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-02ee2261663048188cf6d85d2cc96e3f | ord-441df664c30c4a9e9bf4d09ba8dd20c5 | CC(=O)OC(C)=O.CN(CN(CN(CO)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]>>CC(=O)OCN(CN(CN(C)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] | C(C)(=O)[O-].CN(CN(CN(CO)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-].S(=O)(=O)([O-])[O-].CC(=O)OC(=O)C.CN1CCC(=C2C3=CC=CC=C3C=CC4=CC=CC=C42)CC1.[N+](=O)([O-])[O-].CC(=O)OC(=O)C.[N+](=O)(O)[O-].[N+](=O)(O)[O-].CN(CN(CN(CO)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-].C(C)(=O)[O-].[N+](=O)(O)[O-]>>C(C)(=O)OCN(CN(CN(C)[N+](=O)[O-])[N... | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][N:6]([CH2:7][N:8]([CH2:9][N:10]([CH3:11])[N+:12](=[O:13])[O-:14])[N+:15](=[O:16])[O-:17])[N+:18](=[O:19])[O-:20]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][N:6]([CH2:7][N:8]([CH2:9][N:10]([CH3:11])[N+:12](=[O:13])[O-:14])[N+:15](=[O:16])[O-:17])[N+:18](=[O:19])[O-:20] | CC(=O)OC(C)=O.CN(CN(CN(CO)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] | CC(=O)OCN(CN(CN(C)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] | null | null | O.CC(=O)O | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | null | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;+:4]-[#7:5]-[C:6]-[OH;D1;+0:7]>>[#7;+:4]-[#7:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 15 | MINUTE | "Acetate or nitrate of 6-alkyl-2,4,6-trinitro-2,4,6-triazahexanol. Jiri Denkstein and Vladimir Kaderabek. Czech. 98,248, Jan. 15, 1961, Appl. Nov. 13, 1959. The described method is the nitrolysis of N-alkylhexamethylene-tetraminium nitrate, sulfate, or acetate with a mixt. of HNO3 with Ac2O, or anhydride of HNO3. Thus,... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | null | HO- | O.CC(=O)O | null | 0.25 | CC(=O)OC(C)=O.CN(CN(CN(CO)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]>O.CC(=O)O>CC(=O)OCN(CN(CN(C)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-89e0dd8d586746a0a5ae5e0d0dd64837 | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl>>ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl | [OH-].[Na+].[Cl-].CC(CCCCCCCCCCC[NH2+]CC1=CC=CC=C1)C.ClC1=C(C=CC=C1)C(C(Cl)(Cl)Cl)C1=C(C=CC=C1)Cl>>ClC1=C(C=CC=C1)C(=C(Cl)Cl)C1=C(C=CC=C1)Cl | Cl[C:2]([Cl:1])([Cl:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[Cl:1][C:2]([Cl:3])=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18] | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl | ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl | null | null | ClC1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | caa8b2a9f44558fc059d965cc9d934c6f352d3b95cd1d0c82b06e08395a08f42 | 0dd848f795fd5d379d1f2d3c82454c9c78fe869578925aa1f2c7dab7a9bf4faa | C=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D4;+0:1](-[Cl;D1;H0:2])(-[Cl;D1;H0:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1](-[Cl;D1;H0:3])=[C;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 97.8 | [{"value": 97.8, "product": "ClC1=C(C=CC=C1)C(=C(Cl)Cl)C1=C(C=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 201.5 g of 28% strength aqueous sodium hydroxide and 2.0 g of dimethyllaurylbenzylammonium chloride were added to a solution of 250 g of 1,1-bis(chlorophenyl)-2,2,2-trichloroethane in 100 g of monochlorobenzene at 50° C. The mixture was heated at reflux (90° C.) for 20 hours. The organic phase was separated by phase se... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group | Alkenyl halide.Alkenyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | ClC1=CC=CC=C1 | 90 | null | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl>ClC1=CC=CC=C1>ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-14dbf4ab6e104d8e99acc3f339bbd870 | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl>>ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl | [Cl-].CC(CCCCCCCCCCC[NH2+]CC1=CC=CC=C1)C.ClC1=C(C=CC=C1)C(C(Cl)(Cl)Cl)C1=C(C=CC=C1)Cl.[OH-].[Na+].[Cl-].CC(CCCCCCCCCCC[NH2+]CC1=CC=CC=C1)C.ClC1=C(C=CC=C1)C(C(Cl)(Cl)Cl)C1=C(C=CC=C1)Cl>>ClC1=C(C=CC=C1)C(=C(Cl)Cl)C1=C(C=CC=C1)Cl | Cl[C:2]([Cl:1])([Cl:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[Cl:1][C:2]([Cl:3])=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18] | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl | ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl | null | null | null | Functional Group Interconversion | OtherReaction | caa8b2a9f44558fc059d965cc9d934c6f352d3b95cd1d0c82b06e08395a08f42 | 0dd848f795fd5d379d1f2d3c82454c9c78fe869578925aa1f2c7dab7a9bf4faa | C=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D4;+0:1](-[Cl;D1;H0:2])(-[Cl;D1;H0:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1](-[Cl;D1;H0:3])=[C;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | null | [] | 93 | CELSIUS | null | null | 150 g of solid 1,1-bis(chlorophenyl)-2,2,2-trichloroethane were added to 248.8 g of a 27.2% strength aqueous sodium hydroxide solution maintained at 93° C. 1.4 g of dimethyllaurylbenzylammonium chloride were added thereto. The temperature increased from 93° to 103° C. The addition of solid 1,1-bis(chlorophenyl)-2,2,2-t... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group | Alkenyl halide.Alkenyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | null | 93 | null | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl>>ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e272024058c04429a4fb231ad4f05a1a | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl>>ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl | ClC1=C(C=CC=C1)C(C(Cl)(Cl)Cl)C1=C(C=CC=C1)Cl.[Cl-].C[NH+](CCCCCCCCCCCCCC1=CC=CC=C1)C>>ClC1=C(C=CC=C1)C(=C(Cl)Cl)C1=C(C=CC=C1)Cl | Cl[C:2]([Cl:1])([Cl:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[Cl:1][C:2]([Cl:3])=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18] | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl | ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl | null | null | null | Functional Group Interconversion | OtherReaction | caa8b2a9f44558fc059d965cc9d934c6f352d3b95cd1d0c82b06e08395a08f42 | 0dd848f795fd5d379d1f2d3c82454c9c78fe869578925aa1f2c7dab7a9bf4faa | C=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D4;+0:1](-[Cl;D1;H0:2])(-[Cl;D1;H0:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1](-[Cl;D1;H0:3])=[C;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | 2 | HOUR | 990 kg of solid 1,1-bis(chlorophenyl)-2,2,2-trichloroethane were charged into the basic aqueous phase emanating from an upstream dehydrochlorination operation. The charging period was 2 hours to avoid the formation of solid masses inside the reactor. 5 kg of dimethylbenzyllaurylammonium chloride were added, while inten... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group | Alkenyl halide.Alkenyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | 2 | Clc1ccccc1C(c1ccccc1Cl)C(Cl)(Cl)Cl>>ClC(Cl)=C(c1ccccc1Cl)c1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-075e43a27a3840418219bfac37a86eef | CCOC([O-])([O-])[O-].COC(=O)c1cccc(N)c1NCc1ccc(-c2ccccc2C#N)cc1>>CCOc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2C#N)cc1 | NC=1C(=C(C(=O)OC)C=CC1)NCC1=CC=C(C=C1)C1=C(C=CC=C1)C#N.C(C)(=O)O.C(OCC)([O-])([O-])[O-]>>C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=O)OC)OCC | [O-][C:4]([O-])([O-])[O:3][CH2:2][CH3:1].[NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]1[NH:16][CH2:17][c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]#[N:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:... | CCOC([O-])([O-])[O-].COC(=O)c1cccc(N)c1NCc1ccc(-c2ccccc2C#N)cc1 | CCOc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2C#N)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1c82f9fe3cfc3b18658219069b0c75c5f00845a2be973ef1af40947107e12f85 | 9fed8bfa1c36edcd110a3822d99da6cce41017b125d3759f9e9691b9b4858f6a | c1ccc(-c2ccc(Cn3cnc4ccccc43)cc2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[NH;D2;+0:6]-[C:7]-[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11].[C:12]-[#8:13]-[C;H0;D4;+0:14](-[O-])(-[O-])-[O-]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:9](:[c:11]):[n;H0;D2;+0:10]:[c;H0;D3;+0:14](-[#8:13]-[C:12]):[n;H0;D3;+0:6]:1-[C:7]-[c:8] | null | [] | 80 | CELSIUS | 1 | HOUR | To a solution of methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate (2.03 g) in ethyl orthocarbonate (5 ml) was added acetic acid (0.37 g), and the mixture was stirred for one hour at 80° C. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Secondary amine | Ether | c1ccccc1 | c1nc2ccccc2[nH]1 | c1nc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | HO- | null | 80 | 1 | CCOC([O-])([O-])[O-].COC(=O)c1cccc(N)c1NCc1ccc(-c2ccccc2C#N)cc1>>CCOc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3530d84ddd434b9796c4ba61b9c55ed4 | Cc1ccc(-c2ccccc2C(=O)O)cc1.N#C[S-]>>COC(=S)NC(=O)c1ccccc1-c1ccc(C)cc1 | [S-]C#N.[K+].CC1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)O.S(=O)(Cl)Cl.O1CCOCC1>>CC1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)NC(OC)=S | O[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]1.[C:3]([S-:4])#[N:5]>>[CH3:1][O:2][C:3](=[S:4])[NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]1 | Cc1ccc(-c2ccccc2C(=O)O)cc1.N#C[S-] | COC(=S)NC(=O)c1ccccc1-c1ccc(C)cc1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | 5796d38a08898f0c5968fd307a856a69cf326a3925d1104e20c7cfba53072c24 | dd6a04c6f58a6026296803bf75f982d6d88b902d05694bf74e898d0f019805f4 | c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[S-;H0;D1:8]>>[C;D1;H3:9]-[#8:10]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | In chloroform (40 ml) was dissolved (4'-methylbiphenyl-2-yl)carboxylic acid (10 g). To the solution was added thionyl chloride (7 ml), and the mixture was heated for 3 hours under reflux. The reaction mixture was poured into ice-water, then the organic layer was separated, washed with water and concentrated to dryness ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile | Ether.Thioamide.Secondary amide | null | null | c1ccccc1.c1ccccc1 | null | C(Cl)(Cl)Cl | null | null | Cc1ccc(-c2ccccc2C(=O)O)cc1.N#C[S-]>C(Cl)(Cl)Cl>COC(=S)NC(=O)c1ccccc1-c1ccc(C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0808b584fdb544f4a1f143dc72e645d9 | Cc1cccc(-c2ccccc2)c1C(=O)O.NN>>Cc1ccc(-c2ccccc2C(=O)NN)cc1 | CC1=C(C(=CC=C1)C1=CC=CC=C1)C(=O)O.C(C(=O)Cl)(=O)Cl.O.NN>>CC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)NN | O[C:12]([c:11]1[c:2]([CH3:1])[cH:9][cH:8][cH:7][c:6]1-[c:5]1[cH:4][cH:3][cH:10][cH:17][cH:16]1)=[O:13].[NH2:14][NH2:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12](=[O:13])[NH:14][NH2:15])[cH:16][cH:17]1 | Cc1cccc(-c2ccccc2)c1C(=O)O.NN | Cc1ccc(-c2ccccc2C(=O)NN)cc1 | null | CN(C=O)C | O.O1CCCC1 | Acylation | OtherReaction | 75ca53d50f06e653cfb6c4e4b5b47c4771c72c87ba9e08de37a38e153b19773f | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4](-[c:5]2:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[c:10]:2):[c:11]:[c:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14]:1-[C;D1;H3:15].[N;D1;H2:16]-[NH2;D1;+0:17]>>[C;D1;H3:15]-[c;H0;D3;+0:14]1:[cH;D2;+0:7]:[c:6]:[c:5](-[c:4]2:[c:11]:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:8]:[c;H0;D3;+0:... | 63 | [{"value": 63.0, "product": "CC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)NN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "CC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)NN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 4,-methylbiphenyl-2-carboxylic acid (6.4 g) in tetrahydrofuran (50 ml) were added N,N-dimethylformamide (two drops) and oxalyl chloride (4.4 g). The mixture was stirred for 16 hours at room temperature. The solvent was evaporated to dryness under reduced pressure to give an oil, which was added dropwis... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CN(C=O)C.O.O1CCCC1 | null | 16 | Cc1cccc(-c2ccccc2)c1C(=O)O.NN>CN(C=O)C.O.O1CCCC1>Cc1ccc(-c2ccccc2C(=O)NN)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7fd1326482284a269e6950009ded5e4a | CCSc1nc2c(C(=O)OC)sc(C)c2[nH]1.ClC(Cl)(Cl)c1nc(-c2ccccc2-c2ccc(CBr)cc2)no1>>CCSc1nc2c(C)sc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2noc(C(Cl)(Cl)Cl)n2)cc1 | [H-].[Na+].ClC(C1=NC(=NO1)C1=C(C=CC=C1)C1=CC=C(C=C1)CBr)(Cl)Cl.O.C(C)SC=1NC=2C(N1)=C(SC2C)C(=O)OC>>C(C)SC1=NC=2C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NOC(=N1)C(Cl)(Cl)Cl)=C(SC2C)C(=O)OC | [CH3:1][CH2:2][S:3][c:4]1[n:5][c:6]2[c:7]([C:11](=[O:12])[O:13][CH3:14])[s:9][c:10]([CH3:8])[c:15]2[nH:16]1.Br[CH2:17][c:18]1[cH:19][cH:20][c:21](-[c:27]2[c:22](-[c:28]3[n:29][o:30][c:31]([C:32]([Cl:33])([Cl:34])[Cl:35])[n:36]3)[cH:23][cH:24][cH:25][cH:26]2)[cH:37][cH:38]1>>[CH3:1][CH2:2][S:3][c:4]1[n:5][c:6]2[c:7]([CH... | CCSc1nc2c(C(=O)OC)sc(C)c2[nH]1.ClC(Cl)(Cl)c1nc(-c2ccccc2-c2ccc(CBr)cc2)no1 | CCSc1nc2c(C)sc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2noc(C(Cl)(Cl)Cl)n2)cc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 3d46a936f2ae59670ce4e5e8ad8b7f72eff878eb93e0dab71b6ecb7cbb27d145 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(-c2ncon2)c(-c2ccc(Cn3cnc4cscc43)cc2)c1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2-[c;H0;D3;+0:12]2:[#7;a:13]:[#8;a:14]:[c:15](-[C:16]):[#7;a:17]:2):[c:18]:[c:19]:1.[#16:20]-[c:21]1:[#7;a:22]:[c:23]2:[c:24](:[nH;D2;+0:25]:1):[c;H0;D3;+0:26](-[CH3;D1;+0:27]):[#16;a:28]:[c;H0;D3;+0:29]:2-[C;H0... | 58 | [{"value": 58.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To an ice-cooling solution of methyl 2-ethylthio-4-methylthieno[3,4-d]imidazole-6-carboxylate (3 g) in DMF (20 ml) was added sodium hydride (60%, oil) (0.56 g), and the mixture was stirred for 10 minutes. To the ice-cooling mixture was added [2'-(5-trichloromethyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl bromide (6.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1nc2cscc2[nH]1.c1ccccc1.c1ncon1.c1ccccc1 | c1nc2cscc2[nH]1.c1ccccc1.c1ccccc1.c1ncon1 | c1nc2cscc2[nH]1.c1ccccc1.c1ccccc1.c1ncon1 | HBr | CN(C)C=O | null | 0.166667 | CCSc1nc2c(C(=O)OC)sc(C)c2[nH]1.ClC(Cl)(Cl)c1nc(-c2ccccc2-c2ccc(CBr)cc2)no1>CN(C)C=O>CCSc1nc2c(C)sc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2noc(C(Cl)(Cl)Cl)n2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-931de3348ab940248d69c90b7b2859d7 | CCCCc1nc2ccccc2n1Cc1ccc(-c2ccccc2C(=O)O)cc1>>CCCCc1nc2ccccc2n1Cc1ccc(-c2ccccc2CO)cc1 | Cl.C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)O)C=CC=C2>>C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)CO)C=CC=C2 | O=[C:25]([c:24]1[c:19](-[c:18]2[cH:17][cH:16][c:15]([CH2:14][n:13]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]4[cH:8][cH:9][cH:10][cH:11][c:12]43)[cH:28][cH:27]2)[cH:20][cH:21][cH:22][cH:23]1)[OH:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1[CH2:14][c:15]1[cH:16][cH:17][c:... | CCCCc1nc2ccccc2n1Cc1ccc(-c2ccccc2C(=O)O)cc1 | CCCCc1nc2ccccc2n1Cc1ccc(-c2ccccc2CO)cc1 | null | null | C1=CC=CC=C1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(-c2ccc(Cn3cnc4ccccc43)cc2)cc1 | 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] | 46.4 | [{"value": 46.0, "product": "C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)CO)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)CO)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A stirred solution of 2-butyl-1-[(2'-carboxy-biphenyl-4-yl)methyl]benzimidazole (1.50 g) in benzene (30 ml) was added dropwise to sodium dihydro-bis(2-methoxyethoxy)aluminate (70% toluene solution). The mixture was stirred for one hour at room temperature, and then heated for 10 minutes under reflux. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1nc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | C1=CC=CC=C1 | null | 1 | CCCCc1nc2ccccc2n1Cc1ccc(-c2ccccc2C(=O)O)cc1>C1=CC=CC=C1>CCCCc1nc2ccccc2n1Cc1ccc(-c2ccccc2CO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b2e4e352ee244261996ff42a33ea5c0d | Cc1ccc(-c2ccccc2C#N)cc1.NO>>Cc1cccc(-c2ccccc2)c1C(N)=NO | Cl.NO.C[O-].[Na+].CS(=O)C.[Na].C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)C>>CC1=C(C(=CC=C1)C1=CC=CC=C1)C(N)=NO | [CH3:1][c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][cH:3][cH:2][c:13]2[C:14]#[N:15])[cH:12][cH:11]1.[NH2:16][OH:17]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]1[C:14]([NH2:15])=[N:16][OH:17] | Cc1ccc(-c2ccccc2C#N)cc1.NO | Cc1cccc(-c2ccccc2)c1C(N)=NO | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | eb24e2851be51ffcfe59c6db165204b760855b20be2d560f467b9dafe4f41c95 | ad3f1127a4d99506976df608684863fb1e08b35faede2d4e31cf4ca96393cd2e | c1ccc(-c2ccccc2)cc1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[N;H0;D1;+0:7]#[C;H0;D2;+0:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13].[NH2;D1;+0:14]-[O;D1;H1:15]>>[CH3;D1;+0:1]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](-[C;H0;D3;+0:8](-[NH2;D1;+0:7])=[N;H0;D2;+0:14]-[O;D1;H1:15]):[c:10].[c:4]:[c:3]:[cH;D2;+0:2]:[c:5]:[c:6] | 96 | [{"value": 96.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of hydroxylamine hydrochloride (17.9 g) in dimethyl sulfoxide (120 ml) was added a methanol solution of sodium methoxide prepared from metallic sodium (5.92 g) and anhydrous methanol (50 ml). The mixture was stirred for 10 minutes at room temperature, to which was added 2'-cyano-4-methylbiphenyl (10 g) Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine.Oxime | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | CO | null | 0.166667 | Cc1ccc(-c2ccccc2C#N)cc1.NO>CO>Cc1cccc(-c2ccccc2)c1C(N)=NO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fe2c423b7f1a4089bbabfe77f305ed3e | CCCCc1nc(Cl)c(C=O)[nH]1.O=c1oc(-c2ccccc2-c2ccc(CBr)cc2)nn1C(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCc1nc(Cl)c(C=O)n1Cc1ccc(-c2ccccc2-c2n[nH]c(=O)o2)cc1 | BrCC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN(C(O1)=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)C=1NC(=C(N1)Cl)C=O.[H-].[Na+]>>C(CCC)C=1N(C(=C(N1)Cl)C=O)CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NNC(O1)=O | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH:10]=[O:11])[nH:12]1.Br[CH2:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2-[c:24]2[n:25][n:26](C(c3ccccc3)(c3ccccc3)c3ccccc3)[c:27](=[O:28])[o:29]2)[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH:10]=... | CCCCc1nc(Cl)c(C=O)[nH]1.O=c1oc(-c2ccccc2-c2ccc(CBr)cc2)nn1C(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCc1nc(Cl)c(C=O)n1Cc1ccc(-c2ccccc2-c2n[nH]c(=O)o2)cc1 | null | null | CN(C=O)C.O.FC(C(=O)O)(F)F | Heteroatom Alkylation and Arylation | OtherReaction | 320602f6f56ab5d62544c064302a25b6424fb1ba317a93985e4adb5b0c05874a | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]nc(-c2ccccc2-c2ccc(Cn3ccnc3)cc2)o1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#8;a:7]:[c:8]:[#7;a:9]:[n;H0;D3;+0:10]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C:11]-[c:12]1:[#7;a:13]:[c:14](-[Cl;D1;H0:15]):[c:16](-[C:17]=[O;D1;H0:18]):[nH;D2;+0:19]:1>>[C:11]-[c:12]1:[#7;a:13]:[c:14](-[Cl;D1;H0:15]):[c:16](-[C:17]=[O;D1;H0:18]):... | 27.6 | [{"value": 27.0, "product": "C(CCC)C=1N(C(=C(N1)Cl)C=O)CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NNC(O1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.6, "product": "C(CCC)C=1N(C(=C(N1)Cl)C=O)CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NNC(O1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To an ice-cooling solution of 2-butyl-4-chloroimidazole-5-carbaldehyde (0.19 g) in N,N-dimethylformamide (1 ml) was added sodium hydride (60% in oil; 44 mg), and the mixture was stirred for 10 minutes. To the mixture was then added 5-(4'-bromomethylbipenyl-2-yl-)-2,3-dihydro-3-triphenylmethyl-1,3,4-oxadiazol-2-one (0.5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1.c1nnco1.c1ccccc1.c1ccccc1.c1ccccc1 | c1c[nH]cn1.c1nnco1 | c1c[nH]cn1.c1ccccc1.c1ccccc1.c1nnco1 | HBr | CN(C=O)C.O.FC(C(=O)O)(F)F | null | 0.166667 | CCCCc1nc(Cl)c(C=O)[nH]1.O=c1oc(-c2ccccc2-c2ccc(CBr)cc2)nn1C(c1ccccc1)(c1ccccc1)c1ccccc1>CN(C=O)C.O.FC(C(=O)O)(F)F>CCCCc1nc(Cl)c(C=O)n1Cc1ccc(-c2ccccc2-c2n[nH]c(=O)o2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-183122e9f21147948277859f6c856c2c | CCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1>>CCCc1nc2cccc(C(=O)O)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1 | O=C1N=C(NO1)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=O)OC)CCC.