dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-915998a24bba4f2190531cc7ca53e3a6 | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)OCc1ccccc1>>O=C(N[C@H](CO)Cc1ccc(OCc2ccccc2)cc1)OCc1ccccc1 | [Cl-].[Na+].COC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=C(C=C1)OCC1=CC=CC=C1)=O.[Cl-].[Li+].[BH4-].[Na+]>>C(C1=CC=CC=C1)OC1=CC=C(C[C@H](NC(=O)OCC2=CC=CC=C2)CO)C=C1 | CO[C:5]([C@@H:4]([NH:3][C:2](=[O:1])[O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1)=[O:6]>>[O:1]=[C:2]([NH:3][C@H:4]([CH2:5][OH:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH... | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)OCc1ccccc1 | O=C(N[C@H](CO)Cc1ccc(OCc2ccccc2)cc1)OCc1ccccc1 | null | null | C(C)O.O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(NCCc1ccc(OCc2ccccc2)cc1)OCc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:1]-[OH;D1;+0:2] | 99.9 | [{"value": 99.9, "product": "C(C1=CC=CC=C1)OC1=CC=C(C[C@H](NC(=O)OCC2=CC=CC=C2)CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 27.25 g of O-benzyl-N-benzyloxycarbonyltyrosine methyl ester was dissolved in a mixed solvent of 185 ml of ethanol and 122 ml of tetrahydrofuran, and to the solution were added 5.8 g of lithium chloride and 5.2 g of sodium borohydride under ice cooling. The reaction mixture was stirred at a room temperature for 18 hour... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)O.O1CCCC1 | null | 18 | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)OCc1ccccc1>C(C)O.O1CCCC1>O=C(N[C@H](CO)Cc1ccc(OCc2ccccc2)cc1)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4e42a8b5fe4a46378087c9d3b246d21a | CN(C)C=O.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>>COCCOCOc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)OC)cc1 | COC([C@@H](NC(=O)OC(C)(C)C)CC1=CC=C(C=C1)O)=O.[H-].[Na+].CN(C=O)C>>COC([C@@H](NC(=O)OC(C)(C)C)CC1=CC=C(C=C1)OCOCCOC)=O | N([CH3:1])([CH:3]=[O:2])[CH3:6].[CH3:4][C:18]([O:17][C:15]([NH:14][C@@H:13]([CH2:12][c:11]1[cH:10][cH:9][c:8]([OH:7])[cH:27][cH:26]1)[C:22](=[O:23])[O:24][CH3:25])=[O:16])([CH3:19])[CH3:21]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][C@H:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19]... | CN(C)C=O.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C | COCCOCOc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)OC)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | efafa0a6339c75bfa27dc36aebc157a1675075cd6c3754593e740058d44802c9 | ea88b7c6ec4e4769f6c1d2c513fe7a03974fac7a6f46af80ffac0a032d1f27a2 | c1ccccc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[CH3;D1;+0:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12].[CH3;D1;+0:13]-N(-[CH3;D1;+0:14])-[CH;D2;+0:15]=[O;H0;D1;+0:16]>>[#7:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[C;D1;H3:17])-[C;D1;H3:7].[CH3;D1;+0:13]-[O;H0;D2;+0:16]-[CH2;D2... | null | [] | null | null | null | null | 13.39 g of N-tert-butoxycarbonyltyrosine methyl ester was dissolved in 65 ml of tetrahydrofuran and 65 ml of dimethylformamide, and to the solution was added 1.9 g of 60% sodium hydride with stirring in an ice bath. After removing from the ice bath, the mixture was stirred at a room temperature for 30 minutes, and afte... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Aromatic alcohol.Boc | Ether.Ether.Ether.Ether.Boc | null | null | c1ccccc1 | null | O1CCCC1 | null | null | CN(C)C=O.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>O1CCCC1>COCCOCOc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)OC)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6fb0cb4113fb499eb4dfc30867774f34 | O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)OCc1ccccc1.c1ccc(N2CCNCC2)cc1>>O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O.C1(=CC=CC=C1)N1CCNCC1.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N1CCN(CC1)C1=CC=CC=C1 | O[C:13]([C@@H:4]([NH:3][C:2](=[O:1])[O:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1)[CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1)=[O:14].[NH:15]1[CH2:16][CH2:17][N:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH... | O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)OCc1ccccc1.c1ccc(N2CCNCC2)cc1 | O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N[C@@H](Cc1ccccc1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | 58.6 | [{"value": 58.6, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 12.3 g of N-benzyloxycarbonyltyrosine and 6.6 g of N-phenylpiperazine were dissolved in 150 ml of methylene chloride, and to the solution was added 8.4 g of DCC, and the mixture was stirred at a room temperature for 5 hours. Precipitated insoluble matter was filtered off and the filtrate was concentrated under a reduce... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 5 | O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)OCc1ccccc1.c1ccc(N2CCNCC2)cc1>C(Cl)Cl>O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCN(c2ccccc2)CC1)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dfeb66b2e0614f0e93caf3ee661eaf60 | CI.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(c2ccccc2)CC1>>CN([C@@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)C(=O)N1CCN(c2ccccc2)CC1)S(=O)(=O)c1cccc2cnccc12 | O.[H-].[Na+].C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)C(=O)N1CCN(CC1)C1=CC=CC=C1.CI>>C1=NC=CC=2C(=CC=CC12)S(=O)(=O)N([C@@H](CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)C(=O)N1CCN(CC1)C1=CC=CC=C1)C | I[CH3:1].[NH:2]([C@@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH:20][cH:21][c:22]23)[cH:23][cH:24]1)[C:25](=[O:26])[N:27]1[CH2:28][CH2:29][N:30]([c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[CH2:37][CH2:38]1)[S:39](=[O:40])(=[O:41])[c:42]1[cH:43][cH... | CI.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(c2ccccc2)CC1 | CN([C@@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)C(=O)N1CCN(c2ccccc2)CC1)S(=O)(=O)c1cccc2cnccc12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(c2ccccc2)CC1 | I-[CH3;D1;+0:1].[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[C:6](-[C:7])-[NH;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[C:13]>>[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[C:6](-[C:7])-[N;H0;D3;+0:8](-[CH3;D1;+0:1])-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[C:13] | null | [] | null | null | 90 | MINUTE | 2.27 g of the amorphous compound obtained in Example 108 was dissolved in 30 ml of dimethylformamide, to the solution were sequentially added 160 mg of 60% sodium hydride and 0.3 ml of methyl iodide with ice cooling, and the mixture was stirred for 90 minutes with ice cooling. After adding 80 ml of water, the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | c1ccccc1.c1ccc2cnccc2c1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2cnccc2c1 | HI | CN(C=O)C | null | 1.5 | CI.O=C([C@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)NS(=O)(=O)c1cccc2cnccc12)N1CCN(c2ccccc2)CC1>CN(C=O)C>CN([C@@H](Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)C(=O)N1CCN(c2ccccc2)CC1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9210acb815974a8380d54b730e8abe69 | C1CNCCNC1.O=C(Cl)OCc1ccccc1>>O=C(OCc1ccccc1)N1CCCNCC1 | CN(C=O)C.N1CCNCCC1.C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)OC(=O)Cl>>C(C1=CC=CC=C1)OC(=O)N1CCNCCC1 | [NH:11]1[CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1.Cl[C:2](=[O:1])[O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | C1CNCCNC1.O=C(Cl)OCc1ccccc1 | O=C(OCc1ccccc1)N1CCCNCC1 | null | null | O | Protection | N-alkylation of secondary amines with alkyl halides | 466a90f5c0328778671e7ef9d1ad2a8b6e81fdc28f82b2a2f790befcf3020485 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1CCCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#7:5]-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#7:5]-[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:9]-[C:10] | 65.5 | [{"value": 65.5, "product": "C(C1=CC=CC=C1)OC(=O)N1CCNCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 230 ml of dimethylformamide were added 25 g of homopiperazine and 5.4 g of sodium bicarbonate and then 25 ml of water followed by dropwise addition of 10 g of benzyloxycarbonyl chloride with stirring under ice cooling, and the mixture was stirred at a room temperature overnight. After evaporating off dimethylformami... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CNCCNC1 | C1C[NH]CCNC1 | c1ccccc1.C1C[NH]CCNC1 | HCl | O | null | null | C1CNCCNC1.O=C(Cl)OCc1ccccc1>O>O=C(OCc1ccccc1)N1CCCNCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5e959f0c247e4beda9969377311282aa | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.O=C(OCc1ccccc1)N1CCCNCC1>>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCCN(C(=O)OCc2ccccc2)CC1 | C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O.C(C1=CC=CC=C1)OC(=O)N1CCNCCC1.O.ON1N=NC2=C1C=CC=C2.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(=O)N1CCN(CCC1)C([C@@H](NC(=O)OC(C)(C)C)CC1=CC=C(C=C1)O)=O | O[C:18]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1)=[O:19].