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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ae86ad57c04d47c8a8dfe28f32ee4826 | CCCCCCCC/C=C\CCCCCCCCOC(=O)CCCCCCC/C=C\CCCCCCCC.CCCCCCCCCCCCCCCCOC(=O)CCCCCC(C)C>>CCCCCCCCCCCCCC(=O)OC(C)C | CCCCCCCCCCCCCCCCOC(=O)CCCCCC(C)C.CCCCCCCC/C=C\CCCCCCCCOC(=O)CCCCCCC/C=C\CCCCCCCC>>C(CCCCCCCCCCCCC)(=O)OC(C)C | CCCCCCCC/C=C\CCCCCCCCOC(=O)CCCCCCC/C=C\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].CCCCCCCCCCCCCCCC[O:16][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:17]([CH3:18])[CH3:19])=[O:15]>>[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][C:14](=[O:15])[O:16][CH:1... | CCCCCCCC/C=C\CCCCCCCCOC(=O)CCCCCCC/C=C\CCCCCCCC.CCCCCCCCCCCCCCCCOC(=O)CCCCCC(C)C | CCCCCCCCCCCCCC(=O)OC(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a88a687c4d6b7d2191008916745139c412c118bff64e3926cf21b76bd4b18ba7 | af7b9f47dc4b2fc77b69f8751f8aca252642781fb348457551bd8b9e82cb1ea1 | null | C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[CH;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10].C-C-C-C-C-C-C-C/C=C\C-C-C-C-C-C-C-C-O-C(=O)-C-C-C-C-C-C-C/C=C\[CH2;D2;+0:11]-[C:12]-[C:13]>>[C:3]-[C:2](=[O;D1;H0:4])-[O;H0;D2;+0:1]-[CH;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10].[C:5]-[C... | null | [] | null | null | null | null | cetearyl isononanoate--"Cetiol SN": 8.00 wt. %
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | null | null | null | HO- | null | null | null | CCCCCCCC/C=C\CCCCCCCCOC(=O)CCCCCCC/C=C\CCCCCCCC.CCCCCCCCCCCCCCCCOC(=O)CCCCCC(C)C>>CCCCCCCCCCCCCC(=O)OC(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9ee6fa21344a4a619edbde84bc508fb3 | O=O>>OO | C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2O)O.O=O>>OO.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O | [O:17]=[O:18]>>[OH:17][OH:18] | O=O | OO | null | null | null | Reduction | OtherReaction | 481337b1920f4ce3c43b96146b16128e9761a9eff0de2ea6026c9013b690b60c | 01b4766905dc763de9fb37374ca31d507f6918d1fb0d42f08e9f4930409e0a42 | null | [O;H0;D1;+0:1]=[O;H0;D1;+0:2]>>[OH;D1;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | In all previously known anthraquinone processes, the oxidation reaction and the extraction take place in separate steps, and thus also in separate vessels. The oxidation reaction, in which anthrahydroquinone derivatives react with oxygen, forming hydrogen peroxide and anthraquinone derivatives, takes place in the oxida... | 10.6084/m9.figshare.5104873.v1 | null | null | Peroxide | null | null | null | null | null | null | null | O=O>>OO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-169f88b27a294c15b3d94e8de0e682c6 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C.O=C(Cl)OCCl>>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@](O)(C(=O)OCCl)CC[C@]4(C)[C@H]3CC[C@]12C | ClC(=O)OCCl.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C.N1=CC=CC=C1>>ClCOC(=O)[C@]1(CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCCC(C)C)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@@H:13]3[CH2:14][CH:15]=[C:16]4[CH2:17][C@@H:18]([OH:19])[CH2:25][CH2:26][C@:27]4([CH3:28])[C@H:29]3[CH2:30][CH2:31][C@:32]12[CH3:33].Cl[C:20](=[O:21])[O:22][CH2:23][Cl:24]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:7]... | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C.O=C(Cl)OCCl | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@](O)(C(=O)OCCl)CC[C@]4(C)[C@H]3CC[C@]12C | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | aeb38539b78d1cb51ddf6ba8c84f52c066d749acbc417d09c81bbf5280e7810c | 1249787e3342b915074ab435f92ce681110465e50fefb3d2a861019702951273 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3[C@@H]2C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]=[C:7]1-[C:8]-[C@@H;D3;+0:9](-[O;D1;H1:10])-[C:11]-[C:12]-[C:13]-1>>[C:5]-[C:6]=[C:7]1-[C:8]-[C@;H0;D4;+0:9](-[O;D1;H1:10])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:11]-[C:12]-[C:13]-1 | null | [] | null | null | 24 | HOUR | Chloromethyl chloroformate (1.96 g, 15.2 mmol) and cholesterol (5.0 g, 12.9 mmol) was dissolved in CH2Cl2 (10 ml). The solution was cooled. Pyridine (1.21 g, 15.3 mmol) was dripped into the stirred solution over 5 minutes. Heat was produced and the reaction gave a clear solution from a somewhat unclear starting solutio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary alcohol | Ester | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | HCl | C(Cl)Cl | null | 24 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C.O=C(Cl)OCCl>C(Cl)Cl>CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@](O)(C(=O)OCCl)CC[C@]4(C)[C@H]3CC[C@]12C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2c590b87f0c4656985c4433af338c9a | CC(O)C(=O)O.NCCN>>CC(O)C(=O)NCCNC(=O)C(C)O | C(C(O)C)(=O)O.C(CN)N>>C(CNC(C(O)C)=O)NC(C(O)C)=O | [CH3:1][CH:2]([OH:3])[C:4](=[O:5])[OH:14].[NH2:6][CH2:7][CH2:10][NH2:9]>>[CH3:1][CH:2]([OH:3])[C:4](=[O:5])[NH:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[CH:12]([CH3:13])[OH:14] | CC(O)C(=O)O.NCCN | CC(O)C(=O)NCCNC(=O)C(C)O | null | null | O | Functional Group Addition | OtherReaction | 00fca04d09ae4e202c1fb99d5176ffe098e918f6bb44002a85fd613a55e3c079 | cb4f7707bc4c167a5a17a3069fdab173022aff6b0194447ac4f1de103681f576 | null | [C;D1;H3:1]-[C:2](-[O;D1;H1:3])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[OH;D1;+0:6].[NH2;D1;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH2;D1;+0:10]>>[C;D1;H3:11]-[C:12](-[OH;D1;+0:6])-[C;H0;D3;+0:9](=[O;D1;H0:13])-[NH;D2;+0:10]-[C:14]-[CH2;D2;+0:8]-[NH;D2;+0:7]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:2](-[C;D1;H3:1])-[O;D1;H1:3] | null | [] | 125 | CELSIUS | null | null | Lactic acid (441 g; 4.90 moles) was placed in a reaction flask equipped with a distillation head. Under a nitrogen atmosphere, ethylene diamine (147 g; 2.45 moles) was slowly added with stirring to the reaction flask. During the course of the addition, the reaction mixture turned a deep orange and the temperature reach... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | Secondary amide.Secondary amide.Secondary alcohol | null | null | null | Other | O | 125 | null | CC(O)C(=O)O.NCCN>O>CC(O)C(=O)NCCNC(=O)C(C)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-82348284bdb74ce681d8c47598cef413 | C[C@H](O)C(=O)O>>CC(O)C(=O)O | C([C@@H](O)C)(=O)O.C(C)(=O)OC(C)=O.CCCCC(C(=O)O)O>>C(C(O)C)(=O)O.OC(C(=O)O)CCCC | [CH3:1][C@H:2]([OH:3])[C:4](=[O:5])[OH:6]>>[CH3:1][CH:2]([OH:3])[C:4](=[O:5])[OH:6] | C[C@H](O)C(=O)O | CC(O)C(=O)O | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 140 | CELSIUS | null | null | DL-2-Hydroxycaproic acid (1.00 g, 0.0076 moles), and L-lactic acid (4.5 g of a nominally 85% solution in water; 0.043 moles) were placed in a reaction flask equipped with a distillation head and mechanical stirrer. The flask was heated at 110° C. for 6 hours under low vacuum (aspirator) while water was removed. The tem... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 140 | null | C[C@H](O)C(=O)O>O>CC(O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-727bc53cc8974a99824d9f77e8ab9fbc | C[C@@H]1OC(=O)[C@H](C)OC1=O>>CC(O)C(=O)O | C1(OCCCO1)=O.C(C)(=O)OC(C)=O.C[C@H]1C(=O)O[C@H](C(=O)O1)C.C1(OCCCO1)=O>>C1(OCCCO1)=O.C(C(O)C)(=O)O | C[C@H]1C(=O)[O:3][C@@H:2]([CH3:1])[C:4](=[O:5])[O:6]1>>[CH3:1][CH:2]([OH:3])[C:4](=[O:5])[OH:6] | C[C@@H]1OC(=O)[C@H](C)OC1=O | CC(O)C(=O)O | null | null | O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 3a489c9d1f763ca159b2b2953b45f7bfd439527fe0106b00d52bb92835ce9f92 | 7a1e672e57a6fb97b76aed5dc00cfd545732476349440fff57203dca5fb97d59 | null | C-[C@@H]1-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C@H;D3;+0:4](-[C;D1;H3:5])-[O;H0;D2;+0:6]-C-1=O>>[C;D1;H3:5]-[CH;D3;+0:4](-[OH;D1;+0:6])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 80 | CELSIUS | 8 | HOUR | L-Lactide (85.07 g; 0.945 moles) and water (100 mL; millipore) were placed in a 1 L 3-neck flask equipped with a mechanical stirrer, distillation head, and a thermometer. The reaction mixture was warmed to 80° C. and stirred under nitrogen overnight. The flask was then placed under vacuum (aspirator, 7 mmHg) and the te... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Secondary alcohol | C1COCCO1 | null | null | HO- | O | 80 | 8 | C[C@@H]1OC(=O)[C@H](C)OC1=O>O>CC(O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ec5852a39378408dbba1f53767eea48c | O=C(O)c1ccc2cc(O)ccc2c1>>O=C(O)c1ccc2c(c1)CCC(O)C2 | OC=1C=C2C=CC(=CC2=CC1)C(=O)O.[H][H]>>OC1CC=2C=CC(=CC2CC1)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[cH:10][cH:11][c:12]([OH:13])[cH:14]2>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][CH:12]([OH:13])[CH2:14]2 | O=C(O)c1ccc2cc(O)ccc2c1 | O=C(O)c1ccc2c(c1)CCC(O)C2 | null | [Pd] | O1CCCC1 | Reduction | OtherReaction | 791f5dc0669dd17ea9d12becd21433c9c87a57cda3d5cbebc67920e409dc10b6 | ba6b55202ce8b357d547127b1fb6b7db62ba05b17f20b87243fcfcd8077ff42b | c1ccc2c(c1)CCCC2 | [O;D1;H1:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:8]):[cH;D2;+0:9]:1>>[O;D1;H1:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8])-[CH2;D2;+0:9]-1 | null | [] | null | null | null | null | For example, 6-hydroxynaphthalene-2-carboxylic acid in a solvent such as tetrahydrofuran is reduced with hydrogen gas in the presence of a reducing catalyst such as a palladium/carbon under elevated pressure to obtain 5,6,7,8-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (1).
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Secondary alcohol | c1ccc2ccccc2c1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | null | [Pd].O1CCCC1 | null | null | O=C(O)c1ccc2cc(O)ccc2c1>[Pd].O1CCCC1>O=C(O)c1ccc2c(c1)CCC(O)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eac9be152119468d80a973981c8b50e8 | BrCc1ccccc1.O=C(O)C1CCc2cc(O)ccc2C1>>O=C(O)C1CCc2cc(OCc3ccccc3)ccc2C1 | OC=1C=C2CCC(CC2=CC1)C(=O)O.C(C1=CC=CC=C1)Br.[OH-].[K+]>>C(C1=CC=CC=C1)OC=1C=C2CCC(CC2=CC1)C(=O)O | Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([OH:10])[cH:18][cH:19][c:20]2[CH2:21]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[CH2:21]1 | BrCc1ccccc1.O=C(O)C1CCc2cc(O)ccc2C1 | O=C(O)C1CCc2cc(OCc3ccccc3)ccc2C1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | null | null | The 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid obtained in the above manner is reacted with benzyl bromide in the presence of potassium hydroxide to obtain 1,2,3,4-tetrahydro-6-benzyloxynaphthalene-2-carboxylic acid (11).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HBr | null | null | null | BrCc1ccccc1.O=C(O)C1CCc2cc(O)ccc2C1>>O=C(O)C1CCc2cc(OCc3ccccc3)ccc2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e36c9a7b969845f3b2fcc8a9dfe44e3f | COC(=O)c1ccc2cc(C=O)ccc2c1>>COC(=O)c1ccc2ccccc2c1 | [H][H].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1.COC(=O)C1=CC2=CC=C(C=C2C=C1)C=O.C(Cl)Cl>>COC(=O)C1=CC2=CC=CC=C2C=C1 | O=C[c:10]1[cH:9][c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][c:13]2[cH:12][cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | COC(=O)c1ccc2cc(C=O)ccc2c1 | COC(=O)c1ccc2ccccc2c1 | null | null | O1CCCC1 | Reduction | OtherReaction | e1944dcc31e48b78b2e6da09b819a00b5aec3596b56a43ea4c014a16775d2ab4 | 9b627af1c37cea795d25b24c8b755865edc79a56af73aa7fa1348903b24aee3f | c1ccc2ccccc2c1 | O=C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5] | null | [] | null | null | null | null | For example, 4'-alkoxy-4-bromobiphenyl (17) is reacted with triphenylphosphin to obtain triphenylphosphonium salt of 4'-alkoxybiphenyl (21). The thus obtained triphenylphosphonium salt of 4'-alkoxybiphenyl (21) is reacted with 6-formyl-2-naphthalenecarboxylic acid methyl ester as a solution in such as methylene chlorid... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | Other | O1CCCC1 | null | null | COC(=O)c1ccc2cc(C=O)ccc2c1>O1CCCC1>COC(=O)c1ccc2ccccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf36940ac45c47b1a49e30e635325cb5 | O=C(O)c1ccc2ccccc2c1>>O=C(O)C1CCc2ccccc2C1 | C1=C(C=CC2=CC=CC=C12)C(=O)O.[Na].C(C)OCCOCC>>C1C(CCC2=CC=CC=C12)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13]1 | O=C(O)c1ccc2ccccc2c1 | O=C(O)C1CCc2ccccc2C1 | null | null | null | Reduction | OtherReaction | 4b04a19698815acedc04e64dd177c258cb21c55a1d5303acb9d39585e91e8242 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2c(c1)CCCC2 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9])-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1 | null | [] | null | null | null | null | The thus obtained 6-[4'-alkoxy-4-biphenyl)ethyl]-2-naphthalenecarboxylic acid (22) is hydrogenated in the presence of metal sodium in a solvent such as 1,2-diethoxyethane to obtain 6-[4'-alkoxy-4-biphenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (23). Finally, the resulting 6-[4'-alkoxy-4-biphenyl)ethyl]-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2ccccc2c1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | null | null | null | null | O=C(O)c1ccc2ccccc2c1>>O=C(O)C1CCc2ccccc2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d2c74c555f047899e0fbc54d1163d31 | BrCc1ccccc1.O=C(O)C1CCc2cc(O)ccc2C1>>O=C(O)C1CCc2cc(OCc3ccccc3)ccc2C1 | [OH-].[K+].OC=1C=C2CCC(CC2=CC1)C(=O)O.C(C1=CC=CC=C1)Br.[OH-].[K+].Cl>>C(C1=CC=CC=C1)OC=1C=C2CCC(CC2=CC1)C(=O)O | Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([OH:10])[cH:18][cH:19][c:20]2[CH2:21]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[CH2:21]1 | BrCc1ccccc1.O=C(O)C1CCc2cc(O)ccc2C1 | O=C(O)C1CCc2cc(OCc3ccccc3)ccc2C1 | null | [I-].[Na+] | C(C)O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 92.8 | [{"value": 92.8, "product": "C(C1=CC=CC=C1)OC=1C=C2CCC(CC2=CC1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 10.60 g (50 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid, 12.85 g (75 mmol) of benzyl bromide, 6.6 g (100 mmol) of 85% potassium hydroxide, 0.525 g (3.5 mmol) of sodium iodide, 200 ml of ethanol and 25 ml of distilled water was heated under reflux at 100° C. for 12 hours. To this reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HBr | [I-].[Na+].C(C)O.O | 100 | null | BrCc1ccccc1.O=C(O)C1CCc2cc(O)ccc2C1>[I-].[Na+].C(C)O.O>O=C(O)C1CCc2cc(OCc3ccccc3)ccc2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ccd7d3bc80234865b14e3c2556c0baf6 | CCCCCCCCCCOc1ccc(C(=O)OC2CCc3cc(C(=O)OCc4ccccc4)ccc3C2)cc1>>CCCCCCCCCCOc1ccc(C(=O)OC2CCc3cc(C(=O)O)ccc3C2)cc1 | [H][H].C(C1=CC=CC=C1)OC(=O)C1=CC=2CCC(CC2C=C1)OC(C1=CC=C(C=C1)OCCCCCCCCCC)=O>>C(CCCCCCCCC)OC1=CC=C(C(=O)OC2CC=3C=CC(=CC3CC2)C(=O)O)C=C1 | c1ccc(C[O:27][C:25]([c:24]2[cH:23][c:22]3[c:30]([cH:29][cH:28]2)[CH2:31][CH:19]([O:18][C: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:33][cH:32]2)=[O:17])[CH2:20][CH2:21]3)=[O:26])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH... | CCCCCCCCCCOc1ccc(C(=O)OC2CCc3cc(C(=O)OCc4ccccc4)ccc3C2)cc1 | CCCCCCCCCCOc1ccc(C(=O)OC2CCc3cc(C(=O)O)ccc3C2)cc1 | null | [Pd] | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(OC1CCc2ccccc2C1)c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | 93 | [{"value": 93.0, "product": "C(CCCCCCCCC)OC1=CC=C(C(=O)OC2CC=3C=CC(=CC3CC2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | Hydrogen gas was blown into a mixture of 0.53 g (1.0 mmol) of 6-(4'-decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid benzyl ester, 0.11 g of 5% palladium/carbon and 10 ml of tetrahydrofuran with stirring at room temperature and ordinary pressure for 15 hours. The reaction mixture was filtered using C... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCCC2 | Other | [Pd].O1CCCC1 | null | 15 | CCCCCCCCCCOc1ccc(C(=O)OC2CCc3cc(C(=O)OCc4ccccc4)ccc3C2)cc1>[Pd].O1CCCC1>CCCCCCCCCCOc1ccc(C(=O)OC2CCc3cc(C(=O)O)ccc3C2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-528cd02b7f3644e7b8e580a1f266c8a1 | CCCCCCCCCCOc1ccc2cc(C(=O)O)ccc2c1>>O=C(O)C1CCc2cc(O)ccc2C1 | C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)O.Br>>OC=1C=C2CCC(CC2=CC1)C(=O)O | CCCCCCCCCC[O:10][c:9]1[cH:8][c:7]2[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:14][c:13]2[cH:12][cH:11]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]2[CH2:14]1 | CCCCCCCCCCOc1ccc2cc(C(=O)O)ccc2c1 | O=C(O)C1CCc2cc(O)ccc2C1 | null | null | C(C)(=O)O | Deprotection | OtherReaction | 9479f30b52fd035c72fa7a3953555c10329ae405ac42eb806833d1ea5b6b2ffe | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)CCCC2 | C-C-C-C-C-C-C-C-C-C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:2:[c:14]:1>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[CH;D3;+0:7]1-[CH2;D2;+0:6]-[c:5]2:[c:4]:[c:3]:[c:2](-[OH;D1;+0:1]):[c:14]:[c:13]:2-[CH2;D2;+0:12]-[CH2;D2;+0:11]-1 | 100 | [{"value": 100.0, "product": "OC=1C=C2CCC(CC2=CC1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 16.6 g (50 mmol) of the 6-decyloxynaphthalene-2-carboxylic acid obtained in the first stage was heated under reflux at 130° C. for 7 hours in the presence of 250 cc of acetic acid and 86.5 g (0.5 mol) of 47% hydrobromic acid. To the reaction mixture was added distilled water, and then the resulting mixture was concentr... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccc2ccccc2c1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Other | C(C)(=O)O | null | null | CCCCCCCCCCOc1ccc2cc(C(=O)O)ccc2c1>C(C)(=O)O>O=C(O)C1CCc2cc(O)ccc2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0396fca3395e4ebeb8f2c15f2dea83c8 | CCCCCCCCCCBr.O=C(O)c1ccc(-c2ccc(O)cc2)cc1>>CCCCCCCCCCOc1ccc(-c2ccc(C(=O)O)cc2)cc1 | Cl.OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O.C(CCCCCCCCC)Br.[OH-].[K+].[I-].[Na+].[OH-].[K+]>>C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]2)[cH:25][cH:26]1>>[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[cH:17][cH:18... | CCCCCCCCCCBr.O=C(O)c1ccc(-c2ccc(O)cc2)cc1 | CCCCCCCCCCOc1ccc(-c2ccc(C(=O)O)cc2)cc1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 6 | [{"value": 6.0, "product": "C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 21.4 g (0.1 mol) of 4'-hydroxybiphenyl-4-carboxylic acid, 33.15 g (0.15 mol) of n-decyl bromide, 13.20 g (0.2 mol) of 85% potassium hydroxide, 1.05 g (7 mmol) of sodium iodide, 500 ml of ethanol and 100 ml of distilled water was heated under reflux at 100° C. for 12 hours. After 40 ml of 25% potassium hydr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)O.O | 100 | null | CCCCCCCCCCBr.O=C(O)c1ccc(-c2ccc(O)cc2)cc1>C(C)O.O>CCCCCCCCCCOc1ccc(-c2ccc(C(=O)O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1973f4fcc3e34d7aab97de56c9a9b263 | CCCCCC[C@@H](OC(=O)C1CCc2cc(OCc3ccccc3)ccc2C1)C(F)(F)F>>CCCCCC[C@@H](OC(=O)C1CCc2cc(O)ccc2C1)C(F)(F)F | [H][H].FC([C@@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)OCC1=CC=CC=C1)(F)F>>FC([C@@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)O)(F)F | c1ccc(C[O:17][c:16]2[cH:15][c:14]3[c:20]([cH:19][cH:18]2)[CH2:21][CH:11]([C:9]([O:8][C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:22]([F:23])([F:24])[F:25])=[O:10])[CH2:12][CH2:13]3)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([O:8][C:9](=[O:10])[CH:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([OH:17])[c... | CCCCCC[C@@H](OC(=O)C1CCc2cc(OCc3ccccc3)ccc2C1)C(F)(F)F | CCCCCC[C@@H](OC(=O)C1CCc2cc(O)ccc2C1)C(F)(F)F | null | [Pd] | O1CCCC1 | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)CCCC2 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 100 | [{"value": 100.0, "product": "FC([C@@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Hydrogen gas was blown into a mixture of 8.19 g (18.3 mmol) of the 1,2,3,4-tetrahydro-6-benzyloxynaphthalene-2-carboxylic acid (R)-1-trifluoromethylheptyl ester obtained in the fourth stage, 3.6 g of 5% palladium/carbon as a catalyst and 50 ml of tetrahydrofuran with stirring at room temperature and ordinary pressure f... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2c(c1)CCCC2 | Other | [Pd].O1CCCC1 | null | 24 | CCCCCC[C@@H](OC(=O)C1CCc2cc(OCc3ccccc3)ccc2C1)C(F)(F)F>[Pd].O1CCCC1>CCCCCC[C@@H](OC(=O)C1CCc2cc(O)ccc2C1)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a8ec9300a50c487a97fd5c9549637998 | CCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)cc1.CCCCCC[C@@H](C)OC(=O)C1CCc2cc(O)ccc2C1>>CCCCCCCCc1ccc(-c2ccccc2C(=O)Oc2ccc3c(c2)CCC(C(=O)O[C@H](C)CCCCCC)C3)cc1 | C[C@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)O.C1(CCCCC1)N=C=NC1CCCCC1.C(CCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O.FC([C@@H](CCCCCC)O)(F)F>>C[C@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)OC(=O)C=1C(=CC=CC1)C1=CC=C(C=C1)CCCCCCCC | O[C:19]([c:18]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:44][cH:43]2)[cH:16][cH:17]1)=[O:20].[OH:21][c:22]1[cH:23][cH:24][c:25]2[c:26]([cH:27]1)[CH2:28][CH2:29][CH:30]([C:31](=[O:32])[O:33][C@H:34]([CH3:35])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:... | CCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)cc1.CCCCCC[C@@H](C)OC(=O)C1CCc2cc(O)ccc2C1 | CCCCCCCCc1ccc(-c2ccccc2C(=O)Oc2ccc3c(c2)CCC(C(=O)O[C@H](C)CCCCCC)C3)cc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | a6f963d149e8dd87f63c5bb958cffa4c95c2af472825d9145489a37ba75220bb | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(Oc1ccc2c(c1)CCCC2)c1ccccc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c:7](:[c:8]):[c:9]):[c:10]:[cH;D2;+0:11]:1.[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15])-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:11]:[c:10]:[c;H0;D3;+0:6]:1-[c:7](:[c:8]):[... | null | [] | null | null | 3 | HOUR | To a mixture of 0.31 g (1 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (R)-1-methylheptyl ester obtained as in the fourth stage of Example 23 where R-1-methyl heputanol was used in stead of (R)-1-trifluoromethylheptanol, 0.31 g (1 mmol) of 4'-octylbiphenyl-4-carboxylic acid (FK-1124-8 from Teikoku... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | C(Cl)Cl | null | 3 | CCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)cc1.CCCCCC[C@@H](C)OC(=O)C1CCc2cc(O)ccc2C1>C(Cl)Cl>CCCCCCCCc1ccc(-c2ccccc2C(=O)Oc2ccc3c(c2)CCC(C(=O)O[C@H](C)CCCCCC)C3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-184fb5dc82c740e2b4c51bcf3ae69124 | CCCCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)cc1.CCCCCC[C@@H](C)OC(=O)C1CCc2cc(O)ccc2C1>>CCCCCCCCCCc1ccc(-c2ccccc2C(=O)Oc2ccc3c(c2)CCC(C(=O)O[C@H](C)CCCCCC)C3)cc1 | C[C@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)O.C1(CCCCC1)N=C=NC1CCCCC1.C(CCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O.FC([C@@H](CCCCCC)O)(F)F>>C[C@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)OC(=O)C=1C(=CC=CC1)C1=CC=C(C=C1)CCCCCCCCCC | O[C:21]([c:20]1[cH:17][cH:16][c:15](-[c:14]2[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:46][cH:45]2)[cH:18][cH:19]1)=[O:22].[OH:23][c:24]1[cH:25][cH:26][c:27]2[c:28]([cH:29]1)[CH2:30][CH2:31][CH:32]([C:33](=[O:34])[O:35][C@H:36]([CH3:37])[CH2:38][CH2:39][CH2:40][CH2:... | CCCCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)cc1.CCCCCC[C@@H](C)OC(=O)C1CCc2cc(O)ccc2C1 | CCCCCCCCCCc1ccc(-c2ccccc2C(=O)Oc2ccc3c(c2)CCC(C(=O)O[C@H](C)CCCCCC)C3)cc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | a6f963d149e8dd87f63c5bb958cffa4c95c2af472825d9145489a37ba75220bb | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(Oc1ccc2c(c1)CCCC2)c1ccccc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c:7](:[c:8]):[c:9]):[c:10]:[cH;D2;+0:11]:1.[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15])-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:11]:[c:10]:[c;H0;D3;+0:6]:1-[c:7](:[c:8]):[... | null | [] | null | null | 2.5 | HOUR | To a mixture of 0.37 g (1.1 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (R)-1-methylheptyl ester obtained as in the fourth stage of Example 23 where (R)-1-methyl heputanol was used in stead of (R)-1-trifluoromethylheptanol, 0.33 g (1.1 mmol) of 4'-decylbiphenyl-4-carboxylic acid (FK-1124-10 from ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | C(Cl)Cl | null | 2.5 | CCCCCCCCCCc1ccc(-c2ccc(C(=O)O)cc2)cc1.CCCCCC[C@@H](C)OC(=O)C1CCc2cc(O)ccc2C1>C(Cl)Cl>CCCCCCCCCCc1ccc(-c2ccccc2C(=O)Oc2ccc3c(c2)CCC(C(=O)O[C@H](C)CCCCCC)C3)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cac03ebf9c0047c583eb8f2217093891 | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1Br>>O=C(O)c1ccc(CBr)cc1 | CC1=CC=C(C=C1)C(=O)O.BrN1C(CCC1=O)=O>>BrCC1=CC=C(C(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:10][cH:11]1.O=C1CCC(=O)N1[Br:9]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][Br:9])[cH:10][cH:11]1 | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1Br | O=C(O)c1ccc(CBr)cc1 | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 65.3 | [{"value": 65.0, "product": "BrCC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "BrCC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 39.7 g (287 mmol) of p-toluylic acid, 51.2 g (287 mmol) of N-bromosuccinimide and 2.8 g (11.5 mmol) of dibenzoyl peroxide were suspended in 350 ml of carbon tetrachloride. Then, the resultant mixture was heated with vigorously stirring to perform a reaction under reflux for 2 hours. After completion of the reaction, th... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(C(=O)O)cc1.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl>O=C(O)c1ccc(CBr)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4f7cf5895f954e1fa345200adbbaaa61 | CCCCCCCCCCOc1ccc2cc(C(=O)Oc3ccc(C(=O)OCc4ccccc4)cc3)ccc2c1>>CCCCCCCCCCOc1ccc2cc(C(=O)Oc3ccc(C(=O)O)cc3)ccc2c1 | C(C1=CC=CC=C1)OC(C1=CC=C(C=C1)OC(=O)C1=CC2=CC=C(C=C2C=C1)OCCCCCCCCCC)=O.[H][H]>>C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)OC1=CC=C(C(=O)O)C=C1 | c1ccc(C[O:27][C:25]([c:24]2[cH:23][cH:22][c:21]([O:20][C:18]([c:17]3[cH:16][c:15]4[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:33][c:32]4[cH:31][cH:30]3)=[O:19])[cH:29][cH:28]2)=[O:26])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][... | CCCCCCCCCCOc1ccc2cc(C(=O)Oc3ccc(C(=O)OCc4ccccc4)cc3)ccc2c1 | CCCCCCCCCCOc1ccc2cc(C(=O)Oc3ccc(C(=O)O)cc3)ccc2c1 | null | [Pd] | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)c1ccc2ccccc2c1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | 97.5 | [{"value": 97.5, "product": "C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)OC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 37.6 g (0.07 mol) of the 4-(6-decyloxy-2-naphthoyloxy)benzoic acid benzyl ester obtained in the first stage was added 3.76 g of 5% palladium/carbon, and further added 188 g of THF. Then, hydrogen gas was blown into the mixture. The resultant mixture was stirred overnight and filtered to obtain 30.6 g of 4-(6-decylox... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccc2ccccc2c1.c1ccccc1 | Other | [Pd].C1CCOC1 | null | null | CCCCCCCCCCOc1ccc2cc(C(=O)Oc3ccc(C(=O)OCc4ccccc4)cc3)ccc2c1>[Pd].C1CCOC1>CCCCCCCCCCOc1ccc2cc(C(=O)Oc3ccc(C(=O)O)cc3)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-436174135cd54d56bccd8e2f39d9c63d | CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(OCc4ccccc4)ccc3C2)cc1>>CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(O)ccc3C2)cc1 | C(CCCCCCCCC)OC1=CC=C(C=C1)OC(=O)C1CC2=CC=C(C=C2CC1)OCC1=CC=CC=C1.[H][H]>>C(CCCCCCCCC)OC1=CC=C(C=C1)OC(=O)C1CC2=CC=C(C=C2CC1)O | c1ccc(C[O:25][c:24]2[cH:23][c:22]3[c:28]([cH:27][cH:26]2)[CH2:29][CH:19]([C:17]([O: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:31][cH:30]2)=[O:18])[CH2:20][CH2:21]3)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:1... | CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(OCc4ccccc4)ccc3C2)cc1 | CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(O)ccc3C2)cc1 | null | [Pd] | O1CCCC1 | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Oc1ccccc1)C1CCc2ccccc2C1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 97.7 | [{"value": 97.0, "product": "C(CCCCCCCCC)OC1=CC=C(C=C1)OC(=O)C1CC2=CC=C(C=C2CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.7, "product": "C(CCCCCCCCC)OC1=CC=C(C=C1)OC(=O)C1CC2=CC=C(C=C2CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Then, 0.04 g of 5% palladium/carbon and 10 ml of a tetrahydrofuran solution containing 0.36 g of 2-(4-decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-benzyloxynaphthalene were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was r... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCCC2 | Other | [Pd].O1CCCC1 | null | null | CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(OCc4ccccc4)ccc3C2)cc1>[Pd].O1CCCC1>CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(O)ccc3C2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3241ab6c22d447b498b7ce647cbfc9d9 | CC(=O)O.O=Cc1ccc(C(=O)OCc2ccccc2)cc1>>O=C(O)c1ccc(C(=O)OCc2ccccc2)cc1 | C(C)(=O)O.C(C)(=O)O.C(C1=CC=CC=C1)OC(C1=CC=C(C=C1)C=O)=O>>C(C1=CC=CC=C1)OC(=O)C1=CC=C(C(=O)O)C=C1 | CC(=O)[OH:3].[O:1]=[CH:2][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1 | CC(=O)O.O=Cc1ccc(C(=O)OCc2ccccc2)cc1 | O=C(O)c1ccc(C(=O)OCc2ccccc2)cc1 | null | null | O | Acylation | OtherReaction | d5040721921addb6bab9ff19b117684a5fd543f11d3d76c396d17c6075d19e99 | 300ca3c6bc6ac7a77293ad6cd69ffcaf96f2c9254b40f6adf6415af60ae8f700 | O=C(OCc1ccccc1)c1ccccc1 | C-C(=O)-[OH;D1;+0:1].[O;D1;H0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D3;+0:3](-[OH;D1;+0:1])-[c:4](:[c:5]):[c:6] | 49 | [{"value": 49.0, "product": "C(C1=CC=CC=C1)OC(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 50 ml of an acetic acid solution containing 7.34 g (30.5 mmol) of 4-formylbenzoic acid benzyl ester were dropwise added 4.53 g (4.35 mmol) of chromic acid anhydride, 40 ml of acetic acid and 1.3 ml of water with stirring at room temperature for a period of 2 hours. The oxidation of a formyl group was further carried... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | HO- | O | null | 2 | CC(=O)O.O=Cc1ccc(C(=O)OCc2ccccc2)cc1>O>O=C(O)c1ccc(C(=O)OCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-679c764250d94da2b08939ad59ce9559 | CCCCCC[C@@H](OC(=O)c1ccc(C(=O)OCc2ccccc2)cc1)C(F)(F)F>>CCCCCC[C@@H](OC(=O)c1ccc(C(=O)O)cc1)C(F)(F)F | C(C1=CC=CC=C1)OC(C1=CC=C(C=C1)C(=O)O[C@H](CCCCCC)C(F)(F)F)=O.[H][H]>>FC([C@@H](CCCCCC)OC(=O)C1=CC=C(C(=O)O)C=C1)(F)F | c1ccc(C[O:17][C:15]([c:14]2[cH:13][cH:12][c:11]([C:9]([O:8][C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:20]([F:21])([F:22])[F:23])=[O:10])[cH:19][cH:18]2)=[O:16])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([O:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1)[C:20](... | CCCCCC[C@@H](OC(=O)c1ccc(C(=O)OCc2ccccc2)cc1)C(F)(F)F | CCCCCC[C@@H](OC(=O)c1ccc(C(=O)O)cc1)C(F)(F)F | null | [Pd] | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | 98.9 | [{"value": 98.0, "product": "FC([C@@H](CCCCCC)OC(=O)C1=CC=C(C(=O)O)C=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "FC([C@@H](CCCCCC)OC(=O)C1=CC=C(C(=O)O)C=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Then, 0.07 g of 5% palladium/carbon and 10 ml of a tetrahydrofuran solution containing 0.63 g of 4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid benzyl ester were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was removed... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1 | Other | [Pd].O1CCCC1 | null | null | CCCCCC[C@@H](OC(=O)c1ccc(C(=O)OCc2ccccc2)cc1)C(F)(F)F>[Pd].O1CCCC1>CCCCCC[C@@H](OC(=O)c1ccc(C(=O)O)cc1)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-788333422f5e4a87925a5f9214f163ee | CCCCCC[C@@H](C)OC(=O)c1ccc(C(=O)OCc2ccccc2)cc1>>CCCCCC[C@@H](C)OC(=O)c1ccc(C(=O)O)cc1 | C(C1=CC=CC=C1)OC(C1=CC=C(C=C1)C(=O)O[C@@H](CCCCCC)C)=O.[H][H]>>C[C@H](CCCCCC)OC(=O)C1=CC=C(C(=O)O)C=C1 | c1ccc(C[O:18][C:16]([c:15]2[cH:14][cH:13][c:12]([C:10]([O:9][C@@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH3:8])=[O:11])[cH:20][cH:19]2)=[O:17])cc1>>[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](=[O:17])[OH:18])[cH:19][cH:20]1 | CCCCCC[C@@H](C)OC(=O)c1ccc(C(=O)OCc2ccccc2)cc1 | CCCCCC[C@@H](C)OC(=O)c1ccc(C(=O)O)cc1 | null | [Pd] | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | 99.6 | [{"value": 99.0, "product": "C[C@H](CCCCCC)OC(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "C[C@H](CCCCCC)OC(=O)C1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Then, 0.12 g of 5% palladium/carbon and 30 ml of a tetrahydrofuran solution containing 1.21 g of 4-((R)-1-methylheptyloxycarbonyl)benzoic acid benzyl ester were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was removed using Ce... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1 | Other | [Pd].O1CCCC1 | null | null | CCCCCC[C@@H](C)OC(=O)c1ccc(C(=O)OCc2ccccc2)cc1>[Pd].O1CCCC1>CCCCCC[C@@H](C)OC(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c8e403a545964087ba37eaf4049bc15b | CCCCCCCCCCOc1ccc(-c2ccc(C(=O)O)cc2)cc1>>CCCCCCCCCCOc1ccc(-c2ccc(CO)cc2)cc1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O>>OCC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCCCC | O=[C:20]([c:19]1[cH:18][cH:17][c: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:25][cH:24]2)[cH:23][cH:22]1)[OH:21]>>[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[cH:17][cH:18][c:19]([... | CCCCCCCCCCOc1ccc(-c2ccc(C(=O)O)cc2)cc1 | CCCCCCCCCCOc1ccc(-c2ccc(CO)cc2)cc1 | null | null | C(C)OCC | 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] | null | [] | null | null | null | null | 0.81 g (21.34 mmol) of LiAlH4 was introduced into 40 ml of diethyl ether and stirred. To the mixture was dropwise added a solution, prepared by introducing 1.71 g (5.06 mmol) of 4'-decyloxy-4-biphenylcarboxylic acid obtained in the first stage of Example 11 into 30 ml of diethyl ether, at room temperature over a period... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C(C)OCC | null | null | CCCCCCCCCCOc1ccc(-c2ccc(C(=O)O)cc2)cc1>C(C)OCC>CCCCCCCCCCOc1ccc(-c2ccc(CO)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3104bd09c2f7414fbbfc325719b77c64 | Br.CCCCCCCCCCOc1ccc(-c2ccc(CO)cc2)cc1>>CCCCCCCCCCOc1ccc(-c2ccc(CBr)cc2)cc1 | OCC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCCCC.Br>>BrCC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCCCC | [BrH:21].O[CH2:20][c:19]1[cH:18][cH:17][c: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:25][cH:24]2)[cH:23][cH:22]1>>[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[cH:17][cH:18][c:19](... | Br.CCCCCCCCCCOc1ccc(-c2ccc(CO)cc2)cc1 | CCCCCCCCCCOc1ccc(-c2ccc(CBr)cc2)cc1 | null | null | null | Miscellaneous | OtherReaction | cd3478bc4d4e901afd9352e983cdb4ff4c2fc601772cf0af2f0553c983f9121c | 9b4091cd4cf205a0767d592c748f58d9aed076d9567056ed2bfdc4af71bd7267 | c1ccc(-c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[BrH;D0;+0:5]>>[Br;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | To 0.81 g (2.51 mmol) of 4-hydroxymethyl-4'-decyloxybiphenyl was added 15 ml of an aqueous solution containing 47% HBr, and then healed at 115° C. for 3 hours. After completion of the reaction, the resultant mixture was extracted with ether and washed with water, which was further washed with an aqueous solution contai... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | 3 | Br.CCCCCCCCCCOc1ccc(-c2ccc(CO)cc2)cc1>>CCCCCCCCCCOc1ccc(-c2ccc(CBr)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3bb66da6f37b43aebd4a5504e234b1f4 | CC(C)[C@H](N)C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-]>>CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O | N[C@@H](CS)C(=O)O.N[C@@H](C(C)C)C(=O)O.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC=3C=CC=CC3)C(=O)[O-])C.[K+]>>CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CCC[C@@H](C(=O)O)N)C(=O)O)C | C[CH:12]([CH3:11])[C@H:13]([NH2:14])[C:15](=[O:16])[OH:17].c1ccc([CH2:10][C:8]([NH:7][C@H:6]2[C@H:5]3[S:4][C:2]([CH3:1])([CH3:3])[C@H:21]([C:22](=[O:23])[O-:24])[N:20]3[C:18]2=[O:19])=[O:9])cc1>>[CH3:1][C:2]1([CH3:3])[S:4][C@@H:5]2[C@H:6]([NH:7][C:8](=[O:9])[CH2:10][CH2:11][CH2:12][C@H:13]([NH2:14])[C:15](=[O:16])[OH:1... | CC(C)[C@H](N)C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-] | CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O | null | null | null | C-C Coupling | OtherReaction | b1c5a75836252e474a37fcf494cff25f4048b2f6fdb0bbc647b8a649fa439615 | 0a3570e04fbe6a3b2ffc12a820c50434dd728efb01bf353938ae9117a6d26a85 | O=C1C[C@H]2SCCN12 | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-[C:3](-[N;D1;H2:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[O-;H0;D1:8]-[C:9](=[O;D1;H0:10])-[C:11]-[#7:12]-[C:13](=[O;D1;H0:14])-[C:15]-[#7:16]-[C:17](=[O;D1;H0:18])-[CH2;D2;+0:19]-c1:c:c:c:c:c:1>>[N;D1;H2:4]-[C:3](-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:19]-[C:17](=[O;D1;H0:18])-[#7:16]-[C:15]... | null | [] | null | null | null | null | The first two steps in the biosynthesis of penicillin in P. chrysogenum are the condensation of the three amino acids L-5-amino-5-carboxypentanoic acid (L-α-aminoadipic acid) (A), L-cysteine (C) and L-valine (V) into the tripeptide LLD-ACV, followed by cyclization of this tripeptide to form isopenicillin N. This compou... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | null | C1CN2CC[C@H]2S1 | Other | null | null | null | CC(C)[C@H](N)C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-]>>CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95c128d17561404a9f727a241cd8c7d9 | COC(=O)N[C@@H](Cc1ccccc1)C(=O)CCl>>COC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CCl | [OH-].[Na+].ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O.S(O)(O)(=O)=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O>>ClC[C@H]([C@H](CC1=CC=CC=C1)NC(=O)OC)O | [CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[CH2:16][Cl:17]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C@H:14]([OH:15])[CH2:16][Cl:17] | COC(=O)N[C@@H](Cc1ccccc1)C(=O)CCl | COC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CCl | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5](-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9]-[Cl;D1;H0:10]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5](-[C:6])-[C@H;D3;+0:7](-[OH;D1;+0:8])-[C:9]-[Cl;D1;H0:10] | 67 | [{"value": 67.0, "product": "ClC[C@H]([C@H](CC1=CC=CC=C1)NC(=O)OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | A culture was obtained by the same method as in Example 1 using Geotrichum eriense ATCC 22311 as the microorganism and then adjusted to pH 6 with an aqueous sodium hydroxide solution and an aqueous sulfuric acid solution. A 25-ml portion of this culture, 1 g of glucose and (3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | null | null | 24 | COC(=O)N[C@@H](Cc1ccccc1)C(=O)CCl>>COC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dfb2793f61924a0a99912919753f0f33 | COC(=O)N[C@@H](Cc1ccccc1)C(=O)CCl>>COC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CCl | [OH-].[Na+].S(O)(O)(=O)=O.ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O>>ClC[C@H]([C@H](CC1=CC=CC=C1)NC(=O)OC)O | [CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[CH2:16][Cl:17]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C@H:14]([OH:15])[CH2:16][Cl:17] | COC(=O)N[C@@H](Cc1ccccc1)C(=O)CCl | COC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CCl | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5](-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9]-[Cl;D1;H0:10]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5](-[C:6])-[C@H;D3;+0:7](-[OH;D1;+0:8])-[C:9]-[Cl;D1;H0:10] | 61 | [{"value": 61.0, "product": "ClC[C@H]([C@H](CC1=CC=CC=C1)NC(=O)OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | A culture was obtained by the same method as in Example 1 using Candida gropengiesseri IFO 0659 as the microorganism and adjusted to pH 6 with an aqueous sodium hydroxide solution and an aqueous sulfuric acid solution. A 75-ml portion of this culture was separated into a supernatant and cells by centrifugation. To the ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | null | null | 24 | COC(=O)N[C@@H](Cc1ccccc1)C(=O)CCl>>COC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b36cf4c3fce444e59afcc58bc7669a0f | O=C[C@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO>>O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | C(C)O.C(C)O.O=C[C@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO>>O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | [O:1]=[CH:2][C@H:3]([OH:4])[C@@H:5]([OH:6])[C@H:9]([OH:10])[CH2:11][OH:12].O=C[C@H](O)[C@@H](O)[C@@H:7](CO)[OH:8]>>[O:1]=[CH:2][C@H:3]([OH:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]([OH:10])[CH2:11][OH:12] | O=C[C@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | null | null | null | C-C Coupling | OtherReaction | da8253d53c446f50e056a5337582998833688785c7190c36df3d409121ea7fb8 | a1a0b3762b3789a70fef4edbf46bd73cf56ea18179ec70debe5450d925b63f0f | null | null | null | [] | null | null | null | null | The results presented in FIG. 2 show that in contrast to the control strain containing the shuttle vector alone (CP4[pZB 186]), the recombinant containing the added xylose isomerase, xylulokinase, transaldolase and transketolase genes demonstrated growth and ethanol production from xylose as a carbon source. The recomb... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | null | HO- | null | null | null | O=C[C@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)CO>>O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1000e40f2db412d9d636d6f712f48b1 | CC(=O)c1cccs1.NNc1ccc(F)cc1>>CC(=NNc1ccc(F)cc1)c1cccs1 | Cl.FC1=CC=C(C=C1)NN.C(C)(=O)C=1SC=CC1>>FC1=CC=C(C=C1)NN=C(C)C=1SC=CC1 | O=[C:2]([CH3:1])[c:12]1[cH:13][cH:14][cH:15][s:16]1.[NH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1>>[CH3:1][C:2](=[N:3][NH:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][s:16]1 | CC(=O)c1cccs1.NNc1ccc(F)cc1 | CC(=NNc1ccc(F)cc1)c1cccs1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 83882590079d324612170330ec542715e8ce71411b1b2946e5f0d75ea75ad4dd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | C(=NNc1ccccc1)c1cccs1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[#7:8]-[c:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[#7:8]-[c:9])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | null | null | This compound is prepared from commercial 4-fluorophenylhydrazine hydrochloride (Aldrich) and from commercial 2-acetylthiophene (Aldrich), according to the procedure 1.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | null | null | c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1cccs1.NNc1ccc(F)cc1>>CC(=NNc1ccc(F)cc1)c1cccs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-661c1c44ce674dabb8690fdab4920af6 | CC(=O)c1cccs1.NNc1cccc(F)c1>>CC(=NNc1cccc(F)c1)c1cccs1 | Cl.FC=1C=C(C=CC1)NN.C(C)(=O)C=1SC=CC1>>FC=1C=C(C=CC1)NN=C(C)C=1SC=CC1 | O=[C:2]([CH3:1])[c:12]1[cH:13][cH:14][cH:15][s:16]1.[NH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1>>[CH3:1][C:2](=[N:3][NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1)[c:12]1[cH:13][cH:14][cH:15][s:16]1 | CC(=O)c1cccs1.NNc1cccc(F)c1 | CC(=NNc1cccc(F)c1)c1cccs1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 83882590079d324612170330ec542715e8ce71411b1b2946e5f0d75ea75ad4dd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | C(=NNc1ccccc1)c1cccs1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[#7:8]-[c:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[#7:8]-[c:9])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | null | null | This compound is prepared from commercial 3-fluorophenylhydrazine hydrochloride (Aldrich) and from commercial 2-acetylthiophene (Aldrich), according to the procedure 1.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | null | null | c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1cccs1.NNc1cccc(F)c1>>CC(=NNc1cccc(F)c1)c1cccs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b1c4c35e4d754049b51187394fb98649 | CC(=O)c1ccc[se]1.NNc1ccccc1>>CC(=NNc1ccccc1)c1ccc[se]1 | Cl.C1(=CC=CC=C1)NN.C(C)(=O)C=1[Se]C=CC1>>C1(=CC=CC=C1)NN=C(C)C=1[Se]C=CC1 | O=[C:2]([CH3:1])[c:11]1[cH:12][cH:13][cH:14][se:15]1.[NH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][C:2](=[N:3][NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][se:15]1 | CC(=O)c1ccc[se]1.NNc1ccccc1 | CC(=NNc1ccccc1)c1ccc[se]1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 83882590079d324612170330ec542715e8ce71411b1b2946e5f0d75ea75ad4dd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | C(=NNc1ccccc1)c1ccc[se]1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#34;a:5]:[c:6].[NH2;D1;+0:7]-[#7:8]-[c:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[#7:8]-[c:9])-[c:3](:[c:4]):[#34;a:5]:[c:6] | null | [] | null | null | null | null | This compound is prepared from commercial phenylhydrazine hydrochloride (Aldrich) and 2-acetylselenophene, which is itself obtained according to the procedure described by S. Umezawa (reference 18).
Conditions: See reaction.notes.procedure_details.
Workup: obtained | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | null | null | c1ccccc1.c1cc[se]c1 | HO- | null | null | null | CC(=O)c1ccc[se]1.NNc1ccccc1>>CC(=NNc1ccccc1)c1ccc[se]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c8e3bb374a104faca742086988b3b35f | CC(C)(C)NS(=O)(=O)c1sccc1Br.CCOC(=O)CF>>CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CF | [Cl-].[NH4+].C(CCC)[Li].C(C)(C)(C)NS(=O)(=O)C=1SC=CC1Br.FCC(=O)OCC>>C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CF)=O | Br[c:13]1[c:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[s:10][cH:11][cH:12]1.CCO[C:14](=[O:15])[CH2:16][F:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][S:6](=[O:7])(=[O:8])[c:9]1[s:10][cH:11][cH:12][c:13]1[C:14](=[O:15])[CH2:16][F:17] | CC(C)(C)NS(=O)(=O)c1sccc1Br.CCOC(=O)CF | CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CF | null | null | O1CCCC1.C(C)OC(C)=O | C-C Coupling | Ester and halide to ketone | a481c55deb0c41b36324f6d8384d9d1038aa77d83e68121861f48e3679e7d04d | 7000e6fa6236297c1c515ebeaf5c7ba17704e006a4336e184f2503c0f1949baf | c1ccsc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1-[#16:6].C-C-O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[F;D1;H0:10]>>[#16:6]-[c:5]1:[#16;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[F;D1;H0:10] | 72 | [{"value": 72.0, "product": "C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CF)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | 2.98 g (0.0mole) of N-t-butyl-3-bromo-2-thiophenesulfonamide was dissolved in 50mi of dry tetrahydrofuran and the mixture was cooled to -78° C. under nitrogen gas. To the reaction solution was slowly added dropwise 8.4 ml of n-butyl lithium (2.5N) and then the temperature of the mixture was raised slowly to -20° C. and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ketone | c1ccsc1 | c1ccsc1 | c1ccsc1 | HBr | O1CCCC1.C(C)OC(C)=O | -78 | 0.166667 | CC(C)(C)NS(=O)(=O)c1sccc1Br.CCOC(=O)CF>O1CCCC1.C(C)OC(C)=O>CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CF |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-79a672ca3eff441b932b12489c10964b | CC(=O)OC(CF)c1ccsc1S(=O)(=O)NC(C)(C)C>>CC(=O)OC(CF)c1ccsc1S(N)(=O)=O | C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CF)OC(C)=O>>C(C)(=O)OC(CF)C1=C(SC=C1)S(=O)(=O)N | CC(C)(C)[NH:14][S:13]([c:12]1[c:8]([CH:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:6][F:7])[cH:9][cH:10][s:11]1)(=[O:15])=[O:16]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][F:7])[c:8]1[cH:9][cH:10][s:11][c:12]1[S:13]([NH2:14])(=[O:15])=[O:16] | CC(=O)OC(CF)c1ccsc1S(=O)(=O)NC(C)(C)C | CC(=O)OC(CF)c1ccsc1S(N)(=O)=O | null | null | FC(C(=O)O)(F)F | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1ccsc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]-[#16:2](-[NH2;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4] | 74 | [{"value": 74.0, "product": "C(C)(=O)OC(CF)C1=C(SC=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "C(C)(=O)OC(CF)C1=C(SC=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 1.4 g (0.0043 mole) of N-t-butyl-3-(1-aceoxy-2-fluoroethyl) -2-thiophenesulfonamide synthesized in Example 2 dissolved in 5 ml of trifluoroacetic acid. The reaction solution was stirred at normal temperature for 12 hours and then concentrated under reduced pressure. The residue was dissolved in methylene chloride and w... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccsc1 | Other | FC(C(=O)O)(F)F | null | 12 | CC(=O)OC(CF)c1ccsc1S(=O)(=O)NC(C)(C)C>FC(C(=O)O)(F)F>CC(=O)OC(CF)c1ccsc1S(N)(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9db8bda42ddd42569da026335543c4dd | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2sccc2C(CF)OC(C)=O)n1>>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2sccc2C(O)CF)n1 | COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C=1SC=CC1C(CF)OC(C)=O.Cl>>COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C=1SC=CC1C(CF)O | CC(=O)[O:23][CH:22]([c:21]1[c:17]([S:14]([NH:13][C:11]([NH:10][c:9]2[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:26]2)=[O:12])(=[O:15])=[O:16])[s:18][cH:19][cH:20]1)[CH2:24][F:25]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]2[s:18][cH:19][cH:2... | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2sccc2C(CF)OC(C)=O)n1 | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2sccc2C(O)CF)n1 | null | null | [OH-].[Na+] | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | O=C(Nc1ncccn1)NS(=O)(=O)c1cccs1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]-[C:2](-[C:3])-[OH;D1;+0:1] | 92 | [{"value": 92.0, "product": "COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C=1SC=CC1C(CF)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C=1SC=CC1C(CF)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 650 mg (0.0015 mole) of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide synthesized in Example 4 was dissolved in 5 ml of aqueous sodium hydroxide solution and then stirred at normal temperature for one hour. The reaction mixture was adjusted to pH4 by adding 5% aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1cncnc1.c1ccsc1 | HO- | [OH-].[Na+] | null | 1 | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2sccc2C(CF)OC(C)=O)n1>[OH-].[Na+]>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2sccc2C(O)CF)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5c044a04ef604d88b3d7ec14794c7e4f | CC(C)(C)NS(=O)(=O)c1sccc1Br.CCOC(C)=O.[Cl-]>>CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CCl | [Cl-].[NH4+].C(C)(C)(C)NS(=O)(=O)C=1SC=CC1Br.C(CCC)[Li].C(C)(=O)OCC>>C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)=O | Br[c:13]1[c:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[s:10][cH:11][cH:12]1.CCO[C:14](=[O:15])[CH3:16].[Cl-:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][S:6](=[O:7])(=[O:8])[c:9]1[s:10][cH:11][cH:12][c:13]1[C:14](=[O:15])[CH2:16][Cl:17] | CC(C)(C)NS(=O)(=O)c1sccc1Br.CCOC(C)=O.[Cl-] | CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CCl | null | null | null | C-C Coupling | OtherReaction | 994f613feb8d69c965236a0912f4ded4253ad1b80700d1fc60d11a6088329101 | b1c6261a734e53f4d91124624572b6ba9cd441d22cf9cb23410c5e92b65787c3 | c1ccsc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1-[#16:6].C-C-O-[C;H0;D3;+0:7](-[CH3;D1;+0:8])=[O;D1;H0:9].[Cl-;H0;D0:10]>>[#16:6]-[c:5]1:[#16;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D3;+0:7](=[O;D1;H0:9])-[CH2;D2;+0:8]-[Cl;H0;D1;+0:10] | 69 | [{"value": 69.0, "product": "C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | 2.98 g (0.0| mole) of N-t-butyl-3-bromo-2-thiophenesulfonamide was dissolved in 50 ml of dry tetrahydrofura mixture was cooled to -78° C. under nitrogen gas. To the reaction solution was slowly added dropwise 8.4 ml of n-butyl lithium(2.5N) and then the temperature of the mixture was raised slowly to -20° C. and again ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Primary halide.Ketone | c1ccsc1 | c1ccsc1 | c1ccsc1 | HBr | null | -78 | 0.166667 | CC(C)(C)NS(=O)(=O)c1sccc1Br.CCOC(C)=O.[Cl-]>>CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c101707cc7784ad6a6ce1b59640d7a42 | CC(=O)O.CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CCl>>CC(=O)OC(CCl)c1ccsc1S(=O)(=O)NC(C)(C)C | C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)=O.C(C)(=O)O.C(#N)[BH3-].[Na+]>>C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)OC(C)=O | [CH3:1][C:2](=[O:3])[OH:4].O=[C:5]([CH2:6][Cl:7])[c:8]1[cH:9][cH:10][s:11][c:12]1[S:13](=[O:14])(=[O:15])[NH:16][C:17]([CH3:18])([CH3:19])[CH3:20]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][Cl:7])[c:8]1[cH:9][cH:10][s:11][c:12]1[S:13](=[O:14])(=[O:15])[NH:16][C:17]([CH3:18])([CH3:19])[CH3:20] | CC(=O)O.CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CCl | CC(=O)OC(CCl)c1ccsc1S(=O)(=O)NC(C)(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | ce3fcb13cd756b3d5007891f978a84ff044dea1b4fc6d85c30cb98a72771d8c9 | 1e6b32c40735d9503c42bed07f902336208e3af52b7e21f1c270af60c351b6a9 | c1ccsc1 | O=[C;H0;D3;+0:1](-[C:2]-[Cl;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#16;a:7]:[c:8]:1-[#16:9].[C;D1;H3:10]-[C:11](=[O;D1;H0:12])-[OH;D1;+0:13]>>[#16:9]-[c:8]1:[#16;a:7]:[c:6]:[c:5]:[c:4]:1-[CH;D3;+0:1](-[C:2]-[Cl;D1;H0:3])-[O;H0;D2;+0:13]-[C:11](-[C;D1;H3:10])=[O;D1;H0:12] | 84 | [{"value": 84.0, "product": "C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1.5 g (0.005 mole) of N-t-butyl-3-(chloroacetyl)-2-thiophenesulfonamide synthesized in Example 6 was dissolved in the combined solution of 1 ml of acetic acid and 10 ml of tetrahydrofuran and then 0.31 g (0.005 mole) of sodium cyanoborohydride was added slowly thereto. The reaction solution was stirred at normal temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Ester | null | null | c1ccsc1 | Other | O1CCCC1 | null | 0.5 | CC(=O)O.CC(C)(C)NS(=O)(=O)c1sccc1C(=O)CCl>O1CCCC1>CC(=O)OC(CCl)c1ccsc1S(=O)(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f3db3635526422b993dd23dd01d5b7e | CC(=O)OC(CCl)c1ccsc1S(=O)(=O)NC(C)(C)C>>CC(=O)OC(CCl)c1ccsc1S(N)(=O)=O | C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)OC(C)=O>>C(C)(=O)OC(CCl)C1=C(SC=C1)S(=O)(=O)N | CC(C)(C)[NH:14][S:13]([c:12]1[c:8]([CH:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:6][Cl:7])[cH:9][cH:10][s:11]1)(=[O:15])=[O:16]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][Cl:7])[c:8]1[cH:9][cH:10][s:11][c:12]1[S:13]([NH2:14])(=[O:15])=[O:16] | CC(=O)OC(CCl)c1ccsc1S(=O)(=O)NC(C)(C)C | CC(=O)OC(CCl)c1ccsc1S(N)(=O)=O | null | null | FC(C(=O)O)(F)F | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1ccsc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]-[#16:2](-[NH2;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4] | 72 | [{"value": 72.0, "product": "C(C)(=O)OC(CCl)C1=C(SC=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.9, "product": "C(C)(=O)OC(CCl)C1=C(SC=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 1.5 g (0.0044 mole) of N-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide synthesized in Example 7 was dissolved in 5 ml of trifluoroacetic acid. The reaction solution was stirred at normal temperature for 12 hours and then concentrated under reduced pressure. The residue was dissolved in methylene chloride a... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccsc1 | Other | FC(C(=O)O)(F)F | null | 12 | CC(=O)OC(CCl)c1ccsc1S(=O)(=O)NC(C)(C)C>FC(C(=O)O)(F)F>CC(=O)OC(CCl)c1ccsc1S(N)(=O)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-340aa7277cd54868a6996a4b34326397 | Cc1cc(OCc2ccccc2)nc(S(C)(=O)=O)n1.O>>Cc1cc(OCc2ccccc2)nc(Oc2ccccc2)n1 | C(C1=CC=CC=C1)OC1=NC(=NC(=C1)C)S(=O)(=O)C.O>>C(C1=CC=CC=C1)OC1=NC(=NC(=C1)C)OC1=CC=CC=C1 | O=S(=O)([CH3:9])[c:14]1[n:13][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:20][cH:19][cH:18][cH:17]2)[cH:3][c:2]([CH3:1])[n:22]1.[OH2:15]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]([O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22]1 | Cc1cc(OCc2ccccc2)nc(S(C)(=O)=O)n1.O | Cc1cc(OCc2ccccc2)nc(Oc2ccccc2)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c689982e41cd1d37c1f084c2daae8093d19f2c277f9d78b556a3773c4e91063c | 219ffa44079bee6997e244f956e9a60496f0a5398aca07eea3c14372279af105 | c1ccc(COc2ccnc(Oc3ccccc3)n2)cc1 | O=S(=O)(-[CH3;D1;+0:1])-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]-[#8:5]-[C:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1):[#7;a:13]:[c:14].