[OH-].[Na+].Cl>>O=C1N=C(NO1)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=O)O)CCC | C[O:13][C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]2[n:5][c:4]([CH2:3][CH2:2][CH3:1])[n:15]([CH2:16][c:17]3[cH:18][cH:19][c:20](-[c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]4-[c:27]4[n:28][c:29](=[O:30])[o:31][nH:32]4)[cH:33][cH:34]3)[c:14]21)=[O:12]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])... | CCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1 | CCCc1nc2cccc(C(=O)O)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1nc(-c2ccccc2-c2ccc(Cn3cnc4ccccc43)cc2)[nH]o1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 90 | [{"value": 90.0, "product": "O=C1N=C(NO1)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=O)O)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "O=C1N=C(NO1)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=O)O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | A mixture of methyl 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]-2-propylbenzimidazole-7-carboxylate (703 mg) in 0.3N-NaOH (12 ml) was stirred at 60° C. for one hour, and then adjusted to pH 3 with 0.1N-HCl. Resulting precipitates were extracted with a mixture of chloroform-ethanol (10:1; 150 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1nc2ccccc2[nH]1.c1ccccc1.c1ccccc1.c1ncon1 | Other | null | 60 | 1 | CCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1>>CCCc1nc2cccc(C(=O)O)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d43f11dc297541b8b35b7cb26b75eb7f | CCCc1nc2cccc(C(=S)OC)c2n1Cc1ccc(-c2ccccc2C#N)cc1.NO>>CCCc1nc2cccc(C(=S)OC)c2n1Cc1ccc(-c2ccccc2C(=N)NO)cc1 | Cl.NO.C(C)N(CC)CC.O1CCCC1.C(#N)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=S)OC)CCC>>ONC(=N)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=S)OC)CCC | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][c:10]([C:11](=[S:12])[O:13][CH3:14])[c:15]2[n:16]1[CH2:17][c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]#[N:29])[cH:32][cH:33]1.[NH2:30][OH:31]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][c:10]([C:11](=[S:12])[O:13][CH... | CCCc1nc2cccc(C(=S)OC)c2n1Cc1ccc(-c2ccccc2C#N)cc1.NO | CCCc1nc2cccc(C(=S)OC)c2n1Cc1ccc(-c2ccccc2C(=N)NO)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccc(-c2ccc(Cn3cnc4ccccc43)cc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | 76 | [{"value": 76.0, "product": "ONC(=N)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=S)OC)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "ONC(=N)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2=C1C(=CC=C2)C(=S)OC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of hydroxylamine hydrochloride (20.85 g) in DMSO (200 ml) was added triethylamine (3.9 g) and the mixture was stirred for 30 minutes at room temperatures. To the reaction mixture was added the compound (16 g) obtained in Example (34c), and the mixture was stirred for 60 hours at 70° C. To the resultant mi... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1nc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | null | CS(=O)C | null | 0.5 | CCCc1nc2cccc(C(=S)OC)c2n1Cc1ccc(-c2ccccc2C#N)cc1.NO>CS(=O)C>CCCc1nc2cccc(C(=S)OC)c2n1Cc1ccc(-c2ccccc2C(=N)NO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5a8b07a85d754ba09f86d8772e993268 | COC(=O)c1sc(C)c(N)c1N.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>COC(=O)c1sc(C)c2[nH]c(=O)[nH]c12 | NC1=C(SC(=C1N)C)C(=O)OC.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>CC=1SC(=C2NC(NC21)=O)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7]([CH3:8])[c:9]([NH2:10])[c:14]1[NH2:13].ClC(Cl)(Cl)O[C:11](OC(Cl)(Cl)Cl)=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7]([CH3:8])[c:9]2[nH:10][c:11](=[O:12])[nH:13][c:14]12 | COC(=O)c1sc(C)c(N)c1N.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | COC(=O)c1sc(C)c2[nH]c(=O)[nH]c12 | null | null | CN(C=O)C.ClCCl | Aromatic Heterocycle Formation | OtherReaction | 97701edb31809d581f7901188ddfc9b22ef49a19c096aa8679980f510f0fd61a | a45bcfc67f492c2bcbbcd6aea1a3ecbcd02016481f8d3076a9f9433abd46ae0d | O=c1[nH]c2cscc2[nH]1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[#16;a:7]:[c:8](-[C;D1;H3:9]):[c:10](-[NH2;D1;+0:11]):[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[#16;a:7]:[c:8](-[C;D1;H3:9]):[c:10]2:[nH;D2;+0:11]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:13]:[c:12]:1:2 | 4,777.4 | [{"value": 53.0, "product": "CC=1SC(=C2NC(NC21)=O)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4777.4, "product": "CC=1SC(=C2NC(NC21)=O)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Methyl 3,4-diamino-5-methylthiophene-2-carboxylate (3.0 g) was dissolved in a mixture of N,N-dimethyl formamide (5 ml) and dichloromethane (15 ml). To the solution was added triphosgene (2.4 g) in portions. The mixture was stirred for two days at room temperature, and precipitates were collected by filtration, washed w... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine.Primary amine | null | c1ccsc1 | c1nc2cscc2[nH]1 | c1nc2cscc2[nH]1 | HCl | CN(C=O)C.ClCCl | null | 48 | COC(=O)c1sc(C)c(N)c1N.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>CN(C=O)C.ClCCl>COC(=O)c1sc(C)c2[nH]c(=O)[nH]c12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-51ddc746a7384423ae5d94dfc8ffdb86 | Cc1cccc(-c2ccccc2)c1C(=O)O>>Cc1cccc(-c2ccccc2)c1CO | C(C)(=O)OCC.O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CC1=C(C(=CC=C1)C1=CC=CC=C1)C(=O)O>>CC=1C(=C(C=CC1)C1=CC=CC=C1)CO | O=[C:14]([c:13]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[OH:15]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]1[CH2:14][OH:15] | Cc1cccc(-c2ccccc2)c1C(=O)O | Cc1cccc(-c2ccccc2)c1CO | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(-c2ccccc2)cc1 | 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] | 84.6 | [{"value": 84.0, "product": "CC=1C(=C(C=CC1)C1=CC=CC=C1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.6, "product": "CC=1C(=C(C=CC1)C1=CC=CC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To an ice-cooling suspension of lithium aluminium hydride (1.79 g) in tetrahydrofuran (50 ml) was added dropwise a solution of 4,-methylbiphenyl-2-carboxylic acid (5.0 g) in tetrahydrofuran (30 ml). The mixture was stirred for 17 hours at room temperature. To the reaction mixture were added ethyl acetate (10 ml) and wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | 17 | Cc1cccc(-c2ccccc2)c1C(=O)O>O1CCCC1>Cc1cccc(-c2ccccc2)c1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2fe8b08f64c844be852d3e2cfd2c0a0e | COC(=O)c1cccc(I)c1.Cc1ccccc1>>COC(=O)c1cccc(-c2ccc(C)cc2)c1 | IC=1C=C(C(=O)OC)C=CC1.C1(=CC=CC=C1)C>>CC1=CC=C(C=C1)C1=CC(=CC=C1)C(=O)OC | I[c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17]1.[cH:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]2)[cH:17]1 | COC(=O)c1cccc(I)c1.Cc1ccccc1 | COC(=O)c1cccc(-c2ccc(C)cc2)c1 | null | [Cu] | IC1=CC=C(C=C1)C | C-C Coupling | OtherReaction | a9eb3e90aaf615cee8625e192b3441918dcd3559ca5a74d6b87bcc8ceab889cf | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:10]:[c:9]):[c:12]:[c:13]):[c:7]:[c:8] | 29 | [{"value": 29.0, "product": "CC1=CC=C(C=C1)C1=CC(=CC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a mixture of methyl 3-iodobenzoate (26.1 g) in 4-iodotoluene (21.9 g) was added copper powder (31.8 g) gradually at 180°-190° C. The mixture was then stirred for 6 hours at 200°-210° C. The reaction mixture was cooled to room temperature, to which was added toluene. Insoluble materials were filtered off, and the fil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HI | [Cu].IC1=CC=C(C=C1)C | null | 6 | COC(=O)c1cccc(I)c1.Cc1ccccc1>[Cu].IC1=CC=C(C=C1)C>COC(=O)c1cccc(-c2ccc(C)cc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-38557339d9a449aeba84ca978a2ba6b2 | Cc1ccc(-c2ccccc2C(N)=O)cc1.O=C1CCC(=O)N1Br>>NC(=O)c1ccccc1-c1ccc(CBr)cc1 | CC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)N.BrN1C(CCC1=O)=O.CC(C)(C#N)N=NC(C)(C)C#N>>BrCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)N | [NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:16][cH:17]1.O=C1CCC(=O)N1[Br:15]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]([CH2:14][Br:15])[cH:16][cH:17]1 | Cc1ccc(-c2ccccc2C(N)=O)cc1.O=C1CCC(=O)N1Br | NC(=O)c1ccccc1-c1ccc(CBr)cc1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2ccccc2)cc1 | 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] | null | [] | null | null | 20 | HOUR | A mixture of 4'-methylbiphenyl-2-carboxamide (2.1 g), N-bromo-succinimide (2.5 g) and azobisisobutyronitrate (AIBN; 82 mg) in benzene (20 ml) was stirred for 20 hours at 60° to 70° C. Resulting crystalline precipitates were collected by filtration, washed with isopropylether and suspended in water. The suspension was s... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | 20 | Cc1ccc(-c2ccccc2C(N)=O)cc1.O=C1CCC(=O)N1Br>C1=CC=CC=C1>NC(=O)c1ccccc1-c1ccc(CBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-71fc841a6d9944a2bee1d36da445a3d0 | COC(=O)c1cccc([N+](=O)[O-])c1NC(=O)OC(C)(C)C.NC(=O)c1ccccc1-c1ccc(CBr)cc1>>COC(=O)c1cccc([N+](=O)[O-])c1N(Cc1ccc(-c2ccccc2C(N)=O)cc1)C(=O)OC(C)(C)C | O.C(C)(C)(C)OC(=O)NC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-].BrCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)N.C(=O)([O-])[O-].[K+].[K+]>>C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C(N)=O)C1=C(C(=O)OC)C=CC=C1[N+](=O)[O-] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[NH:14][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37].Br[CH2:15][c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]([NH2:27])=[O:28])[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8]... | COC(=O)c1cccc([N+](=O)[O-])c1NC(=O)OC(C)(C)C.NC(=O)c1ccccc1-c1ccc(CBr)cc1 | COC(=O)c1cccc([N+](=O)[O-])c1N(Cc1ccc(-c2ccccc2C(N)=O)cc1)C(=O)OC(C)(C)C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5da873da5e065666521679df8db5a1d2754540edd93ae40997847c9a24dedeb3 | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | c1ccc(NCc2ccc(-c3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]):[c:18]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:1... | 90 | [{"value": 90.0, "product": "C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C(N)=O)C1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.9, "product": "C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C(N)=O)C1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | null | null | A mixture of methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (1.8 g), 4'-bromomethylbiphenyl-2-carboxamide (1.8 g) and K2CO3 (0.86 g) in acetonitrile (25 ml) was heated for 6 hours under reflux. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | null | COC(=O)c1cccc([N+](=O)[O-])c1NC(=O)OC(C)(C)C.NC(=O)c1ccccc1-c1ccc(CBr)cc1>C(C)#N>COC(=O)c1cccc([N+](=O)[O-])c1N(Cc1ccc(-c2ccccc2C(N)=O)cc1)C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c6beb0e53d1f41ccadbb4bb03438fe7a | COC(=O)c1cccc([N+](=O)[O-])c1N(Cc1ccc(-c2ccccc2C(N)=O)cc1)C(=O)OC(C)(C)C>>COC(=O)c1cccc([N+](=O)[O-])c1NCc1ccc(-c2ccccc2C(N)=O)cc1 | C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C(N)=O)C1=C(C(=O)OC)C=CC=C1[N+](=O)[O-].Cl>>C(N)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)CNC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-] | CC(C)(C)OC(=O)[N:14]([c:13]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12])[CH2:15][c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]([NH2:27])=[O:28])[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[NH:14... | COC(=O)c1cccc([N+](=O)[O-])c1N(Cc1ccc(-c2ccccc2C(N)=O)cc1)C(=O)OC(C)(C)C | COC(=O)c1cccc([N+](=O)[O-])c1NCc1ccc(-c2ccccc2C(N)=O)cc1 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(NCc2ccc(-c3ccccc3)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[c:6]-[C:7](-[#8:8])=[O;D1;H0:9]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]:[c:4](-[NH;D2;+0:1]-[C:2]-[c:3]):[c:5] | 73 | [{"value": 73.0, "product": "C(N)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)CNC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "C(N)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)CNC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the compound (2.8 g) obtained in Example (54b) in methanol (15 ml) and 1N-HCl (6 ml) was heated for 2 hours under reflux. After removal of the solvent, the residue was made alkaline with an aqueous solution of NaHCO3, and the mixture was extracted with ethyl acetate. The extract was washed with water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CO | null | null | COC(=O)c1cccc([N+](=O)[O-])c1N(Cc1ccc(-c2ccccc2C(N)=O)cc1)C(=O)OC(C)(C)C>CO>COC(=O)c1cccc([N+](=O)[O-])c1NCc1ccc(-c2ccccc2C(N)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e6e2a39337d44b93874b16d5ca671d7a | CCOC(=O)ONC(=N)c1ccccc1-c1ccc(CNc2c(N)cccc2C(=O)OC)cc1.CCOC(OCC)(OCC)OCC>>CCOC(=O)ONC(=N)c1ccccc1-c1ccc(Cn2c(OCC)nc3cccc(C(=O)OC)c32)cc1 | NC=1C(=C(C(=O)OC)C=CC1)NCC1=CC=C(C=C1)C1=C(C=CC=C1)C(NOC(=O)OCC)=N.C(C)OC(OCC)(OCC)OCC.C(C)(=O)O>>C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C(NOC(=O)OCC)=N)C(=CC=C2)C(=O)OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6][NH:7][C:8](=[NH:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1-[c:16]1[cH:17][cH:18][c:19]([CH2:20][NH:21][c:36]2[c:27]([NH2:26])[cH:28][cH:29][cH:30][c:31]2[C:32](=[O:33])[O:34][CH3:35])[cH:37][cH:38]1.CCO[C:22](OCC)(OCC)[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6]... | CCOC(=O)ONC(=N)c1ccccc1-c1ccc(CNc2c(N)cccc2C(=O)OC)cc1.CCOC(OCC)(OCC)OCC | CCOC(=O)ONC(=N)c1ccccc1-c1ccc(Cn2c(OCC)nc3cccc(C(=O)OC)c32)cc1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | f196cb4012ed9537782b4276968f18ea4ce5e73c589b0baf71bb23b250a1b916 | bd232e1dd2be9d3110126569a0f1bc99a7dae874a4678f830fc394771f299877 | c1ccc(-c2ccc(Cn3cnc4ccccc43)cc2)cc1 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[#8:2]-[C:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[C:10]-[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8]1:[c:12](:[c:14]):[n;H0;D2;+0:13]:[c;H0;D3;+0:1](-[#8:2]-[C:3]):[n;H0;D3;+0:9]:1-[C:10]-[c:11] | null | [] | 100 | CELSIUS | 2 | HOUR | The pale brown syrup (8.58 g) obtained in Example (57a) was dissolved in dioxane (20 ml). To the solution were added tetraethoxymethane (8.64 g) and acetic acid (1.56 g). The mixture was stirred for 2 hours at 100° C. The reaction mixture was concentrated to dryness. The residue was crystallized from ethyl acetate (50 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether.Primary amine.Secondary amine | Ether | c1ccccc1 | c1nc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1nc2ccccc2[nH]1 | HO- | O1CCOCC1 | 100 | 2 | CCOC(=O)ONC(=N)c1ccccc1-c1ccc(CNc2c(N)cccc2C(=O)OC)cc1.CCOC(OCC)(OCC)OCC>O1CCOCC1>CCOC(=O)ONC(=N)c1ccccc1-c1ccc(Cn2c(OCC)nc3cccc(C(=O)OC)c32)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3e74301d3a61478689a392b6ec496f3b | CCOC(=O)ONC(=N)c1ccccc1-c1ccc(Cn2c(OCC)nc3cccc(C(=O)OC)c32)cc1>>CCOc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1 | C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C(NOC(=O)OCC)=N)C(=CC=C2)C(=O)OC.N12CCCCCC2=NCCC1>>C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C=1NOC(N1)=O)C(=CC=C2)C(=O)OC | CCO[C:30](=[O:31])[O:32][NH:33][C:28]([c:27]1[c:22](-[c:21]2[cH:20][cH:19][c:18]([CH2:17][n:16]3[c:4]([O:3][CH2:2][CH3:1])[n:5][c:6]4[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]43)[cH:35][cH:34]2)[cH:23][cH:24][cH:25][cH:26]1)=[NH:29]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]... | CCOC(=O)ONC(=N)c1ccccc1-c1ccc(Cn2c(OCC)nc3cccc(C(=O)OC)c32)cc1 | CCOc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | e0bdeb42d4421f80f022d6fc32581ec41e15f40f497e4a8ba221eab767f54c2e | 9e3d09592f5ede9055ffd931dc5f712e01861d7e32ba50f8819bee685355e605 | O=c1nc(-c2ccccc2-c2ccc(Cn3cnc4ccccc43)cc2)[nH]o1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[NH;D1;+0:6])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[c:11]):[c:12]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:5](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[c:11]):[c:12]):[nH;D2;+0:4]:[o;H0;D2;+0:3]:1 | 57.6 | [{"value": 45.0, "product": "C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C=1NOC(N1)=O)C(=CC=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "C(C)OC1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C=1NOC(N1)=O)C(=CC=C2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | The crude crystals (4.0 g) obtained in Example (57b) was dissolved in ethyl acetate (50 ml). To the solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 3.2 g), and the mixture was stirred for 2 hours at 80° C. The reaction mixture was partitioned between ethyl acetate (50 ml) and 1N HCl (20 ml). The organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | null | null | c1ncon1 | c1nc2ccccc2[nH]1.c1ccccc1.c1ccccc1.c1ncon1 | HO- | C(C)(=O)OCC | 80 | 2 | CCOC(=O)ONC(=N)c1ccccc1-c1ccc(Cn2c(OCC)nc3cccc(C(=O)OC)c32)cc1>C(C)(=O)OCC>CCOc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9265263c0e12469ebf21fb271fd6edfd | CCCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2C(=N)NOC(C)=O)cc1.S=C=S>>CCCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=S)o[nH]2)cc1 | C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C(NOC(C)=O)=N)C(=CC=C2)C(=O)OC.C(=S)=S.[H-].[Na+]>>C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C=1NOC(N1)=S)C(=CC=C2)C(=O)OC | C[C:31](=O)[O:33][NH:34][C:29]([c:28]1[c:23](-[c:22]2[cH:21][cH:20][c:19]([CH2:18][n:17]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]4[cH:8][cH:9][cH:10][c:11]([C:12](=[O:13])[O:14][CH3:15])[c:16]43)[cH:36][cH:35]2)[cH:24][cH:25][cH:26][cH:27]1)=[NH:30].S=C=[S:32]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][c... | CCCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2C(=N)NOC(C)=O)cc1.S=C=S | CCCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=S)o[nH]2)cc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | f4a2ce55911049c1bf3b0585e975062b146e88fd51ae6c1059989e3177541774 | 750b75c1687c01863ae19efa51b87813d8251d239764f045babc1fff46c54852 | S=c1nc(-c2ccccc2-c2ccc(Cn3cnc4ccccc43)cc2)[nH]o1 | C-[C;H0;D3;+0:1](=O)-[O;H0;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[NH;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]):[c:11].S=C=[S;H0;D1;+0:12]>>[S;H0;D1;+0:12]=[c;H0;D3;+0:1]1:[n;H0;D2;+0:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[c:10]):[c:11]):[nH;D2;+0:3]:[o;H0;D2;+0:2]:1 | 32 | [{"value": 32.0, "product": "C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C=1NOC(N1)=S)C(=CC=C2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.0, "product": "C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C=1NOC(N1)=S)C(=CC=C2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of methyl 2-butyl-1-[[2'-(acetoxycarbamimidoyl)biphenyl-4yl)methyl]benzimidazole-7-carboxylate (2.0 g) and CS2 (1.5 g) in DMF (12 ml) gas added sodium hydride (60% in oil, 0.56 g) during a period of 10 minutes and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was po... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Thiocarbonyl | null | c1ncon1 | c1nc2ccccc2[nH]1.c1ccccc1.c1ccccc1.c1ncon1 | Other | CN(C)C=O | null | 2 | CCCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2C(=N)NOC(C)=O)cc1.S=C=S>CN(C)C=O>CCCCc1nc2cccc(C(=O)OC)c2n1Cc1ccc(-c2ccccc2-c2nc(=S)o[nH]2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-167fda6db42f40c2b04d4c02c0deb86d | O.c1ccc(OCC2CO2)cc1>>OCC(O)COc1ccccc1 | C(C1CO1)OC1=CC=CC=C1.O1CC1.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1=CC=CC=2SC3=CC=CC=C3NC12>>O(C1=CC=CC=C1)CC(CO)O | [OH2:1].[CH2:2]1[CH:3]([CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[O:4]1>>[OH:1][CH2:2][CH:3]([OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | O.c1ccc(OCC2CO2)cc1 | OCC(O)COc1ccccc1 | null | [Br-].C(CC)[N+](CCC)(CCC)CCC | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 49f0d8aa533a65bde4caf2b7dfb137ed678780e9ba31fda30002c409b4eb3eb4 | b1bb21d4df12989b465bb7166cc1a8f21724ee35a0f7d0ba675fa6599c63ef8d | c1ccccc1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[OH2;D0;+0:5]>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[OH;D1;+0:5] | null | [] | null | null | 6 | HOUR | A solution of 150.2 g. phenyl glycidyl ether (1.0 eq.), 200.0 g. AOnPA (1.15 eq., of Example 1), 200.0 g. toluene, 4.0 g. tetrapropylammonium bromide (0.015 eq.), and 1.0 g. phenothiazine was heated at reflux for 6.0 hours. Conversion, measured by residual oxirane titer, was ca. 93%. Upon cooling, the reactor was charg... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol.Secondary alcohol | C1CO1 | null | c1ccccc1 | null | [Br-].C(CC)[N+](CCC)(CCC)CCC.C1(=CC=CC=C1)C | null | 6 | O.c1ccc(OCC2CO2)cc1>[Br-].C(CC)[N+](CCC)(CCC)CCC.C1(=CC=CC=C1)C>OCC(O)COc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3ef2cd7b916a450b941ab84417ba43f7 | CCCCCCOc1ccc(OCCCCCC(=O)O)cc1.Cl.O=C1COC(=O)C1>>O=C(CCCCCOc1ccc(Cl)cc1)C1=C(O)COC1=O | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCCC)OC1=CC=C(OCCCCCC(=O)O)C=C1.Cl>>OC1=C(C(OC1)=O)C(CCCCCOC1=CC=C(C=C1)Cl)=O | CCCCCCO[c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](O)=[O:1])[cH:15][cH:14]1.[ClH:13].[CH2:16]1[C:17](=[O:18])[CH2:19][O:20][C:21]1=[O:22]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[C:16]1=[C:17]([OH:18])[CH2:19][O:20][C:21]1=[O:2... | CCCCCCOc1ccc(OCCCCCC(=O)O)cc1.Cl.O=C1COC(=O)C1 | O=C(CCCCCOc1ccc(Cl)cc1)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | CCOCC | Acylation | OtherReaction | 1bfcb98c1d530cd290ea76be256ecd05669b091d13977d6c899356e22cc32ad8 | 4305578bce974d2abbb356d5d8728ecece7752bfbc31d2edba7c4c465b3ae8ce | O=C(CCCCCOc1ccccc1)C1=CCOC1=O | C-C-C-C-C-C-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]-[C:9].[ClH;D0;+0:10].[O;D1;H0:11]=[C:12]1-[#8:13]-[C:14]-[C;H0;D3;+0:15](=[O;H0;D1;+0:16])-[CH2;D2;+0:17]-1>>[C:9]-[C:8]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C;H0;D3;+0:17]1=[C;H0;D3;+0:15](-[OH;D1;+0:16])-[C:14]-[#8:13]-[C:12]-1=[O;D1... | 43 | [{"value": 43.0, "product": "OC1=C(C(OC1)=O)C(CCCCCOC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.0, "product": "OC1=C(C(OC1)=O)C(CCCCCOC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a stirring solution of 554 mg (5.54 mmol) of tetronic acid in 20 mL of diemthylformamide is added 850 μL (6.09 mmol) of triethylamine and 220 mg (1.765 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.26 g (6.63 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.475 g (6.63 mmol) of 6-[4-(he... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ester.Ether | Aromatic halide.Ketone.Ester.Enol | c1ccccc1.C1CCOC1 | c1ccccc1.C1=CCOC1 | c1ccccc1.C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CCOCC | null | 48 | CCCCCCOc1ccc(OCCCCCC(=O)O)cc1.Cl.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CCOCC>O=C(CCCCCOc1ccc(Cl)cc1)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-74d123cdf41747398dd804672189e4fd | CCCC/C=C\CCCCCCCC(=O)O.O=C1COC(=O)C1>>CCCC/C=C\CCCCCCCC(=O)C1=C(O)COC1=O | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCCCCC\C=C/CCCC)(=O)O.Cl>>OC1=C(C(OC1)=O)C(CCCCCCC\C=C/CCCC)=O | O[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][CH3:1])=[O:15].[CH2:16]1[C:17](=[O:18])[CH2:19][O:20][C:21]1=[O:22]>>[CH3:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[C:16]1=[C:17]([OH:18])[CH2:19][O:20][C:21... | CCCC/C=C\CCCCCCCC(=O)O.O=C1COC(=O)C1 | CCCC/C=C\CCCCCCCC(=O)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C.CO.C(C)(=O)OCC | C-C Coupling | OtherReaction | 15f3304ec355e6fae5bb90bae6b36a89baad3bf259dbcee9cf11733ab1cc8fc4 | 1eaefd43aa20304b18998f5790ec5413e598d7869b87589e6ad9c00e178e5f4e | O=C1C=CCO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#8:7]-[C:6]-1=[O;D1;H0:5] | 82 | [{"value": 82.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCC\\C=C/CCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "OC1=C(C(OC1)=O)C(CCCCCCC\\C=C/CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a stirring solution of 111 mg (1.11 mmol) of tetronic acid in 5 mL of dimethylformamide is added 185 μL (1.33 mmol) of triethylamine and 100 mg of 4-dimethylaminopyridine at 0° C. Next, 303 mg (1.33 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 300 mg (1.33 mmol) of myristoleic acid are ad... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Ester.Enol | C1CCOC1 | C1=CCOC1 | C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC | null | 72 | CCCC/C=C\CCCCCCCC(=O)O.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC>CCCC/C=C\CCCCCCCC(=O)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a7cf8eaa48de44358d5af939538ff052 | CCCCCC/C=C\CCCCCCCC(=O)O.O=C1COC(=O)C1>>CCCCCC/C=C\CCCCCCCC(=O)C1=C(O)COC1=O | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCCCCC\C=C/CCCCCC)(=O)O.Cl>>OC1=C(C(OC1)=O)C(CCCCCCC\C=C/CCCCCC)=O | O[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].[CH2:18]1[C:19](=[O:20])[CH2:21][O:22][C:23]1=[O:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:18]1=[C... | CCCCCC/C=C\CCCCCCCC(=O)O.O=C1COC(=O)C1 | CCCCCC/C=C\CCCCCCCC(=O)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C.CO.C(C)(=O)OCC | C-C Coupling | OtherReaction | 15f3304ec355e6fae5bb90bae6b36a89baad3bf259dbcee9cf11733ab1cc8fc4 | 1eaefd43aa20304b18998f5790ec5413e598d7869b87589e6ad9c00e178e5f4e | O=C1C=CCO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#8:7]-[C:6]-1=[O;D1;H0:5] | 36 | [{"value": 36.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCC\\C=C/CCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCC\\C=C/CCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a stirring solution of 1.07 g (10.72 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.64 mL (11.97 mmol) of triethylamine and 428 mg of 4-dimethylaminopyridine at 0° C. Next, 2.44 g (12.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.0 g (11.79 mmol) of palmitoleic acid a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Ester.Enol | C1CCOC1 | C1=CCOC1 | C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC | null | 72 | CCCCCC/C=C\CCCCCCCC(=O)O.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC>CCCCCC/C=C\CCCCCCCC(=O)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f12c4fbe7adb4fc78bb8a1f8fb817f95 | CCCCCCCCC#CCCCCCCCC(=O)O.O=C1COC(=O)C1>>CCCCCCCCC#CCCCCCCCC(=O)C1=C(O)COC1=O | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.CCCCCCCCC#CCCCCCCCC(=O)O.Cl>>OC1=C(C(OC1)=O)C(CCCCCCCC#CCCCCCCCC)=O | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]#[C:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[CH2:20]1[C:21](=[O:22])[CH2:23][O:24][C:25]1=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][... | CCCCCCCCC#CCCCCCCCC(=O)O.O=C1COC(=O)C1 | CCCCCCCCC#CCCCCCCCC(=O)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C.CO.C(C)(=O)OCC | C-C Coupling | OtherReaction | 15f3304ec355e6fae5bb90bae6b36a89baad3bf259dbcee9cf11733ab1cc8fc4 | 1eaefd43aa20304b18998f5790ec5413e598d7869b87589e6ad9c00e178e5f4e | O=C1C=CCO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#8:7]-[C:6]-1=[O;D1;H0:5] | 56 | [{"value": 56.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCCC#CCCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCCC#CCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 1.62 g (17.86 mmol) of tetronic acid in 50 mL of dimethylformamide is added 2.5 mL (17.86 mmol) of triethylamine and 652 mg of 4-dimethylaminopyridine at 0° C. Next, 3.71 g (19.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.86 mmol) of stearolic acid are ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Ester.Enol | C1CCOC1 | C1=CCOC1 | C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC | null | 8 | CCCCCCCCC#CCCCCCCCC(=O)O.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC>CCCCCCCCC#CCCCCCCCC(=O)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86ae5c67c1df403db2f7cf7d7103c33f | CCCCCCCCCCCCCCCCCC(=O)Cl.O=C1COC(=O)C1>>CCCCCCCCCCCCCCCCCC(=O)C1=C(O)COC1=O | Cl.C1C(=O)COC1=O.C(C)N(CC)CC.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCCCC)=O | Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[CH2:20]1[C:21](=[O:22])[CH2:23][O:24][C:25]1=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C... | CCCCCCCCCCCCCCCCCC(=O)Cl.O=C1COC(=O)C1 | CCCCCCCCCCCCCCCCCC(=O)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | C(Cl)Cl.C(C)(=O)OCC | Acylation | OtherReaction | 546f90d6aca7c5bd2e7d5c0589978e61cf926ebfe62e80d839c8d659966be8a8 | ed7b1fc93b7d12b31832580112d77cb2b953e83b79192a82e46320388504dd54 | O=C1C=CCO1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#8:7]-[C:6]-1=[O;D1;H0:5] | 58 | [{"value": 58.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 1.6 g (16 mmol) of tetronic acid in 75 mL of methylene chloride is added 2.5 mL (17.86 mmol) of triethylamine and 640 mg of 4-dimethylaminopyridine at 0° C. Next, 5.0 g (17.6 mmol) of stearoyl chloride is added and the reaction is stirred overnight at room temperature. The reaction is acidifie... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone.Ester.Enol | C1CCOC1 | C1=CCOC1 | C1=CCOC1 | HCl | CN(C1=CC=NC=C1)C.C(Cl)Cl.C(C)(=O)OCC | null | 8 | CCCCCCCCCCCCCCCCCC(=O)Cl.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.C(Cl)Cl.C(C)(=O)OCC>CCCCCCCCCCCCCCCCCC(=O)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fe7b1958be8d4b2ab72860d32d3007d3 | O=C(O)CCCCCCCCOc1ccc(Cl)cc1.O=C1COC(=O)C1>>O=C(CCCCCCCCOc1ccc(Cl)cc1)C1=C(O)COC1=O | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.ClC1=CC=C(OCCCCCCCCC(=O)O)C=C1.Cl>>ClC1=CC=C(OCCCCCCCCC(=O)C=2C(OCC2O)=O)C=C1 | O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.[CH2:19]1[C:20](=[O:21])[CH2:22][O:23][C:24]1=[O:25]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1)[C:19]1=[C... | O=C(O)CCCCCCCCOc1ccc(Cl)cc1.O=C1COC(=O)C1 | O=C(CCCCCCCCOc1ccc(Cl)cc1)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C.CO.C(C)(=O)OCC | Acylation | OtherReaction | 83372693035b8fa3e0bb8f820fc9ffbe16a82c4f9cda2e2eb10c9c9873a82f4e | e14d2b2f4de28ef7423c4b36cf2ab68d975a03db195d5781cd94844876f657bb | O=C(CCCCCCCCOc1ccccc1)C1=CCOC1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#8:7]-[C:6]-1=[O;D1;H0:5] | 30 | [{"value": 30.0, "product": "ClC1=CC=C(OCCCCCCCCC(=O)C=2C(OCC2O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.6, "product": "ClC1=CC=C(OCCCCCCCCC(=O)C=2C(OCC2O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 736 mg (7.36 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.2 mL (8.09 mmol) of triethylamine and 300 mg of 4-dimethylaminopyridine at 0° C. Next, 1.7 g (8.86 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.6 g (8.06 mmol) of 9-(4-chlorophenoxy)nonan... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Ester.Enol | C1CCOC1 | C1=CCOC1 | c1ccccc1.C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC | null | 8 | O=C(O)CCCCCCCCOc1ccc(Cl)cc1.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C.CO.C(C)(=O)OCC>O=C(CCCCCCCCOc1ccc(Cl)cc1)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-97431224e9364eb9a27d4b64804e66df | CCCCCCCc1ccc(OC(C)CCCCC(=O)O)cc1.O=C1COC(=O)C1>>CCCCCCCc1ccc(OCCCCCC(=O)C2=C(O)COC2=O)cc1 | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.Cl.CN(CCCN=C=NCC)C.C(CCCCCC)C1=CC=C(OC(CCCCC(=O)O)C)C=C1>>C(CCCCCC)C1=CC=C(OCCCCCC(=O)C=2C(OCC2O)=O)C=C1 | C[CH:13]([O:12][c:11]1[cH:10][cH:9][c:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:28][cH:27]1)[CH2:14][CH2:15][CH2:16][CH2:17][C:18](O)=[O:19].[CH2:20]1[C:21](=[O:22])[CH2:23][O:24][C:25]1=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:... | CCCCCCCc1ccc(OC(C)CCCCC(=O)O)cc1.O=C1COC(=O)C1 | CCCCCCCc1ccc(OCCCCCC(=O)C2=C(O)COC2=O)cc1 | null | CN(C1=CC=NC=C1)C | CN(C=O)C | C-C Coupling | OtherReaction | d10517cf406af99423252dac07f22e2c24f3ec220e72c05511737dab005c04f7 | ddac6a505d2ffb5f5a1d652e3d77429cdd9e20179aecc6f53ce34563b9ac242a | O=C(CCCCCOc1ccccc1)C1=CCOC1=O | C-[CH;D3;+0:1](-[#8:2]-[c:3])-[C:4]-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8](-O)=[O;D1;H0:9].[O;D1;H0:10]=[C:11]1-[#8:12]-[C:13]-[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-[CH2;D2;+0:16]-1>>[O;D1;H0:9]=[C;H0;D3;+0:8](-[C:7]-[C:6]-[C:5]-[C:4]-[CH2;D2;+0:1]-[#8:2]-[c:3])-[C;H0;D3;+0:16]1=[C;H0;D3;+0:14](-[OH;D1;+0:15])-[C:13]-[#8:12]-[C:... | 50 | [{"value": 50.0, "product": "C(CCCCCC)C1=CC=C(OCCCCCC(=O)C=2C(OCC2O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.2, "product": "C(CCCCCC)C1=CC=C(OCCCCCC(=O)C=2C(OCC2O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a stirring solution of 1.1 g (10.98 mmol) of tetronic acid in 25 mL of dimethylformamide is added 1.53 mL (10.98 mmol) of triethylamine and 400 mg of 4-dimethylaminopyridine at 0° C. Next, 2.28 g (11.98 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.38 g (10.98 mmol) of 6-(4-heptylphenoxy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Ester.Ether | Ketone.Ester.Ether.Enol | C1CCOC1 | C1=CCOC1 | c1ccccc1.C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 72 | CCCCCCCc1ccc(OC(C)CCCCC(=O)O)cc1.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C>CCCCCCCc1ccc(OCCCCCC(=O)C2=C(O)COC2=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-29b460b072c94947be0258f84aeee882 | BrCCCCOC1CCCCO1.CCCCCCCC/C=C\CCCCCCCC(=O)O>>CCCCCCCC/C=C\CCCCCCCC(=O)OCCCCOC1CCCCO1 | O.C(CCCCCCC\C=C/CCCCCCCC)(=O)O.BrCCCCOC1OCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>O1C(CCCC1)OCCCCOC(CCCCCCC\C=C/CCCCCCCC)=O | Br[CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][O:31]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]... | BrCCCCOC1CCCCO1.CCCCCCCC/C=C\CCCCCCCC(=O)O | CCCCCCCC/C=C\CCCCCCCC(=O)OCCCCOC1CCCCO1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | C1CCOCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3] | 100 | [{"value": 100.0, "product": "O1C(CCCC1)OCCCCOC(CCCCCCC\\C=C/CCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.4, "product": "O1C(CCCC1)OCCCCOC(CCCCCCC\\C=C/CCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 2.0 g (7.0 mmol) of oleic acid and 1.6 g (7.0 mmol) of 2-(4-bromobutoxy)tetrahydro-2H-pyran in 20 mL of tetrahydrofuran is added 2.3 g (7.1 mmol) of cesium carbonate and the reaction mixture is stirred overnight at room temperature. The reaction mixture is poured into water and extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | C1CCOCC1 | HBr | O1CCCC1 | null | 8 | BrCCCCOC1CCCCO1.CCCCCCCC/C=C\CCCCCCCC(=O)O>O1CCCC1>CCCCCCCC/C=C\CCCCCCCC(=O)OCCCCOC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1a0070fc523a4eb1b72811f4b40a71d5 | CC(C)(C)[Si](C)(C)OCCC/C(O)=C/O.CC(C)=CCC/C(C)=C/CBr>>CC(C)=CCC/C(C)=C/COCC(O)CCCO[Si](C)(C)C(C)(C)C | O.CC(C)(C)[Si](OCCC/C(=C/O)/O)(C)C.[H-].[Na+].C(\C=C(/C)\CCC=C(C)C)Br>>CC(C)(C)[Si](OCCCC(COC\C=C(\CCC=C(C)C)/C)O)(C)C | [OH:11]/[CH:12]=[C:13](\[OH:14])[CH2:15][CH2:16][CH2:17][O:18][Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25].Br[CH2:10]/[CH:9]=[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[CH2:10][O:11][CH2:12][CH:13]([OH:14])[CH2:15][CH2:16]... | CC(C)(C)[Si](C)(C)OCCC/C(O)=C/O.CC(C)=CCC/C(C)=C/CBr | CC(C)=CCC/C(C)=C/COCC(O)CCCO[Si](C)(C)C(C)(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 218f21babec13afce9d851f1d59ff83bd7399746428c10c2ab29ff15e9fc276a | 6a2ef7b8fc81d2146de6afe8f73ee574b66529adb9146b750e531a33ae5bdce0 | null | Br-[CH2;D2;+0:1]/[C:2]=[C:3](\[C;D1;H3:4])-[C:5]-[C:6]-[C:7]=[C:8].[C:9]-[C:10]/[C;H0;D3;+0:11](-[O;D1;H1:12])=[CH;D2;+0:13]/[OH;D1;+0:14]>>[C:9]-[C:10]-[CH;D3;+0:11](-[O;D1;H1:12])-[CH2;D2;+0:13]-[O;H0;D2;+0:14]-[CH2;D2;+0:1]/[C:2]=[C:3](\[C;D1;H3:4])-[C:5]-[C:6]-[C:7]=[C:8] | 100 | [{"value": 100.0, "product": "CC(C)(C)[Si](OCCCC(COC\\C=C(\\CCC=C(C)C)/C)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "CC(C)(C)[Si](OCCCC(COC\\C=C(\\CCC=C(C)C)/C)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirring suspension of 140 mg (4.6 mmol) of 80% NaH in 5 mL of tetrahydrofuran is added 1.07 g (4.6 mmol) of (Z)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentene-1,2-diol at 0° C. and the reaction mixture is stirred for 1 hour. Next, 1.0 g (4.6 mmol) of geranyl bromide is added and the reaction is stirred overn... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Enol.Enol | Ether.Secondary alcohol | null | null | null | Br- | O1CCCC1 | null | 1 | CC(C)(C)[Si](C)(C)OCCC/C(O)=C/O.CC(C)=CCC/C(C)=C/CBr>O1CCCC1>CC(C)=CCC/C(C)=C/COCC(O)CCCO[Si](C)(C)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a57ac03ea57a4493895ecea6566982bd | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCC)COC/C=C(\C)CC(C=C(C)C)O[Si](C)(C)C(C)(C)C>>CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCCO)COC/C=C(\C)CCC=C(C)C | C(C)(=O)OCC.CCCCCC.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.CC(C)(C)[Si](OC(C/C(=C/COCC(CCC)OC(NCCCCCCCC\C=C/CCCCCCCC)=O)/C)C=C(C)C)(C)C.O>>C\C(=C/COCC(CCCO)OC(NCCCCCCCC\C=C/CCCCCCCC)=O)\CCC=C(C)C | CC(C)(C)[Si](C)(C)[O:27][CH:35]([CH2:34]/[C:32](=[CH:31]/[CH2:30][O:29][CH2:28][CH:23]([O:22][C:20]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:21])[CH2:24][CH2:25][CH3:26])[CH3:33])[CH:36]=[C:37]([CH3:38])[CH3:39]>>... | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCC)COC/C=C(\C)CC(C=C(C)C)O[Si](C)(C)C(C)(C)C | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCCO)COC/C=C(\C)CCC=C(C)C | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 787fb5e3ec83f8c7a973e8439218f8d16cc4bbfd1c6f4ab7f2323257a2ee9938 | 8810278526f6a2c0e6c6bc11dce581d57652dfa7eee92b5b7a2e8cacd394ef1e | null | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[CH;D3;+0:2](-[C:3]/[C:4](-[C;D1;H3:5])=[C:6]/[C:7])-[C:8]=[C:9](-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13]-[CH3;D1;+0:14]>>[C:12]-[C:13]-[CH2;D2;+0:14]-[OH;D1;+0:1].[C:7]/[C:6]=[C:4](\[C;D1;H3:5])-[C:3]-[CH2;D2;+0:2]-[C:8]=[C:9](-[C;D1;H3:10])-[C;D1;H3:11] | 54 | [{"value": 54.0, "product": "C\\C(=C/COCC(CCCO)OC(NCCCCCCCC\\C=C/CCCCCCCC)=O)\\CCC=C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring suspension of 140 mg (4.6 mmol) of 80% NaH in 5 mL of tetrahydrofuran is added 1.07 g (4.6 mmol) of (Z)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentene-1,2-diol at 0° C. and the reaction mixture is stirred for 1 hour. Next, 1.0 g (4.6 mmol) of geranyl bromide is added and the reaction is stirred overn... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | null | Other | O1CCCC1 | null | 8 | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCC)COC/C=C(\C)CC(C=C(C)C)O[Si](C)(C)C(C)(C)C>O1CCCC1>CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCCO)COC/C=C(\C)CCC=C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9b608bc0913441a2add7f15519634a7b | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCCO)COC/C=C(\C)CCC=C(C)C>>CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCC(=O)O)COC/C=C(\C)CCC=C(C)C | C(C)(=O)OCC.CCCCCC.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O.C\C(=C/COCC(CCCO)OC(NCCCCCCCC\C=C/CCCCCCCC)=O)\CCC=C(C)C.O>>C\C(=C/COCC(CCC(=O)O)OC(=O)NCCCCCCCC\C=C/CCCCCCCC)\CCC=C(C)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:21])[O:22][CH:23]([CH2:24][CH2:25][CH2:26][OH:28])[CH2:29][O:30][CH2:31]/[CH:32]=[C:33](\[CH3:34])[CH2:35][CH2:36][CH:37]=[C:38]([CH3:39])[CH3:40]>>[CH3:1][CH2:2][CH2... | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCCO)COC/C=C(\C)CCC=C(C)C | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCC(=O)O)COC/C=C(\C)CCC=C(C)C | null | null | CC(=O)C | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[O;D1;H1:4]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[O;D1;H1:4] | 30 | [{"value": 30.0, "product": "C\\C(=C/COCC(CCC(=O)O)OC(=O)NCCCCCCCC\\C=C/CCCCCCCC)\\CCC=C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirring suspension of 140 mg (4.6 mmol) of 80% NaH in 5 mL of tetrahydrofuran is added 1.07 g (4.6 mmol) of (Z)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentene-1,2-diol at 0° C. and the reaction mixture is stirred for 1 hour. Next, 1.0 g (4.6 mmol) of geranyl bromide is added and the reaction is stirred overn... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | null | Other | CC(=O)C | null | 3 | CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCCO)COC/C=C(\C)CCC=C(C)C>CC(=O)C>CCCCCCCC/C=C\CCCCCCCCNC(=O)OC(CCC(=O)O)COC/C=C(\C)CCC=C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-052d6b3cc80f4fa28f5010b0d03ff42b | COC(=O)CCCCCCCC(=O)O>>COC(=O)CCCCCCCCO | C([O-])([O-])=O.[K+].