[NH:20]1[CH2:21][CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[CH2:35][CH2:36]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[... | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.O=C(OCc1ccccc1)N1CCCNCC1 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCCN(C(=O)OCc2ccccc2)CC1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fb7b4c9fc8ef266dfa5161dd684d02bd3bdb61458c00dd0f23100f34a6c5763c | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCc1ccccc1)N1CCCN(C(=O)OCc2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[#7:13]-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]>>[#7:13]-[C:14]-[C:15]-[N;H0;D3;+0:16](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;... | 97.7 | [{"value": 97.7, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CCC1)C([C@@H](NC(=O)OC(C)(C)C)CC1=CC=C(C=C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 15.29 g of N-tert-butoxycarbonyltyrosine and 12.73 g of N-benzyloxycarbonylhomopiperazine were dissolved in 280 ml of tetrahydrofuran, to the solution were added 8.09 g of 1-hydroxybenzotriazole hydrate and 11.77 g of DCC at a room temperature with stirring, and the reaction mixture was stirred for 16 hours. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]C1 | C1C[NH]CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]C1.c1ccccc1 | HO- | O1CCCC1 | null | null | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.O=C(OCc1ccccc1)N1CCCNCC1>O1CCCC1>CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N1CCCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fa570eec38af45bdaa6d75337b1e1aef | O=C(OCc1ccccc1)N1CCCN(C(=O)[C@H](Cc2ccc(OS(=O)(=O)c3cccc4cnccc34)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1>>O=C(OCc1ccccc1)N1CCCN(C(=O)[C@H](Cc2ccc(O)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)OC(=O)N1CCN(CCC1)C([C@@H](NS(=O)(=O)C=1C=2C=CN=CC2C=CC1)CC1=CC=C(C=C1)OS(=O)(=O)C=1C=2C=CN=CC2C=CC1)=O.[OH-].[Na+].C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>C(C1=CC=CC=C1)OC(=O)N1CCN(CCC1)C([C@@H](NS(=O)(=O)C=1C=2C=CN=CC2C=CC1)CC1=CC=C(C=C1)O)=O | O=S(=O)(c1cccc2cnccc12)[O:24][c:23]1[cH:22][cH:21][c:20]([CH2:19][C@@H:18]([C:16]([N:15]2[CH2:14][CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[CH2:42][CH2:41]2)=[O:17])[NH:27][S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][cH:34][c:35]3[cH:36][n:37][cH:38][cH:39][c:40]23)[cH:26][... | O=C(OCc1ccccc1)N1CCCN(C(=O)[C@H](Cc2ccc(OS(=O)(=O)c3cccc4cnccc34)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | O=C(OCc1ccccc1)N1CCCN(C(=O)[C@H](Cc2ccc(O)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | null | null | CO.O1CCCC1 | Reduction | OtherReaction | 8d3501a80697ea4890ac38f15ca267ef68b4b9c0548f46156239e85ec85dc664 | 755d4c7608355ba6558947cede05bc0a8af24b48bc69544e09fcab6bd629384a | O=C(OCc1ccccc1)N1CCCN(C(=O)[C@H](Cc2ccccc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | O=S(=O)(-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4])-c1:c:c:c:c2:c:n:c:c:c:1:2>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 74.7 | [{"value": 74.7, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CCC1)C([C@@H](NS(=O)(=O)C=1C=2C=CN=CC2C=CC1)CC1=CC=C(C=C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.50 g of the amorphous compound obtained in Example 122 was dissolved in 30 ml of methanol and 30 ml of tetrahydrofuran, to the solution was added 60 ml of 1N sodium hydroxide, and the mixture was refluxed for 2 hours and then cooled. The reaction mixture was acidified with citric acid and then alkalized with sodium b... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonate | Aromatic alcohol | c1ccc2cnccc2c1 | null | c1ccccc1.C1C[NH]CC[NH]C1.c1ccccc1.c1ccc2cnccc2c1 | HO- | CO.O1CCCC1 | null | null | O=C(OCc1ccccc1)N1CCCN(C(=O)[C@H](Cc2ccc(OS(=O)(=O)c3cccc4cnccc34)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1>CO.O1CCCC1>O=C(OCc1ccccc1)N1CCCN(C(=O)[C@H](Cc2ccc(O)cc2)NS(=O)(=O)c2cccc3cnccc23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-941e293f0a7c46e8b8635a04d61fecdf | CI.CN(C(Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)CN1CCC2(CC1)OCCO2)S(=O)(=O)c1cccc2cnccc12>>COc1ccc(CC(CN2CCC(=O)CC2)N(C)S(=O)(=O)c2cccc3cnccc23)cc1 | CI.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.O1CCCC1.Cl.C1OC2(CCN(CC2)CC(CC2=CC=C(C=C2)OS(=O)(=O)C=2C=3C=CN=CC3C=CC2)N(S(=O)(=O)C=2C=3C=CN=CC3C=CC2)C)OC1>>COC1=CC=C(CC(CN2CCC(CC2)=O)N(S(=O)(=O)C=2C=3C=CN=CC3C=CC2)C)C=C1 | I[CH3:1].O=S(=O)(c1cccc2cnccc12)[O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH:8]([CH2:9][N:10]2[CH2:11][CH2:12][C:13]3(OCC[O:14]3)[CH2:15][CH2:16]2)[N:17]([CH3:18])[S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][cH:25][c:26]3[cH:27][n:28][cH:29][cH:30][c:31]23)[cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH:8](... | CI.CN(C(Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)CN1CCC2(CC1)OCCO2)S(=O)(=O)c1cccc2cnccc12 | COc1ccc(CC(CN2CCC(=O)CC2)N(C)S(=O)(=O)c2cccc3cnccc23)cc1 | null | null | null | Acylation | OtherReaction | 99d28ed00b31ff0a902f97e2bddd045ff5f84e1e11411b2281454b5217be20b7 | 1691c310bf4574df6a9d9db1231c07fcb5dfb991f04b310ec3830fb6f6e98d3e | O=C1CCN(CC(Cc2ccccc2)NS(=O)(=O)c2cccc3cnccc23)CC1 | C1-C-[O;H0;D2;+0:1]-[C;H0;D4;+0:2]2(-O-1)-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-2.O=S(=O)(-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-c1:c:c:c:c2:c:n:c:c:c:1:2.I-[CH3;D1;+0:12]>>[CH3;D1;+0:12]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11].[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | The amorphous compound obtained in Example 94 was subjected to alkaline hydrolysis, methylation with methyl iodide and potassium carbonate in dimethylformamide/tetrahydrofuran (1:1), and reflux with 3N hydrochloric acid, to obtain N-{1-(p-methoxybenzyl)-2-(4-oxopiperidino)ethyl}-N-methyl-5-isoquinolinesulfonamide in a ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Sulfonate | Ketone.Ether | c1ccc2cnccc2c1.C1CC2(CC[NH]1)OCCO2 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2cnccc2c1 | HI | null | null | null | CI.CN(C(Cc1ccc(OS(=O)(=O)c2cccc3cnccc23)cc1)CN1CCC2(CC1)OCCO2)S(=O)(=O)c1cccc2cnccc12>>COc1ccc(CC(CN2CCC(=O)CC2)N(C)S(=O)(=O)c2cccc3cnccc23)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-18f979271f55488dada415f3d9cd2cc3 | O=C(O)C=Cc1ccc(Cl)cc1>>COC(=O)C=Cc1ccc(Cl)cc1 | ClC1=CC=C(C=CC(=O)O)C=C1.S(O)(O)(=O)=O.C([O-])(O)=O.[Na+]>>ClC1=CC=C(C=CC(=O)OC)C=C1 | [OH:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1 | O=C(O)C=Cc1ccc(Cl)cc1 | COC(=O)C=Cc1ccc(Cl)cc1 | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C:4]=[C:5]-[c:6]>>[C;D1;H3:7]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[C:4]=[C:5]-[c:6] | null | [] | null | null | null | null | 25.9 g of p-chlorocinnamic acid was dissolved in 250 ml of methanol, to the solution was added 1.5 ml of concentrated sulfuric acid, and the mixture was refluxed for 2 hours. The reaction mixture was poured on ice, and the mixture was alkalized with sodium bicarbonate and extracted twice with 1000 ml of chloroform. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | Other | CO | null | null | O=C(O)C=Cc1ccc(Cl)cc1>CO>COC(=O)C=Cc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c09855ed64714736b79c8d5024c94a04 | ClCC=Cc1ccc(Cl)cc1.Nc1ccccc1N>>Nc1ccccc1NCC=Cc1ccc(Cl)cc1 | ClC1=CC=C(C=CCCl)C=C1.C([O-])([O-])=O.[K+].[K+].C1(=C(C=CC=C1)N)N.[Cl-].[Na+]>>ClC1=CC=C(C=CCNC2=C(C=CC=C2)N)C=C1 | Cl[CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH2:8]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | ClCC=Cc1ccc(Cl)cc1.Nc1ccccc1N | Nc1ccccc1NCC=Cc1ccc(Cl)cc1 | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | C(=Cc1ccccc1)CNc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:4]-[C:3]=[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 82.2 | [{"value": 82.2, "product": "ClC1=CC=C(C=CCNC2=C(C=CC=C2)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 19.6 g of 1,2-phenylenediamine was dissolved in 300 ml of dimethylformamide, to the solution were added 11.3 g of the above-prepared 4-chlorocinnamyl chloride crystals and 12.5 g of potassium carbonate at a room temperature with stirring, and the mixture was stirred for 48 hours under the same condition. After adding w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.O | null | null | ClCC=Cc1ccc(Cl)cc1.Nc1ccccc1N>CN(C=O)C.O>Nc1ccccc1NCC=Cc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d4ee0e39c1e94258bf77463d69e44f83 | ClCC=Cc1ccc(Cl)cc1.Nc1cccnc1N>>Nc1ncccc1NCC=Cc1ccc(Cl)cc1 | O.ClC1=CC=C(C=CCCl)C=C1.NC1=NC=CC=C1N.C([O-])([O-])=O.[K+].[K+]>>NC1=NC=CC=C1NCC=CC1=CC=C(C=C1)Cl | Cl[CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[NH2:8]>>[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[NH:8][CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | ClCC=Cc1ccc(Cl)cc1.Nc1cccnc1N | Nc1ncccc1NCC=Cc1ccc(Cl)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | C(=Cc1ccccc1)CNc1cccnc1 | Cl-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4].