[OH2;D0;+0:15]>>[c:14]:[#7;a:13]:[c;H0;D3;+0:2](-[O;H0;D2;+0:15]-[c:16]1:[c:17]:[cH;D2;+0:11]:[c:10]:[c:9]:[cH;D2;+0:8]:1):[#7;a:3]:[c:4]-[#8:5]-[C:6]-[c;H0;D3;+0... | null | [] | null | null | null | null | 4-Benzyloxy-6-methyl-2-(methylsulfonyl)pyrimidine (Compound II-4) (0.45 g, 0.00162 mol) was added thereto and the resulting solution was allowed to react for about 2 hours at room temperature. The reaction solution was poured into water and extracted with ethyl acetate to separate an organic phase. The obtained organic... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Ether | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | null | null | null | null | Cc1cc(OCc2ccccc2)nc(S(C)(=O)=O)n1.O>>Cc1cc(OCc2ccccc2)nc(Oc2ccccc2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-28a790364d3a4b39a6924f5c3d8fb5d8 | CCOC(=O)C(CC)C(=O)OCC.N=C(N)c1ccccc1>>CCc1c(O)nc(-c2ccccc2)[nH]c1=O | O.Cl.C(C1=CC=CC=C1)(=N)N.C[O-].[Na+].C(C)C(C(=O)OCC)C(=O)OCC>>C(C)C=1C(NC(=NC1O)C1=CC=CC=C1)=O | CCO[C:4]([CH:3]([CH2:2][CH3:1])[C:15](OCC)=[O:16])=[O:5].[NH2:6][C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[NH:14]>>[CH3:1][CH2:2][c:3]1[c:4]([OH:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[nH:14][c:15]1=[O:16] | CCOC(=O)C(CC)C(=O)OCC.N=C(N)c1ccccc1 | CCc1c(O)nc(-c2ccccc2)[nH]c1=O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 553c150cdd7dbd0db0d6f297863528c29c608f3b73363412a40d575e164d9836 | b58423f9a2609746931edd2eb094cfdeeb7a95a2e60efda9d73e9e5239e8be6a | O=c1ccnc(-c2ccccc2)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-O-C-C.[NH2;D1;+0:8]-[C;H0;D3;+0:9](=[NH;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C;D1;H3:5]-[C:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:11](:[c:12]:[c:13... | 51 | [{"value": 51.0, "product": "C(C)C=1C(NC(=NC1O)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.9, "product": "C(C)C=1C(NC(=NC1O)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 45.19 g (0.29 mol) of benzamidine hydrochloride hydrate, 127.42 g (0.59 mol) of 25% sodium methoxide in methanol, 55 mL (0.29 mol) of diethyl ethylmalonate and 175 mL of methanol was heated at reflux for 25 h. The mixture was rotovapped to remove the bulk of the methanol. The residue was diluted with 300 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | CO | null | null | CCOC(=O)C(CC)C(=O)OCC.N=C(N)c1ccccc1>CO>CCc1c(O)nc(-c2ccccc2)[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b0378d7412b4bedb3ed0ed2242b2a38 | CCOC(=O)C=C(OCC)OCC.N=C(N)c1ccccc1>>CCOc1cc(=O)[nH]c(-c2ccccc2)n1 | O.Cl.C(C1=CC=CC=C1)(=N)N.C(C)(=O)[O-].[Na+].C(C)OC(=CC(=O)OCC)OCC.CS(=O)C>>C(C)OC1=CC(NC(=N1)C1=CC=CC=C1)=O | CCO[C:4]([O:3][CH2:2][CH3:1])=[CH:5][C:6](OCC)=[O:7].[NH2:8][C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[NH:16]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6](=[O:7])[nH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16]1 | CCOC(=O)C=C(OCC)OCC.N=C(N)c1ccccc1 | CCOc1cc(=O)[nH]c(-c2ccccc2)n1 | null | null | [OH-].[Na+] | Aromatic Heterocycle Formation | OtherReaction | d82f9c458402682e7644f99b62399f0511f124c6e3c1753a992ae84d9bea89bd | 82419e8808bf7ff4652f96c8cdfae6e968629b2d91d425ed75997b61827b36d9 | O=c1ccnc(-c2ccccc2)[nH]1 | C-C-O-[C;H0;D3;+0:1](-[#8:2]-[C:3])=[CH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C-C.[NH2;D1;+0:7]-[C;H0;D3;+0:8](=[NH;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:3]-[#8:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](=[O;D1;H0:6]):[nH;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]... | 57 | [{"value": 57.0, "product": "C(C)OC1=CC(NC(=N1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "C(C)OC1=CC(NC(=N1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 3.14 g (20.0 mmol) of benzamidine hydrochloride hydrate, 1.65 g (20.1 mmol) of powdered anhydrous sodium acetate, 4.17 g (22.2 mmol) of ethyl 3,3-diethoxyacrylate and 10 mL of DMSO was heated at 120° C. for 8 h. The mixture was cooled, diluted with 50 mL of 5% aqueous NaOH and washed with two 100 mL portio... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Primary amine | Ether | null | c1ccncn1 | c1ccncn1.c1ccccc1 | HO- | [OH-].[Na+] | 120 | null | CCOC(=O)C=C(OCC)OCC.N=C(N)c1ccccc1>[OH-].[Na+]>CCOc1cc(=O)[nH]c(-c2ccccc2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b051943e828a4e248c90cd25b0c51782 | CCc1c(Br)nc(-c2ccccc2)nc1Br.O=S(=O)(O)O>>CCc1c(Br)nc(-c2ccccc2)[nH]c1=O | S(O)(O)(=O)=O.BrC1=NC(=NC(=C1CC)Br)C1=CC=CC=C1>>BrC1=C(C(NC(=N1)C1=CC=CC=C1)=O)CC | Br[c:15]1[c:3]([CH2:2][CH3:1])[c:4]([Br:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14]1.O=S(=O)(O)[OH:16]>>[CH3:1][CH2:2][c:3]1[c:4]([Br:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[nH:14][c:15]1=[O:16] | CCc1c(Br)nc(-c2ccccc2)nc1Br.O=S(=O)(O)O | CCc1c(Br)nc(-c2ccccc2)[nH]c1=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 42c44ba822f4055de2d24d5b39b754d7dda39adf52a0688a4a8eae47fd02626c | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | O=c1ccnc(-c2ccccc2)[nH]1 | Br-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Br;D1;H0:7]):[c:8]:1-[C:9].O-S(=O)(=O)-[OH;D1;+0:10]>>[Br;D1;H0:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[nH;D2;+0:2]:[c;H0;D3;+0:1](=[O;H0;D1;+0:10]):[c:8]:1-[C:9] | 99 | [{"value": 99.0, "product": "BrC1=C(C(NC(=N1)C1=CC=CC=C1)=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To 8.29 g (26.1 mmol) of crude 4,6-dibromo-5-ethyl-2-phenylpyrimidine was added a mixture of 4 mL of water and 15 mL of concentrated sulfuric acid. The mixture was stirred for 18 h and poured onto 200 g of crushed ice. After the ice had melted the precipitate was collected by filtration and dried under vacuum to afford... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HBr | O | null | 18 | CCc1c(Br)nc(-c2ccccc2)nc1Br.O=S(=O)(O)O>O>CCc1c(Br)nc(-c2ccccc2)[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2d447b7bc2ec4665ad48ac9de0170d06 | O=C1CCC(=O)N1Br.O=c1cc(C(F)(F)F)nc(-c2ccccc2)[nH]1>>O=c1[nH]c(-c2ccccc2)nc(C(F)(F)F)c1Br | C1(=CC=CC=C1)C1=NC(=CC(N1)=O)C(F)(F)F.BrN1C(CCC1=O)=O>>BrC=1C(NC(=NC1C(F)(F)F)C1=CC=CC=C1)=O | O=C1CCC(=O)N1[Br:18].[O:1]=[c:2]1[nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>>[O:1]=[c:2]1[nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]1[Br:18] | O=C1CCC(=O)N1Br.O=c1cc(C(F)(F)F)nc(-c2ccccc2)[nH]1 | O=c1[nH]c(-c2ccccc2)nc(C(F)(F)F)c1Br | null | null | CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C | Functional Group Interconversion | Bromination | c1f267498588fdc78d70fa059a48254fc6fd3441a5bb656fda4935ce99f2babe | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1ccnc(-c2ccccc2)[nH]1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10](=[O;D1;H0:11]):[cH;D2;+0:12]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:12]1:[c:6](-[C:3](-[F;D1;H0:2])(-[F;D1;H0:4])-[F;D1;H0:5]):[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1=[O;D1;H0:11] | 83.5 | [{"value": 83.5, "product": "BrC=1C(NC(=NC1C(F)(F)F)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.5, "product": "BrC=1C(NC(=NC1C(F)(F)F)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 1.0 g (3.94 mmol) of 2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone and 20 mL of glacial acetic add was added 1.0 g (5.6 mmol) N-bromosuccinimide and the mixture was left to stir at room temperature for 16 h. The reaction was poured onto ice water and vacuum filtered, washing well with water. The crude ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccncn1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C | null | 16 | O=C1CCC(=O)N1Br.O=c1cc(C(F)(F)F)nc(-c2ccccc2)[nH]1>CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C>O=c1[nH]c(-c2ccccc2)nc(C(F)(F)F)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f05000905bc748e98487d679b80f953b | O=C1CCC(=O)N1Br.O=c1cc(-c2ccccc2)nc(-c2ccccc2)[nH]1>>O=c1[nH]c(-c2ccccc2)nc(-c2ccccc2)c1Br | C1(=CC=CC=C1)C1=NC(=CC(N1)=O)C1=CC=CC=C1.BrN1C(CCC1=O)=O>>BrC=1C(NC(=NC1C1=CC=CC=C1)C1=CC=CC=C1)=O | O=C1CCC(=O)N1[Br:20].[O:1]=[c:2]1[nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1>>[O:1]=[c:2]1[nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]1[Br:20] | O=C1CCC(=O)N1Br.O=c1cc(-c2ccccc2)nc(-c2ccccc2)[nH]1 | O=c1[nH]c(-c2ccccc2)nc(-c2ccccc2)c1Br | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | c1f267498588fdc78d70fa059a48254fc6fd3441a5bb656fda4935ce99f2babe | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1cc(-c2ccccc2)nc(-c2ccccc2)[nH]1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[O;D1;H0:2]=[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:7](-[c:8]):[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:1=[O;D1;H0:2] | 48.3 | [{"value": 48.0, "product": "BrC=1C(NC(=NC1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.3, "product": "BrC=1C(NC(=NC1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | To a suspension of 13.37 g (56 mmol) of 2,6-diphenyl-4(3H)-pyrimidinone and 200 mL glacial acetic acid was added 15.1 g (84.8 mmol) of N-bromosuccinimide and the mixture was left to stir at room temperature for 60 h. The reaction was poured onto 100 g crushed ice and vacuum filtered, washing well with water, then air d... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccncn1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O | null | 60 | O=C1CCC(=O)N1Br.O=c1cc(-c2ccccc2)nc(-c2ccccc2)[nH]1>C(C)(=O)O>O=c1[nH]c(-c2ccccc2)nc(-c2ccccc2)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-be4d8163d3b146d0a463a6fc363aaeaa | CCc1cc(=O)[nH]c(-c2ccccc2)n1.II>>CCc1nc(-c2ccccc2)[nH]c(=O)c1I | C(C)C1=CC(NC(=N1)C1=CC=CC=C1)=O.[OH-].[Na+].II>>C(C)C1=C(C(NC(=N1)C1=CC=CC=C1)=O)I | [CH3:1][CH2:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][c:13](=[O:14])[cH:15]1.I[I:16]>>[CH3:1][CH2:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][c:13](=[O:14])[c:15]1[I:16] | CCc1cc(=O)[nH]c(-c2ccccc2)n1.II | CCc1nc(-c2ccccc2)[nH]c(=O)c1I | null | null | O | Functional Group Interconversion | OtherReaction | ab990d4cf4e29f4bfc1eed19f85a157586116cba28cf7e047e67e704b97886a0 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1ccnc(-c2ccccc2)[nH]1 | I-[I;H0;D1;+0:1].[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](=[O;D1;H0:8]):[cH;D2;+0:9]:1>>[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](=[O;D1;H0:8]):[c;H0;D3;+0:9]:1-[I;H0;D1;+0:1] | 94.5 | [{"value": 75.0, "product": "C(C)C1=C(C(NC(=N1)C1=CC=CC=C1)=O)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "C(C)C1=C(C(NC(=N1)C1=CC=CC=C1)=O)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 8.18 g (40.9 mmol) of 6-ethyl-2-phenyl-4(3H)-pyrimidinone, 1.68 g (42.0 mmol) of sodium hydroxide, 10.42 g (41.0 mmol) of iodine and 50 mL of water was heated at 50° C. for 4 h. The mixture was cooled and filtered. The white solid collected was dried in a vacuum oven to leave 12.60 g (75%) of 6-ethyl-5-iod... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncn1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HI | O | 50 | null | CCc1cc(=O)[nH]c(-c2ccccc2)n1.II>O>CCc1nc(-c2ccccc2)[nH]c(=O)c1I |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-475d4575be964743a02cc9754560986f | CCc1cc(=O)[nH]c(-c2ccccc2)n1.O=C1CCC(=O)N1Cl>>CCc1nc(-c2ccccc2)[nH]c(=O)c1Cl | C(C)C1=CC(NC(=N1)C1=CC=CC=C1)=O.ClN1C(CCC1=O)=O>>ClC=1C(NC(=NC1CC)C1=CC=CC=C1)=O | [CH3:1][CH2:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][c:13](=[O:14])[cH:15]1.O=C1CCC(=O)N1[Cl:16]>>[CH3:1][CH2:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][c:13](=[O:14])[c:15]1[Cl:16] | CCc1cc(=O)[nH]c(-c2ccccc2)n1.O=C1CCC(=O)N1Cl | CCc1nc(-c2ccccc2)[nH]c(=O)c1Cl | null | null | C(C)(=O)O | Functional Group Interconversion | Chlorination | c1f267498588fdc78d70fa059a48254fc6fd3441a5bb656fda4935ce99f2babe | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1ccnc(-c2ccccc2)[nH]1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](=[O;D1;H0:8]):[cH;D2;+0:9]:1>>[C:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](=[O;D1;H0:8]):[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:1] | 87.1 | [{"value": 87.1, "product": "ClC=1C(NC(=NC1CC)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 7.81 g (39.1 mmol) of 6-ethyl-2-phenyl-4(3H)-pyrimidinone and 5.80 g (43.4 mmol) of N-chlorosuccinimide in 100 mL of glacial acetic acid was heated at 90° C. for 4 h. The mixture was cooled, poured onto crushed ice and allowed to stand until the ice had melted. The mixture was filtered and the sol... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccncn1.C1CCNC1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)(=O)O | null | null | CCc1cc(=O)[nH]c(-c2ccccc2)n1.O=C1CCC(=O)N1Cl>C(C)(=O)O>CCc1nc(-c2ccccc2)[nH]c(=O)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d6194f9ae43e4fbd94964245b6b3d3e4 | O=c1[nH]c(-c2ccccc2)nc(Oc2ccccc2)c1I>>O=c1cc(Oc2ccccc2)nc(-c2ccccc2)[nH]1 | IC=1C(NC(=NC1OC1=CC=CC=C1)C1=CC=CC=C1)=O>>O(C1=CC=CC=C1)C1=CC(NC(=N1)C1=CC=CC=C1)=O | I[c:3]1[c:2](=[O:1])[nH:20][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:12][c:4]1[O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[nH:20]1 | O=c1[nH]c(-c2ccccc2)nc(Oc2ccccc2)c1I | O=c1cc(Oc2ccccc2)nc(-c2ccccc2)[nH]1 | null | [Zn].[Zn].[Zn] | C(C)(=O)O | Functional Group Interconversion | Aromatic dehalogenation | 895159d874869aa7a3c29ba9f3a6fce27d4e3f1b326a7f3ea2a46c97ca88bc67 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=c1cc(Oc2ccccc2)nc(-c2ccccc2)[nH]1 | I-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[#8:8]>>[#8:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:2](=[O;D1;H0:3]):[cH;D2;+0:1]:1 | 125.6 | [{"value": 57.0, "product": "O(C1=CC=CC=C1)C1=CC(NC(=N1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 125.6, "product": "O(C1=CC=CC=C1)C1=CC(NC(=N1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7.07 g (18.1 mmol) of crude 5-iodo-6-phenoxy-2-phenyl-4(3H)-pyrimidinone, 2.02 g (31.1 mmol) of zinc dust and 25 mL of glacial acetic acid was heated to reflux. After 15 min an additional 2.06 g (31.7 mmol) of zinc dust was added, followed 15 min later by a further 2.04 g (31.4 mmol) of zinc dust. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1 | c1ccncn1 | c1ccncn1.c1ccccc1.c1ccccc1 | I- | [Zn].[Zn].[Zn].C(C)(=O)O | null | null | O=c1[nH]c(-c2ccccc2)nc(Oc2ccccc2)c1I>[Zn].[Zn].[Zn].C(C)(=O)O>O=c1cc(Oc2ccccc2)nc(-c2ccccc2)[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c70bc697c73a4481b3467e71a66893b5 | C#CCn1c(-c2ccccc2)nc(C(=O)OCC)c(C)c1=O>>C#CCn1c(-c2ccccc2)nc(C(=O)O)c(C)c1=O | C(C)OC(=O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C.[OH-].[Na+]>>C(=O)(O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C | CC[O:16][C:14]([c:13]1[n:12][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:4]([CH2:3][C:2]#[CH:1])[c:19](=[O:20])[c:17]1[CH3:18])=[O:15]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([C:14](=[O:15])[OH:16])[c:17]([CH3:18])[c:19]1=[O:20] | C#CCn1c(-c2ccccc2)nc(C(=O)OCC)c(C)c1=O | C#CCn1c(-c2ccccc2)nc(C(=O)O)c(C)c1=O | null | null | C(C)O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccnc(-c2ccccc2)[nH]1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 53.2 | [{"value": 53.0, "product": "C(=O)(O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "C(=O)(O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 1.81 g (6.1 mmol) of 6-ethoxycarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 100 mL of ethanol and 50 mL of THF was added 50 mL of 5% aqueous sodium hydroxide. The mixture was stirred at room temperature for 24 h and rotovapped to remove the bulk of the organic solvents. The residue was di... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | C(C)O.C1CCOC1 | null | 24 | C#CCn1c(-c2ccccc2)nc(C(=O)OCC)c(C)c1=O>C(C)O.C1CCOC1>C#CCn1c(-c2ccccc2)nc(C(=O)O)c(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-21393e26ab0b4c64a67d4dbe4b4c6328 | C#CCn1c(-c2ccccc2)nc(C(=O)O)c(C)c1=O.CNC>>C#CCn1c(-c2ccccc2)nc(C(=O)N(C)C)c(C)c1=O | C(=O)(O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C.Cl.CNC.N1=CC=CC=C1.C1(CCCCC1)N=C=NC1CCCCC1>>CN(C(=O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C)C | O[C:14]([c:13]1[n:12][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:4]([CH2:3][C:2]#[CH:1])[c:21](=[O:22])[c:19]1[CH3:20])=[O:15].[NH:16]([CH3:17])[CH3:18]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([C:14](=[O:15])[N:16]([CH3:17])[CH3:18])[c:19]([CH3:20])[c:21]1=[O:22] | C#CCn1c(-c2ccccc2)nc(C(=O)O)c(C)c1=O.CNC | C#CCn1c(-c2ccccc2)nc(C(=O)N(C)C)c(C)c1=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=c1ccnc(-c2ccccc2)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 32 | [{"value": 32.0, "product": "CN(C(=O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.7, "product": "CN(C(=O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To a stirred solution of 0.87 g (3.2 mmol) of crude 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone, 0.32 g (3.9 mmol) of dimethylamine hydrochloride and 2 mL of pyridine in 10 mL of THF was added 0.74 g (3.6 mmol) of solid N,N'-dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 4 days... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1cncnc1.c1ccccc1 | HO- | C1CCOC1 | null | 96 | C#CCn1c(-c2ccccc2)nc(C(=O)O)c(C)c1=O.CNC>C1CCOC1>C#CCn1c(-c2ccccc2)nc(C(=O)N(C)C)c(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c771bb9653f84a339085fb2d456f388e | C#CCn1c(-c2ccccc2)nc(Cl)c(C)c1=O.CNC>>C#CCn1c(-c2ccccc2)nc(N(C)C)c(C)c1=O | ClC1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C.CNC>>CN(C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C)C | Cl[c:13]1[n:12][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:4]([CH2:3][C:2]#[CH:1])[c:19](=[O:20])[c:17]1[CH3:18].[NH:14]([CH3:15])[CH3:16]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([N:14]([CH3:15])[CH3:16])[c:17]([CH3:18])[c:19]1=[O:20] | C#CCn1c(-c2ccccc2)nc(Cl)c(C)c1=O.CNC | C#CCn1c(-c2ccccc2)nc(N(C)C)c(C)c1=O | null | null | CCOCC.O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccnc(-c2ccccc2)[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4](-[C:5]-[C:6]#[C;D1;H1:7]):[c:8](=[O;D1;H0:9]):[c:10]:1-[C;D1;H3:11].[C;D1;H3:12]-[NH;D2;+0:13]-[C;D1;H3:14]>>[C;D1;H1:7]#[C:6]-[C:5]-[#7;a:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13](-[C;D1;H3:12])-[C;D1;H3:14]):[c:10](-[C;D1;H3:11]):[c:8]:1=[O;D1;H0:9] | null | [] | null | null | null | null | To an ice cooled solution of 1.5 g (3.8 mmol) 6-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 4 mL of tetrahydrofuran, was added 22 mL (99 mmol) of 4.5M dimethylamine in ether portionwise (2-4 mL) over a period of 7 days. The reaction mixture was allowed to warm and stir at room temperature after each addi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | CCOCC.O1CCCC1 | null | null | C#CCn1c(-c2ccccc2)nc(Cl)c(C)c1=O.CNC>CCOCC.O1CCCC1>C#CCn1c(-c2ccccc2)nc(N(C)C)c(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1591768695574e68b20ca645245f4562 | C#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O.