[K+].O.COC(CCCCCCCC(=O)O)=O>>C(=O)(OC)CCCCCCCCO | O=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[OH:13]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13] | COC(=O)CCCCCCCC(=O)O | COC(=O)CCCCCCCCO | null | null | O1CCCC1.C(C)OCC | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | null | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[O;D1;H1:2] | null | [] | null | null | null | null | To a solution of 165 mL (165 mmol) of a 1.0M solution of boranetetrahydrofuran complex in tetrahydrofuran in 200 mL of dry diethyl ether at 0° C. is added dropwise 25.0 g (123 mmol) of azelaic acid monomethyl ester, added at such a rate as to prevent excessive release of gas and exothermicity. The solution is allowed t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | null | Other | O1CCCC1.C(C)OCC | null | null | COC(=O)CCCCCCCC(=O)O>O1CCCC1.C(C)OCC>COC(=O)CCCCCCCCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-272149112272419dac09db7b59175fc6 | COC(=O)CCCCCCCC=O.Clc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>COC(=O)CCCCCCCC=Cc1ccc(Cl)cc1 | C(=O)(OC)CCCCCCCC=O.[Cl-].ClC1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.O.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>>COC(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O | O=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:2... | COC(=O)CCCCCCCC=O.Clc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | COC(=O)CCCCCCCC=Cc1ccc(Cl)cc1 | null | null | O1CCCC1 | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5](-[CH2;D2;+0:6]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:7]>>[C:3]-[C:2]-[CH;D2;+0:1]=[CH;D2;+0:6]-[c:5](:[c:4]):[c:7] | 13 | [{"value": 13.0, "product": "COC(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.8, "product": "COC(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | To a solution of 18.2 g (43 mmol) of 4-chlorobenzyltriphenylphosphonium chloride in 200 mL of dry tetrahydrofuran at -78° C. is added dropwise, 30.7 mL (43 mmol) of a 1.4M solution of potassium hexamethyldisilazide in tetrahydrofuran. This is allowed to stir for 1 hour when 8.0 g (43 mmol) of 8-carbomethoxyoctanal is a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | O1CCCC1 | -78 | 2 | COC(=O)CCCCCCCC=O.Clc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>O1CCCC1>COC(=O)CCCCCCCC=Cc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-40ccf594098e4ab0b5c9d652ad28c8c9 | COC(=O)CCCCCCCC=Cc1ccc(Cl)cc1>>O=C(O)CCCCCCCC=Cc1ccc(Cl)cc1 | COC(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O.O.[OH-].[K+]>>ClC1=CC=C(C=C1)C=CCCCCCCCC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1 | COC(=O)CCCCCCCC=Cc1ccc(Cl)cc1 | O=C(O)CCCCCCCC=Cc1ccc(Cl)cc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 103.7 | [{"value": 100.0, "product": "ClC1=CC=C(C=C1)C=CCCCCCCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.7, "product": "ClC1=CC=C(C=C1)C=CCCCCCCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 1.62 g of 10-(4-chlorophenyl)-dec-9-enoic acid methyl ester in 200 mL of 4:1 methanol:water is added 5.4 g of KOH. The solution is stirred for 2 hours and extracted three times with diethyl ether. The aqueous layer is acidified with concentrated hydrochloric acid, and extracted three times with diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | 2 | COC(=O)CCCCCCCC=Cc1ccc(Cl)cc1>CO>O=C(O)CCCCCCCC=Cc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bdf94d64f6764381bbbb7b18839e7b85 | O=C(O)CCCCCCCC=Cc1ccc(Cl)cc1.O=C1COC(=O)C1>>O=C(CCCCCCCC=Cc1ccc(Cl)cc1)C1=C(O)COC1=O | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.ClC1=CC=C(C=C1)C=CCCCCCCCC(=O)O.Cl>>OC1=C(C(OC1)=O)C(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O | O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.[CH2:19]1[C:20](=[O:21])[CH2:22][O:23][C:24]1=[O:25]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1)[C:19]1=... | O=C(O)CCCCCCCC=Cc1ccc(Cl)cc1.O=C1COC(=O)C1 | O=C(CCCCCCCC=Cc1ccc(Cl)cc1)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Acylation | OtherReaction | 83372693035b8fa3e0bb8f820fc9ffbe16a82c4f9cda2e2eb10c9c9873a82f4e | e14d2b2f4de28ef7423c4b36cf2ab68d975a03db195d5781cd94844876f657bb | O=C(CCCCCCCC=Cc1ccccc1)C1=CCOC1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#8:7]-[C:6]-1=[O;D1;H0:5] | 58.3 | [{"value": 58.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "OC1=C(C(OC1)=O)C(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 189 mg (1.89 mmol) of tetronic acid in 15 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 8 mg (66 μmol) of 4-dimethylaminopyridine at 0° C. Next, 427 mg (2.22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 690 mg (2.20 mmol) of 10-(4-chloroph... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Ester.Enol | C1CCOC1 | C1=CCOC1 | c1ccccc1.C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 8 | O=C(O)CCCCCCCC=Cc1ccc(Cl)cc1.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C>O=C(CCCCCCCC=Cc1ccc(Cl)cc1)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-44d7775ce6aa4fefbef4fb0336de5ad9 | O=C(CCCCCCCC=Cc1ccc(Cl)cc1)C1=C(O)COC1=O>>O=C(CCCCCCCCCc1ccc(Cl)cc1)C1=C(O)COC1=O | OC1=C(C(OC1)=O)C(CCCCCCCC=CC1=CC=C(C=C1)Cl)=O.[H][H]>>OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC=C(C=C1)Cl)=O | [O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1)[C:19]1=[C:20]([OH:21])[CH2:22][O:23][C:24]1=[O:25]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1)[C:19]1=[C... | O=C(CCCCCCCC=Cc1ccc(Cl)cc1)C1=C(O)COC1=O | O=C(CCCCCCCCCc1ccc(Cl)cc1)C1=C(O)COC1=O | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C(CCCCCCCCCc1ccccc1)C1=CCOC1=O | [C:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 66.2 | [{"value": 66.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 1.58 g (4.35 mmol) of 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl]-2(5H)-furanone in 100 mL of ethyl acetate is added 250 mg of 5% palladium on carbon and subjected to atmospheric hydrogenation using a balloon to deliver the hydrogen. After 1.5 hours, the reaction is worked up by filtering through... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1=CCOC1 | null | [Pd].C(C)(=O)OCC | null | 1.5 | O=C(CCCCCCCC=Cc1ccc(Cl)cc1)C1=C(O)COC1=O>[Pd].C(C)(=O)OCC>O=C(CCCCCCCCCc1ccc(Cl)cc1)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f914f1b01af4f37afa76a477fc47d49 | Clc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1Cl.O=C(CCCCCCCCCc1ccc(Cl)cc1)C1=C(O)COC1=O>>O=C(CCCCCCCCCc1ccc(Cl)c(Cl)c1)C1=C(O)COC1=O | OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC=C(C=C1)Cl)=O.[Br-].ClC=1C=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1Cl>>OC1=C(C(OC1)=O)C(CCCCCCCCCC1=CC(=C(C=C1)Cl)Cl)=O | c1ccc([P+](Cc2[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]2)(c2ccccc2)c2ccccc2)cc1.Clc1cc[c:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:20]2=[C:21]([OH:22])[CH2:23][O:24][C:25]2=[O:26])cc1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][c:12... | Clc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1Cl.O=C(CCCCCCCCCc1ccc(Cl)cc1)C1=C(O)COC1=O | O=C(CCCCCCCCCc1ccc(Cl)c(Cl)c1)C1=C(O)COC1=O | null | null | null | Miscellaneous | Chlorination | a75780ad41689d17a554385d20850b63fb9ab3d1ffe8b04e695b227216b2c71f | f004e58a958e83ed69c0f163c54d2c11d46ff03ec9dbfbb5a519e7e4cb2f94a4 | O=C(CCCCCCCCCc1ccccc1)C1=CCOC1=O | Cl-c1:c:c:[c;H0;D3;+0:1](-[C:2]-[C:3]):c:c:1.[Cl;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[cH;D2;+0:8]:c(-C-[P+](-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):[cH;D2;+0:9]:1>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:8]:[c:7]:[c:6]:[c:5](-[Cl;D1;H0:4]):[cH;D2;+0:9]:1 | null | [] | null | null | null | null | Using the procedure of Example 41 for the synthesis of 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodecyl]-2(5H)-furanone above, but using 3,4-dichlorobenzyltriphenylphosphonium bromide in place of 4-chlorobenzyltriphenylphosphonium chloride, there is obtained the title compound.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.C1=CCOC1 | HCl | null | null | null | Clc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1Cl.O=C(CCCCCCCCCc1ccc(Cl)cc1)C1=C(O)COC1=O>>O=C(CCCCCCCCCc1ccc(Cl)c(Cl)c1)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-07070efa6bb7493ba824bd6a67d62928 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1>>CCCCC/C=C\C/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O | Cl.C1C(=O)CSC1=O.Cl.CN(CCCN=C=NCC)C.C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O>>OC1=C(C(SC1)=O)C(CCCCCCC\C=C/C\C=C/CCCCC)=O | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[CH2:20]1[C:21](=[O:22])[CH2:23][S:24][C:25]1=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16... | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C.C(C)N(CC)CC | Acylation | OtherReaction | 6714b009b6527a4771b2978d8bcacda7334e2d808587085f563010f99c0b230d | dafec1f680dddeecef40928e47e7ad5a6064cf6b7de607c7a2702053621c6a49 | O=C1C=CCS1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#16:7]-[C:6]-1=[O;D1;H0:5] | 30 | [{"value": 30.0, "product": "OC1=C(C(SC1)=O)C(CCCCCCC\\C=C/C\\C=C/CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.9, "product": "OC1=C(C(SC1)=O)C(CCCCCCC\\C=C/C\\C=C/CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 1.71 g (14.75 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 2.22 ML (17.2 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-dimethylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4.96 g (17.7 mmol) of lino... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Enol | C1CCSC1 | C1=CCSC1 | C1=CCSC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C.C(C)N(CC)CC | null | 8 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C.C(C)N(CC)CC>CCCCC/C=C\C/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-56f204da68f24bf2af050b76d59dd02c | CCCCCCCC/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1>>CCCCCCCC/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O | C1C(=O)CSC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCCCCC\C=C/CCCCCCCC)(=O)O.Cl>>OC1=C(C(SC1)=O)C(CCCCCCC\C=C/CCCCCCCC)=O | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[CH2:20]1[C:21](=[O:22])[CH2:23][S:24][C:25]1=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][... | CCCCCCCC/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1 | CCCCCCCC/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O | null | null | CN(C=O)C | Acylation | OtherReaction | 6714b009b6527a4771b2978d8bcacda7334e2d808587085f563010f99c0b230d | dafec1f680dddeecef40928e47e7ad5a6064cf6b7de607c7a2702053621c6a49 | O=C1C=CCS1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#16:7]-[C:6]-1=[O;D1;H0:5] | 33 | [{"value": 33.0, "product": "OC1=C(C(SC1)=O)C(CCCCCCC\\C=C/CCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.0, "product": "OC1=C(C(SC1)=O)C(CCCCCCC\\C=C/CCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 1.71 g (14.75 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 2.22 mL (17.2 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-diemthylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.7 mmol) of oleic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Enol | C1CCSC1 | C1=CCSC1 | C1=CCSC1 | HO- | CN(C=O)C | null | 8 | CCCCCCCC/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1>CN(C=O)C>CCCCCCCC/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-243a5dc120ec4f6cbfc4a4e41f55729b | CCCC/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1>>CCCC/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O | C1C(=O)CSC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCCCCC\C=C/CCCC)(=O)O.Cl>>OC1=C(C(SC1)=O)C(CCCCCCC\C=C/CCCC)=O | O[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][CH3:1])=[O:15].[CH2:16]1[C:17](=[O:18])[CH2:19][S:20][C:21]1=[O:22]>>[CH3:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[C:16]1=[C:17]([OH:18])[CH2:19][S:20][C:21... | CCCC/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1 | CCCC/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Acylation | OtherReaction | 6714b009b6527a4771b2978d8bcacda7334e2d808587085f563010f99c0b230d | dafec1f680dddeecef40928e47e7ad5a6064cf6b7de607c7a2702053621c6a49 | O=C1C=CCS1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#16:7]-[C:6]-1=[O;D1;H0:5] | 33 | [{"value": 33.0, "product": "OC1=C(C(SC1)=O)C(CCCCCCC\\C=C/CCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "OC1=C(C(SC1)=O)C(CCCCCCC\\C=C/CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 855 mg (7.37 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 902 μL (6.47 mmol) of triethylamine and 240 mg (1.96 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.68 g (8.76 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (8.84 mmol) of myristo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Enol | C1CCSC1 | C1=CCSC1 | C1=CCSC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 8 | CCCC/C=C\CCCCCCCC(=O)O.O=C1CSC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C>CCCC/C=C\CCCCCCCC(=O)C1=C(O)CSC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3d699815cf194d7584f2790f886973cf | CC(CCC(=O)O)Oc1ccccc1Cl.O=C1CSC(=O)C1>>O=C(CCCCOc1ccc(Cl)cc1)C1=C(O)CSC1=O | Cl.Cl.CN(CCCN=C=NCC)C.ClC1=C(OC(CCC(=O)O)C)C=CC=C1.C1C(=O)CSC1=O.C(C)N(CC)CC.CN(C=O)C>>OC1=C(C(SC1)=O)C(CCCCOC1=CC=C(C=C1)Cl)=O | O[C:2](=[O:1])[CH2:3][CH2:4][CH:6]([CH3:5])[O:7][c:8]1[cH:9][cH:10][cH:14][cH:13][c:11]1[Cl:12].[CH2:15]1[C:16](=[O:17])[CH2:18][S:19][C:20]1=[O:21]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[C:15]1=[C:16]([OH:17])[CH2:18][S:19][C:20]1=[O:21] | CC(CCC(=O)O)Oc1ccccc1Cl.O=C1CSC(=O)C1 | O=C(CCCCOc1ccc(Cl)cc1)C1=C(O)CSC1=O | null | CN(C1=CC=NC=C1)C | null | Acylation | OtherReaction | 3044937a91be0bb7b19e906d2f75aa342d1f4032144b3914ef0cd1d41471540e | 6ddad5b9f5a975b3619d12fc5d10625926a9c7ef6a44819d9d229ad6cecefa02 | O=C(CCCCOc1ccccc1)C1=CCSC1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[CH2;D2;+0:4]-[CH;D3;+0:5](-[CH3;D1;+0:6])-[#8:7]-[c;H0;D3;+0:8]1:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c;H0;D3;+0:13]:1-[Cl;D1;H0:14].[O;D1;H0:15]=[C:16]1-[#16:17]-[C:18]-[C;H0;D3;+0:19](=[O;H0;D1;+0:20])-[CH2;D2;+0:21]-1>>[Cl;D1;H0:14]-[c;H0;D3;+0:13]1:[c:12]:[cH;D2;+0:11]:[c;... | 24 | [{"value": 24.0, "product": "OC1=C(C(SC1)=O)C(CCCCOC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 224 mg (1.89 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 77 mg (631 μmol) of 4-dimethylaminopyridine at 0° C. Next, 440 mg (2.29 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 530 mg (2.32 mmol) of 5-[4-(ch... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Ketone.Ether.Carbo-thioester | Aromatic halide.Ketone.Ether.Enol.Carbo-thioester | c1ccccc1.C1CCSC1 | c1ccccc1.C1=CCSC1 | c1ccccc1.C1=CCSC1 | HO- | CN(C1=CC=NC=C1)C | null | 8 | CC(CCC(=O)O)Oc1ccccc1Cl.O=C1CSC(=O)C1>CN(C1=CC=NC=C1)C>O=C(CCCCOc1ccc(Cl)cc1)C1=C(O)CSC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-000ac27e0d20476fa9a1cccb03a4816e | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O.O=C1CSC(=O)C1>>CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)C1=C(O)CSC1=O | C1C(=O)CSC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCC\C=C/C\C=C/C\C=C/CCCCC)(=O)O.Cl>>OC1=C(C(SC1)=O)C(CCCC\C=C/C\C=C/C\C=C/CCCCC)=O | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]\[CH2:11]/[CH:10]=[CH:9]\[CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[CH2:20]1[C:21](=[O:22])[CH2:23][S:24][C:25]1=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:... | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O.O=C1CSC(=O)C1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)C1=C(O)CSC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Acylation | OtherReaction | 6714b009b6527a4771b2978d8bcacda7334e2d808587085f563010f99c0b230d | dafec1f680dddeecef40928e47e7ad5a6064cf6b7de607c7a2702053621c6a49 | O=C1C=CCS1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#16:7]-[C:6]-1=[O;D1;H0:5] | 79.1 | [{"value": 79.0, "product": "OC1=C(C(SC1)=O)C(CCCC\\C=C/C\\C=C/C\\C=C/CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "OC1=C(C(SC1)=O)C(CCCC\\C=C/C\\C=C/C\\C=C/CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 695 mg (6.04 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 902 μL (6.47 mmol) of triethylamine and 240 mg (1.97 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.37 g (7.13 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (7.19 mmol) of γ-linol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Enol | C1CCSC1 | C1=CCSC1 | C1=CCSC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 8 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O.O=C1CSC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C>CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)C1=C(O)CSC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4e49cc0e8ce64dcebb1e7faeb65b7100 | CCCCCCCCCCC/C=C\CCCCC(=O)O.O=C1CSC(=O)C1>>CCCCCCCCCCC/C=C\CCCCC(=O)C1=C(O)CSC1=O | C1C(=O)CSC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCC\C=C/CCCCCCCCCCC)(=O)O.Cl>>OC1=C(C(SC1)=O)C(CCCC\C=C/CCCCCCCCCCC)=O | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]\[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[CH2:20]1[C:21](=[O:22])[CH2:23][S:24][C:25]1=[O:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][... | CCCCCCCCCCC/C=C\CCCCC(=O)O.O=C1CSC(=O)C1 | CCCCCCCCCCC/C=C\CCCCC(=O)C1=C(O)CSC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Acylation | OtherReaction | 6714b009b6527a4771b2978d8bcacda7334e2d808587085f563010f99c0b230d | dafec1f680dddeecef40928e47e7ad5a6064cf6b7de607c7a2702053621c6a49 | O=C1C=CCS1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#16:7]-[C:6]-1=[O;D1;H0:5] | 21.4 | [{"value": 21.0, "product": "OC1=C(C(SC1)=O)C(CCCC\\C=C/CCCCCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.4, "product": "OC1=C(C(SC1)=O)C(CCCC\\C=C/CCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 1.71 g (14.7 mmol) of thiotetronic acid in 20 mL of dimethylformamide is added 2.22 mL (15.9 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-dimethylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.7 mmol) of petros... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Enol | C1CCSC1 | C1=CCSC1 | C1=CCSC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 8 | CCCCCCCCCCC/C=C\CCCCC(=O)O.O=C1CSC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C>CCCCCCCCCCC/C=C\CCCCC(=O)C1=C(O)CSC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-167d0a27c3f44fe8a981a20de9d90482 | CCCCCCCC/C=C\CCCCCCCC(=O)OC>>CCCCCCCC[C@H]1C[C@H]1CCCCCCCC(=O)O | [OH-].[K+].C(CCCCCCC\C=C/CCCCCCCC)(=O)OC.ICI.Cl>>C(CCCCCCC)[C@@H]1[C@@H](C1)CCCCCCCC(=O)O | C[O:21][C:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[CH2:10][C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:20])[OH:21] | CCCCCCCC/C=C\CCCCCCCC(=O)OC | CCCCCCCC[C@H]1C[C@H]1CCCCCCCC(=O)O | null | [Cu].[Zn] | O1CCCC1.CO.O.CCOCC | C-C Coupling | OtherReaction | 1e52603cbed5de06b32494efa880e761a95cf830454ebe8a237236c6e4c2b426 | 0e8bfaadacac8bbbe418c7b3917d31c9c44abd3f8b993574f44a6d35c2089c0b | C1CC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[C:5]-[C:6]/[CH;D2;+0:7]=[CH;D2;+0:8]\[C:9]-[C:10]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:5]-[C:6]-[C@@H;D3;+0:7]1-[C:11]-[C@@H;D3;+0:8]-1-[C:9]-[C:10] | null | [] | null | null | 4 | HOUR | To 2.2 g of zinc-copper couple in 30 mL of dry ether is added 5.7 mL (16.9 mmol) of methyl oleate and 5.4 mL (70.7 mmol) of diiodomethane. The reaction mixture is refluxed overnight, cooled to room temperature, poured into 1.0N HCl, and extracted three times with ether. The organic layers are combined, washed with brin... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | C1CC1 | C1CC1 | null | [Cu].[Zn].O1CCCC1.CO.O.CCOCC | null | 4 | CCCCCCCC/C=C\CCCCCCCC(=O)OC>[Cu].[Zn].O1CCCC1.CO.O.CCOCC>CCCCCCCC[C@H]1C[C@H]1CCCCCCCC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6ebe688ebcaa44038748c3ce2deef2cf | CCCCCCC/C=C\O>>CCCCC[C@H]1C[C@H]1CC(=O)O | C(=C/CCCCCCC)/O.C([O-])(O)=O.[Na+].[Br-].[Na+]>>C(CCCC)[C@@H]1[C@@H](C1)CC(=O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:8]/[CH:9]=[CH:10]\[OH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]1[CH2:9][C:10](=[O:11])[OH:12] | CCCCCCC/C=C\O | CCCCC[C@H]1C[C@H]1CC(=O)O | null | null | ClCCl.[O-]Cl.