[N;D1;H2:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[N;D1;H2:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4]):[c:11] | 42.2 | [{"value": 42.2, "product": "NC1=NC=CC=C1NCC=CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 50 | HOUR | 7.71 g of p-chlorocinnamyl chloride and 13.5 g of 2,3-diaminopyridine were dissolved in 220 ml of dimethylformamide, and to the solution was added 8.6 g of potassium carbonate, and the mixture was stirred at a room temperature for 50 hours, and after adding 300 ml of water, extracted twice with 200 ml of chloroform. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1 | HCl | CN(C=O)C | null | 50 | ClCC=Cc1ccc(Cl)cc1.Nc1cccnc1N>CN(C=O)C>Nc1ncccc1NCC=Cc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-06bb6720d27140e6bd8fead9cef0ffdf | CN(C)c1ccccn1.Cl.O=S(=O)(Cl)c1cccc2cnccc12.c1ccncc1>>O=S(=O)(Nc1ncccc1NCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | N1=CC=CC=C1.Cl.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl.CN(C)C1=NC=CC=C1.O>>ClC1=CC=C(C=CCNC=2C(=NC=CC2)NS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1 | [N:4]([c:5]1[n:6][cH:7][cH:8][cH:9][cH:10]1)([CH3:12])[CH3:15].[ClH:19].Cl[S:2](=[O:1])(=[O:3])[c:22]1[cH:23][cH:24][cH:25][c:26]2[cH:27][n:28][cH:29][cH:30][c:31]12.[n:11]1[cH:16][cH:17][cH:18][cH:20][cH:21]1>>[O:1]=[S:2](=[O:3])([NH:4][c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[NH:11][CH2:12][CH:13]=[CH:14][c:15]1[cH:16][cH... | CN(C)c1ccccn1.Cl.O=S(=O)(Cl)c1cccc2cnccc12.c1ccncc1 | O=S(=O)(Nc1ncccc1NCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | null | null | null | C-C Coupling | OtherReaction | e576e93b7dd529fcbe41d45e86cb0e44802fd9459a65fd894839606d16beacf5 | 347c6dd5e9f26f467f6591e9949b355e3b716dcfb02d962314646380ac72c472 | O=S(=O)(Nc1ncccc1NCC=Cc1ccccc1)c1cccc2cnccc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[CH3;D1;+0:7]-[N;H0;D3;+0:8](-[CH3;D1;+0:9])-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1.[ClH;D0;+0:16].[c:17]1:[cH;D2;+0:18]:[n;H0;D2;+0:19]:[cH;D2;+0:20]:[c:21]:[cH;D2;+0:22]:1>>[Cl;H0;D1;+0:16]-[c;H0;D3;+0:22]1:[c:17]:[cH;D2;+0:18]:[c;H0;D3... | null | [] | null | null | 18 | HOUR | 4.52 g of the crystals obtained in Reference Example 41 was dissolved in 50 ml of pyridine, to the solution were added 5.8 g of 5-isoquinolinesulfonyl chloride hydrochloride and 3 g of dimethylaminopyridine, and the mixture was stirred for 18 hours at a room temperature, after adding 150 ml of water, extracted twice wi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Sulfonyl halide | Sulfonamide.Aromatic halide.Secondary amine | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1.c1ccc2cnccc2c1 | HCl | null | null | 18 | CN(C)c1ccccn1.Cl.O=S(=O)(Cl)c1cccc2cnccc12.c1ccncc1>>O=S(=O)(Nc1ncccc1NCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-02666c15032d4a23816abf9f01b6ac87 | COC(=O)c1ccc(N)c(N)c1.ClCC=Cc1ccc(Cl)cc1>>COC(=O)c1ccc(N)c(NCC=Cc2ccc(Cl)cc2)c1 | NC=1C=C(C(=O)OC)C=CC1N.C([O-])([O-])=O.[K+].[K+].ClC1=CC=C(C=CCCl)C=C1>>NC1=C(C=C(C(=O)OC)C=C1)NCC=CC1=CC=C(C=C1)Cl | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([NH2:11])[cH:22]1.Cl[CH2:12][CH:13]=[CH:14][c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([NH:11][CH2:12][CH:13]=[CH:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[cH:22]1 | COC(=O)c1ccc(N)c(N)c1.ClCC=Cc1ccc(Cl)cc1 | COC(=O)c1ccc(N)c(NCC=Cc2ccc(Cl)cc2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | C(=Cc1ccccc1)CNc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:4]-[C:3]=[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 63.2 | [{"value": 63.2, "product": "NC1=C(C=C(C(=O)OC)C=C1)NCC=CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.0 g of methyl 3,4-diaminobenzoate was dissolved in 40 ml of dimethylformamide, and to the solution were added 2.07 g of potassium carbonate and 1.87 g of p-chlorocinnamyl chloride, and reaction was carried out according to the procedure in Reference Example 40, to obtain 2.0 g of the title compound as a light brown o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | null | COC(=O)c1ccc(N)c(N)c1.ClCC=Cc1ccc(Cl)cc1>CN(C=O)C>COC(=O)c1ccc(N)c(NCC=Cc2ccc(Cl)cc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fe25518ea9ed4d34b2044f4a465444f9 | ClCC=Cc1ccccc1.Nc1ccccc1N>>Nc1ccccc1NCC=Cc1ccccc1 | C1(=C(C=CC=C1)N)N.C([O-])([O-])=O.[K+].[K+].C(C=CC1=CC=CC=C1)Cl>>C(C=CC1=CC=CC=C1)NC1=C(C=CC=C1)N | Cl[CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH2:8]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][CH2:9][CH:10]=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | ClCC=Cc1ccccc1.Nc1ccccc1N | Nc1ccccc1NCC=Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | C(=Cc1ccccc1)CNc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:4]-[C:3]=[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 89.5 | [{"value": 89.5, "product": "C(C=CC1=CC=CC=C1)NC1=C(C=CC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 3.24 g of ortho-phenylenediamine was dissolved in 30 ml of dimithylformaide, to the solution were added 2.07 g of potassium carbonate and 1.52 g of cinnamyl chloride, and the mixture was stirred overnight at a room temperature. After adding 100 ml of water, the reaction mixture was extracted twice with 100 ml and 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HCl | O | null | 8 | ClCC=Cc1ccccc1.Nc1ccccc1N>O>Nc1ccccc1NCC=Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-09e583f252ac431594d8cdd55b9396bd | CC(=O)C=Cc1ccc(Cl)cc1.NCCNS(=O)(=O)c1cccc2cnccc12>>CC(=Cc1ccc(Cl)cc1)CNCCNS(=O)(=O)c1cccc2cnccc12 | ClC1=CC=C(C=CC(C)=O)C=C1.NCCNS(=O)(=O)C=1C=2C=CN=CC2C=CC1.CO.[Na]>>ClC1=CC=C(C=C(CNCCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C)C=C1 | O=[C:2]([CH3:1])[CH:11]=[CH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1.[NH2:12][CH2:13][CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][n:25][cH:26][cH:27][c:28]12>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[CH2:11][NH:12][CH2:13][CH2:14][NH:15][S:16](=[O:17... | CC(=O)C=Cc1ccc(Cl)cc1.NCCNS(=O)(=O)c1cccc2cnccc12 | CC(=Cc1ccc(Cl)cc1)CNCCNS(=O)(=O)c1cccc2cnccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=S(=O)(NCCNCC=Cc1ccccc1)c1cccc2cnccc12 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[CH2;D2;+0:3]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 36 | HOUR | 7.30 g of N-(2-aminoethyl)-5-isoquinolinesulfonamide was dissolved in 150 ml of methanol, to the solution was added 6.30 g of p-chlorobenzalacetone, and the mixture was stirred at a room temperature for 36 hours. After addition of 1.32 g of sodium tetrahydrideborate with ice-water cooling, the mixture was stirred for 3... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | Other | null | null | 36 | CC(=O)C=Cc1ccc(Cl)cc1.NCCNS(=O)(=O)c1cccc2cnccc12>>CC(=Cc1ccc(Cl)cc1)CNCCNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-972b7e9615b641608f2fd7c85b62dfc9 | NCCNS(=O)(=O)c1cccc2cnccc12.O=CC=Cc1ccc(Cl)cc1>>O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | C(C)(=O)OCC.ClC1=CC=C(C=CC=O)C=C1.NCCNS(=O)(=O)C=1C=2C=CN=CC2C=CC1.[Na]>>ClC1=CC=C(C=CCNCCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1 | [O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2:6][NH2:7])[c:18]1[cH:19][cH:20][cH:21][c:22]2[cH:23][n:24][cH:25][cH:26][c:27]12.O=[CH:8][CH:9]=[CH:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH:9]=[CH:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[c:18]1... | NCCNS(=O)(=O)c1cccc2cnccc12.O=CC=Cc1ccc(Cl)cc1 | O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=S(=O)(NCCNCC=Cc1ccccc1)c1cccc2cnccc12 | O=[CH;D2;+0:1]-[C:2]=[C:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4] | 71.5 | [{"value": 71.5, "product": "ClC1=CC=C(C=CCNCCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2.01 g of N-(2-aminoethyl]-5-isoquinolinesulfonamide was dissolved in 30 ml of methanol, to the solution was added 1.60 g of p-chlorocinnamaldehyde, and the mixture was stirred for one hour at a room temperature. After an addition of 350 mg of sodium tetrahydrideborate in portions with ice cooling, the mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | Other | CO | null | 1 | NCCNS(=O)(=O)c1cccc2cnccc12.O=CC=Cc1ccc(Cl)cc1>CO>O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-06512ce644cf455d94b7605de32b603b | CI.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>>CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12 | ClC1=CC=C(C=CCNCCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1.CI>>ClC1=CC=C(C=CCN(C)CCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1 | I[CH3:1].[NH:2]([CH2:3][CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13][CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][n:25][cH:26][cH:27][c:28]12>>[CH3:1][N:2]([CH2:3][CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13][CH2:14][NH:15][S:16](=[O:17... | CI.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | O=S(=O)(NCCNCC=Cc1ccccc1)c1cccc2cnccc12 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]=[C:7]-[c:8]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6]=[C:7]-[c:8] | null | [] | null | null | 40 | MINUTE | 1.50 g of the product of Example 172 was dissolved in 10 ml of chloroform, to the solution was added 3 ml of methyl iodide at a room temperature, and the mixture was stirred for 40 minutes. Excess methyl iodide was immediately evaporated off under a reduced pressure, and resulting residue was purified on a silica gel c... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HI | C(Cl)(Cl)Cl | null | 0.666667 | CI.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>C(Cl)(Cl)Cl>CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-57a90189c8764512903a44bb9d37a3a5 | O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>>O=S(=O)(c1cccc2cnccc12)N1CCN(CC=Cc2ccc(Cl)cc2)CC1 | C(C)(=O)OCC.BrCCBr.C([O-])([O-])=O.[K+].[K+].ClC1=CC=C(C=CCNCCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1>>ClC1=CC=C(C=CCN2CCN(CC2)S(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1 | [O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12)[NH:14][CH2:15][CH2:16][NH:17][CH2:18][CH:19]=[CH:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12)[N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH:19... | O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | O=S(=O)(c1cccc2cnccc12)N1CCN(CC=Cc2ccc(Cl)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 1b33cc1f8e92e881af12e0e380d1a778ae5ef329639dfd7cb00ef69fd92a311f | 161c3116a4374afd3332c7fbbdc4c4b8bc038020c5e2de722337ee190caa63bd | O=S(=O)(c1cccc2cnccc12)N1CCN(CC=Cc2ccccc2)CC1 | [O;D1;H0:1]=[#16:2](=[O;D1;H0:3])(-[c:4])-[NH;D2;+0:5]-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]=[C:11]-[c:12]>>[O;D1;H0:1]=[#16:2](=[O;D1;H0:3])(-[c:4])-[N;H0;D3;+0:5]1-[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10]=[C:11]-[c:12])-[C:13]-[C:14]-1 | 25.5 | [{"value": 25.5, "product": "ClC1=CC=C(C=CCN2CCN(CC2)S(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 1.31 g of the product of Example 172 was dissolved in 3 ml of dimethylformamide, to the solution were added 644 mg of 1,2-dibromoethane and 1.13 g of anhydrous potassium carbonate at a room temperature, and the mixture was stirred for 24 hours. After adding 100 ml of ethyl acetate, the ethyl acetate layer was sequentia... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Secondary amine | Tertiary amine.Tertiary amine | null | C1C[NH]CC[NH]1 | c1ccc2cnccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | null | 24 | O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>CN(C=O)C>O=S(=O)(c1cccc2cnccc12)N1CCN(CC=Cc2ccc(Cl)cc2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bdd40074d9ed4c75ae6e98ec6d069c3c | O=CO.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>>O=CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12 | C([O-])([O-])=O.[Na+].[Na+].C(=O)O.C(C)(=O)OC(C)=O.ClC1=CC=C(C=CCNCCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1>>ClC1=CC=C(C=CCN(C=O)CCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1 | O[CH:2]=[O:1].[NH:3]([CH2:4][CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)[CH2:14][CH2:15][NH:16][S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][c:24]2[cH:25][n:26][cH:27][cH:28][c:29]12>>[O:1]=[CH:2][N:3]([CH2:4][CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1)[CH2:14][CH2:15][NH:16][... | O=CO.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | O=CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12 | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=S(=O)(NCCNCC=Cc1ccccc1)c1cccc2cnccc12 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]=[C:8]-[c:9]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[C:6]-[C:7]=[C:8]-[c:9])-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | null | null | 3 ml of formic acid and 3 ml of acetic anhydride were mixed and stirred at a room temperature, and to the mixture was added 1.41 g of the product of Example 172, and the mixture was stirred for one hour. The reaction mixture was added to 50 ml of ethyl acetate and 30 ml of saturated sodium carbonate aqueous solution wi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | C(C)(=O)OCC | null | null | O=CO.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>C(C)(=O)OCC>O=CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ad93cea3c46c4c05874b445fc5c954fd | O=Cc1ccc(O)cc1.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>>O=S(=O)(NCCN(CC=Cc1ccc(Cl)cc1)Cc1ccc(O)cc1)c1cccc2cnccc12 | C(#N)[BH3-].[Na+].ClC1=CC=C(C=CCNCCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1.OC1=CC=C(C=O)C=C1>>ClC1=CC=C(C=CCN(CC2=CC=C(C=C2)O)CCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1 | O=[CH:18][c:19]1[cH:20][cH:21][c:22]([OH:23])[cH:24][cH:25]1.[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH:9]=[CH:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[c:26]1[cH:27][cH:28][cH:29][c:30]2[cH:31][n:32][cH:33][cH:34][c:35]12>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2:6][N:7]([CH2:8][CH:9]=[CH:10][... | O=Cc1ccc(O)cc1.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12 | O=S(=O)(NCCN(CC=Cc1ccc(Cl)cc1)Cc1ccc(O)cc1)c1cccc2cnccc12 | null | C(C)(=O)O | CO | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=S(=O)(NCCN(CC=Cc1ccccc1)Cc1ccccc1)c1cccc2cnccc12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]=[C:10]-[c:11]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9]=[C:10]-[c:11])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 59.3 | [{"value": 59.3, "product": "ClC1=CC=C(C=CCN(CC2=CC=C(C=C2)O)CCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | 0.2 g of the product of Example 172 and 0.13 g of p-hydroxybenzaldehyde were dissolved in 10 ml of methanol, to the solution were added 60 mg of sodium cyanoborohydride and two drops of acetic acid, and the mixture was stirred for 2 days at a room temperature. The reaction mixture was concentrated under a reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2cnccc2c1 | Other | C(C)(=O)O.CO | null | 48 | O=Cc1ccc(O)cc1.O=S(=O)(NCCNCC=Cc1ccc(Cl)cc1)c1cccc2cnccc12>C(C)(=O)O.CO>O=S(=O)(NCCN(CC=Cc1ccc(Cl)cc1)Cc1ccc(O)cc1)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bb0f112c30d04259bcbd03fbf9a0c4bf | CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12.OCCN1CCCCC1>>CN(CC=Cc1ccc(Cl)cc1)CCN(CCN1CCCCC1)S(=O)(=O)c1cccc2cnccc12 | ClC1=CC=C(C=CCN(C)CCNS(=O)(=O)C=2C=3C=CN=CC3C=CC2)C=C1.N1(CCCCC1)CCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC>>ClC1=CC=C(C=CCN(C)CCN(S(=O)(=O)C=2C=3C=CN=CC3C=CC2)CCN2CCCCC2)C=C1 | [CH3:1][N:2]([CH2:3][CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13][CH2:14][NH:15][S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][c:31]2[cH:32][n:33][cH:34][cH:35][c:36]12.O[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][N:2]([CH2:3][CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:... | CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12.OCCN1CCCCC1 | CN(CC=Cc1ccc(Cl)cc1)CCN(CCN1CCCCC1)S(=O)(=O)c1cccc2cnccc12 | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu_sulfonamide | 0bda68210bc1a4edc8064b140a39ccb3ef813b89c5267469bd545dded6906cd4 | 2497efd1dadfa61592e966deb414dc4463866875b7ffd693ba98c7592e2a7ec2 | O=S(=O)(c1cccc2cnccc12)N(CCNCC=Cc1ccccc1)CCN1CCCCC1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5]-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10] | 74.9 | [{"value": 74.9, "product": "ClC1=CC=C(C=CCN(C)CCN(S(=O)(=O)C=2C=3C=CN=CC3C=CC2)CCN2CCCCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.39 g of the amorphous compound obtained in Example 190, 0.145 g of 1-piperidinethanol and 0.369 g of triphenylphosphine in 5 ml of tetrahydrofuran, was added dropwise a solution of 0.245 g of diethyl azodicarboxylate in 2 ml of tetrahydrofuran with stirring under ice cooling. The mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary alcohol | Tertiary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2cnccc2c1 | HO- | C(C)(=O)OCC.O1CCCC1 | null | null | CN(CC=Cc1ccc(Cl)cc1)CCNS(=O)(=O)c1cccc2cnccc12.OCCN1CCCCC1>C(C)(=O)OCC.O1CCCC1>CN(CC=Cc1ccc(Cl)cc1)CCN(CCN1CCCCC1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-98066fc44b1d4119929f1efebf1ad116 | COc1ccc(N)cc1OC.O=S(=O)(Cl)c1cccc2cnccc12>>COc1ccc(NS(=O)(=O)c2cccc3cnccc23)cc1OC | COC=1C=C(N)C=CC1OC.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl.Cl>>COC=1C=C(C=CC1OC)NS(=O)(=O)C=1C=2C=CN=CC2C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:21][c:22]1[O:23][CH3:24].Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][n:17][cH:18][cH:19][c:20]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[cH:21][c:22]1[O... | COc1ccc(N)cc1OC.O=S(=O)(Cl)c1cccc2cnccc12 | COc1ccc(NS(=O)(=O)c2cccc3cnccc23)cc1OC | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cccc2cnccc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 82 | [{"value": 82.0, "product": "COC=1C=C(C=CC1OC)NS(=O)(=O)C=1C=2C=CN=CC2C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 3.06 g of 3,4-dimethoxyaniline was dissolved in 30 ml of pyridine, to the solution was added in small portions 5.28 g of 5-isoquinolinesulfonyl chloride.HCl with stirring under ice cooling, and the mixture was stirred for 30 minutes, and further stirred at a room temperature overnight. After evaporating off the pyridin... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2cnccc2c1 | HCl | N1=CC=CC=C1 | null | 0.5 | COc1ccc(N)cc1OC.O=S(=O)(Cl)c1cccc2cnccc12>N1=CC=CC=C1>COc1ccc(NS(=O)(=O)c2cccc3cnccc23)cc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1bf8d60c367e45b9942d7471cdaae72c | N[C@@H](Cc1ccc(O)c(I)c1)C(=O)O>>N[C@@H](Cc1ccc(O)cc1)C(=O)O | [I-].IC=1C=C(C[C@H](N)C(=O)O)C=CC1O.[I-]>>N[C@@H](CC1=CC=C(C=C1)O)C(=O)O | I[c:9]1[c:7]([OH:8])[cH:6][cH:5][c:4]([CH2:3][C@H:2]([NH2:1])[C:11](=[O:12])[OH:13])[cH:10]1>>[NH2:1][C@@H:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1)[C:11](=[O:12])[OH:13] | N[C@@H](Cc1ccc(O)c(I)c1)C(=O)O | N[C@@H](Cc1ccc(O)cc1)C(=O)O | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6]>>[O;D1;H1:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | Electrolysis was carried out using the same cell, anode, membrane and procedure as in Example 15, except that the pH of the anolyte and catholyte was 7.0. At 85% iodide conversion, the yield of 3-iodo-L-tyrosine was 58% based on initial iodide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | I- | null | null | null | N[C@@H](Cc1ccc(O)c(I)c1)C(=O)O>>N[C@@H](Cc1ccc(O)cc1)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-faa192ddc81149e4a09422705fe2de84 | OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO>>OC[C@H]1O[C@@H]2O[C@H]3[C@H]... | CC(C)CC(C)(C#C)O.C([C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)O)CO)CO)CO)CO)CO)CO)O)O)O>>C([C... | [OH:10][CH2:11][C@H:12]1[O:13][C@@H:14]2[O:15][C@H:16]3[C@H:17]([OH:18])[C@@H:19]([OH:20])[C@@H:21]([O:22][C@H:23]4[C@H:24]([OH:25])[C@@H:26]([OH:27])[C@@H:28]([O:29][C@H:30]5[C@H:31]([OH:32])[C@@H:33]([OH:34])[C@@H:35]([O:36][C@H:37]6[C@H:38]([OH:39])[C@@H:40]([OH:41])[C@@H:42]([O:43][C@H:44]7[C@H:45]([OH:46])[C@@H:47... | OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO | OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1C[C@@H]2OC[C@H]1O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O2 | null | null | [] | null | null | null | null | A mobile slurry is prepared by mixing about 410 g β-cyclodextrin and about 330 g deionized water (distilled water can be used) at about 25° C. in a stainless steel mixing bowl of a KitchenAid mixer using the flat beater mixing attachment. Mixing is continued while about 73 g of Perfume A is added rapidly. The low visco... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[C@@H]2OC[C@H]1O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O[C@@H]1CC[C@@H](CO1)O2 | null | O | null | null | OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO>O>OC[C@H]1O[C@@H]2O[C@H]3[C@H... |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c92cfeae8c76411db9a7c282c6b1f728 | CCOC(=O)Cl.CCOC(=O)[O-].O=C([O-])OC(=O)[O-]>>CCOC(=O)OC(=O)OCC.[Cl-] | [O-]CC.[Na+].C(=O)=O.C(OCC)([O-])=O.[Na+].C(OCC)([O-])=O.[Na+].ClC(=O)OCC.C([O-])(=O)OC(=O)[O-].C([O-])([O-])=O.[Na].C(OCC)([O-])=O.[Na+]>>C(OCC)(=O)OC(=O)OCC.[Cl-].[Na+] | O=C(O[CH2:2][CH3:1])[Cl:12].O=C([O-])[O:9][CH2:10][CH3:11].[O-][C:7]([O:6][C:4]([O-:3])=[O:5])=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].[Cl-:12] | CCOC(=O)Cl.CCOC(=O)[O-].O=C([O-])OC(=O)[O-] | CCOC(=O)OC(=O)OCC.[Cl-] | null | null | C(C)O.C1(=CC=CC=C1)C | Protection | OtherReaction | 264245ef874940b12fcb3c1294ae29c55a27433c0f41cdd2ebe1e2568c0c7f4e | 93477ceed60da179b7bf7e05ad4ca2e1a66efe19a7f7f1f1ff21f2c63be4dd5c | null | O=C(-[Cl;H0;D1;+0:1])-O-[CH2;D2;+0:2]-[C;D1;H3:3].O=C(-[O-])-[O;H0;D2;+0:4]-[C:5]-[C;D1;H3:6].[O-;H0;D1:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C;H0;D3;+0:11](-[O-])=[O;D1;H0:12]>>[C;D1;H3:6]-[C:5]-[O;H0;D2;+0:4]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[#8:10]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:7]-[CH2;D2;+0:2]-[C;D1;H3:3].[Cl-;H0;D0:1] | null | [] | null | null | null | null | The organic pyrocarbonates may be prepared by reacting alkali metal organic carbonate, e.g., sodium ethyl carbonate, with organic halocarbonate, e.g., ethyl chlorocarbonate (ethyl chloroformate). The organo groups of the organic carbonate and halocarbonate are chosen to correspond to the organo groups desired for the p... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Anhydride.Carbonic Acid.Carbonic Acid.Carbonic Acid.Ether.Ether | Anhydride.Carbonic Ester.Carbonic Ester | null | null | null | Other | C(C)O.C1(=CC=CC=C1)C | null | null | CCOC(=O)Cl.CCOC(=O)[O-].O=C([O-])OC(=O)[O-]>C(C)O.C1(=CC=CC=C1)C>CCOC(=O)OC(=O)OCC.[Cl-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-07d855b37c5b4d328abc877c7bed7d1e | CO.N[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O>>CN[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O | Cl.CO.[N+](=O)([O-])C1=CC=C(C[C@H](N)C(=O)O)C=C1>>Cl.CN[C@@H](CC1=CC=C(C=C1)[N+](=O)[O-])C(=O)O | O[CH3:1].[NH2:2][C@@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:14](=[O:15])[OH:16]>>[CH3:1][NH:2][C@@H:3]([CH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1)[C:14](=[O:15])[OH:16] | CO.N[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O | CN[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O | null | null | null | Functional Group Addition | Reductive amination with alcohol | 7444d9f8c0b92d732b04381dfc7993e519351ad9ccf53db7c2f05a0bbe3a2866 | 7ff1f86b220c12721f9df74fb282088506a07c38583ba953e1688baf5ed2ad19 | c1ccccc1 | O-[CH3;D1;+0:1].[C:2]-[C:3](-[NH2;D1;+0:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[C:2]-[C:3](-[NH;D2;+0:4]-[CH3;D1;+0:1])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | null | null | 18 | HOUR | Dry methanol (200 ml) was saturated with HCl(g) in a two-necked round bottom flask cooled to -10° C. p-Nitrophenylalanine (10.0 g, 47.6 mmol) was added in one portion and left to stir for about 18 hours, the solution was evaporated to near dryness on a rotary evaporator and the precipitated product collected in a Buchn... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Methanol | Secondary amine | null | null | c1ccccc1 | HO- | null | null | 18 | CO.N[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O>>CN[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-777c1fb9b65b4cdf9d3f220923205cdd | CC(=O)CN.CC(C)(C)OC(=O)N[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O>>CC(=O)CNC(=O)[C@H](Cc1ccc([N+](=O)[O-])cc1)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)[N+](=O)[O-])C(=O)O.Cl.NCC(C)=O.C(C)N(CC)CC.ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1>>O=C(CNC([C@@H](NC(=O)OC(C)(C)C)CC1=CC=C(C=C1)[N+](=O)[O-])=O)C | [CH3:1][C:2](=[O:3])[CH2:4][NH2:5].O[C:6](=[O:7])[C@H:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1)[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26]>>[CH3:1][C:2](=[O:3])[CH2:4][NH:5][C:6](=[O:7])[C@H:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:... | CC(=O)CN.CC(C)(C)OC(=O)N[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O | CC(=O)CNC(=O)[C@H](Cc1ccc([N+](=O)[O-])cc1)NC(=O)OC(C)(C)C | null | null | C(C)(=O)O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H3:13]-[C:14](=[O;D1;H0:15])-[C:16]-[NH2;D1;+0:17]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+... | null | [] | 0 | CELSIUS | 18 | HOUR | t-Butyloxycarbonyl-p-nitrophenylalanine (4.42 g, 14.26 mmol, aminoacetone hydrochloride (1.56 g, 14.26 mmol), triethylamine (1.44 g, 14.26 mmol), 1-hydroxybenzotriazole (1.69 g, 12.55 mmol), were dissolved in ethyl acetate (400 ml). 1,3-Dicyclohexylcarbodiimide (3.23 g, 15.68 mmol) in ethyl acetate (25 ml) was added an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 0 | 18 | CC(=O)CN.CC(C)(C)OC(=O)N[C@@H](Cc1ccc([N+](=O)[O-])cc1)C(=O)O>C(C)(=O)O.C(C)(=O)OCC>CC(=O)CNC(=O)[C@H](Cc1ccc([N+](=O)[O-])cc1)NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bae6517f0d0c4e2b88dc16d1d8fd4fb6 | Nc1cccc(O)c1.O=C(O)c1ccc(O)cc1C(=O)O>>O=C1c2ccc(O)cc2C(=O)N1c1cccc(O)c1 | NC=1C=C(C=CC1)O.OC=1C=C(C(C(=O)O)=CC1)C(=O)O>>OC=1C=C(C=CC1)N1C(C=2C(C1=O)=CC(=CC2)O)=O | [NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]1.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]1[C:10](O)=[O:11]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]2[C:10](=[O:11])[N:12]1[c:13]1[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]1 | Nc1cccc(O)c1.O=C(O)c1ccc(O)cc1C(=O)O | O=C1c2ccc(O)cc2C(=O)N1c1cccc(O)c1 | null | null | C(C)(=O)O | Acylation | OtherReaction | 03989296fe7fd00d3061010c1aadbbfb4b9eaa9ca91856790fffb1e1bf4b4c50 | b7eb222f11e89f2ccff57aab9a5106ae4173f0ba94ac518e1a9f3b22a378531d | O=C1c2ccccc2C(=O)N1c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](-O)=[O;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:5](:[c:8]):[c:3]-1:[c:4] | 80.5 | [{"value": 80.5, "product": "OC=1C=C(C=CC1)N1C(C=2C(C1=O)=CC(=CC2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | m-Aminophenol(13.23 g, 0.12 mol) and 4-hydroxyphthalic acid (16.98 g, 0.09 mol) are allowed to react in refluxing acetic acid as described above. The product (21.6 g, 91%), collected as a tan solid, is recrystallized from methanol to give 18.5 g of pale yellow powder [mp 270° C. differential scanning calorimetry] havin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | C(C)(=O)O | null | null | Nc1cccc(O)c1.O=C(O)c1ccc(O)cc1C(=O)O>C(C)(=O)O>O=C1c2ccc(O)cc2C(=O)N1c1cccc(O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1a0b05586da349f5b4252b3b31d4054d | BrCCCCCCCCCCBr.CCO.Oc1ccccc1N=Nc1ccccc1>>CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1 | C(C)O.OC1=C(C=CC=C1)N=NC1=CC=CC=C1.BrCCCCCCCCCCBr.