[OH-]>>CCc1c(C(F)(F)F)nc(-c2ccccc2)n(CC(C)=O)c1=O | C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#C)=O.C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#C)=O.[OH-].[Na+]>>C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC(C)=O)=O | [CH3:1][CH2:2][c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17]([CH2:18][C:19]#[CH:20])[c:22]1=[O:23].[OH-:21]>>[CH3:1][CH2:2][c:3]1[c:4]([C:5]([F:6])([F:7])[F:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17]([CH2:18][C:19]([CH3:20])=[O:21])[c:22]1=[O... | C#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O.[OH-] | CCc1c(C(F)(F)F)nc(-c2ccccc2)n(CC(C)=O)c1=O | null | null | C1CCOC1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 40bc86c3933af1a903f8329b3ea43014fcb4fcf95be97cdb9c41053869e91cb5 | 7f2cd7881a1a7accd4c4687f629eb04c8f2612869365019cb1ad442e2c2b003b | O=c1ccnc(-c2ccccc2)[nH]1 | [#7;a:1]:[c:2]:[#7;a:3]-[C:4]-[C;H0;D2;+0:5]#[CH;D1;+0:6].[OH-;D0:7]>>[#7;a:1]:[c:2]:[#7;a:3]-[C:4]-[C;H0;D3;+0:5](-[CH3;D1;+0:6])=[O;H0;D1;+0:7] | null | [] | null | null | null | null | To a stirred solution of 4.83 g (15.8 mmol) of 5-ethyl-3-propargyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (compound 46) in 50 mL of THF was added 50 mL of 10% aq NaOH. The mixture was heated at reflux for 2 h, cooled and diluted with 150 mL of ethyl acetate. The organic layer was separated, washed with 50 mL of ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Ketone | null | null | c1cncnc1.c1ccccc1 | null | C1CCOC1.C(C)(=O)OCC | null | null | C#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O.[OH-]>C1CCOC1.C(C)(=O)OCC>CCc1c(C(F)(F)F)nc(-c2ccccc2)n(CC(C)=O)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a76bfee244c4e589316dfef7559347f | COCOC.O=c1cc(C(F)(F)F)nc(-c2ccccc2)[nH]1>>COCn1c(-c2ccccc2)nc(C(F)(F)F)cc1=O | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.C1(=CC=CC=C1)C1=NC(=CC(N1)=O)C(F)(F)F.COCOC.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.[OH-].[Na+]>>COCN1C(=NC(=CC1=O)C(F)(F)F)C1=CC=CC=C1 | CO[CH2:3][O:2][CH3:1].[nH:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1=[O:20]>>[CH3:1][O:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1=[O:20] | COCOC.O=c1cc(C(F)(F)F)nc(-c2ccccc2)[nH]1 | COCn1c(-c2ccccc2)nc(C(F)(F)F)cc1=O | null | null | C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 0add32a5be4fe5174086acead6feb976d1a076dc7d68959972c5cd4b3c28c84c | ccc058ecd89f692c39a92bd6db91fb86578428d38b5955a659e0a2343eccf0fd | O=c1ccnc(-c2ccccc2)[nH]1 | C-O-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[O;D1;H0:4]=[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9](-[c:10]):[nH;D2;+0:11]:1>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:5](=[O;D1;H0:4]):[c:6]:[c:7]:[#7;a:8]:[c:9]:1-[c:10] | 32.8 | [{"value": 32.0, "product": "COCN1C(=NC(=CC1=O)C(F)(F)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "COCN1C(=NC(=CC1=O)C(F)(F)F)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 1.5 g (5.9 mmol) of 2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone, 17.2 g (226.3 mmol) dimethoxymethane, and 35 mL of chloroform was added 2.5 g (17.6 mmol) phosphorous pentoxide, at room temperature. By TLC (25% ethyl acetate in hexane) the reaction was incomplete after 4 h and an additional 3 g (21.1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ether | c1ccncn1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl.C(C)(=O)OCC | null | 16 | COCOC.O=c1cc(C(F)(F)F)nc(-c2ccccc2)[nH]1>C(Cl)(Cl)Cl.CCCCCC.C(Cl)Cl.C(C)(=O)OCC>COCn1c(-c2ccccc2)nc(C(F)(F)F)cc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cbd7be36ef084343a7a9b531a9094d81 | C#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O.C=CI>>C=CC#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O | C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#C)=O.C(=C)I>>C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#CC=C)=O | [CH:3]#[C:4][CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20]([CH2:21][CH3:22])[c:23]1=[O:24].I[CH:2]=[CH2:1]>>[CH2:1]=[CH:2][C:3]#[C:4][CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20]([CH2:21][CH3... | C#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O.C=CI | C=CC#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O | null | [Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_alkenyl halide | b0275c92ec48c41d276310eb23d2d5949a66cffe648b8115d867fbb00a93be00 | 6ee7e5b969047b3680750ebc6d5ad3b212c3653eb4f65f81d3cb77b36ae2893f | O=c1ccnc(-c2ccccc2)[nH]1 | I-[CH;D2;+0:1]=[C;D1;H2:2].[C:3]-[C:4]#[CH;D1;+0:5]>>[C:3]-[C:4]#[C;H0;D2;+0:5]-[CH;D2;+0:1]=[C;D1;H2:2] | 28.4 | [{"value": 28.4, "product": "C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#CC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | To a deoxygenated solution of 1.01 g (3.28 mmol) of 5-ethyl-2-phenyl-3-propargyl-6-trifluoromethyl-4(3H)-pyrimidinone and 0.61 g (3.96 mmol) of vinyl iodide in 25 mL of triethylamine was added a mixture of 60 mg of copper (I) iodide and 60 mg of bis(triphenylphosphine) palladium (II) chloride. The mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Vinyl | Alkyne.Vinyl | null | null | c1cncnc1.c1ccccc1 | HI | [Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC | null | 22 | C#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O.C=CI>[Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>C=CC#CCn1c(-c2ccccc2)nc(C(F)(F)F)c(CC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-febb9432bc444d1b8660781f308ba31e | C#CCn1c(-c2cccc(C3OCCO3)c2)nc(CC)c(CC)c1=O>>C#CCn1c(-c2cccc(C=O)c2)nc(CC)c(CC)c1=O | CCOCC.O.C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C1OCCO1)CC#C)=O.Cl>>C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C=O)CC#C)=O | C1C[O:12][CH:11]([c:10]2[cH:9][cH:8][cH:7][c:6](-[c:5]3[n:4]([CH2:3][C:2]#[CH:1])[c:21](=[O:22])[c:18]([CH2:19][CH3:20])[c:15]([CH2:16][CH3:17])[n:14]3)[cH:13]2)O1>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13]2)[n:14][c:15]([CH2:16][CH3:17])[c:18]([CH2:19][CH3:20])[c:21]1=[O:22] | C#CCn1c(-c2cccc(C3OCCO3)c2)nc(CC)c(CC)c1=O | C#CCn1c(-c2cccc(C=O)c2)nc(CC)c(CC)c1=O | null | null | CCCCCC.C(C)(=O)OCC | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=c1ccnc(-c2ccccc2)[nH]1 | [c:1]:[c:2](-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1):[c:5]>>[O;H0;D1;+0:4]=[CH;D2;+0:3]-[c:2](:[c:1]):[c:5] | 86.4 | [{"value": 86.0, "product": "C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C=O)CC#C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C=O)CC#C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 2.3 g (6.8 mmol) of 5,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone in 1 mL of ethyl acetate was added 50 mL of 6M hydrochloric acid and the mixture was stirred for 4 hours. The reaction was followed by gas chromatography and TLC(20% ethyl acetate in hexane). Upon completion of re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1cncnc1.c1ccccc1 | HO- | CCCCCC.C(C)(=O)OCC | null | 4 | C#CCn1c(-c2cccc(C3OCCO3)c2)nc(CC)c(CC)c1=O>CCCCCC.C(C)(=O)OCC>C#CCn1c(-c2cccc(C=O)c2)nc(CC)c(CC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d84c8f338a741eebe88ed5f50eec903 | CCc1nc(-c2ccccc2)n(CC)c(=O)c1I.O=C([O-])C(F)(F)F>>CCc1nc(-c2ccccc2)n(CC)c(=O)c1C(F)(F)F | C(C)N1C(=NC(=C(C1=O)I)CC)C1=CC=CC=C1.FC(C(=O)[O-])(F)F.[Na+].CN1C(CCC1)=O>>C(C)N1C(=NC(=C(C1=O)C(F)(F)F)CC)C1=CC=CC=C1 | I[c:17]1[c:3]([CH2:2][CH3:1])[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]([CH2:13][CH3:14])[c:15]1=[O:16].O=C([O-])[C:18]([F:19])([F:20])[F:21]>>[CH3:1][CH2:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]([CH2:13][CH3:14])[c:15](=[O:16])[c:17]1[C:18]([F:19])([F:20])[F:21] | CCc1nc(-c2ccccc2)n(CC)c(=O)c1I.O=C([O-])C(F)(F)F | CCc1nc(-c2ccccc2)n(CC)c(=O)c1C(F)(F)F | null | [Cu]I | CCOCC | C-C Coupling | OtherReaction | 47cbd2b0ff20300536d0cffca6c2ea55a53280e27fccd5cfa965ded0f6858b07 | e720556849b4b6d74d42c92419c2568e82bddeb43f0960aee719e65329267335 | O=c1ccnc(-c2ccccc2)[nH]1 | I-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:1-[C:9].O=C(-[O-])-[C;H0;D4;+0:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]>>[C:5]-[#7;a:4]1:[c:6]:[#7;a:7]:[c:8](-[C:9]):[c;H0;D3;+0:1](-[C;H0;D4;+0:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:2]:1=[O;D1;H0:3] | 42.2 | [{"value": 42.2, "product": "C(C)N1C(=NC(=C(C1=O)C(F)(F)F)CC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.00 g (2.8 mmol) of 3,6-diethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone, 1.08 g (5.7 mmol) of copper (I) iodide, 1.54 g (11.3 mmol) of sodium trifluoroacetate and 8 mL of anhydrous N-methylpyrrolidinone was heated at 175 C for 2 h. The mixture was cooled, diluted with 175 mL of ether, washed with four 50 mL po... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide | Trifluoro group | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | I- | [Cu]I.CCOCC | null | null | CCc1nc(-c2ccccc2)n(CC)c(=O)c1I.O=C([O-])C(F)(F)F>[Cu]I.CCOCC>CCc1nc(-c2ccccc2)n(CC)c(=O)c1C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db525fc7ca504fc7b7efbfba048e0449 | C#CCn1c(-c2cccc(C=O)c2)nc(CC)c(CC)c1=O.NO>>C#CCn1c(C2=CC=CC(=NO)C2)nc(CC)c(CC)c1=O | C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C=O)CC#C)=O.Cl.NO>>C(C)C=1C(N(C(=NC1CC)C=1CC(C=CC1)=NO)CC#C)=O | O=C[c:10]1[cH:9][cH:8][cH:7][c:6](-[c:5]2[n:4]([CH2:3][C:2]#[CH:1])[c:21](=[O:22])[c:18]([CH2:19][CH3:20])[c:15]([CH2:16][CH3:17])[n:14]2)[cH:13]1.[NH2:11][OH:12]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5]([C:6]2=[CH:7][CH:8]=[CH:9][C:10](=[N:11][OH:12])[CH2:13]2)[n:14][c:15]([CH2:16][CH3:17])[c:18]([CH2:19][CH3:20])[c:21]1=[O:22... | C#CCn1c(-c2cccc(C=O)c2)nc(CC)c(CC)c1=O.NO | C#CCn1c(C2=CC=CC(=NO)C2)nc(CC)c(CC)c1=O | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 15e2b91d223429254e0537e29a607acdcc37e5fd3dd4313d80c7521c1966cdc2 | b81c903f6c555f71b81105429c919c51c8d3cea1128467d023295f77c1491add | N=C1C=CC=C(c2nccc(=O)[nH]2)C1 | O=C-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4](:[#7;a:5]:[c:6]):[#7;a:7](-[C:8]-[C:9]#[C;D1;H1:10]):[c:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:1.[NH2;D1;+0:15]-[O;D1;H1:16]>>[C;D1;H1:10]#[C:9]-[C:8]-[#7;a:7](:[c:11]):[c;H0;D3;+0:4](-[C;H0;D3;+0:3]1=[CH;D2;+0:12]-[CH;D2;+0:13]=[CH;D2;+0:14]-[C;H0... | 77.6 | [{"value": 77.6, "product": "C(C)C=1C(N(C(=NC1CC)C=1CC(C=CC1)=NO)CC#C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.9, "product": "C(C)C=1C(N(C(=NC1CC)C=1CC(C=CC1)=NO)CC#C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 100 mL RBF were charged 1.1 g (3.7 mmol) of 5,6-diethyl-2-(3-formyl-phenyl)-3-propargyl-4(3H)-pyrimidinone, 0.52 g (7.5 mmol) of hydroxylamine hydrochloride and 50 mL of ethanol. The reaction mixture was refluxed for 17 hours. The ethanol was removed in vacuo and ether and ethyl acetate were added to the residue. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Conjugated diene.Oxime | c1ccccc1 | C1=CCCC=C1 | c1cncnc1.C1=CCCC=C1 | HO- | C(C)O | null | null | C#CCn1c(-c2cccc(C=O)c2)nc(CC)c(CC)c1=O.NO>C(C)O>C#CCn1c(C2=CC=CC(=NO)C2)nc(CC)c(CC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d39e19c8619b4440b84b2d542c14fa6e | C#CCn1c(-c2ccccc2)nc(CC)c(CC(=O)OC)c1=O>>C#CCn1c(-c2ccccc2)nc(CC)c(CCO)c1=O | O.C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC(=O)OC.C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC(=O)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CCO | CO[C:18]([CH2:17][c:16]1[c:13]([CH2:14][CH3:15])[n:12][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:4]([CH2:3][C:2]#[CH:1])[c:20]1=[O:21])=[O:19]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([CH2:14][CH3:15])[c:16]([CH2:17][CH2:18][OH:19])[c:20]1=[O:21] | C#CCn1c(-c2ccccc2)nc(CC)c(CC(=O)OC)c1=O | C#CCn1c(-c2ccccc2)nc(CC)c(CCO)c1=O | null | null | CCOCC.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=c1ccnc(-c2ccccc2)[nH]1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4](:[c:5]:[#7;a:6]):[c:7]:[#7;a:8]>>[#7;a:6]:[c:5]:[c:4](-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:7]:[#7;a:8] | null | [] | null | null | 3 | HOUR | A stirred solution of 1.35 g (4.4 mmol) of 6-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 105) in 30 mL of THF was cooled in an ice bath and a slurry of 0.10 g (2.6 mmol) of lithium aluminum hydride in 10 mL of ether was added. The ice bath was allowed to melt and the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cncnc1.c1ccccc1 | Other | CCOCC.C1CCOC1 | null | 3 | C#CCn1c(-c2ccccc2)nc(CC)c(CC(=O)OC)c1=O>CCOCC.C1CCOC1>C#CCn1c(-c2ccccc2)nc(CC)c(CCO)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f44bdc8cc42c4333808efcfd30ed387a | C#CCn1c(-c2ccccc2)nc(CC)c(CC(=O)OC)c1=O.[NH4+]>>C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O | C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC(=O)OC.C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC(=O)OC.[NH4+].[OH-]>>NC(=O)CC=1C(N(C(=NC1CC)C1=CC=CC=C1)CC#C)=O | CO[C:18]([CH2:17][c:16]1[c:13]([CH2:14][CH3:15])[n:12][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:4]([CH2:3][C:2]#[CH:1])[c:21]1=[O:22])=[O:20].[NH4+:19]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([CH2:14][CH3:15])[c:16]([CH2:17][C:18]([NH2:19])=[O:20])[c:21]1=[O:22] | C#CCn1c(-c2ccccc2)nc(CC)c(CC(=O)OC)c1=O.[NH4+] | C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O | null | null | C1CCOC1 | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=c1ccnc(-c2ccccc2)[nH]1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4](:[c:5]:[#7;a:6]):[c:7]:[#7;a:8].[NH4+;D0:9]>>[#7;a:6]:[c:5]:[c:4](-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:9])=[O;D1;H0:2]):[c:7]:[#7;a:8] | null | [] | null | null | null | null | To a stirred solution of 1.75 g (5.7 mmol) of 6-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 105) in 100 mL of THF was added 200 mL of concentrated aqueous NH4OH. The mixture was stirred for 2 weeks and the bulk of the THF was removed on the rotovap. The mixture was shaken with 100 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1cncnc1.c1ccccc1 | HO- | C1CCOC1 | null | null | C#CCn1c(-c2ccccc2)nc(CC)c(CC(=O)OC)c1=O.[NH4+]>C1CCOC1>C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-504c94f80cd14c1f86ab5786e3c9e054 | C#CCn1c(-c2ccccc2)nc(CC)c(OC)c1=O>>C#CCn1c(-c2ccccc2)nc(CC)c(O)c1=O | C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)OC.C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)OC>>C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)O | C[O:17][c:16]1[c:13]([CH2:14][CH3:15])[n:12][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:4]([CH2:3][C:2]#[CH:1])[c:18]1=[O:19]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]([CH2:14][CH3:15])[c:16]([OH:17])[c:18]1=[O:19] | C#CCn1c(-c2ccccc2)nc(CC)c(OC)c1=O | C#CCn1c(-c2ccccc2)nc(CC)c(O)c1=O | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccnc(-c2ccccc2)[nH]1 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3](-[C:4]):[#7;a:5]:[c:6]:[#7;a:7](-[C:8]-[C:9]#[C;D1;H1:10]):[c:11]:1=[O;D1;H0:12]>>[C:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]-[C:9]#[C;D1;H1:10]):[c:11](=[O;D1;H0:12]):[c:2]:1-[OH;D1;+0:1] | 72 | [{"value": 72.0, "product": "C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To an oven dried 3-neck round bottom flask, equipped with a magnetic stirrer, a thermometer, an addition funnel, a septum and a nitrogen inlet, was added 10 mL of 1M boron tribromide in methylene chloride, by syringe. The BBr3 was cooled to -65 C with a dry ice/acetone bath and 0.9 g (3.3 mmol) of 6-ethyl-5-methoxy-2-p... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cncnc1.c1ccccc1 | Other | O | null | 1.5 | C#CCn1c(-c2ccccc2)nc(CC)c(OC)c1=O>O>C#CCn1c(-c2ccccc2)nc(CC)c(O)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b5423c5215ee415abe3ef0b650a1ea4e | C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O.C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O>>C#CCN1C(=O)C(CC#N)C(CC)(CC)N=C1c1ccccc1 | FC(C(=O)OC(C(F)(F)F)=O)(F)F.NC(=O)CC=1C(N(C(=NC1CC)C1=CC=CC=C1)CC#C)=O.NC(=O)CC=1C(N(C(=NC1CC)C1=CC=CC=C1)CC#C)=O.N1=CC=CC=C1>>C(C)C1(C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC#N)CC | O=[C:9]([CH2:8][c:7]1[c:5](=[O:6])[n:4]([CH2:3][C:2]#[CH:1])[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:16][c:11]1[CH2:14][CH3:15])[NH2:10].C#CCn1c(-c2ccccc2)nc([CH2:12][CH3:13])c(CC(N)=O)c1=O>>[CH:1]#[C:2][CH2:3][N:4]1[C:5](=[O:6])[CH:7]([CH2:8][C:9]#[N:10])[C:11]([CH2:12][CH3:13])([CH2:14][CH3:15])[N:16]=[... | C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O.C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O | C#CCN1C(=O)C(CC#N)C(CC)(CC)N=C1c1ccccc1 | null | null | CCOCC.C1CCOC1 | C-C Coupling | OtherReaction | 1b263c8b01f51ed84eaf98344ae82c45c59fae78da851f7370a0e942d924e48e | e3747cc44512240445b802b2047ca2b6f84ae8fab0d24a606f2e5eeb5fddc92d | O=C1CCN=C(c2ccccc2)N1 | C#C-C-n1:c(-c2:c:c:c:c:c:2):n:c(-[CH2;D2;+0:1]-[C;D1;H3:2]):c(-C-C(-N)=O):c:1=O.O=[C;H0;D3;+0:3](-[NH2;D1;+0:4])-[C:5]-[c;H0;D3;+0:6]1:[c;H0;D3;+0:7](-[C:8]-[C;D1;H3:9]):[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[n;H0;D3;+0:17](-[C:18]-[C:19]#[C;D1;H1:20]):[c;H0;D3;+0:21]:1=[O;D1;H... | 49.8 | [{"value": 49.8, "product": "C(C)C1(C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC#N)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred suspension of 0.25 g (0.85 mmol) of 5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 275) in 12 mL of THF was cooled in an icebath and 0.15 mL (1.9 mmol) of pyridine was added followed by 0.13 mL (0.92 mmol) of trifluoroacetic anhydride. The mixture was stirred in the ice bath f... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amide.Alkyne | Nitrile.Tertiary amide | c1cncnc1.c1cncnc1.c1ccccc1 | C1=NCCC[NH]1 | C1=NCCC[NH]1.c1ccccc1 | HO- | CCOCC.C1CCOC1 | null | null | C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O.C#CCn1c(-c2ccccc2)nc(CC)c(CC(N)=O)c1=O>CCOCC.C1CCOC1>C#CCN1C(=O)C(CC#N)C(CC)(CC)N=C1c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2711ddf9e8434df4b8105ee87a87cff2 | CN=C=O.Nc1ccc(F)cc1F>>CNC(=O)Nc1ccc(F)cc1F | CN=C=O.FC1=C(N)C=CC(=C1)F>>FC1=C(C=CC(=C1)F)NC(=O)NC | [CH3:1][N:2]=[C:3]=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[F:13]>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[F:13] | CN=C=O.Nc1ccc(F)cc1F | CNC(=O)Nc1ccc(F)cc1F | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccccc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 1 | HOUR | Methyl isocyanate (9.6 g, 10 mL, 0.174 mol) is added to a solution of 2,4-difluoroaniline (15 g, 0.116 mol) in toluene. The reaction mixture is stirred for 1 hour and filtered to obtain a solid. The solid is washed with hexanes and air-dried to give the title product as an off-white solid, mp 182°-183° C.