[Na+].O | Oxidation | OtherReaction | f4f5ffefd530c022cb95f299a174d3c2106f3fe3242221fbb89af6000677fa92 | a96b3355e2d06c36358ca144e0625b00da9ba545d201aa15e4b5c88ba8941785 | C1CC1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]/[CH;D2;+0:5]=[CH;D2;+0:6]\[O;D1;H1:7]>>[C:1]-[C:2]-[C@H;D3;+0:3]1-[C:8]-[C@H;D3;+0:4]-1-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:9])-[O;D1;H1:7] | null | [] | null | null | null | null | Cis-nonen-1-ol (10.0 g) is subjected to the cyclopropanation conditions as described in the preparation of Example 52. The resulting residue is taken up in 100 mL of dichloromethane at 0° C., followed by the addition of 800 mg of sodium bromide in 2 mL of water and 150 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free r... | 10.6084/m9.figshare.5104873.v1 | null | Enol | Carboxylic acid | null | C1CC1 | C1CC1 | Other | ClCCl.[O-]Cl.[Na+].O | null | null | CCCCCCC/C=C\O>ClCCl.[O-]Cl.[Na+].O>CCCCC[C@H]1C[C@H]1CC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-90778638d2d846cb914d436e47461d28 | CCCCCCC/C=C\O>>CCCCC[C@H]1C[C@H]1CC(=O)O | C(=C/CCCCCCC)/O.C([O-])(O)=O.[Na+].[Br-].[Na+]>>C(CCCC)[C@@H]1[C@@H](C1)CC(=O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:8]/[CH:9]=[CH:10]\[OH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[CH2:7][C@H:8]1[CH2:9][C:10](=[O:11])[OH:12] | CCCCCCC/C=C\O | CCCCC[C@H]1C[C@H]1CC(=O)O | null | null | ClCCl.[O-]Cl.[Na+].O | Oxidation | OtherReaction | f4f5ffefd530c022cb95f299a174d3c2106f3fe3242221fbb89af6000677fa92 | a96b3355e2d06c36358ca144e0625b00da9ba545d201aa15e4b5c88ba8941785 | C1CC1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]/[CH;D2;+0:5]=[CH;D2;+0:6]\[O;D1;H1:7]>>[C:1]-[C:2]-[C@H;D3;+0:3]1-[C:8]-[C@H;D3;+0:4]-1-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:9])-[O;D1;H1:7] | null | [] | null | null | null | null | Cis-nonen-1-ol (10.0 g) is subjected to the cyclopropanation conditions described in the preparation of Example 52. The resulting residue is taken up in 100 mL of dichloromethane at 0° C., followed by the addition of 800 mg of sodium bromide in 2 mL of water and 150 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radi... | 10.6084/m9.figshare.5104873.v1 | null | Enol | Carboxylic acid | null | C1CC1 | C1CC1 | Other | ClCCl.[O-]Cl.[Na+].O | null | null | CCCCCCC/C=C\O>ClCCl.[O-]Cl.[Na+].O>CCCCC[C@H]1C[C@H]1CC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b671135f8fab4cebb2baed92c5498047 | CCCCCCCCCCCCCCCC(=O)O.O=C1COC(=O)C1>>CCCCCCCCCCCCCCCC(=O)C1=C(O)COC1=O | C1C(=O)COC1=O.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C.C(CCCCCCCCCCCCCCC)(=O)O.Cl>>OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCC)=O | O[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].[CH2:18]1[C:19](=[O:20])[CH2:21][O:22][C:23]1=[O:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:18]1=[C:1... | CCCCCCCCCCCCCCCC(=O)O.O=C1COC(=O)C1 | CCCCCCCCCCCCCCCC(=O)C1=C(O)COC1=O | null | CN(C1=CC=NC=C1)C | CN(C=O)C | C-C Coupling | OtherReaction | 15f3304ec355e6fae5bb90bae6b36a89baad3bf259dbcee9cf11733ab1cc8fc4 | 1eaefd43aa20304b18998f5790ec5413e598d7869b87589e6ad9c00e178e5f4e | O=C1C=CCO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:8]-[#8:7]-[C:6]-1=[O;D1;H0:5] | 91 | [{"value": 91.0, "product": "OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "OC1=C(C(OC1)=O)C(CCCCCCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 650 mg (6.5 mmol) of tetronic acid in 20 mL of dimethylformamide is added 1.0 mL (7.17 mmol) of triethylamine and 230 mg (1.88 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.50 g (7.81 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.0 g (7.81 mmol) of palmitic aci... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ketone.Ester.Enol | C1CCOC1 | C1=CCOC1 | C1=CCOC1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 8 | CCCCCCCCCCCCCCCC(=O)O.O=C1COC(=O)C1>CN(C1=CC=NC=C1)C.CN(C=O)C>CCCCCCCCCCCCCCCC(=O)C1=C(O)COC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e26bcea9d9b94655bfa1a6ada380e790 | Cl.O=C1c2ccccc2C(=O)N1CCBr>>O=C1c2ccccc2C(=O)N1CCCl | C(C)(C)O.Cl.CNOC.C([O-])(O)=O.[Na+].BrCCN1C(C=2C(C1=O)=CC=CC2)=O>>ClCCN1C(C=2C(C1=O)=CC=CC2)=O | [ClH:14].Br[CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][Cl:14] | Cl.O=C1c2ccccc2C(=O)N1CCBr | O=C1c2ccccc2C(=O)N1CCCl | null | null | C(C)N(CC)CC | Miscellaneous | OtherReaction | 44416d7280a6eed8367e02dc126eb30a4d00133331bdb39af1bfd9ebc219496d | 6582de26f5a81cea01b9d3d75c7e3ef916f109d129591531b0e3c46e4dd6dd55 | O=C1NC(=O)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[ClH;D0;+0:8]>>[Cl;H0;D1;+0:8]-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7] | 65.4 | [{"value": 65.4, "product": "ClCCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a suspension of 50 ml of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.90 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. The resulting mixture became homogeneous after 5 minutes. Thereto was added 2.45 g (10.0 mmol) of N-(bromoethyl)phthalimide and the mixture was refluxed for 29 hour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccc2c(c1)C[NH]C2 | HBr | C(C)N(CC)CC | null | 0.083333 | Cl.O=C1c2ccccc2C(=O)N1CCBr>C(C)N(CC)CC>O=C1c2ccccc2C(=O)N1CCCl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a7a6cc20410049fab1aec4b794941182 | Cl.O=C1c2ccccc2C(=O)N1CCCBr>>O=C1c2ccccc2C(=O)N1CCCCl | C(C)(C)O.Cl.CNOC.C([O-])(O)=O.[Na+].BrCCCN1C(C=2C(C1=O)=CC=CC2)=O>>ClCCCN1C(C=2C(C1=O)=CC=CC2)=O | [ClH:15].Br[CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][Cl:15] | Cl.O=C1c2ccccc2C(=O)N1CCCBr | O=C1c2ccccc2C(=O)N1CCCCl | null | null | C(C)N(CC)CC | Miscellaneous | OtherReaction | 44416d7280a6eed8367e02dc126eb30a4d00133331bdb39af1bfd9ebc219496d | 6582de26f5a81cea01b9d3d75c7e3ef916f109d129591531b0e3c46e4dd6dd55 | O=C1NC(=O)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[ClH;D0;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[Cl;H0;D1;+0:4] | 46.1 | [{"value": 46.1, "product": "ClCCCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a suspension of 50 mol of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.97 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. After 5 minutes, there was added 2.68 g (10.0 mmol) of N-(3-bromopropyl)phthalimide and the mixture was refluxed for 33 hours. This was cooled to room temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccc2c(c1)C[NH]C2 | HBr | C(C)N(CC)CC | null | 0.083333 | Cl.O=C1c2ccccc2C(=O)N1CCCBr>C(C)N(CC)CC>O=C1c2ccccc2C(=O)N1CCCCl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-478d26280dd042778a8b8e437feb89ca | CON(C)CCCNc1ncnc2nc[nH]c12>>CON(C)C(C)CNc1ncnc2nc[nH]c12 | O.NN.ClC1=C2NC=NC2=NC=N1.C(C)N(C(C)C)C(C)C.CON(C)CCCNC1=C2NC=NC2=NC=N1>>CON(C)C(CNC1=C2NC=NC2=NC=N1)C | [CH3:1][O:2][N:3]([CH3:4])[CH2:6][CH2:5][CH2:7][NH:8][c:9]1[n:10][cH:11][n:12][c:13]2[n:14][cH:15][nH:16][c:17]12>>[CH3:1][O:2][N:3]([CH3:4])[CH:5]([CH3:6])[CH2:7][NH:8][c:9]1[n:10][cH:11][n:12][c:13]2[n:14][cH:15][nH:16][c:17]12 | CON(C)CCCNc1ncnc2nc[nH]c12 | CON(C)C(C)CNc1ncnc2nc[nH]c12 | null | null | null | Miscellaneous | OtherReaction | 22169e4bba42f6de2dce29b7a2eab579bcc8704590e37efe17439a11bc863d77 | 369439ea5e3b5385f82622b2f847d97774609daa0a245c4972a5b6731db0af42 | c1ncc2[nH]cnc2n1 | [#7:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[#8:7]-[C;D1;H3:8]>>[#7:1]-[C:2]-[CH;D3;+0:3](-[CH3;D1;+0:4])-[N;H0;D3;+0:5](-[C;D1;H3:6])-[#8:7]-[C;D1;H3:8] | 36 | [{"value": 36.0, "product": "CON(C)C(CNC1=C2NC=NC2=NC=N1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In 15 ml of ethanol was dissolved 1.21 g (4.88 mmol) of the imide obtained in the above (1) and there was added 0.293 g (5.86 mmol) of hydrazine hydrate, followed by refluxing for 6 hours and cooling in an ice bath. The resulting solid was filtered off and the filtrate was concentrated to 2 ml by evaporator with a wate... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Tertiary amine | null | null | c1ncc2nc[nH]c2n1 | null | null | null | null | CON(C)CCCNc1ncnc2nc[nH]c12>>CON(C)C(C)CNc1ncnc2nc[nH]c12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c4193453fc9d45de86f939592e52320a | Cl.O=C1c2ccccc2C(=O)N1CCCCBr>>O=C1c2ccccc2C(=O)N1CCCCCl | C(C)(C)O.Cl.CNOC.C([O-])(O)=O.[Na+].BrCCCCN1C(C=2C(C1=O)=CC=CC2)=O>>ClCCCCN1C(C=2C(C1=O)=CC=CC2)=O | [ClH:16].Br[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16] | Cl.O=C1c2ccccc2C(=O)N1CCCCBr | O=C1c2ccccc2C(=O)N1CCCCCl | null | null | C(C)N(CC)CC | Miscellaneous | OtherReaction | 44416d7280a6eed8367e02dc126eb30a4d00133331bdb39af1bfd9ebc219496d | 6582de26f5a81cea01b9d3d75c7e3ef916f109d129591531b0e3c46e4dd6dd55 | O=C1NC(=O)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[ClH;D0;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[Cl;H0;D1;+0:4] | 42.7 | [{"value": 42.7, "product": "ClCCCCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a suspension of 50 ml of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.97 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. The resulting mixture became homogeneous after 5 minutes. There were added 2.00 g (7.09 mmol) of N-(4-bromobutyl)phthalimide and the mixture was refluxed for 58 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccc2c(c1)C[NH]C2 | HBr | C(C)N(CC)CC | null | 0.083333 | Cl.O=C1c2ccccc2C(=O)N1CCCCBr>C(C)N(CC)CC>O=C1c2ccccc2C(=O)N1CCCCCl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0a96ee7305764e7999d6459c776096d9 | C=CCCCCCCCCCCCCCC.Oc1ccccc1>>CCCCCCCCCCCCCCCCc1ccc(O)cc1 | C1(=CC=CC=C1)O.C=CCCCCCCCCCCCCCC>>C(CCCCCCCCCCCCCCC)C1=CC=C(C=C1)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16].[cH:17]1[cH:18][cH:19][c:20]([OH:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20]... | C=CCCCCCCCCCCCCCC.Oc1ccccc1 | CCCCCCCCCCCCCCCCc1ccc(O)cc1 | null | null | null | C-C Coupling | Friedel-Crafts alkylation | b5ecb16d263633fede39aa315b72fcd11a4271c4c269240c71ce2aeab0441f31 | 77f5ef22613a838acebd80af913dfe5f962fd974e0c65f81cd0800ac736db6a9 | c1ccccc1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | 110 | CELSIUS | 2 | HOUR | Phenol (376 g, 4 mol), hexadecene (α-olefin) (449 g, 2 mol) and ion exchange resin (trade-mark: Dia-ion RCP-145HD) (34 g) were charged in a reactor and stirred at 110° C. for 2 hours. The ion exchange resin was filtered off and the excessive phenol and hexadecene were distilled off under reduced pressure. After distill... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | null | 110 | 2 | C=CCCCCCCCCCCCCCC.Oc1ccccc1>>CCCCCCCCCCCCCCCCc1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9cf256dca8e143efbbadb3597f087187 | CC(=O)Oc1ccc(C(=O)Cl)cc1.CCCCCCCCc1ccc(O)c(N)c1>>CCCCCCCCc1ccc(O)c(NC(=O)c2ccc(OC(C)=O)cc2)c1 | C(C)(=O)OC1=CC=C(C(=O)Cl)C=C1.NC1=C(C=CC(=C1)CCCCCCCC)O.O1CCOCC1>>C(C)(=O)OC1=CC=C(C(=O)NC2=C(C=CC(=C2)CCCCCCCC)O)C=C1 | Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([O:22][C:23]([CH3:24])=[O:25])[cH:26][cH:27]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([OH:13])[c:14]([NH2:15])[cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([OH:13])[c:14]([NH:15][C:16](... | CC(=O)Oc1ccc(C(=O)Cl)cc1.CCCCCCCCc1ccc(O)c(N)c1 | CCCCCCCCc1ccc(O)c(NC(=O)c2ccc(OC(C)=O)cc2)c1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 70.8 | [{"value": 70.8, "product": "C(C)(=O)OC1=CC=C(C(=O)NC2=C(C=CC(=C2)CCCCCCCC)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 100 ml round-bottom flask, the resultant 4-acetoxybenzoic chloride, 3.10 g (15.1 m mole) of 2-amino-4-octylphenol and 40 ml of dioxane were placed and heated to keep inner temperature 85 to 88.5° C. To the mixture, 5.5 ml of pyridine was added dropwise under stirring, followed by heating and stirring for 20 minute... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | CC(=O)Oc1ccc(C(=O)Cl)cc1.CCCCCCCCc1ccc(O)c(N)c1>N1=CC=CC=C1>CCCCCCCCc1ccc(O)c(NC(=O)c2ccc(OC(C)=O)cc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-28f375b39e234f8da9850f5e356e8b45 | CCCCCCC(=O)O.CCCCCCCCc1ccc2oc(-c3ccc(O)cc3)nc2c1>>CCCCCCCCc1ccc2oc(-c3ccc(OC(=O)CCCCCC)cc3)nc2c1 | OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)CCCCCCCC.C(CCCCCC)(=O)O>>C(CCCCCC)(=O)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)CCCCCCCC | O[C:20](=[O:21])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[o:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([OH:19])[cH:28][cH:29]3)[n:30][c:31]2[cH:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2... | CCCCCCC(=O)O.CCCCCCCCc1ccc2oc(-c3ccc(O)cc3)nc2c1 | CCCCCCCCc1ccc2oc(-c3ccc(OC(=O)CCCCCC)cc3)nc2c1 | null | null | ClCCl | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | c1ccc(-c2nc3ccccc3o2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 60.9 | [{"value": 60.9, "product": "C(CCCCCC)(=O)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)CCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.9, "product": "C(CCCCCC)(=O)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)CCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 30 ml round-bottom flask, 0.50 g (1.55 m mole) of 2-(4-hydroxyphenyl)-5-octylbenzooxazole, 0.22 g (1.69 m mole) of heptanoic acid and 10 ml of dichloromethane were placed, followed by adding 0.32 g (1.55 m mole) of N,N-dicyclohexylcarbodiimide and 0.04 g of 4-pyrrodinopyridine in order at room temperature under st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccc2ocnc2c1.c1ccccc1 | HO- | ClCCl | null | null | CCCCCCC(=O)O.CCCCCCCCc1ccc2oc(-c3ccc(O)cc3)nc2c1>ClCCl>CCCCCCCCc1ccc2oc(-c3ccc(OC(=O)CCCCCC)cc3)nc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-38e673fe1a454cec8a6dc24ef59e2c1c | CC(=O)c1ccc(O)c([N+](=O)[O-])c1>>CC(=O)c1ccc(O)c(N)c1 | [N+](=O)([O-])C1=C(C=CC(=C1)C(C)=O)O.[OH-].[Na+].S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>NC1=C(C=CC(=C1)C(C)=O)O | O=[N+:10]([O-])[c:9]1[c:7]([OH:8])[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:11]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([NH2:10])[cH:11]1 | CC(=O)c1ccc(O)c([N+](=O)[O-])c1 | CC(=O)c1ccc(O)c(N)c1 | null | null | 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] | 39.1 | [{"value": 39.1, "product": "NC1=C(C=CC(=C1)C(C)=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.1, "product": "NC1=C(C=CC(=C1)C(C)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | In a 300 ml three-neck flask, 5.00 g (27.6 m mole) of 2-nitro-4-acetylphenol and 75 ml of 2N-sodium hydroxide solution were placed. To the mixture solution, a solution, which 25.00 g of sodium hydrosulfite was dissolved in 75 ml to water, was added dropwise in 10 minutes. Then the mixture solution was stirred for 20 mi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | O | null | 0.333333 | CC(=O)c1ccc(O)c([N+](=O)[O-])c1>O>CC(=O)c1ccc(O)c(N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-07d0a3d4d786447dba463b8c0927c013 | CCCCCCCCCCOc1ccc(-c2nc3cc(C(C)=O)ccc3o2)cc1>>CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)O)ccc3o2)cc1 | C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(C)=O.Br[O-].[Na+].Br[O-].[Na+].Cl(=O)(=O)O.Br(=O)(=O)O.[OH-].[Na+]>>C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(=O)O | C[C:21]([c:20]1[cH:19][c:18]2[n:17][c:16](-[c:15]3[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:29][cH:28]3)[o:27][c:26]2[cH:25][cH:24]1)=[O:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[n:1... | CCCCCCCCCCOc1ccc(-c2nc3cc(C(C)=O)ccc3o2)cc1 | CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)O)ccc3o2)cc1 | null | null | O.O1CCOCC1 | Oxidation | Oxidation of ketone to carboxylic acid | 4dcefe9f257f90cd8a0ae39598d4f86ef2c4bc85e982c4f410a0cc8e41935547 | 781042da5dd3f0df3f3d742e6083e42895047983989d3fba759328a89315b3ce | c1ccc(-c2nc3ccccc3o2)cc1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;D1;H1:8]):[c:4] | 75 | [{"value": 75.0, "product": "C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | -6.25 | CELSIUS | null | null | Example Compound I-51 was synthesized through the following steps: ##STR88## 1.61 g (40.3 m mole) of sodium hydroxide was dissolved in 10.7 ml of water, followed by cooling at -7.5--5° C. on ice-common salt bath. To the solution, 0.66 ml (25.6 m mole) of bromic acid was added dropwise under stirring, followed by coolin... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Carboxylic acid | null | null | c1ccccc1.c1ccc2ocnc2c1 | null | O.O1CCOCC1 | -6.25 | null | CCCCCCCCCCOc1ccc(-c2nc3cc(C(C)=O)ccc3o2)cc1>O.O1CCOCC1>CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)O)ccc3o2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2a52736b43a444e09a503ac093ca58e8 | CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)O)ccc3o2)cc1.CCCCCCCCO>>CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)OCCCCCCCC)ccc3o2)cc1 | C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(=O)O.C(CCCCCCC)O.N1(CCCC1)C1=CC=NC=C1>>C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(=O)OCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[n:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[OH:23])[cH:32][cH:33][c:34]3[o:35]2)[cH:36][cH:37]1.O[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH... | CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)O)ccc3o2)cc1.CCCCCCCCO | CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)OCCCCCCCC)ccc3o2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccc(-c2nc3ccccc3o2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5](-[OH;D1;+0:6])-[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5](=[O;D1;H0:4])-[c:7] | 49.3 | [{"value": 49.3, "product": "C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(=O)OCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.3, "product": "C(CCCCCCCCC)OC1=CC=C(C=C1)C=1OC2=C(N1)C=C(C=C2)C(=O)OCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 30 ml round-bottom flask, 0.30 g (0.76 m mole) of 2-(4-decyloxyphenyl)-5-carboxybenzooxazole, 0.11 g (0,84 m mole) of octanol and 8 ml of dichloromethane were placed. To the mixture solution 0.16 g (0.78 m mole) of N,N'-dicyclohexycarbodiimide and 0.04 g of 4-pyrrolidinopyridine were added in order under stirring ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | ClCCl | null | null | CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)O)ccc3o2)cc1.CCCCCCCCO>ClCCl>CCCCCCCCCCOc1ccc(-c2nc3cc(C(=O)OCCCCCCCC)ccc3o2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1dfcf1ca247542b98a807a6c7678748b | CCCCCCCCCCOc1ccc2cc(C(=O)Cl)ccc2c1.CCCCc1ccc(O)c(N)c1>>CCCCCCCCCCOc1ccc2cc(C(=O)Nc3cc(CCCC)ccc3O)ccc2c1 | N1=CC=CC=C1.NC1=C(C=CC(=C1)CCCC)O.C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)Cl.O1CCOCC1>>C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)NC1=C(C=CC(=C1)CCCC)O | Cl[C:18]([c:17]1[cH:16][c:15]2[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:35][c:34]2[cH:33][cH:32]1)=[O:19].