[OH-].[K+]>>BrCCCCCCCCCCOC1=CC=C(C=C1)N=NC1=CC=C(C=C1)CCCCCCCCCCCC | Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Br:34].O[CH2:2][CH3:1].[cH:13]1[cH:14][cH:15][c:16]([N:17]=[N:18][c:21]2[cH:20][cH:19][cH:36][cH:35][c:22]2[OH:23])[cH:37][cH:38]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:... | BrCCCCCCCCCCBr.CCO.Oc1ccccc1N=Nc1ccccc1 | CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4b7ce20b118ba61230629b6c5ff630b0850500e59c3985d9d902320e7f981a37 | a753faf74946b378a8f59b3e8d5ca05921b3f037160f49ab6eef7d3286a7016e | c1ccc(N=Nc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].O-[CH2;D2;+0:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c;H0;D3;+0:12]:1-[N;H0;D2;+0:13]=[#7:14]-[c:15]1:[c:16]:[c:17]:[cH;D2;+0:18]:[c:19]:[c:20]:1>>[C:21]-[C:22]-[CH2;D2;+0:4]-[C;D1;H3:5].[C:23]-[C:24]-[c;H0;D3;+0:18]1:[c:17]:[c:16]:[c:15](-[#7:14]=[N;H0;D2;+0:13... | null | [] | null | null | null | null | A 3000 ml three-necked round bottom flask was equipped with magnetic stirring, a heating mantle, a reflux condenser, and a nitrogen atmosphere. The flask was charged with 4-dodecyl-4,-hydroxyazobenzene (60.0 g, 0.164 mol), 1,10-dibromodecane, (66.95 g, 0.223 mol), potassium hydroxide (9.75 g, 0.174 mol), and ethanol (1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Diazene.Primary alcohol.Aromatic alcohol | Ether.Diazene | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | null | null | null | BrCCCCCCCCCCBr.CCO.Oc1ccccc1N=Nc1ccccc1>>CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-45d6e0e571fe4728804424dcef92127c | BrCCCCCCCCCCBr.CCCCCCCCCCCCc1ccc(N=Nc2ccc(O)cc2)cc1>>CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1 | C(CCCCCCCCCCC)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)O.BrCCCCCCCCCCBr.[OH-].[K+]>>BrCCCCCCCCCCOC1=CC=C(C=C1)N=NC1=CC=C(C=C1)CCCCCCCCCCCC | Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Br:34].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([N:17]=[N:18][c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:35][cH:36]2)[cH:37][cH:38]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:... | BrCCCCCCCCCCBr.CCCCCCCCCCCCc1ccc(N=Nc2ccc(O)cc2)cc1 | CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(N=Nc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A 3000 ml three-necked round bottom flask was equipped with magnetic stirring, a heating mantle, a reflux condenser, and a nitrogen atmosphere. The flask was charged with 4-dodecyl-4'-hydroxyazobenzene (60.0 g, 0.164 mol), 1,10-dibromodecane, (66.95 g, 0.223 mol), potassium hydroxide (9.75 g, 0.174 mol), and ethanol (1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)O | null | null | BrCCCCCCCCCCBr.CCCCCCCCCCCCc1ccc(N=Nc2ccc(O)cc2)cc1>C(C)O>CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1d8e39248edc4f098a636d77133a05dd | CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1.CN(C)CCO>>CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCC[N+](C)(C)CCO)cc2)cc1.[Br-] | BrCCCCCCCCCCOC1=CC=C(C=C1)N=NC1=CC=C(C=C1)CCCCCCCCCCCC.CN(CCO)C.O1CCCC1>>[Br-].C(CCCCCCCCCCC)C1=CC=C(C=C1)N=NC1=CC=C(OCCCCCCCCCC[N+](C)(C)CCO)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([N:17]=[N:18][c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Br:44])[cH:40][cH:41]2)[cH:42][cH:43]1.[N:34]([CH3:35])([CH3:36])[CH2:37][CH2... | CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1.CN(C)CCO | CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCC[N+](C)(C)CCO)cc2)cc1.[Br-] | null | null | CO | Functional Group Interconversion | OtherReaction | cf95568d208ea67162a1e8aa2ffc7c679479f5b8aaab2573599ff5258836e869 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(N=Nc2ccccc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[C;D1;H3:9]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[N+;H0;D4:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:6]-[C:5] | null | [] | null | null | 24 | HOUR | A 3000 ml three-necked round bottom flask was equipped with magnetic stirring, a heating mantle, a reflux condenser, and a nitrogen atmosphere. The flask was charged with 4-(10-bromodecyloxy)-4'-dodecylazobenzene (40 g, 0.068 mol), dimethylethanolamine (95.2 g, 1.068 mole) and 1050 ml of tetrahydrofuran. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | null | null | c1ccccc1.c1ccccc1 | null | CO | null | 24 | CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCCBr)cc2)cc1.CN(C)CCO>CO>CCCCCCCCCCCCc1ccc(N=Nc2ccc(OCCCCCCCCCC[N+](C)(C)CCO)cc2)cc1.[Br-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5d63c7e02326475d8934d8f39b40ad49 | Nc1nc(N)nc(N)n1>>Nc1nc(N)nc(N)n1 | N1=C(N)N=C(N)N=C1N.C=O>>C=O.N1=C(N)N=C(N)N=C1N | [NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1>>[NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1 | Nc1nc(N)nc(N)n1 | Nc1nc(N)nc(N)n1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ncncn1 | null | null | [] | 60 | CELSIUS | 30 | MINUTE | Independently, to 31.5 g of melamine were added 52.2 g of 37% aqueous solution of formaldehyde and 170.3 g of distilled water, and the resulting mixture was stirred at 60° C. for 30 minutes to obtain a transparent melamine-formaldehyde precondensate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncncn1 | null | O | 60 | 0.5 | Nc1nc(N)nc(N)n1>O>Nc1nc(N)nc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8640071052634bebb681ae075425f7b2 | CC(C)c1cccc(C(C)C)c1NC(=N)Nc1c(C(C)C)cccc1C(C)C.Cc1cccc(C(Cl)Cl)c1>>CC(C)c1cccc(C(C)C)c1NC(=NCc1cccc(CCl)c1)Nc1c(C(C)C)cccc1C(C)C | C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(=N)NC1=C(C=CC=C1C(C)C)C(C)C.ClC(C1=CC(=CC=C1)C)Cl.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(=NCC1=CC(=CC=C1)CCl)NC1=C(C=CC=C1C(C)C)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[NH:13][C:14](=[NH:15])[NH:25][c:26]1[c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32][cH:33][c:34]1[CH:35]([CH3:36])[CH3:37].Cl[CH:16]([c:17]1[cH:18][cH:19][cH:20][c:21]([CH3:22])[cH:24]1)[Cl:23]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6]... | CC(C)c1cccc(C(C)C)c1NC(=N)Nc1c(C(C)C)cccc1C(C)C.Cc1cccc(C(Cl)Cl)c1 | CC(C)c1cccc(C(C)C)c1NC(=NCc1cccc(CCl)c1)Nc1c(C(C)C)cccc1C(C)C | null | null | C=1(C(=CC=CC1)C)C | Functional Group Interconversion | OtherReaction | 77c4006b61feafdadb38a3464a8de1ee490b61d0da0c13bca01b4c6c32c9e17b | 6057d7fb75624930c9e41a46967dce14902ce53987bcfcd5587c4c1a79bea4df | c1ccc(CN=C(Nc2ccccc2)Nc2ccccc2)cc1 | Cl-[CH;D3;+0:1](-[Cl;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8].[#7:9]-[C:10](-[#7:11])=[NH;D1;+0:12]>>[#7:9]-[C:10](-[#7:11])=[N;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[c:6](-[CH2;D2;+0:7]-[Cl;H0;D1;+0:2]):[c:8] | 32.8 | [{"value": 32.8, "product": "C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(=NCC1=CC(=CC=C1)CCl)NC1=C(C=CC=C1C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 11.4 g (0.03 mole) of N,N'-bis-(2,6-diisopropylphenyl) guanidine, 5.7 g (0.033 mole) of α,α-dichloro-m-xylene and 2.1 g (0.015 mole) of anhydrous potassium carbonate were added to 50 ml of xylene. The thus-formed mixture was then refluxed under heating for 10 hours. After the mixture had been allowed to cool, the insol... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C=1(C(=CC=CC1)C)C | null | null | CC(C)c1cccc(C(C)C)c1NC(=N)Nc1c(C(C)C)cccc1C(C)C.Cc1cccc(C(Cl)Cl)c1>C=1(C(=CC=CC1)C)C>CC(C)c1cccc(C(C)C)c1NC(=NCc1cccc(CCl)c1)Nc1c(C(C)C)cccc1C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da0c1141ff4a4a2e80f2daaa6a47cc27 | CC(C)c1cccc(C(C)C)c1NC(=N)Nc1c(C(C)C)cccc1C(C)C.Cc1ccc(C(Br)Br)cc1>>CC(C)c1cccc(C(C)C)c1NC(=NCc1ccc(CBr)cc1)Nc1c(C(C)C)cccc1C(C)C | C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(=N)NC1=C(C=CC=C1C(C)C)C(C)C.BrC(C1=CC=C(C=C1)C)Br.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(=NCC1=CC=C(C=C1)CBr)NC1=C(C=CC=C1C(C)C)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[NH:13][C:14](=[NH:15])[NH:25][c:26]1[c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32][cH:33][c:34]1[CH:35]([CH3:36])[CH3:37].Br[CH:16]([c:17]1[cH:18][cH:19][c:20]([CH3:21])[cH:23][cH:24]1)[Br:22]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6]... | CC(C)c1cccc(C(C)C)c1NC(=N)Nc1c(C(C)C)cccc1C(C)C.Cc1ccc(C(Br)Br)cc1 | CC(C)c1cccc(C(C)C)c1NC(=NCc1ccc(CBr)cc1)Nc1c(C(C)C)cccc1C(C)C | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 77c4006b61feafdadb38a3464a8de1ee490b61d0da0c13bca01b4c6c32c9e17b | 6057d7fb75624930c9e41a46967dce14902ce53987bcfcd5587c4c1a79bea4df | c1ccc(CN=C(Nc2ccccc2)Nc2ccccc2)cc1 | Br-[CH;D3;+0:1](-[Br;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]:[c:9]:1.