dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a7f27325a7db463097aa4e14db1b2c3d | O=Cc1ccccc1Br.O=Cc1ccccn1.[Li][CH2]CCC>>CCCCC(O)C1=CC=CCC1(O)Cc1ccccn1 | N1=C(C=CC=C1)C=O.C(CCC)[Li].BrC1=C(C=O)C=CC=C1.CCOCC.C(CCC)[Li].[Cl-].[NH4+]>>OC1(CC2=NC=CC=C2)CC=CC=C1C(CCCC)O | Br[c:12]1[c:7]([CH:5]=[O:6])[cH:8][cH:9][cH:10][cH:11]1.[O:13]=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1.[Li][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([OH:6])[C:7]1=[CH:8][CH:9]=[CH:10][CH2:11][C:12]1([OH:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1 | O=Cc1ccccc1Br.O=Cc1ccccn1.[Li][CH2]CCC | CCCCC(O)C1=CC=CCC1(O)Cc1ccccn1 | null | null | CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | e031a0f480b28d7406c9fbcd18b24b11407fff24d3f8282fb50539c418e7ad54 | a92b097469f48c59253e44991e52c5ed7691955dc06e514e3062f5db527f870d | C1=CCC(Cc2ccccn2)C=C1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6]:1-[CH;D2;+0:7]=[O;H0;D1;+0:8].[C:9]-[C:10]-[CH2;D2;+0:11]-[Li].[O;H0;D1;+0:12]=[CH;D2;+0:13]-[c:14](:[c:15]):[#7;a:16]:[c:17]>>[C:9]-[C:10]-[CH2;D2;+0:11]-[CH;D3;+0:7](-[OH;D1;+0:8])-[C;H0;D3;+0:6]1=[CH;D2;+0:5]-[CH;D2;+0:4]=[CH;D2;+0... | 83.2 | [{"value": 83.2, "product": "OC1(CC2=NC=CC=C2)CC=CC=C1C(CCCC)O", "details": "PERCENTYIELD", "is_desired": false}] | -45 | CELSIUS | 0.5 | HOUR | To a mixture of 10 mL (85.6 mmol) of 2-bromobenzaldehyde in 300 mL of ether cooled to -45° C. was added in portions 8.56 mL (85.6 mmol) of 10M n-butyllithium in hexane over a 20 min period, and the reaction mixture was stirred at -20 for 1/2 h. To the above reaction mixture cooled to -20° C., was added 8.98 mL (88.9 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Aldehyde.Alkyl lithium | Secondary alcohol.Tertiary alcohol.Conjugated diene | c1ccccc1 | C1=CCCC=C1 | C1=CCCC=C1.c1ccncc1 | Br-.Li | CCCCCC | -45 | 0.5 | O=Cc1ccccc1Br.O=Cc1ccccn1.[Li][CH2]CCC>CCCCCC>CCCCC(O)C1=CC=CCC1(O)Cc1ccccn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6f930ecb5bb04d1aa44f812c6ea43e74 | CCCCC(O)C1=CC=CCC1(O)Cc1ccccn1>>CCCCc1c2ccccc2cc2cccc[n+]12 | Cl(=O)(=O)(=O)[O-].[Na+].OC1(CC2=NC=CC=C2)CC=CC=C1C(CCCC)O.S(=O)(=O)(C(F)(F)F)OS(=O)(=O)C(F)(F)F>>Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2 | O[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:6]1=[CH:7][CH:8]=[CH:9][CH2:10][C:11]1(O)[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n+:18]12 | CCCCC(O)C1=CC=CCC1(O)Cc1ccccn1 | CCCCc1c2ccccc2cc2cccc[n+]12 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | c84f3868e0c6722589014de7c60aedba9f98be30a9ca3e55abd0ea909c901521 | f51c0a0ae7a8de0b25d6d01f96a75e2856b70c8fe670dfe67c4bca77de7114cf | c1ccc2c[n+]3ccccc3cc2c1 | O-[CH;D3;+0:1](-[C:2]-[C:3])-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-[CH2;D2;+0:8]-[C;H0;D4;+0:9]-1(-O)-[CH2;D2;+0:10]-[c:11](:[c:12]):[n;H0;D2;+0:13]:[c:14]:[c:15]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[c;H0;D3;+0:4]2:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9]:2:[cH;D2;+0:10]:[c:11](:[c:1... | 11 | [{"value": 11.0, "product": "Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a refluxing solution of 11.1 g (0.04 mol) of 2-[1-hydroxy-6'-(1-hydroxypentyl)-benzyl]pyridine in 250 mL of benzene was added 23.9 mL (0.14 mol) of triflic anhydride in 5 min, the mixture was heated for 65 min and then cooled. The reaction mixture was concentrated in vacuo, the residual oil was triturated in ether a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Tertiary alcohol.Conjugated diene | null | C1=CCCC=C1.c1ccncc1 | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | HO- | C1=CC=CC=C1 | null | null | CCCCC(O)C1=CC=CCC1(O)Cc1ccccn1>C1=CC=CC=C1>CCCCc1c2ccccc2cc2cccc[n+]12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f95fa9e3ced54384ab73c44eda5cce01 | O=Cc1ccccn1.OCCO>>c1ccc(C2OCCO2)nc1 | O.N1=C(C=CC=C1)C=O.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(OCC1)C1=NC=CC=C1 | [cH:1]1[cH:2][cH:3][c:4]([CH:5]=[O:6])[n:10][cH:11]1.O[CH2:7][CH2:8][OH:9]>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[O:6][CH2:7][CH2:8][O:9]2)[n:10][cH:11]1 | O=Cc1ccccn1.OCCO | c1ccc(C2OCCO2)nc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc(C2OCCO2)nc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[c:9]:[#7;a:8]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1):[c:7] | 29.3 | [{"value": 29.3, "product": "O1C(OCC1)C1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.0, "product": "O1C(OCC1)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-pyridinecarboxaldehyde (2678, 2.5 mol), ethylene glycol (310.35 g, 5 mol), and 118.8 g (0.62 mol) of p-toluenesulfonic acid in 1.5 L of toluene placed in a 3 L flask fined with a Dean Stark trap was allowed to reflux until the removal of water was complete. The mixture was concentrated in vacuo and the r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccncc1.C1COCO1 | HO- | C1(=CC=CC=C1)C | null | null | O=Cc1ccccn1.OCCO>C1(=CC=CC=C1)C>c1ccc(C2OCCO2)nc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-97e68516a7b54210978c6375755505c7 | Cc1cc(Br)ccc1Br.O=C1CCC(=O)N1Br>>BrCc1cc(Br)ccc1Br | BrC1=C(C=C(C=C1)Br)C.C1CC(=O)N(C1=O)Br>>BrC1=C(CBr)C=C(C=C1)Br | [CH3:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]1[Br:10].O=C1CCC(=O)N1[Br:1]>>[Br:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]1[Br:10] | Cc1cc(Br)ccc1Br.O=C1CCC(=O)N1Br | BrCc1cc(Br)ccc1Br | null | C(C1=CC=CC=C1)OOCC1=CC=CC=C1 | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 55.7 | [{"value": 55.7, "product": "BrC1=C(CBr)C=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.2, "product": "BrC1=C(CBr)C=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 75 g (0.3 mol) of 2,5-dibromotoluene in 1 L of carbon tetrachloride was added 58.73 g (0.33 mol) of NBS and 50 mg of benzyl peroxide, and the resulting mixture was refluxed with stirring for 24 h. The mixture was cooled, and concentrated in vacuo. The residue was crystallized from hot methanol and wash... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C1=CC=CC=C1)OOCC1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl | null | 24 | Cc1cc(Br)ccc1Br.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)OOCC1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl>BrCc1cc(Br)ccc1Br |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cc9a8b29702e4dc4a1ee1ef714409b7f | BrCc1cc(Br)ccc1Br.c1ccc(C2OCCO2)nc1>>Brc1ccc(Br)c(C[n+]2ccccc2C2OCCO2)c1.[Br-] | O1C(OCC1)C1=NC=CC=C1.BrC1=C(CBr)C=C(C=C1)Br>>[Br-].BrC1=C(C[N+]2=C(C=CC=C2)C2OCCO2)C=C(C=C1)Br | [Br:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[c:7]([CH2:8][Br:21])[cH:20]1.[n:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[CH:15]1[O:16][CH2:17][CH2:18][O:19]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[c:7]([CH2:8][n+:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH:15]2[O:16][CH2:17][CH2:18][O:19]2)[cH:20]1.[Br-:21] | BrCc1cc(Br)ccc1Br.c1ccc(C2OCCO2)nc1 | Brc1ccc(Br)c(C[n+]2ccccc2C2OCCO2)c1.[Br-] | null | null | S1(=O)(=O)CCCC1.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | e56fd11791c067861416b6f318bdb2898b5c0e8f298d85abbe02936af387902e | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(C[n+]2ccccc2C2OCCO2)cc1 | [#8:1]-[C:2](-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7])-[#8:8].[Br;H0;D1;+0:9]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[C:2](-[c:3](:[c:4]):[n+;H0;D3:5](-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:6]:[c:7])-[#8:8].[Br-;H0;D0:9] | 79 | [{"value": 79.0, "product": "[Br-].BrC1=C(C[N+]2=C(C=CC=C2)C2OCCO2)C=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "[Br-].BrC1=C(C[N+]2=C(C=CC=C2)C2OCCO2)C=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 25.03 g (0.165 mol) of 2-(1,3-dioxolan-2-yl)-pyridine and 2,5-dibromobenzyl bromide (54 g, 0,165 mol) in 60 mL of sulfolane was heated on a steam-bath for 6 h. The mixture was diluted with 600 mL of ethyl acetate, cooled, and the resulting solid product was isolated by filtration. The above solid was tritu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1.C1COCO1 | null | S1(=O)(=O)CCCC1.C(C)(=O)OCC | null | null | BrCc1cc(Br)ccc1Br.c1ccc(C2OCCO2)nc1>S1(=O)(=O)CCCC1.C(C)(=O)OCC>Brc1ccc(Br)c(C[n+]2ccccc2C2OCCO2)c1.[Br-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7efa731e8f694dbfb068dab0ee90d921 | c1ccc2c[n+]3ccccc3cc2c1>>c1ccc2c(c1)Cc1cccc[n+]1C2 | Cl(=O)(=O)(=O)[O-].C1=CC=C[N+]=2C=C3C(=CC12)C=CC=C3.COC1=CC=C(CN2N=C(C=C2)C(=C)C2=NN(C=C2)CC2=CC=C(C=C2)OC)C=C1>>Cl(=O)(=O)(=O)[O-].C1=CC=C[N+]=2CC3=C(CC12)C=CC=C3 | [cH:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[cH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][n+:18]1[cH:19]2>>[cH:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][n+:18]1[CH2:19]2 | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c(c1)Cc1cccc[n+]1C2 | null | null | [N+](=O)([O-])C | Reduction | OtherReaction | 7cdb7aaca538fff6a3dac1c2ddd900795b832d55bb2ce8c0d156d768f2ba1c03 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2c(c1)Cc1cccc[n+]1C2 | [c:1]:[c:2]1:[cH;D2;+0:3]:[c:4](:[c:5]):[#7;a;+:6](:[c:7]):[cH;D2;+0:8]:[c:9]:1:[c:10]>>[c:1]:[c:2]1:[c:9](:[c:10])-[CH2;D2;+0:8]-[#7;a;+:6](:[c:7]):[c:4](:[c:5])-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | A reaction mixture containing benzo[b]quinolizinium perchlorate (9.5 g; 6.8 mmol) and 1,1-di-[(1-p-methoxybenzyl)-pyrazol-3-yl)ethylene (14.9 g; 0.034 mol) in 300 mL of nitromethane was refluxed for 16 h under nitrogen. The reaction mixture was concentrated in vacuo, the residue was triturated with 400 mL of methanol, ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c(c1)Cc1cccc[n+]1C2 | c1ccc2c(c1)Cc1cccc[n+]1C2 | null | [N+](=O)([O-])C | null | null | c1ccc2c[n+]3ccccc3cc2c1>[N+](=O)([O-])C>c1ccc2c(c1)Cc1cccc[n+]1C2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-890b521151d148d6ac87282c67673b5a | CC(Br)Br.CCOC(=O)c1ccoc1>>CC=C(OCC)c1ccoc1 | C([O-])([O-])=O.[K+].[K+].CN(C)CCN(C)C.O1C=C(C=C1)C(=O)OCC.BrC(C)Br>>O1C=C(C=C1)C(=CC)OCC | Br[CH:2](Br)[CH3:1].O=[C:3]([O:4][CH2:5][CH3:6])[c:7]1[cH:8][cH:9][o:10][cH:11]1>>[CH3:1][CH:2]=[C:3]([O:4][CH2:5][CH3:6])[c:7]1[cH:8][cH:9][o:10][cH:11]1 | CC(Br)Br.CCOC(=O)c1ccoc1 | CC=C(OCC)c1ccoc1 | null | [Zn].Cl[Ti](Cl)(Cl)Cl | C(Cl)Cl.C1CCOC1 | C-C Coupling | OtherReaction | b75b3bce30a6373d339e9987c31d379a4f3d2ed45ea21c78854e952e43da1243 | 5330b04385989beb765aabd8bd463ff2d23c2650a9c6675c8c17037535e79bca | c1ccoc1 | Br-[CH;D3;+0:1](-Br)-[C;D1;H3:2].O=[C;H0;D3;+0:3](-[#8:4]-[C:5])-[c:6]1:[c:7]:[#8;a:8]:[c:9]:[c:10]:1>>[C:5]-[#8:4]-[C;H0;D3;+0:3](=[CH;D2;+0:1]-[C;D1;H3:2])-[c:6]1:[c:7]:[#8;a:8]:[c:9]:[c:10]:1 | 54.3 | [{"value": 54.3, "product": "O1C=C(C=C1)C(=CC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.3, "product": "O1C=C(C=C1)C(=CC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To 300 mL of THF was added with cooling (ice-bath) 300 mL (0.3 mol) of 1M TiCl4 in methylene chloride and the mixture was stirred for 10 min. To the above mixture was added at room temperature 90.5 mL (0.6 mol) of TMEDA, the mixture was stirred for 10 min, and then 44.12 g (0.675 mol) of Zn dust was added with cooling ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ester | Ether | null | null | c1ccoc1 | Br- | [Zn].Cl[Ti](Cl)(Cl)Cl.C(Cl)Cl.C1CCOC1 | null | 0.166667 | CC(Br)Br.CCOC(=O)c1ccoc1>[Zn].Cl[Ti](Cl)(Cl)Cl.C(Cl)Cl.C1CCOC1>CC=C(OCC)c1ccoc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4b6d8583ad144aa1990c4ddd9ecf4d80 | CNOC.O=C(O)c1ccoc1>>CON(C)C(=O)c1ccoc1 | O1C=C(C=C1)C(=O)O.C(C(=O)Cl)(=O)Cl.Cl.CNOC.C(Cl)Cl>>CN(C(=O)C1=COC=C1)OC | [CH3:1][O:2][NH:3][CH3:4].O[C:5](=[O:6])[c:7]1[cH:8][cH:9][o:10][cH:11]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][o:10][cH:11]1 | CNOC.O=C(O)c1ccoc1 | CON(C)C(=O)c1ccoc1 | null | N1=CC=CC=C1.CN(C1=CC=NC=C1)C | N1=CC=CC=C1.C1(=CC=CC=C1)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccoc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#8;a:5]:[c:6]:[c:7]:1.[C;D1;H3:8]-[#8:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:8]-[#8:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#8;a:5]:[c:6]:[c:7]:1 | 88.7 | [{"value": 88.7, "product": "CN(C(=O)C1=COC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "CN(C(=O)C1=COC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of furan-3-carboxylic acid (36 g, 0.32 mol) in 250 mL of toluene was added 49 mL (0.385 mol) of oxalyl chloride and 1 drop of pyridine and the mixture was heated at 80°-90° C. for 1.5 h. The mixture was cooled to room temperature, N,O-dimethylhydroxylamine hydrochloride (35 g, 0.36 mol), 4-dimethylaminopy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccoc1 | HO- | N1=CC=CC=C1.CN(C1=CC=NC=C1)C.N1=CC=CC=C1.C1(=CC=CC=C1)C | null | 2 | CNOC.O=C(O)c1ccoc1>N1=CC=CC=C1.CN(C1=CC=NC=C1)C.N1=CC=CC=C1.C1(=CC=CC=C1)C>CON(C)C(=O)c1ccoc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b81f6bbadd364fcabd341cb169b90406 | Brc1ccoc1.CON(C)C(=O)c1ccoc1>>O=C(c1ccoc1)c1ccoc1 | C(CCC)[Li].BrC1=COC=C1.CN(C(=O)C1=COC=C1)OC>>O1C=C(C=C1)C(=O)C1=COC=C1 | Br[c:3]1[cH:4][cH:5][o:6][cH:7]1.CON(C)[C:2](=[O:1])[c:8]1[cH:9][cH:10][o:11][cH:12]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][o:6][cH:7]1)[c:8]1[cH:9][cH:10][o:11][cH:12]1 | Brc1ccoc1.CON(C)C(=O)c1ccoc1 | O=C(c1ccoc1)c1ccoc1 | null | null | CCOCC | C-C Coupling | OtherReaction | b6253f5511204f961138e67901e3464478ba474fec97457ac8b7f18ef0d3225e | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | O=C(c1ccoc1)c1ccoc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1.C-O-N(-C)-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#8;a:10]:[c:11]:[c:12]:1>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[c:8]1:[c:9]:[#8;a:10]:[c:11]:[c:12]:1)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1 | 78.4 | [{"value": 78.3, "product": "O1C=C(C=C1)C(=O)C1=COC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "O1C=C(C=C1)C(=O)C1=COC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 20 | MINUTE | To a solution of n-butyllithium (2.5M, 28 mL, 0.07 mol) in 150 mL of ether at -78° C. was added a solution of 3-bromofuran (10 g, 0.0628 mol) in 30 mL of ether over a 20 min period and the mixture was stirred at -78° C. for 20 min. To the above mixture was added 3-(N-methyl-N-methoxycarbamoyl)furan (9.16 g, 0.059 mol) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccoc1 | c1ccoc1 | c1ccoc1.c1ccoc1 | HBr | CCOCC | -78 | 0.333333 | Brc1ccoc1.CON(C)C(=O)c1ccoc1>CCOCC>O=C(c1ccoc1)c1ccoc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aa8346898c194446b65096a59802d62f | COc1ccc(CCl)cc1.c1c[nH]nn1>>COc1ccc(Cn2ccnn2)cc1 | [H-].[Na+].N1N=NC=C1.COC1=CC=C(CCl)C=C1>>COC1=CC=C(CN2N=NC=C2)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][cH:13]1.[nH:8]1[cH:9][cH:10][n:11][n:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][cH:10][n:11][n:12]2)[cH:13][cH:14]1 | COc1ccc(CCl)cc1.c1c[nH]nn1 | COc1ccc(Cn2ccnn2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 05c339ca377d2bd6d40ca68d986302f474aa669d3b7616e451ee2557764f991a | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccnn2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]1:[#7;a:6]:[nH;D2;+0:7]:[c:8]:[c:9]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[#7;a:6]:[#7;a:5]:[c:9]:[c:8]:1):[c:4] | 64.5 | [{"value": 64.5, "product": "COC1=CC=C(CN2N=NC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.3, "product": "COC1=CC=C(CN2N=NC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 3.5 g (0.139 mol) of sodium hydride in 120 mL of DMF at 0° C. was added 8 g (0.115 mol) of 1,2,3-triazole in 50 mL of DMF dropwise, and the mixture was allowed to warm to room temperature and stirred for 1 h. The above mixture was cooled to 0° C., and 21.8 g (0.139 mol) of p-methoxybenzyl chloride wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]nn1 | c1c[nH]nn1 | c1ccccc1.c1c[nH]nn1 | HCl | CN(C)C=O | null | 1 | COc1ccc(CCl)cc1.c1c[nH]nn1>CN(C)C=O>COc1ccc(Cn2ccnn2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3f54e9fca67143dcba827aa0a2909574 | CC(C)[Si](C(C)C)(C(C)C)n1cccc1.NC(=O)CCC(=O)NBr>>CC(C)[Si](C(C)C)(C(C)C)n1ccc(Br)c1 | C(C)(C)[Si](N1C=CC=C1)(C(C)C)C(C)C.BrNC(CCC(=O)N)=O>>BrC1=CN(C=C1)[Si](C(C)C)(C(C)C)C(C)C | [CH3:1][CH:2]([CH3:3])[Si:4]([CH:5]([CH3:6])[CH3:7])([CH:8]([CH3:9])[CH3:10])[n:11]1[cH:12][cH:13][cH:14][cH:16]1.NC(=O)CCC(=O)N[Br:15]>>[CH3:1][CH:2]([CH3:3])[Si:4]([CH:5]([CH3:6])[CH3:7])([CH:8]([CH3:9])[CH3:10])[n:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16]1 | CC(C)[Si](C(C)C)(C(C)C)n1cccc1.NC(=O)CCC(=O)NBr | CC(C)[Si](C(C)C)(C(C)C)n1ccc(Br)c1 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | f3f8a432f8a8ea08a5ceb07de68b0f44caf8ff6de6fbb318e6fe4b30105676a4 | f0c47cfd4d5d7957b01579ba4ffee0b3c64b05d7411e52b95a7ea89b926af55c | c1cc[nH]c1 | N-C(=O)-C-C-C(=O)-N-[Br;H0;D1;+0:1].[C:2]-[#14:3](-[C:4])(-[C:5])-[#7;a:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[#7;a:6](-[#14:3](-[C:2])(-[C:4])-[C:5]):[c:10]:1 | 58.6 | [{"value": 58.4, "product": "BrC1=CN(C=C1)[Si](C(C)C)(C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.6, "product": "BrC1=CN(C=C1)[Si](C(C)C)(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 3 | HOUR | To a solution of 1-triisoproylsilyl-pyrrole (13.2 g, 0.059 mol) in 250 mL of THF at -78° C. was added 10.45 g (0.0587 mol) of N-bromosuccinamide (NBS), and the mixture was stirred at -78° C. for 3 h. The reaction mixture was warmed to room temperature and concentrated in vacuo, and the resulting residue in hexane was s... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | Aromatic halide | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HO- | C1CCOC1 | -78 | 3 | CC(C)[Si](C(C)C)(C(C)C)n1cccc1.NC(=O)CCC(=O)NBr>C1CCOC1>CC(C)[Si](C(C)C)(C(C)C)n1ccc(Br)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a24df7fa58b844ecb0722793a52c4932 | O=Cc1ccoc1>>C#CC(O)c1ccoc1 | [Cl-].[NH4+].O1C=C(C=C1)C=O.C(#C)[Mg]Br>>O1C=C(C=C1)C(C#C)O | [CH:3](=[O:4])[c:5]1[cH:6][cH:7][o:8][cH:9]1>>[CH:1]#[C:2][CH:3]([OH:4])[c:5]1[cH:6][cH:7][o:8][cH:9]1 | O=Cc1ccoc1 | C#CC(O)c1ccoc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | eceee5816c0f9c145051e60fc30c4aeafbf642f1679c2474e31812706dbe581d | ce9a178c225fe56fa06be88a01a759294be5f00e5e9f9de154a8b5b2a2cf9c70 | c1ccoc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1>>[C;D1;H1:8]#[C:9]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1 | null | [] | null | null | 1 | HOUR | To 3-furaldehyde (25.0 g, 0.26 mol) in THF (250 mL) at 78° C. was added ethynylmagnesium bromide (572 mL, 0.286, 0.5M THF) at the rate of 10 mL per min. The mixture was slowly warmed to room temperature, stirred for 1 h and then poured into a cooled ammonium chloride solution. The mixture was extracted with ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol.Alkyne | null | null | c1ccoc1 | Other | C1CCOC1 | null | 1 | O=Cc1ccoc1>C1CCOC1>C#CC(O)c1ccoc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-491a1b04b1054004b4485eb8facf8717 | C1CCOC1.CCCCCC.CCOS(=O)(=O)OCC>>C#CC(OCC)c1ccoc1 | C(C)OS(=O)(=O)OCC.CCCCCC.C1CCOC1.[OH-].[Na+]>>O1C=C(C=C1)C(C#C)OCC | [CH2:7]1[CH2:8][CH2:9][O:10][CH2:11]1.CCC[CH2:3][CH2:2][CH3:1].CCOS(=O)(=O)[O:4][CH2:5][CH3:6]>>[CH:1]#[C:2][CH:3]([O:4][CH2:5][CH3:6])[c:7]1[cH:8][cH:9][o:10][cH:11]1 | C1CCOC1.CCCCCC.CCOS(=O)(=O)OCC | C#CC(OCC)c1ccoc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | Aromatic Heterocycle Formation | OtherReaction | 3f873826f4654ad7aaf5a2c17f25114a588aa81b94e0ea75700c5f54fda569d5 | f41dbc21054001785f284181f5c75e4b473563ff691cf0c69f61571efe4b4c56 | c1ccoc1 | C-C-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH3;D1;+0:3].C-C-O-S(=O)(=O)-[O;H0;D2;+0:4]-[C:5]-[C;D1;H3:6].[CH2;D2;+0:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-1>>[C;D1;H3:6]-[C:5]-[O;H0;D2;+0:4]-[CH;D3;+0:1](-[C;H0;D2;+0:2]#[CH;D1;+0:3])-[c;H0;D3;+0:8]1:[cH;D2;+0:7]:[o;H0;D2;+0:11]:[cH;D2;+0:10]:[cH;D2;+0:9... | null | [] | null | null | 3 | HOUR | To a mixture of 1-(3-furyl)-1-hydroxy-2-propane (20.0 g, 0.163 mol), hexane (200 mL) and THF (25 mL) was added tetrabutylammonium bromide (1.05 g, 0.0032 mol), 50% NaOH (150 mL) and then diethylsulfate (30.0g, 0.195 mol) at 0° C. The mixture was stirred for 3 h at room temperature, poured into ice, and extracted with e... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether.Alkyne | C1CCOC1 | c1ccoc1 | c1ccoc1 | HO- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | 3 | C1CCOC1.CCCCCC.CCOS(=O)(=O)OCC>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>C#CC(OCC)c1ccoc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-03291b9b47684e2b99540819df771aca | CC(=O)Oc1cccc2c[n+]3ccccc3cc12>>CCCCc1c2ccccc2cc2cccc[n+]12 | Cl(=O)(=O)(=O)[O-].C(C)(=O)OC1=CC=CC=2C1=CC=1C=CC=C[N+]1C2>>Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2 | O=[C:2](O[c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][n+:18]3[c:13]([cH:12][c:11]21)[cH:14][cH:15][cH:16][cH:17]3)[CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n+:18]12 | CC(=O)Oc1cccc2c[n+]3ccccc3cc12 | CCCCc1c2ccccc2cc2cccc[n+]12 | null | null | O | Miscellaneous | OtherReaction | 99f2775fabdbc5e65bbf6f300dc24c948c9657949e71ca195b75c7b06498ea71 | 28fae2c895dcf8b3c21a52bf83b0739e0fc2e8531ad352ab3d887795d8ac1e21 | c1ccc2c[n+]3ccccc3cc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-O-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[c:7]2:[cH;D2;+0:8]:[#7;a;+:9](:[c:10]):[c:11]:[c:12]:[c:13]:2:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[C:14]-[C:15]-[c;H0;D3;+0:8]1:[#7;a;+:9](:[c:10]):[c:11]:[c:12]:[c:13]2:[cH;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:2:1 | 115.8 | [{"value": 115.8, "product": "Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The above 10-acetoxybenzo[b]quinolizinium perchlorate (3.3 g) was dissolved in 500 mL of water, the solution was boiled, and filtered. To the filtrate was added 100 mL of 30% sodium perchlorate solution and the mixture was chilled. The precipitated solid was isolated by filtration and dried in vacuo to afford 1.9 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | null | O | null | null | CC(=O)Oc1cccc2c[n+]3ccccc3cc12>O>CCCCc1c2ccccc2cc2cccc[n+]12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6384099966cc470f9da8fd1817c1ceaf | COc1ccc(CCl)cc1.c1nc[nH]n1>>COc1ccc(Cn2cncn2)cc1 | [H-].[Na+].N1N=CN=C1.COC1=CC=C(CCl)C=C1>>COC1=CC=C(CN2N=CN=C2)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][cH:13]1.[nH:8]1[cH:9][n:10][cH:11][n:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][n:10][cH:11][n:12]2)[cH:13][cH:14]1 | COc1ccc(CCl)cc1.c1nc[nH]n1 | COc1ccc(Cn2cncn2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9f47013937e839adceb07b7e24945feef9d8519d2c1c97fb8023b4a65c36ed06 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2cncn2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]1:[c:6]:[#7;a:7]:[nH;D2;+0:8]:[c:9]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:9]:1):[c:4] | 79.8 | [{"value": 64.5, "product": "COC1=CC=C(CN2N=CN=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "COC1=CC=C(CN2N=CN=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 4 g (0.16 mol) of sodium hydride in 200 ml of DMF 20 at 0° C. was added 10 g (0.145 mol) of 1,2,4-triazole in 75 ml of DMF dropwise over a period of 30 minutes, and the mixture was allowed to warm to room temperature and stirred for 1 h. The above mixture was cooled to 0° C., 25 g (0.16 mol) of p-met... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nc[nH]n1 | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | HCl | CN(C)C=O | null | 1 | COc1ccc(CCl)cc1.c1nc[nH]n1>CN(C)C=O>COc1ccc(Cn2cncn2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6ce3346cf8114cf58cd9e465b5199dfe | Brc1ccoc1.C#CCO>>OCC#Cc1ccoc1 | BrC1=COC=C1.C(C#C)O>>O1C=C(C=C1)C#CCO | Br[c:5]1[cH:6][cH:7][o:8][cH:9]1.[OH:1][CH2:2][C:3]#[CH:4]>>[OH:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][o:8][cH:9]1 | Brc1ccoc1.C#CCO | OCC#Cc1ccoc1 | null | [Cu]I | null | C-C Coupling | Sonogashira alkyne_aryl halide | 85c427816ae28bd4dbb19650a00c34ca6489eaef6ce7658febdd08dde476e105 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccoc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1.[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1 | null | [] | null | null | null | null | To a mixture of 3-bromofuran (10 g, 0.068 mol) and propargyl alcohol (4.3 ml, 0.074 mol) in 200 ml of TEA was added under argon, CuI (0.26 g, 1.4 mmol) and [(C6H5)3P]2PdCl2 (1.05 g, 1.4 mmol) and the mixture was stirred at 0° C. for 2 hours and at room temperature for 72 hours. The reaction mixture was cooled, decanted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccoc1 | c1ccoc1 | c1ccoc1 | HBr | [Cu]I | null | null | Brc1ccoc1.C#CCO>[Cu]I>OCC#Cc1ccoc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fda4a291a31f49d1ad96851e7bc4285b | CC(=O)OC(C)=O.OCC#Cc1ccoc1>>CC(=O)OCC#Cc1ccoc1 | Cl.O1C=C(C=C1)C#CCO.C(C)(=O)OC(C)=O>>C(C)(=O)OCC#CC1=COC=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][C:6]#[C:7][c:8]1[cH:9][cH:10][o:11][cH:12]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6]#[C:7][c:8]1[cH:9][cH:10][o:11][cH:12]1 | CC(=O)OC(C)=O.OCC#Cc1ccoc1 | CC(=O)OCC#Cc1ccoc1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccoc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8;a:4]:[c:5]:[c:6]-[C:7]#[C:8]-[C:9]-[OH;D1;+0:10]>>[#8;a:4]:[c:5]:[c:6]-[C:7]#[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 74.3 | [{"value": 57.5, "product": "C(C)(=O)OCC#CC1=COC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.3, "product": "C(C)(=O)OCC#CC1=COC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 3-(3-furyl)-2-propynyl alcohol (1.45 g, 0.0118 mol), DMAP (1 mg), TEA (2.46 ml, 0.017 mol), and acetic anhydride (1.6 ml, 0.017 mol) in 25 ml of methylene chloride was stirred for 1 hour and the mixture was poured into cold 1 N HCl solution. The mixture was extracted with ether (3×50 ml), the organic layer... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccoc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 1 | CC(=O)OC(C)=O.OCC#Cc1ccoc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(=O)OCC#Cc1ccoc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-026656cf16884d9aa661211bb77daa46 | COc1ccc[n+]2cc3ccccc3cc12>>CCCCc1c2ccccc2cc2cccc[n+]12 | Cl(=O)(=O)(=O)[O-].COC1=CC=C[N+]=2C=C3C(=CC12)C=CC=C3.O.Cl(=O)(=O)(=O)[O-].[Na+]>>Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2 | O([CH3:1])[c:14]1[c:13]2[cH:12][c:11]3[c:6]([cH:5][n+:18]2[cH:17][cH:16][cH:15]1)[cH:7][cH:8][cH:9][cH:10]3>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n+:18]12 | COc1ccc[n+]2cc3ccccc3cc12 | CCCCc1c2ccccc2cc2cccc[n+]12 | null | null | Br | Miscellaneous | OtherReaction | ebc5d9875058df04f1ba3f72cc8cb765df1dbb969f047be989d32342f3f8bc2c | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | c1ccc2c[n+]3ccccc3cc2c1 | [CH3;D1;+0:1]-O-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[#7;a;+:6]2:[cH;D2;+0:7]:[c:8](:[c:9]):[c:10]:[c:11]:[c:12]:2:1>>[CH3;D1;+0:1]-[C:13]-[C:14]-[C:15]-[c;H0;D3;+0:7]1:[#7;a;+:6]2:[c:5]:[c:4]:[c:3]:[cH;D2;+0:2]:[c:12]:2:[c:11]:[c:10]:[c:8]:1:[c:9] | 156.2 | [{"value": 88.8, "product": "Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 156.2, "product": "Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 1-methoxybenzo[b]quinolizinium perchlorate (1.4 g; 6.1 mmol) in 30 ml of 48% HBr was heated at 100° C. for 16 hour. The reaction mixture was poured into 100 ml of water and 50 ml of sodium perchlorate was added with stirring. The resulting solid was filtered and dried to afford 1.6 g (88.8%) of 1-hydroxybe... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | null | Br | 100 | null | COc1ccc[n+]2cc3ccccc3cc12>Br>CCCCc1c2ccccc2cc2cccc[n+]12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a996c746ecb54471ac6df38e30d8d3e1 | [C-]#N.c1ccc2c[n+]3ccccc3cc2c1>>CCCCc1c2ccccc2cc2cccc[n+]12 | [C-]#N.[K+].[Br-].C1=CC=C[N+]=2C=C3C(=CC12)C=CC=C3.Cl(=O)(=O)(=O)[O-].[Na+]>>Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2 | N#[C-:1].[cH:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n+:18]12>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n+:18]12 | [C-]#N.c1ccc2c[n+]3ccccc3cc2c1 | CCCCc1c2ccccc2cc2cccc[n+]12 | null | null | O.C(C)O.O | C-C Coupling | OtherReaction | 3285131ee597b0d4582360034ea620b84ea2ebf0f2e14aef2ac87fe5ca21ada5 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc2c[n+]3ccccc3cc2c1 | N#[C-;H0;D1:1].[c:2]:[c:3](:[c:4]):[cH;D2;+0:5]:[#7;a;+:6](:[c:7]):[c:8]>>[CH3;D1;+0:1]-[C:9]-[C:10]-[C:11]-[c;H0;D3;+0:5](:[#7;a;+:6](:[c:7]):[c:8]):[c:3](:[c:2]):[c:4] | null | [] | null | null | null | null | A solution of KCN (3g, 0.046 mol) in a minimum of water was added to a solution of benzo[b]quinolizinium bromide (10 g; 0.0385 mol) in 200 ml water. The resulting solid was extracted with an equal volume of methylene chloride. The above organic layer was heated and a solution of bromine (6.4 g) in methylene chloride wa... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | null | O.C(C)O.O | null | null | [C-]#N.c1ccc2c[n+]3ccccc3cc2c1>O.C(C)O.O>CCCCc1c2ccccc2cc2cccc[n+]12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8b317ef19c874f57b5a89bc35fd2943f | CCOC(=O)C(C)(C)CC(=O)O.O=S(Cl)Cl>>CCOC(=O)C(C)(C)CC(=O)Cl | C(C)OC(=O)C(CC(=O)O)(C)C.S(=O)(Cl)Cl>>C(C)OC(=O)C(CC(=O)Cl)(C)C | O[C:10]([CH2:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])=[O:11].O=S(Cl)[Cl:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[CH2:9][C:10](=[O:11])[Cl:12] | CCOC(=O)C(C)(C)CC(=O)O.O=S(Cl)Cl | CCOC(=O)C(C)(C)CC(=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:6](-[#8:7])=[O;D1;H0:8]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | 20 | HOUR | A mixture of 3-ethoxycarbonyl-3,3-dimethylpropionic acid (1 g) and 3 ml of thionyl chloride was stirred at room temperature for 20 hours. The excess thionyl chloride was removed in vacuo to afford 1,1 g of 3-ethoxycarbonyl-3,3-dimethylpropionyl chloride.
Conditions: See reaction.notes.procedure_details.
Workup: The exc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | null | null | 20 | CCOC(=O)C(C)(C)CC(=O)O.O=S(Cl)Cl>>CCOC(=O)C(C)(C)CC(=O)Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a06452d4ab3e4671a5bd9c4e53382385 | CO.O=C(O)c1nccc2ccccc12>>COC(=O)c1nccc2ccccc12 | C1(=NC=CC2=CC=CC=C12)C(=O)O.CO>>COC(=O)C1=NC=CC2=CC=CC=C12 | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | CO.O=C(O)c1nccc2ccccc12 | COC(=O)c1nccc2ccccc12 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc2cnccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 50 | [{"value": 50.0, "product": "COC(=O)C1=NC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-isoquinolinecarboxylic acid (25 g.0.14 mol), 25 g of AMBERLYST®-15 (H+), and 300 ml of methanol was refluxed for 3 days. The reaction mixture was cooled, filtered, and the filtrate was concentrated in vacuo to afford 13.6 g (50%) of 1-isoquinolinecarboxylic acid methyl ester.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | CO.O=C(O)c1nccc2ccccc12>>COC(=O)c1nccc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1ad88c5ca76c4d329b8bf085bdb1345f | COC(=O)c1nccc2ccccc12>>O=Cc1nccc2ccccc12 | COC(=O)C1=NC=CC2=CC=CC=C12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C1(=NC=CC2=CC=CC=C12)C=O | CO[C:2](=[O:1])[c:3]1[n:4][cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12>>[O:1]=[CH:2][c:3]1[n:4][cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | COC(=O)c1nccc2ccccc12 | O=Cc1nccc2ccccc12 | null | null | C1CCOC1 | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccc2cnccc2c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 64 | [{"value": 64.0, "product": "C1(=NC=CC2=CC=CC=C12)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.6, "product": "C1(=NC=CC2=CC=CC=C12)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Isoquinolinecarboxaldehyde (7.3 g, 64 %) was prepared from 1-isoquinolinecarboxylic acid methyl ester (13.6 g, 0.073 mol) and 1M LAH (36.6 ml in THF) in 300 ml of dry THF (J. Org. Chem., vol 28, p 1898, 1963) to afford 7.3 g (64%) of 1-isoquinolinecarboxaldehyde.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccc2cnccc2c1 | HO- | C1CCOC1 | null | null | COC(=O)c1nccc2ccccc12>C1CCOC1>O=Cc1nccc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e72d322566874e22b4fe3d4c4cb4dd39 | O=Cc1nccc2ccccc12.OCCO>>c1ccc2c(C3OCCO3)nccc2c1 | C1(=NC=CC2=CC=CC=C12)C=O.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(OCC1)C1=NC=CC2=CC=CC=C12 | [cH:1]1[cH:2][cH:3][c:4]2[c:5]([CH:6]=[O:7])[n:11][cH:12][cH:13][c:14]2[cH:15]1.O[CH2:8][CH2:9][OH:10]>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([CH:6]3[O:7][CH2:8][CH2:9][O:10]3)[n:11][cH:12][cH:13][c:14]2[cH:15]1 | O=Cc1nccc2ccccc12.OCCO | c1ccc2c(C3OCCO3)nccc2c1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc2c(C3OCCO3)nccc2c1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[c:9]:[#7;a:8]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1):[c:7] | 100.5 | [{"value": 100.5, "product": "O1C(OCC1)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-isoquinolinecarboxaldehyde (7.2 g, 46 mmol), 5.7 g (92 mmol) of ethylene glycol, 200 ml of toluene and 2.3 g (12 mmol) of p-toluenesulfonic acid under argon in a 3 neck-flask equipped with a Dean-Stark Trap was refluxed for 6 h separating the water. The mixture was cooled to room temperature, and poured ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | C1COCO1.c1ccc2cnccc2c1 | HO- | C1(=CC=CC=C1)C | null | null | O=Cc1nccc2ccccc12.OCCO>C1(=CC=CC=C1)C>c1ccc2c(C3OCCO3)nccc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d817cdb898dc4c4791fd3470bd46b871 | Brc1c(COC2CCCCO2)cccc1COC1CCCCO1.O=Cc1ccccn1>>OC(c1ccccn1)c1c(COC2CCCCO2)cccc1COC1CCCCO1 | C1=CC=NC(=C1)C=O.CN(C)CCN(C)C.O1C(CCCC1)OCC1=C(C(=CC=C1)COC1OCCCC1)Br.[Li]CCCC>>N1=C(C=CC=C1)C(O)C1=C(C=CC=C1COC1OCCCC1)COC1OCCCC1 | Br[c:9]1[c:10]([CH2:11][O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:18]2)[cH:19][cH:20][cH:21][c:22]1[CH2:23][O:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][O:30]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][n:8]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][n:8]1)[c:9]1[c:10]([CH2:11][O:12][CH:13]2[CH2:14][CH2:15][C... | Brc1c(COC2CCCCO2)cccc1COC1CCCCO1.O=Cc1ccccn1 | OC(c1ccccn1)c1c(COC2CCCCO2)cccc1COC1CCCCO1 | null | null | CCOCC | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2c(COC3CCCCO3)cccc2COC2CCCCO2)nc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C:3]):[c:4]):[c:5](-[C:6]):[c:7].