc1ccc2c(c1)NC(=S)C2.Cc1cccc2c1CC(=S)N2 | CSC1=C(N)C=CC=C1.C(CC)SC1=CC=C(N)C=C1.C(CCC)SC1=C(N)C=CC=C1>>CC1=C2CC(NC2=CC=C1)=S.CC1=CC=C2CC(NC2=C1)=S.C(CC)C=1C=C2CC(NC2=CC1)=S | [cH:10]1[cH:24][cH:18][c:19]([NH2:21])[c:33]([S:34][CH2:25][CH2:16][CH2:15][CH3:14])[cH:32]1.[CH3:1][CH2:2][CH2:3][S:23][c:4]1[cH:5][cH:6][c:7]([NH2:13])[cH:8][cH:9]1.[CH3:11][S:12][c:31]1[cH:26][cH:27][cH:28][cH:29][c:30]1[NH2:35]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][C:11](=[S:12])[NH:1... | CCCCSc1ccccc1N.CCCSc1ccc(N)cc1.CSc1ccccc1N | CCCc1ccc2c(c1)CC(=S)N2.Cc1ccc2c(c1)NC(=S)C2.Cc1cccc2c1CC(=S)N2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7c0dcff1756dfc92577737d78827fbdb376e698d49d0dfda48e52fca279b70f5 | 4ba752877779407744016dfe5be9631931f40aaab046b94ef6e460c33a3cd11d | S=C1Cc2ccccc2N1.S=C1Cc2ccccc2N1.S=C1Cc2ccccc2N1 | [C;D1;H3:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[S;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+0:11]:1-[NH2;D1;+0:12].[C;D1;H3:13]-[C:14]-[CH2;D2;+0:15]-[S;H0;D2;+0:16]-[c;H0;D3;+0:17]1:[c:18]:[c:19]:[c:20](-[NH2;D1;+0:21]):[cH;D2;+0:22]:[c:23]:1.[CH3;D1;+0:24]-[S;H0... | null | [] | null | null | null | null | 4-Methylthiooxindole and 6-methylthiooxindole are prepared according to the procedure of U.S. Pat. No. 4,006,161. 7-Methylthio and 7-n-butylthiooxindoles are prepared by using the same procedure starting with 2-methylthioaniline and 2-n-butylthioaniline, respectively. 5-n-Propylthiooxindole is prepared by the same synt... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Primary amine.Monosulfide.Monosulfide.Monosulfide | Thioamide.Thioamide.Thioamide | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccc2c(c1)CCN2.c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2c(c1)CCN2.c1ccc2c(c1)CCN2 | Other | null | null | null | CCCCSc1ccccc1N.CCCSc1ccc(N)cc1.CSc1ccccc1N>>CCCc1ccc2c(c1)CC(=S)N2.Cc1ccc2c(c1)NC(=S)C2.Cc1cccc2c1CC(=S)N2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c0dad1d0d168495ea764fd1fd6e209c1 | CCOC(=O)CC(=O)OCC.O=C(c1ccccc1)c1ccc(Cl)c([N+](=O)[O-])c1>>CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | ClC1=C(C=C(C(=O)C2=CC=CC=C2)C=C1)[N+](=O)[O-].[Na].C(C)O.C(CC(=O)OCC)(=O)OCC>>[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)C(C(=O)OCC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Cl[c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1[N+:26](=[O:27])[O-:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[... | CCOC(=O)CC(=O)OCC.O=C(c1ccccc1)c1ccc(Cl)c([N+](=O)[O-])c1 | CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | null | null | C(Cl)Cl | C-C Coupling | Hurtley reaction | 5a1171068c2a10d196160f01101b1c97354196d6923cfc455c6b686284d6c6f2 | c0fb657475d92a5e1ab643a3f03921ebe4d047c8d805f98b012a5df3f9fb1f6c | O=C(c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[C:9](=[O;D1;H0:10])-[#8:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | 2 | HOUR | To a solution of sodium ethoxide, formed by reacting 4.6 g. (0.2 mole) of sodium metal with 200 ml. of ethanol, at 0° C. was added 32 g. (0.2 mole) of diethyl malonate followed by 26.1 g. (0.1 mole) of 4-chloro-3-nitrobenzophenone. The mixture was allowed to stir at room temperature for 2 hours and was then poured into... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 2 | CCOC(=O)CC(=O)OCC.O=C(c1ccccc1)c1ccc(Cl)c([N+](=O)[O-])c1>C(Cl)Cl>CCOC(=O)C(C(=O)OCC)c1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-92c9585a51c84d6bac68d122a75409e7 | CCOC(=O)Cl.O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>>CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)O.C(C)N(CC)CC.C(C)OC(=O)Cl.COCCOC>>[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)OCC | O=C(Cl)O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[N+:21](=[O:22])[O-:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[N+:21](=[O... | CCOC(=O)Cl.O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] | null | null | C(C)O.[Cl-].[Na+].O.C(C)OCC | Heteroatom Alkylation and Arylation | Ketonization by decarboxylation of acid halides | 206d5ec09ce643b803adbcf860b4078b98a030d6380c33850f0abd3ec7da7984 | 8388f1b1aad516c0093910cf7e0a1fba12f038b873168f29f87df716614f8df9 | O=C(c1ccccc1)c1ccccc1 | Cl-C(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | 94 | [{"value": 94.0, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 5 | MINUTE | To a solution of 13.8 g. (48.4 mmoles) of 2-nitro-4-benzoylphenylacetic acid in 150 ml. of 1,2-dimethoxyethane at 15° C. was added 5.87 g. (58.1 mmole) of triethylamine. After 5 minutes 5.75 g. (53.2 mmoles) of ethylchloroformate was added and the reaction mixture allowed to stir at 10° C. for 15 minutes. Ethanol (15 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether | Ester | null | null | c1ccccc1.c1ccccc1 | HCl | C(C)O.[Cl-].[Na+].O.C(C)OCC | 10 | 0.083333 | CCOC(=O)Cl.O=C(O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-]>C(C)O.[Cl-].[Na+].O.C(C)OCC>CCOC(=O)Cc1ccc(C(=O)c2ccccc2)cc1[N+](=O)[O-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d6c2eca3969d4ba2a9cdbb8916d07d20 | O=C1Cc2c(Cl)cc(C(=O)c3ccccc3)cc2N1.O=C1Cc2ccc(C(=O)c3cccs3)cc2N1>>O=C1Cc2ccc(C(=O)c3ccccc3)cc2N1 | FC1=C2CC(NC2=CC(=C1)C(C1=CC=CS1)=O)=O.COC1=C2CC(NC2=CC(=C1)C(CCC)=O)=O.FC1=C2CC(NC2=CC(=C1)C(C)=O)=O.COC1=C2CC(NC2=CC(=C1)C(C1=CC=CC=C1)=O)=O.C1(=CC=CS1)C(=O)C1=CC=C2CC(NC2=C1)=O.C1=C(C=CS1)C(=O)C1=CC=C2CC(NC2=C1)=O.CSC1=C2CC(NC2=CC(=C1)C(C1=CSC=C1)=O)=O.ClC1=C2CC(NC2=CC(=C1)C(C1=CC=CC=C1)=O)=O.CC1=C2CC(NC2=CC(=C1)C(C1... | O=C1Cc2c(Cl)cc(C(=O)c3ccc[cH:14][cH:15]3)cc2N1.s1[c:10]([C:8]([c:7]2[cH:6][cH:5][c:4]3[c:17]([cH:16]2)[NH:18][C:2](=[O:1])[CH2:3]3)=[O:9])[cH:11][cH:12][cH:13]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][c:17]2[NH:18]1 | O=C1Cc2c(Cl)cc(C(=O)c3ccccc3)cc2N1.O=C1Cc2ccc(C(=O)c3cccs3)cc2N1 | O=C1Cc2ccc(C(=O)c3ccccc3)cc2N1 | null | null | null | Miscellaneous | OtherReaction | b450880ff2b4862bba190acb50f208aa2d2315208774d09403a40c74b6f7d837 | b99847263aa84a8ee29c980928e1cf548cef4019e6c4f5aef7c5ee3f85cfd3d3 | O=C1Cc2ccc(C(=O)c3ccccc3)cc2N1 | Cl-c1:c:c(-C(=O)-c2:[cH;D2;+0:1]:[cH;D2;+0:2]:c:c:c:2):c:c2:c:1-C-C(=O)-N-2.[O;D1;H0:3]=[C:4](-[c:5])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:s:1>>[O;D1;H0:3]=[C:4](-[c:5])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:2]:[cH;D2;+0:1]:1 | null | [] | null | null | null | null | In a similar manner, starting with the appropriate reagent 6-n-butyryloxindole, 4-chloro-6-benzoyloxindole, 4-fluoro-6-acetyloxindole, 4-methoxy-6-benzoyloxindole, 4-methoxy-6-butyryloxindole, 6-(2-thenoyl)oxindole, 6-(3-thenoyl)oxindole, 4-methyl-6-(2-thenoyl)oxindole, 4-methylthio-6-(3-thenoyl)oxindole and 4-fluoro-6... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ketone.Secondary amide | Ketone | c1ccc2c(c1)CCN2.c1ccccc1.c1ccsc1 | c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | HCl | null | null | null | O=C1Cc2c(Cl)cc(C(=O)c3ccccc3)cc2N1.O=C1Cc2ccc(C(=O)c3cccs3)cc2N1>>O=C1Cc2ccc(C(=O)c3ccccc3)cc2N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5795629fb40746d085bc44f1d0c40b6a | CC#N.O.c1ccc2c(c1)CCN2>>CC(=O)c1cccc2c1NCC2 | B(Br)(Br)Br.Cl.C(C)#N.[Cl-].[Al+3].[Cl-].[Cl-].O.N1CCC2=CC=CC=C12>>C(C)(=O)C=1C=CC=C2CCNC12 | N#[C:2][CH3:1].[OH2:3].[cH:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[NH:10][CH2:11][CH2:12]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[NH:10][CH2:11][CH2:12]2 | CC#N.O.c1ccc2c(c1)CCN2 | CC(=O)c1cccc2c1NCC2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 05da27235e89652fc83a66d9d2d5176bc2f28258bebd97e499937d81fc5745d5 | 4ee1f20c4863715b4328c7be13c49a9e284d6de1cecfc1b4e83451c8d717f675 | c1ccc2c(c1)CCN2 | N#[C;H0;D2;+0:1]-[C;D1;H3:2].[C:3]-[#7:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9].[OH2;D0;+0:10]>>[C:3]-[#7:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;H0;D1;+0:10]):[c:8]:[c:9] | null | [] | 5 | CELSIUS | 10 | MINUTE | To a solution of 47.35 g. (0.5 mole) of boron tribromide in 300 ml. of toluene at 0° C. was added dropwise a solution of 50 g. (0.42 mole) of indoline and 22.39 g. (0.546 mole) of acetonitrile in 200 ml. of toluene. After stirring for 10 minutes 67.2 g. (0.5 mole) of aluminum chloride was added in portions. The resulti... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Ketone | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | C1(=CC=CC=C1)C | 5 | 0.166667 | CC#N.O.c1ccc2c(c1)CCN2>C1(=CC=CC=C1)C>CC(=O)c1cccc2c1NCC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-72e6c5070b794368854183d6caa959fa | CC(=O)c1cccc2c1NCC2>>CC(=O)c1cccc2cc[nH]c12 | C(C)(=O)C=1C=CC=C2CCNC12>>C(C)(=O)C=1C=CC=C2C=CNC12 | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:12]1[NH:11][CH2:10][CH2:9]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][nH:11][c:12]12 | CC(=O)c1cccc2c1NCC2 | CC(=O)c1cccc2cc[nH]c12 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4] | C(Cl)Cl | Oxidation | OtherReaction | 2ed5a611e54dbdb6a4872dadd5b156713986794ff33171779f2c247b824bc0a1 | 45f806b8e00071c3429c43b3544e10767c5f82b269d7c53bc7fada9a5eb3b8c6 | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:6](:[c:7])-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[nH;D2;+0:10]:[cH;D2;+0:9]:[cH;D2;+0:8]:[c:6]:1:[c:7] | 76 | [{"value": 76.0, "product": "C(C)(=O)C=1C=CC=C2C=CNC12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To 30 g. (0.186 mole) of 7-acetylindoline in 415 ml. of methylene chloride was added 48.5 g (0.56 mole) of manganese dioxide and the mixture refluxed through a soxhlet filled with 4A molecular sieves for 22 hours. The mixture was cooled and an additional 48.5 g. of manganese dioxide was added. Fresh molecular sieves we... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | null | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)Cl | null | 5 | CC(=O)c1cccc2c1NCC2>[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)Cl>CC(=O)c1cccc2cc[nH]c12 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-62114cd74ab5480d93d8211eeeebf13b | CSc1cc2c(c(C(C)=O)c1)NC(=O)C2>>CC(=O)c1cccc2c1NC(=O)C2 | C(CC)(=O)C=1C=CC=C2CC(NC12)=O.C(C1=CC=CC=C1)(=O)C=1C=CC=C2CC(NC12)=O.C1(=CC=CS1)C(=O)C=1C=CC=C2CC(NC12)=O.C1=C(C=CS1)C(=O)C=1C=CC=C2CC(NC12)=O.CC=1C=C2CC(NC2=C(C1)C(C)=O)=O.CSC=1C=C2CC(NC2=C(C1)C(C)=O)=O.FC=1C=C2CC(NC2=C(C1)C(C1=CC=CC=C1)=O)=O.BrC=1C=C2CC(NC2=C(C1)C(C1=CC=CS1)=O)=O>>C(C)(=O)C=1C=CC=C2CC(NC12)=O | CS[c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:9]2[c:8]([cH:7]1)[CH2:13][C:11](=[O:12])[NH:10]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[NH:10][C:11](=[O:12])[CH2:13]2 | CSc1cc2c(c(C(C)=O)c1)NC(=O)C2 | CC(=O)c1cccc2c1NC(=O)C2 | null | null | null | Reduction | OtherReaction | d730df81388c9d85c77c0667072e73b409dd35ba5b74f30f4a9e8e7bdba1a661 | 32a5269109432865a866e9a2b5da238f4471b13dee7daf193dc4e8c41b091706 | O=C1Cc2ccccc2N1 | C-S-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6]):[c:7]:[c:8]>>[C;D1;H3:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[cH;D2;+0:1]:[c:7]:[c:8] | null | [] | null | null | null | null | Starting with the appropriate reagents and following the procedure of Preparation K, 7-propionyloxindole, 7-benzoyloxindole, 7-(2-thenoyl)oxindole, 7-(3-thenoyl)oxindole, 5-methyl-7-acetyloxindole, 5-methylthio-7-acetyloxindole, 5-fluoro-7-benzoyloxindole and 5-bromo-7-(2-thenoyl)oxindole are prepared.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | null | null | null | CSc1cc2c(c(C(C)=O)c1)NC(=O)C2>>CC(=O)c1cccc2c1NC(=O)C2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6162f81a014e484d9b8d5eb5cdb0fc03 | Cc1cc(C(=O)c2ccccc2)cc2c1NC(=O)C2.O=C1Cc2cc(C(=O)c3ccsc3)ccc2N1>>O=C1Cc2cc(C(=O)c3ccccc3)ccc2N1 | C(C)(=O)C=1C=C2CC(NC2=CC1)=O.CC1=C2CC(NC2=CC=C1C(C)=O)=O.C1(=CC=CS1)C(=O)C=1C=C2CC(NC2=CC1)=O.C1=C(C=CS1)C(=O)C=1C=C2CC(NC2=CC1)=O.ClC1=C2CC(NC2=CC=C1C(C)=O)=O.CC=1C=C(C=C2CC(NC12)=O)C(C1=CC=CC=C1)=O.C(CC)(=O)C=1C=C2CC(NC2=CC1)=O>>C(C1=CC=CC=C1)(=O)C=1C=C2CC(NC2=CC1)=O | Cc1c[c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:5][c:4]2[c:17]1[NH:18][C:2](=[O:1])[CH2:3]2.O=C1Cc2cc(C(=O)c3ccsc3)[cH:15][cH:16]c2N1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[cH:15][cH:16][c:17]2[NH:18]1 | Cc1cc(C(=O)c2ccccc2)cc2c1NC(=O)C2.O=C1Cc2cc(C(=O)c3ccsc3)ccc2N1 | O=C1Cc2cc(C(=O)c3ccccc3)ccc2N1 | null | null | null | Miscellaneous | OtherReaction | 68f0df1de30bfd22cb32ca4d8d801675e44a02891b26c7502e11381199a37536 | 5b388534c7ab75644fe3aa2eae51d8d192360a553d2464346e04a8928be3e844 | O=C1Cc2cc(C(=O)c3ccccc3)ccc2N1 | C-c1:c:[c;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[c:4]):[c:5]:[c:6]2:[c;H0;D3;+0:7]:1-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]-2.O=C1-C-c2:c:c(-C(=O)-c3:c:c:s:c:3):[cH;D2;+0:12]:[cH;D2;+0:13]:c:2-N-1>>[O;D1;H0:10]=[C:9]1-[#7:8]-[c;H0;D3;+0:7]2:[cH;D2;+0:13]:[cH;D2;+0:12]:[c;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[c:4]):[c:5]:[c:6]:2-[C:... | null | [] | null | null | null | null | Using a similar procedure and starting with the requisite reagents, 5-acetyloxindole, 5-propionyloxindole, 5-(2-thenoyl)oxindole, 5-(3-thenoyl)oxindole, 4-methyl-5-acetyloxindole, 4-chloro-5-acetyloxindole and 7-methyl-5-benzoyloxindole are prepared.
Conditions: See reaction.notes.procedure_details.
Workup: are prepare... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Secondary amide | Ketone | c1ccc2c(c1)CCN2.c1ccc2c(c1)CCN2.c1ccsc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1 | Other | null | null | null | Cc1cc(C(=O)c2ccccc2)cc2c1NC(=O)C2.O=C1Cc2cc(C(=O)c3ccsc3)ccc2N1>>O=C1Cc2cc(C(=O)c3ccccc3)ccc2N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3ed5c8b0016f4432bfed93da605fb3ce | O=C1Cc2ccc3c(c2N1)OCO3>>c1cc2cc3c(cc2[nH]1)OCO3 | C1OC2=C3CC(NC3=CC=C2O1)=O.C1OC2=CC=C3CC(NC3=C2O1)=O.C1OC=2C=C3CC(NC3=CC2O1)=O.[N+](=O)([O-])C1=C(C=C2C(=C1)OCO2)CC(=O)OC.[N+](=O)([O-])C1OC2=C(C=CC=C2O1)CC(=O)OC>>C1OC=2C=C3C=CNC3=CC2O1 | O=[C:1]1[CH2:2][c:3]2[cH:4][cH:5][c:6]3[c:7]([c:8]2[NH:9]1)[O:12][CH2:11][O:10]3>>[cH:1]1[cH:2][c:3]2[cH:4][c:5]3[c:6]([cH:7][c:8]2[nH:9]1)[O:10][CH2:11][O:12]3 | O=C1Cc2ccc3c(c2N1)OCO3 | c1cc2cc3c(cc2[nH]1)OCO3 | null | null | null | Miscellaneous | OtherReaction | 6634bf7734f230901309fa4f1521432488ab3987b53bd5428876f9d5c6eb6423 | 57d17b7f635fad717ee8ab10e86ef20b1bbadd42835b29ebc439bf55e4b83276 | c1cc2cc3c(cc2[nH]1)OCO3 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[c:3]2:[c:4]:[cH;D2;+0:5]:[c:6]3:[c;H0;D3;+0:7](:[c:8]:2-[NH;D2;+0:9]-1)-[O;H0;D2;+0:10]-[C:11]-[#8:12]-3>>[#8:12]1-[C:11]-[O;H0;D2;+0:10]-[c;H0;D3;+0:5]2:[c:4]:[c:3]3:[cH;D2;+0:2]:[cH;D2;+0:1]:[nH;D2;+0:9]:[c:8]:3:[cH;D2;+0:7]:[c:6]:2-1 | null | [] | null | null | null | null | 5,6-Methylenedioxyoxindole can be prepared via the reduction of methyl 2-nitro-4,5-methylenedioxyphenylacetate according to the procedure of McEvoy et al., J. Org. Chem., 38, 3350 (1973). By a similar procedure, starting with the appropriate methyl 2-nitromethylenedioxyphenylacetate, 4,5-methylenedioxyoxindole and 6,7-... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | Ether | c1cc2c(c3c1CCN3)OCO2 | c1cc2cc3c(cc2[nH]1)OCO3 | c1cc2cc3c(cc2[nH]1)OCO3 | Other | null | null | null | O=C1Cc2ccc3c(c2N1)OCO3>>c1cc2cc3c(cc2[nH]1)OCO3 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2dd8beb060374261b699a38de66f5256 | CC(C)N=C=O.O=C1Cc2ccccc2N1>>CC(C)NC(=O)N1C(=O)Cc2ccccc21 | N1C(CC2=CC=CC=C12)=O.C(C)(C)N=C=O>>C(C)(C)NC(=O)N1C(CC2=CC=CC=C12)=O | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].[NH:7]1[C:8](=[O:9])[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[N:7]1[C:8](=[O:9])[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | CC(C)N=C=O.O=C1Cc2ccccc2N1 | CC(C)NC(=O)N1C(=O)Cc2ccccc21 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and secondary amine | 29dd27c87e6f9801dcadea6821ce358d8a4f985bbfdea32deebaa8f964d87302 | d8031df9745ffb9494a0da2553ed47ba21f8143926e9537ff85149a4ef4cadb4 | O=C1Cc2ccccc2N1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[O;D1;H0:7]=[C:8]1-[C:9]-[c:10]:[c:11](:[c:12])-[NH;D2;+0:13]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:13]1-[C:8](=[O;D1;H0:7])-[C:9]-[c:10]:[c:11]-1:[c:12] | null | [] | null | null | 8 | HOUR | To a stirred suspension of 5.0 g. (37.6 mmole) of 2-oxindole in 50 ml. of toluene was added 8.0 g. (94.0 mmole) of isopropyl isocyanate, and the mixture was heated under reflux for 6 hours. The reaction mixture was allowed to cool and then it was stirred at room temperature overnight. The solvent was removed by evapora... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amide | Urea | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | null | C1(=CC=CC=C1)C | null | 8 | CC(C)N=C=O.O=C1Cc2ccccc2N1>C1(=CC=CC=C1)C>CC(C)NC(=O)N1C(=O)Cc2ccccc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bbeceddc0faf432ab9c414f3a0a0c3be | COC(=O)C1C(=O)Nc2ccc(Cl)cc21.O=C=Nc1ccccc1>>COC(=O)C1C(=O)N(C(=O)Nc2ccccc2)c2ccc(Cl)cc21 | ClC=1C=C2C(C(NC2=CC1)=O)C(=O)OC.C1(=CC=CC=C1)N=C=O>>C1(=CC=CC=C1)NC(=O)N1C(C(C2=CC(=CC=C12)Cl)C(=O)OC)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[C:6](=[O:7])[NH:8][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]21.[C:9](=[O:10])=[N:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[C:6](=[O:7])[N:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21]([Cl:22]... | COC(=O)C1C(=O)Nc2ccc(Cl)cc21.O=C=Nc1ccccc1 | COC(=O)C1C(=O)N(C(=O)Nc2ccccc2)c2ccc(Cl)cc21 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and secondary amine | 29dd27c87e6f9801dcadea6821ce358d8a4f985bbfdea32deebaa8f964d87302 | d8031df9745ffb9494a0da2553ed47ba21f8143926e9537ff85149a4ef4cadb4 | O=C1Cc2ccccc2N1C(=O)Nc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[c:5]:[c:6](:[c:7])-[NH;D2;+0:8]-[C:9]-1=[O;D1;H0:10].[O;D1;H0:11]=[C;H0;D2;+0:12]=[N;H0;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[c:5]:[c:6](:[c:7])-[N;H0;D3;+0:8](-[C;H0;D3;+0:12](=[O;D1;H0:11])-[NH;D2;+0:13]-[c:14](:[c:15]):[c:16])-[C:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | To 6.0 g. (0.027 mole) of methyl 5-chlorooxindole-3-carboxylate in 200 ml. of toluene was added 5.25 ml. (0.048 mole) of phenylisocyanate and the resulting reaction mixture heated to reflux overnight. The reaction mixture was cooled and diluted with petroleum ether to give, after filtration and drying, 2.0 g. of the de... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amide | Urea | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | null | C1(=CC=CC=C1)C | null | null | COC(=O)C1C(=O)Nc2ccc(Cl)cc21.O=C=Nc1ccccc1>C1(=CC=CC=C1)C>COC(=O)C1C(=O)N(C(=O)Nc2ccccc2)c2ccc(Cl)cc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dacd69f7df84455997655f6c3f309e42 | O=Cc1ccccc1>>O=Cc1ccccc1 | C(C1=CC=CC=C1)=O.C(C=CC1=CC=CC=C1)=O>>C(C1=CC=CC=C1)=O.C(C=CC1=CC=CC=C1)=O | [O:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | O=Cc1ccccc1 | O=Cc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | FIG. 2 is the GC-IR spectrum for the bottoms in the distillation pot. The peak indicated by reference numeral 20 is the peak for benzaldehyde. The peak indicated by reference numeral 21 is the peak for the cinnamaldehyde.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | null | null | null | O=Cc1ccccc1>>O=Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a5f8cf3706fb4e88af4fdf400f66f3e5 | CCCc1cnc2c(c1)C(=O)N(C(C)(C(N)=O)C(C)C)C2=O>>CCCc1cnc2c(c1)C(=O)N1C2=NC(=O)C1(C)C(C)C | [OH-].