[#7:10]-[C:11](-[#7:12])=[NH;D1;+0:13]>>[#7:10]-[C:11](-[#7:12])=[N;H0;D2;+0:13]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:2]):[c:8]:[c:9]:1 | 39.1 | [{"value": 39.1, "product": "C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(=NCC1=CC=C(C=C1)CBr)NC1=C(C=CC=C1C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 11.4 g (0.03 mole) of N,N'-bis-(2,6-diisopropylphenyl) guanidine, 8.7 g (0.03 mole) of α,α-dibromo-p-xylene and 2.1 g (0.015 mole) of anhydrous potassium carbonate were added to 50 ml of toluene. The thus-formed mixture was then refluxed under heating for 10 hours. After the mixture had been allowed to cool, the insolu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C1(=CC=CC=C1)C | null | null | CC(C)c1cccc(C(C)C)c1NC(=N)Nc1c(C(C)C)cccc1C(C)C.Cc1ccc(C(Br)Br)cc1>C1(=CC=CC=C1)C>CC(C)c1cccc(C(C)C)c1NC(=NCc1ccc(CBr)cc1)Nc1c(C(C)C)cccc1C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6fb2d39ee99944cc9f9143eb8ab5677c | CCc1cccc(CC)c1NC(=N)Nc1c(CC)cccc1CC.Cc1cccc(C(Cl)Cl)c1>>CCc1cccc(CC)c1NC(=NCc1cccc(CCl)c1)Nc1c(CC)cccc1CC | C(C)C1=C(C(=CC=C1)CC)NC(=N)NC1=C(C=CC=C1CC)CC.ClC(C1=CC(=CC=C1)C)Cl.C([O-])([O-])=O.[K+].[K+]>>C(C)C1=C(C(=CC=C1)CC)NC(=NCC1=CC(=CC=C1)CCl)NC1=C(C=CC=C1CC)CC | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH3:9])[c:10]1[NH:11][C:12](=[NH:13])[NH:23][c:24]1[c:25]([CH2:26][CH3:27])[cH:28][cH:29][cH:30][c:31]1[CH2:32][CH3:33].Cl[CH:14]([c:15]1[cH:16][cH:17][cH:18][c:19]([CH3:20])[cH:22]1)[Cl:21]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH3:9])[c:10]1[NH:11][C:... | CCc1cccc(CC)c1NC(=N)Nc1c(CC)cccc1CC.Cc1cccc(C(Cl)Cl)c1 | CCc1cccc(CC)c1NC(=NCc1cccc(CCl)c1)Nc1c(CC)cccc1CC | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 77c4006b61feafdadb38a3464a8de1ee490b61d0da0c13bca01b4c6c32c9e17b | 6057d7fb75624930c9e41a46967dce14902ce53987bcfcd5587c4c1a79bea4df | c1ccc(CN=C(Nc2ccccc2)Nc2ccccc2)cc1 | Cl-[CH;D3;+0:1](-[Cl;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8].[#7:9]-[C:10](-[#7:11])=[NH;D1;+0:12]>>[#7:9]-[C:10](-[#7:11])=[N;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[c:6](-[CH2;D2;+0:7]-[Cl;H0;D1;+0:2]):[c:8] | 32.5 | [{"value": 32.5, "product": "C(C)C1=C(C(=CC=C1)CC)NC(=NCC1=CC(=CC=C1)CCl)NC1=C(C=CC=C1CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 9.7 g (0.03 mole) of N,N'-bis-(2,6-diethylphenyl) guanidine, 5.7 g (0.033 mole) of α,α-dichloro-m-xylene and 2.1 g (0.015 mole) of anhydrous potassium carbonate were added to 50 ml of toluene. The thus-formed mixture was then refluxed under heating for 10 hours. After the mixture had been allowed to cool, the insoluble... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | CCc1cccc(CC)c1NC(=N)Nc1c(CC)cccc1CC.Cc1cccc(C(Cl)Cl)c1>C1(=CC=CC=C1)C>CCc1cccc(CC)c1NC(=NCc1cccc(CCl)c1)Nc1c(CC)cccc1CC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6b289f54e6794a3998880c4a3d4f3dbc | Cc1ccc(C(Cl)Cl)cc1.N=C(Nc1ccccc1-c1ccccc1)Nc1ccccc1-c1ccccc1>>ClCc1ccc(CN=C(Nc2ccccc2-c2ccccc2)Nc2ccccc2-c2ccccc2)cc1 | C1(=CC=CC=C1)C1=C(C=CC=C1)NC(=N)NC1=C(C=CC=C1)C1=CC=CC=C1.ClC(C1=CC=C(C=C1)C)Cl.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)C1=C(C=CC=C1)NC(=NCC1=CC=C(C=C1)CCl)NC1=C(C=CC=C1)C1=CC=CC=C1 | Cl[CH:2]([Cl:1])[c:3]1[cH:4][cH:5][c:6]([CH3:7])[cH:36][cH:37]1.[NH:8]=[C:9]([NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[NH:23][c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1-[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[Cl:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]=[C:9... | Cc1ccc(C(Cl)Cl)cc1.N=C(Nc1ccccc1-c1ccccc1)Nc1ccccc1-c1ccccc1 | ClCc1ccc(CN=C(Nc2ccccc2-c2ccccc2)Nc2ccccc2-c2ccccc2)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 3ced70ac43dd5799bc4b89314ebb5482ef8918317df37c036f8f155a8aca8aa0 | 498fc9fa63817756d78172f2f80442d316dac1e36623b01cda3447ffb87955c4 | c1ccc(CN=C(Nc2ccccc2-c2ccccc2)Nc2ccccc2-c2ccccc2)cc1 | Cl-[CH;D3;+0:1](-[Cl;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]:[c:9]:1.[#7:10]-[C:11](-[#7:12])=[NH;D1;+0:13]>>[#7:10]-[C:11](-[#7:12])=[N;H0;D2;+0:13]-[CH2;D2;+0:7]-[c:6]1:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[Cl;D1;H0:2]):[c:9]:[c:8]:1 | 20.6 | [{"value": 20.6, "product": "C1(=CC=CC=C1)C1=C(C=CC=C1)NC(=NCC1=CC=C(C=C1)CCl)NC1=C(C=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10.9 g (0.03 mole) of N,N'-bis-(2-phenylphenyl) guanidine, 5.7 g (0.033 mole) of α,α-dichloro-p-xylene and 2.1 g (0.015 mole) of anhydrous potassium carbonate were added to 50 ml of toluene. The thus-formed mixture was then refluxed under heating for 10 hours. After the mixture had been allowed to cool, the insoluble s... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | Cc1ccc(C(Cl)Cl)cc1.N=C(Nc1ccccc1-c1ccccc1)Nc1ccccc1-c1ccccc1>C1(=CC=CC=C1)C>ClCc1ccc(CN=C(Nc2ccccc2-c2ccccc2)Nc2ccccc2-c2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f252bc5bba1b49918808b53ec81978dd | O=c1ccn(C2OC(COP(=O)(O)OC3C(CO)OC(n4ccc(=O)[nH]c4=O)C3O)C(O)C2O)c(=O)[nH]1>>O=c1[nH]c(=O)c2[nH]c(=O)[nH]c2[nH]1 | CC1=C(C(=O)N(N1C)C=2C=CC=CC2)N.C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OC3C(OC(C3O)N4C=CC(=O)NC4=O)CO)O)O.N>>N1C(=O)NC=2NC(=O)NC2C1=O | O=c1cc[n:7](C2OC(COP(=O)(O)OC3C(CO)OC([n:12]4[c:2](=[O:1])[nH:3][c:4](=[O:5])[cH:6][cH:11]4)C3O)C(O)C2O)[c:8](=[O:9])[nH:10]1>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[c:6]2[nH:7][c:8](=[O:9])[nH:10][c:11]2[nH:12]1 | O=c1ccn(C2OC(COP(=O)(O)OC3C(CO)OC(n4ccc(=O)[nH]c4=O)C3O)C(O)C2O)c(=O)[nH]1 | O=c1[nH]c(=O)c2[nH]c(=O)[nH]c2[nH]1 | null | null | P(=O)([O-])([O-])[O-] | Functional Group Interconversion | OtherReaction | 85ffbf903c3a7a465c7bbb22aef288016ddcce6c379e1317c2e84434d04b76b9 | 6ffcbc09efa9f7952582a4dec70b5e9a5b2c89d9b165136680d1e196c76fddc4 | O=c1[nH]c(=O)c2[nH]c(=O)[nH]c2[nH]1 | O-C-C1-O-C(-[n;H0;D3;+0:1]2:[cH;D2;+0:2]:[cH;D2;+0:3]:[c:4](=[O;D1;H0:5]):[#7;a:6]:[c:7]:2=[O;D1;H0:8])-C(-O)-C-1-O-P(-O)(=O)-O-C-C1-O-C(-[n;H0;D3;+0:9]2:c:c:c(=O):[nH;D2;+0:10]:[c:11]:2=[O;D1;H0:12])-C(-O)-C-1-O>>[O;D1;H0:8]=[c:7]1:[#7;a:6]:[c:4](=[O;D1;H0:5]):[c;H0;D3;+0:3]2:[nH;D2;+0:9]:[c:11](=[O;D1;H0:12]):[nH;D2;... | null | [] | 37 | CELSIUS | null | null | To each of the mixtures was added a reagent prepared by dissolving 1 μmol 4-aminoantipyrine and 2 units of uricase in 1.5 ml of 0.1M phosphate buffer (pH 6.5). After the resulting mixtures were maintained in a thermostat at 37° C. for about 5 minutes, the absorbance was measured at a wavelength of 555 nm with a spectro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | null | c1ncccn1.C1CCOC1.C1CCOC1.c1ccncn1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | P(=O)([O-])([O-])[O-] | 37 | null | O=c1ccn(C2OC(COP(=O)(O)OC3C(CO)OC(n4ccc(=O)[nH]c4=O)C3O)C(O)C2O)c(=O)[nH]1>P(=O)([O-])([O-])[O-]>O=c1[nH]c(=O)c2[nH]c(=O)[nH]c2[nH]1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-de9085482ee942acb56e459381852f84 | O=S(=O)(O)O.[Ga]>>O.O=S(=O)([O-])[O-].O=S(=O)([O-])[O-].O=S(=O)([O-])[O-].[Ga+3].[Ga+3] | [Ga].OS(=O)(=O)O>>O.S(=O)(=O)([O-])[O-].[Ga+3].S(=O)(=O)([O-])[O-].S(=O)(=O)([O-])[O-].[Ga+3] | [OH:1][S:3](=[O:2])(=[O:4])[OH:11].[Ga:17]>>[OH2:1].[O:2]=[S:3](=[O:4])([O-:5])[O-:6].[O:7]=[S:8](=[O:9])([O-:10])[O-:11].[O:12]=[S:13](=[O:14])([O-:15])[O-:16].[Ga+3:17].[Ga+3:18] | O=S(=O)(O)O.[Ga] | O.O=S(=O)([O-])[O-].O=S(=O)([O-])[O-].O=S(=O)([O-])[O-].[Ga+3].[Ga+3] | null | null | C(C)O.O | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | [Ga;H0;D0;+0:1].[O;D1;H0:2]=[S;H0;D4;+0:3](=[O;D1;H0:4])(-[OH;D1;+0:5])-[OH;D1;+0:6]>>[Ga+3;H0;D0:1].[O-;H0;D1:5]-[#16:7](-[O;-;D1;H0:8])(=[O;D1;H0:9])=[O;D1;H0:10].[O;-;D1;H0:11]-[S;H0;D4;+0:3](-[O;-;D1;H0:12])(=[O;D1;H0:2])=[O;D1;H0:4].[OH2;D0;+0:6] | null | [] | null | null | null | null | 4.1 g of gallium sulphate hydrate (the H2O/Ga2 (SO4)3 molar ratio is close to 25) are dissolved in 3.7 g of distilled water. The sulphate is obtained by dissolving gallium (Grade 1 from Johnson Matthey) in hot concentrated H2SO4, in excess, taking up the suspension obtained in ethanol at a concentration of 60% in water... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | C(C)O.O | null | null | O=S(=O)(O)O.[Ga]>C(C)O.O>O.O=S(=O)([O-])[O-].O=S(=O)([O-])[O-].O=S(=O)([O-])[O-].[Ga+3].[Ga+3] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6c9c4dc14ecb42679eca1006ffa0ee05 | [Al+3].[Mg+2]>>[Al+3].[Mg+2] | P(=O)([O-])([O-])[O-].[NH4+].[NH4+].[NH4+].[N+](=O)([O-])[O-].[Al+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[Cl-].[Mg+2].[Cl-].[OH-].[NH4+].Cl[Ti](Cl)(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>>P(=O)([O-])([O-])[O-].[Mg+2].[Al+3].Cl[Ti](Cl)(Cl)Cl | [Al+3:6].[Mg+2:12]>>[Al+3:6].[Mg+2:12] | [Al+3].[Mg+2] | [Al+3].[Mg+2] | null | null | CCCCCCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | A series of catalysts comprising TiCl4 and a particulate cogelled xerogel of aluminum-magnesium phosphate was prepared at a pH of about 6-10 by combining aqueous solutions of aluminum nitrate, magnesium chloride, monobasic ammonium phosphate and ammonium hydroxide. Generally, each catalyst was made by slurrying the gel... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCCCCCC | null | null | [Al+3].[Mg+2]>CCCCCCC>[Al+3].[Mg+2] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e4e95021117a431db55e0845d2ecf3fd | Cc1ccccc1S(=O)(=O)N=C=O.Nc1ccccc1>>Cc1ccc(S(=O)(=O)NC(=O)Nc2ccccc2)cc1 | NC1=CC=CC=C1.NC1=CC=CC=C1.C1(=CC=CC=C1)C.C=1(C(=CC=CC1)S(=O)(=O)N=C=O)C>>C1(=CC=C(C=C1)S(=O)(=O)NC(=O)NC1=CC=CC=C1)C | [CH3:1][c:2]1[c:5]([S:6](=[O:7])(=[O:8])[N:9]=[C:10]=[O:11])[cH:4][cH:3][cH:19][cH:20]1.