[O;H0;D1;+0:8]=[CH;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[C:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[CH;D3;+0:9](-[OH;D1;+0:8])-[c:10](:[c:11]):[#7;a:12]:[c:13]):[c:5](-[C:6]):[c:7] | 73 | [{"value": 73.0, "product": "N1=C(C=CC=C1)C(O)C1=C(C=CC=C1COC1OCCCC1)COC1OCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "N1=C(C=CC=C1)C(O)C1=C(C=CC=C1COC1OCCCC1)COC1OCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 2,6-di(tetrahydro-2H-2-pyranyloxymethyl)-phenyl bromide (15.5 g, 39 mmol) in ether at -30° C. was added n-BuLi (2.5M, 16.4 ml, 41 mmol) and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The mixture was cooled to 0° C., and TMEDA (4.56 g, 37 mmol) was added, and the resu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccncc1.C1CCOCC1.c1ccccc1.C1CCOCC1 | Br- | CCOCC | null | 1.5 | Brc1c(COC2CCCCO2)cccc1COC1CCCCO1.O=Cc1ccccn1>CCOCC>OC(c1ccccn1)c1c(COC2CCCCO2)cccc1COC1CCCCO1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-387c94b08c6e47d38076a85d28b4897a | OC(c1ccccn1)c1c(COC2CCCCO2)cccc1COC1CCCCO1>>OCc1cccc(CO)c1C(O)c1ccccn1 | N1=C(C=CC=C1)C(O)C1=C(C=CC=C1COC1OCCCC1)COC1OCCCC1>>N1=C(C=CC=C1)C(O)C1=C(C=CC=C1CO)CO | C1CCC([O:1][CH2:2][c:3]2[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9]C3CCCCO3)[c:10]2[CH:11]([OH:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)OC1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][OH:9])[c:10]1[CH:11]([OH:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1 | OC(c1ccccn1)c1c(COC2CCCCO2)cccc1COC1CCCCO1 | OCc1cccc(CO)c1C(O)c1ccccn1 | null | null | C(C)(=O)O.C1CCOC1.O | Reduction | OtherReaction | d55354815d6f7a64ea8a1f850bd51ba9e291163ec84af74464989e21ec3f9d66 | 12369fed9e6b5d76484a682f4ff2019230b866ab4384925c750ef80e8cdac252 | c1ccc(Cc2ccccn2)cc1 | [c:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[c:4]-[C:5]-[O;H0;D2;+0:6]-C1-C-C-C-C-O-1>>[OH;D1;+0:3]-[C:2]-[c:1].[OH;D1;+0:6]-[C:5]-[c:4] | 43.8 | [{"value": 43.8, "product": "N1=C(C=CC=C1)C(O)C1=C(C=CC=C1CO)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1 g (2.42 mmol) of 1-(2-pyridyl)-1-[2,6-di(tetrahydro-2H-2-pyranyloxymethyl)phenyl]-methanol in 14 ml of acetic acid/THF/water (4:2:1) was heated at 100° C. under nitrogen for 6 hours. The mixture was concentrated in vacuo, the residue was dissolved in ethyl acetate and concentrated in vacuo. The residual... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Primary alcohol.Primary alcohol | C1CCOCC1.C1CCOCC1 | null | c1ccccc1.c1ccncc1 | HO- | C(C)(=O)O.C1CCOC1.O | null | null | OC(c1ccccn1)c1c(COC2CCCCO2)cccc1COC1CCCCO1>C(C)(=O)O.C1CCOC1.O>OCc1cccc(CO)c1C(O)c1ccccn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e24046e8b4f849598eae1352c2006e5b | OCc1cccc(CO)c1C(O)c1ccccn1>>CCCCc1c2ccccc2cc2cccc[n+]12 | N1=C(C=CC=C1)C(O)C1=C(C=CC=C1CO)CO.Cl(=O)(=O)(=O)[O-].[Na+]>>Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2 | O[CH2:1][c:7]1[c:6]([CH:12](O)[c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)[c:11]([CH2:3]O)[cH:10][cH:9][cH:8]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n+:18]12 | OCc1cccc(CO)c1C(O)c1ccccn1 | CCCCc1c2ccccc2cc2cccc[n+]12 | null | null | O=P(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | de93c16343d29e4aa02c02125e95aa1dd3391dde60191777f8eedf76e75d8202 | 6c98e5a80f1c9efa595117e788b54eeaca48c0fac195062be92a50c6d4ed9ee5 | c1ccc2c[n+]3ccccc3cc2c1 | O-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6](-[CH2;D2;+0:7]-O):[c;H0;D3;+0:8]:1-[CH;D3;+0:9](-O)-[c:10](:[c:11]):[n;H0;D2;+0:12]:[c:13]:[c:14]>>[CH3;D1;+0:1]-[C:15]-[CH2;D2;+0:7]-[C:16]-[c:17]1:[c;H0;D3;+0:8]2:[cH;D2;+0:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:2:[cH;D2;+0:9]:[c:10](:[c:11]):[n+;H0;D3:12]... | null | [] | null | null | null | null | A mixture of 0.6 g (2.5 mmol) of 1-(2-pyridyl)-1-[2,6-di(hydroxymethyl)-phenyl]methanol and 10 ml of POCl3 was refluxed with 30 stirring for 4 hours. The mixture was cooled, poured onto ice, stirred and treated with a 20% sodium perchlorate solution. The resulting mixture was filtered, the resulting solid was washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Secondary alcohol | null | c1ccccc1.c1ccncc1 | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | null | O=P(Cl)(Cl)Cl | null | null | OCc1cccc(CO)c1C(O)c1ccccn1>O=P(Cl)(Cl)Cl>CCCCc1c2ccccc2cc2cccc[n+]12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fee2b76fa72f4ff9b4a4d85aa6743379 | COC(=O)c1ccc(C)c(N)c1>>COC(=O)c1ccc2cn[nH]c2c1 | COC(C1=CC(=C(C=C1)C)N)=O.N(=O)[O-].[Na+]>>N1N=CC2=CC=C(C=C12)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:12]([NH2:11])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][n:10][nH:11][c:12]2[cH:13]1 | COC(=O)c1ccc(C)c(N)c1 | COC(=O)c1ccc2cn[nH]c2c1 | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9194288567782b9a53b0fcc5af5659b26356b37141f27aaae557b9a5c0e3b9e0 | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccc2[nH]ncc2c1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6]>>[c:6]:[c:4]1:[nH;D2;+0:5]:[#7;a:7]:[cH;D2;+0:1]:[c:2]:1:[c:3] | 71.9 | [{"value": 71.6, "product": "N1N=CC2=CC=C(C=C12)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.9, "product": "N1N=CC2=CC=C(C=C12)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 3-amino-4-methylbenzoic acid methyl ester (25 g, 0.15 mol) in 1 L of acetic acid cooled to 0° C. was added a solution of NaNO2 (12.5 g, 0.182 mol) in 50 ml of water and the mixture was warmed to room temperature with stirring over 4 hours. The solution was concentrated in vacuo, the residue was tritura... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | Other | O.C(C)(=O)O | null | 4 | COC(=O)c1ccc(C)c(N)c1>O.C(C)(=O)O>COC(=O)c1ccc2cn[nH]c2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0aea872a6936492d87a04dfedfb85e49 | CI.Cc1ccc(Cl)c(O)c1>>COc1cc(C)ccc1Cl | OC=1C=C(C=CC1Cl)C.C([O-])([O-])=O.[K+].[K+].CI>>COC=1C=C(C=CC1Cl)C | I[CH3:1].[OH:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[Cl:10] | CI.Cc1ccc(Cl)c(O)c1 | COc1cc(C)ccc1Cl | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 93.4 | [{"value": 93.4, "product": "COC=1C=C(C=CC1Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 3-hydroxy-4-chlorotoluene (25 g, 0.175 mol) in 400 ml of acetone was added 30.11 g (0.22 mol) of milled potassium carbonate and 31.22 g (0.22 mol) of methyl iodide, and the mixture was refluxed with stirring for 16 hours. The mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | CC(=O)C | null | 16 | CI.Cc1ccc(Cl)c(O)c1>CC(=O)C>COc1cc(C)ccc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2be1e6306c5d4e08a0d4bf6dc738737d | COc1cc(C(=O)O)ccc1Cl>>COc1cc(CO)ccc1Cl | B.C1CCOC1.COC=1C=C(C(=O)O)C=CC1Cl>>COC=1C=C(C=CC1Cl)CO | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([Cl:11])[cH:9][cH:8]1)[OH:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][cH:9][c:10]1[Cl:11] | COc1cc(C(=O)O)ccc1Cl | COc1cc(CO)ccc1Cl | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 91.1 | [{"value": 90.0, "product": "COC=1C=C(C=CC1Cl)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "COC=1C=C(C=CC1Cl)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To 30.6 ml of BH3.THF was added a solution of 3-methoxy-4-chlorobenzoic acid (35 g, 0.187 mol) in 450 ml of THF, and the mixture was refluxed with stirring under argon for 3 hours. The mixture was quenched 25 with THF/water (1:1,300 ml), concentrated in vacuo, and the residue was partitioned between methylene chloride/... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | null | 3 | COc1cc(C(=O)O)ccc1Cl>C1CCOC1>COc1cc(CO)ccc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-424594ac1c044b53938437c9aaf9f4c4 | COc1c(Cl)ccc2c[n+]3ccccc3cc12>>CCCCc1c2ccccc2cc2cccc[n+]12 | Cl(=O)(=O)(=O)[O-].ClC=1C=CC=2C(=CC=3C=CC=C[N+]3C2)C1OC>>Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2 | Cl[c:9]1[c:2](O[CH3:1])[c:11]2[c:6]([cH:5][n+:18]3[c:13]([cH:12]2)[cH:14][cH:15][cH:16][cH:17]3)[cH:7][cH:8]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n+:18]12 | COc1c(Cl)ccc2c[n+]3ccccc3cc12 | CCCCc1c2ccccc2cc2cccc[n+]12 | null | null | Br | Miscellaneous | OtherReaction | 3177d18575f824db6a18db7ccac580de1b41fb8334f450736d0cd46e792b9b34 | 80083ded544d02db894571ce654dd57555ca45a58f858fdf0ed3a262453c36e3 | c1ccc2c[n+]3ccccc3cc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[cH;D2;+0:5]:[#7;a;+:6](:[c:7]):[c:8](:[c:9]):[c:10]:[c;H0;D3;+0:11]:2:[c;H0;D3;+0:12]:1-O-[CH3;D1;+0:13]>>[CH3;D1;+0:13]-[CH2;D2;+0:12]-[C:14]-[C:15]-[c;H0;D3;+0:5]1:[#7;a;+:6](:[c:7]):[c:8](:[c:9]):[c:10]:[c;H0;D3;+0:11]2:[c:16]:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:2:1 | 152.6 | [{"value": 79.0, "product": "Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 152.6, "product": "Cl(=O)(=O)(=O)[O-].C(CCC)C1=C2C(=CC=3C=CC=C[N+]13)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A reaction mixture containing 9-chloro-10-methoxybenzo[b]quinolizinium perchlorate (5 g; 14.83 mmol) and 48% HBr (50 ml) was refluxed with stirring for 18 hours. The mixture was concentrated in vacuo, the residue was redissolved in water, filtered, and the filtrate was treated with a sodium perchlorate solution with st... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | null | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | c1ccc2c[n+]3ccccc3cc2c1 | null | Br | null | 18 | COc1c(Cl)ccc2c[n+]3ccccc3cc12>Br>CCCCc1c2ccccc2cc2cccc[n+]12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d5f647c0f6554e4d83d12e046e00e776 | Oc1cc2cc3cccc[n+]3cc2cc1Cl>>c1cc[n+]2ccccc2c1 | Cl(=O)(=O)(=O)[O-].ClC1=CC=2C(=CC=3C=CC=C[N+]3C2)C=C1O.O1C=C(C=C1)C(=C)C1=COC=C1>>Cl(=O)(=O)(=O)[O-].C1=CC=C[N+]2=CC=CC=C12 | Oc1c[c:12]2[c:11](cc1Cl)[cH:10][n+:9]1[cH:8][cH:7][cH:6][cH:15][c:14]1[cH:13]2>>[cH:6]1[cH:7][cH:8][n+:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1 | Oc1cc2cc3cccc[n+]3cc2cc1Cl | c1cc[n+]2ccccc2c1 | null | null | C(C)#N | Reduction | OtherReaction | 4a490ae2d40c8a22c4fbd0dfcd99c73ac62674f1773cc3df9de17c12d26c6f71 | 00acf62c1ee6c127a512fc4aef1d1ace4643d23c07024023ca84c70c1c95b724 | c1cc[n+]2ccccc2c1 | Cl-c1:c:[c;H0;D3;+0:1]2:[c:2]:[#7;a;+:3](:[c:4]):[c:5](:[c:6]):[c:7]:[c;H0;D3;+0:8]:2:c:c:1-O>>[c:6]:[c:5]1:[c:7]:[cH;D2;+0:8]:[cH;D2;+0:1]:[c:2]:[#7;a;+:3]:1:[c:4] | null | [] | null | null | 6 | HOUR | A reaction mixture containing 8-chloro-9-hydroxybenzo[b]quinolizinium perchlorate (3.3 g; 10 mmol) and 1,1-di(3-furyl)ethylene (1.76 g, 11 mmol) in 50 ml of acetonitrile was allowed to reflux under nitrogen with stirring for 6 hours. The reaction mixture was concentrated in vacuo and the residue was crystallized from m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | null | c1ccc2c[n+]3ccccc3cc2c1 | c1cc[n+]2ccccc2c1 | c1cc[n+]2ccccc2c1 | HCl | C(C)#N | null | 6 | Oc1cc2cc3cccc[n+]3cc2cc1Cl>C(C)#N>c1cc[n+]2ccccc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1864db37366949a8ae45eeee9714f568 | COC(=O)c1cc2ccccc2cn1>>O=Cc1cc2ccccc2cn1 | COC(=O)C=1N=CC2=CC=CC=C2C1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C1=NC(=CC2=CC=CC=C12)C=O | CO[C:2](=[O:1])[c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11][n:12]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11][n:12]1 | COC(=O)c1cc2ccccc2cn1 | O=Cc1cc2ccccc2cn1 | null | null | C1CCOC1 | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccc2cnccc2c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 85.7 | [{"value": 84.0, "product": "C1=NC(=CC2=CC=CC=C12)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.7, "product": "C1=NC(=CC2=CC=CC=C12)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Isoquinolinecarboxaldehyde (7 g, 84%) was prepared by reduction of 3-isoquinolinecarboxylic acid methyl ester (10 g, 52 mmol) with 1M LAH (27 ml in THF,27 mmol) in 300 ml of dry THF at -78° C. for 30 minutes. The mixture was quenched with 7 ml of acetic acid, concentrated in vacuo, and the residue was purified by sil... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccc2cnccc2c1 | HO- | C1CCOC1 | null | null | COC(=O)c1cc2ccccc2cn1>C1CCOC1>O=Cc1cc2ccccc2cn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ba96baec63e2477e9126cc3d3a5c07f5 | O=Cc1cc2ccccc2cn1.OCCO>>c1ccc2cc(C3OCCO3)ncc2c1 | C1=NC(=CC2=CC=CC=C12)C=O.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O1C(OCC1)C=1N=CC2=CC=CC=C2C1 | [cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]([CH:7]=[O:8])[n:12][cH:13][c:14]2[cH:15]1.O[CH2:9][CH2:10][OH:11]>>[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]([CH:7]3[O:8][CH2:9][CH2:10][O:11]3)[n:12][cH:13][c:14]2[cH:15]1 | O=Cc1cc2ccccc2cn1.OCCO | c1ccc2cc(C3OCCO3)ncc2c1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc2cc(C3OCCO3)ncc2c1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[c:9]:[#7;a:8]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1):[c:7] | 89.9 | [{"value": 89.9, "product": "O1C(OCC1)C=1N=CC2=CC=CC=C2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "O1C(OCC1)C=1N=CC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-isoquinolinecarboxaldehyde (7 g, 44.5 mmol), 5.5 g (88 mmol) of ethylene glycol, 400 ml of toluene and 1.1 g (4.4 mmol) of p-toluenesulfonic acid was refluxed for 16 h while separating the water formed. The mixture was cooled to room temperature and washed with sodium bicarbonate solution, water, and bri... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccc2cnccc2c1.C1COCO1 | HO- | C1(=CC=CC=C1)C | null | null | O=Cc1cc2ccccc2cn1.OCCO>C1(=CC=CC=C1)C>c1ccc2cc(C3OCCO3)ncc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0757477bf28d448db4c5e894a5ea97c1 | CCCCCCCCO.O=C(Br)CBr>>CCCCCCCCOC(=O)CBr | BrCC(=O)Br.C(CCCCCCC)O.N1=CC=CC=C1>>BrCC(=O)OCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].Br[C:10](=[O:11])[CH2:12][Br:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[CH2:12][Br:13] | CCCCCCCCO.O=C(Br)CBr | CCCCCCCCOC(=O)CBr | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | null | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C:5] | 24.1 | [{"value": 24.1, "product": "BrCC(=O)OCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Bromoacetyl bromide (20 g, 99.1 mmol) was added to a solution of 1-octanol (12.9 g, 99.1 mmol) and 10 ml of pyridine in 100 ml of methylene chloride at 0° C. After 10 minutes, the mixture was quenched with 100 ml of ice/water, and the aqueous layer was extracted with methylene chloride, and the combined organic layer w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | null | HBr | C(Cl)Cl | null | 0.166667 | CCCCCCCCO.O=C(Br)CBr>C(Cl)Cl>CCCCCCCCOC(=O)CBr |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-792d9e5904e149f68154f932fa6d2ce2 | CC(C)C(=O)O.CCCCCCCCOC(=O)CBr.CN(C)P(=O)(N(C)C)N(C)C>>CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)O | C(C(C)C)(=O)O.C(C)(C)[N-]C(C)C.[Li+].C(C)(C)NC(C)C.[Li]CCCC.BrCC(=O)OCCCCCCCC.CN(C)P(=O)(N(C)C)N(C)C>>C(CCCCCCC)OC(=O)C(C(C(=O)O)(C)C)C | [CH:14]([CH3:15])([CH3:16])[C:17](=[O:18])[OH:19].Br[CH2:12][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11].CN(C)P(=O)(N(C)C)N(C)[CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[CH:12]([CH3:13])[C:14]([CH3:15])([CH3:16])[C:17](=[O:18])[OH:19] | CC(C)C(=O)O.CCCCCCCCOC(=O)CBr.CN(C)P(=O)(N(C)C)N(C)C | CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | d841351e32f03fa351b4752ba248e792eea3b05d10b194e1f2052626c1dc4283 | c8d0ace6c092b333e4fa699bb753afeb889070a86fd0de61e6d5288d99558a57 | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-N(-C)-P(=O)(-N(-C)-C)-N(-C)-[CH3;D1;+0:6].[C;D1;H3:7]-[CH;D3;+0:8](-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[CH3;D1;+0:6])-[C;H0;D4;+0:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[O;D1;H1:12] | 12.3 | [{"value": 12.3, "product": "C(CCCCCCC)OC(=O)C(C(C(=O)O)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | To a mixture of lithium diisopropylamide (prepared from 4.8 g, (47.8 mmol) of diisopropylamine and 19.1 ml, (2.5M, 47.8 mmol) of n-BuLi) in 50 ml of THF was added isobutyric acid (2.2 ml, 23.9 mmol) at 0° C. and the mixture was allowed to warm to 45° C. with stirring. To the mixture cooled to -78° C., was added 4.3 g (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Tertiary amine.Tertiary amine.Tertiary amine | Ester | null | null | null | HBr | C1CCOC1 | 45 | null | CC(C)C(=O)O.CCCCCCCCOC(=O)CBr.CN(C)P(=O)(N(C)C)N(C)C>C1CCOC1>CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6956540df8cc4043ada703c4bf8c5ec1 | CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)O.O=S(Cl)Cl>>CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)Cl | C(CCCCCCC)OC(=O)C(C(C(=O)O)(C)C)C.S(=O)(Cl)Cl>>C(CCCCCCC)OC(=O)C(C(C(=O)Cl)(C)C)C | O[C:17]([C:14]([CH:12]([C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11])[CH3:13])([CH3:15])[CH3:16])=[O:18].O=S(Cl)[Cl:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10](=[O:11])[CH:12]([CH3:13])[C:14]([CH3:15])([CH3:16])[C:17](=[O:18])[Cl:19] | CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)O.O=S(Cl)Cl | CCCCCCCCOC(=O)C(C)C(C)(C)C(=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;D1;H3:5])(-[C;D1;H3:6])-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | 3-(1-Octyloxycarbonyl)-2,2-dimethylbutyric acid (0.4 g) was treated with thionyl chloride (20 ml) and the excess thionyl chloride was removed in vacuo to afford 0.33 g of 3-(1-octyloxycarbonyl)-2,2-dimethylbutyric acid chloride.
Conditions: See reaction.notes.procedure_details.