[NH2:20][c:21]1[cH:22][c:23]([CH2:24][CH2:25][CH2:26][CH3:27])[cH:28][cH:29][c:30]1[OH:31]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:... | CCCCCCCCCCOc1ccc2cc(C(=O)Cl)ccc2c1.CCCCc1ccc(O)c(N)c1 | CCCCCCCCCCOc1ccc2cc(C(=O)Nc3cc(CCCC)ccc3O)ccc2c1 | null | null | O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1ccc2ccccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 86.8 | [{"value": 86.5, "product": "C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)NC1=C(C=CC(=C1)CCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)NC1=C(C=CC(=C1)CCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | In a 50 ml three-neck flask, 0.40 g (2.42 m mole) of 2-amino-4-butylphenol, 0.85 g (2.74 m mole) of 6-decyloxy-2-naphthoic acid chloride and 10 ml of dioxane were placed. To the mixture, 0.81 ml of pyridine was added dropwise under stirring at ca. 75° C. of mixture temperature. After the reaction, the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1.c1ccccc1 | HCl | O | 75 | null | CCCCCCCCCCOc1ccc2cc(C(=O)Cl)ccc2c1.CCCCc1ccc(O)c(N)c1>O>CCCCCCCCCCOc1ccc2cc(C(=O)Nc3cc(CCCC)ccc3O)ccc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f954faeda5054c7c942ac3ce9dae5608 | CCCCc1ccc(O)c(NC(=O)c2ccc3cc(OC(C)=O)ccc3c2)c1>>CCCCc1ccc2oc(-c3ccc4cc(O)ccc4c3)nc2c1 | C1=CC=C(C(=C1)Cl)Cl.C(C)(=O)OC=1C=C2C=CC(=CC2=CC1)C(=O)NC1=C(C=CC(=C1)CCCC)O.C1=CC=C(C(=C1)Cl)Cl.Cl(=O)(=O)O>>OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC | CC(=O)[O:17][c:16]1[cH:15][c:14]2[cH:13][cH:12][c:11]([C:10](=O)[NH:22][c:23]3[c:8]([OH:9])[cH:7][cH:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[cH:24]3)[cH:21][c:20]2[cH:19][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]2[o:9][c:10](-[c:11]3[cH:12][cH:13][c:14]4[cH:15][c:16]([OH:17])[cH:18][cH:19][c:20]4[cH:21... | CCCCc1ccc(O)c(NC(=O)c2ccc3cc(OC(C)=O)ccc3c2)c1 | CCCCc1ccc2oc(-c3ccc4cc(O)ccc4c3)nc2c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | fc74dd05c5b65c401f921808a9da40083d558e8753a9ad252f469a984b1618f5 | 2e532d254482469e8109acb67ae5f92196131fd8d26738177347e7db5dd6b9ec | c1ccc2cc(-c3nc4ccccc4o3)ccc2c1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[C;H0;D3;+0:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[c:14]:[c:13]:[c;H0;D3;+0:12](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:11]):[o;H0;D2;+0:10]:1):[c:15]:[c:16... | 48 | [{"value": 42.4, "product": "OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.0, "product": "OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 201.5 | CELSIUS | 30 | MINUTE | 5.40 g (14.3 m mole) of 2-(6-acetoxy-2-naphthoylamino)-4-butylphenol, 0.43 g of p-toluenesulfuric acid monohydrate and 40 ml of O-dichlorobenzene were placed in a 100 ml round-bottom flask, followed by heating and stirring for 30 minutes at 200-203° C. After the reaction, O-dichlorobenzene was distilled off under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Aromatic alcohol | Aromatic alcohol | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1ccc2ccccc2c1 | HO- | O | 201.5 | 0.5 | CCCCc1ccc(O)c(NC(=O)c2ccc3cc(OC(C)=O)ccc3c2)c1>O>CCCCc1ccc2oc(-c3ccc4cc(O)ccc4c3)nc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b2461ebc65244f8f8d1cf4f61ec82c12 | CCCCCCCCI.CCCCc1ccc2oc(-c3ccc4cc(O)ccc4c3)nc2c1>>CCCCCCCCOc1ccc2cc(-c3nc4cc(CCCC)ccc4o3)ccc2c1 | OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC.C(CCCCCCC)I.[OH-].[K+].C(CCC)O>>C(CCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC | I[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[n:17][c:18]4[cH:19][c:20]([CH2:21][CH2:22][CH2:23][CH3:24])[cH:25][cH:26][c:27]4[o:28]3)[cH:29][cH:30][c:31]2[cH:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:1... | CCCCCCCCI.CCCCc1ccc2oc(-c3ccc4cc(O)ccc4c3)nc2c1 | CCCCCCCCOc1ccc2cc(-c3nc4cc(CCCC)ccc4o3)ccc2c1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2cc(-c3nc4ccccc4o3)ccc2c1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 56.6 | [{"value": 56.6, "product": "C(CCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.6, "product": "C(CCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C=1OC2=C(N1)C=C(C=C2)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 30ml round-bottom flask, 0.47 g (1.48 m mole) of 2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole, 0.43 g (1.79 m mole) of octyl iodide, 0.12 g (1.82 m mole) of potassium hydroxide and 5 ml of butanol were placed, followed by refluxing for 310 minutes. The reaction mixture was poured into water, extracted from ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1.c1ccc2ocnc2c1 | HI | O | null | null | CCCCCCCCI.CCCCc1ccc2oc(-c3ccc4cc(O)ccc4c3)nc2c1>O>CCCCCCCCOc1ccc2cc(-c3nc4cc(CCCC)ccc4o3)ccc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e39f5bba0a6d4f2e88f4a74a2a9aada9 | CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1.C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)COP(=O)([O-])O>>C=C(C)C(=O)OCCO | C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N.OS(=O)(=O)O.C[C@@H](C=O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H]([C@@H]1CCNC(=N)N1)NC(=O)N[C@@H](CC(C)C)C(=O)O.CC(C=1C=CC(=C(C1)F)C=2C=CC=CC2)C(=O)O.C[C@@H]1C[C... | Fc1c[c:1]([CH:2]([CH3:3])[C:4](=[O:5])[OH:6])ccc1-c1ccccc1.C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)[C:8]([CH2:7]OP(=O)([O-])O)=[O:9]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][OH:9] | CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1.C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)COP(=O)([O-])O | C=C(C)C(=O)OCCO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0a9f29ae9ec41c848fd6e803e19d09f0ce53ec0bf54fb2f813e5aeb0e788e8b9 | ecd841edb60dd1824d97ec144cbb3d184e3b0c6adec4f35520cf5b526dcc2758 | null | C-[C@H]1-C-[C@@H]2-[C@H]3-C-C-C4=C-C(=O)-C=C-[C@]-4(-C)-[C@@]-3(-F)-[C@@H](-O)-C-[C@]-2(-C)-[C@@]-1(-O)-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-O-P(-O)(=O)-[O-].F-c1:c:[c;H0;D3;+0:4](-[CH;D3;+0:5](-[C;D1;H3:6])-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]):c:c:c:1-c1:c:c:c:c:c:1>>[C;D1;H3:6]-[C;H0;D3;+0:5](=[CH2;D1;+0:4])-[C... | null | [] | null | null | null | null | A mixture was prepared by combining aprotinin 1 g.; elastatinal 0.1 g.; flurbiprofen 0.1 g.; dexamethasone sodium phosphate 0.1 g.; neomycin sulfate; and physiological saline up to 100 g. A contact lens form the crosslinked polymer of 2-hydroxyethyl methacrylate (38 percent by weight of equilibrium water) was swelled i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary halide.Carboxylic acid.Ketone.Ketone.Secondary alcohol.Tertiary alcohol | Ester.Primary alcohol.Vinyl | c1ccccc1.c1ccccc1.C1=C[C@H]2C(=CC1)CC[C@H]1[C@@H]3CCC[C@H]3CC[C@@H]12 | null | null | HF | null | null | null | CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1.C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)COP(=O)([O-])O>>C=C(C)C(=O)OCCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-66975d29552e40698e5e404f59eebdbb | CC(=O)CC(C)C.CC(C)(c1ccc(OCC2CO2)cc1)c1ccc(OCC2CO2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOCC.Oc1cccc(O)c1 | CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4.C(C(C)C)C(=O)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C1(O)=CC(O)=CC=C1.CCOCC | CC(C)C[C:4](=[O:3])[CH3:5].CC(C)(c1cc[c:7]([O:6]CC2CO2)[cH:13]c1)[c:8]1cc[c:11]([O:12]CC2CO2)[cH:10][cH:9]1.c1ccc(P(c2ccccc2)c2ccc[cH:2][cH:1]2)cc1>>[CH3:1][CH2:2][O:3][CH2:4][CH3:5].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([OH:12])[cH:13]1 | CC(=O)CC(C)C.CC(C)(c1ccc(OCC2CO2)cc1)c1ccc(OCC2CO2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CCOCC.Oc1cccc(O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 59fe90d2d01355facc003189ea0c57988237bf08b213d7eeca62932c7ca52861 | 7a05ff73164eef3abe6dc2257a934cf80bc7c22b689bb600f31df9db4289c44c | c1ccccc1 | C-C(-C)(-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:5]-C-C2-C-O-2):c:c:1)-c1:c:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[O;H0;D2;+0:8]-C-C2-C-O-2):c:c:1.C-C(-C)-C-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11].[cH;D2;+0:12]1:[cH;D2;+0:13]:c:c:c:c:1-P(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:10]-[CH2;D2;+0:9]-[O;H0;D2;... | null | [] | 117 | CELSIUS | null | null | A resorcinol-formaldehyde resin/diglycidyl ether of bisphenol A addition product was prepared in a lab reactor by a procedure comparable to that employed in Example 1. The reactor was charged with about 31.1 g. of a commercial resorcinol-formaldehyde resin, Penacolite B-19-S, (INDSPEC Chemical Corporation, Pittsburgh, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Ether | Ether.Aromatic alcohol.Aromatic alcohol | c1ccccc1.C1CO1.c1ccccc1.C1CO1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 117 | null | CC(=O)CC(C)C.CC(C)(c1ccc(OCC2CO2)cc1)c1ccc(OCC2CO2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOCC.Oc1cccc(O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e551bf9aea5c4c649c5667d952fb6c3a | Oc1cccc(O)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOCC | CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4.C1(O)=CC(O)=CC=C1.CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4.C1(O)=CC(O)=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C1(O)=CC(O)=CC=C1.CCOCC | Oc1ccc[c:4]([OH:3])[cH:5]1.c1ccc(P(c2ccccc2)c2ccc[cH:2][cH:1]2)cc1>>[CH3:1][CH2:2][O:3][CH2:4][CH3:5] | Oc1cccc(O)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CCOCC | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | f6e5cb66acaf6576e7f585343cb99fd612ed2073524494984c9bb4cbfd9f24d4 | 1b01c2e952e9b9a243172fd343c7ddee55ba0e54cb91a463cb02594d1b905e77 | null | O-c1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[OH;D1;+0:3]):c:c:c:1.[cH;D2;+0:4]1:[cH;D2;+0:5]:c:c:c:c:1-P(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[CH3;D1;+0:4]-[CH2;D2;+0:5]-[O;H0;D2;+0:3]-[CH2;D2;+0:2]-[CH3;D1;+0:1] | null | [] | 112 | CELSIUS | null | null | A resorcinol/diglycidyl ether of bisphenol A addition product was prepared in a 3-liter reactor equipped with an agitator, thermometer and reflux condenser. The reactor was charged with about 330.3 g. resorcinol, 1500 ml. toluene and 3.0 g. triphenylphosphine. The stirred charge was heated to reflux at about 112° C. an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | C1(=CC=CC=C1)C | 112 | null | Oc1cccc(O)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>CCOCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-902981f1e39d465089d3ea04f2f44bcd | CCCCCCCC/C=C\CCCCCCCCCCCC(=O)O>>CCCCCCCC/C=C\CCCCCCCC(=O)O | C(CCCCCCCCCCCCCCCCC)(=O)OCCCC.CCCCCCCCCCCCCCCCCC[N+](C)(C)C.[Cl-].CCCCCCCCCCCCCCCCCCN(CCOCCO)CCOCCO.C(CCCCCCCCCCC)(=O)OCCCC.C(CCCCCCCCCCC\C=C/CCCCCCCC)(=O)O>>C(CCCCCCC\C=C/CCCCCCCC)(=O)O | C(CC[CH2:16][CH2:17][C:18](=[O:19])[OH:20])C[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[OH:20] | CCCCCCCC/C=C\CCCCCCCCCCCC(=O)O | CCCCCCCC/C=C\CCCCCCCC(=O)O | null | CCCCCCCCCCCC[N+](C)(C)C.[Cl-] | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [C:1]-[C:2]-[CH2;D2;+0:3]-C-C-C-C-[CH2;D2;+0:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | null | [] | null | null | null | null | Examples of lubricating agents which can be used in the present invention are commercially available under the trade names of NAA-102, NAA-415, NAA-312, NAA-160, NAA-180, NAA-174, NAA-175, NAA-222, NAA-34, NAA-35, NAA-171, NAA-122, NAA-142, NAA-160, NAA-173K, Castor oil-cured fatty acid, NAA-42, NAA-44, Cation SA, Cati... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CCCCCCCCCCCC[N+](C)(C)C.[Cl-] | null | null | CCCCCCCC/C=C\CCCCCCCCCCCC(=O)O>CCCCCCCCCCCC[N+](C)(C)C.[Cl-]>CCCCCCCC/C=C\CCCCCCCC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6fca121f54ad4dbeb09f154726606a7f | CC(=O)Oc1cc(C(=O)O)cc(OC(C)=O)c1OC(C)=O.O=C(Cl)C(=O)Cl>>CC(=O)Oc1cc(C(=O)Cl)cc(OC(C)=O)c1OC(C)=O | C(C)(=O)OC=1C=C(C(=O)O)C=C(C1OC(C)=O)OC(C)=O.C(C(=O)Cl)(=O)Cl.CN(C=O)C>>C(C)(=O)OC=1C=C(C(=O)Cl)C=C(C1OC(C)=O)OC(C)=O | O[C:8]([c:7]1[cH:6][c:5]([O:4][C:2]([CH3:1])=[O:3])[c:17]([O:18][C:19]([CH3:20])=[O:21])[c:12]([O:13][C:14]([CH3:15])=[O:16])[cH:11]1)=[O:9].O=C(Cl)C(=O)[Cl:10]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]([C:8](=[O:9])[Cl:10])[cH:11][c:12]([O:13][C:14]([CH3:15])=[O:16])[c:17]1[O:18][C:19]([CH3:20])=[O:21] | CC(=O)Oc1cc(C(=O)O)cc(OC(C)=O)c1OC(C)=O.O=C(Cl)C(=O)Cl | CC(=O)Oc1cc(C(=O)Cl)cc(OC(C)=O)c1OC(C)=O | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccccc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | 3,4,5-Triacetoxybenzoic acid (296.23 g, 1 mol) was slurried in a 2 L flask in CH2Cl2 (1.0 L), and oxalyl chloride (113 mL, 1.3 mol) as added, followed by slow, dropwise addition of N,N-dimethylformamide (1.5 mL). After 2 hours at RT, gas evolution had ceased, and 3,4,5-triacetoxybenzoyl chloride was isolated by evapora... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 2 | CC(=O)Oc1cc(C(=O)O)cc(OC(C)=O)c1OC(C)=O.O=C(Cl)C(=O)Cl>C(Cl)Cl>CC(=O)Oc1cc(C(=O)Cl)cc(OC(C)=O)c1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a06527d7605c46b0b8ec403e13acd486 | C=C(C)C(=O)OCCN.CC(=O)Oc1cc(C(=O)Cl)cc(OC(C)=O)c1OC(C)=O>>C=C(C)C(=O)OCCNC(=O)c1cc(OC(C)=O)c(OC(C)=O)c(OC(C)=O)c1 | Cl.Cl.C(C(=C)C)(=O)OCCN.C(C)(=O)OC=1C=C(C(=O)Cl)C=C(C1OC(C)=O)OC(C)=O.C(C)N(CC)CC>>C(C(=C)C)(=O)OCCNC(C1=CC(=C(C(=C1)OC(C)=O)OC(C)=O)OC(C)=O)=O | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][NH2:9].Cl[C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][C:16]([CH3:17])=[O:18])[c:19]([O:20][C:21]([CH3:22])=[O:23])[c:24]([O:25][C:26]([CH3:27])=[O:28])[cH:29]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][C:1... | C=C(C)C(=O)OCCN.CC(=O)Oc1cc(C(=O)Cl)cc(OC(C)=O)c1OC(C)=O | C=C(C)C(=O)OCCNC(=O)c1cc(OC(C)=O)c(OC(C)=O)c(OC(C)=O)c1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | 3,4,5-Triacetoxybenzoyl chloride (0.050 mol) was dissolved in 100 mL CH2Cl2 at 0° C. To this was added 2-aminoethyl methacrylate hydrochloride (8.28 g, 0.050 mol), followed by dropwise addition of triethylamine (14.63 mL, 0.105 mol). After 30 min, 100 mL 1N HCl was added with vigorous stirring. The organic layer was is... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | C=C(C)C(=O)OCCN.CC(=O)Oc1cc(C(=O)Cl)cc(OC(C)=O)c1OC(C)=O>C(Cl)Cl>C=C(C)C(=O)OCCNC(=O)c1cc(OC(C)=O)c(OC(C)=O)c(OC(C)=O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c12e9f988a1d48c99466fdb4537eb263 | COC(=O)c1ccc(-c2cc3ccccc3c(O)c2C)cc1OC>>COC(=O)c1ccc(-c2cc3ccccc3c(O)c2C)cc1O | CC1=C(C2=CC=CC=C2C=C1C1=CC(=C(C=C1)C(=O)OC)OC)O.B(Cl)(Cl)Cl>>CC1=C(C2=CC=CC=C2C=C1C1=CC(=C(C=C1)C(=O)OC)O)O | C[O:23][c:22]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]([OH:18])[c:19]2[CH3:20])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]([OH:18])[c:19]2[CH3:20])[cH:21][c:22]1[OH:23] | COC(=O)c1ccc(-c2cc3ccccc3c(O)c2C)cc1OC | COC(=O)c1ccc(-c2cc3ccccc3c(O)c2C)cc1O | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccc3ccccc3c2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 71.7 | [{"value": 71.7, "product": "CC1=C(C2=CC=CC=C2C=C1C1=CC(=C(C=C1)C(=O)OC)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 8 | HOUR | To a cooled (-78° C.) suspension of 7.0 g of 2-methyl-3-(4'-methoxycarbonyl-3'-methoxyphenyl)-1-naphthol in 100 mL of methylene chloride was added, dropwise over 10 minutes, 26 mL of 1 M boron trichloride in methylene chloride. The resulting mixture was stirred overnight at 25° C. and then quenched with 25 mL of methan... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | 25 | 8 | COC(=O)c1ccc(-c2cc3ccccc3c(O)c2C)cc1OC>C(Cl)Cl>COC(=O)c1ccc(-c2cc3ccccc3c(O)c2C)cc1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d126743b54247e4b00946be9eb577bd | COC(=O)c1ccc(I)cc1OC>>COC(=O)c1ccc(-c2ccc(C(=O)OC)c(OC)c2)cc1OC | IC1=CC(=C(C(=O)OC)C=C1)OC.C(Cl)(Cl)Cl>>COC=1C=C(C=CC1C(=O)OC)C1=CC(=C(C=C1)C(=O)OC)OC | I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:22]([O:23][CH3:24])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20]2)[cH:21][c:22]1[O:23][CH3:24] | COC(=O)c1ccc(I)cc1OC | COC(=O)c1ccc(-c2ccc(C(=O)OC)c(OC)c2)cc1OC | null | [Cu] | CN(C=O)C | Aromatic Heterocycle Formation | Ullmann condensation | 4eae742ef48646e6302e88514288333213f00927a85699086e718a4dbfd59416 | b02e223c1da4cc07342be5079603c39a95d01b5c6bff482c05584416dbcdcba1 | c1ccc(-c2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:6]:[c:7](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:8] | 64.8 | [{"value": 64.8, "product": "COC=1C=C(C=CC1C(=O)OC)C1=CC(=C(C=C1)C(=O)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mechanically stirred suspension of 90 g of copper powder in 450 mL of dimethylformamide was added 90 g of methyl 4-iodo-2-methoxybenzoate (which was prepared as in Example 1). The resulting mixture was heated at reflux for 6 days and then cooled to room temperature and diluted into 1500 mL of chloroform. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ester.Ether | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | I- | [Cu].CN(C=O)C | null | null | COC(=O)c1ccc(I)cc1OC>[Cu].CN(C=O)C>COC(=O)c1ccc(-c2ccc(C(=O)OC)c(OC)c2)cc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-352027f5ace04caca5d1f5c9a25194cf | Oc1c(Br)ccc2ccccc12>>COc1c(Br)ccc2ccccc12 | C1(=CC=CC2=CC=CC=C12)O.BrC1=C(C2=CC=CC=C2C=C1)O.BrNC(C)(C)C.BrC1=C(C2=CC=CC=C2C=C1)O.C([O-])([O-])=O.[K+].[K+]>>BrC1=C(C2=CC=CC=C2C=C1)OC | [OH:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | Oc1c(Br)ccc2ccccc12 | COc1c(Br)ccc2ccccc12 | null | null | CC(=O)C | Miscellaneous | OtherReaction | 5b3aadc337038ce4d56616083181fcdb7df90626e7a012c21497c4b51b07950e | b3459c109bd254a21bc857ecee1ac83a8b4bf01bca8b217fb3b07e012c0f1c4b | c1ccc2ccccc2c1 | [OH;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 25 | CELSIUS | 8 | HOUR | 1-naphthol was converted into 2-bromo-1-naphthol by reaction with a slurry of N-bromo-t-butylamine at -78° C. according to the procedure described in Pearson, Wysong, Breder, J. Org. Chem. 32, 2358 (1967). To a solution of 1 mole (crude) of the bromonaphthol in 750 mL of acetone was added 175 g of potassium carbonate. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1 | Other | CC(=O)C | 25 | 8 | Oc1c(Br)ccc2ccccc12>CC(=O)C>COc1c(Br)ccc2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-45091bce8d8d4124bcddaf8e105dd9d8 | COc1cc(N)cc2ccccc12.[I-]>>COc1cc(I)cc2ccccc12 | [I-].[K+].II.N(=O)[O-].[Na+].NC=1C=C(C2=CC=CC=C2C1)OC.S(O)(O)(=O)=O.C1=CC=CC2=CC=CC=C12>>IC=1C=C(C2=CC=CC=C2C1)OC | N[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:13]2[c:8]([cH:7]1)[cH:9][cH:10][cH:11][cH:12]2.[I-:6]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([I:6])[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | COc1cc(N)cc2ccccc12.[I-] | COc1cc(I)cc2ccccc12 | null | null | C(Cl)Cl.O | Functional Group Interconversion | OtherReaction | 76f8d811a111586e25da9919d89f8b392932b9c6bdd2c2cd3df2f5f34505ef64 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccc2ccccc2c1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[I-;H0;D0:6]>>[I;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 18.3 | [{"value": 18.3, "product": "IC=1C=C(C2=CC=CC=C2C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 50 g of 3-amino-1-methoxynaphthalene was added to 750 mL of 6 N sulfuric acid. The mixture was heated to dissolve the naphthalene and the resulting solution was cooled to 0° C. To the resulting slurry of amine hydrosulfate salt at 0° C. was added a solution of 20 g of sodium nitrite in 30 mL of water. The resulting mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | Other | C(Cl)Cl.O | 0 | 1 | COc1cc(N)cc2ccccc12.[I-]>C(Cl)Cl.O>COc1cc(I)cc2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c2d3f9dc48864913be85c1333e2753ce | COC1=C/C(=C2/C=C(OC)c3ccccc3C2=O)C(=O)c2ccccc21.COc1ccc(O)c2ccccc12>>COc1cc(-c2cc(OC)c3ccccc3c2O)c(O)c2ccccc12 | COC1=CC=C(C2=CC=CC=C12)O.COC1=C/C(=C\2/C=C(C3=CC=CC=C3C2=O)OC)/C(=O)C4=CC=CC=C41>>COC1=CC(=C(C2=CC=CC=C12)O)C=1C=C(C2=CC=CC=C2C1O)OC | COC1=C/C(=[C:6]2/[CH:7]=[C:8]([O:9][CH3:10])[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[C:17]2=[O:18])C(=O)c2ccccc21.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:19]([OH:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([O:9][CH3:10])[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[O... | COC1=C/C(=C2/C=C(OC)c3ccccc3C2=O)C(=O)c2ccccc21.COc1ccc(O)c2ccccc12 | COc1cc(-c2cc(OC)c3ccccc3c2O)c(O)c2ccccc12 | null | [Ag]=O | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 27c64f889579bc41d61589608b5ec45cc97c8b94e83dde1d3261dccb8dbd45fa | e1898297c63ffafe69fcdb3c84aaf71be5242604ede701ede5f5d43a17b9ab97 | c1ccc2cc(-c3ccc4ccccc4c3)ccc2c1 | C-O-C1=C/C(=[C;H0;D3;+0:1]2/[CH;D2;+0:2]=[C;H0;D3;+0:3](-[#8:4]-[C;D1;H3:5])-[c:6](:[c:7]):[c:8](:[c:9])-[C;H0;D3;+0:10]-2=[O;H0;D1;+0:11])-C(=O)-c2:c:c:c:c:c:2-1.[O;D1;H1:12]-[c:13](:[c:14]):[cH;D2;+0:15]:[c:16]:[c:17]>>[C;D1;H3:5]-[#8:4]-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:... | null | [] | null | null | null | null | Under an atmosphere of nitrogen, a mixture of 5.0 g of 4-methoxy-1-naphthol and 50 mL chloroform was mechanically stirred with 10.0 g silver oxide until the conversion to Russig's Blue was complete. The unreacted silver oxide was filtered and washed with chloroform. The filtrate and chloroform washings were combined an... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Ether | Ether.Aromatic alcohol | C1=Cc2ccccc2CC1.C1=Cc2ccccc2CC1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2ccccc2c1 | HO- | [Ag]=O.C(Cl)(Cl)Cl | null | null | COC1=C/C(=C2/C=C(OC)c3ccccc3C2=O)C(=O)c2ccccc21.COc1ccc(O)c2ccccc12>[Ag]=O.C(Cl)(Cl)Cl>COc1cc(-c2cc(OC)c3ccccc3c2O)c(O)c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-be1ccb7d1f2e45ccb333bd9c40dea672 | BrCc1ccccc1.Nc1cccc(Br)c1>>Brc1cccc(N(Cc2ccccc2)Cc2ccccc2)c1 | BrC=1C=C(N)C=CC1.