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1 | null | C1(=CC=CC=C1)C | null | 1 | CN=C=O.Nc1ccc(F)cc1F>C1(=CC=CC=C1)C>CNC(=O)Nc1ccc(F)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e4418b697e514e7891fd2f8cc0451b85 | Cn1c(=O)[nH]c(=O)n(-c2ccc(F)cc2Cl)c1=O.O=[N+]([O-])O>>Cn1c(=O)[nH]c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | [N+](=O)(O)[O-].ClC1=C(C=CC(=C1)F)N1C(N(C(NC1=O)=O)C)=O>>ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(NC1=O)=O)C)=O | [CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[n:8](-[c:9]2[cH:10][cH:11][c:15]([F:16])[cH:17][c:18]2[Cl:19])[c:20]1=[O:21].O[N+:12](=[O:13])[O-:14]>>[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:6](=[O:7])[n:8](-[c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([F:16])[cH:17][c:18]2[Cl:19])[c:20]1=[O:21] | Cn1c(=O)[nH]c(=O)n(-c2ccc(F)cc2Cl)c1=O.O=[N+]([O-])O | Cn1c(=O)[nH]c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[F;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[F;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | 75.6 | [{"value": 75.6, "product": "ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(NC1=O)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Nitric acid (70% real, 8.3 mL, 0.131 mol) is added to a solution of 1-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (32.4 g, 0.119 mol) in concentrated sulfuric acid while maintaining the reaction mixture temperature below 10° C. After the addition is complete, the reaction mixture is stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ncncn1.c1ccccc1 | HO- | S(O)(O)(=O)=O | null | 0.5 | Cn1c(=O)[nH]c(=O)n(-c2ccc(F)cc2Cl)c1=O.O=[N+]([O-])O>S(O)(O)(=O)=O>Cn1c(=O)[nH]c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-08b8b8866d334d3cae4bec9581c21467 | Cn1c(=O)[nH]c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O>>CN1CN=CN(c2cc(N)c(F)cc2Cl)C1 | ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(NC1=O)=O)C)=O.[H][H]>>NC=1C(=CC(=C(C1)N1CN(CN=C1)C)Cl)F | O=[c:3]1[n:2]([CH3:1])[c:16](=O)[n:6](-[c:7]2[cH:8][c:9]([N+:10](=O)[O-])[c:11]([F:12])[cH:13][c:14]2[Cl:15])[c:5](=O)[nH:4]1>>[CH3:1][N:2]1[CH2:3][N:4]=[CH:5][N:6]([c:7]2[cH:8][c:9]([NH2:10])[c:11]([F:12])[cH:13][c:14]2[Cl:15])[CH2:16]1 | Cn1c(=O)[nH]c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | CN1CN=CN(c2cc(N)c(F)cc2Cl)C1 | null | [Pt] | C(C)(=O)OCC | Reduction | OtherReaction | a12ef5c8c6b913d30cb7c8dc2ae210db0c0600ef67a885c2006dbb9ecfbe343f | 26a2c3d4c194185f138d82af968f6432e8cc58ea35d694a1df2cd162a2f92ecb | C1=NCNCN1c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5](-[Cl;D1;H0:6]):[c;H0;D3;+0:7](-[n;H0;D3;+0:8]2:[c;H0;D3;+0:9](=O):[n;H0;D3;+0:10](-[C;D1;H3:11]):[c;H0;D3;+0:12](=O):[nH;D2;+0:13]:[c;H0;D3;+0:14]:2=O):[c:15]:1>>[C;D1;H3:11]-[N;H0;D3;+0:10]1-[CH2;D2;+0:9]-[N;H0;D3;+0:8](-[c;H0;D3;+0:7]2:[c:15]:[c:2](-[NH2;D1;+0:1]):[c:3]:... | null | [] | null | null | null | null | A mixture of 1-(2-chloro-4-fluoro-5-nitrophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (28.5 g, 0.09 mol) and 5% platinum on activated carbon (1 g) in ethyl acetate is hydrogenated at 55 psi until hydrogen uptake is complete. The reaction mixture is then filtered and concentrated in vacuo to give the title product... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine.Tertiary amine.Tertiary amine | c1ncncn1 | C1=NC[NH]C[NH]1 | C1=NC[NH]C[NH]1.c1ccccc1 | Other | [Pt].C(C)(=O)OCC | null | null | Cn1c(=O)[nH]c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O>[Pt].C(C)(=O)OCC>CN1CN=CN(c2cc(N)c(F)cc2Cl)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6bab90c4b53c475ea6ce599eec07ade5 | CCOC(=O)CN.O=C=Nc1ccc(F)c([N+](=O)[O-])c1>>CCOC(=O)CNC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | O.Cl.C(C)OC(CN)=O.FC1=C(C=C(C=C1)N=C=O)[N+](=O)[O-].C(C)N(CC)CC>>FC1=C(C=C(C=C1)NC(=O)NCC(=O)OCC)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH2:7].[C:8](=[O:9])=[N:10][c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([N+:17](=[O:18])[O-:19])[cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | CCOC(=O)CN.O=C=Nc1ccc(F)c([N+](=O)[O-])c1 | CCOC(=O)CNC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | null | null | O1CCCC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | 56.1 | [{"value": 56.1, "product": "FC1=C(C=C(C=C1)NC(=O)NCC(=O)OCC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-fluoro-3-nitrophenyl isocyanate (10 g, 0.055 mol) in anhydrous tetrahydrofuran is cooled to 0° C., treated with glycine ethyl ester hydrochloride (7.7 g, 0.055 mol), treated with triethylamine (5.56 g, 0.055 mol) while maintaining the temperature below 10° C., stirred at room temperature for 1 hour and ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1 | null | O1CCCC1 | null | 1 | CCOC(=O)CN.O=C=Nc1ccc(F)c([N+](=O)[O-])c1>O1CCCC1>CCOC(=O)CNC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c5aff79410674f0180c8c0f0b265e45b | CCOC(=O)CNC(=O)Nc1ccc(F)c([N+](=O)[O-])c1>>CCOC(=O)CNC(=O)Nc1ccc(F)c(N)c1 | FC1=C(C=C(C=C1)NC(=O)NCC(=O)OCC)[N+](=O)[O-].[H][H]>>NC=1C=C(C=CC1F)NC(=O)NCC(=O)OCC | O=[N+:17]([O-])[c:16]1[c:14]([F:15])[cH:13][cH:12][c:11]([NH:10][C:8]([NH:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:9])[cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([NH2:17])[cH:18]1 | CCOC(=O)CNC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | CCOC(=O)CNC(=O)Nc1ccc(F)c(N)c1 | null | [Pt] | C(C)(=O)OCC | 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] | 60.8 | [{"value": 60.8, "product": "NC=1C=C(C=CC1F)NC(=O)NCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-[(4-fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl ester (8 g, 0.029 mol) and 5% platinum on activated carbon (0.5 g) in ethyl acetate is hydrogenated at 50 psi until hydrogen uptake is complete. The reaction mixture is then filtered and cooled in an ice-bath until a solid forms. The solid is collected by... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pt].C(C)(=O)OCC | null | null | CCOC(=O)CNC(=O)Nc1ccc(F)c([N+](=O)[O-])c1>[Pt].C(C)(=O)OCC>CCOC(=O)CNC(=O)Nc1ccc(F)c(N)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-79c673a5defa413ebe1182aa02579411 | CC(C)OC(=O)CBr.Cn1c(=O)[nH]c(=O)n(-c2ccc(F)cc2Cl)c1=O>>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2ccc(F)cc2Cl)c1=O | O.ClC1=C(C=CC(=C1)F)N1C(N(C(NC1=O)=O)C)=O.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OC(C)C>>ClC1=C(C=CC(=C1)F)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O | Br[CH2:7][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6].[nH:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][c:22]2[Cl:23])[c:24]1=[O:25]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[cH:17][cH:18][c:19]([F:... | CC(C)OC(=O)CBr.Cn1c(=O)[nH]c(=O)n(-c2ccc(F)cc2Cl)c1=O | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2ccc(F)cc2Cl)c1=O | null | null | CN(C=O)C.CCOCC.C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 42369dcf6c82c4deef5c2c853244075c2d58469f08013f2ed6a1b03bbe51bb5a | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C;D1;H3:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[c:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14]:1=[O;D1;H0:15]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:11](=[O;D1;H0:12]):[#7;a:9](-[c:10]):[c:8]:[#7;a:7](-[C;D1;H3:6]):[c:14]:1=[O;D1;H0:15] | 92.4 | [{"value": 92.4, "product": "ClC1=C(C=CC(=C1)F)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 1-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (40.9 g, 0.150 mol), potassium carbonate (31.1 g, 0.225 mol) and isopropyl bromoacetate (29.1 mL, 0.225 mol) in N,N-dimethylformamide is stirred at room temperature for 2 hours, poured into water and extracted with ethyl acetate. The or... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncncn1 | c1ncncn1 | c1ncncn1.c1ccccc1 | HBr | CN(C=O)C.CCOCC.C(Cl)Cl | null | 2 | CC(C)OC(=O)CBr.Cn1c(=O)[nH]c(=O)n(-c2ccc(F)cc2Cl)c1=O>CN(C=O)C.CCOCC.C(Cl)Cl>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2ccc(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3e822e48328449ad872c68dab16e1be0 | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2ccc(F)cc2Cl)c1=O.O=[N+]([O-])O>>Cn1c(=O)n(CC(=O)O)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | [N+](=O)(O)[O-].ClC1=C(C=CC(=C1)F)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O.[N+](=O)(O)[O-].[N+](=O)(O)[O-].[N+](=O)(O)[O-]>>ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)O)=O | CC(C)[O:9][C:7]([CH2:6][n:5]1[c:3](=[O:4])[n:2]([CH3:1])[c:24](=[O:25])[n:12](-[c:13]2[cH:14][cH:15][c:19]([F:20])[cH:21][c:22]2[Cl:23])[c:10]1=[O:11])=[O:8].O[N+:16](=[O:17])[O-:18]>>[CH3:1][n:2]1[c:3](=[O:4])[n:5]([CH2:6][C:7](=[O:8])[OH:9])[c:10](=[O:11])[n:12](-[c:13]2[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]([F... | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2ccc(F)cc2Cl)c1=O.O=[N+]([O-])O | Cn1c(=O)n(CC(=O)O)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | null | null | S(O)(O)(=O)=O | Functional Group Addition | OtherReaction | 749ba82328ac86653dcc57dc3bef14c2a0842e6e973f7cf55c9a50f90810e24e | a9f52bf538fe1f8e7ae329cb07f47e34e1583577eae763d4cc94b0decd80b1c6 | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | C-C(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[F;D1;H0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10].O-[N+;H0;D3:11](-[O;-;D1;H0:12])=[O;D1;H0:13]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[F;D1;H0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[N+;H0;D3:11](-[O;-;D1;H0:12])=[O;D1;H0:13]):[c:9]:[c:10] | null | [] | null | null | 8 | HOUR | A solution of isopropyl 3-(2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (48.7 g, 0.0508 mol) in concentrated sulfuric acid is cooled to 0° C., treated with 90% nitric acid (2.6 mL), stirred at room temperature overnight, treated with 90% nitric acid (1.0 mL), stirred for 4 hours, tr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrate | Carboxylic acid.Nitro group | c1ccccc1 | c1ccccc1 | c1ncncn1.c1ccccc1 | HO- | S(O)(O)(=O)=O | null | 8 | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2ccc(F)cc2Cl)c1=O.O=[N+]([O-])O>S(O)(O)(=O)=O>Cn1c(=O)n(CC(=O)O)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9280354c10d14447b163cc4be4526af1 | CC(C)O.Cn1c(=O)n(CC(=O)O)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O>>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)O)=O.S(O)(O)(=O)=O.CC(C)O>>ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O | [CH3:1][CH:2]([CH3:3])[OH:4].O[C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:22]([F:23])[cH:24][c:25]2[Cl:26])[c:27]1=[O:28]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[... | CC(C)O.Cn1c(=O)n(CC(=O)O)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | null | null | null | Protection | Esterification of Carboxylic Acids | 624bf219458ba212c982344d7c3d6088244bf818423b8912fbf03efe5373c5bf | 547c73c17c71bc10d21cd3cdbafe9d7a279f866fe729eea28fdc1be18f1a2791 | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[OH;D1;+0:8]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | null | null | null | null | A solution of 3-(2-chloro-4-fluoro-5-nitrophenyl)-tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetic acid (43.6 g, 0.105 mol) and concentrated sulfuric acid (25 mL) in 2-propanol (300 mL) is refluxed for 12 hours, cooled to room temperature and filtered to obtain a solid. The solid is dried to give the title prod... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ncncn1.c1ccccc1 | HO- | null | null | null | CC(C)O.Cn1c(=O)n(CC(=O)O)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O>>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-94f05994d0a745e9988e389fe7fb1fc2 | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O>>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O | [H][H].ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O.[H][H].CCOCC>>NC=1C(=CC(=C(C1)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O)Cl)F | O=[N+:19]([O-])[c:18]1[cH:17][c:16](-[n:15]2[c:13](=[O:14])[n:11]([CH3:12])[c:9](=[O:10])[n:8]([CH2:7][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6])[c:25]2=[O:26])[c:23]([Cl:24])[cH:22][c:20]1[F:21]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[cH:17][c:18... | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O | null | [Pt].[Pt] | C(Cl)Cl.C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of isopropyl 3-(2-chloro-4-fluoro-5-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (34.8 g, 0.0835 mol) and 5% platinum on carbon (3.48 g) in ethyl acetate is hydrogenated until about 90 psi of hydrogen is taken up. The reaction mixture is then filtered and concentrated in vacuo to obta... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ncncn1.c1ccccc1 | Other | [Pt].[Pt].C(Cl)Cl.C(C)(=O)OCC | null | null | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc([N+](=O)[O-])c(F)cc2Cl)c1=O>[Pt].[Pt].C(Cl)Cl.C(C)(=O)OCC>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0ea27041f7c3480cb095d9b064085a09 | CCOC(=O)C(Br)CBr.NCCS>>CCOC(=O)C1CSCCN1 | NCCS.C(C)N(CC)CC.BrC(C(=O)OCC)CBr.C(Cl)(Cl)Cl.C1(=CC=CC=C1)C>>N1C(CSCC1)C(=O)OCC | Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]Br.[SH:8][CH2:9][CH2:10][NH2:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][S:8][CH2:9][CH2:10][NH:11]1 | CCOC(=O)C(Br)CBr.NCCS | CCOC(=O)C1CSCCN1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 134ffb04ad0575590e84053a59e6706e87e197197b1d439a5da6a271d27904ca | 16dd093b51b23984a6b8d17db3e4d7c993697754e7fc0e4d8a19aecb6fefa1c8 | C1CSCCN1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2](-Br)-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[C:8]-[C:9]-[SH;D1;+0:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:2]1-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[C:9]-[C:8]-[NH;D2;+0:7]-1 | null | [] | null | null | 2.5 | HOUR | A warm solution of 2-aminoethanethiol (10.0 g, 0.130 mol) and triethylamine (36 mL, 0.260 mol) in chloroform is added over 5 minutes to a solution of ethyl 2,3-di-bromopropionate (33.9 g, 0.130 mol) in a chloroform/toluene (1:1.6) solution. The reaction mixture is stirred at room temperature for 2.5 hours, filtered and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide.Ester.Primary amine.Aliphatic thiol | Ester.Secondary amine.Monosulfide | null | C1CSCCN1 | C1CSCCN1 | HBr | C(Cl)(Cl)Cl | null | 2.5 | CCOC(=O)C(Br)CBr.NCCS>C(Cl)(Cl)Cl>CCOC(=O)C1CSCCN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c45683f083c467ebf79ecae3d3dc9a0 | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)C4CSCCN4C3=O)c(F)cc2Cl)c1=O.[O-][I+3]([O-])([O-])[O-]>>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)C4CS(=O)CCN4C3=O)c(F)cc2Cl)c1=O | ClC1=C(C=C(C(=C1)F)N1C(N2C(CSCC2)C1=O)=O)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O.CCOCC.I(=O)(=O)(=O)[O-].[Na+]>>ClC1=C(C=C(C(=C1)F)N1C(N2C(CS(CC2)=O)C1=O)=O)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O | [CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[cH:17][c:18]([N:19]3[C:20](=[O:21])[CH:22]4[CH2:23][S:24][CH2:26][CH2:27][N:28]4[C:29]3=[O:30])[c:31]([F:32])[cH:33][c:34]2[Cl:35])[c:36]1=[O:37].[O-][I+3]([O-])([O-])[O-:25]>>[CH3:1][CH:2]([CH3:3])[O:4][C:... | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)C4CSCCN4C3=O)c(F)cc2Cl)c1=O.[O-][I+3]([O-])([O-])[O-] | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)C4CS(=O)CCN4C3=O)c(F)cc2Cl)c1=O | null | null | CO.C(Cl)Cl.O | Oxidation | OtherReaction | b4a0685a09bdb9688c5dc9373a81bcecf915198f73d178e3ae74b21a40965ff4 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=C1C2CS(=O)CCN2C(=O)N1c1cccc(-n2c(=O)[nH]c(=O)[nH]c2=O)c1 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[#7:5]-[C:6]-[C:7]-[S;H0;D2;+0:8]-[C:9]-1.[O-;H0;D1:10]-[I+3](-[O-])(-[O-])-[O-]>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[#7:5]-[C:6]-[C:7]-[S;H0;D3;+0:8](=[O;H0;D1;+0:10])-[C:9]-1 | 60.4 | [{"value": 60.4, "product": "ClC1=C(C=C(C(=C1)F)N1C(N2C(CS(CC2)=O)C1=O)=O)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of isopropyl 3-{2-chloro-4-fluoro-5-[5,6,8,8a-tetrahydro-1,3-dioxo-1H-imidazo[5,1-c][1,4]-thiazin-2(3H)-yl]phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.95 g, 1.75 mmol) in methanol (10 mL) is added over 15 minutes to a solution of sodium periodate (0.38 g, 1.78 mmol) in water (10 mL) wh... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | C1CN2C[NH]CC2CS1 | C1CN2C[NH]CC2CS1 | c1ncncn1.c1ccccc1.C1CN2C[NH]CC2CS1 | I- | CO.C(Cl)Cl.O | null | 8 | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)C4CSCCN4C3=O)c(F)cc2Cl)c1=O.[O-][I+3]([O-])([O-])[O-]>CO.C(Cl)Cl.O>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)C4CS(=O)CCN4C3=O)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c36063e545e437080a0d9f9f89c2a06 | BrCCCCBr.CCOC(=O)NNC(=O)OCC>>CCOC(=O)N1CCCCN1C(=O)OCC | BrCCCCBr.C(=O)(OCC)NNC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>N1(N(CCCC1)C(=O)OCC)C(=O)OCC | Br[CH2:7][CH2:8][CH2:9][CH2:10]Br.[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][NH:11][C:12](=[O:13])[O:14][CH2:15][CH3:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:12](=[O:13])[O:14][CH2:15][CH3:16] | BrCCCCBr.CCOC(=O)NNC(=O)OCC | CCOC(=O)N1CCCCN1C(=O)OCC | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 859f3f5b982cf00cd48ce4dee0b290a672abab0fa4228379433ae95e128d543b | 9b2df4ffc85c3bfa472caf43fa08b1e61cbf4a7b843972afe9671fab932acf35 | C1CCNNC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-Br.[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9]1-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:10]-1-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | 69.4 | [{"value": 69.4, "product": "N1(N(CCCC1)C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,4-Dibromobutane (81.4 mL, 0.682 mol) is added over 1 hour to a mixture of 1,2-dicarbethoxyhydrazine (100 g, 0.568 mol) and potassium carbonate (158 g, 1.14 mol) in acetonitrile (600 mL). The resultant reaction mixture is refluxed for 6 hours, cooled to room temperature, and filtered. The filtrate is concentrated in v... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Primary halide.Primary halide | Acylhydrazine.Acylhydrazine.Carbamic ester.Carbamic ester | null | C1CC[NH][NH]C1 | C1CC[NH][NH]C1 | HBr | C(C)#N | null | null | BrCCCCBr.CCOC(=O)NNC(=O)OCC>C(C)#N>CCOC(=O)N1CCCCN1C(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-abde48b4f1894595a808afe5690eeb6d | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.S=C(Cl)Cl>>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N=C=S)c(F)cc2Cl)c1=O | C(=S)(Cl)Cl.NC=1C(=CC(=C(C1)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O)Cl)F.C(C)N(CC)CC>>ClC1=C(C=C(C(=C1)F)N=C=S)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O | [CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[cH:17][c:18]([NH2:19])[c:22]([F:23])[cH:24][c:25]2[Cl:26])[c:27]1=[O:28].Cl[C:20](Cl)=[S:21]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]... | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.S=C(Cl)Cl | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N=C=S)c(F)cc2Cl)c1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[S;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 4 | HOUR | Thiophosgene (0.50 mL, 6.5 mmol) is added over 45 minutes to a solution of isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (2.5 g, 6.5 mmol), and triethylamine (1.8 mL, 13.0 mmol) in tetrahydrofuran. The reaction mixture is stirred at room temperature for 4 hours, ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | c1ncncn1.c1ccccc1 | HCl | O1CCCC1 | null | 4 | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.S=C(Cl)Cl>O1CCCC1>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N=C=S)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e03a241be2b4b53bf88ccfacb21967f | CC(=O)Cl.Nc1ccc(Cl)cc1F>>CC(=O)Nc1ccc(Cl)cc1F | C(C)(=O)OCC.C(C)(=O)Cl.ClC1=CC(=C(N)C=C1)F.C(C)N(CC)CC>>ClC1=CC(=C(NC(C)=O)C=C1)F | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[F:12]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[F:12] | CC(=O)Cl.Nc1ccc(Cl)cc1F | CC(=O)Nc1ccc(Cl)cc1F | null | null | C(C)O.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | Acetyl chloride (24.2 mL, 0.34 mol) is added slowly to a solution of 4-chloro-2-fluoroaniline (49.4 g, 0.34 mol), and triethylamine (47 mL, 0.34 mol) in tetrahydrofuran while maintaining the reaction mixture temperature below 20° C. After the addition is complete, the reaction mixture is stirred overnight at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(C)O.O1CCCC1 | null | 8 | CC(=O)Cl.Nc1ccc(Cl)cc1F>C(C)O.O1CCCC1>CC(=O)Nc1ccc(Cl)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b4cbb9aa494e49f7b3f195512e6252b9 | CC(=O)Nc1ccc(Cl)cc1F.O=[N+]([O-])O>>CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F | ClC1=CC(=C(NC(C)=O)C=C1)F.[N+](=O)(O)[O-]>>ClC1=CC(=C(NC(C)=O)C=C1[N+](=O)[O-])F | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:11]([Cl:12])[cH:13][c:14]1[F:15].O[N+:8](=[O:9])[O-:10]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([Cl:12])[cH:13][c:14]1[F:15] | CC(=O)Nc1ccc(Cl)cc1F.O=[N+]([O-])O | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | 0 | CELSIUS | 10 | MINUTE | A mixture of 4'-chloro-2'-fluoroacetanilide (51 g, 0.272 mol) in concentrated sulfuric acid (100 mL) is cooled to 0° C., treated with nitric acid (90% real, 14 mL, 0.300 mol) over 45 minutes, stirred for 10 minutes, and poured onto ice. The resultant aqueous mixture is filtered to obtain a tan solid which is washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | S(O)(O)(=O)=O | 0 | 0.166667 | CC(=O)Nc1ccc(Cl)cc1F.O=[N+]([O-])O>S(O)(O)(=O)=O>CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fdb5cf4636964e228521df4be25b6c2c | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F>>CC(=O)Nc1cc(N)c(Cl)cc1F | ClC1=CC(=C(NC(C)=O)C=C1[N+](=O)[O-])F.[H][H]>>NC=1C(=CC(=C(NC(C)=O)C1)F)Cl | O=[N+:8]([O-])[c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[c:12]([F:13])[cH:11][c:9]1[Cl:10]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:9]([Cl:10])[cH:11][c:12]1[F:13] | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F | CC(=O)Nc1cc(N)c(Cl)cc1F | null | [Pt] | C(C)O.O1CCCC1 | 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] | null | [] | null | null | null | null | A mixture of 4'-chloro-2'-fluoro-5'-nitroacetanilide (35.2 g, 151 mmol), and 5% platinum on carbon (7.0 g, 20 wt/wt %) in an ethanol/tetrahydrofuran (2:1) solution is hydrogenated until 28 psi of hydrogen is taken up. The reaction mixture is then filtered, and concentrated in vacuo to give the title product as a tan so... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pt].C(C)O.O1CCCC1 | null | null | CC(=O)Nc1cc([N+](=O)[O-])c(Cl)cc1F>[Pt].C(C)O.O1CCCC1>CC(=O)Nc1cc(N)c(Cl)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a556d937a384abda5eb0822445fcd79 | C#CCN.CC(=O)Nc1cc(N)c(Cl)cc1F.O=C(Cl)Oc1ccccc1>>C#CCNC(=O)Nc1cc(NC(C)=O)c(F)cc1Cl | C(C#C)N.NC=1C(=CC(=C(NC(C)=O)C1)F)Cl.C(C)N(CC)CC.C1(=CC=CC=C1)OC(=O)Cl>>C(C)(=O)NC=1C(=CC(=C(C1)NC(=O)NCC#C)Cl)F | [CH:1]#[C:2][CH2:3][NH2:4].[NH2:7][c:8]1[cH:9][c:10]([NH:11][C:12]([CH3:13])=[O:14])[c:15]([F:16])[cH:17][c:18]1[Cl:19].Cl[C:5](Oc1ccccc1)=[O:6]>>[CH:1]#[C:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]([NH:11][C:12]([CH3:13])=[O:14])[c:15]([F:16])[cH:17][c:18]1[Cl:19] | C#CCN.CC(=O)Nc1cc(N)c(Cl)cc1F.O=C(Cl)Oc1ccccc1 | C#CCNC(=O)Nc1cc(NC(C)=O)c(F)cc1Cl | null | null | O.C(C)(=O)OCC.O1CCCC1 | Acylation | OtherReaction | 8991b331000413918f835d1c1bbc39cacc8c099ebed044fdd14fbbac35025775 | 9e21e129777f166dc879d63e1b5cf3ebfee62ae901ede29dec0cc02d1fd57a7f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c:c:c:1.[C;D1;H1:3]#[C:4]-[C:5]-[NH2;D1;+0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H1:3]#[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 75 | MINUTE | A solution of 5'-amino-4'-chloro-2'-fluoroacetanilide (11.25 g, 55.6 mmol), and triethylamine (7.70 mL, 55.6 mmol) in tetrahydrofuran is added dropwise to a stirred solution of phenylchloroformate (8.70 mL, 69.4 mmol) in tetrahydrofuran while maintaining the reaction mixture temperature at 25°-30° C. After the addition... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.Primary amine | Urea | c1ccccc1 | null | c1ccccc1 | HCl | O.C(C)(=O)OCC.O1CCCC1 | null | 1.25 | C#CCN.CC(=O)Nc1cc(N)c(Cl)cc1F.O=C(Cl)Oc1ccccc1>O.C(C)(=O)OCC.O1CCCC1>C#CCNC(=O)Nc1cc(NC(C)=O)c(F)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9562367f4fb64f8a9fa6a9e9643f95bb | C#CCNC(=O)Nc1cc(NC(C)=O)c(F)cc1Cl.O=C=NC(=O)Cl>>C#CCn1c(=O)[nH]c(=O)n(-c2cc(NC(C)=O)c(F)cc2Cl)c1=O | C(C)(=O)NC=1C(=CC(=C(C1)NC(=O)NCC#C)Cl)F.N1=CC=CC=C1.N1=CC=CC=C1.C(=NC(=O)Cl)=O.C(=NC(=O)Cl)=O>>ClC1=CC(=C(NC(C)=O)C=C1N1C(N(C(NC1=O)=O)CC#C)=O)F | [CH:1]#[C:2][CH2:3][NH:4][C:23]([NH:10][c:11]1[cH:12][c:13]([NH:14][C:15]([CH3:16])=[O:17])[c:18]([F:19])[cH:20][c:21]1[Cl:22])=[O:24].Cl[C:5](=[O:6])[N:7]=[C:8]=[O:9]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](=[O:6])[nH:7][c:8](=[O:9])[n:10](-[c:11]2[cH:12][c:13]([NH:14][C:15]([CH3:16])=[O:17])[c:18]([F:19])[cH:20][c:21]2[Cl:22... | C#CCNC(=O)Nc1cc(NC(C)=O)c(F)cc1Cl.O=C=NC(=O)Cl | C#CCn1c(=O)[nH]c(=O)n(-c2cc(NC(C)=O)c(F)cc2Cl)c1=O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | d450124a69c05c689cc30827449dfbc10d3158a711cfc2b694f01c10cd664df3 | 79088c5104e3c5a05b4759d3458d7361a5024a2ee1cbcc7fd6e408b3e17df989 | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[C;D1;H1:6]#[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:12]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[C;D1;H1:6]#[C:7]-[C:8]-[n;H0;D3;+0:9]1:[c;H0;D3;+0:10](=[O;D1;H0:11]):[n;H0;D3;+0:12](-[c;H0;D3;+0:1... | null | [] | null | null | 8 | HOUR | A mixture of 1-(5-acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea (4.50 g, 15.9 mmol), and pyridine (2.56 mL, 31.8 mmol) in methylene chloride is treated with N-(chlorocarbonyl) isocyanate (1.92 mL, 23.9 mmol), stirred at room temperature overnight, refluxed for 90 minutes, cooled to room temperature, treated wit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Urea.Isocyanate | null | null | c1ncncn1 | c1ncncn1.c1ccccc1 | HCl | C(Cl)Cl | null | 8 | C#CCNC(=O)Nc1cc(NC(C)=O)c(F)cc1Cl.O=C=NC(=O)Cl>C(Cl)Cl>C#CCn1c(=O)[nH]c(=O)n(-c2cc(NC(C)=O)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d9d75ac841d479a9bb6bcb95675d2f3 | C#CCn1c(=O)[nH]c(=O)n(-c2cc(NC(C)=O)c(F)cc2Cl)c1=O>>C#CCn1c(=O)[nH]c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O | [OH-].[Na+].ClC1=CC(=C(NC(C)=O)C=C1N1C(N(C(NC1=O)=O)CC#C)=O)F.Cl.C(C)(=O)OCC>>NC=1C(=CC(=C(C1)N1C(N(C(NC1=O)=O)CC#C)=O)Cl)F | CC(=O)[NH:14][c:13]1[cH:12][c:11](-[n:10]2[c:8](=[O:9])[nH:7][c:5](=[O:6])[n:4]([CH2:3][C:2]#[CH:1])[c:20]2=[O:21])[c:18]([Cl:19])[cH:17][c:15]1[F:16]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](=[O:6])[nH:7][c:8](=[O:9])[n:10](-[c:11]2[cH:12][c:13]([NH2:14])[c:15]([F:16])[cH:17][c:18]2[Cl:19])[c:20]1=[O:21] | C#CCn1c(=O)[nH]c(=O)n(-c2cc(NC(C)=O)c(F)cc2Cl)c1=O | C#CCn1c(=O)[nH]c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=c1[nH]c(=O)n(-c2ccccc2)c(=O)[nH]1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 82.2 | [{"value": 82.2, "product": "NC=1C(=CC(=C(C1)N1C(N(C(NC1=O)=O)CC#C)=O)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4'-chloro-2'-fluoro-5'-[hexahydro-2,4,6-trioxo-3-(2-propynyl)-s-triazin-1-yl]acetanilide (3.00 g, 8.5 mmol), and 3N hydrochloric acid (25 mL) in ethanol (50 mL) is refluxed for 3 hours, cooled to room temperature, and poured into ethyl acetate. 3N sodium hydroxide solution (25 mL) is added to the organic s... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ncncn1.c1ccccc1 | HO- | C(C)O | null | null | C#CCn1c(=O)[nH]c(=O)n(-c2cc(NC(C)=O)c(F)cc2Cl)c1=O>C(C)O>C#CCn1c(=O)[nH]c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9fc8235e42584d779056ec0da7bbdc76 | C#CCn1c(=O)[nH]c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.O=C1OC(=O)C2=C1CCCC2>>C#CCn1c(=O)[nH]c(=O)n(-c2cc(N3C(=O)C4=C(CCCC4)C3=O)c(F)cc2Cl)c1=O | NC=1C(=CC(=C(C1)N1C(N(C(NC1=O)=O)CC#C)=O)Cl)F.C1(C2=C(C(=O)O1)CCCC2)=O.C(C)(=O)OCC>>ClC1=CC(=C(C=C1N1C(N(C(NC1=O)=O)CC#C)=O)N1C(=O)C2=C(CCCC2)C1=O)F | [CH:1]#[C:2][CH2:3][n:4]1[c:5](=[O:6])[nH:7][c:8](=[O:9])[n:10](-[c:11]2[cH:12][c:13]([NH2:14])[c:25]([F:26])[cH:27][c:28]2[Cl:29])[c:30]1=[O:31].O1[C:15](=[O:16])[C:17]2=[C:18]([CH2:19][CH2:20][CH2:21][CH2:22]2)[C:23]1=[O:24]>>[CH:1]#[C:2][CH2:3][n:4]1[c:5](=[O:6])[nH:7][c:8](=[O:9])[n:10](-[c:11]2[cH:12][c:13]([N:14]... | C#CCn1c(=O)[nH]c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.O=C1OC(=O)C2=C1CCCC2 | C#CCn1c(=O)[nH]c(=O)n(-c2cc(N3C(=O)C4=C(CCCC4)C3=O)c(F)cc2Cl)c1=O | null | null | C(C)(=O)O | Acylation | OtherReaction | e8011a3b0be1a45acf4cbe99b6add2c178c54f184ca2415e1c1cb07e7aee07ff | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2=C(CCCC2)C(=O)N1c1cccc(-n2c(=O)[nH]c(=O)[nH]c2=O)c1 | [C:1]-[C:2]1=[C:3](-[C:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[C:2]1=[C:3](-[C:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 55.9 | [{"value": 55.9, "product": "ClC1=CC(=C(C=C1N1C(N(C(NC1=O)=O)CC#C)=O)N1C(=O)C2=C(CCCC2)C1=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(5-amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H,3H,5H)-trione (1.50 g, 4.83 mmol), and 3,4,5,6-tetrahydrophthalic anhydride (0.73 g, 4.83 mmol) in acetic acid (3 mL) is heated at 100° C. for 5 hours, cooled, and poured into ethyl acetate, The organic mixture is washed sequentially ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CCC2=C(C1)COC2 | C1CCC2=C(C1)C[NH]C2 | c1ncncn1.c1ccccc1.C1CCC2=C(C1)C[NH]C2 | HO- | C(C)(=O)O | null | null | C#CCn1c(=O)[nH]c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.O=C1OC(=O)C2=C1CCCC2>C(C)(=O)O>C#CCn1c(=O)[nH]c(=O)n(-c2cc(N3C(=O)C4=C(CCCC4)C3=O)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ce2e94879794c84802f9843f2d4155a | Nc1ccc(Cl)cc1F.O=C1OC(=O)C2=C1CCCC2>>O=C1C2=C(CCCC2)C(=O)N1c1ccc(Cl)cc1F | O.C(C)(=O)OCC.ClC1=CC(=C(N)C=C1)F.C1(C2=C(C(=O)O1)CCCC2)=O.C(C)(=O)OCC.ClC1=CC(=C(N)C=C1)F>>ClC1=CC(=C(C=C1)N1C(=O)C2=C(CCCC2)C1=O)F | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]1[F:19].O1[C:2](=[O:1])[C:3]2=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:9]1=[O:10]>>[O:1]=[C:2]1[C:3]2=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:9](=[O:10])[N:11]1[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]1[F:19] | Nc1ccc(Cl)cc1F.O=C1OC(=O)C2=C1CCCC2 | O=C1C2=C(CCCC2)C(=O)N1c1ccc(Cl)cc1F | null | null | C(C)(=O)O | Acylation | OtherReaction | e8011a3b0be1a45acf4cbe99b6add2c178c54f184ca2415e1c1cb07e7aee07ff | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2=C(CCCC2)C(=O)N1c1ccccc1 | [C:1]-[C:2]1=[C:3](-[C:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:1]-[C:2]1=[C:3](-[C:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 69.3 | [{"value": 69.3, "product": "ClC1=CC(=C(C=C1)N1C(=O)C2=C(CCCC2)C1=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol), and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in acetic acid (150 mL) is refluxed for 2 hours, treated with additional 4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into a water/eth... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CCC2=C(C1)COC2 | C1CCC2=C(C1)C[NH]C2 | C1CCC2=C(C1)C[NH]C2.c1ccccc1 | HO- | C(C)(=O)O | null | 8 | Nc1ccc(Cl)cc1F.O=C1OC(=O)C2=C1CCCC2>C(C)(=O)O>O=C1C2=C(CCCC2)C(=O)N1c1ccc(Cl)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b12023f2a354fce9ed4c6252aa46b2d | O=C1C2=C(CCCC2)C(=O)N1c1ccc(Cl)cc1F.O=[N+]([O-])O>>O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F | ClC1=CC(=C(C=C1)N1C(=O)C2=C(CCCC2)C1=O)F.[N+](=O)(O)[O-]>>ClC1=CC(=C(C=C1[N+](=O)[O-])N1C(=O)C2=C(CCCC2)C1=O)F | [O:1]=[C:2]1[C:3]2=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:9](=[O:10])[N:11]1[c:12]1[cH:13][cH:14][c:18]([Cl:19])[cH:20][c:21]1[F:22].O[N+:15](=[O:16])[O-:17]>>[O:1]=[C:2]1[C:3]2=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:9](=[O:10])[N:11]1[c:12]1[cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]([Cl:19])[cH:20][c:21]1[F:22] | O=C1C2=C(CCCC2)C(=O)N1c1ccc(Cl)cc1F.O=[N+]([O-])O | O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C1C2=C(CCCC2)C(=O)N1c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | 101.6 | [{"value": 101.6, "product": "ClC1=CC(=C(C=C1[N+](=O)[O-])N1C(=O)C2=C(CCCC2)C1=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -3 | CELSIUS | 90 | MINUTE | A mixture of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide (24.4 g, 86.7 mmol) in sulfuric acid (150 mL) is cooled to -3° C., treated dropwise with nitric acid (70% real, 6.70 mL, 104 mmol) while maintaining the temperature at 0°-2° C., stirred at room temperature for 90 minutes, and poured onto ice. The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | C1CCC2=C(C1)C[NH]C2.c1ccccc1 | HO- | S(O)(O)(=O)=O | -3 | 1.5 | O=C1C2=C(CCCC2)C(=O)N1c1ccc(Cl)cc1F.O=[N+]([O-])O>S(O)(O)(=O)=O>O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88f06d69204e412d96ef75bebf1aaf76 | O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F>>Nc1cc(N2C(=O)C3=C(CCCC3)C2=O)c(F)cc1Cl | C(C)(=O)OCC.ClC1=CC(=C(C=C1[N+](=O)[O-])N1C(=O)C2=C(CCCC2)C1=O)F>>NC=1C(=CC(=C(C1)N1C(=O)C2=C(CCCC2)C1=O)F)Cl | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([N:5]2[C:6](=[O:7])[C:8]3=[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)[C:14]2=[O:15])[c:16]([F:17])[cH:18][c:19]1[Cl:20]>>[NH2:1][c:2]1[cH:3][c:4]([N:5]2[C:6](=[O:7])[C:8]3=[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)[C:14]2=[O:15])[c:16]([F:17])[cH:18][c:19]1[Cl:20] | O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F | Nc1cc(N2C(=O)C3=C(CCCC3)C2=O)c(F)cc1Cl | null | [Fe] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1C2=C(CCCC2)C(=O)N1c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 10 | MINUTE | Iron powder (7.30 g, 130.7 mmol) is added portionwise to a mixture of N-(4-chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide (10.6 g, 32.7 mmol) in acetic acid (100 mL) at 65° C. After the addition is complete, the reaction mixture is stirred for 10 minutes, and filtered through diatomaceous earth. The fil... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCC2=C(C1)C[NH]C2 | Other | [Fe].C(C)(=O)O | null | 0.166667 | O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F>[Fe].C(C)(=O)O>Nc1cc(N2C(=O)C3=C(CCCC3)C2=O)c(F)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-977e991e320c48a5ae6360a814f9e68c | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.O=C1OC(=O)c2c(F)cccc21>>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)c4cccc(F)c4C3=O)c(F)cc2Cl)c1=O | NC=1C(=CC(=C(C1)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O)Cl)F.FC1=C2C(C(=O)OC2=O)=CC=C1>>ClC1=C(C=C(C(=C1)F)N1C(C=2C(C1=O)=C(C=CC2)F)=O)N2C(N(C(N(C2=O)C)=O)CC(=O)OC(C)C)=O | [CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[n:11]([CH3:12])[c:13](=[O:14])[n:15](-[c:16]2[cH:17][c:18]([NH2:19])[c:31]([F:32])[cH:33][c:34]2[Cl:35])[c:36]1=[O:37].O1[C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][c:26]([F:27])[c:28]2[C:29]1=[O:30]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8... | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.O=C1OC(=O)c2c(F)cccc21 | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)c4cccc(F)c4C3=O)c(F)cc2Cl)c1=O | null | null | C(C)(=O)O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1c1cccc(-n2c(=O)[nH]c(=O)[nH]c2=O)c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D3;+0:6]1-O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]-1:[c:12]>>[O;D1;H0:5]=[C;H0;D3;+0:6]1-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]-1:[c:12] | null | [] | null | null | null | null | A solution of isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (1.0 g, 2.6 mmol) and 3-fluorophthalic anhydride (0.51 g, 3.1 mmol) in acetic acid is refluxed for 6 hours, stirred at room temperature for several days and poured onto ice. The resultant aqueous mixture... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ncncn1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C(C)(=O)O | null | null | CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N)c(F)cc2Cl)c1=O.O=C1OC(=O)c2c(F)cccc21>C(C)(=O)O>CC(C)OC(=O)Cn1c(=O)n(C)c(=O)n(-c2cc(N3C(=O)c4cccc(F)c4C3=O)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7a8f9c1c64f84e7eae13346d27dfc137 | CC(C)OC(=O)CBr.CC(C)OC(=O)Cn1c(=O)[nH]c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O>>CC(C)OC(=O)Cn1c(=O)n(CC(=O)OC(C)C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O | ClC1=C(C=C(C(=C1)F)N=C1SC(N2N1CCCC2)=O)N2C(N(C(NC2=O)=O)CC(=O)OC(C)C)=O.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OC(C)C.O>>ClC1=C(C=C(C(=C1)F)N=C1SC(N2N1CCCC2)=O)N2C(N(C(N(C2=O)CC(=O)OC(C)C)=O)CC(=O)OC(C)C)=O | Br[CH2:12][C:13](=[O:14])[O:15][CH:16]([CH3:17])[CH3:18].