Workup: the excess thionyl chloride was r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | null | null | null | CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)O.O=S(Cl)Cl>>CCCCCCCCOC(=O)C(C)C(C)(C)C(=O)Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f04b1eaf04fb4dce92f8799d2cdb1db8 | CC(=O)CCc1ccc(OCc2ccccc2)cc1.Cl.N>>CC([NH3+])CCc1ccc(OCc2ccccc2)cc1.[Cl-] | C(C1=CC=CC=C1)OC1=CC=C(C=C1)CCC(=O)C.N.Cl>>[Cl-].CC(CCC1=CC=C(C=C1)OCC1=CC=CC=C1)[NH3+] | O=[C:2]([CH3:1])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1.[ClH:20].[NH3:3]>>[CH3:1][CH:2]([NH3+:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1.[Cl-:20] | CC(=O)CCc1ccc(OCc2ccccc2)cc1.Cl.N | CC([NH3+])CCc1ccc(OCc2ccccc2)cc1.[Cl-] | null | [Ni] | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 0e565144b759285fc4001485318c08d7fdafb328470199718d930bb43326e691 | 150a254dd88f1deb9794fe82c75c17a8f7dc6e37ef5fe402d4d271ea53a55f02 | c1ccc(COc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[ClH;D0;+0:5].[NH3;D0;+0:6]>>[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH3+;D1:6].[Cl-;H0;D0:5] | null | [] | null | null | 2 | HOUR | A solution of 40.0 g of methyl 2-(4-benzyloxyphenyl)ethyl ketone and 160 ml of anhydrous ammonia in 300 ml of ethanol was heated at 75° C. and stirred for two hours. After cooling the reaction mixture to room temperature, 4.0 g of Raney nickel was added in one portion, and the reaction mixture then was stirred at 25° C... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1.c1ccccc1 | Other | [Ni].C(C)O | null | 2 | CC(=O)CCc1ccc(OCc2ccccc2)cc1.Cl.N>[Ni].C(C)O>CC([NH3+])CCc1ccc(OCc2ccccc2)cc1.[Cl-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cbb806ea98e64dc89b3cf63cd5aec498 | CC(N)CCc1ccc(OCc2ccccc2)cc1.O=C(Oc1ccc(C(O)C(=O)O)cc1)c1ccccc1>>CC(CCc1ccc(OCc2ccccc2)cc1)NC(=O)C(O)c1ccc(OCc2ccccc2)cc1 | C(C1=CC=CC=C1)(=O)OC1=CC=C(C(C(=O)O)O)C=C1.CC(CCC1=CC=C(C=C1)OCC1=CC=CC=C1)N.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(C(NC(CCC1=CC=C(C=C1)OCC1=CC=CC=C1)C)=O)O | [CH3:1][CH:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1)[NH2:19].O=[C:29]([O:28][c:27]1[cH:26][cH:25][c:24]([CH:22]([C:20](O)=[O:21])[OH:23])[cH:37][cH:36]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][CH:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:... | CC(N)CCc1ccc(OCc2ccccc2)cc1.O=C(Oc1ccc(C(O)C(=O)O)cc1)c1ccccc1 | CC(CCc1ccc(OCc2ccccc2)cc1)NC(=O)C(O)c1ccc(OCc2ccccc2)cc1 | null | null | null | Acylation | OtherReaction | 344cb8682157e909550dc80a6959e17d802e8a262d79ed544925031a997fda5c | cfaed6d41dcaf720ed77c4966e5a454532fca2474a59d27ec50e08496706380a | O=C(Cc1ccc(OCc2ccccc2)cc1)NCCCc1ccc(OCc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[O;D1;H1:4])-[c:5].O=[C;H0;D3;+0:6](-[#8:7]-[c:8])-[c:9](:[c:10]):[c:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH2;D1;+0:15]>>[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[O;D1;H1:4])-[c:5].[c:8]-[#8:7]-[CH2;D2;+0:6]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | As pointed out above, a preferred embodiment of this invention employs a mixture of all four optica isomers of the compound of Example 7. This racemic mixture can be prepared by the method described above by reaction of dl-4-(benzoyloxy)mandelic acid with dl-1-methyl-3-(4-benzyloxyphenyl)propylamine in the presence of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine | Ether.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(N)CCc1ccc(OCc2ccccc2)cc1.O=C(Oc1ccc(C(O)C(=O)O)cc1)c1ccccc1>>CC(CCc1ccc(OCc2ccccc2)cc1)NC(=O)C(O)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-662ab25bd1194f68a20d32f2372b72ac | [Na+]>>[Na+] | [Na+].COC1=CC=C(OC(C(=O)[O-])C)C=C1.N[C@@H](CCC(=O)O)C(=O)[O-].[K+]>>N[C@@H](CCC(=O)O)C(=O)[O-].[Na+] | [Na+:11]>>[Na+:11] | [Na+] | [Na+] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | Addition of 0.5% by weight of (-)-2-(4-methoxyphenoxy)propionic acid sodium salt to monopotassium glutamate produced a flavor almost identical to monosodium glutamate. Virtually no bitter taste was detectable.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | [Na+]>>[Na+] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b5fb1dd9ab56411ebfb21a50f3743df7 | [Na+]>>[Na+] | [Na+].COC1=CC=C(OC(C(=O)[O-])C)C=C1.N[C@@H](CCC(=O)O)C(=O)[O-].[K+]>>N[C@@H](CCC(=O)O)C(=O)[O-].[Na+] | [Na+:11]>>[Na+:11] | [Na+] | [Na+] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | Addition of 0.5% by weight of (-)-2-(4-methoxyphenoxy)propionic acid sodium salt to monopotassium glutamate produced a flavor almost identical to monosodium glutamate. Virtually no bitter taste was detectable.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | [Na+]>>[Na+] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-74576cc0cdeb45d39886fb8cdd6bf5f5 | [Na+]>>[Na+] | [Na+].COC1=CC=C(OC(C(=O)[O-])C)C=C1.N[C@@H](CCC(=O)O)C(=O)[O-].[K+]>>N[C@@H](CCC(=O)O)C(=O)[O-].[Na+] | [Na+:11]>>[Na+:11] | [Na+] | [Na+] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | Addition of 0.5% by weight of (-)-2-(4-methoxyphenoxy)propionic acid sodium salt to monopotassium glutamate produced a flavor almost identical to monosodium glutamate. Virtually no bitter taste was detectable.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | [Na+]>>[Na+] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-90959db5947a4258a73a1e63948f6255 | COC(=O)c1cccc(O)c1.O=C1C2CC3CC(C2)CC1C3>>Oc1cccc(COC=C2C3CC4CC(C3)CC2C4)c1 | OC=1C=C(C(=O)OC)C=CC1.C12C(C3CC(CC(C1)C3)C2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)N(CC)CC>>OC=1C=C(C=CC1)COC=C1C2CC3CC(CC1C3)C2 | O=[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([OH:1])[cH:20]1)[O:8][CH3:9].O=[C:10]1[CH:11]2[CH2:12][CH:13]3[CH2:14][CH:15]([CH2:16]2)[CH2:17][CH:18]1[CH2:19]3>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][CH:9]=[C:10]2[CH:11]3[CH2:12][CH:13]4[CH2:14][CH:15]([CH2:16]3)[CH2:17][CH:18]2[CH2:19]4)[cH:20]1 | COC(=O)c1cccc(O)c1.O=C1C2CC3CC(C2)CC1C3 | Oc1cccc(COC=C2C3CC4CC(C3)CC2C4)c1 | null | null | O.C1CCOC1 | C-C Coupling | OtherReaction | 389106083e04f8e6df8f0c9260f1407d6bf5c54e09b67603de76eae196869798 | 52f6d3ebf2f24b4710cebf4125f6a3882be46cd0b71cef8accd7c6ff101eaf88 | C(OCc1ccccc1)=C1C2CC3CC(C2)CC1C3 | O=[C;H0;D3;+0:1](-[#8:2]-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6].O=[C;H0;D3;+0:7](-[C:8](-[C:9])-[C:10])-[C:11](-[C:12])-[C:13]>>[C:9]-[C:8](-[C:10])-[C;H0;D3;+0:7](=[CH;D2;+0:3]-[#8:2]-[CH2;D2;+0:1]-[c:4](:[c:5]):[c:6])-[C:11](-[C:12])-[C:13] | 89 | [{"value": 89.0, "product": "OC=1C=C(C=CC1)COC=C1C2CC3CC(CC1C3)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "OC=1C=C(C=CC1)COC=C1C2CC3CC(CC1C3)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | [(3-Hydroxyphenyl)methoxymethylene]adamantane (1a) was prepared as described in my previous application Serial No. 224,681, filed Jul. 27, 1988. A 500-mL flask was fitted with a reflux condenser, a 125-mL addition funnel, and nitrogen line. The apparatus was dried by means of a hot air gun and nitrogen purging. Dry THF... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ether | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | c1ccccc1.C1C2CC3CC1CC(C2)C3 | Other | O.C1CCOC1 | null | 0.25 | COC(=O)c1cccc(O)c1.O=C1C2CC3CC(C2)CC1C3>O.C1CCOC1>Oc1cccc(COC=C2C3CC4CC(C3)CC2C4)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7fa72a964a72422f852d7a22402421fe | CCCCCCCCCCCCCCCCC(OC(C)=O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC>>CCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC | [OH-].[Na+].C(C)(=O)OC(C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC.[OH-].[Na+]>>OC(C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC | CC(=O)[O:18][CH: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])[C:19](=[O:20])[NH:21][C@@H:22]([CH2:23][OH:24])[C@H:25]([OH:26])[C@H:27]([OH:28])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C... | CCCCCCCCCCCCCCCCC(OC(C)=O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC | CCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC | null | null | C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | null | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7] | null | [] | null | null | 1.5 | HOUR | A mixture of 35.62 grams (55.4 mmoles) of N-(2-acetoxy-octadecanoyl) phytosphingosine, 250 ml of 96% ethanol and 20 ml of 6.18M sodium hydroxide is stirred for 1.5 hours. An additional 5 ml of 6.18M sodium hydroxide is added and the stirring continued for 1 hour.
Conditions: See reaction.notes.procedure_details.
Workup... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | null | HO- | C(C)O | null | 1.5 | CCCCCCCCCCCCCCCCC(OC(C)=O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC>C(C)O>CCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5e431815bfc34fb79e4253adb29aeeb3 | CCCCCCCCCCCCCCCCCCCCCCC(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)C(=O)OC(C)=O>>CCCCCCCCCCCCCCCCCCCCCCC(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)C(=O)O | [OH-].[Na+].C(C)(=O)OC(C(CCCCCCCCCCCCCCCCCCCCCC)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)=O.[OH-].[Na+]>>OC(C(CCCCCCCCCCCCCCCCCCCCCC)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)=O | CC(=O)[O:48][C:46]([CH:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][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])[NH:24][C@@H:25]([CH2:26][OH:27])[C@H:28]([OH:29])[C@H:30]([OH:31])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C... | CCCCCCCCCCCCCCCCCCCCCCC(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)C(=O)OC(C)=O | CCCCCCCCCCCCCCCCCCCCCCC(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)C(=O)O | null | null | C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 18e1e61321ff01ec602ee6e196a485c543be50cc909a3dcf6656e78df2b0c8a3 | 142e3062b491bdf723a1cbf11092ef8608063f50d7ab4a919f898a356546f037 | null | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 1.5 | HOUR | Sodium hydroxide (0.08 ml, 6.18M) is added to a stirred solution of 58 mg of N-(α-acetoxy-tetracosanoyl) phytosphingosine in 3 ml of 96% ethanol. After 1.5 hours, additional 6.18M sodium hydroxide (0.05 ml) is added and stirring is continued for 0.5 hour.
Conditions: See reaction.notes.procedure_details.
Workup: is con... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid | null | null | null | HO- | C(C)O | null | 1.5 | CCCCCCCCCCCCCCCCCCCCCCC(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)C(=O)OC(C)=O>C(C)O>CCCCCCCCCCCCCCCCCCCCCCC(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6b6e2b7980b642d68dd1b77edd6c47e4 | O=C(O)c1ccc(B(O)O)cc1.O=C1CCC(=O)N1O>>O=C(ON1C(=O)CCC1=O)c1ccc(B(O)O)cc1 | C1(CCCCC1)N=C=NC1CCCCC1.C(=O)(O)C1=CC=C(C=C1)B(O)O.ON1C(CCC1=O)=O.ClCCl>>C1(CCC(N1OC(=O)C1=CC=C(C=C1)B(O)O)=O)=O | O[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([B:15]([OH:16])[OH:17])[cH:18][cH:19]1.[OH:3][N:4]1[C:5](=[O:6])[CH2:7][CH2:8][C:9]1=[O:10]>>[O:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[CH2:7][CH2:8][C:9]1=[O:10])[c:11]1[cH:12][cH:13][c:14]([B:15]([OH:16])[OH:17])[cH:18][cH:19]1 | O=C(O)c1ccc(B(O)O)cc1.O=C1CCC(=O)N1O | O=C(ON1C(=O)CCC1=O)c1ccc(B(O)O)cc1 | null | null | CN(C)C=O | Protection | OtherReaction | a1b3ee4184fc00a0730e4c14eca3a5fbe87fccb44744074c13ef1bfbfabde8ad | e66168e1cfeb6611d93ee4c49193aae81e56c700a9fe46743dc42eed291ed0f9 | O=C(ON1C(=O)CCC1=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1-[OH;D1;+0:13]>>[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 10 | MINUTE | 4-Carboxyphenyl-boronic acid (CPBA, Example 1, 0.25 g, 1.51 mmol) and N-hydroxysuccinimide (0.26 g, 2.26 mmol) were dissolved in 8.5 ml DMF using a magnetic stirrer. 20 ml of dichloromethane (CH2Cl2) was then added, and the solution was stirred for 10 minutes. N,N'-dicyclohexyl-carbodiimide (DCC, 0.93 g, 4.52 mmol) in ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1CC[NH]C1.c1ccccc1 | HO- | CN(C)C=O | null | 0.166667 | O=C(O)c1ccc(B(O)O)cc1.O=C1CCC(=O)N1O>CN(C)C=O>O=C(ON1C(=O)CCC1=O)c1ccc(B(O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-07f496de1bd0491e8be710dd1d24e21a | COc1ccc(N)cc1.c1ccc2c(c1)Nc1ccccc1S2>>COc1ccc(NC2C=CC3=Nc4ccccc4SC3=C2)cc1 | C1=CC=CC=2SC3=CC=CC=C3NC12.C1=CC=CC=2SC3=CC=CC=C3NC12.COC1=CC=C(C=C1)N.I(=O)(=O)(=O)O.O>>COC1=CC=C(C=C1)NC1C=CC2=NC3=CC=CC=C3SC2=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:22][cH:23]1.[cH:8]1[cH:9][cH:10][c:11]2[c:20]([cH:21]1)[S:19][c:18]1[c:13]([cH:14][cH:15][cH:16][cH:17]1)[NH:12]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]2[CH:9]=[CH:10][C:11]3=[N:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[S:19][C:20]3=[CH:21]2)[cH:22][cH:23]1 | COc1ccc(N)cc1.c1ccc2c(c1)Nc1ccccc1S2 | COc1ccc(NC2C=CC3=Nc4ccccc4SC3=C2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 6930dee6fed16270a98a17affa303d48c6d1a23c1b7ce83a8f96734b9c689844 | 135d6726372d55ea8e2468fa41946626334f79bb40cbea88b6316de909b8cb14 | C1=CC(Nc2ccccc2)C=C2Sc3ccccc3N=C12 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]-[#16:8]-[c;H0;D3;+0:9]2:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14]:2-[NH;D2;+0:15]-1>>[c:5]:[c:6]1:[c:7]-[#16:8]-[C;H0;D3;+0:9]2=[CH;D2;+0:10]-[CH;D3;+0:11](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[CH;D2;+0:12]=[CH;D2;+0:13]-[C;H0;D3;+0:14]-2=... | null | [] | null | null | null | null | Phenothiazine, 0.5 g/0.0025M, and p-anisidine, 0.307 g/0.0025M, were dissolved in 50 ml of methanol and stirred at ambient temperature. Periodic acid, 3.4 g/0.015M, was dissolved in 40 ml of methanol and the solution added in one portion to the stirring phenothiazine mixture. The reaction mixture was stirred for 20 min... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Monosulfide | Substituted imine.Secondary amine.Monosulfide | c1ccc2c(c1)Nc1ccccc1S2 | C1=CC2=Nc3ccccc3SC2=CC1 | c1ccccc1.C1=CC2=Nc3ccccc3SC2=CC1 | null | CO | null | null | COc1ccc(N)cc1.c1ccc2c(c1)Nc1ccccc1S2>CO>COc1ccc(NC2C=CC3=Nc4ccccc4SC3=C2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-84944dda715e4fbebd2a94e48004d0ca | O=C(CN1CCN(Cc2ccccc2)CCN(Cc2ccccc2)CCN(Cc2ccccc2)CC1)NCCOCCOCCNC(=O)CN1CCN(Cc2ccccc2)CCN(Cc2ccccc2)CCN(Cc2ccccc2)CC1>>O=C(CN1CCNCCNCCNCC1)NCCOCCOCCNC(=O)CN1CCNCCNCCNCC1 | C(C1=CC=CC=C1)N1CCN(CCN(CCN(CC1)CC1=CC=CC=C1)CC1=CC=CC=C1)CC(NCCOCCOCCNC(CN1CCN(CCN(CCN(CC1)CC1=CC=CC=C1)CC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O.[H][H]>>N1(CCNCCNCCNCC1)CC(NCCOCCOCCNC(CN1CCNCCNCCNCC1)=O)=O | c1ccc(C[N:7]2[CH2:6][CH2:5][N:4]([CH2:3][C:2](=[O:1])[NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[CH2:28][N:29]3[CH2:30][CH2:31][N:32](Cc4ccccc4)[CH2:33][CH2:34][N:35](Cc4ccccc4)[CH2:36][CH2:37][N:38](Cc4ccccc4)[CH2:39][CH2:40]3)[CH2:15][CH2:14][N:13](Cc3ccccc3)[CH2:12][CH2:... | O=C(CN1CCN(Cc2ccccc2)CCN(Cc2ccccc2)CCN(Cc2ccccc2)CC1)NCCOCCOCCNC(=O)CN1CCN(Cc2ccccc2)CCN(Cc2ccccc2)CCN(Cc2ccccc2)CC1 | O=C(CN1CCNCCNCCNCC1)NCCOCCOCCNC(=O)CN1CCNCCNCCNCC1 | null | [Pd] | C(C)O | Deprotection | OtherReaction | b3ef448f3c072b860503888ac4ae403973cda377756245b9bc84361b4ec206d0 | 705d8456c685cb47958fd61d15282eb479dd11776543e6bc5df803aca4cd9d81 | O=C(CN1CCNCCNCCNCC1)NCCOCCOCCNC(=O)CN1CCNCCNCCNCC1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-[N;H0;D3;+0:7](-C-c2:c:c:c:c:c:2)-[C:8]-[C:9]-[N;H0;D3;+0:10](-C-c2:c:c:c:c:c:2)-[C:11]-[C:12]-1)-c1:c:c:c:c:c:1.C(-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[N;H0;D3;+0:16](-C-c2:c:c:c:c:c:2)-[C:17]-[C:18]-[#7:19]-[C:20]-[C:21]-[N;H0;D3;+0:22](-C-c2:c:c:c:c:c:2)-[C:23]-[C:24]-1)-... | null | [] | null | null | null | null | A 100 mL Autoclave pressure reactor was charged with 9.2 g (8.3 mmol) of 8, 50 mL of ethanol and 3 g of 10% Pd/C. The reactor was pressurized to 220 psig with hydrogen for 3 hours at 80° C. The mixture was filtered and the filtrate was concentrated to a slightly yellow oil. 1H NMR, 13C NMR, and mass spectroscopy data w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine | Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine | c1ccccc1.C1C[NH]CC[NH]CC[NH]CC[NH]1.C1C[NH]CC[NH]CC[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CNCC[NH]CCNCCN1.C1CNCC[NH]CCNCCN1 | C1CNCC[NH]CCNCCN1.C1CNCC[NH]CCNCCN1 | Other | [Pd].C(C)O | null | null | O=C(CN1CCN(Cc2ccccc2)CCN(Cc2ccccc2)CCN(Cc2ccccc2)CC1)NCCOCCOCCNC(=O)CN1CCN(Cc2ccccc2)CCN(Cc2ccccc2)CCN(Cc2ccccc2)CC1>[Pd].C(C)O>O=C(CN1CCNCCNCCNCC1)NCCOCCOCCNC(=O)CN1CCNCCNCCNCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-de6058ab8e8a475cb7537815b0489c23 | CC1CO1.O=C(O)CN1CCNCCN(CC(=O)O)CCN(CC(=O)O)CC1>>CC(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1 | C1C(C)O1.C(=O)(O)CN1CCN(CCN(CCNCC1)CC(=O)O)CC(=O)O.[OH-].[Na+]>>C(=O)(O)CN1CCN(CCN(CCN(CC1)CC(C)O)CC(=O)O)CC(=O)O | [CH3:1][CH:2]1[O:3][CH2:4]1.[N:5]1([CH2:9][C:10](=[O:11])[OH:12])[CH2:6][CH2:7][NH:8][CH2:13][CH2:14][N:15]([CH2:16][C:17](=[O:18])[OH:19])[CH2:20][CH2:21][N:22]([CH2:23][C:24](=[O:25])[OH:26])[CH2:27][CH2:28]1>>[CH3:1][CH:2]([OH:3])[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH2:9][C:10](=[O:11])[OH:12])[CH2:13][CH2:14][N:15]([... | CC1CO1.O=C(O)CN1CCNCCN(CC(=O)O)CCN(CC(=O)O)CC1 | CC(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1 | null | null | O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 21c25a0a59c5eb9f0cfa1bff61bf24a37379bbb493ae62bd16e9525054d02154 | 463dd67c902792183527d1ff0fe86cd8bdfb6ac2b856921305dee39e0d05e1a4 | C1CNCCNCCNCCN1 | [#7:1]-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C:12]-[C:13]-[#7:14].[C;D1;H3:15]-[C:16]1-[CH2;D2;+0:17]-[O;H0;D2;+0:18]-1>>[#7:1]-[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:17]-[C:16](... | 96 | [{"value": 96.0, "product": "C(=O)(O)CN1CCN(CCN(CCN(CC1)CC(C)O)CC(=O)O)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 194.0 g (0.56 mol) of 15 in 450 mL of water is added sufficient NaOH to adjust the pH to 12.0 to 12.5 (the temperature is maintained below 30° C. during the addition). Propylene oxide (65 g, 1.12 mols) is added to the basic solution. After 6 hours at ambient temperature the excess propylene oxide and s... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine.Tertiary amine | Secondary alcohol.Tertiary amine.Tertiary amine | C1CO1.C1CNCC[NH]CC[NH]CC[NH]1 | C1C[NH]CC[NH]CC[NH]CC[NH]1 | C1C[NH]CC[NH]CC[NH]CC[NH]1 | null | O | null | null | CC1CO1.O=C(O)CN1CCNCCN(CC(=O)O)CCN(CC(=O)O)CC1>O>CC(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a60415cbb95e437fb80f71d2bf6155d2 | O=P(O)(O)O>>O=P([O-])([O-])[O-] | C(CCCCCCC)S(=O)(=O)[O-].[Na+].P(O)(O)(O)=O.[OH-].[Na+].Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1>>P(=O)([O-])([O-])[O-].C(CCCCCCC)S(=O)(=O)[O-] | [O:13]=[P:14]([OH:15])([OH:16])[OH:17]>>[O:13]=[P:14]([O-:15])([O-:16])[O-:17] | O=P(O)(O)O | O=P([O-])([O-])[O-] | null | null | C(C)#N.O | Oxidation | OtherReaction | 8411f9fce1f185c5c08a89a741e7494817f2d5e55ac6ad2b663e4ffb9ef8fbab | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | null | [O;D1;H0:1]=[#15:2](-[OH;D1;+0:3])(-[OH;D1;+0:4])-[OH;D1;+0:5]>>[O-;H0;D1:3]-[#15:2](-[O-;H0;D1:4])(-[O-;H0;D1:5])=[O;D1;H0:1] | null | [] | null | null | 5 | MINUTE | HPLC analysis indicated substantially pure 4-(2-piperidinoethoxy)benzoic acid, hydrochloride with only minor amounts of the methyl ester. The HPLC analysis was conducted as follows: A Zorbax C8 column was used (length: 25 cm; diameter: 4.6 mm; particle size: 5 microns). A weak eluent (60 mM phosphate and 10 mM octane s... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)#N.O | null | 0.083333 | O=P(O)(O)O>C(C)#N.O>O=P([O-])([O-])[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d12c63c36e004bc2bf7eed9db4fbf3fa | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>O=C(O)c1ccc(OCCN2CCCCC2)cc1 | C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C(=O)OC)C=C1.C(C)(=O)OC(C)C.Cl.ClCCN1CCCCC1>>Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1 | C[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][cH:19]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | O=C(O)c1ccc(OCCN2CCCCC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[CH2;D2;+0:9]-[C:10]-[#7:11]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 80 | CELSIUS | 5 | HOUR | To a 250 mL 3 neck flask equipped with mechanical stirring, condenser, and heating apparatus consisting of a RTD probe hooked via a temperature controller to a heating mantle and under nitrogen atmosphere, the following were added: 7.61 g methyl 4-hydroxybenzoate, 11.05 g β-chloroethylpiperidine hydrochloride, 16.59 g ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | O | 80 | 5 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>O>O=C(O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-48ae4b85295345399e5e9c5cdc2a4dea | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>O=C(O)c1ccc(OCCN2CCCCC2)cc1 | C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C(=O)OC)C=C1.C(C)(=O)OCCCCC.Cl.ClCCN1CCCCC1>>Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1 | C[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][cH:19]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | O=C(O)c1ccc(OCCN2CCCCC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[CH2;D2;+0:9]-[C:10]-[#7:11]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | To a 125 mL 3 neck flask with mechanical stirring, condenser, and a heating apparatus consisting of an RTD probe hooked via a temperature controller to a heating mantle, the following were added: 7.61 g methyl 4-hydroxybenzoate, 11.05 g β-chloroethylpiperidine hydrochloride, 16.59 g powdered potassium carbonate, and 60... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | O | null | null | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>O>O=C(O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-21f24d67043b4692bc3cf3a299646270 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>O=C(O)c1ccc(OCCN2CCCCC2)cc1 | C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C(=O)OC)C=C1.C(C)(=O)OCCCCC.Cl.ClCCN1CCCCC1>>Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1 | C[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][cH:19]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | O=C(O)c1ccc(OCCN2CCCCC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[CH2;D2;+0:9]-[C:10]-[#7:11]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 97 | CELSIUS | 8 | HOUR | To a 125 mL 3 neck flask with mechanical stirring, condensers, and a heating apparatus consisting of an RTD probe in the flask hooked via a temperature controller to a heating mantle, the following were added: 7.61 g methyl 4-hydroxybenzoate, 11.05 g -chloroethylpiperidine hydrochloride, 16.59 g powdered potassium carb... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | O | 97 | 8 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>O>O=C(O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0b3314315e2f4a7d9cfeba4d69f24baf | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>O=C(O)c1ccc(OCCN2CCCCC2)cc1 | C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C(=O)OC)C=C1.Cl.ClCCN1CCCCC1>>Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1 | C[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][cH:19]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | O=C(O)c1ccc(OCCN2CCCCC2)cc1 | null | null | C(C)(=O)OCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[CH2;D2;+0:9]-[C:10]-[#7:11]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 125 | CELSIUS | null | null | To a 125 mL 3 neck flask with mechanical stirring, condenser, and a heating apparatus consisting of an RTD probe in the flask hooked via a temperature controller to a heating mantle, the following were added: 7.61 g methyl 4-hydroxybenzoate, 11.05 g β-chloroethylpiperidine hydrochloride, 16.59 g powdered potassium carb... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | C(C)(=O)OCCCCC | 125 | null | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>C(C)(=O)OCCCCC>O=C(O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-eb82cfb403a14a159e26a2010c1cf21e | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>O=C(O)c1ccc(OCCN2CCCCC2)cc1 | C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C(=O)OC)C=C1.C(C)(=O)OCC.Cl.ClCCN1CCCCC1>>Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1 | C[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][cH:19]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | O=C(O)c1ccc(OCCN2CCCCC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[CH2;D2;+0:9]-[C:10]-[#7:11]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 4 | HOUR | To a 250 mL 3 neck flask with mechanical stirring and condenser, and a heating apparatus consisting of an RTD probe in the flask hooked via a temperature controller to a heating mantle and under nitrogen atmosphere, the following was added: 7.61 g of methyl 4-hydroxybenzoate, 11.05 g of β-chloroethylpiperidine hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | O | null | 4 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>O>O=C(O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8927131f18e74190aa3f19ad25d8e14b | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>O=C(O)c1ccc(OCCN2CCCCC2)cc1 | C(C)(=O)OCCCCC.Cl.ClCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C(=O)OC)C=C1.OC1=CC=C(C(=O)OC)C=C1>>Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1 | C[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][cH:19]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | O=C(O)c1ccc(OCCN2CCCCC2)cc1 | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[CH2;D2;+0:9]-[C:10]-[#7:11]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 95 | CELSIUS | null | null | To two 125 mL 3 neck flasks with mechanical stirring, condensers, and a heating apparatus consisting of an RTD probe in the flask hooked via a temperature controller to a heating mantle the following were added: 7.61 g of methyl 4-hydroxybenzoate, 11.05 g of β-chloroethylpiperidine hydrochloride, 16.59 g of powdered po... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | O.CC(=O)C | 95 | null | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>O.CC(=O)C>O=C(O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b190f2bf04fc450e98f6452e9e676dfb | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>O=C(O)c1ccc(OCCN2CCCCC2)cc1 | OC1=CC=C(C(=O)OC)C=C1.C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCCCC1>>Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1 | C[O:4][C:3](=[O:2])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][cH:19]1.Cl[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:2]=[C:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | O=C(O)c1ccc(OCCN2CCCCC2)cc1 | null | null | C(C)(=O)OCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[CH2;D2;+0:9]-[C:10]-[#7:11]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 91 | [{"value": 91.0, "product": "Cl.N1(CCCCC1)CCOC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a 2000 gallon tank were added: 1320 L of amyl acetate, 167.42 kg of methyl 4-hydroxybenzoate, 408.6 kg of potassium carbonate, and 283.5 kg of β-chloroethylpiperidine hydrochloride. The mixture was heated to 120° C.-125° C. for 5 hours, at which time HPLC analysis indicated complete consumption of the methyl 4-hydro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | C(C)(=O)OCCCCC | null | 1 | COC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>C(C)(=O)OCCCCC>O=C(O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8c764efa47ef4b9b8b9f366061dd03f4 | CC(C)=O.COC(=O)c1ccco1>>CC(=O)CC(=O)c1ccco1 | Cl.O1C(=CC=C1)C(=O)OC.[H-].[Na+].CC(=O)C>>O1C(=CC=C1)C(=O)CC(C)=O | [CH3:1][C:2](=[O:3])[CH3:4].CO[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][o:11]1>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][o:11]1 | CC(C)=O.COC(=O)c1ccco1 | CC(=O)CC(=O)c1ccco1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 32688b2be78fcb1623f924ded4f1da30562c8a1cc17a29844013a0b12a85add5 | da4745a356290ddd7ef0372302b86253afded9b0422422979166627a7dfa5740 | c1ccoc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C;D1;H3:7]-[C:8](-[CH3;D1;+0:9])=[O;D1;H0:10]>>[C;D1;H3:7]-[C:8](=[O;D1;H0:10])-[CH2;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 99.6 | [{"value": 99.0, "product": "O1C(=CC=C1)C(=O)CC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "O1C(=CC=C1)C(=O)CC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.27 ml (5.04 g, 40 mmol) methyl 2-furoate was added to a suspension of NaH (made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether. To this was added, so as to maintain the temperature below 30° C., 5.87 ml (4.64 g, 80 mmol) acetone (dried over CaCl2). This ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone.Ketone | null | null | c1ccoc1 | HO- | C(C)OCC | null | null | CC(C)=O.COC(=O)c1ccco1>C(C)OCC>CC(=O)CC(=O)c1ccco1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0c22f013146b4803aae89fe7bf0b0ee4 | CC(=O)CC(=O)c1ccco1.Cc1ccc(Nc2ccccc2C=O)cc1>>Cc1nc2ccccc2cc1C(=O)c1ccco1 | C1(=CC=C(C=C1)NC1=C(C=O)C=CC=C1)C.O1C(=CC=C1)C(=O)CC(C)=O.N1CCCCC1>>O1C(=CC=C1)C(=O)C=1C(=NC2=CC=CC=C2C1)C | O=[C:2]([CH3:1])[CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][o:18]1.Cc1ccc([NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH:10]=O)cc1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10][c:11]1[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][o:18]1 | CC(=O)CC(=O)c1ccco1.Cc1ccc(Nc2ccccc2C=O)cc1 | Cc1nc2ccccc2cc1C(=O)c1ccco1 | null | null | C(C)O | Miscellaneous | OtherReaction | 2416acfd09007c1ea10369ce459296e913e809b309d191a5ebdcba6e94949c3d | 70cdb026039ea0aa79cd465265ab660cd4e8b5ed67c3f66b3411348cb42687eb | O=C(c1cnc2ccccc2c1)c1ccco1 | C-c1:c:c:c(-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4](-[CH;D2;+0:5]=O):[c:6]):c:c:1.O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]:[#8;a:13]>>[#8;a:13]:[c:12]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:9]1:[cH;D2;+0:5]:[c:4](:[c:6]):[c:2](:[c:3]):[n;H0;D2;+0:1]:[c;H0;D3;+0:7]:1-[C;D1;H3:8] | 77 | [{"value": 77.0, "product": "O1C(=CC=C1)C(=O)C=1C(=NC2=CC=CC=C2C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 410 mg (1.95 mmol) N-(p-tolyl)-o-aminobenzaldehyde 326 mg (2.15 mmol), (2-furoyl)acetone and 50 mg piperidine in 4 ml 95% ethanol was heated overnight under reflux. Removal of he volatile materials left a black, gummy oil which was taken up in dichloromethane and, after being washed with 3M NaOH, brine, a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ketone.Secondary amine | Ketone | c1ccccc1.c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccoc1 | HO- | C(C)O | null | null | CC(=O)CC(=O)c1ccco1.Cc1ccc(Nc2ccccc2C=O)cc1>C(C)O>Cc1nc2ccccc2cc1C(=O)c1ccco1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9c207d102f3d43a682f5738fec76f3e0 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC21>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21 | C(C1=CC=CC=C1)N1CC2C(CC(C(C2C1)(O)C1=C(C=CC=C1)OC)O)(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=CC=C1)C1(CC(C(C2CNCC12)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | c1ccc(C[N:29]2[CH2:28][CH:27]3[C:14]([c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)([c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:13][CH:11]([OH:12])[C:9]([c:8]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]4)([OH:10])[CH:31]3[CH2:30]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9]1([OH:10])[CH:11]([OH:12])[C... | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC21 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21 | null | [OH-].[OH-].[Pd+2] | C(C)O | Deprotection | Hydrogenolysis of tertiary amines | 253182af9e6c4683f8e32255be69a71cb32bcb9cb5d661b565d49a4d2de9a8bd | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C2CCC(c3ccccc3)(c3ccccc3)C3CNCC23)cc1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:5]-[C:4]-1 | null | [] | 65 | CELSIUS | null | null | A mixture of 2 g of (3aRS, 4RS, 5RS, 7aRS)-2-benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol and 50 cm3 of ethanol is heated to 65° C. with stirring; 0.65 g of 20% palladium hydroxide on charcoal is added, and the reaction mixture is then hydrogenated, with stirring, at a temperature of 65° C. and at ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CCC2C[NH]CC2C1 | C1CCC2CNCC2C1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2CNCC2C1 | Other | [OH-].[OH-].[Pd+2].C(C)O | 65 | null | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC21>[OH-].[OH-].[Pd+2].C(C)O>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-eedc028c8bdc4146bb046986c7c5d7a6 | CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC2C1=O.COc1cccc[c]1[Mg][Br]>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC21 | C(C)OCC.COC1=C(C=CC=C1)[Mg]Br.C(C)(=O)OC1C(C2CN(CC2C(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=CC=C1)=O.[Cl-].[NH4+]>>C(C1=CC=CC=C1)N1CC2C(CC(C(C2C1)(O)C1=C(C=CC=C1)OC)O)(C1=CC=CC=C1)C1=CC=CC=C1 | CC(=O)[O:12][CH:11]1[C:9](=[O:10])[CH:38]2[CH:27]([C:14]([c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:13]1)[CH2:28][N:29]([CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[CH2:37]2.[Br][Mg][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH... | CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC2C1=O.COc1cccc[c]1[Mg][Br] | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC21 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | e498e00f826f84469c7f4f604736d37b54465d21893a5c4123d12c7de05ed650 | f7598ae3e9675ec604d2c92cc3bb7b70ef88fca2d39aac1c01617ae9a7c5c226 | c1ccc(CN2CC3C(c4ccccc4)CCC(c4ccccc4)(c4ccccc4)C3C2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6](-[C:7])-[C:8]-[#7:9].[#8:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](-[Mg]-[Br]):[c:14]:[c:15]>>[#7:9]-[C:8]-[C:6](-[C:7])-[C;H0;D4;+0:4](-[OH;D1;+0:5])(-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:11](-[#8:10]):[c:12])-[C:2](-[OH;D1;+0:1])-[C:3] | 64.8 | [{"value": 64.8, "product": "C(C1=CC=CC=C1)N1CC2C(CC(C(C2C1)(O)C1=C(C=CC=C1)OC)O)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 84.4 g of 2-methoxyphenylmagnesium bromide in 1000 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 22 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydro-4-isoindolone in 220 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone.Ester | Secondary alcohol.Tertiary alcohol | C1CCC2C[NH]CC2C1.c1ccccc1 | c1ccccc1.C1CCC2C[NH]CC2C1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2C[NH]CC2C1.c1ccccc1 | HBr.Mg | O1CCCC1 | null | null | CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC2C1=O.COc1cccc[c]1[Mg][Br]>O1CCCC1>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-913a6feed96a437ebd28023f775cac77 | CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C=CC1=O.CCCCOCN(Cc1ccccc1)C[Si](C)(C)C>>CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC2C1=O | C(C)(=O)OC1CC(C=CC1=O)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)OCN(C[Si](C)(C)C)CC1=CC=CC=C1.C([O-])([O-])=O.[Na+].[Na+]>>C(C)(=O)OC1C(C2CN(CC2C(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=CC=C1)=O | [CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH:20]=[CH:31][C:32]1=[O:33].CCCCO[CH2:21][N:22]([CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH2:30][Si](C)(C)C>>[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][C:7]([c:8]2[cH:9][cH:10][... | CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C=CC1=O.CCCCOCN(Cc1ccccc1)C[Si](C)(C)C | CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC2C1=O | null | FC(C(=O)O)(F)F | ClCCl | C-C Coupling | OtherReaction | afb1d7242d6e74cef85c96aa325bc405021655089e3bf824675e454b68d53365 | 03644a3196585e0d3367d533cc1c6d9c16aa98260b7b1ea5bb3a4b4e00da1fbe | O=C1CCC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC12 | C-C-C-C-O-[CH2;D2;+0:1]-[#7:2](-[C:3])-[CH2;D2;+0:4]-[Si](-C)(-C)-C.[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9](-[c:10])(-[c:11])-[CH;D2;+0:12]=[CH;D2;+0:13]-1>>[C:3]-[#7:2]1-[CH2;D2;+0:1]-[CH;D3;+0:12]2-[CH;D3;+0:13](-[CH2;D2;+0:4]-1)-[C:6](=[O;D1;H0:5])-[C:7]-[C:8]-[C:9]-2(-[c:10])-[c:11] | null | [] | null | null | 15 | HOUR | To a solution of 86 g of 6-acetoxy-4,4-diphenyl-2-cyclohexenone and 96 cm3 of N-butoxymethyl-N-(trimethylsilylmethyl)benzylamine in 1000 cm3 of dichloromethane are added 15 drops of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 15 hours, followed by addition of 2 g of sodium carbonate an... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Silyl protective group | Ketone | C1=CCCCC1 | C1CCC2C[NH]CC2C1 | c1ccccc1.c1ccccc1.C1CCC2C[NH]CC2C1.c1ccccc1 | HO- | FC(C(=O)O)(F)F.ClCCl | null | 15 | CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C=CC1=O.CCCCOCN(Cc1ccccc1)C[Si](C)(C)C>FC(C(=O)O)(F)F.ClCCl>CC(=O)OC1CC(c2ccccc2)(c2ccccc2)C2CN(Cc3ccccc3)CC2C1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f85f73c50d104dee8e88300abae7d75d | CI.COc1ccccc1CC(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C>>COc1ccccc1[C@H](C)C(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C | C[C@@H]1N(C(O[C@H]1C1=CC=CC=C1)=O)C(CC1=C(C=CC=C1)OC)=O.CI>>C[C@@H]1N(C(O[C@H]1C1=CC=CC=C1)=O)C([C@@H](C)C1=C(C=CC=C1)OC)=O | I[CH3:10].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][C:11](=[O:12])[N:13]1[C:14](=[O:15])[O:16][C@@H:17]([c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[C@@H:24]1[CH3:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C@H:9]([CH3:10])[C:11](=[O:12])[N:13]1[C:14](=[O:15])[O:16][C@@H:17]([c:18]2[cH:19][cH:20... | CI.COc1ccccc1CC(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C | COc1ccccc1[C@H](C)C(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C | null | null | O1CCCC1.C(C)(=O)OCC | C-C Coupling | Methylation with MeI_secondary | 0e09d968095a587418cca2841b1e4f096e8103de8fbb60e833faf1fb3df36a41 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C(Cc1ccccc1)N1C[C@H](c2ccccc2)OC1=O | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:12]>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[C@@H;D3;+0:8](-[CH3;D1;+0:1])-[c:9](:[c:10]):[c:11])-[C:12] | null | [] | null | null | 45 | MINUTE | To a solution, cooled to -50° C., of 10 g of (4S,5S)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)acetyl]-2-oxazolidinone in 150 cm3 of tetrahydrofuran are added 19.1 g of sodium 1,1,1,3,3,3-hexamethyldisilazide, and the mixture is stirred for 45 minutes at this temperature, followed by addition of 7.72 cm3 of methyl iodide. ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1COC[NH]1.c1ccccc1 | HI | O1CCCC1.C(C)(=O)OCC | null | 0.75 | CI.COc1ccccc1CC(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C>O1CCCC1.C(C)(=O)OCC>COc1ccccc1[C@H](C)C(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7f84790e52974f32a2309d5505a0da5c | COc1ccccc1CC(=O)O.C[C@@H]1NC(=O)O[C@H]1c1ccccc1>>COc1ccccc1CC(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C | C(CCC)[Li].C[C@@H]1NC(O[C@H]1C1=CC=CC=C1)=O.CC(C)(C)C(=O)Cl.[Cl-].[NH4+].COC1=C(C=CC=C1)CC(=O)O.[H-].[Na+]>>C[C@@H]1N(C(O[C@H]1C1=CC=CC=C1)=O)C(CC1=C(C=CC=C1)OC)=O | O[C:10]([CH2:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:11].[NH:12]1[C:13](=[O:14])[O:15][C@@H:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C@@H:23]1[CH3:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][C:10](=[O:11])[N:12]1[C:13](=[O:14])[O:15][C@@H:16]([c:17]2[cH:18][cH:19][cH:20][cH:21]... | COc1ccccc1CC(=O)O.C[C@@H]1NC(=O)O[C@H]1c1ccccc1 | COc1ccccc1CC(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C | null | null | O1CCCC1.CCCCCC.C(C)(=O)OCC | Protection | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | e6b8877cb13581e7e20b3470e89734487d9fd6d7ab7fd08c61d6e2df594633e1 | 921ca845ddbf5a24a35d32f527510f05b226860d95f601c94808547d4fe20ceb | O=C(Cc1ccccc1)N1C[C@H](c2ccccc2)OC1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[C:6]1-[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-1>>[C;D1;H3:5]-[C:6]1-[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 74.1 | [{"value": 74.1, "product": "C[C@@H]1N(C(O[C@H]1C1=CC=CC=C1)=O)C(CC1=C(C=CC=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 45 | MINUTE | To a suspension of 1.89 g of sodium hydride (80% dispersion in petroleum jelly) in 200 cm3 of dry tetrahydrofuran are added at room temperature 9.38 g of 2-methoxyphenylacetic acid. This suspension is cooled to -30° C. and 7.77 cm3 of pivalolyl chloride are added, finally followed by addition of a solution cooled to -7... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid | Carbamic ester.Substituted dicarboximide | C1COCN1 | C1COC[NH]1 | c1ccccc1.C1COC[NH]1.c1ccccc1 | HO- | O1CCCC1.CCCCCC.C(C)(=O)OCC | -30 | 0.75 | COc1ccccc1CC(=O)O.C[C@@H]1NC(=O)O[C@H]1c1ccccc1>O1CCCC1.CCCCCC.C(C)(=O)OCC>COc1ccccc1CC(=O)N1C(=O)O[C@@H](c2ccccc2)[C@@H]1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-71e76fe394b94ca08d51895d1070f820 | COc1ccccc1[C@@H](C)C(=O)O.COc1ccccc1[C@@]1(O)[C@H](O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CNC[C@@H]21>>COc1ccccc1[C@@H](C)C(=O)N1C[C@@H]2[C@H](C1)[C@@](O)(c1ccccc1OC)[C@H](O)CC2(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C1(C[C@H]([C@]([C@H]2CNC[C@@H]12)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1.COC1=C(C=CC=C1)[C@H](C(=O)O)C>>C1(=CC=CC=C1)C1(C[C@H]([C@]([C@H]2CN(C[C@@H]12)C([C@H](C)C1=C(C=CC=C1)OC)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | O[C:11]([C@@H:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[CH3:10])=[O:12].