[O-2].[Mg+2].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N(C1=CC(=CC=C1)Br)CC1=CC=CC=C1 | Br[CH2:15][c:16]1[cH:8][cH:20][cH:19][cH:18][cH:17]1.[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:22]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1 | BrCc1ccccc1.Nc1cccc(Br)c1 | Brc1cccc(N(Cc2ccccc2)Cc2ccccc2)c1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 002dd433875ae6181b9e8871539c18262046d9a1577ea5f1b281a5cd9bdc8797 | b876acfcfd55a49f65dd18e6b419e3ae94e13e667fff68e28052076a5e501128 | c1ccc(CN(Cc2ccccc2)c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:12]:[c:13](-[CH2;D2;+0:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[c:14]:1)-[c:9](:[c:10]):[c:11]):[c:15] | 63.4 | [{"value": 63.4, "product": "C(C1=CC=CC=C1)N(C1=CC(=CC=C1)Br)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 47 | HOUR | A mixture of 16 g of 3-bromoaniline, 15 g magnesium oxide and 31.8 g benzylbromide in 100 mL dry dimethylformamide was stirred for 47 hours at room temperature, under nitrogen. The precipitated magnesium salts were filtered. The filtrate was diluted with water and extracted with ether. The ether extracts were combined,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Tertiary amine | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Br- | CN(C=O)C | null | 47 | BrCc1ccccc1.Nc1cccc(Br)c1>CN(C=O)C>Brc1cccc(N(Cc2ccccc2)Cc2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-68533ad2f643465da0032cda5ac4e078 | COc1cccc(-c2cc(OC)ccc2Br)c1.O=C=O>>COc1cccc(-c2cc(OC)ccc2C(=O)O)c1 | Cl.BrC1=CC=C(C=C1C1=CC(=CC=C1)OC)OC.C(C)(C)(C)[Li].C(=O)=O>>C(=O)(O)C1=C(C=C(C=C1)OC)C1=CC=CC(=C1)OC | Br[c:15]1[c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19]2)[cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1.[C:16](=[O:17])=[O:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14][c:15]2[C:16](=[O:17])[OH:18])[cH:19]1 | COc1cccc(-c2cc(OC)ccc2Br)c1.O=C=O | COc1cccc(-c2cc(OC)ccc2C(=O)O)c1 | null | null | CN(C=O)C.CCOCC.O | Acylation | OtherReaction | 07ac4a201d363784a28677e85b547e572f4793f5010c94050885192cae13600e | d0d963f3850574b1f0fda744314036458b2dd627cb0c4e2f893b9c52a88ad449 | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[O;H0;D1;+0:9]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[OH;D1;+0:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]):[c:6] | null | [] | -60 | CELSIUS | null | null | 12.1 g of 6-bromo-3,3'-dimethoxy-biphenyl was dissolved in 100 mL of dry dimethylformamide and the resulting solution was cooled to -60° C. under nitrogen. 55 mL of 1.7 M t-butyllithium in hexanes was added over a 20-minute period. The resulting solution was transferred to another flask containing a mixture of 275 mL o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | CN(C=O)C.CCOCC.O | -60 | null | COc1cccc(-c2cc(OC)ccc2Br)c1.O=C=O>CN(C=O)C.CCOCC.O>COc1cccc(-c2cc(OC)ccc2C(=O)O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55908127f3db4593a4b9cdbbe3effaaf | COc1cccc(-c2cc(OC)ccc2C(=O)O)c1>>COc1ccc2c(c1)-c1cc(OC)ccc1C2=O | C(=O)(O)C1=C(C=C(C=C1)OC)C1=CC=CC(=C1)OC>>COC=1C=CC=2C(C3=CC=C(C=C3C2C1)OC)=O | O[C:17]([c:16]1[c:9](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]1)=[O:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)-[c:9]1[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]1[C:17]2=[O:18] | COc1cccc(-c2cc(OC)ccc2C(=O)O)c1 | COc1ccc2c(c1)-c1cc(OC)ccc1C2=O | null | null | CS(=O)(=O)O | Functional Group Interconversion | OtherReaction | 7ef164e95534b750b8f447337d5960d1ddb5d629daec09f6c5afef2d8b94fe7a | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1c2ccccc2-c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[c:3](:[c:4]):[c:5]-[c:6](:[c:7]):[c;H0;D3;+0:8]-1:[c:9]:[c:10] | 96 | [{"value": 96.0, "product": "COC=1C=CC=2C(C3=CC=C(C=C3C2C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 7.5 g of 2-carboxy-5,5'-dimethoxybiphenyl was dissolved in 75 mL of methanesulfonic acid to obtain a dark brown solution. The solution was stirred at room temperature for one hour, heated at 40°-50° C. for 5 hours and then cooled to room temperature. The reaction mixture was then poured onto crushed ice to form a yello... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | HO- | CS(=O)(=O)O | null | 1 | COc1cccc(-c2cc(OC)ccc2C(=O)O)c1>CS(=O)(=O)O>COc1ccc2c(c1)-c1cc(OC)ccc1C2=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e639ae9580b5409ba9d211431f724411 | O=C(O)CN(CCN(CC(=O)O)CC(=O)O)CCN(CC(=O)O)CC(=O)O>>O=C(O)CN(CCN1CC(=O)OC(=O)C1)CCN1CC(=O)OC(=O)C1 | C(CN(CC(=O)O)CC(=O)O)N(CCN(CC(=O)O)CC(=O)O)CC(=O)O>>C1C(=O)OC(=O)CN1CCN(CCN2CC(=O)OC(=O)C2)CC(=O)O | O=[C:23]([OH:24])[CH2:25][N:18]([CH2:17][CH2:16][N:5]([CH2:4][C:2](=[O:1])[OH:3])[CH2:6][CH2:7][N:8]([CH2:9][C:10](O)=[O:11])[CH2:15][C:13]([OH:12])=[O:14])[CH2:19][C:20](=[O:21])[OH:22]>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]([CH2:6][CH2:7][N:8]1[CH2:9][C:10](=[O:11])[O:12][C:13](=[O:14])[CH2:15]1)[CH2:16][CH2:17][N:18]1[CH2... | O=C(O)CN(CCN(CC(=O)O)CC(=O)O)CCN(CC(=O)O)CC(=O)O | O=C(O)CN(CCN1CC(=O)OC(=O)C1)CCN1CC(=O)OC(=O)C1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 349075840a3e55794f76a0c9b5f86aea0f12f7d8910f76667a3087ed551a4d31 | e83a95bc3ef3bbc28a0f9ce60ccfbd3725429b901b391dbfdf0df35bff2f3261 | O=C1CN(CCNCCN2CC(=O)OC(=O)C2)CC(=O)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8].O=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[C:11]-[#7:12]-[C:13]-[C:14](=[O;D1;H0:15])-[OH;D1;+0:16]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[#7:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-1.[O;D1;H0:15]=[C:14]1-[C:13]-[#7:12]-[C:11]-[C;H0;D3;+0:9](=[O... | null | [] | null | null | 1 | MINUTE | A 0.1 mg/ml solution of DTPA anhydride in dry chloroform was prepared and an aliquot containing the desired quantity of DTPA was added to a reaction vessel. The chloroform was removed by evaporation with nitrogen gas at room temperature. A pH 7.0 solution of antibody (approximately 0.5 mg) in 0.05M bicarbonate buffer w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid | Anhydride.Anhydride | null | C1COCC[NH]1.C1COCC[NH]1 | C1COCC[NH]1.C1COCC[NH]1 | HO- | C(Cl)(Cl)Cl | null | 0.016667 | O=C(O)CN(CCN(CC(=O)O)CC(=O)O)CCN(CC(=O)O)CC(=O)O>C(Cl)(Cl)Cl>O=C(O)CN(CCN1CC(=O)OC(=O)C1)CCN1CC(=O)OC(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-445013eb9d6b4372b91d441d2c130c81 | C=Cc1ccccc1C=C>>C=Cc1ccccc1C=C | C=CC1=CC=CC=C1.C(=C)C1=C(C=CC=C1)C=C.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(=C)C1=C(C=CC=C1)C=C.C=CC1=CC=CC=C1 | [CH2:9]=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[CH:17]=[CH2:18]>>[CH2:9]=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[CH:17]=[CH2:18] | C=Cc1ccccc1C=C | C=Cc1ccccc1C=C | null | null | C1(=CC=CC=C1)C.CCCCCCCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 30 | MINUTE | It is stirred at room temperature for 30 minutes and then is introduced the monomer system prepared separately consisting of g 100 of styrene, g 67.5 of divinylbenzene (50%) in toluene (225 ml) and n-octane (75 ml) containing 3 g of benzoyl peroxide. The polymerization is carried out by stirring (350 rpm) for 10 hours ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C1(=CC=CC=C1)C.CCCCCCCC | null | 0.5 | C=Cc1ccccc1C=C>C1(=CC=CC=C1)C.CCCCCCCC>C=Cc1ccccc1C=C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-38a46896cfd64460abeefed1d758aed6 | CO.OCc1ccccc1>>O=C1OCc2ccccc21 | C(C1=CC=CC=C1)O.CO>>C1(=O)OCC2=CC=CC=C12 | [OH:1][CH3:2].[OH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]1[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21 | CO.OCc1ccccc1 | O=C1OCc2ccccc21 | null | null | null | Acylation | OtherReaction | 9c781c87019ca9dede634b6715ed379de45cc6d56d21647480a8071c0c797a3b | 3a43f9a173fafaac93ce4acffd0e49b127157cffd4a7a649a0004a5981bc5a14 | O=C1OCc2ccccc21 | [CH3;D1;+0:1]-[OH;D1;+0:2].[OH;D1;+0:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[O;H0;D1;+0:2]=[C;H0;D3;+0:1]1-[O;H0;D2;+0:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7]-1:[c:8]:[c:9] | null | [] | null | null | null | null | The procedure described in method F is repeated, except that the methanol is replaced by 50 ml of benzyl alcohol, affording a phthalide compound of the formula ##STR19## melting point 183°-184° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Methanol | Ester | c1ccccc1 | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | null | null | null | null | CO.OCc1ccccc1>>O=C1OCc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d52f08e66fb34664977e68b9daab7854 | N#Cc1ccc(-c2ccc(C3CCC(=O)CC3)cc2)cc1>>N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 | C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)C1CCC(CC1)=O.C(C)OCC.Cl.[BH4-].[Na+]>>C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]3[CH2:12][CH2:13][C:14](=[O:15])[CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][cH:21]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C@H:11]3[CH2:12][CH2:13][C@H:14]([OH:15])[CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][cH:21]1 | N#Cc1ccc(-c2ccc(C3CCC(=O)CC3)cc2)cc1 | N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 2851cada23ce4ae5bca04d1ef48c1473fe285273d9a82803d040df273fff8e79 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2ccc(C3CCCCC3)cc2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6]>>[C:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6] | 34.7 | [{"value": 34.7, "product": "C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A suspension of 10 g of 4-(4'-cyano-4-biphenylyl)cyclohexanone, 30 ml of diethyl ether and 270 ml of methanol was treated portionwise at 0° C. with 1.8 g of sodium borohydride. After 3 hours the reaction mixture was made acid (pH 1-2) with 25% hydrochloric acid. The reaction mixture was extracted three times with 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCCC1 | C1CCCCC1 | c1ccccc1.c1ccccc1.C1CCCCC1 | null | CO | null | 3 | N#Cc1ccc(-c2ccc(C3CCC(=O)CC3)cc2)cc1>CO>N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5e5c25f893b444bd9bf8ae43f97a4d3f | C1=COCCC1.N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1>>N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1 | C(#N)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O.O1CCCC=C1.S(=O)(=O)(O[Si](C)(C)C)O[Si](C)(C)C>>O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N | [CH:16]1=[CH:17][CH2:18][CH2:19][CH2:20][O:21]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C@H:11]3[CH2:12][CH2:13][C@H:14]([OH:15])[CH2:22][CH2:23]3)[cH:24][cH:25]2)[cH:26][cH:27]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C@H:11]3[CH2:12][CH2:13][C@H:14]([O:15][CH:16]4[CH2:17][... | C1=COCCC1.N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 | N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | oxa-Michael addition | 7dbeed209463058f59d43728a589e5f7e9550a2179664f08902eb30ad7ba383b | 2683964549e7d2a3e8c7989efc3c7275468eaa2a5d254179937977d9931444d1 | c1ccc(-c2ccc([C@H]3CC[C@H](OC4CCCCO4)CC3)cc2)cc1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[O;H0;D2;+0:9]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1)-[C:10] | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | c1ccccc1.c1ccccc1.C1CCCCC1.C1CCOCC1 | null | ClCCl | 0 | 0.5 | C1=COCCC1.N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1>ClCCl>N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5ec990aeb1174b278ed38ed7122071bb | CCCCCCCC[CH2][Mg][Br].N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1>>CCCCCCCCCC(=O)C1([C@@H]2CC[C@@H](OC3CCCCO3)CC2)C=CC(c2ccccc2)=CC1 | C(CCCCCCCC)[Mg]Br.O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C#N.C(C)OCC.C([O-])([O-])=O.[Na+].[Na+]>>O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C1=CC=CC=C1)C(CCCCCCCCC)=O | [Br][Mg][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].N#C[c:32]1[cH:31][cH:30][c:29](-[c:28]2[cH:27][cH:26][c:12]([C@H:13]3[CH2:14][CH2:15][C@H:16]([O:17][CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:23]4)[CH2:24][CH2:25]3)[cH:36][cH:35]2)[cH:34][cH:33]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]... | CCCCCCCC[CH2][Mg][Br].N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1 | CCCCCCCCCC(=O)C1([C@@H]2CC[C@@H](OC3CCCCO3)CC2)C=CC(c2ccccc2)=CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 04af596b16355e97e237411bdeb1154630acb9fcbb2e78fba5367d10ca97e773 | 058ec4e66add7fdc073b5e3494733ba135ae11f930334633068285662e0aea54 | C1=CC([C@H]2CC[C@H](OC3CCCCO3)CC2)CC=C1c1ccccc1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9](-[C:10])-[C:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:2):[c:14]:[c:15]:1.[Br]-[Mg]-[CH2;D2;+0:16]-[C:17]-[C:18]>>[C:10]-[C:9](-[C;H0;D4;+0:8]1(-[C:19](=[O;D1;H0:20])-[CH2;D2;+0:16]-[C:17]-[C:18])-[CH2;D2;+0:12]-[CH;D2... | null | [] | null | null | null | null | A solution of nonylmagnesium bromide (8.3 mmol) in 30 ml of diethyl ether was treated at 0° C. with a solution of 1.5 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 15 ml of tetrahydrofuran. The reaction mixture was heated at slight reflux overnight and then treated with dilute sodium carbona... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Nitrile | Ketone | c1ccccc1.c1ccccc1 | C1=CCCC=C1.c1ccccc1 | C1CCCCC1.C1CCOCC1.C1=CCCC=C1.c1ccccc1 | Br-.Mg | O1CCCC1 | null | null | CCCCCCCC[CH2][Mg][Br].N#Cc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1>O1CCCC1>CCCCCCCCCC(=O)C1([C@@H]2CC[C@@H](OC3CCCCO3)CC2)C=CC(c2ccccc2)=CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5644e5fd1d534b5297d22337a4455595 | CCCCCCCCCCc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1>>CCCCCCCCCCc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 | O1C(CCCC1)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCCCCCCCCC.S(=O)(=O)(O[Si](C)(C)C)O[Si](C)(C)C.N1=CC=CC=C1>>C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O | C1CCC([O:23][C@H:22]2[CH2:21][CH2:20][C@H:19]([c:18]3[cH:17][cH:16][c:15](-[c:14]4[cH:13][cH:12][c:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:29][cH:28]4)[cH:27][cH:26]3)[CH2:25][CH2:24]2)OC1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:1... | CCCCCCCCCCc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1 | CCCCCCCCCCc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 | null | null | ClCCl.CO.C(C)OCC | Reduction | OtherReaction | 0b83bf1290e2ee90e436d69e159e123816ec005a202c40da90352984400ae7f0 | 628b56b3f4fed40b9cc8e2f7565bcae98d5e36a3f75394461dabd987fb619482 | c1ccc(-c2ccc(C3CCCCC3)cc2)cc1 | [C:1]-[C:2](-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1)-[C:4]>>[C:1]-[C:2](-[OH;D1;+0:3])-[C:4] | 50.6 | [{"value": 50.6, "product": "C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Secondary alcohol | C1CCOCC1 | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | ClCCl.CO.C(C)OCC | null | 2 | CCCCCCCCCCc1ccc(-c2ccc([C@@H]3CC[C@@H](OC4CCCCO4)CC3)cc2)cc1>ClCCl.CO.C(C)OCC>CCCCCCCCCCc1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d52c9a4f0084f87b782e403815be67c | BrBr.CCCCCCCCCCc1cnc(-c2ccc(O)cc2)nc1>>CCCCCCCCCCc1cnc(-c2ccc(O)c(Br)c2)nc1 | C(CCCCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)O.BrBr.O>>BrC1=C(C=CC(=C1)C1=NC=C(C=N1)CCCCCCCCCC)O | Br[Br:21].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][c:11]1[cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:22]2)[n:23][cH:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][c:11]1[cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([OH:19])[c:20]([... | BrBr.CCCCCCCCCCc1cnc(-c2ccc(O)cc2)nc1 | CCCCCCCCCCc1cnc(-c2ccc(O)c(Br)c2)nc1 | null | null | ClCCl | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2ncccn2)cc1 | Br-[Br;H0;D1;+0:1].[O;D1;H1:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[O;D1;H1:2]):[c:4] | 76.6 | [{"value": 76.6, "product": "BrC1=C(C=CC(=C1)C1=NC=C(C=N1)CCCCCCCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 5 g of 4-(5-decyl-2-pyrimidinyl)phenol in 50 ml of dichloromethane was treated at 0° C. while gassing with argon with a solution of 2.6 g of bromine in 50 ml of dichloromethane. The reaction mixture was stirred for a further 2 hours and then treated with water. The organic phase was separated and the aque... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1cncnc1.c1ccccc1 | HBr | ClCCl | null | 2 | BrBr.CCCCCCCCCCc1cnc(-c2ccc(O)cc2)nc1>ClCCl>CCCCCCCCCCc1cnc(-c2ccc(O)c(Br)c2)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-93d2d1036cf4487bb97588f4d5c4c71e | COc1ccc(CC[C@@H]2CC[C@@H](O)CC2)cc1>>Oc1ccc(CC[C@@H]2CC[C@@H](O)CC2)cc1 | B(Br)(Br)Br.COC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)O>>OC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)O | C[O:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][C@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[CH2:13][CH2:14]2)[cH:15][cH:16]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][C@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[CH2:13][CH2:14]2)[cH:15][cH:16]1 | COc1ccc(CC[C@@H]2CC[C@@H](O)CC2)cc1 | Oc1ccc(CC[C@@H]2CC[C@@H](O)CC2)cc1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCC2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 73.7 | [{"value": 73.7, "product": "OC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 7.5 g trans-4-(2-[4-methoxyphenyl]ethyl)cyclohexanol and 100 ml of dichloromethane was treated at 0° C. with 27 ml of a 1M solution of boron tribromide in dichloromethane. The reaction mixture was stirred at room temperature for a further 2 hours and then poured on to ice-water. The organic phase was separ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CCCCC1 | Other | ClCCl | null | 2 | COc1ccc(CC[C@@H]2CC[C@@H](O)CC2)cc1>ClCCl>Oc1ccc(CC[C@@H]2CC[C@@H](O)CC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f2f18a0c6a1488a9177a1834c0193c2 | CCCCCC[C@@H](C)OC(=O)c1ccc(-c2ccc(C3CCC(=O)CC3)cc2)cc1>>CCCCCC[C@@H](C)OC(=O)c1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 | [BH4-].[Na+].C[C@H](CCCCCC)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C1CCC(CC1)=O.Cl>>C[C@H](CCCCCC)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[O:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH:20]3[CH2:21][CH2:22][C:23](=[O:24])[CH2:25][CH2:26]3)[cH:27][cH:28]2)[cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[O:9][C:10](=[O:11])[c:12]1[cH:13][... | CCCCCC[C@@H](C)OC(=O)c1ccc(-c2ccc(C3CCC(=O)CC3)cc2)cc1 | CCCCCC[C@@H](C)OC(=O)c1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 | null | null | COCCOC | Reduction | Reduction of ketone to secondary alcohol | 2851cada23ce4ae5bca04d1ef48c1473fe285273d9a82803d040df273fff8e79 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2ccc(C3CCCCC3)cc2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6]>>[C:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6] | null | [] | null | null | 30 | MINUTE | A suspension of 0.14 g of sodium borohydride in 10 ml of 1,2-dimethoxyethane was treated at 0° C. with a solution of 4-(4'-[(R)-2-octyl]oxycarbonyl-4-biphenylyl)cyclohexanone in 10 ml of 1,2-dimethoxyethane. The reaction mixture was stirred at room temperature for a further 30 minutes and then treated with 25% hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCCC1 | C1CCCCC1 | c1ccccc1.c1ccccc1.C1CCCCC1 | null | COCCOC | null | 0.5 | CCCCCC[C@@H](C)OC(=O)c1ccc(-c2ccc(C3CCC(=O)CC3)cc2)cc1>COCCOC>CCCCCC[C@@H](C)OC(=O)c1ccc(-c2ccc([C@@H]3CC[C@@H](O)CC3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-559f69803bbe4b658724c6bc142b64a7 | CCOC(=O)N=C1SC(CBr)CN1c1cccc(C(F)(F)F)c1>>CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)CBr.CC(C)([O-])C.