[Na+].C(CC)C=1C=C2C(=NC1)C(N(C2=O)C(C(=O)N)(C)C(C)C)=O.O>>C(C)(C)C1(C(N=C2N1C(C=1C2=NC=C(C1)CCC)=O)=O)C | O=[C:13]1[c:7]2[n:6][cH:5][c:4]([CH2:3][CH2:2][CH3:1])[cH:9][c:8]2[C:10](=[O:11])[N:12]1[C:17]([C:15]([NH2:14])=[O:16])([CH3:18])[CH:19]([CH3:20])[CH3:21]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][n:6][c:7]2[c:8]([cH:9]1)[C:10](=[O:11])[N:12]1[C:13]2=[N:14][C:15](=[O:16])[C:17]1([CH3:18])[CH:19]([CH3:20])[CH3:21] | CCCc1cnc2c(c1)C(=O)N(C(C)(C(N)=O)C(C)C)C2=O | CCCc1cnc2c(c1)C(=O)N1C2=NC(=O)C1(C)C(C)C | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 852876acc5fdf94c26885bc136e0813562d82bf37ea8cb48c3ec1f45894b34a9 | cbb7764ac83f445d6d83811eb9820561db36f218c9f02320a912cef153626521 | O=C1CN2C(=O)c3cccnc3C2=N1 | O=[C;H0;D3;+0:1]1-[#7:2](-[C:3]-[C:4](-[NH2;D1;+0:5])=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1:[#7;a:11]:[c:12]>>[O;D1;H0:8]=[C:7]1-[c:9]:[c:10](:[#7;a:11]:[c:12])-[C;H0;D3;+0:1]2=[N;H0;D2;+0:5]-[C:4](=[O;D1;H0:6])-[C:3]-[#7:2]-1-2 | null | [] | null | null | null | null | With the simultaneous addition of 0.5 g of powdered sodium hydroxide, a solution of α-[3-n-propyl-6H-pyrrolo[3,4-b]pyridine-5,7-dione-6-yl]-α-isopropyl-α-methyl-acetamide (m.p.: 82° C.) in 100 ml of toluene is heated under reflux for 2 hours in a water separator. After the reaction solution has cooled, it is filtered t... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide.Primary amide | null | c1cnc2c(c1)C[NH]C2 | c1cnc2c(c1)CN1CCN=C21 | c1cnc2c(c1)CN1CCN=C21 | HO- | C1(=CC=CC=C1)C | null | null | CCCc1cnc2c(c1)C(=O)N(C(C)(C(N)=O)C(C)C)C2=O>C1(=CC=CC=C1)C>CCCc1cnc2c(c1)C(=O)N1C2=NC(=O)C1(C)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7aa85cf980dc49f198b0ddfbeab452f7 | CC(C)CCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CC(C)CCCCCCCCCCCCC(=O)Cl | C(CCCCCCCCCCCCC(C)C)(=O)O.S(=O)(Cl)Cl>>C(CCCCCCCCCCCCC(C)C)(=O)Cl | O[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])=[O:17].O=S(Cl)[Cl:18]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[Cl:18] | CC(C)CCCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CC(C)CCCCCCCCCCCCC(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | Isohexadecanoic acid (20 g, 0.078 mol) and thionyl chloride (7.2 ml, 0.0984 mol) were refluxed together gently for 1 hour to produce isohexadecanoyl chloride and the reaction was monitored by infra-red spectroscopy. Excess thionyl chloride was distilled away under rotary pump vacuum at reflux temperature. The acyl chlo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | null | null | null | CC(C)CCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CC(C)CCCCCCCCCCCCC(=O)Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-580394b4ef7a438bb6f3a79f841eee23 | COC(=O)C(C)Br.NS(=O)(=O)c1ccccc1O>>COC(=O)C(C)Oc1ccccc1S(N)(=O)=O | OC1=C(C=CC=C1)S(=O)(=O)N.C([O-])([O-])=O.[K+].[K+].BrC(C(=O)OC)C>>COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N | Br[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14]([NH2:15])(=[O:16])=[O:17]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14]([NH2:15])(=[O:16])=[O:17] | COC(=O)C(C)Br.NS(=O)(=O)c1ccccc1O | COC(=O)C(C)Oc1ccccc1S(N)(=O)=O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a60236748d2543bdb97e5465447a595cd9bb5fef4e3fe96ed6af652af51cd157 | 94a54f0a6e629a85ca32b8fd3cf243ab64283e31ecfe8705ffe0df2304c488b4 | c1ccccc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 80.7 | [{"value": 80.7, "product": "COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 34.6 g of 2-hydroxybenzenesulfonamide and 55.3 g of potassium carbonate are added to 800 ml of acetonitrile. With efficient stirring, 33.4 g of methyl 2-bromopropionate are added dropwise over 10 minutes and the suspension is then heated for 5 hours to 45° C. After the reaction mixture has cooled, the precipitated salt... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | null | COC(=O)C(C)Br.NS(=O)(=O)c1ccccc1O>C(C)#N>COC(=O)C(C)Oc1ccccc1S(N)(=O)=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-256cd9153e88410d975da315b2913afe | CCCCN=C=O.COC(=O)C(C)Oc1ccccc1S(N)(=O)=O>>COC(=O)C(C)Oc1ccccc1S(=O)(=O)N=C=O | C(=O)(Cl)Cl.COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N.C(CCC)N=C=O.C(=O)(Cl)Cl>>COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N=C=O | CCCCN=[C:18]=[O:19].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14](=[O:15])(=[O:16])[NH2:17]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14](=[O:15])(=[O:16])[N:17]=[C:18]=[O:19] | CCCCN=C=O.COC(=O)C(C)Oc1ccccc1S(N)(=O)=O | COC(=O)C(C)Oc1ccccc1S(=O)(=O)N=C=O | null | N1(NCCCCCC1)C1CCCCCCC1 | C=1(C(=CC=CC1)C)C | Functional Group Interconversion | OtherReaction | d6c69f89b87c5c421a628563544ee2b8b0164ec4561bcd29a2cbba0dce4075ac | 5df9e857f75ada60baf9e936007533a18389016451154bd1ed26e91b5babd844 | c1ccccc1 | C-C-C-C-N=[C;H0;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7]>>[O;D1;H0:5]=[#16:4](=[O;D1;H0:6])(-[c:7])-[N;H0;D2;+0:3]=[C;H0;D2;+0:1]=[O;D1;H0:2] | 125.5 | [{"value": 125.5, "product": "COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N=C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 12.9 g of 2-(1-methoxycarbonylethoxy)-benzenesulfonamide, 4.9 g of n-butylisocyanate and 0.1 g of diazabicyclooctane and 130 ml of xylene is refluxed for 30 minutes. Then 10 g of phosgene are passed into the solution at the same temperature over 90 minutes. Excess phosgene is expelled with nitrogen and the... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | null | null | null | c1ccccc1 | Other | N1(NCCCCCC1)C1CCCCCCC1.C=1(C(=CC=CC1)C)C | null | null | CCCCN=C=O.COC(=O)C(C)Oc1ccccc1S(N)(=O)=O>N1(NCCCCCC1)C1CCCCCCC1.C=1(C(=CC=CC1)C)C>COC(=O)C(C)Oc1ccccc1S(=O)(=O)N=C=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a8b5e717444b4d86bbebb7c007f0d53f | C=CCOc1ccccc1S(N)(=O)=O.O=C(OO)c1cccc(Cl)c1>>NS(=O)(=O)c1ccccc1OCC1CO1 | ClC1=CC(=CC=C1)C(=O)OO.C(C=C)OC1=C(C=CC=C1)S(=O)(=O)N>>O1C(C1)COC1=C(C=CC=C1)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]=[CH2:14].O=C(O[OH:15])c1cccc(Cl)c1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]1[CH2:14][O:15]1 | C=CCOc1ccccc1S(N)(=O)=O.O=C(OO)c1cccc(Cl)c1 | NS(=O)(=O)c1ccccc1OCC1CO1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | fa67e488c6e215faf3f8ba92b55089cf5ac738315c63f0805edf5ac603aa4c40 | 8f36f0953871bb4e46b1272823a9df5d866ec11318b28272136c57016b5bffba | c1ccc(OCC2CO2)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#8:2]-[C:3]-[CH;D2;+0:4]=[CH2;D1;+0:5]>>[#8:2]-[C:3]-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-1 | 78 | [{"value": 78.0, "product": "O1C(C1)COC1=C(C=CC=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 15.3 g of 3-chloroperbenzoic acid in 270 ml of absolute methylene chloride are added 14.2 g of 2-allyloxyphenylsulfonamide over 2 minutes. The solution is then heated to reflux for 3 hours, cooled, and then washed three times with saturated sodium carbonate solution and once with water. The organic phas... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Allyl | Ether | c1ccccc1 | C1CO1 | c1ccccc1.C1CO1 | HCl | C(Cl)Cl | null | null | C=CCOc1ccccc1S(N)(=O)=O.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>NS(=O)(=O)c1ccccc1OCC1CO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-983466e81fae4be2b37209716d2579ca | CC(=O)COc1ccccc1S(N)(=O)=O.OCCO>>CC1(COc2ccccc2S(N)(=O)=O)OCCO1 | C(C(C)=O)OC1=C(C=CC=C1)S(=O)(=O)N.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=CC=C1)C>>CC1(OCCO1)COC1=C(C=CC=C1)S(=O)(=O)N | [CH3:1][C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11]([NH2:12])(=[O:13])=[O:14])=[O:15].O[CH2:16][CH2:17][OH:18]>>[CH3:1][C:2]1([CH2:3][O:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[S:11]([NH2:12])(=[O:13])=[O:14])[O:15][CH2:16][CH2:17][O:18]1 | CC(=O)COc1ccccc1S(N)(=O)=O.OCCO | CC1(COc2ccccc2S(N)(=O)=O)OCCO1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 2baa95c632045e217509d8ec12cda8674252268fe3f8cb44eb2e5ebe0f27c30f | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | c1ccc(OCC2OCCO2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[#8:4]-[C:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8]>>[#8:4]-[C:5]-[C;H0;D4;+0:6]1(-[C;D1;H3:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1 | null | [] | null | null | null | null | A mixture of 4.58 g of 2-(2-propanon-1-yloxy)phenylsulfonamide, 2 ml of ethylene glycol, 0.02 g of p-toluenesulfonic acid and 30 ml of toluene is heated for 7 hours to reflux while simultaneously separating the water of reaction. The cooled solution is taken up in 80 ml of ethyl acetate and the organic phase is washed ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccccc1.C1COCO1 | HO- | C(C)(=O)OCC | null | null | CC(=O)COc1ccccc1S(N)(=O)=O.OCCO>C(C)(=O)OCC>CC1(COc2ccccc2S(N)(=O)=O)OCCO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f338593bb42141e5a94468c5d011ca54 | CCCCCC(CO)C(C)O.N#Cc1ccc(C=O)cc1>>CCCCCC1COC(c2ccc(C#N)cc2)OC1C | C(#N)C1=CC=C(C=O)C=C1.OCC(C(C)O)CCCCC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(#N)C1=CC=C(C=C1)C1OCC(C(O1)C)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][OH:8])[CH:19]([OH:18])[CH3:20].O=[CH:9][c:10]1[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][O:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]2)[O:18][CH:19]1[CH3:20] | CCCCCC(CO)C(C)O.N#Cc1ccc(C=O)cc1 | CCCCCC1COC(c2ccc(C#N)cc2)OC1C | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 078119554865b648a6facdc6248b78db5e4dc0f883a88231fb077723ffc0df4e | 232b156bc2ce8ae2305afd0f173afafd4724b8e3a40743bae5e711a1772e739c | c1ccc(C2OCCCO2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](-[OH;D1;+0:7])-[C:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:5]-[C:6]1-[C:8]-[C:9]-[O;H0;D2;+0:10]-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[O;H0;D2;+0:7]-1 | null | [] | null | null | null | null | A mixture of 0.1 mol of p-cyanobenzaldehyde, 0.1 mol of 3-hydroxymethyl-2-octanol, 200 ml of benzene and 150 mg of p-toluenesulfonic acid is boiled under a water separator until the reaction is complete. Usual working-up gives 2-p-cyanophenyl-5-n-pentyl-4-methyl-1,3-dioxane.