[NH:13]1[CH2:14][C@@H:15]2[C@H:16]([CH2:17]1)[C@@:18]([OH:19])([c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[O:26][CH3:27])[C@H:28]([OH:29])[CH2:30][C:31]2([c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[c:38]1[cH:39][cH:40][cH:41][cH:42][cH... | COc1ccccc1[C@@H](C)C(=O)O.COc1ccccc1[C@@]1(O)[C@H](O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CNC[C@@H]21 | COc1ccccc1[C@@H](C)C(=O)N1C[C@@H]2[C@H](C1)[C@@](O)(c1ccccc1OC)[C@H](O)CC2(c1ccccc1)c1ccccc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | f47032714243d00bafcf35beb26606675da0e4fc72a54d2453dc571b1b03d871 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1ccccc1)N1C[C@@H]2C(c3ccccc3)CCC(c3ccccc3)(c3ccccc3)[C@@H]2C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:4]-[C:3](-[c:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1 | 43.2 | [{"value": 43.2, "product": "C1(=CC=CC=C1)C1(C[C@H]([C@]([C@H]2CN(C[C@@H]12)C([C@H](C)C1=C(C=CC=C1)OC)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By working according to the procedure of Example 1, starting from 0.2 g of (3aR,4R,5R,7aR)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol and 0.11 g of (R)-2-(2-methoxyphenyl) propionic acid, 0.12 g of (3aR,4R,5R,7aR)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(R)-2-(2-methoxyphenyl) propionyl]perhydro-4,5-isoindo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CC[C@H]2CNC[C@H]2C1 | C1CC[C@H]2C[NH]C[C@H]2C1 | c1ccccc1.c1ccccc1.C1CC[C@H]2C[NH]C[C@H]2C1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1ccccc1[C@@H](C)C(=O)O.COc1ccccc1[C@@]1(O)[C@H](O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CNC[C@@H]21>>COc1ccccc1[C@@H](C)C(=O)N1C[C@@H]2[C@H](C1)[C@@](O)(c1ccccc1OC)[C@H](O)CC2(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-333a9cb6f4c44addbf85a8788cba6880 | COc1ccccc1[C@@H](C)C(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C.OO>>COc1ccccc1[C@@H](C)C(=O)O | S(=O)([O-])[O-].[Na+].[Na+].C[C@H]1N(C(O[C@@H]1C1=CC=CC=C1)=O)C([C@H](C)C1=C(C=CC=C1)OC)=O.[OH-].[Li+].OO>>COC1=C(C=CC=C1)[C@H](C(=O)O)C | C[C@@H]1[C@@H](c2ccccc2)OC(=O)N1[C:11]([C@@H:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[CH3:10])=[O:12].O[OH:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C@@H:9]([CH3:10])[C:11](=[O:12])[OH:13] | COc1ccccc1[C@@H](C)C(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C.OO | COc1ccccc1[C@@H](C)C(=O)O | null | null | O1CCCC1.O | Acylation | OtherReaction | 7fefc4011edcbe1dffc93611e6aa33ad6e04d8cda971cf8f87e37d90bd4136c7 | e2c678181571c92a15078448ccb62575ef30480d579a3bf1599e99419fa7b1b3 | c1ccccc1 | C-[C@H]1-N(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[c:5])-C(=O)-O-[C@@H]-1-c1:c:c:c:c:c:1.O-[OH;D1;+0:6]>>[C;D1;H3:4]-[C:3](-[c:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:6] | null | [] | null | null | 3 | HOUR | To a solution, cooled to +5° C., of 10.88 g of (4R, 5R)-4-methyl-5-phenyl-3-[(R)-2-(2-methoxyphenyl)propionyl]-2-oxazolidinone in 300 cm3 of tetrahydrofuran and 100 cm3 of water are added 2.71 g of lithium hydroxide and 13 cm3 of aqueous 30% hydrogen peroxide solution. The reaction mixture is stirred for 3 hours at thi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide.Peroxide | Carboxylic acid | C1COCN1.c1ccccc1 | null | c1ccccc1 | HO- | O1CCCC1.O | null | 3 | COc1ccccc1[C@@H](C)C(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C.OO>O1CCCC1.O>COc1ccccc1[C@@H](C)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4bd13a1ef22b4a92a19593e562a1264a | CI.COc1ccccc1CC(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C>>COc1ccccc1[C@@H](C)C(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C | C(C)(=O)O.C[C@H]1N(C(O[C@@H]1C1=CC=CC=C1)=O)C(CC1=C(C=CC=C1)OC)=O.CI>>C[C@H]1N(C(O[C@@H]1C1=CC=CC=C1)=O)C([C@H](C)C1=C(C=CC=C1)OC)=O | I[CH3:10].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][C:11](=[O:12])[N:13]1[C:14](=[O:15])[O:16][C@H:17]([c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[C@H:24]1[CH3:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C@@H:9]([CH3:10])[C:11](=[O:12])[N:13]1[C:14](=[O:15])[O:16][C@H:17]([c:18]2[cH:19][cH:20][... | CI.COc1ccccc1CC(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C | COc1ccccc1[C@@H](C)C(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C | null | null | O1CCCC1.C(C)(=O)OCC | C-C Coupling | Methylation with MeI_secondary | 0e09d968095a587418cca2841b1e4f096e8103de8fbb60e833faf1fb3df36a41 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C(Cc1ccccc1)N1C[C@@H](c2ccccc2)OC1=O | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:12]>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[C@H;D3;+0:8](-[CH3;D1;+0:1])-[c:9](:[c:10]):[c:11])-[C:12] | null | [] | null | null | 45 | MINUTE | To a solution, cooled to -50° C., of 22.82 g of (4R, 5R)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)acetyl]-2-oxazolidinone in 190 cm3 of tetrahydrofuran are added 19.31 g of sodium 1,1,1,3,3,3-hexamethyldisilazide, and the mixture is stirred for 45 minutes at this temperature, followed by addition of 8.82 cm3 of methyl iod... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1COC[NH]1.c1ccccc1 | HI | O1CCCC1.C(C)(=O)OCC | null | 0.75 | CI.COc1ccccc1CC(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C>O1CCCC1.C(C)(=O)OCC>COc1ccccc1[C@@H](C)C(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-305680a96b9241db832c63f34167b873 | COc1ccccc1CC(=O)O.C[C@H]1NC(=O)O[C@@H]1c1ccccc1>>COc1ccccc1CC(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C | C[C@H]1NC(O[C@@H]1C1=CC=CC=C1)=O.[Cl-].[NH4+].C(CCC)[Li].COC1=C(C=CC=C1)CC(=O)O>>C[C@H]1N(C(O[C@@H]1C1=CC=CC=C1)=O)C(CC1=C(C=CC=C1)OC)=O | O[C:10]([CH2:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:11].[NH:12]1[C:13](=[O:14])[O:15][C@H:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C@H:23]1[CH3:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][C:10](=[O:11])[N:12]1[C:13](=[O:14])[O:15][C@H:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH... | COc1ccccc1CC(=O)O.C[C@H]1NC(=O)O[C@@H]1c1ccccc1 | COc1ccccc1CC(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C | null | null | O1CCCC1.CCCCCC.C(C)(=O)OCC | Protection | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | e6b8877cb13581e7e20b3470e89734487d9fd6d7ab7fd08c61d6e2df594633e1 | 921ca845ddbf5a24a35d32f527510f05b226860d95f601c94808547d4fe20ceb | O=C(Cc1ccccc1)N1C[C@@H](c2ccccc2)OC1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[C:6]1-[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-1>>[C;D1;H3:5]-[C:6]1-[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | 30 | MINUTE | To a solution of 27.4 g of (4R,5R)-4-methyl-5-phenyl-2-oxazolidinone in 200 cm3 of dry tetrahydrofuran are added, at -78° C., 100 cm3 of a 1.6M butyllithium solution in hexane, followed by addition of 33.12 g of a solution of 2-methoxyphenylacetic acid in 30 cm3 of tetrahydrofuran. The mixture is stirred for 30 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid | Carbamic ester.Substituted dicarboximide | C1COCN1 | C1COC[NH]1 | c1ccccc1.C1COC[NH]1.c1ccccc1 | HO- | O1CCCC1.CCCCCC.C(C)(=O)OCC | null | 0.5 | COc1ccccc1CC(=O)O.C[C@H]1NC(=O)O[C@@H]1c1ccccc1>O1CCCC1.CCCCCC.C(C)(=O)OCC>COc1ccccc1CC(=O)N1C(=O)O[C@H](c2ccccc2)[C@H]1C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-50951ff0bd514fd4ae9a987c41fc417e | COc1ccccc1[C@@]1(O)C(O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CN(C(=O)Cc3ccccc3OCc3ccccc3)C[C@@H]21>>COc1ccccc1[C@@]1(O)[C@H](O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CN(C(=O)Cc3ccccc3O)C[C@@H]21 | C1(=CC=CC=C1)C1(CC([C@]([C@H]2CN(C[C@@H]12)C(CC1=C(C=CC=C1)OCC1=CC=CC=C1)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1>>C1(=CC=CC=C1)C1(C[C@H]([C@]([C@H]2CN(C[C@@H]12)C(CC1=C(C=CC=C1)O)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | c1ccc(C[O:39][c:38]2[c:33]([CH2:32][C:30]([N:29]3[CH2:28][C@H:27]4[C:14]([c:15]5[cH:16][cH:17][cH:18][cH:19][cH:20]5)([c:21]5[cH:22][cH:23][cH:24][cH:25][cH:26]5)[CH2:13][CH:11]([OH:12])[C@@:9]([c:8]5[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]5)([OH:10])[C@H:41]4[CH2:40]3)=[O:31])[cH:34][cH:35][cH:36][cH:37]2)cc1>>[CH3... | COc1ccccc1[C@@]1(O)C(O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CN(C(=O)Cc3ccccc3OCc3ccccc3)C[C@@H]21 | COc1ccccc1[C@@]1(O)[C@H](O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CN(C(=O)Cc3ccccc3O)C[C@@H]21 | null | [OH-].[OH-].[Pd+2] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Cc1ccccc1)N1C[C@@H]2C(c3ccccc3)CCC(c3ccccc3)(c3ccccc3)[C@@H]2C1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 84.6 | [{"value": 84.6, "product": "C1(=CC=CC=C1)C1(C[C@H]([C@]([C@H]2CN(C[C@@H]12)C(CC1=C(C=CC=C1)O)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 1.5 g of (3aR,4R, SR,7aR)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-benzyloxyphenyl)acetyl]perhydro-4,5-isoindolediol and 50 cm3 of ethanol is heated to 60° C. with stirring; 0.5 g of 20% palladium hydroxide on charcoal is added and the reaction mixture is then hydrogenated, with stirring, at a temperature of... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[C@H]2C[NH]C[C@H]2C1.c1ccccc1 | Other | [OH-].[OH-].[Pd+2].C(C)O | 60 | null | COc1ccccc1[C@@]1(O)C(O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CN(C(=O)Cc3ccccc3OCc3ccccc3)C[C@@H]21>[OH-].[OH-].[Pd+2].C(C)O>COc1ccccc1[C@@]1(O)[C@H](O)CC(c2ccccc2)(c2ccccc2)[C@@H]2CN(C(=O)Cc3ccccc3O)C[C@@H]21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fb44ceafc3a5487c9f4702671fd25908 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(Cl)Cc1ccc2ccccc2c1>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc4ccccc4c3)CC21 | O.C1=C(C=CC2=CC=CC=C12)CC(=O)Cl.C1(=CC=CC=C1)C1(CC(C(C2CNCC12)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1.C(C)(C)N(CC)C(C)C>>C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=CC2=CC=CC=C2C=C1)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9]1([OH:10])[CH:11]([OH:12])[CH2:13][C:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH:27]2[CH2:28][NH:29][CH2:43][CH:44]12.Cl[C:30](=[O:31])[CH2:32][c:33]1[cH:34][cH:35][c:36]2[cH:37][cH:38][cH:39][cH:40][c:41]2[cH:42]1... | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(Cl)Cc1ccc2ccccc2c1 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc4ccccc4c3)CC21 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 75017718c2fd505eefc84a6034d3d2fb46ceb0888a163173531a82534493cc96 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Cc1ccc2ccccc2c1)N1CC2C(c3ccccc3)CCC(c3ccccc3)(c3ccccc3)C2C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[C:9]-[C:8]-1 | 50.8 | [{"value": 50.8, "product": "C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=CC2=CC=CC=C2C=C1)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 0.42 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol in 10 cm3 of dichloromethane is added 0.21 cm3 of diisopropylethylamine, followed by 0.23 g of 2-naphthylacetyl chloride in 5.5 cm3 of dichloromethane. After stirring at room temperature for 1 hour, 25 cm3 of water... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCC2CNCC2C1 | C1CCC2C[NH]CC2C1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2C[NH]CC2C1.c1ccc2ccccc2c1 | HCl | ClCCl | null | 1 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(Cl)Cc1ccc2ccccc2c1>ClCCl>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc4ccccc4c3)CC21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f702a20ae3d74a158601fb61cb6aa32b | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(Cl)Cc1cccc2ccccc12>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3cccc4ccccc34)CC21 | C1(=CC=CC=C1)C1(CC(C(C2CNCC12)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1.C1(=CC=CC2=CC=CC=C12)CC(=O)Cl>>C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=CC=CC2=CC=CC=C12)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9]1([OH:10])[CH:11]([OH:12])[CH2:13][C:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH:27]2[CH2:28][NH:29][CH2:43][CH:44]12.Cl[C:30](=[O:31])[CH2:32][c:33]1[cH:34][cH:35][cH:36][c:37]2[cH:38][cH:39][cH:40][cH:41][c:42]12... | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(Cl)Cc1cccc2ccccc12 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3cccc4ccccc34)CC21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 75017718c2fd505eefc84a6034d3d2fb46ceb0888a163173531a82534493cc96 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Cc1cccc2ccccc12)N1CC2C(c3ccccc3)CCC(c3ccccc3)(c3ccccc3)C2C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[C:9]-[C:8]-1 | 45.9 | [{"value": 45.9, "product": "C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=CC=CC2=CC=CC=C12)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By working according to the procedure of Example A, starting from 0.62 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol and 0.35 g of 1-naphthylacetyl chloride, 0.4 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2methoxyphenyl)-2-[(1-naphthyl)acetyl]perhydro-4,5-isoindolediol is obtained, m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCC2CNCC2C1 | C1CCC2C[NH]CC2C1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2C[NH]CC2C1.c1ccc2ccccc2c1 | HCl | null | null | null | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(Cl)Cc1cccc2ccccc12>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3cccc4ccccc34)CC21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3a7d3fcf84904af89b0162e8dcc4e243 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.COc1ccccc1CC(=O)O>>COc1ccccc1CC(=O)C1NCC2C1C(c1ccccc1)(c1ccccc1)CC(O)C2(O)c1ccccc1OC | Cl.C1(=CC=CC=C1)C1(CC(C(C2CNCC12)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1.C(C)N(CC)CC.COC1=C(C=CC=C1)CC(=O)O>>C1(=CC=CC=C1)C1(CC(C(C2CNC(C12)C(CC1=C(C=CC=C1)OC)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | [CH2:12]1[NH:13][CH2:14][CH:15]2[CH:16]1[C:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH2:30][CH:31]([OH:32])[C:33]2([OH:34])[c:35]1[cH:36][cH:37][cH:38][cH:39][c:40]1[O:41][CH3:42].O[C:10]([CH2:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)=[O:11]>>[CH3:1][O:2]... | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.COc1ccccc1CC(=O)O | COc1ccccc1CC(=O)C1NCC2C1C(c1ccccc1)(c1ccccc1)CC(O)C2(O)c1ccccc1OC | null | null | ClCCl | C-C Coupling | OtherReaction | 348f28eb1206b1d8c46913f3c2a9e136a52e67dd0c5f883196b7d72ab51b799d | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(Cc1ccccc1)C1NCC2C(c3ccccc3)CCC(c3ccccc3)(c3ccccc3)C12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]-[C:6]1-[C:7]-[C:8]-[#7:9]-[CH2;D2;+0:10]-1>>[C:5]-[C:6]1-[C:7]-[C:8]-[#7:9]-[CH;D3;+0:10]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 77.5 | [{"value": 77.5, "product": "C1(=CC=CC=C1)C1(CC(C(C2CNC(C12)C(CC1=C(C=CC=C1)OC)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | To a solution of 4.5 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol hydrochloride in 100 cm3 of dichloromethane, cooled to 0° C., are added 4.2 cm3 of triethylamine, followed by 2.4 g of (2-methoxyphenyl)acetic acid in 50 cm3 of dichloromethane. Stirring is carried out at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | C1CCC2CNCC2C1 | C1CCC2CNCC2C1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2CNCC2C1.c1ccccc1 | HO- | ClCCl | null | 1.5 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.COc1ccccc1CC(=O)O>ClCCl>COc1ccccc1CC(=O)C1NCC2C1C(c1ccccc1)(c1ccccc1)CC(O)C2(O)c1ccccc1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cd22a7b3952a4e9c87a905c978cab9b6 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(O)Cc1ccccc1N1CCCC1>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccccc3N3CCCC3)CC21 | C1(=CC=CC=C1)C1(CC(C(C2CNCC12)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1.N1(CCCC1)C1=C(C=CC=C1)CC(=O)O>>C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=C(C=CC=C1)N1CCCC1)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9]1([OH:10])[CH:11]([OH:12])[CH2:13][C:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH:27]2[CH2:28][NH:29][CH2:44][CH:45]12.O[C:30](=[O:31])[CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][c:38]1[N:39]1[CH2:40][CH2:41][CH2:42... | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(O)Cc1ccccc1N1CCCC1 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccccc3N3CCCC3)CC21 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2457854ffd9a54613a67a643011206ed6317d3a06f087c446877d03b7cda3988 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1ccccc1N1CCCC1)N1CC2C(c3ccccc3)CCC(c3ccccc3)(c3ccccc3)C2C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[C:9]-[C:8]-1 | 77.8 | [{"value": 77.8, "product": "C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=C(C=CC=C1)N1CCCC1)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By working according to the procedure of Example 1, starting from 0.62 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol and 0.40 g of 2-(1-pyrrolidinyl)phenylacetic acid, 0.70 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-(1-pyrrolidinyl)phenyl)acetyl]perhydro-4,5-is... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCC2CNCC2C1 | C1CCC2C[NH]CC2C1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2C[NH]CC2C1.c1ccccc1.C1CC[NH]C1 | HO- | null | null | null | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CNCC21.O=C(O)Cc1ccccc1N1CCCC1>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccccc3N3CCCC3)CC21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ebb6dfc4c437444cbe1e002b13554768 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc([N+](=O)[O-])cc3)CC21>>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc(N)cc3)CC21 | O.[Cl-].[NH4+].C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=CC=C(C=C1)[N+](=O)[O-])=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1>>C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=CC=C(C=C1)N)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1 | O=[N+:37]([O-])[c:36]1[cH:35][cH:34][c:33]([CH2:32][C:30]([N:29]2[CH2:28][CH:27]3[C:14]([c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)([c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:13][CH:11]([OH:12])[C:9]([c:8]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]4)([OH:10])[CH:41]3[CH2:40]2)=[O:31])[cH:39][cH:38]1>>[CH3:1][O:... | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc([N+](=O)[O-])cc3)CC21 | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc(N)cc3)CC21 | null | [Zn] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Cc1ccccc1)N1CC2C(c3ccccc3)CCC(c3ccccc3)(c3ccccc3)C2C1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 74.9 | [{"value": 74.9, "product": "C1(=CC=CC=C1)C1(CC(C(C2CN(CC12)C(CC1=CC=C(C=C1)N)=O)(O)C1=C(C=CC=C1)OC)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(4-nitrophenyl)acetyl]perhydro-4,5-isoindolediol in 3.3 cm3 of methanol, maintained at a temperature of 50° C., are added 33 cm3 of water, 4.6 g of ammonium chloride and 2.2 g of zinc powder. The reaction mixture is brought to reflux for 30... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2C[NH]CC2C1.c1ccccc1 | Other | [Zn].CO | null | null | COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc([N+](=O)[O-])cc3)CC21>[Zn].CO>COc1ccccc1C1(O)C(O)CC(c2ccccc2)(c2ccccc2)C2CN(C(=O)Cc3ccc(N)cc3)CC21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7b3d35f9eec5401abafe481d8cf02aaf | C=C(Cl)C#N.N#CC(NC(=O)C(F)(F)F)c1ccc(Cl)cc1>>N#Cc1cc(C(F)(F)F)[nH]c1-c1ccc(Cl)cc1 | ClC(C#N)=C.ClC1=CC=C(C=C1)C(NC(C(F)(F)F)=O)C#N.CS(=O)(=O)O.C(C)(=O)Cl.C(C)N(CC)CC>>ClC1=CC=C(C=C1)C=1NC(=CC1C#N)C(F)(F)F | ClC([C:2]#[N:1])=[CH2:4].N#[C:3][CH:11]([NH:10][C:5](=O)[C:6]([F:7])([F:8])[F:9])[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([C:6]([F:7])([F:8])[F:9])[nH:10][c:11]1-[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | C=C(Cl)C#N.N#CC(NC(=O)C(F)(F)F)c1ccc(Cl)cc1 | N#Cc1cc(C(F)(F)F)[nH]c1-c1ccc(Cl)cc1 | null | null | O.C(C)#N.C1(=CC=CC=C1)C.C(C)(=O)OCC.CCCCCCC | Aromatic Heterocycle Formation | OtherReaction | 3f91c15dbdc300705d913ba177e9f6eca4eba8456c9598dba9bdbaa28bf4c731 | bce0d127b06909f028c7567105178a809c3b4d2897dafeb4ba99dcbf1cc5f33f | c1ccc(-c2ccc[nH]2)cc1 | Cl-C(=[CH2;D1;+0:1])-[C;H0;D2;+0:2]#[N;D1;H0:3].N#[C;H0;D2;+0:4]-[CH;D3;+0:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=O)-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[F;D1;H0:9]-[C:8](-[F;D1;H0:10])(-[F;D1;H0:11])-[c;H0;D3;+0:7]1:[cH;D2;+0:1]:[c;H0;D3;+0:4](-[C;H0;D2;+0:2]#[N;D1... | null | [] | 80 | CELSIUS | null | null | A slurry of N-[(p-chlorophenyl)cyanomethyl]-2,2,2-trifluoroacetamide (13.1 g, 0.05 mol) in toluene is treated sequentially with methanesulfonic acid (2.4 g, 0.025 mol) and acetyl chloride (4.32 g, 0.055 mol), at room temperature, heated at 80° C. for 2 hours, cooled to room temperature, diluted with acetonitrile, treat... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Nitrile.Nitrile.Secondary amide.Vinyl | Nitrile | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HCl | O.C(C)#N.C1(=CC=CC=C1)C.C(C)(=O)OCC.CCCCCCC | 80 | null | C=C(Cl)C#N.N#CC(NC(=O)C(F)(F)F)c1ccc(Cl)cc1>O.C(C)#N.C1(=CC=CC=C1)C.C(C)(=O)OCC.CCCCCCC>N#Cc1cc(C(F)(F)F)[nH]c1-c1ccc(Cl)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cda2074a6391416591e32f8f1d0e302b | CN(C)[NH+]=CCl.CO/N=C(\C(=O)Cl)c1csc(N)n1>>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1 | [Cl-].CN(C)[NH+]=CCl.O1CCCC1.Cl.NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC>>CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl | Cl[CH:13]=[NH+:14]N([CH3:15])[CH3:16].