[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][n:8]1[c:9](=[O:10])[nH:11][c:19](=[O:20])[n:21](-[c:22]2[cH:23][c:24]([N:25]=[c:26]3[s:27][c:28](=[O:29])[n:30]4[n:31]3[CH2:32][CH2:33][CH2:34][CH2:35]4)[c:36]([F:37])[cH:38][c:39]2[Cl:40])[c:41]1=[O:42]>>[CH3:1][CH... | CC(C)OC(=O)CBr.CC(C)OC(=O)Cn1c(=O)[nH]c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O | CC(C)OC(=O)Cn1c(=O)n(CC(=O)OC(C)C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 42369dcf6c82c4deef5c2c853244075c2d58469f08013f2ed6a1b03bbe51bb5a | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c(=O)n(-c2cccc(N=c3sc(=O)n4n3CCCC4)c2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12](-[c:13]):[c:14](=[O;D1;H0:15]):[nH;D2;+0:16]:[c:17]:1=[O;D1;H0:18]>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12](-[c:13]):[c:14](=[O;D1;H0:15]):[n;H0;D3;+0:16](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3]... | 29.5 | [{"value": 29.5, "product": "ClC1=C(C=C(C(=C1)F)N=C1SC(N2N1CCCC2)=O)N2C(N(C(N(C2=O)CC(=O)OC(C)C)=O)CC(=O)OC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of isopropyl 3-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]-pyridazin-1-ylidene)amino]phenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.85 g, 1.62 mmol), potassium carbonate (0.27 g, 1.95 mmol) and isopropyl bromoacetate (0,353 g, 1.95 mmol)in N,N-dimethylformamide is stirr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ncncn1 | c1ncncn1 | c1ncncn1.c1ccccc1.c1scn2n1CCCC2 | HBr | CN(C=O)C | null | 8 | CC(C)OC(=O)CBr.CC(C)OC(=O)Cn1c(=O)[nH]c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O>CN(C=O)C>CC(C)OC(=O)Cn1c(=O)n(CC(=O)OC(C)C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7e627b3bd4d476c9aa919241c2544ff | C=CCBr.Cn1c(=O)[nH]c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O>>C=CCn1c(=O)n(C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O | O.ClC1=C(C=C(C(=C1)F)N=C1SC(N2N1CCCC2)=O)N2C(N(C(NC2=O)=O)C)=O.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)N1C(N(C(N(C1=O)C)=O)C1=C(C=C(C(=C1)N=C1SC(N2N1CCCC2)=O)F)Cl)=O | Br[CH2:3][CH:2]=[CH2:1].[nH:4]1[c:5](=[O:6])[n:7]([CH3:8])[c:9](=[O:10])[n:11](-[c:12]2[cH:13][c:14]([N:15]=[c:16]3[s:17][c:18](=[O:19])[n:20]4[n:21]3[CH2:22][CH2:23][CH2:24][CH2:25]4)[c:26]([F:27])[cH:28][c:29]2[Cl:30])[c:31]1=[O:32]>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5](=[O:6])[n:7]([CH3:8])[c:9](=[O:10])[n:11](-[c:12]2[... | C=CCBr.Cn1c(=O)[nH]c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O | C=CCn1c(=O)n(C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 84dcf5908feaa31afcb5f12444b3389dbab6d839a84b75317076d533f4c11c42 | 4c606dc54eac846ef90c7b3255999ceff93277747e7c2b0ddd37ccf25562b7c5 | O=c1[nH]c(=O)n(-c2cccc(N=c3sc(=O)n4n3CCCC4)c2)c(=O)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[c:8]):[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:9](=[O;D1;H0:10]):[#7;a:7](-[c:8]):[c:6]:[#7;a:5](-[C;D1;H3:4]):[c:12]:1=[O;D1;H0:13] | 73.3 | [{"value": 73.3, "product": "C(C=C)N1C(N(C(N(C1=O)C)=O)C1=C(C=C(C(=C1)N=C1SC(N2N1CCCC2)=O)F)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 8 | HOUR | A mixture of 1-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)-amino]phenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (1.00 g, 2.27 mmol), potassium carbonate (0.627 g, 4.54 mmol) and allyl bromide (0.329 g, 2.72 mmol) in acetone is stirred overnight at 40° C. and poured in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | c1ncncn1 | c1ncncn1 | c1ncncn1.c1ccccc1.c1scn2n1CCCC2 | HBr | CC(=O)C | 40 | 8 | C=CCBr.Cn1c(=O)[nH]c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O>CC(=O)C>C=CCn1c(=O)n(C)c(=O)n(-c2cc(N=c3sc(=O)n4n3CCCC4)c(F)cc2Cl)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cd96027b0a0d43cfb4c23e75a82d466d | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>>O=C1CCC(c2ccc(Cl)cc2)=NN1 | ClC1=CC=C(C(=O)CCC(=O)O)C=C1.O.NN>>ClC1=CC=C(C=C1)C=1CCC(NN1)=O | [NH2:13][NH2:14].O=[C:5]([CH2:4][CH2:3][C:2](O)=[O:1])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1 | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | null | null | C(C)O | Acylation | OtherReaction | 16e715242dd5e92f711d46176c552652cef6c6f4fed9bc9a09a311d5b0b86cea | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])=[N;H0;D2;+0:9]-[NH;D2;+0:10]-1 | 80 | [{"value": 80.0, "product": "ClC1=CC=C(C=C1)C=1CCC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-(4-chlorobenzoyl)propionic acid (20g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5-... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=NNCCC1 | C1=NNCCC1.c1ccccc1 | HO- | C(C)O | null | null | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>C(C)O>O=C1CCC(c2ccc(Cl)cc2)=NN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-42bdc25833dc410b993a2671ac65a643 | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN>>CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O | ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1.C(C)(=O)[O-].[Na+].Cl.C(C)(C)(C)NN>>ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O | O=[C:7]([c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[CH:15]([CH3:16])[C:17](O)=[O:18].[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][NH2:6]>>[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[N:6]=[C:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[CH2:15][CH2:16][C:17]1=[O:18] | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN | CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O | null | null | C(CCC)O | Acylation | OtherReaction | 4e477d09c29dc9649665c2a512a7ab66ed0db9837b745e511eba3c76a3cc18d7 | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[CH3;D1;+0:4])-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:13]-[NH2;D1;+0:14]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[N;H0;D3;+0:13]1-[N;H0;D2;+0:14]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[CH2;D2;+0:3]-[CH2;D2;+... | 34.4 | [{"value": 34.4, "product": "ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=N[NH]CCC1 | C1=N[NH]CCC1.c1ccccc1 | HO- | C(CCC)O | null | null | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN>C(CCC)O>CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce064075330c45f48a8cd178fcf95efd | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>>O=C(O)CCC(=O)c1cccc(Cl)c1 | C(CCC(=O)OC)(=O)OC.[Na].C(C)O.ClC=1C=C(C(=O)OC)C=CC1.C(CCC(=O)OC)(=O)OC>>ClC=1C=C(C(=O)CCC(=O)O)C=CC1 | COC(=O)[CH2:5][CH2:4][C:2](=[O:1])[O:3]C.CO[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | null | null | CCOCC | C-C Coupling | OtherReaction | 6d482de2a0c1fffe47581cf2d6dc0eefca79628574252eec326be9292f335afe | 1f69704fe402a3eb0e91a243a59f68f972592be61b4c787368515903d4c85726 | c1ccccc1 | C-O-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C.C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Sodium (11 g, spheres) was added to 200 ml ethanol with stirring. When the gas evolution ceased, methyl 3-chlorobenzoate (10 g, 0.057 mole) and dimethyl succinate (9.0 g, 0.615 mole) were added rapidly and the mixture was stirred for 5 minutes at room temperature. The mixture was slowly concentrated on a rotary evapora... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Carboxylic acid.Ketone | null | null | c1ccccc1 | HO- | CCOCC | null | null | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>CCOCC>O=C(O)CCC(=O)c1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-853ac2ea43e24e448317811edbddc04c | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.O=[N+]([O-])O>>CC(C(=O)O)C(=O)c1ccc(Cl)c([N+](=O)[O-])c1 | ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1.[N+](=O)(O)[O-]>>ClC1=C(C=C(C(=O)C(C(=O)O)C)C=C1)[N+](=O)[O-] | [CH3:1][CH:2]([C:3](=[O:4])[OH:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:17]1.O[N+:14](=[O:15])[O-:16]>>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1 | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.O=[N+]([O-])O | CC(C(=O)O)C(=O)c1ccc(Cl)c([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]-[C:10]=[O;D1;H0:11]>>[Cl;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9]-[C:10]=[O;D1;H0:11] | null | [] | 0 | CELSIUS | 30 | MINUTE | To fuming nitric acid (150 ml) was added p-chlorobenzoylpropionic acid (20.0 g), slowly portionwise at 0° C. After the addition was completed the resulting mixture was stirred at 0° C. for 30 minutes and the resulting white solid was suction filtered and washed with water until the pH of the washing liquids was neutral... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 0 | 0.5 | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.O=[N+]([O-])O>>CC(C(=O)O)C(=O)c1ccc(Cl)c([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-df91626c72824b1cb4c0c7f9c249511e | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | CC1=CC=C(C(=O)CCC(=O)O)C=C1.[Cl-].[Al+3].[Cl-].[Cl-].ClCl>>ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl | [CH3:1][c:2]1[cH:3][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1.[Cl:4][Cl:16]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][c:15]1[Cl:16] | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl | Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | d2a751fe92dcfde720edd5e4971c1aa6cc149bff4a6d230cc6b5cac59ec9498c | 861258def4b3bd7367f8a87cde43fe585d40dc3669ea29055dbcb9a2de101a4d | c1ccccc1 | [C;D1;H3:1]-[c:2]1:[cH;D2;+0:3]:[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[cH;D2;+0:9]:1.[Cl;H0;D1;+0:10]-[Cl;H0;D1;+0:11]>>[C;D1;H3:1]-[c:2]1:[c;H0;D3;+0:3](-[Cl;H0;D1;+0:10]):[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:11] | 44.2 | [{"value": 44.2, "product": "ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into mixture of hydrochloric acid and ice an... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide.Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C(Cl)Cl | null | null | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>C(Cl)Cl>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-65c75dc89f17409bb6ee8bc64675c761 | C1=COCCC1.OCC#CCO>>OCC#CCOC1CCCCO1 | C(C#CCO)O.O1CCCC=C1>>O1C(CCCC1)OCC#CCO | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[OH:1][CH2:2][C:3]#[C:4][CH2:5][OH:6]>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.OCC#CCO | OCC#CCOC1CCCCO1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]#[C:9]-[C:10]-[OH;D1;+0:11]>>[C:7]-[C:8]#[C:9]-[C:10]-[O;H0;D2;+0:11]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | 68.8 | [{"value": 68.8, "product": "O1C(CCCC1)OCC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | CCOCC | null | null | C1=COCCC1.OCC#CCO>CCOCC>OCC#CCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1df241b7ff954c60ae215c613fabf759 | C#CC1CCCCC1.C=O>>OCC#CC1CCCCC1 | C1(CCCCC1)C#C.C=O.C=O>>C1(CCCCC1)C#CCO | [CH:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.[O:1]=[CH2:2]>>[OH:1][CH2:2][C:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | C#CC1CCCCC1.C=O | OCC#CC1CCCCC1 | null | null | CCOCC | C-C Coupling | OtherReaction | b068d8bba9f864ba971dd324292d9b3526f0235b4ab7e3a9ce6aa76a39c4a1e7 | 22ebec2cc94dd24863aea8793d450cfe0691e1036be204d1a4c79c16effe90a4 | C1CCCCC1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[C:4]#[CH;D1;+0:5]>>[C:3]-[C:4]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | To a solution of ethyl magesium bromide (prepared from 2.5 g of magnesium turning and 11.3 g of bromoethane) in ether was added dropwise a solution of 10.2 g of cyclohexylacetylene in ether and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and anhydrous formaldehy... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Alkyne | Primary alcohol.Alkyne | null | null | C1CCCCC1 | null | CCOCC | null | null | C#CC1CCCCC1.C=O>CCOCC>OCC#CC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ad3598473f04955b043e8d47bb746e6 | O=C1CCC(c2ccc(Cl)cc2)=NN1>>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1CCC(NN1)=O.C(C)(=O)O.BrBr>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 73c80fbcc9dd7a9125aaf1059d9d4eab31b342d21fc860abf5e65fd78456864b | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1ccc(-c2ccccc2)n[nH]1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])=[N;H0;D2;+0:11]-[NH;D2;+0:12]-1>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[n;H0;D2;+0:11]:[nH;D2;+0:12]:1 | 93.1 | [{"value": 89.0, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | C1=NNCCC1 | c1cccnn1 | c1cccnn1.c1ccccc1 | null | O | null | null | O=C1CCC(c2ccc(Cl)cc2)=NN1>O>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72814c0515e843deab3f2d0998e62084 | FC1(F)CC(Cl)(Cl)C1(F)Cl>>FC1(F)C=C(Cl)C1(F)Cl | ClC1(C(C(C1)(F)F)(F)Cl)Cl.O.Cl>>ClC1(C(C=C1Cl)(F)F)F | Cl[C:5]1([Cl:6])[CH2:4][C:2]([F:1])([F:3])[C:7]1([F:8])[Cl:9]>>[F:1][C:2]1([F:3])[CH:4]=[C:5]([Cl:6])[C:7]1([F:8])[Cl:9] | FC1(F)CC(Cl)(Cl)C1(F)Cl | FC1(F)C=C(Cl)C1(F)Cl | null | null | CCOCC.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | 0ca523bc88d44f4371960ac2ff9ed0bbb8882337b7061f7fba5b4787f1e02481 | 986b135105e7920109b424799136a4a8281fb4a0f49253ce1bf5d4426ed78637 | C1=CCC1 | Cl-[C;H0;D4;+0:1]1(-[Cl;D1;H0:2])-[CH2;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1]1=[CH;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9] | 79 | [{"value": 79.0, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ethe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Alkenyl halide | C1CCC1 | C1=CCC1 | C1=CCC1 | HCl | CCOCC.C(C)N(CC)CC | null | 8 | FC1(F)CC(Cl)(Cl)C1(F)Cl>CCOCC.C(C)N(CC)CC>FC1(F)C=C(Cl)C1(F)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6b35315acbe8476c894bb158bdaa472f | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>>O=C(O)C(F)C(F)(F)C(=O)O | ClC(C(C(=O)O)(F)F)(C(=O)O)F>>FC(C(=O)O)(C(C(=O)O)F)F | Cl[C:6]([C:4]([C:2](=[O:1])[OH:3])([F:5])[F:7])([F:8])[C:9](=[O:10])[OH:11]>>[O:1]=[C:2]([OH:3])[CH:4]([F:5])[C:6]([F:7])([F:8])[C:9](=[O:10])[OH:11] | O=C(O)C(F)(F)C(F)(Cl)C(=O)O | O=C(O)C(F)C(F)(F)C(=O)O | null | [Zn] | O1CCOCC1 | Functional Group Addition | Dehalogenation | 7f145230bfb0115349e969b2f2fa1359cfafe8c166e52b50a867192005e1f5bc | d6722b0df465660a9eeeaca5a8f5b3dbb2d1ebccb44917f2eca97a85bf850d06 | null | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;H0;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[F;D1;H0:7]-[CH;D3;+0:6](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;H0;D1;+0:8])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 40.7 | [{"value": 32.0, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Tertiary halide.Tertiary halide.Secondary halide | null | null | null | Other | [Zn].O1CCOCC1 | null | 10 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>[Zn].O1CCOCC1>O=C(O)C(F)C(F)(F)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1ffe8aa63584752873a03df8fe427f6 | O=C1CCC(=O)O1.c1ccc2ccccc2c1>>O=C(O)CCC(=O)c1cccc2ccccc12 | Cl.[Cl-].[Cl-].[Cl-].[Al+3].C1=CC=CC2=CC=CC=C12.C1(CCC(=O)O1)=O>>C1(=CC=CC2=CC=CC=C12)C(=O)CCC(=O)O | [O:1]=[C:2]1[O:3][C:6](=[O:7])[CH2:5][CH2:4]1.[cH:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | O=C1CCC(=O)O1.c1ccc2ccccc2c1 | O=C(O)CCC(=O)c1cccc2ccccc12 | null | null | [N+](=O)([O-])C1=CC=CC=C1 | C-C Coupling | OtherReaction | d1b47ca78c3ceb45955ddf79d2b2d22c1a0978cf9fa8ded4c5ee0a8331deac4e | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccc2ccccc2c1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11](:[c:12]):[c:13]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | A mixture of naphthalene (40 g) and succinic anhydride (20 g) was added to a well stirred suspension of aluminum trichloride (55 g) in nitrobenzene (140 ml). The resulting mixture was stirred overnight at room temperature. The mixture was then poured slowly onto ice-water (600 g) and acidified with 6N-hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | C1CCOC1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | [N+](=O)([O-])C1=CC=CC=C1 | null | null | O=C1CCC(=O)O1.c1ccc2ccccc2c1>[N+](=O)([O-])C1=CC=CC=C1>O=C(O)CCC(=O)c1cccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64d1801cfcd4465887e5bc7221651fa5 | NN.O=C(O)CCCC(=O)c1ccccc1>>O=c1cccc(-c2ccccc2)nn1 | C(C1=CC=CC=C1)(=O)CCCC(=O)O.NN.O>>C1(=CC=CC=C1)C1=CC=CC(N=N1)=O | [NH2:13][NH2:14].O=[C:6]([CH2:5][CH2:4][CH2:3][C:2](O)=[O:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O: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)[n:13][n:14]1 | NN.O=C(O)CCCC(=O)c1ccccc1 | O=c1cccc(-c2ccccc2)nn1 | null | null | C1(=CC=CC=C1)C.CCOCC | Aromatic Heterocycle Formation | OtherReaction | a31553d36b14882561a6dcdd04ef456bc0e14ea189c472490f94f02ebbe3ca3f | eadf9e657b4bde18ed656e299092aac7dd81eee1face1030775c3edd6ccba31c | O=c1cccc(-c2ccccc2)nn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[NH2;D1;+0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[n;H0;D2;+0... | 39 | [{"value": 39.0, "product": "C1(=CC=CC=C1)C1=CC=CC(N=N1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | null | null | c1cccc[nH]n1 | c1cccc[nH]n1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.CCOCC | null | null | NN.O=C(O)CCCC(=O)c1ccccc1>C1(=CC=CC=C1)C.CCOCC>O=c1cccc(-c2ccccc2)nn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54e336ac6c4f4117baf301a34b00c11e | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>>COC(=O)C1Cc2cc(Cl)ccc2C1=O | COC(OC)=O.[H-].[Na+].ClC=1C=C2CCC(C2=CC1)=O.[H][H]>>C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15] | COC(=O)OC.O=C1CCc2cc(Cl)ccc21 | COC(=O)C1Cc2cc(Cl)ccc2C1=O | null | null | C(OC)COC | C-C Coupling | OtherReaction | c2c31337dfb867d8c28bc65df0ad4496f817a712a58e176523b47d7fdb6e4f91 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | O=C1CCc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | 45 | [{"value": 45.0, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(OC)COC | 60 | null | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>C(OC)COC>COC(=O)C1Cc2cc(Cl)ccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d9aaadeb71b457db37c796786d39ff2 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>>CN(C)C=C(C=O)c1ccc(Cl)cc1 | C([O-])([O-])=O.[K+].[K+].P(=O)(Cl)(Cl)Cl.CN(C)C=O.ClC1=CC=C(C=C1)CC(=O)O>>ClC1=CC=C(C=C1)C(C=O)=CN(C)C | O=[CH:4][N:2]([CH3:1])[CH3:3].O=[C:6]([CH2:5][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[OH:7]>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([CH:6]=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1 | CN(C)C=C(C=O)c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cbf378fe57a2b8d8304e623fb5ce9ee6fb9f6e90d9c6f965226d56b103180e6d | a9c635686380f13b6b5c45d80d4aef36b30fdab0aef140b81f04c277f7ba737d | c1ccccc1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6].O=[CH;D2;+0:7]-[#7:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[#7:8](-[C;D1;H3:10])-[CH;D2;+0:7]=[C;H0;D3;+0:3](-[CH;D2;+0:1]=[O;H0;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Enamine.Aldehyde | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 8 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>C1(=CC=CC=C1)C>CN(C)C=C(C=O)c1ccc(Cl)cc1 |
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