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Secondary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | null | CCCCCC(CO)C(C)O.N#Cc1ccc(C=O)cc1>C1=CC=CC=C1>CCCCCC1COC(c2ccc(C#N)cc2)OC1C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-42d1b3eddfb84c7aa01824183c097731 | N#CN.O=C(Cl)c1ccccc1>>N#CNC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)Cl.N#CN.[Na]>>C(C1=CC=CC=C1)(=O)NC#N | [N:1]#[C:2][NH2:3].Cl[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[N:1]#[C:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | N#CN.O=C(Cl)c1ccccc1 | N#CNC(=O)c1ccccc1 | null | null | CCOCC.C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 6b8795ab649e99ec7e765cbd407ce37a0b3638ad96cc9e672bdd7bec29c34cf9 | bb28f60d9d2ec09482b204d99571e49e964dfcf84ef33afba181651521212242 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H0:6]#[C:7]-[NH2;D1;+0:8]>>[N;D1;H0:6]#[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 89.7 | [{"value": 89.7, "product": "C(C1=CC=CC=C1)(=O)NC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.6, "product": "C(C1=CC=CC=C1)(=O)NC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzoylcyanamide was prepared by the addition of benzoyl chloride (6.33 g, 0.045 mol) in 100 ml of diethyl ether to a suspension of monosodium cyanamide (5.76 g, 0.090 mol) in 100 ml of ether at 4° C. The reaction was stirred overnight at room temperature and the pale yellow solid which formed was collected and dissolv... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Cyanamide | Cyanamide.Secondary amide | null | null | c1ccccc1 | HCl | CCOCC.C(C)OCC | null | 8 | N#CN.O=C(Cl)c1ccccc1>CCOCC.C(C)OCC>N#CNC(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8d2f5af8638c4353be74f64ba58b6a7f | N#CN.O=C(Cl)C12CC3CC(CC(C3)C1)C2>>N#CNC(=O)C12CC3CC(CC(C3)C1)C2 | C12(CC3CC(CC(C1)C3)C2)C(=O)Cl.N#CN.[Na]>>C12(CC3CC(CC(C1)C3)C2)C(=O)NC#N | [N:1]#[C:2][NH2:3].Cl[C:4](=[O:5])[C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:14]1)[CH2:15]2>>[N:1]#[C:2][NH:3][C:4](=[O:5])[C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:14]1)[CH2:15]2 | N#CN.O=C(Cl)C12CC3CC(CC(C3)C1)C2 | N#CNC(=O)C12CC3CC(CC(C3)C1)C2 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 6b8795ab649e99ec7e765cbd407ce37a0b3638ad96cc9e672bdd7bec29c34cf9 | bb28f60d9d2ec09482b204d99571e49e964dfcf84ef33afba181651521212242 | C1C2CC3CC1CC(C2)C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[N;D1;H0:7]#[C:8]-[NH2;D1;+0:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]#[N;D1;H0:7])(-[C:5])-[C:6] | 85.2 | [{"value": 85.2, "product": "C12(CC3CC(CC(C1)C3)C2)C(=O)NC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 1-Adamantanecarbonyl chloride (1.99 g, 0.010 mol) in 50 ml of THF was added drop-wise to a suspension of sodium cyanamide (1.92 g, 0.030 mol) in 100 ml of THF with stirring at ice bath temperature. The reaction was allowed to proceed at 25° C. for 15 hours. The reaction mixture was then extracted with ethyl acetate (10... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Cyanamide | Cyanamide.Secondary amide | null | null | C1C2CC3CC1CC(C2)C3 | HCl | C1CCOC1 | null | 15 | N#CN.O=C(Cl)C12CC3CC(CC(C3)C1)C2>C1CCOC1>N#CNC(=O)C12CC3CC(CC(C3)C1)C2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3d74b36b043e477a96a43e1e42ccd381 | CCCCCCCCCCCCCCCC(=O)Cl.N#CN>>CCCCCCCCCCCCCCCC(=O)NC#N | Cl.C(CCCCCCCCCCCCCCC)(=O)Cl.C1CCOC1.N#CN.[Na]>>C(CCCCCCCCCCCCCCC)(=O)NC#N | Cl[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].[NH2:18][C:19]#[N:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[NH:18][C:19]#[N:20] | CCCCCCCCCCCCCCCC(=O)Cl.N#CN | CCCCCCCCCCCCCCCC(=O)NC#N | null | null | O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 6b8795ab649e99ec7e765cbd407ce37a0b3638ad96cc9e672bdd7bec29c34cf9 | bb28f60d9d2ec09482b204d99571e49e964dfcf84ef33afba181651521212242 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[N;D1;H0:5]#[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]#[N;D1;H0:5] | 96.3 | [{"value": 96.3, "product": "C(CCCCCCCCCCCCCCC)(=O)NC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 43 | HOUR | A solution of palmitoyl chloride (5.5 g, 0.020 mol) in 50 ml of freshly distilled dry THF was added drop-wise to a suspension of sodium cyanamide (3.84 g. 0.060 mol) in 150 ml of freshly distilled dry THF at ice bath temperature. After the addition, the ice bath was removed and the reaction was allowed to proceed at 25... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Cyanamide | Cyanamide.Secondary amide | null | null | null | HCl | O | null | 43 | CCCCCCCCCCCCCCCC(=O)Cl.N#CN>O>CCCCCCCCCCCCCCCC(=O)NC#N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dc25777ecaf7489698498252fb79841d | CCCCCCCCCCCCCCCCCC(=O)Cl.N#CN>>CCCCCCCCCCCCCCCCCC(=O)NC#N | C(CCCCCCCCCCCCCCCCC)(=O)Cl.N#CN.[Na].C>>C(CCCCCCCCCCCCCCCCC)(=O)NC#N | Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[NH2:20][C:21]#[N:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[NH:20][C:... | CCCCCCCCCCCCCCCCCC(=O)Cl.N#CN | CCCCCCCCCCCCCCCCCC(=O)NC#N | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 6b8795ab649e99ec7e765cbd407ce37a0b3638ad96cc9e672bdd7bec29c34cf9 | bb28f60d9d2ec09482b204d99571e49e964dfcf84ef33afba181651521212242 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[N;D1;H0:5]#[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]#[N;D1;H0:5] | 92.4 | [{"value": 92.4, "product": "C(CCCCCCCCCCCCCCCCC)(=O)NC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 63 | HOUR | Stearoyl chloride (3.03 g, 0.010 mol) in 50 ml of freshly distilled dry THF was added drop-wise to a suspension of sodium cyanamide (1.92 g, 0.030 mol) in 100 ml of freshly distilled dry THF with vigorous stirring. The reaction was allowed to proceed at 25° C for 63 hours. The solids which formed were collected by filt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Cyanamide | Cyanamide.Secondary amide | null | null | null | HCl | C1CCOC1 | null | 63 | CCCCCCCCCCCCCCCCCC(=O)Cl.N#CN>C1CCOC1>CCCCCCCCCCCCCCCCCC(=O)NC#N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-67ec1dc910434204b9a74a71f75eb5df | N#CN.O=C(O)CNC(=O)c1ccccc1>>N#CNC(=O)CNC(=O)c1ccccc1 | N#CN.[Na].C(CNC(=O)C1=CC=CC=C1)(=O)O.C1CCC(CC1)N=C=NC2CCCCC2.ON1C(CCC1=O)=O>>C(C1=CC=CC=C1)(=O)NCC(=O)NC#N | [N:1]#[C:2][NH2:3].O[C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[N:1]#[C:2][NH:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | N#CN.O=C(O)CNC(=O)c1ccccc1 | N#CNC(=O)CNC(=O)c1ccccc1 | null | null | C(C)#N.O.CCOC(=O)C.CC(=O)O | Acylation | Carboxylic acid with primary amine to amide | 1f865723370f71cf1ab7dc00831ab704a96a4326ef6e35f073cf7a866be1f70c | 2e26a213e8110c6a5818ffd27f6c5189453b5abca653629394958b094b8ce114 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[N;D1;H0:7]#[C:8]-[NH2;D1;+0:9]>>[N;D1;H0:7]#[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6] | 56.1 | [{"value": 56.1, "product": "C(C1=CC=CC=C1)(=O)NCC(=O)NC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Hippuric acid (3.58 g, 0.020 mol), DCC (4.13 g, 0.020 mol), and N-hydroxysuccinimide (2.3 g, 0.020 mol) were stirred in 100 ml of acetonitrile at ice bath temperature for 2 hours. The reaction mixture was filtered to remove the bulk of by-product DCU. The filtrate was evaporated in vacuo to dryness, the residue was red... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Cyanamide | Cyanamide.Secondary amide | null | null | c1ccccc1 | HO- | C(C)#N.O.CCOC(=O)C.CC(=O)O | null | 8 | N#CN.O=C(O)CNC(=O)c1ccccc1>C(C)#N.O.CCOC(=O)C.CC(=O)O>N#CNC(=O)CNC(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5d935ab7acac4024b0d5a2228ef4a134 | CC(C)C[C@H](N)C(=O)O.O=C(Cl)c1ccccc1>>CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)O | C(C1=CC=CC=C1)(=O)Cl.[OH-].[Na+].N[C@@H](CC(C)C)C(=O)O>>C(C1=CC=CC=C1)(=O)N[C@@H](CC(C)C)C(=O)O | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH2:6])[C:15](=[O:16])[OH:17].Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[OH:17] | CC(C)C[C@H](N)C(=O)O.O=C(Cl)c1ccccc1 | CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)O | null | null | O | 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:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | null | null | null | null | Benzoyl chloride (4.22 g, 0.030 mol) and 10% NaOH (12 ml, 0.030 mol) were added separately with vigorous stirring to a solution of L-leucine (3.94 g, 0.030 mol) in 150 ml of distilled water at ice bath temperature. The reaction was allowed to proceed at this temperature until the reaction mixture became clear (30 minut... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | O | null | null | CC(C)C[C@H](N)C(=O)O.O=C(Cl)c1ccccc1>O>CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fa8fe89a9b5d4711ac8986f8cc6d799b | CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)O.N#CN>>CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)NC#N | N#CN.[Na].C1CCC(CC1)N=C=NC2CCCCC2.ON1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)N[C@@H](CC(C)C)C(=O)O>>C(C1=CC=CC=C1)(=O)N[C@@H](CC(C)C)C(=O)NC#N | O[C:15]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)=[O:16].