[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[Cl:7])[c:8]1[cH:9][s:10][c:11]([NH2:12])[n:17]1>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[Cl:7])[c:8]1[cH:9][s:10][c:11]([N:12]=[CH:13][N:14]([CH3:15])[CH3:16])[n:17]1 | CN(C)[NH+]=CCl.CO/N=C(\C(=O)Cl)c1csc(N)n1 | CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1 | null | null | null | Functional Group Interconversion | OtherReaction | edca639bc5aaef9daccd9d92f10fe8ab1d1d4efb5b9878178998522894b2e63d | 5de7b66aa3e43f62e2731183e10e8dc9c78ad8588054e17fa7602a7444dcae43 | c1cscn1 | Cl-[CH;D2;+0:1]=[NH+;D2:2]-N(-[CH3;D1;+0:3])-[CH3;D1;+0:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[CH3;D1;+0:3]-[N;H0;D3;+0:2](-[CH3;D1;+0:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 47 | [{"value": 47.0, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 40 | MINUTE | Dimethylaminochloromethyleneammonium chloride (496 mg, 3.87 mmol) was dissolved in 10 ml of tetrahydrofuran, followed by cooling to -10° C. Added to the solution were 870 mg (3.4 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetyl chloride hydrochloride and the resulting mixture was stirred for 40 minutes. The re... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary amine | Tertiary amine | null | null | c1cscn1 | HCl | null | -10 | 0.666667 | CN(C)[NH+]=CCl.CO/N=C(\C(=O)Cl)c1csc(N)n1>>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-94207a37d3ee491990b588d121f42aa9 | CN(C)[NH+]=CCl.CO/N=C(\C(=O)O)c1csc(N)n1.[Cl-]>>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl | [Cl-].CN(C)[NH+]=CCl.NC=1SC=C(N1)/C(/C(=O)O)=N/OC.C(C)(C)OC(C)C>>CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl | N([NH+:14]=[CH:13][Cl:7])([CH3:15])[CH3:16].O[C:5](/[C:4](=[N:3]\[O:2][CH3:1])[c:8]1[cH:9][s:10][c:11]([NH2:12])[n:17]1)=[O:6].[Cl-:18]>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[Cl:7])[c:8]1[cH:9][s:10][c:11]([N:12]=[CH:13][N:14]([CH3:15])[CH3:16])[n:17]1.[ClH:18] | CN(C)[NH+]=CCl.CO/N=C(\C(=O)O)c1csc(N)n1.[Cl-] | CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 4123e9b2fd562f23844f2df5587e5f936a112b292e018473b3637589a0b28ed7 | a52ac2539d6757599153d533a8fbe84d7ef8a9f7d469b2a81399b2c50c0e1b35 | c1cscn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\[#8:5])-[c:6]1:[#7;a:7]:[c:8](-[NH2;D1;+0:9]):[#16;a:10]:[c:11]:1.[CH3;D1;+0:12]-N(-[CH3;D1;+0:13])-[NH+;D2:14]=[CH;D2;+0:15]-[Cl;H0;D1;+0:16].[Cl-;H0;D0:17]>>[#8:5]/[#7:4]=[C:3](\[C;H0;D3;+0:1](-[Cl;H0;D1;+0:16])=[O;D1;H0:2])-[c:6]1:[#7;a:7]:[c:8](-[N;H0;D2;+0:9]=[CH;D2;+0:... | 96.9 | [{"value": 96.9, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl", "details": "PERCENTYIELD", "is_desired": false}] | -12 | CELSIUS | 40 | MINUTE | Dimethylaminochloromethyleneammonium chloride (1.52 g, 12.0 mmol) was dissolved in 7 ml of tetrahydrofuran, followed by cooling to -12° C. Added to the solution were 1.10 g (5.5 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and the resulting mixture was stirred for 40 minutes. Isopropyl ether (16 ml) w... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Primary amine | Acyl halide.Tertiary amine | null | null | c1cscn1 | HO- | O1CCCC1 | -12 | 0.666667 | CN(C)[NH+]=CCl.CO/N=C(\C(=O)O)c1csc(N)n1.[Cl-]>O1CCCC1>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9959aa0b4e7344f4bd7a706d9a088565 | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1.O=C(Cl)C(=O)Cl>>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl | NC=1SC=C(N1)/C(/C(=O)O)=N/OC.CN(C=O)C.C(C(=O)Cl)(=O)Cl>>CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl | O=[CH:13][N:14]([CH3:15])[CH3:16].O[C:5](/[C:4](=[N:3]\[O:2][CH3:1])[c:8]1[cH:9][s:10][c:11]([NH2:12])[n:17]1)=[O:6].O=C(C(=O)[Cl:18])[Cl:7]>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[Cl:7])[c:8]1[cH:9][s:10][c:11]([N:12]=[CH:13][N:14]([CH3:15])[CH3:16])[n:17]1.[ClH:18] | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1.O=C(Cl)C(=O)Cl | CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl | null | null | O1CCCC1 | Miscellaneous | OtherReaction | c1fd11cc7b768c67699cde9de4369b36d9319360ddd6d5b5b2074076a00a8c49 | c7899aa0f0dc139674ae89005ef4b2ef1c28749aa960b8e5456d4ec85191bb72 | c1cscn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](=[#7:4]\[#8:5])-[c:6]1:[#7;a:7]:[c:8](-[NH2;D1;+0:9]):[#16;a:10]:[c:11]:1.O=C(-[Cl;H0;D1;+0:12])-C(=O)-[Cl;H0;D1;+0:13].O=[CH;D2;+0:14]-[#7:15](-[C;D1;H3:16])-[C;D1;H3:17]>>[#8:5]/[#7:4]=[C:3](\[C;H0;D3;+0:1](-[Cl;H0;D1;+0:13])=[O;D1;H0:2])-[c:6]1:[#7;a:7]:[c:8](-[N;H0;D2;+0:9]=[CH;... | 43 | [{"value": 43.0, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.4, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 10 | MINUTE | Dimethylformamide (1.6 g, 22 mmol) and 10 ml of tetrahydrofuran were mixed, to which 3.06 g (24 mmol) of oxalyl chloride were added dropwise under ice-cooling. After completion of the dropwise addition, the resulting mixture was stirred for further 10 minutes and was then cooled to -15° C. To the mixture so obtained, w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid.Tertiary amide.Primary amine | Acyl halide | null | null | c1cscn1 | HO- | O1CCCC1 | -15 | 0.166667 | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1.O=C(Cl)C(=O)Cl>O1CCCC1>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-40fa5bfaa01d48d18c4efaa85968461c | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1.O=C(Cl)OC(Cl)(Cl)Cl>>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl | C(C)(=O)OC(C)C.ClC(=O)OC(Cl)(Cl)Cl.CN(C=O)C.NC=1SC=C(N1)/C(/C(=O)O)=N/OC>>CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl | O=[CH:13][N:14]([CH3:15])[CH3:16].O[C:5](/[C:4](=[N:3]\[O:2][CH3:1])[c:8]1[cH:9][s:10][c:11]([NH2:12])[n:17]1)=[O:6].O=C(OC(Cl)(Cl)[Cl:18])[Cl:7]>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[Cl:7])[c:8]1[cH:9][s:10][c:11]([N:12]=[CH:13][N:14]([CH3:15])[CH3:16])[n:17]1.[ClH:18] | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1.O=C(Cl)OC(Cl)(Cl)Cl | CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl | null | null | O1CCCC1 | Miscellaneous | OtherReaction | eaea42979679f589b5c838d189e8bcdbc0f11e2bb8facc5306b0359763adaced | ce7fd3fb70154b1296c89587dc416e49acfde049e0a380446ef38465c9572215 | c1cscn1 | Cl-C(-Cl)(-[Cl;H0;D1;+0:1])-O-C(=O)-[Cl;H0;D1;+0:2].O-[C;H0;D3;+0:3](=[O;D1;H0:4])/[C:5](=[#7:6]\[#8:7])-[c:8]1:[#7;a:9]:[c:10](-[NH2;D1;+0:11]):[#16;a:12]:[c:13]:1.O=[CH;D2;+0:14]-[#7:15](-[C;D1;H3:16])-[C;D1;H3:17]>>[#8:7]/[#7:6]=[C:5](\[C;H0;D3;+0:3](-[Cl;H0;D1;+0:2])=[O;D1;H0:4])-[c:8]1:[#7;a:9]:[c:10](-[N;H0;D2;+0... | 94 | [{"value": 94.0, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)Cl)=N/OC.Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Dimethylformamide (0.8 g, 11 mmol) was added to 9 ml of tetrahydrofuran, followed by ice-cooling. To the resulting mixture, 0.6 ml of trichloromethyl chloroformate was added dropwise under ice-cooling. After stirring the resulting mixture for 30 minutes, the mixture was cooled to -10° C. (Z)-2-(2-Amino-thiazol-4-yl)-2-... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Carboxylic acid.Ether.Tertiary amide.Primary amine | Acyl halide | null | null | c1cscn1 | HCl | O1CCCC1 | null | 0.5 | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1.O=C(Cl)OC(Cl)(Cl)Cl>O1CCCC1>CO/N=C(\C(=O)Cl)c1csc(N=CN(C)C)n1.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-44c097f4597f45aaa8e470701df07836 | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1>>CO/N=C(\C(=O)OC)c1csc(N=CN(C)C)n1 | NC=1SC=C(N1)/C(/C(=O)O)=N/OC.O1CCCC1.CN(C=O)C.[OH-].[Na+].P(=O)(Cl)(Cl)Cl>>CN(C)C=NC=1SC=C(N1)/C(/C(=O)OC)=N/OC | O=[CH:14][N:15]([CH3:8])[CH3:17].[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[OH:7])[c:9]1[cH:10][s:11][c:12]([NH2:13])[n:18]1>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][s:11][c:12]([N:13]=[CH:14][N:15]([CH3:16])[CH3:17])[n:18]1 | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1 | CO/N=C(\C(=O)OC)c1csc(N=CN(C)C)n1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | d70a286ad904b1503497cdcff8261707546da8ca90f4a12730593efb811ff04d | 9bbed73db60f00920df17e3dd909bd56740044f6820b270937aa116b0a5812c9 | c1cscn1 | O=[CH;D2;+0:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH3;D1;+0:4].[#7:5]=[C:6](\[C:7](=[O;D1;H0:8])-[OH;D1;+0:9])-[c:10]1:[#7;a:11]:[c:12](-[NH2;D1;+0:13]):[#16;a:14]:[c:15]:1>>[#7:5]=[C:6](\[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH3;D1;+0:4])-[c:10]1:[#7;a:11]:[c:12](-[N;H0;D2;+0:13]=[CH;D2;+0:1]-[N;H0;D3;+0:2](-[C;D1;H3:16])-[C... | 94 | [{"value": 94.0, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)OC)=N/OC", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 3 | HOUR | (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid (0.5 g, 2.5 mmol) was dissolved in 20 ml of tetrahydrofuran. Subsequent to the addition of 0.72 g (9.9 mmol) of dimethylformamide, the resulting solution was cooled to 5° C. The solution was added with 1.52 g (9.9 mmol) of phosphorus oxychloride and the resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Primary amine | Ester.Tertiary amine | null | null | c1cscn1 | null | CO | 5 | 3 | CN(C)C=O.CO/N=C(\C(=O)O)c1csc(N)n1>CO>CO/N=C(\C(=O)OC)c1csc(N=CN(C)C)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c46fb7910fca43abbd53bbc36327201c | CN(C)[NH+]=CCl.CO.CO/N=C(\C(=O)O)c1csc(N)n1>>CO/N=C(\C(=O)OC)c1csc(N=CN(C)C)n1 | [Cl-].CN(C)[NH+]=CCl.O1CCCC1.NC=1SC=C(N1)/C(/C(=O)O)=N/OC.C(O)([O-])=O.[Na+].CO>>CN(C)C=NC=1SC=C(N1)/C(/C(=O)OC)=N/OC | Cl[CH:14]=[NH+:15]N([CH3:16])[CH3:17].O[CH3:8].[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[OH:7])[c:9]1[cH:10][s:11][c:12]([NH2:13])[n:18]1>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][s:11][c:12]([N:13]=[CH:14][N:15]([CH3:16])[CH3:17])[n:18]1 | CN(C)[NH+]=CCl.CO.CO/N=C(\C(=O)O)c1csc(N)n1 | CO/N=C(\C(=O)OC)c1csc(N=CN(C)C)n1 | null | null | null | Functional Group Interconversion | OtherReaction | 3456d0573b2da524291a0f1b61970c154474fb5ccafd90e0e9271cd005bd60f0 | c47988b2c9d3d9360562c6f39c2436905f74fa093bcb3b817d9ec26f5479a58c | c1cscn1 | Cl-[CH;D2;+0:1]=[NH+;D2:2]-N(-[CH3;D1;+0:3])-[CH3;D1;+0:4].O-[CH3;D1;+0:5].[#7:6]=[C:7](\[C:8](=[O;D1;H0:9])-[OH;D1;+0:10])-[c:11]1:[#7;a:12]:[c:13](-[NH2;D1;+0:14]):[#16;a:15]:[c:16]:1>>[#7:6]=[C:7](\[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[CH3;D1;+0:5])-[c:11]1:[#7;a:12]:[c:13](-[N;H0;D2;+0:14]=[CH;D2;+0:1]-[N;H0;D3;+0:2... | 95 | [{"value": 95.0, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)OC)=N/OC", "details": "PERCENTYIELD", "is_desired": false}] | -3 | CELSIUS | 40 | MINUTE | Dimethylaminochloromethyleneammonium chloride (400 mg, 3.1 mmol) was dissolved in 10 ml of tetrahydrofuran, followed by cooling to -3° C. The solution was added with 300 mg (1.5 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and the mixture so obtained was stirred for 40 minutes. After the resulting mix... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Primary amine.Methanol | Ester.Tertiary amine | null | null | c1cscn1 | HCl | null | -3 | 0.666667 | CN(C)[NH+]=CCl.CO.CO/N=C(\C(=O)O)c1csc(N)n1>>CO/N=C(\C(=O)OC)c1csc(N=CN(C)C)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-189585ea02bc4713a78b924966961140 | CN(C)[NH+]=CCl.CO.CO/N=C(\C(=O)O)c1csc(N)n1>>CO/N=C(/C(=O)OC)c1csc(N=CN(C)C)n1 | [Cl-].CN(C)[NH+]=CCl.O1CCCC1.NC=1SC=C(N1)/C(/C(=O)O)=N/OC.C(O)([O-])=O.[Na+].CO>>CN(C)C=NC=1SC=C(N1)\C(\C(=O)OC)=N/OC | Cl[CH:14]=[NH+:15]N([CH3:16])[CH3:17].O[CH3:8].[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[OH:7])[c:9]1[cH:10][s:11][c:12]([NH2:13])[n:18]1>>[CH3:1][O:2]/[N:3]=[C:4](/[C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][s:11][c:12]([N:13]=[CH:14][N:15]([CH3:16])[CH3:17])[n:18]1 | CN(C)[NH+]=CCl.CO.CO/N=C(\C(=O)O)c1csc(N)n1 | CO/N=C(/C(=O)OC)c1csc(N=CN(C)C)n1 | null | null | null | Functional Group Interconversion | OtherReaction | 3456d0573b2da524291a0f1b61970c154474fb5ccafd90e0e9271cd005bd60f0 | c47988b2c9d3d9360562c6f39c2436905f74fa093bcb3b817d9ec26f5479a58c | c1cscn1 | Cl-[CH;D2;+0:1]=[NH+;D2:2]-N(-[CH3;D1;+0:3])-[CH3;D1;+0:4].O-[CH3;D1;+0:5].[#7:6]=[C:7](\[C:8](=[O;D1;H0:9])-[OH;D1;+0:10])-[c:11]1:[#7;a:12]:[c:13](-[NH2;D1;+0:14]):[#16;a:15]:[c:16]:1>>[#7:6]=[C:7](/[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[CH3;D1;+0:5])-[c:11]1:[#7;a:12]:[c:13](-[N;H0;D2;+0:14]=[CH;D2;+0:1]-[N;H0;D3;+0:2... | 72 | [{"value": 72.0, "product": "CN(C)C=NC=1SC=C(N1)\\C(\\C(=O)OC)=N/OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Dimethylaminochloromethyleneammonium chloride (400 mg, 3.1 mmol) was dissolved in 10 ml of tetrahydrofuran, Added to the resulting solution were 300 mg of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino-acetic acid, followed by stirring at room temperature for 16 hours. Methanol (10 ml) was added thereto. The mixture so obt... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Primary amine.Methanol | Ester.Tertiary amine | null | null | c1cscn1 | HCl | null | null | 16 | CN(C)[NH+]=CCl.CO.CO/N=C(\C(=O)O)c1csc(N)n1>>CO/N=C(/C(=O)OC)c1csc(N=CN(C)C)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8f24189601874b8dbcf6802f3355fe98 | CC/C=C(\C(=O)O)c1csc(N)n1.CN(C)[NH+]=CCl.CO>>CC/C=C(\C(=O)OC)c1csc(N=CN(C)C)n1 | C(O)([O-])=O.[Na+].CO.[Cl-].CN(C)[NH+]=CCl.O1CCCC1.NC=1SC=C(N1)/C(/C(=O)O)=C/CC>>CN(C)C=NC=1SC=C(N1)/C(/C(=O)OC)=C/CC | [CH3:1][CH2:2]/[CH:3]=[C:4](\[C:5](=[O:6])[OH:7])[c:9]1[cH:10][s:11][c:12]([NH2:13])[n:18]1.Cl[CH:14]=[NH+][N:15]([CH3:16])[CH3:17].O[CH3:8]>>[CH3:1][CH2:2]/[CH:3]=[C:4](\[C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][s:11][c:12]([N:13]=[CH:14][N:15]([CH3:16])[CH3:17])[n:18]1 | CC/C=C(\C(=O)O)c1csc(N)n1.CN(C)[NH+]=CCl.CO | CC/C=C(\C(=O)OC)c1csc(N=CN(C)C)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cc868f42fc4ea4486b68a23a4a842774e8dec1dace7529177ac927f86d56cca8 | c9485ed1774eb17e96eafc224e6fcdfff31a74bf9276a9087acc5464567f3272 | c1cscn1 | Cl-[CH;D2;+0:1]=[NH+]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[C;D1;H3:4].O-[CH3;D1;+0:5].[C:6]/[C:7]=[C:8](\[C:9](=[O;D1;H0:10])-[OH;D1;+0:11])-[c:12]1:[#7;a:13]:[c:14](-[NH2;D1;+0:15]):[#16;a:16]:[c:17]:1>>[C:6]/[C:7]=[C:8](\[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-[CH3;D1;+0:5])-[c:12]1:[#7;a:13]:[c:14](-[N;H0;D2;+0:15]=[CH;D2;+0:... | 67 | [{"value": 67.0, "product": "CN(C)C=NC=1SC=C(N1)/C(/C(=O)OC)=C/CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Dimethylaminochloromethyleneammonium chloride (830 mg, 6.5 mmol) was added to 12 ml of tetrahydrofuran, and the resulting mixture was ice-cooled. Added to the mixture were 196 mg (0.99 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-pentenoic acid, followed by stirring for 1 hour. Methanol (10 ml) was added thereto. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Primary amine.Methanol | Ester.Tertiary amine | null | null | c1cscn1 | HCl | null | null | 1 | CC/C=C(\C(=O)O)c1csc(N)n1.CN(C)[NH+]=CCl.CO>>CC/C=C(\C(=O)OC)c1csc(N=CN(C)C)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d6dd7437a4df4e30817c1c6d65d25c7d | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | C(O)([O-])=O.[Na+].C(C)(=O)OCC.C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N=CN(C)C)=O.S(O)(O)(=O)=O>>C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N)=O | CN(C)C=[N:20][c:19]1[s:18][cH:17][c:16](/[C:4](=[N:3]/[O:2][CH3:1])[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:21]1>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][s:18][c:19]([NH2:20])[n:21]1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | null | null | CO | Deprotection | OtherReaction | 33bcd42056000f3bc2d5907a85ff371ecf8a91697366ae3c95c7cdc536f4e4f7 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | N=C(C(=O)NCCc1ccccc1)c1cscn1 | C-N(-C)-C=[N;H0;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 95.8 | [{"value": 95.0, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | (Z)-N-(2-phenylethyl)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetamide (130 mg, 0.36 mmol) was dissolved in 4 ml of methanol, followed by the addition of 0.5 ml of 1.8N sulfuric acid. The mixture so obtained was stirred for 3 days at room temperature. The reaction mixture was then added with 20 ml... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | null | null | c1ccccc1.c1cscn1 | Other | CO | null | 72 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>CO>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8963643bac2048a9a944f4a1f3c4252e | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | C(O)([O-])=O.[Na+].C(C)(=O)OCC.C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N=CN(C)C)=O.Cl>>C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N)=O | CN(C)C=[N:20][c:19]1[s:18][cH:17][c:16](/[C:4](=[N:3]/[O:2][CH3:1])[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:21]1>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][s:18][c:19]([NH2:20])[n:21]1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | null | null | CO | Deprotection | OtherReaction | 33bcd42056000f3bc2d5907a85ff371ecf8a91697366ae3c95c7cdc536f4e4f7 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | N=C(C(=O)NCCc1ccccc1)c1cscn1 | C-N(-C)-C=[N;H0;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 97.7 | [{"value": 97.5, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.7, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | (Z)-N-(2-Phenylethyl)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetamide (130 mg, 0.36 mmol) was dissolved in 4 ml of methanol, followed by the addition of 1 ml of 2 N hydrochloric acid. The mixture so obtained was stirred at 60° C. for 3 hours and 30 minutes. The reaction mixture was then added wit... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | null | null | c1ccccc1.c1cscn1 | Other | CO | 60 | 0.5 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>CO>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bccf734719ee4e03a13a60243dc65238 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | C(=O)O.O.C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N=CN(C)C)=O.C(O)([O-])=O.[Na+]>>C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N)=O | CN(C)C=[N:20][c:19]1[s:18][cH:17][c:16](/[C:4](=[N:3]/[O:2][CH3:1])[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:21]1>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][s:18][c:19]([NH2:20])[n:21]1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | null | null | CO.C(C)(=O)OCC | Deprotection | OtherReaction | 33bcd42056000f3bc2d5907a85ff371ecf8a91697366ae3c95c7cdc536f4e4f7 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | N=C(C(=O)NCCc1ccccc1)c1cscn1 | C-N(-C)-C=[N;H0;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 57.9 | [{"value": 57.9, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | (Z)-N-(2-Phenylethyl)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetamide (130 mg, 0.36 mmol) was dissolved in 4 ml of methanol, followed by the addition of 0.5 ml of formic acid and 1 ml of water. The mixture so obtained was stirred at 60° C. for 3 hours and 30 minutes. The reaction mixture was then... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | null | null | c1ccccc1.c1cscn1 | Other | CO.C(C)(=O)OCC | 60 | 0.5 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>CO.C(C)(=O)OCC>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4094125384014bf38c8f542f3d52bf4f | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | [Cl-].[NH4+].C(Cl)Cl.[OH-].[Na+].C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N=CN(C)C)=O>>C1(=CC=CC=C1)CCNC(\C(=N/OC)\C=1N=C(SC1)N)=O | CN(C)C=[N:20][c:19]1[s:18][cH:17][c:16](/[C:4](=[N:3]/[O:2][CH3:1])[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:21]1>>[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[NH:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][s:18][c:19]([NH2:20])[n:21]1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 | null | null | CO | Deprotection | OtherReaction | 33bcd42056000f3bc2d5907a85ff371ecf8a91697366ae3c95c7cdc536f4e4f7 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | N=C(C(=O)NCCc1ccccc1)c1cscn1 | C-N(-C)-C=[N;H0;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 82.1 | [{"value": 81.8, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.1, "product": "C1(=CC=CC=C1)CCNC(\\C(=N/OC)\\C=1N=C(SC1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | (Z)-N-(2-Phenylethyl)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetamide (130 mg, 0.36 mmol) was dissolved in 4 ml of methanol, followed by the addition of 1 ml of a 1N aqueous solution of sodium hydroxide. The mixture so obtained was stirred at room temperature for 2 days. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | null | null | c1ccccc1.c1cscn1 | Other | CO | null | 48 | CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N=CN(C)C)n1>CO>CO/N=C(\C(=O)NCCc1ccccc1)c1csc(N)n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-69960a002bb1481596e42a63ec2dd704 | COc1cc(N)c(N)cc1OC.O=C(O)C(=O)O>>COc1cc2[nH]c(=O)c(=O)[nH]c2cc1OC | NC1=C(C=C(C(=C1)OC)OC)N.C(C(=O)O)(=O)O>>COC=1C=C2NC(C(NC2=CC1OC)=O)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:12]([NH2:11])[cH:13][c:14]1[O:15][CH3:16].O[C:7](=[O:8])[C:9](O)=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[nH:6][c:7](=[O:8])[c:9](=[O:10])[nH:11][c:12]2[cH:13][c:14]1[O:15][CH3:16] | COc1cc(N)c(N)cc1OC.O=C(O)C(=O)O | COc1cc2[nH]c(=O)c(=O)[nH]c2cc1OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:4]=[c;H0;D3;+0:3]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:1]:1=[O;D1;H0:2] | null | [] | null | null | null | null | 6,7-Dimethoxy-1,4-dihydroquinoxaline-2,3-dione was prepared from 1,2-dimethoxybenzene. Nitration of 1,2-dimethoxybenzene gave 1,2-dimethoxy-4,5-dinitrobenzene, which was reduced to 1,2-diamino-4,5-dimethoxybenzene. Condensation of the diamine with oxalic acid gave 6,7-dimethoxy-1,4-dihydroquinoxaline-2,3-dione. ##STR31... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | null | null | null | COc1cc(N)c(N)cc1OC.O=C(O)C(=O)O>>COc1cc2[nH]c(=O)c(=O)[nH]c2cc1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8a253bdb1e143b2ae6d02ae88447cf5 | C[O-].O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O>>COc1c(Cl)cc2c(c1[N+](=O)[O-])=NC(=O)C(=O)N=2 | ClC1=C(C(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-])F.C[O-].[Na+]>>ClC=1C(=C(C2=NC(C(N=C2C1)=O)=O)[N+](=O)[O-])OC | [CH3:1][O-:2].F[c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([c:9]1[N+:10](=[O:11])[O-:12])[nH:13][c:14](=[O:15])[c:16](=[O:17])[nH:18]2>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([c:9]1[N+:10](=[O:11])[O-:12])=[N:13][C:14](=[O:15])[C:16](=[O:17])[N:18]=2 | C[O-].O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O | COc1c(Cl)cc2c(c1[N+](=O)[O-])=NC(=O)C(=O)N=2 | null | null | null | Protection | OtherReaction | a7d76c2a6bfdd138babfd395a211f1e275b9bcf1d4bcb24c8cd20882f7161f6c | 29fc5779163b01c4d317ea64bb5a1fa8b0f020fb7a365acf4aa351c7d5296f72 | O=C1N=c2ccccc2=NC1=O | F-[c;H0;D3;+0:1]1:[c:2](-[Cl;D1;H0:3]):[c:4]:[c;H0;D3;+0:5]2:[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[c;H0;D3;+0:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c;H0;D3;+0:12]:2:[c:13]:1-[#7;+:14].[C;D1;H3:15]-[O-;H0;D1:16]>>[#7;+:14]-[c:13]1:[c;H0;D3;+0:1](-[O;H0;D2;+0:16]-[C;D1;H3:15]):[c:2](-[Cl;D1;H0:3]):[c:4]:[c;H0;D3;+0:5]2:[... | null | [] | null | null | null | null | Similarly, the reaction of 7-chloro-6-fluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dione with sodium methoxide gave 7-chloro-6-methoxy-5-nitroquinoxaline-2,3-dione, and with ethanethiol gave 7-chloro-6-ethylthio-5-nitroquinoxaline-2,3-dione.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | C1=CNc2ccccc2N1 | c1ccc2c(c1)=NCCN=2 | c1ccc2c(c1)=NCCN=2 | HF | null | null | null | C[O-].O=c1[nH]c2cc(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O>>COc1c(Cl)cc2c(c1[N+](=O)[O-])=NC(=O)C(=O)N=2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3cc03fd3884c4b61ab9530f4f144bf4b | Nc1cc(F)c(F)cc1[N+](=O)[O-]>>Nc1cc(F)c(F)cc1N | FC1=CC(=C(C=C1)N)N.FC1=CC(=C(C=C1)N)N.[Cl-].[Cl-].[Ca+2].FC1=CC(=C(N)C=C1F)[N+](=O)[O-]>>FC1=CC(=C(C=C1F)N)N | O=[N+:10]([O-])[c:9]1[c:2]([NH2:1])[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8]1>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8][c:9]1[NH2:10] | Nc1cc(F)c(F)cc1[N+](=O)[O-] | Nc1cc(F)c(F)cc1N | null | [Zn] | O.CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 67.3 | [{"value": 67.3, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4,5-Difluoro-1,2-diaminobenzene was prepared using an adaptation of the method of Tsuji et al., (Tsuji, Y. et al., J. Org. Chem. 55:580 (1990)). Zn powder (942 mg, 14.4 mmol), CaCl2 (94.4 mg), H2O (1.0 mL) and 4.0 mL EtOH were combined and brought to reflux as described for 4-fluoro-1,2-diaminobenzene (see Example 11) ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Zn].O.CCO | null | null | Nc1cc(F)c(F)cc1[N+](=O)[O-]>[Zn].O.CCO>Nc1cc(F)c(F)cc1N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-86b392d03e2846528aa1fa65dbd1be47 | CCOC(=O)C(=O)OCC.Nc1cc(F)c(F)cc1N>>O=c1[nH]c2cc(F)c(F)cc2[nH]c1=O | C(C(=O)OCC)(=O)OCC.FC1=CC(=C(C=C1F)N)N>>FC=1C=C2NC(C(NC2=CC1F)=O)=O | CCO[C:2](=[O:1])[C:13](OCC)=[O:14].[NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[NH2:12]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]2[nH:12][c:13]1=[O:14] | CCOC(=O)C(=O)OCC.Nc1cc(F)c(F)cc1N | O=c1[nH]c2cc(F)c(F)cc2[nH]c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 97e21139ecefaa04a2e379ed0dfebec189c2701deff8c9503bbfc28454aa8630 | c8ccb70449d522f01766cc73ad4a0b9615cb3862df314fa00223145fc838cd64 | O=c1[nH]c2ccccc2[nH]c1=O | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=[O;D1;H0:4])-O-C-C.[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | null | [] | null | null | null | null | The title compound (Sarges, R. et al., J. Med. Chem. 33:2240 (1990)) was prepared using an adaptation of the method of Cheeseman. (Cheeseman, G. W. H. J. Chem. Soc. 1171 (1962)). A mixture of diethyl oxalate (1.11 g, 7.63 mmol and 4,5-difluoro-1,2-diaminobenzene (110 mg, 0.763 mmol) was heated to reflux under N2 for 2 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | null | null | null | CCOC(=O)C(=O)OCC.Nc1cc(F)c(F)cc1N>>O=c1[nH]c2cc(F)c(F)cc2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3a55073e62434c55a2982297e6aefec4 | Nc1cc(F)c(F)c(F)c1N.O=C(O)C(=O)O>>O=c1[nH]c2cc(F)c(F)c(F)c2[nH]c1=O | C(C)O.FC=1C(=C(C=C(C1F)F)N)N.C(C(=O)O)(=O)O>>FC1=C2NC(C(NC2=CC(=C1F)F)=O)=O | [NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]1[NH2:13].O[C:2](=[O:1])[C:14](O)=[O:15]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]2[nH:13][c:14]1=[O:15] | Nc1cc(F)c(F)c(F)c1N.O=C(O)C(=O)O | O=c1[nH]c2cc(F)c(F)c(F)c2[nH]c1=O | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 36 | [{"value": 36.0, "product": "FC1=C2NC(C(NC2=CC(=C1F)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.0, "product": "FC1=C2NC(C(NC2=CC(=C1F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a brown solution of 3,4,5-trifluoro-1,2-phenylenediamine (285 mg, 1.75 mmol) in aqueous 2N HCl (10 mL) is added oxalic acid (221 mg, 1.75 mmol). The brown mixture is brought to reflux and stirred under N2 overnight. The mixture is filtered to yield 139 mg (37%) of crude title compound. An analytical sample is prepar... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | Cl | null | 8 | Nc1cc(F)c(F)c(F)c1N.O=C(O)C(=O)O>Cl>O=c1[nH]c2cc(F)c(F)c(F)c2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-25c1c2e595e141d09b33471fe1808e8d | O=[N+]([O-])[O-].O=c1[nH]c2cc(F)c(F)c(F)c2[nH]c1=O>>O=c1[nH]c2c(F)c(F)c(F)c([N+](=O)[O-])c2[nH]c1=O | FC1=C2NC(C(NC2=CC(=C1F)F)=O)=O.S(O)(O)(=O)=O.[N+](=O)([O-])[O-].[K+]>>[N+](=O)([O-])C1=C2NC(C(NC2=C(C(=C1F)F)F)=O)=O | [O-][N+:12](=[O:13])[O-:14].[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:7]([F:8])[c:9]([F:10])[c:11]([F:6])[c:15]2[nH:16][c:17]1=[O:18]>>[O:1]=[c:2]1[nH:3][c:4]2[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[c:15]2[nH:16][c:17]1=[O:18] | O=[N+]([O-])[O-].O=c1[nH]c2cc(F)c(F)c(F)c2[nH]c1=O | O=c1[nH]c2c(F)c(F)c(F)c([N+](=O)[O-])c2[nH]c1=O | null | null | null | Functional Group Interconversion | Aromatic nitration with NO3 salt | 9b381d098dcad5196b132a57d8e96dee6d17d216c4112b0363cc96bfbd7d28da | 0ce6037a9929cfde4fb0319b5ea6c7a5e61c11a2cadf28ca4b1b99abfaf70590 | O=c1[nH]c2ccccc2[nH]c1=O | [F;D1;H0:1]-[c:2]1:[c:3](-[F;D1;H0:4]):[cH;D2;+0:5]:[c:6]2:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:2:[c;H0;D3;+0:12]:1-[F;H0;D1;+0:13].[O-]-[N+;H0;D3:14](-[O;-;D1;H0:15])=[O;D1;H0:16]>>[F;D1;H0:1]-[c:2]1:[c:3](-[F;D1;H0:4]):[c;H0;D3;+0:5](-[F;H0;D1;+0:13]):[c:6]2:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:2:[c;H0;D3;+0:12]:1-... | null | [] | null | null | 8 | HOUR | To 5,6,7-trifluoro-1,4-dihydro-2,3-quinoxalinedione (93 mg, 0.43 mmol) is added concentrated sulfuric acid (0.5 mL). While the flask is in an ice bath, KNO3 is slowly added, giving a brown mixture, which is stirred overnight. The reaction mixture, now dark red, is then added to ice water (5 mL), instantly giving an ora... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitrate | Aromatic halide.Nitro group | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | null | null | 8 | O=[N+]([O-])[O-].O=c1[nH]c2cc(F)c(F)c(F)c2[nH]c1=O>>O=c1[nH]c2c(F)c(F)c(F)c([N+](=O)[O-])c2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-80600a2229cb427eb0740b402c5fba7d | O=C(Nc1ccc(F)c(Cl)c1F)C(F)(F)F.O=[N+]([O-])O>>O=C(Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F)C(F)(F)F | [N+](=O)(O)[O-].ClC=1C(=C(C=CC1F)NC(C(F)(F)F)=O)F.[N+](=O)(O)[O-]>>ClC=1C(=C(C(=CC1F)[N+](=O)[O-])NC(C(F)(F)F)=O)F | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:9][c:10]([F:11])[c:12]([Cl:13])[c:14]1[F:15])[C:16]([F:17])([F:18])[F:19].O[N+:6](=[O:7])[O-:8]>>[O:1]=[C:2]([NH:3][c:4]1[c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]([F:11])[c:12]([Cl:13])[c:14]1[F:15])[C:16]([F:17])([F:18])[F:19] | O=C(Nc1ccc(F)c(Cl)c1F)C(F)(F)F.O=[N+]([O-])O | O=C(Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F)C(F)(F)F | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[#7:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[#7:6]-[C:5]=[O;D1;H0:4]):[c:8] | 95 | [{"value": 95.0, "product": "ClC=1C(=C(C(=CC1F)[N+](=O)[O-])NC(C(F)(F)F)=O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 15.1 g (58.1 mmol) of 3-chloro-2,4-difluoro-(trifluoroacetamido)benzene in 80 mL of H2SO4 kept in an ice-bath was added dropwise 10 mL of HNO3. Solid precipitate was observed during addition of HNO3. The mixture was stirred in an ice-bath for 4 h, then added to 600 mL of ice-water. The precipitate was ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | OS(=O)(=O)O | null | 4 | O=C(Nc1ccc(F)c(Cl)c1F)C(F)(F)F.O=[N+]([O-])O>OS(=O)(=O)O>O=C(Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F)C(F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c0b2172acf044bee8060c3836fd1650a | O=C(Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F)C(F)(F)F>>Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F | ClC=1C(=C(C(=CC1F)[N+](=O)[O-])NC(C(F)(F)F)=O)F>>ClC=1C(=C(N)C(=CC1F)[N+](=O)[O-])F | O=C(C(F)(F)F)[NH:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([F:9])[c:10]([Cl:11])[c:12]1[F:13]>>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([F:9])[c:10]([Cl:11])[c:12]1[F:13] | O=C(Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F)C(F)(F)F | Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F | null | null | C(=O)([O-])[O-].[K+].[K+].CO.O | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1ccccc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 6.9 | [{"value": 6.9, "product": "ClC=1C(=C(N)C(=CC1F)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6.35 g (20.8 mmol) of 3-chloro-2,4-difluoro-6-nitro-(trifluoroacetamido)benzene in 60 mL of 7% K2CO3 methanol/water (3:2) was stirred at 25° C. for 4 h. The solution was evaporated to remove the methanol. Solid was observed in the residue. It was filtered, washed with water, and dried to leave 301 mg of a... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1ccccc1 | Other | C(=O)([O-])[O-].[K+].[K+].CO.O | null | null | O=C(Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F)C(F)(F)F>C(=O)([O-])[O-].[K+].[K+].CO.O>Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3cada9c9acb74b5d838041f2015ca3bb | Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F>>Nc1cc(F)c(Cl)c(F)c1N | ClC=1C(=C(N)C(=CC1F)[N+](=O)[O-])F.Cl[Sn]Cl>>ClC1=C(C(=C(C=C1F)N)N)F | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[c:6]([Cl:7])[c:8]([F:9])[c:10]1[NH2:11]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([Cl:7])[c:8]([F:9])[c:10]1[NH2:11] | Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F | Nc1cc(F)c(Cl)c(F)c1N | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.6 | [{"value": 95.0, "product": "ClC1=C(C(=C(C=C1F)N)N)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "ClC1=C(C(=C(C=C1F)N)N)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 348 mg (1.67 mmol) of 3-chloro-2,4-difluoro-6-nitroaniline and 1.57 g (8.28 mmol) of SnCl2 in 8 mL of ethanol was heated at 70° C. for 2 h. The solution was evaporated to remove the ethanol. The residue was treated with 2N NaOH to pH=13. White precipitate was observed. The mixture was extracted with CHCl3... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | null | Nc1c([N+](=O)[O-])cc(F)c(Cl)c1F>C(C)O>Nc1cc(F)c(Cl)c(F)c1N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c565455ebe624ff695bd4f3f0a89e4d7 | Nc1cc(F)c(Cl)c(F)c1N.O=C(O)C(=O)O>>O=c1[nH]c2cc(F)c(Cl)c(F)c2[nH]c1=O | ClC1=C(C(=C(C=C1F)N)N)F.C(C(=O)O)(=O)O>>ClC=1C(=C2NC(C(NC2=CC1F)=O)=O)F | [NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([Cl:9])[c:10]([F:11])[c:12]1[NH2:13].O[C:2](=[O:1])[C:14](O)=[O:15]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[c:8]([Cl:9])[c:10]([F:11])[c:12]2[nH:13][c:14]1=[O:15] | Nc1cc(F)c(Cl)c(F)c1N.O=C(O)C(=O)O | O=c1[nH]c2cc(F)c(Cl)c(F)c2[nH]c1=O | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 82 | [{"value": 82.0, "product": "ClC=1C(=C2NC(C(NC2=CC1F)=O)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "ClC=1C(=C2NC(C(NC2=CC1F)=O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 230 mg (1.29 mmol) of 4-chloro-3,5-difluoro-1,2-phenylenediamine and 125 mg (1.38 mmol) of oxalic acid in 4 mL of 2N HCl was refluxed for 3 h and cooled to room temperature. The mixture was filtered, washed with water, and dried to leave a brown solid (245 mg, 82%); mp>250° C.; 1H NMR (DMSO-d6), 6.921 (d, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | Cl | null | null | Nc1cc(F)c(Cl)c(F)c1N.O=C(O)C(=O)O>Cl>O=c1[nH]c2cc(F)c(Cl)c(F)c2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8da99543e0364674abc4d6f1dbd12299 | O=[N+]([O-])[O-].O=c1[nH]c2cc(F)c(Cl)c(F)c2[nH]c1=O>>O=c1[nH]c2c(F)c(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O | ClC=1C(=C2NC(C(NC2=CC1F)=O)=O)F.[N+](=O)([O-])[O-].[K+].[N+](=O)([O-])[O-].[K+]>>ClC1=C(C(=C2NC(C(NC2=C1F)=O)=O)[N+](=O)[O-])F | [O-][N+:12](=[O:13])[O-:14].[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:9]([F:10])[c:7]([Cl:8])[c:11]([F:6])[c:15]2[nH:16][c:17]1=[O:18]>>[O:1]=[c:2]1[nH:3][c:4]2[c:5]([F:6])[c:7]([Cl:8])[c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[c:15]2[nH:16][c:17]1=[O:18] | O=[N+]([O-])[O-].O=c1[nH]c2cc(F)c(Cl)c(F)c2[nH]c1=O | O=c1[nH]c2c(F)c(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O | null | null | OS(=O)(=O)O | Functional Group Interconversion | Aromatic nitration with NO3 salt | bdc7586a693070879fbbcb7ac36c4ca1147950a00c707c57a6b53f196453fef2 | a6e75bd3b480911aeca325a734424f30acd0183ae8bf9859f205a30a2d946dc4 | O=c1[nH]c2ccccc2[nH]c1=O | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[c;H0;D3;+0:3](-[F;H0;D1;+0:4]):[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:[cH;D2;+0:11]:[c;H0;D3;+0:12]:1-[F;D1;H0:13].[O-]-[N+;H0;D3:14](-[O;-;D1;H0:15])=[O;D1;H0:16]>>[Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[c;H0;D3;+0:11](-[F;H0;D1;+0:4]):[c:10]2:[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:2:[c;H0;D3;+... | 65 | [{"value": 65.0, "product": "ClC1=C(C(=C2NC(C(NC2=C1F)=O)=O)[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "ClC1=C(C(=C2NC(C(NC2=C1F)=O)=O)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 120 mg (5.16 mmol) of 6-chloro-5,7-difluoro-1,4-dihydroquinoxaline-2,3-dione in 1 mL of H2SO4 (97%) kept in an ice bath was added portionwise 60 mg (0.59 mmol) of KNO3. The solution was stirred at room temperature for 14 h and 60 mg of KNO3 was added. It was stirred at room temperature for 24 h, then d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Nitrate | Aromatic halide.Aromatic halide.Aromatic halide.Nitro group | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | OS(=O)(=O)O | null | 14 | O=[N+]([O-])[O-].O=c1[nH]c2cc(F)c(Cl)c(F)c2[nH]c1=O>OS(=O)(=O)O>O=c1[nH]c2c(F)c(Cl)c(F)c([N+](=O)[O-])c2[nH]c1=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2af234bdce2f49bd88878ea3885cee0f | O=C(Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-])C(F)(F)F>>Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-] | FC1=CC(=C(C(=C1)[N+](=O)[O-])NC(C(F)(F)F)=O)[N+](=O)[O-]>>FC1=CC(=C(N)C(=C1)[N+](=O)[O-])[N+](=O)[O-] | O=C(C(F)(F)F)[NH:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([F:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14]>>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][c:8]([F:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | O=C(Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-])C(F)(F)F | Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-] | null | null | C(=O)([O-])[O-].[K+].[K+] | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1ccccc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 52.2 | [{"value": 52.0, "product": "FC1=CC(=C(N)C(=C1)[N+](=O)[O-])[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "FC1=CC(=C(N)C(=C1)[N+](=O)[O-])[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-fluoro-2,6-dinitro-(trifluoroacetamido)benzene (297 mg, 1.00 mmol) in 10% K2CO3 (10 mL) was refluxed for 1 h, then cooled to room temperature to give yellow crystals. It was filtered and washed with cold water (2×1 mL), affording 105 mg (52%) of the title compound. 1H NMR (DMSO-d6): δ8.254 (s, 2H), 8.46... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1ccccc1 | Other | C(=O)([O-])[O-].[K+].[K+] | null | null | O=C(Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-])C(F)(F)F>C(=O)([O-])[O-].[K+].[K+]>Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5f0ef1fe42bf4089bfdb32856a06d1da | Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-]>>Nc1cc(F)cc([N+](=O)[O-])c1N | FC1=CC(=C(N)C(=C1)[N+](=O)[O-])[N+](=O)[O-].CCO>>NC1=C(C=C(C=C1[N+](=O)[O-])F)N | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]1[NH2:12]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]1[NH2:12] | Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-] | Nc1cc(F)cc([N+](=O)[O-])c1N | null | null | O | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 50 | [{"value": 50.0, "product": "NC1=C(C=C(C=C1[N+](=O)[O-])F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "NC1=C(C=C(C=C1[N+](=O)[O-])F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-fluoro-2,6-dinitroaniline (125 mg, 0.62 mmole) in freshly prepared 6% (NH4)2S (5 mL) and EtOH (5 mL) was refluxed for 30 min, diluted with water (10 mL) and kept at 4° C. for several hours. The precipitate was collected and washed with cold water (2×1 mL), affording 53 mg (50%) of 1,2-diamino-4-fluoro-6... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | O | null | null | Nc1c([N+](=O)[O-])cc(F)cc1[N+](=O)[O-]>O>Nc1cc(F)cc([N+](=O)[O-])c1N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5f3c86c86c224a99bae8cd6ed4600e41 | Nc1cc(F)cc([N+](=O)[O-])c1N.O=C(O)C(=O)O>>O=c1[nH]c2cc(F)cc([N+](=O)[O-])c2[nH]c1=O | NC1=C(C=C(C=C1[N+](=O)[O-])F)N.O.O.C(C(=O)O)(=O)O>>FC1=CC(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-] | [NH2:3][c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[NH2:14].O[C:2](=[O:1])[C:15](O)=[O:16]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]2[nH:14][c:15]1=[O:16] | Nc1cc(F)cc([N+](=O)[O-])c1N.O=C(O)C(=O)O | O=c1[nH]c2cc(F)cc([N+](=O)[O-])c2[nH]c1=O | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | c86e58e5de9d81a144b6b41f680eb7659186c7868f08e5aac1617724bf77eb2d | 7638e82fa21608897e39fce0230ec3ea8d25eb3dc2c5eca945d0fbdce3af493b | O=c1[nH]c2ccccc2[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 43.5 | [{"value": 42.0, "product": "FC1=CC(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.5, "product": "FC1=CC(=C2NC(C(NC2=C1)=O)=O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-diamino-4-fluoro-6-nitrobenzene (80 mg, 0.46 mmole) and oxalic acid dihydrate (70 mg, 0.56 mmole, used as received) in 4N HCl (4 mL) was refluxed at 120°-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the supernatant was removed. The yellow solid was washed with cold wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | C1=CNc2ccccc2N1 | C1=CNc2ccccc2N1 | HO- | Cl | null | null | Nc1cc(F)cc([N+](=O)[O-])c1N.O=C(O)C(=O)O>Cl>O=c1[nH]c2cc(F)cc([N+](=O)[O-])c2[nH]c1=O |
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