[K+]>>C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C | Br[CH2:10][CH:9]1[S:8][C:7](=[N:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:12]([c:13]2[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]2)[CH2:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[c:7]1[s:8][c:9]([CH3:10])[cH:11][n:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1 | CCOC(=O)N=C1SC(CBr)CN1c1cccc(C(F)(F)F)c1 | CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | null | null | C(C)(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | 62091df025a1f87682a619edf4cff7b6d2b3ef505a6f828aecadb6203b1e934e | 1999dad80e5076a6966678656829dfaaeb81d275138c28f17c08501fabddc05b | N=c1sccn1-c1ccccc1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[N;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9])-[C;H0;D3;+0:10](=[#7:11]-[C:12](-[#8:13])=[O;D1;H0:14])-[S;H0;D2;+0:15]-1>>[#8:13]-[C:12](=[O;D1;H0:14])-[#7:11]=[c;H0;D3;+0:10]1:[s;H0;D2;+0:15]:[c;H0;D3;+0:2](-[CH3;D1;+0:1]):[cH;D2;+0:3]:[n;H0;D3;+0:4]:1-[c;H0;D3;+... | 64 | [{"value": 64.0, "product": "C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromomethylthiazolidine (0.7 g) and potassium t-butoxide (0.25 g) in t-butanol (30 ml) was refluxed for 5 hours. After removal of the solvent under reduced pressure, the concentrated residue was extracted with chlorofom (100 ml), washed with water and dr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine.Monosulfide | null | C1CSC[NH]1 | c1cscn1 | c1cscn1.c1ccccc1 | HBr | C(C)(C)(C)O | null | null | CCOC(=O)N=C1SC(CBr)CN1c1cccc(C(F)(F)F)c1>C(C)(C)(C)O>CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b3ec2847d438470ca46e18bcfaff73b8 | C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)OCC)S1>>CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C.C[O-].[Na+]>>C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[C:7]1[S:8][C:9](=[CH2:10])[CH2:11][N:12]1[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[c:7]1[s:8][c:9]([CH3:10])[cH:11][n:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1 | C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)OCC)S1 | CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | bc22ec4e064d03b756a8d25e6a4a6c6224c78dd24c6fbc51dd861d527c1c25cc | 52425f6c64e57e44cd5432c544f026330c87adfd083722c96785deb8be64fd8d | N=c1sccn1-c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]=[C;H0;D3;+0:6]1-[S;H0;D2;+0:7]-[C;H0;D3;+0:8](=[CH2;D1;+0:9])-[CH2;D2;+0:10]-[N;H0;D3;+0:11]-1-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]=[c;H0;D3;+0:6]1:[s;H0;D2;+0:7]:[c;H0;D3;+0:8](-[CH3;D1;+0:9]):[cH;D2;+0:10]:[n;H0;D3;+0:11]:1-[c;H... | 80 | [{"value": 80.0, "product": "C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-ethoxycarbonylimino-3-(3-tri-fluoromethylphenyl)-5-methylenethiazolidine (2.0 g) and sodium methoxide (28 % methanolic solution; 1.2 g) in ethanol (50 ml) was refluxed for 30 minutes. After removal of the solvent under reduced pressure, the concentrated residue was extracted with chlorofom (200 ml), was... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Monosulfide.Vinyl | null | C1CSC[NH]1 | c1cscn1 | c1cscn1.c1ccccc1 | null | C(C)O | null | null | C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)OCC)S1>C(C)O>CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0a08060894534fcf90c2c7601f6e0e43 | CC(C)CC(=O)Cl.CCc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1>>CCc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)CC(C)C)s1 | N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC.C(C)N(CC)CC.C(CC(C)C)(=O)Cl>>C(CC(C)C)(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC | Cl[C:18](=[O:19])[CH2:20][CH:21]([CH3:22])[CH3:23].[CH3:1][CH2:2][c:3]1[cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[c:16](=[NH:17])[s:24]1>>[CH3:1][CH2:2][c:3]1[cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[c:16](=[N:17][C:18](=[O:19])[CH2:20][CH... | CC(C)CC(=O)Cl.CCc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 | CCc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)CC(C)C)s1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | N=c1sccn1-c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH;D1;+0:5]=[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1-[c:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D2;+0:5]=[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1-[c:11] | 30.6 | [{"value": 30.6, "product": "C(CC(C)C)(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-imino-3-(3-trifluoromethylphenyl)-5-ethylthiazoline (0.5 g) and triethylamine (0.6 g) in chloroform (30 ml), isovaleryl chloride (0.8 g) was dropwise added under stirring at room temperature, and stirring was continued for 2 hours. After removal of the solvent under reduced pressure, the concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | c1cscn1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 2 | CC(C)CC(=O)Cl.CCc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1>C(Cl)(Cl)Cl>CCc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)CC(C)C)s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8c02e4c5d0114a13a64c527fd72cc67f | Cc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1.O=C(O)C(F)F>>Cc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)C(F)F)s1 | Cl.N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C.C(C)N(CC)CC.Cl.C(C)N=C=NCCCN(C)C.FC(C(=O)O)F>>FC(C(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C)F | [CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15](=[NH:16])[s:22]1.O[C:17](=[O:18])[CH:19]([F:20])[F:21]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15](=[N:16][C:17](=[O:18])[CH:19]([F:20])[F:21])[s:22]1 | Cc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1.O=C(O)C(F)F | Cc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)C(F)F)s1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | db5387e6a0a70df402c1de47d784ebd77c0df6ea444556bcb68e6c99ac233dfc | d6b6da3f4e6a1bff80118626f0eda39fc948645429a79c2af70ffd0ea7000442 | N=c1sccn1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])-[F;D1;H0:5].[NH;D1;+0:6]=[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1-[c:12]>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D2;+0:6]=[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1-[c:12] | 62.6 | [{"value": 62.6, "product": "FC(C(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline hydrochloride (0.42 g), triethylamine (2.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.8 g) and difluoroacetic acid (0.75 g) in chloroform (10 ml) was refluxed for 8 hours. The residue was washed with aqueous hydrochloric acid an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1cscn1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | Cc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1.O=C(O)C(F)F>C(Cl)(Cl)Cl>Cc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)C(F)F)s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-71db743facde4273a10efe6831ec5332 | CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1>>COC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C.C[O-].[Na+]>>COC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C | C[CH2:1][O:2][C:3](=[O:4])[N:5]=[c:6]1[s:7][c:8]([CH3:9])[cH:10][n:11]1-[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[N:5]=[c:6]1[s:7][c:8]([CH3:9])[cH:10][n:11]1-[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | COC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | null | null | CO | Miscellaneous | Transesterification | 4aaa63d92793bb3347780900c7890c124a30137b2f711b41f0f3898a6907ad65 | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | N=c1sccn1-c1ccccc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](-[#7:4])=[O;D1;H0:5]>>[#7:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH3;D1;+0:1] | 83.5 | [{"value": 83.5, "product": "COC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.0 g) and sodium methoxide (28 % methanolic solution; 0.6 g) in methanol (30 ml) was refluxed for 10 hours. After removal of the solvent, the residue was extracted with chloroform (100 ml), washed with water and dried over anhydrous ma... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | null | null | c1cscn1.c1ccccc1 | Other | CO | null | null | CCOC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1>CO>COC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c966fd28018643419cf0ed25971fd628 | C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)NCC)S1>>CCNC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | C(C)NC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C.C[O-].[Na+]>>C(C)NC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[N:6]=[C:7]1[S:8][C:9](=[CH2:10])[CH2:11][N:12]1[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[N:6]=[c:7]1[s:8][c:9]([CH3:10])[cH:11][n:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1 | C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)NCC)S1 | CCNC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | bc22ec4e064d03b756a8d25e6a4a6c6224c78dd24c6fbc51dd861d527c1c25cc | 52425f6c64e57e44cd5432c544f026330c87adfd083722c96785deb8be64fd8d | N=c1sccn1-c1ccccc1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]=[C;H0;D3;+0:6]1-[S;H0;D2;+0:7]-[C;H0;D3;+0:8](=[CH2;D1;+0:9])-[CH2;D2;+0:10]-[N;H0;D3;+0:11]-1-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]=[c;H0;D3;+0:6]1:[s;H0;D2;+0:7]:[c;H0;D3;+0:8](-[CH3;D1;+0:9]):[cH;D2;+0:10]:[n;H0;D3;+0:11]:1-[c;H... | 50 | [{"value": 50.0, "product": "C(C)NC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-(N-ethylcarbamoylimino)-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (0.2 g) and sodium methoxide (28 % methanolic solution; 0.2 g) in methanol (30 ml) was refluxed for 10 hours. After removal of the solvent, the residue was extracted with chloroform (100 ml), washed with water and dried over anh... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Monosulfide.Vinyl | null | C1CSC[NH]1 | c1cscn1 | c1cscn1.c1ccccc1 | null | CO | null | null | C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)NCC)S1>CO>CCNC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-be24221918f44d34a8f5c8d9a0afeeda | CCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1.O=C1CCC(=O)N1Br>>CCOC(=O)N=c1sc(Br)cn1-c1cccc(C(F)(F)F)c1 | C(C)OC(=O)N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F.BrN1C(CCC1=O)=O>>C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)Br | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[C:7]1[S:8][CH2:9][CH2:11][N:12]1[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[c:7]1[s:8][c:9]([Br:10])[cH:11][n:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1 | CCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1.O=C1CCC(=O)N1Br | CCOC(=O)N=c1sc(Br)cn1-c1cccc(C(F)(F)F)c1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 0955a092bec3064de2a1953594a177fed6d0e6f5c54c728133fb3d756196dca1 | fe6124e6da27d4ba11ef739427f2beb5af6ae35c84f1c7dcf9e552e7a8eb412f | N=c1sccn1-c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]=[C;H0;D3;+0:7]1-[S;H0;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[N;H0;D3;+0:11]-1-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[n;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c;H0;D3;+... | 45.3 | [{"value": 45.3, "product": "C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazolidine (1.6 g) and N-bromosuccinimide (2 g) in chloroform (50 ml) was refluxed for 10 hours. After cooling, the reaction mixture was washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. The solvent was removed und... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Tertiary amine.Monosulfide | Aromatic halide | C1CSC[NH]1.C1CCNC1 | c1cscn1 | c1cscn1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)Cl>CCOC(=O)N=c1sc(Br)cn1-c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f26ce1c4575d4a3f9dcbacba0e49b836 | CCOC(=O)N=c1sccn1-c1cccc(C(F)(F)F)c1.O=C1CCC(=O)N1I>>CCOC(=O)N=c1sc(I)cn1-c1cccc(C(F)(F)F)c1 | C(C)OC(=O)N=C1SC=CN1C1=CC(=CC=C1)C(F)(F)F.IN1C(CCC1=O)=O>>C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)I | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[c:7]1[s:8][cH:9][cH:11][n:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1.O=C1CCC(=O)N1[I:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[c:7]1[s:8][c:9]([I:10])[cH:11][n:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1 | CCOC(=O)N=c1sccn1-c1cccc(C(F)(F)F)c1.O=C1CCC(=O)N1I | CCOC(=O)N=c1sc(I)cn1-c1cccc(C(F)(F)F)c1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 3505c5a135ac37e3769ac5551611b02e62ded9217a3618731c0104022c0bad49 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | N=c1sccn1-c1ccccc1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[c:2]-[#7;a:3]1:[c:4]:[cH;D2;+0:5]:[#16;a:6]:[c:7]:1>>[I;H0;D1;+0:1]-[c;H0;D3;+0:5]1:[#16;a:6]:[c:7]:[#7;a:3](-[c:2]):[c:4]:1 | null | [] | null | null | null | null | A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazoline (0.5 g) and N-iodosuccinimide (0.4 g) in chloroform (30 ml) was refluxed for 20 hours. After cooling, the reaction mixture was washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. The solvent was removed unde... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cscn1.C1CCNC1 | c1cscn1 | c1cscn1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(=O)N=c1sccn1-c1cccc(C(F)(F)F)c1.O=C1CCC(=O)N1I>C(Cl)(Cl)Cl>CCOC(=O)N=c1sc(I)cn1-c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d71d3da489d640ec9419ef589183bfc0 | C#CCBr.Nc1cccc(C(F)(F)F)c1>>C#CCNc1cccc(C(F)(F)F)c1 | FC(C=1C=C(N)C=CC1)(F)F.C(C#C)Br>>C(C#C)NC1=CC(=CC=C1)C(F)(F)F | Br[CH2:3][C:2]#[CH:1].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1>>[CH:1]#[C:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | C#CCBr.Nc1cccc(C(F)(F)F)c1 | C#CCNc1cccc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 34.8 | [{"value": 34.8, "product": "C(C#C)NC1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | A mixture of 3-trifluoromethylaniline (30 g) ad propargyl bromide (12 g) was stirred at 80° C. for 3 hours, followed by filtration of the reaction mixture. The filtrate was subjected to column chromatography to give N-propargyl-3-trifluoromethylaniline (7 g). A solution of N-propargyl-3-trifluoromethylaniline thus obta... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HBr | null | 80 | 3 | C#CCBr.Nc1cccc(C(F)(F)F)c1>>C#CCNc1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8157a175e15e4fbc96068d0c346be2c4 | CCOC(=O)N=C1SC(CBr)CN1c1cccc(C(F)(F)F)c1>>C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)OCC)S1 | C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)CBr.CC(C)([O-])C.[K+]>>C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C | Br[CH2:1][CH:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[C:15](=[N:16][C:17](=[O:18])[O:19][CH2:20][CH3:21])[S:22]1>>[CH2:1]=[C:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[C:15](=[N:16][C:17](=[O:18])[O:19][CH2:20][CH3:21])[S:22]1 | CCOC(=O)N=C1SC(CBr)CN1c1cccc(C(F)(F)F)c1 | C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)OCC)S1 | null | null | C(C)(C)(C)O | Functional Group Interconversion | OtherReaction | 4f0c51a3144578f44438143cc70544d48338ea7255c685a004cde28e3ab8cb7a | 44f6bead9dcc673fd477f954e2462b5f5fd56809e52bfd55b282a26c5c8ee4a5 | C=C1CN(c2ccccc2)C(=N)S1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[#16:3]-[C:4](=[#7:5])-[#7:6](-[c:7])-[C:8]-1>>[#7:5]=[C:4]1-[#16:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:8]-[#7:6]-1-[c:7] | 44.5 | [{"value": 44.5, "product": "C(C)OC(=O)N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromomethylthiazolidine (0.7 g) and potassium t-butoxide (0.25 g) in t-butanol (30 ml) was refluxed for 5 hours, and the solvent was distilled off under reduced pressure. The residue was extracted with chloroform (100 ml), washed with water and dried ove... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Monosulfide | Monosulfide.Vinyl | C1CSC[NH]1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | HBr | C(C)(C)(C)O | null | null | CCOC(=O)N=C1SC(CBr)CN1c1cccc(C(F)(F)F)c1>C(C)(C)(C)O>C=C1CN(c2cccc(C(F)(F)F)c2)C(=NC(=O)OCC)S1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3292278c79b24e9e918e562e44f20d64 | C#CCBr.N#CNc1cccc(C(F)(F)F)c1>>C#CCN(C#N)c1cccc(C(F)(F)F)c1 | C(#N)NC1=CC(=CC=C1)C(F)(F)F.C([O-])([O-])=O.[K+].[K+].C(C#C)Br>>C(#N)N(C1=CC(=CC=C1)C(F)(F)F)CC#C | Br[CH2:3][C:2]#[CH:1].[NH:4]([C:5]#[N:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1>>[CH:1]#[C:2][CH2:3][N:4]([C:5]#[N:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1 | C#CCBr.N#CNc1cccc(C(F)(F)F)c1 | C#CCN(C#N)c1cccc(C(F)(F)F)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7f4592dae7b2f5f0f30acf7e56578962dfb88f986065664b5af1e3804579b9ea | 3ae39d91f370bdde1c68fc1b2e4d08ccebf5eea24230a6cff2ba942acd355f14 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[N;D1;H0:4]#[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]#[N;D1;H0:4])-[c:7](:[c:8]):[c:9] | 63.1 | [{"value": 63.1, "product": "C(#N)N(C1=CC(=CC=C1)C(F)(F)F)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of N-cyano-3-trifluoromethylaniline (5.0 g) in acetone (100 ml), potassium carbonate (7.4 g) and propargyl bromide (3.5 g) were added, and the resultant mixture was stirred at room temperature for 10 hours, followed by filtration of the reaction mixture. The solvent was removed from the filtrate by distil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide | Cyanamide | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | C#CCBr.N#CNc1cccc(C(F)(F)F)c1>CC(=O)C>C#CCN(C#N)c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-270b39e5107f474fb7cc4aaffd104d14 | C#CCN(C#N)c1cccc(C(F)(F)F)c1.S>>C=C1CN(c2cccc(C(F)(F)F)c2)C(=N)S1 | S.C(#N)N(C1=CC(=CC=C1)C(F)(F)F)CC#C.C(C)N(CC)CC>>N=C1SC(CN1C1=CC(=CC=C1)C(F)(F)F)=C | [CH:1]#[C:2][CH2:3][N:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1)[C:15]#[N:16].[SH2:17]>>[CH2:1]=[C:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[C:15](=[NH:16])[S:17]1 | C#CCN(C#N)c1cccc(C(F)(F)F)c1.S | C=C1CN(c2cccc(C(F)(F)F)c2)C(=N)S1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | bbbc66bf070361685cc939aaea8bd4543b58e3a09d401a01a62568ac5804abc3 | b0d2992e1846c9bc93def6cb1afde3755e2ae84ed2b7e88f1ab9142956eef3a4 | C=C1CN(c2ccccc2)C(=N)S1 | [CH;D1;+0:1]#[C;H0;D2;+0:2]-[C:3]-[#7:4](-[c:5])-[C;H0;D2;+0:6]#[N;H0;D1;+0:7].[SH2;D0;+0:8]>>[CH2;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[#7:4](-[c:5])-[C;H0;D3;+0:6](=[NH;D1;+0:7])-[S;H0;D2;+0:8]-1 | null | [] | null | null | null | null | To a solution of N-cyano-3-trifluoromethylaniline (5.0 g) in acetone (100 ml), potassium carbonate (7.4 g) and propargyl bromide (3.5 g) were added, and the resultant mixture was stirred at room temperature for 10 hours, followed by filtration of the reaction mixture. The solvent was removed from the filtrate by distil... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Alkyne | Monosulfide.Vinyl | null | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | null | CO | null | null | C#CCN(C#N)c1cccc(C(F)(F)F)c1.S>CO>C=C1CN(c2cccc(C(F)(F)F)c2)C(=N)S1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-731ffa4941074c3ab5ffbb7afac94057 | CCc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)OC(C)(C)C)s1>>CCc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 | C(C)(C)(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC.FC(C(=O)O)(F)F.C([O-])([O-])=O.[K+].[K+].O>>N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC | CC(C)(C)OC(=O)[N:17]=[c:16]1[n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[cH:4][c:3]([CH2:2][CH3:1])[s:18]1>>[CH3:1][CH2:2][c:3]1[cH:4][n:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[c:16](=[NH:17])[s:18]1 | CCc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)OC(C)(C)C)s1 | CCc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 | null | null | C(Cl)(Cl)Cl | Reduction | Boc amine deprotection | ffcdb7bf4aefeac58ddaef1f8967bb6ac0af00a322ee4ca170683d40109a9a1f | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | N=c1sccn1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D2;+0:1]=[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7]>>[NH;D1;+0:1]=[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7] | 41 | [{"value": 41.0, "product": "N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 2-(t-butoxycarbonylimino)-3-(3-trifluoromethylphenyl)-5-ethylthiazoline (1 g) and trifluoroacetic acid (3 g) in chloroform (20 ml) was stirred at room temperature for 3 hours, followed by addition of water (50 ml) thereto. The resultant mixture was neutralized with potassium carbonate, extracted with chlor... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | null | null | c1cscn1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | 3 | CCc1cn(-c2cccc(C(F)(F)F)c2)c(=NC(=O)OC(C)(C)C)s1>C(Cl)(Cl)Cl>CCc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.