[NH2:17][C:18]#[N:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[NH:17][C:18]#[N:19] | CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)O.N#CN | CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)NC#N | null | null | C(C)#N.C1CCOC1.O | Acylation | Carboxylic acid with primary amine to amide | 1f865723370f71cf1ab7dc00831ab704a96a4326ef6e35f073cf7a866be1f70c | 2e26a213e8110c6a5818ffd27f6c5189453b5abca653629394958b094b8ce114 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[N;D1;H0:8]#[C:9]-[NH2;D1;+0:10]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]#[N;D1;H0:8] | 42.9 | [{"value": 42.9, "product": "C(C1=CC=CC=C1)(=O)N[C@@H](CC(C)C)C(=O)NC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | DCC (2.41 g, 0.0117 mol) and N-hydroxysuccinimide (1.35 g, 0.0117 mol) were added to a solution of N-benzoyl-L-leucine (2.75 g, 0.0117 mol) in 100 ml of acetonitrile at ice bath temperature. The reaction was allowed to proceed at this temperature for 2 hours. The reaction mixture was filtered to remove the bulk of the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Cyanamide | Cyanamide.Secondary amide | null | null | c1ccccc1 | HO- | C(C)#N.C1CCOC1.O | null | 2 | CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)O.N#CN>C(C)#N.C1CCOC1.O>CC(C)C[C@H](NC(=O)c1ccccc1)C(=O)NC#N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c4b5968c16f543fc8c35e4b753328296 | COC(=O)[C@@H](N)Cc1ccccc1.O=C1CC[C@@H](C(=O)O)N1>>COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCC(=O)N1 | Cl.COC([C@@H](N)CC1=CC=CC=C1)=O.CN1CCOCC1.CN1CCOCC1.ClC(=O)OCC(C)C.N1[C@@H](CCC1=O)C(=O)O>>COC([C@@H](NC([C@H]1NC(CC1)=O)=O)CC1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[NH2:13].O[C:14](=[O:15])[C@@H:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[NH:13][C:14](=[O:15])[C@@H:16]1[CH2:17][CH2:18][C:19](=[O:20])[NH:21]1 | COC(=O)[C@@H](N)Cc1ccccc1.O=C1CC[C@@H](C(=O)O)N1 | COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCC(=O)N1 | null | null | CN(C)C=O.C1CCOC1.CN(C)C=O.CCOC(=O)C.CC(=O)O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CC[C@@H](C(=O)NCCc2ccccc2)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9](-[C:8])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | 2 | MINUTE | N-Methylmorpholine (2.02 g, 0.020 mol) and isobutyl chloroformate (2.73 g, 0.020 mol) were added to a solution of L-pyroglutamic acid (2.58 g, 0.020 mol) in 100 ml of THF/DMF (6:1) at -15° C. After a 2 minute coupling period, a mixture of L-phenylalanine methyl ester hydrochloride (4.31 g, 0.020 mol) (suspension) and N... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCNC1 | HO- | CN(C)C=O.C1CCOC1.CN(C)C=O.CCOC(=O)C.CC(=O)O | null | 0.033333 | COC(=O)[C@@H](N)Cc1ccccc1.O=C1CC[C@@H](C(=O)O)N1>CN(C)C=O.C1CCOC1.CN(C)C=O.CCOC(=O)C.CC(=O)O>COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCC(=O)N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-590ba5be6eb243c4a69123ef9edf892d | N#CN.O=C1CC[C@@H](C(=O)N[C@@H](Cc2ccccc2)C(=O)O)N1>>N#CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCC(=O)N1 | Cl.N#CN.[Na].N1[C@@H](CCC1=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O.[Cl-].[Na+].C1CCC(CC1)N=C=NC2CCCCC2.ON1C(CCC1=O)=O>>N1[C@@H](CCC1=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NC#N | [N:1]#[C:2][NH2:3].O[C:4](=[O:5])[C@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[NH:14][C:15](=[O:16])[C@@H:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22]1>>[N:1]#[C:2][NH:3][C:4](=[O:5])[C@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[NH:14][C:15](=[O:16])[C@@H:17]1[CH2:18][CH2:19][C:20](=[O:21])[NH:22]... | N#CN.O=C1CC[C@@H](C(=O)N[C@@H](Cc2ccccc2)C(=O)O)N1 | N#CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCC(=O)N1 | null | null | C1CCOC1.O | Acylation | Carboxylic acid with primary amine to amide | 1f865723370f71cf1ab7dc00831ab704a96a4326ef6e35f073cf7a866be1f70c | 2e26a213e8110c6a5818ffd27f6c5189453b5abca653629394958b094b8ce114 | O=C1CC[C@@H](C(=O)NCCc2ccccc2)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[N;D1;H0:8]#[C:9]-[NH2;D1;+0:10]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]#[N;D1;H0:8] | 42.5 | [{"value": 42.5, "product": "N1[C@@H](CCC1=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | L-Pyroglutamyl-L-phenylalanine (4.10 g, 0.0148 mol) was allowed to react with DCC (3.37 g, 0.0163 mol) and N-hydroxysuccinimide (1.88 g, 0.0163 mol) in 60 ml of THF at ice bath temperature for 3 hours, and then at room temperature overnight. The reaction mixture was filtered and the filtrate was added drop-wise to a so... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Cyanamide | Cyanamide.Secondary amide | null | null | c1ccccc1.C1CCNC1 | HO- | C1CCOC1.O | null | 6 | N#CN.O=C1CC[C@@H](C(=O)N[C@@H](Cc2ccccc2)C(=O)O)N1>C1CCOC1.O>N#CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCC(=O)N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b22dfcf72698442ba39b7f791a426504 | [Cl-].[Mg+2]>>[Cl-].[Mg+2] | C(C)O.[Cl-].[Mg+2].[Cl-].[Cl-].[Mg+2].[Cl-].C(C)C(CO)CCCC>>[Cl-].[Mg+2].[Cl-].C(C)C(CO)CCCC | [Cl-:10].[Mg+2:12]>>[Cl-:10].[Mg+2:12] | [Cl-].[Mg+2] | [Cl-].[Mg+2] | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | To a sample (50 g, 0.134 mole) of magnesium chloride ethanol adduct prepared as in Example 2 and having an ethanol:magnesium chloride ratio of 6 was added 60 ml of 2-ethyl-1-hexanol. The solution was then distilled at 120° C. to remove ethanol and heptane. Decane (97.7 g) was added to the resulting viscous solution to ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | [Cl-].[Mg+2]>C(C)O>[Cl-].[Mg+2] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-deb5187098a744fe880b2de0378ae21c | O=Cc1ccccc1>>O=Cc1ccccc1 | C(C1=CC=CC=C1)=O.C(C=CC1=CC=CC=C1)=O>>C(C1=CC=CC=C1)=O.C(C=CC1=CC=CC=C1)=O | [O:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | O=Cc1ccccc1 | O=Cc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | FIG. 2 is the GC-IR spectrum for the bottoms in the distillation pot. The peak indicated by reference numeral 20 is the peak for benzaldehyde. The peak indicated by reference numeral 21 is the peak for the cinnamaldehyde.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | null | null | null | O=Cc1ccccc1>>O=Cc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5c4074c08323446d9ace398b44e77c79 | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl>>COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)Cl)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)O)\C)OC)C)=O.S(=O)(Cl)Cl.CN(C=O)C>>OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)Cl)\C)OC)C)=O | O[C:17]([CH2:16][CH2:15]/[C:13](=[CH:12]/[CH2:11][c:10]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[OH:9])[C:20](=[O:21])[O:22][CH2:23]2)[CH3:14])=[O:18].O=S(Cl)[Cl:19]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:10]1[CH2:11]/[CH:12]=[C:13](\[CH3:14])[CH2:15][CH2:16][C:17](=[O:18])[Cl:19])[C:20... | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)Cl)C(=O)OC2 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C1OCc2ccccc21 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]\[C:6]=[C:7]>>[C:7]=[C:6]/[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | 3 | HOUR | E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid (mycophenolic acid) (32.0 g) was dissolved in dichloromethane (250 ml), followed by the addition of thionyl chloride (25.0 ml) and dimethylformamide (0.3 ml). The reaction mixture was stirred at room temperature for 3 hours,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)COC2 | HCl | ClCCl | null | 3 | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.O=S(Cl)Cl>ClCCl>COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)Cl)C(=O)OC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2f2d405188a5411ca7d093dc5156459a | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2.O=C(Cl)C12CC3CC(CC(C3)C1)C2>>COc1c(C)c2c(c(OC(=O)C34CC5CC(CC(C5)C3)C4)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OCCN1CCOCC1)\C)OC)C)=O.C12(CC3CC(CC(C1)C3)C2)C(=O)Cl.O>>C12(CC3CC(CC(C1)C3)C2)C(=O)OC2=C3C(OCC3=C(C(=C2C/C=C(/CCC(=O)OCCN2CCOCC2)\C)OC)C)=O | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:22]1[CH2:23]/[CH:24]=[C:25](\[CH3:26])[CH2:27][CH2:28][C:29](=[O:30])[O:31][CH2:32][CH2:33][N:34]1[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1)[C:40](=[O:41])[O:42][CH2:43]2.Cl[C:10](=[O:11])[C:12]12[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:19]3)[CH2:20]... | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2.O=C(Cl)C12CC3CC(CC(C3)C1)C2 | COc1c(C)c2c(c(OC(=O)C34CC5CC(CC(C5)C3)C4)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | null | null | N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(CCC=CCc1ccc2c(c1OC(=O)C13CC4CC(CC(C4)C1)C3)C(=O)OC2)OCCN1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6]):[c:13] | null | [] | null | null | 90 | MINUTE | Morpholinoethyl E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate (10.0 g) was dissolved in pyridine (50.0 ml) followed by the addition of 1-adamantanecarbonyl chloride (10.0 ml). The mixture was stirred at room temperature for 90 minutes, then poured into water and extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccc2c(c1)COC2.C1COCC[NH]1.C1C2CC3CC1CC(C2)C3 | HCl | N1=CC=CC=C1 | null | 1.5 | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2.O=C(Cl)C12CC3CC(CC(C3)C1)C2>N1=CC=CC=C1>COc1c(C)c2c(c(OC(=O)C34CC5CC(CC(C5)C3)C4)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ce801baf663247ddbe6aa39a88d06aae | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2.O=C(Cl)Cl>>COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OCCN1CCOCC1)\C)OC)C)=O.N1=CC=CC=C1.C(=O)(Cl)Cl>>C(N)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OCCN1CCOCC1)\C)OC)C)=O | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([OH:9])[c:13]1[CH2:14]/[CH:15]=[C:16](\[CH3:17])[CH2:18][CH2:19][C:20](=[O:21])[O:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1)[C:31](=[O:32])[O:33][CH2:34]2.Cl[C:10](Cl)=[O:12]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][C:10]([NH2:11]... | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2.O=C(Cl)Cl | COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 7a500c53e0c90ddb616b1d9844a25d18752778458f7cf9b6b4d76c7f92fd6ed9 | 1c930fd1a8ef596a25a9e8b02e0d655be711516e36782a4da179eb27706d6367 | O=C(CCC=CCc1ccc2c(c1)C(=O)OC2)OCCN1CCOCC1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[N;D1;H2:10])=[O;D1;H0:2]):[c:9] | null | [] | 25 | CELSIUS | 8 | HOUR | To a solution of 500 mgs of morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate in 10 ml of benzene cooled in an ice bath is added 0.1 ml of pyridine and 6 ml of a 12.5% solution of phosgene in benzene. The solution is stirred at 25° C. overnight, the precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Aromatic alcohol | Carbamic ester | null | null | C1COCC[NH]1.c1ccc2c(c1)COC2 | Other | C1=CC=CC=C1 | 25 | 8 | COc1c(C)c2c(c(O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2.O=C(Cl)Cl>C1=CC=CC=C1>COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8099b77f8ff84220a75161afb1f5b51b | COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.OCCN1CCOCC1>>COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | C(N)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)O)\C)OC)C)=O.C1(CCCCC1)N=C=NC1CCCCC1.OCCN1CCOCC1>>C(N)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OCCN1CCOCC1)\C)OC)C)=O | O[C:20]([CH2:19][CH2:18]/[C:16](=[CH:15]/[CH2:14][c:13]1[c:3]([O:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[O:9][C:10]([NH2:11])=[O:12])[C:31](=[O:32])[O:33][CH2:34]2)[CH3:17])=[O:21].[OH:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([O:9][C:10]([NH... | COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.OCCN1CCOCC1 | COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 | null | null | C1CCOC1 | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CCC=CCc1ccc2c(c1)C(=O)OC2)OCCN1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]\[C:5]=[C:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:6]=[C:5]/[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C:7] | null | [] | null | null | 6 | HOUR | To 1.0 g of E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid dissolved in 20 ml of dry THF is added 0.59 g of dicyclohexylcarbodiimide and 0.037 g of N-(2-hydroxyethyl)morpholine. The mixture is left at room temperature for 6 hours, then evaporated to dryness. The res... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1COCC[NH]1.c1ccc2c(c1)COC2 | HO- | C1CCOC1 | null | 6 | COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.OCCN1CCOCC1>C1CCOC1>COc1c(C)c2c(c(OC(N)=O)c1C/C=C(\C)CCC(=O)OCCN1CCOCC1)C(=O)OC2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dbacce31933a4d398510bac67d92c6e7 | CC1(C(=O)O)CCCCC1>>CC(O)C1CCCCC1 | B.C1CCOC1.CC1(CCCCC1)C(=O)O.B.C1CCOC1>>CC(O)C1CCCCC1 | O=[C:2]([OH:3])[C:4]1([CH3:1])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[CH3:1][CH:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1 | CC1(C(=O)O)CCCCC1 | CC(O)C1CCCCC1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 02693450693b5ad939656da33c0df49f70956a83b5ea223cc76f107c32825f6a | f1507539d754dbc80163ef9a22943a8dfdc34c3cb8fad36821712aaada773cb8 | C1CCCCC1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C;H0;D4;+0:3](-[CH3;D1;+0:4])(-[C:5]-[C:6])-[C:7]-[C:8]>>[C:6]-[C:5]-[CH;D3;+0:3](-[CH;D3;+0:1](-[CH3;D1;+0:4])-[O;D1;H1:2])-[C:7]-[C:8] | null | [] | 5 | CELSIUS | 5 | MINUTE | A three liter, three necked round bottom flask was equipped with a thermometer, magnetic stirrer, argon inlet and outlet adapters and a one liter addition funnel containing 922 ml of 1.0 molar BH3.THF. 1-Methyl cyclohexanecarboxylic acid (119.2 g; 0.84 m) was added to the reaction vessel and dissolved in 100 ml of THF.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary alcohol | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | Other | C1CCOC1 | 5 | 0.083333 | CC1(C(=O)O)CCCCC1>C1CCOC1>CC(O)C1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-45c157a66bd1401c8d8bebfdf83470d2 | C1CCNC1.CC(C)(C)CO.ClCC1CO1>>CC(C)(C)COCC(O)CN1CCCC1 | N1CCCC1.[OH-].[Na+].C(Cl)C1CO1.C(C(C)(C)C)O>>CC(COCC(CN1CCCC1)O)(C)C | [NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1.[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][OH:6].Cl[CH2:7][CH:8]1[O:9][CH2:10]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][O:6][CH2:7][CH:8]([OH:9])[CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | C1CCNC1.CC(C)(C)CO.ClCC1CO1 | CC(C)(C)COCC(O)CN1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f655b63b9e45f6ad5030684084cf6286e38e5915a3fb4f9a1c759f986198f248 | f705254aa09bb51ef7de20148bd7444ecce3ca8ae0af005a4c2394ce21658de8 | C1CCNC1 | Cl-[CH2;D2;+0:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[C:5]-[C:6]-[OH;D1;+0:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1 | 84.1 | [{"value": 84.1, "product": "CC(COCC(CN1CCCC1)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | To a stirred mixture of 92.53 g (1.0 m) of epichlorohydrin and 88.15 g (1.0 m) of neopentyl alcohol was added 0.26 g (0.001 m) of stannic chloride. The reaction temperature rose to about 60° C. then exothermed to about 130° C. in a few seconds. The reaction mixture was stirred until the temperature receded to about 40°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary alcohol.Secondary amine | Ether.Secondary alcohol.Tertiary amine | C1CCNC1.C1CO1 | C1CC[NH]C1 | C1CC[NH]C1 | HCl | null | 95 | null | C1CCNC1.CC(C)(C)CO.ClCC1CO1>>CC(C)(C)COCC(O)CN1CCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a628bb901d9b42bc84a06439d0456eed | C1CCNC1.CC(C)(C)O.ClCC1CO1>>CC(C)(C)OCC(O)CN1CCCC1 | C(C)(C)(C)O.C(Cl)C1CO1.[OH-].[Na+].N1CCCC1>>CC(C)(OCC(CN1CCCC1)O)C | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.[CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].Cl[CH2:6][CH:7]1[O:8][CH2:9]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][CH2:6][CH:7]([OH:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | C1CCNC1.CC(C)(C)O.ClCC1CO1 | CC(C)(C)OCC(O)CN1CCCC1 | null | [Sn](Cl)(Cl)(Cl)Cl | O | Heteroatom Alkylation and Arylation | OtherReaction | cab3417d145cb649aab2859d86bc77c26251a64f18ffe518c132eaad15f036a7 | eba4cd7e03ae0e735f7b27cf7de068bb9cce248c9fa86b1e9bd11f0eb4a58d43 | C1CCNC1 | Cl-[CH2;D2;+0:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[OH;D1;+0:9].[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[N;H0;D3;+0:14]1-[C:10]-[C:11]-[C:12]-[C:13]-1 | 82.6 | [{"value": 82.6, "product": "CC(C)(OCC(CN1CCCC1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 100.0 g (1.35 m) of tert.butyl alcohol and 51.4 g (1.35 m) of epichlorohydrin in 240 ml of xylenes was stirred and heated to 50° C. Tin (IV) chloride (3.5 g; 1.6 ml; 0.031 m) was added all at once and the reaction mixture immediately exothermed to about 100° C. The reaction mixture was stirred at about 50°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Tertiary alcohol.Secondary amine | Ether.Secondary alcohol.Tertiary amine | C1CCNC1.C1CO1 | C1CC[NH]C1 | C1CC[NH]C1 | HCl | [Sn](Cl)(Cl)(Cl)Cl.O | 50 | null | C1CCNC1.CC(C)(C)O.ClCC1CO1>[Sn](Cl)(Cl)(Cl)Cl.O>CC(C)(C)OCC(O)CN1CCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-241aa2d333114c3fb4a89c919eca50fd | CC(C)(C)OCC(O)CN1CCCC1.ClP(Cl)(Cl)(Cl)Cl>>CC(C)(C)OCC(Cl)CN1CCCC1 | CC(C)(OCC(CN1CCCC1)O)C.Cl.P(Cl)(Cl)(Cl)(Cl)Cl>>ClC(CN1CCCC1)COC(C)(C)C | O[CH:7]([CH2:6][O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.ClP(Cl)(Cl)(Cl)[Cl:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][CH2:6][CH:7]([Cl:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | CC(C)(C)OCC(O)CN1CCCC1.ClP(Cl)(Cl)(Cl)Cl | CC(C)(C)OCC(Cl)CN1CCCC1 | null | null | C1(=CC=CC=C1)C.O1CCCC1 | Functional Group Interconversion | Alcohol to chloride_Other | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | C1CCNC1 | Cl-P(-Cl)(-Cl)(-Cl)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-[C:9]-[#7:10]>>[#7:10]-[C:9]-[CH;D3;+0:2](-[Cl;H0;D1;+0:1])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8] | null | [] | null | null | 1.5 | HOUR | To a stirred, cooled suspension of 34.7 g (0.167 ml) of phosphorous pentachloride in 20 ml of dry toluene (argon atmosphere) was added a solution of 31.93 g (0.159 m) of 1-[3-(1,1-dimethylethoxy)-2-hydroxypropyl]pyrrolidine (the product of Example 13a) and excess hydrogen chloride (gas) in 46 ml of dry toluene and 50 m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | C1CC[NH]C1 | HCl | C1(=CC=CC=C1)C.O1CCCC1 | null | 1.5 | CC(C)(C)OCC(O)CN1CCCC1.ClP(Cl)(Cl)(Cl)Cl>C1(=CC=CC=C1)C.O1CCCC1>CC(C)(C)OCC(Cl)CN1CCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-218fc6652d2242c19817433db7fef78c | NCCCCl.c1cnc2c(c1)CCCC2>>NCCCC1CCCc2cccnc21 | N1=CC=CC=2CCCCC12.[NH2-].[Na+].Cl.ClCCCN>>N1=CC=CC=2CCCC(C12)CCCN | Cl[CH2:4][CH2:3][CH2:2][NH2:1].[CH2:5]1[CH2:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]21>>[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]21 | NCCCCl.c1cnc2c(c1)CCCC2 | NCCCC1CCCc2cccnc21 | null | null | N | C-C Coupling | OtherReaction | b6764dd5aaa2dc3bd963b96096138e9182d18bb5e7c8dab9ac20b36892d5bd4b | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1cnc2c(c1)CCCC2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:6](-[C:5]-[C:4])-[c:7](:[c:8]):[#7;a:9]:[c:10] | 26.5 | [{"value": 26.5, "product": "N1=CC=CC=2CCCC(C12)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 5,6,7,8-Tetrahydroquinoline (20 g) was added quickly to sodamide (17.6 g) in liquid ammonia (250 ml) to give a dark red coloured solution. 3-Chloropropylamine hydrochloride (28.9 g) was added in portions over four hours when loss of colour was permanent after which the reaction was stirred for a further 2 hours and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | HCl | N | null | 2 | NCCCCl.c1cnc2c(c1)CCCC2>N>NCCCC1CCCc2cccnc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9fa178249b754b389254ccf16bc7859d | Cc1ccc(Cc2c[nH]c(N[N+](=O)[O-])nc2=O)cn1.NCCCC1CCCc2cccnc21>>Cc1ccc(Cc2c[nH]c(NCCCC3CCCc4cccnc43)nc2=O)cn1 | N1=CC=CC=2CCCC(C12)CCCN.[N+](=O)([O-])NC=1NC=C(C(N1)=O)CC=1C=NC(=CC1)C>>N1=CC=CC=2CCCC(C12)CCCNC=1NC=C(C(N1)=O)CC=1C=NC(=CC1)C | O=[N+]([O-])N[c:10]1[nH:9][cH:8][c:7]([CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:29][cH:28]2)[c:26](=[O:27])[n:25]1.[NH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][n:23][c:24]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][nH:9][c:10]([NH:11][CH2:12][CH2:13][CH2:14][CH... | Cc1ccc(Cc2c[nH]c(N[N+](=O)[O-])nc2=O)cn1.NCCCC1CCCc2cccnc21 | Cc1ccc(Cc2c[nH]c(NCCCC3CCCc4cccnc43)nc2=O)cn1 | null | null | N1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 05b684912773000dd80e55082a7a1b852822633f01eaa1fe214d84d8b29bbd58 | a08d030a1a70ff4a445173118d028d17232424f5644d46118c3f0ed4772c2485 | O=c1nc(NCCCC2CCCc3cccnc32)[nH]cc1Cc1cccnc1 | O=[N+](-[O-])-N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 26.4 | [{"value": 26.4, "product": "N1=CC=CC=2CCCC(C12)CCCNC=1NC=C(C(N1)=O)CC=1C=NC(=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(5,6,7,8-tetrahydroquinol-8-yl)-propylamine (0.75 g, 0.0038 mole) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4(1H)-pyrimidone (0.99 g, 0.0037 mole) in pyridine (1 ml) was refluxed for 8 hr and evaporated to dryness. The residue was chromatographed on silica in 10% MeOH/CHCl3 then dissolved in hot CHC... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccncc1.c1cncnc1.c1cnc2c(c1)CCCC2 | HO- | N1=CC=CC=C1 | null | null | Cc1ccc(Cc2c[nH]c(N[N+](=O)[O-])nc2=O)cn1.NCCCC1CCCc2cccnc21>N1=CC=CC=C1>Cc1ccc(Cc2c[nH]c(NCCCC3CCCc4cccnc43)nc2=O)cn1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ecedeae11bc2433581aed340c21acce6 | Brc1cncnc1.COC(=O)c1ccc(Cl)cc1Cl>>O=C(c1cncnc1)c1ccc(Cl)cc1Cl | C(CCC)[Li].[Cl-].[NH4+].ClC1=C(C(=O)OC)C=CC(=C1)Cl.BrC=1C=NC=NC1>>ClC1=C(C(=O)C=2C=NC=NC2)C=CC(=C1)Cl | Br[c:3]1[cH:4][n:5][cH:6][n:7][cH:8]1.CO[C:2](=[O:1])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16]>>[O:1]=[C:2]([c:3]1[cH:4][n:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16] | Brc1cncnc1.COC(=O)c1ccc(Cl)cc1Cl | O=C(c1cncnc1)c1ccc(Cl)cc1Cl | null | null | CCCCCC.O1CCCC1.C(C)OCC | C-C Coupling | Ester and halide to ketone | bb0648e8f53cb690526a8f718157b4e43d22f41b3fb2a22a100bc7b75c3830db | 7000e6fa6236297c1c515ebeaf5c7ba17704e006a4336e184f2503c0f1949baf | O=C(c1ccccc1)c1cncnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.C-O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]>>[O;D1;H0:8]=[C;H0;D3;+0:7](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | null | null | 0.5 | HOUR | 61.8 g (0.3 mole) of methyl 2,4-dichlorobenzoate and 52.2 g (0.33 mole) of 5-bromopyrimidine are dissolved in a mixture of 400 ml of tetrahydrofuran and 200 ml of diethyl ether. After the addition of 30 g of molecular sieve, the reaction mixture is stirred for 1/2 hour at room temperature and then cooled to about -120°... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ketone | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HBr | CCCCCC.O1CCCC1.C(C)OCC | null | 0.5 | Brc1cncnc1.COC(=O)c1ccc(Cl)cc1Cl>CCCCCC.O1CCCC1.C(C)OCC>O=C(c1cncnc1)c1ccc(Cl)cc1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-21579b9c6dbe424cb126459426052c6c | Clc1ncc(Br)cn1.Nc1ccc(O)c(Cl)c1>>Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 | BrC=1C=NC(=NC1)Cl.NC1=CC(=C(C=C1)O)Cl.C([O-])([O-])=O.[K+].[K+].CS(=O)C>>BrC=1C=NC(=NC1)OC1=C(C=C(N)C=C1)Cl | Cl[c:7]1[n:8][cH:9][c:10]([Br:11])[cH:12][n:13]1.[NH2:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:14]([Cl:15])[cH:16]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[n:8][cH:9][c:10]([Br:11])[cH:12][n:13]2)[c:14]([Cl:15])[cH:16]1 | Clc1ncc(Br)cn1.Nc1ccc(O)c(Cl)c1 | Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 62.6 | [{"value": 62.6, "product": "BrC=1C=NC(=NC1)OC1=C(C=C(N)C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a flask, 7.00 g of 5-bromo-2-chloropyrimidine, 5.19 g of 4-amino-2-chlorophenol, 9.98 g of potassium carbonate and 70 ml of dimethylsulfoxide were introduced, and reacted in a nitrogen atmosphere at 120° C. for 1.5 hours under stirring. After the completion of the reaction, the product was poured into water, and e... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | O | null | null | Clc1ncc(Br)cn1.Nc1ccc(O)c(Cl)c1>O>Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5d8975024a1740ce98c9290e59b3aec3 | Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1.O=C=NC(=O)c1ccccc1[N+](=O)[O-]>>O=C(NC(=O)c1ccccc1[N+](=O)[O-])Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 | CO.BrC=1C=NC(=NC1)OC1=C(C=C(N)C=C1)Cl.[N+](=O)([O-])C1=C(C(=O)N=C=O)C=CC=C1.O>>[N+](=O)([O-])C1=C(C(=O)NC(=O)NC2=CC(=C(C=C2)OC2=NC=C(C=N2)Br)Cl)C=CC=C1 | [NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[n:22][cH:23][c:24]([Br:25])[cH:26][n:27]2)[c:28]([Cl:29])[cH:30]1.[O:1]=[C:2]=[N:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14]>>[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14])[NH:15][c:16]1[cH:... | Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1.O=C=NC(=O)c1ccccc1[N+](=O)[O-] | O=C(NC(=O)c1ccccc1[N+](=O)[O-])Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 | null | null | O1CCOCC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NC(=O)c1ccccc1)Nc1ccc(Oc2ncccn2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10] | 84.5 | [{"value": 84.5, "product": "[N+](=O)([O-])C1=C(C(=O)NC(=O)NC2=CC(=C(C=C2)OC2=NC=C(C=N2)Br)Cl)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a flask, a solution obtained by dissolving 6.80 g of the above 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline in 30 ml of dioxane, was introduced, and a solution obtained by dissolving 5.76 g of 2-nitrobenzoylisocyanate in 30 ml of dioxane, was dropwise added thereto, and then the mixture was reacted at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1.c1cncnc1 | null | O1CCOCC1 | null | null | Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1.O=C=NC(=O)c1ccccc1[N+](=O)[O-]>O1CCOCC1>O=C(NC(=O)c1ccccc1[N+](=O)[O-])Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9d1b517cc1984e3fb05e9d6f78f2916e | Clc1cnc(Cl)nc1.Nc1ccc(O)c(Cl)c1>>Nc1ccc(Oc2ncc(Cl)cn2)c(Cl)c1 | [N+](=O)([O-])C1=C(C(=O)NC(=O)NC2=CC(=C(C=C2)OC2=NC=C(C=N2)Cl)Cl)C=CC=C1.ClC1=NC=C(C=N1)Cl.NC1=CC(=C(C=C1)O)Cl.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(N)C=CC1OC1=NC=C(C=N1)Cl | Cl[c:7]1[n:8][cH:9][c:10]([Cl:11])[cH:12][n:13]1.[NH2:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:14]([Cl:15])[cH:16]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[n:8][cH:9][c:10]([Cl:11])[cH:12][n:13]2)[c:14]([Cl:15])[cH:16]1 | Clc1cnc(Cl)nc1.Nc1ccc(O)c(Cl)c1 | Nc1ccc(Oc2ncc(Cl)cn2)c(Cl)c1 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | N-(2-nitrobenzoyl)-N'-[3-chloro-4-(5-chloro-2-pyrimidinyloxy)phenyl]urea (1) Into a flask, 1.50 g of 2,5-dichloropyrimidine, 1.45 g of 4-amino-2-chlorophenol, 2.76 g of potassium carbonate and 15 ml of dimethylsulfoxide, were introduced, and reacted in a nitrogen atmosphere at 100° C. for 1.5 hours under stirring. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | CS(=O)C.O | null | null | Clc1cnc(Cl)nc1.Nc1ccc(O)c(Cl)c1>CS(=O)C.O>Nc1ccc(Oc2ncc(Cl)cn2)c(Cl)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7ff718f3b7e94c629eff1d63f4573f1b | Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1.O=C(Cl)Cl>>O=C=Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 | C(=O)(Cl)Cl.BrC=1C=NC(=NC1)OC1=C(C=C(N)C=C1)Cl>>BrC=1C=NC(=NC1)OC1=C(C=C(C=C1)N=C=O)Cl | [NH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[n:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[c:16]([Cl:17])[cH:18]1.Cl[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[n:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[c:16]([Cl:17])[cH:18]1 | Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1.O=C(Cl)Cl | O=C=Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccc(Oc2ncccn2)cc1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 95.1 | [{"value": 95.1, "product": "BrC=1C=NC(=NC1)OC1=C(C=C(C=C1)N=C=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a flask, a solution of 0.02 mol of phosgene in 30 ml of ethyl acetate was introduced. To this solution, a solution of 3 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline in 10 ml of ethyl acetate was dropwise added at room temperature. The mixture was reacted at room temperature for 3 hours under stirring and furt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccccc1.c1cncnc1 | HCl | C(C)(=O)OCC | null | null | Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1.O=C(Cl)Cl>C(C)(=O)OCC>O=C=Nc1ccc(Oc2ncc(Br)cn2)c(Cl)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4dcca75acd3843ae9e867d6f1684e2bb | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1ccccc1)c1cccnc1>>O=C(O)CCCC/C=C(/c1ccccc1)c1cccnc1 | [Br-].C(=O)(O)CCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)C.[H-].[Na+].C(C1=CC=CC=C1)(=O)C=1C=NC=CC1>>N1=CC(=CC=C1)\C(=C/CCCCC(=O)O)\C1=CC=CC=C1 | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])cc1.O=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9](/[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][... | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1ccccc1)c1cccnc1 | O=C(O)CCCC/C=C(/c1ccccc1)c1cccnc1 | null | null | O.O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 6dd0a5c38831fb7d6f247fdce547914e97c2a39af502d5696ce93cba92b782d4 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | [CH]=C(c1ccccc1)c1cccnc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9].[C:10]-[C:11]-[CH2;D2;+0:12]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:10]-[C:11]/[CH;D2;+0:12]=[C;H0;D3;+0:1](/[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 80 | [{"value": 79.0, "product": "N1=CC(=CC=C1)\\C(=C/CCCCC(=O)O)\\C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "N1=CC(=CC=C1)\\C(=C/CCCCC(=O)O)\\C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 5 | MINUTE | To dimethylsulfoxide (40 ml) was added dropwise sodium hydride (1.0 g), and the mixture was heated at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, to which was added 5-carboxypentyltriphenyl phosphonium bromide (9.5 g, 21 mmoles) and the mixture was stirred for 5 minutes. To the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccncc1 | HO- | O.O1CCCC1 | 80 | 0.083333 | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1ccccc1)c1cccnc1>O.O1CCCC1>O=C(O)CCCC/C=C(/c1ccccc1)c1cccnc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5655146716e448659bad88b9b85685fd | C=CC(O)(c1ccccc1)c1cccnc1.COC(=O)c1cccc(O)c1>>COC(=O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1 | P(Cl)(Cl)(Cl)(Cl)Cl.[H-].[Na+].OC=1C=C(C(=O)OC)C=CC1.C1(=CC=CC=C1)C(C=C)(O)C=1C=NC=CC1>>N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)OC)C=CC1)C1=CC=CC=C1 | O[C:13]([CH:12]=[CH2:11])([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]=[C:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]... | C=CC(O)(c1ccccc1)c1cccnc1.COC(=O)c1cccc(O)c1 | COC(=O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1 | null | null | ClCCl.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 6dd1031b55c8988c52506353b9f12735a423d806dc625fb675a31a2e2a3f0c29 | 4b905ec47df6dc7f9816cc6f36157b531561efa990c5cc2eaa8ddf31db051e9d | C(COc1ccccc1)=C(c1ccccc1)c1cccnc1 | O-[C;H0;D4;+0:1](-[CH;D2;+0:2]=[CH2;D1;+0:3])(-[c:4](:[c:5]):[c:6])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[c:5]:[c:4](-[C;H0;D3;+0:1](=[CH;D2;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]):[c:6] | 96.5 | [{"value": 92.0, "product": "N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)OC)C=CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.5, "product": "N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)OC)C=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Phosphorus pentachloride (3.0 g, 14.2 mmoles) was suspended in dichloromethane (4 ml). To the suspension was added dropwise a solution of 1-phenyl-1-(3-pyridyl)-2-propen-1-ol (2.0 g, 9.5 mmoles) in dichloromethane (20 ml) at 0° C., then the mixture was stirred for one hour at room temperature, followed by washing with ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Aromatic alcohol.Vinyl | Ether | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | HO- | ClCCl.CN(C=O)C | null | 1 | C=CC(O)(c1ccccc1)c1cccnc1.COC(=O)c1cccc(O)c1>ClCCl.CN(C=O)C>COC(=O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b8e8a0e44dc8447099988bc5cd8e65ec | COC(=O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1>>O=C(O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1 | N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)OC)C=CC1)C1=CC=CC=C1.[OH-].[Na+].Cl>>N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]=[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][n:23][cH:24]2)[cH:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]=[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:... | COC(=O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1 | O=C(O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C(COc1ccccc1)=C(c1ccccc1)c1cccnc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 80 | [{"value": 80.0, "product": "N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | Methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate (If-56, 1.5 g, 4.35 mmoles) was dissolved in a mixture of water (3 ml) and methanol (10 ml). To the solution was added sodium hydroxide (700 mg, 17.5 mmoles). The mixture was stirred for 2 hours at 60° C., which was then left standing for cooling. To the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | Other | CO.O | 60 | 2 | COC(=O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1>CO.O>O=C(O)c1cccc(OCC=C(c2ccccc2)c2cccnc2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-044f299de98846bab0cf25d80cf220f1 | CCN(CC)CCn1nc2c3c(c(CO)ccc31)Sc1cc(Cl)ccc1-2>>Cl | N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C1=CC=CC=C1.CCN(CC)CCN1C2=C3C(=C(C=C2)CO)SC4=C(C3=N1)C=CC(=C4)Cl>>Cl.N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C1=CC=CC=C1 | CCN(CC)CCn1nc2c3c(c(CO)ccc31)Sc1cc([Cl:1])ccc1-2>>[ClH:1] | CCN(CC)CCn1nc2c3c(c(CO)ccc31)Sc1cc(Cl)ccc1-2 | Cl | null | null | Cl | Reduction | OtherReaction | 7f6e9d0c2b31a05c545a6fe90c98490646ba31bf2fcf7da30c3d5d3bcae5a4b7 | a8fe5a648487d7d872f64daf4ea9ebf311e852d3acc149475b7d310b975d36e4 | null | C-C-N(-C-C)-C-C-n1:n:c2:c3:c(:c(-C-O):c:c:c:3:1)-S-c1:c:c(-[Cl;H0;D1;+0:1]):c:c:c:1-2>>[ClH;D0;+0:1] | null | [] | null | null | null | null | To (E)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid (Ia-4, 300 mg was dissolved in 2N HCl (5 ml). The solution was concentrated under reduced pressure. Recrystallization of the resulting crystals from ethanol-isopropyl ether gave (E)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid hydrochloride (Ii-75) (285 mg), m.p. 163°-165° C. P... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Tertiary amine.Monosulfide | null | c1ccc2c(c1)Sc1cccc3[nH]nc2c13 | null | null | Other | Cl | null | null | CCN(CC)CCn1nc2c3c(c(CO)ccc31)Sc1cc(Cl)ccc1-2>Cl>Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f4d40c8105a54f1dabfdfe034ad81e84 | O=C(O)CCCC/C=C(\c1ccccc1)c1cccnc1>>O=C([O-])CCCC/C=C(\c1ccccc1)c1cccnc1 | N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C1=CC=CC=C1.C(O)([O-])=O.[Na+]>>N1=CC(=CC=C1)/C(=C/CCCCC(=O)[O-])/C1=CC=CC=C1.[Na+] | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9](\[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[O:1]=[C:2]([O-:3])[CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9](\[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1 | O=C(O)CCCC/C=C(\c1ccccc1)c1cccnc1 | O=C([O-])CCCC/C=C(\c1ccccc1)c1cccnc1 | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | [CH]=C(c1ccccc1)c1cccnc1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | 55.7 | [{"value": 55.7, "product": "N1=CC(=CC=C1)/C(=C/CCCCC(=O)[O-])/C1=CC=CC=C1.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (E)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid (Ia-4) (500 mg) and sodium hydrogen carbonate (160 mg) were added to water (5 ml) to make a homogeneous solution. The solution was concentrated under reduced pressure. The concentrate was pulverized by the use of ethanol-isopropylether to obtain sodium (E)-7-(3-pyridyl)-7-phe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1.c1ccncc1 | null | O | null | null | O=C(O)CCCC/C=C(\c1ccccc1)c1cccnc1>O>O=C([O-])CCCC/C=C(\c1ccccc1)c1cccnc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a74b6d8de3c74927ba4f80b2e8d86f3c | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1cccnc1)c1ccc2c(c1)OCO2>>O=C(O)CCCC/C=C(\c1cccnc1)c1ccc2c(c1)OCO2 | C1OC=2C=C(C(=O)C=3C=NC=CC3)C=CC2O1.[H-].[Na+].CS(=O)C.[Br-].C(=O)(O)CCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C1OC=2C=C(C=CC2O1)/C(=C/CCCCC(=O)O)/C=1C=NC=CC1 | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])cc1.O=[C:9]([c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][CH2:23][O:24]2>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9](\[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1)[c:16]1[... | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1cccnc1)c1ccc2c(c1)OCO2 | O=C(O)CCCC/C=C(\c1cccnc1)c1ccc2c(c1)OCO2 | null | null | O.O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 6dd0a5c38831fb7d6f247fdce547914e97c2a39af502d5696ce93cba92b782d4 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | [CH]=C(c1cccnc1)c1ccc2c(c1)OCO2 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[c:7](:[c:8]):[c:9].[C:10]-[C:11]-[CH2;D2;+0:12]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:10]-[C:11]/[CH;D2;+0:12]=[C;H0;D3;+0:1](\[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[c:7](:[c:8]):[c:9] | 24.6 | [{"value": 24.6, "product": "C1OC=2C=C(C=CC2O1)/C(=C/CCCCC(=O)O)/C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.2, "product": "C1OC=2C=C(C=CC2O1)/C(=C/CCCCC(=O)O)/C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Sodium hydride (1 g, 60% in oil) was added to dimethyl sulfoxide (25 ml) under nitrogen and the mixture was heated at 85° C. with stirring for an hour. The reaction mixture was cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (5.2 g, 11 mmoles) was added gradually. The mixture was stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccncc1.c1ccc2c(c1)OCO2 | HO- | O.O1CCCC1 | 85 | null | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1cccnc1)c1ccc2c(c1)OCO2>O.O1CCCC1>O=C(O)CCCC/C=C(\c1cccnc1)c1ccc2c(c1)OCO2 |
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