[NH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10](=[O:11])[NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | Cc1ccccc1S(=O)(=O)N=C=O.Nc1ccccc1 | Cc1ccc(S(=O)(=O)NC(=O)Nc2ccccc2)cc1 | null | null | null | Acylation | OtherReaction | 8dc8740a6cf6305b28543404dca4a41e9db54610b035fd636d4198fbeab524f4 | 24cba6b128cf13377717dc3857354238fb483e0cd1cd012e69813867b2abb802 | O=C(Nc1ccccc1)NS(=O)(=O)c1ccccc1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:[c;H0;D3;+0:7]:1-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13].[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[c;H0;D3;+0:7](-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[NH;D2;+0:11]-[C... | null | [] | 90 | CELSIUS | null | null | A three-necked flask equipped with a dropping funnel, a thermometer, and a reflux condenser was charged with 18.6 g of aniline and the aniline was dissolved in 200 ml of toluene. While the resultant reaction solution was stirred with a magnetic stirrer, 42.0 g of toluenesulfonylisocyanate were added dropwise from the d... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Tosylate.Urea | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | 90 | null | Cc1ccccc1S(=O)(=O)N=C=O.Nc1ccccc1>>Cc1ccc(S(=O)(=O)NC(=O)Nc2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-07d878beecdd42a5b96e75782c8b11ad | COC(=O)CBr.COc1ccc2c(c1)C(N)CCC2>>COC(=O)CNC1CCCc2ccc(OC)cc21 | NC1CCCC2=CC=C(C=C12)OC.COC(CBr)=O>>COC(CNC1CCCC2=CC=C(C=C12)OC)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][c:18]21>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:7]1[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][c:18]21 | COC(=O)CBr.COc1ccc2c(c1)C(N)CCC2 | COC(=O)CNC1CCCc2ccc(OC)cc21 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 308780347cfd56717124ea78bf2bc5de380db774d7ce948246e279dfd7d8998b | d2327a8d30a39f085182e5e2f77f5b022ac99c077866b86103acfec639a8f73d | c1ccc2c(c1)CCCC2 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:9] | null | [] | null | null | 70 | HOUR | 367.0 g of 1-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene are solved in 1500 ml of diethyl ether. To this solution is dropwise added a solution of 158.3 g of bromoacetic acid methyl ester in 450 ml of diethyl ether. The mixture is stirred at room temperature for 70 hours. The precipitate is separated and the solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccc2c(c1)CCCC2 | HBr | C(C)OCC | null | 70 | COC(=O)CBr.COc1ccc2c(c1)C(N)CCC2>C(C)OCC>COC(=O)CNC1CCCc2ccc(OC)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d331a1f9455242ecbaaee3d7cbdb816e | CC(=O)OC(C)=O.COC(=O)CNC1CCCc2ccc(OC)cc21>>COC(=O)CN(C=O)C1CCCc2ccc(OC)cc21 | COC(CNC1CCCC2=CC=C(C=C12)OC)=O.C(C)(=O)OC(C)=O>>COC(CN(C1CCCC2=CC=C(C=C12)OC)C=O)=O | CC(=O)O[C:7](C)=[O:8].[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]21>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]([CH:7]=[O:8])[CH:9]1[CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]21 | CC(=O)OC(C)=O.COC(=O)CNC1CCCc2ccc(OC)cc21 | COC(=O)CN(C=O)C1CCCc2ccc(OC)cc21 | null | null | C(=O)O | Acylation | OtherReaction | 72a6d1966b6b15ac7195d4682af251dc9ffac857f784a4242970ab5c7a529369 | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | c1ccc2c(c1)CCCC2 | C-C(=O)-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[C:4](-[NH;D2;+0:5]-[C:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[c:11]>>[C:3]-[C:4](-[N;H0;D3;+0:5](-[C:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[CH;D2;+0:1]=[O;D1;H0:2])-[c:11] | 101.1 | [{"value": 97.0, "product": "COC(CN(C1CCCC2=CC=C(C=C12)OC)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.1, "product": "COC(CN(C1CCCC2=CC=C(C=C12)OC)C=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 70 | HOUR | 2.40 g of N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)glycine methyl ester are added dropwise with cooling to 5° C. to 5.52 g of formic acid. Additionally 1.79 g of acetic anhydride are added, and the mixture is kept at room temperature for 70 hours. Destillation under vacuum affords 2.7 g (97% of theory) of N-formy... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | null | null | c1ccc2c(c1)CCCC2 | HO- | C(=O)O | null | 70 | CC(=O)OC(C)=O.COC(=O)CNC1CCCc2ccc(OC)cc21>C(=O)O>COC(=O)CN(C=O)C1CCCc2ccc(OC)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7700c29acc3b4bd1902fd09ff1183544 | COC(=O)C(C=O)N(C=O)C1CCCc2ccccc21.[NH4+]>>COC(=O)c1cncn1C1CCCc2ccccc21 | C([O-])([O-])=O.[NH4+].[NH4+].COC(C(N(C1CCCC2=CC=CC=C12)C=O)C=O)=O>>COC(=O)C1=CN=CN1C1CCCC2=CC=CC=C12 | O=[CH:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[N:9]([CH:8]=O)[CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21.[NH4+:7]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | COC(=O)C(C=O)N(C=O)C1CCCc2ccccc21.[NH4+] | COC(=O)c1cncn1C1CCCc2ccccc21 | null | null | C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | OtherReaction | 1a481ad88f8384c14db36618e609a6265b383027caf03124ea737d7c71ca43d1 | 33a99fda60914bd5ae296afe9e7947aa8e075ab24e2116a7c1687ab31c7abbeb | c1ccc2c(c1)CCCC2n1ccnc1 | O=[CH;D2;+0:1]-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[N;H0;D3;+0:7](-[CH;D2;+0:8]=O)-[C:9](-[C:10])-[c:11].[NH4+;D0:12]>>[C:10]-[C:9](-[n;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D2;+0:12]:[cH;D2;+0:1]:[c;H0;D3;+0:2]:1-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[c:11] | null | [] | 70 | CELSIUS | null | null | 33.0 g of ammonium carbonate are added at room temperature to a solution of 15.5 g of N,α-bis-formyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)glycine methyl ester in 300 ml of xylene. The mixture is heated to 70° C. for 1 hour then the temperature is raised to 120° C. for 3 hours. After concentration the 1-(1,2,3,4-tetrahy... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Tertiary amide | Ester | null | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2c(c1)CCCC2 | HO- | C=1(C(=CC=CC1)C)C | 70 | null | COC(=O)C(C=O)N(C=O)C1CCCc2ccccc21.[NH4+]>C=1(C(=CC=CC1)C)C>COC(=O)c1cncn1C1CCCc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f57d7a6d780c4a4a823cce69c82616b4 | COC(=O)C(C=O)N(C=O)C1CCCc2ccccc21.[NH4+]>>COC(=O)c1cncn1C1CCCc2ccccc21 | C(C)(=O)[O-].[NH4+].COC(C(N(C1CCCC2=CC=CC=C12)C=O)C=O)=O.C(C)(=O)[O-].[NH4+].C(C)(=O)O>>COC(=O)C1=CN=CN1C1CCCC2=CC=CC=C12 | O=[CH:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[N:9]([CH:8]=O)[CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21.[NH4+:7]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | COC(=O)C(C=O)N(C=O)C1CCCc2ccccc21.[NH4+] | COC(=O)c1cncn1C1CCCc2ccccc21 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 1a481ad88f8384c14db36618e609a6265b383027caf03124ea737d7c71ca43d1 | 33a99fda60914bd5ae296afe9e7947aa8e075ab24e2116a7c1687ab31c7abbeb | c1ccc2c(c1)CCCC2n1ccnc1 | O=[CH;D2;+0:1]-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[N;H0;D3;+0:7](-[CH;D2;+0:8]=O)-[C:9](-[C:10])-[c:11].[NH4+;D0:12]>>[C:10]-[C:9](-[n;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D2;+0:12]:[cH;D2;+0:1]:[c;H0;D3;+0:2]:1-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[c:11] | null | [] | null | null | 4 | HOUR | A mixture of 16.5 g of N,α-bis-formyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl) glycine methyl ester, 65.0 g of ammonium acetate and 100 ml of acetic acid are refluxed for 8 hours. Then additional 50 g ammonium acetate are added and the refluxing is continued for further 4 hours. The solution is diluted with 300 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Tertiary amide | Ester | null | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2c(c1)CCCC2 | HO- | O | null | 4 | COC(=O)C(C=O)N(C=O)C1CCCc2ccccc21.[NH4+]>O>COC(=O)c1cncn1C1CCCc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-803d1399dfd7461184d0632b8742a4e8 | CC1(C)CCc2ccccc2C1N.COC(=O)CBr>>COC(=O)CNC1c2ccccc2CCC1(C)C | NC1C(CCC2=CC=CC=C12)(C)C.COC(CBr)=O>>COC(CNC1C(CCC2=CC=CC=C12)(C)C)=O | [NH2:6][CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14][CH2:15][C:16]1([CH3:17])[CH3:18].Br[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14][CH2:15][C:16]1([CH3:17])[CH3:18] | CC1(C)CCc2ccccc2C1N.COC(=O)CBr | COC(=O)CNC1c2ccccc2CCC1(C)C | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 308780347cfd56717124ea78bf2bc5de380db774d7ce948246e279dfd7d8998b | d2327a8d30a39f085182e5e2f77f5b022ac99c077866b86103acfec639a8f73d | c1ccc2c(c1)CCCC2 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:9] | null | [] | null | null | 70 | HOUR | 65.2 g of 1-amino-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene are solved in 250 ml of diethyl ether. To this solution is dropwise added a solution of 28.5 g of bromoacetic acid methyl ester in 150 ml of diethyl ether. The mixture is stirred at room temperature for 70 hours. The precipitate is separated and the solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccc2c(c1)CCCC2 | HBr | C(C)OCC | null | 70 | CC1(C)CCc2ccccc2C1N.COC(=O)CBr>C(C)OCC>COC(=O)CNC1c2ccccc2CCC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-16ccefa01c1e42bcac9d0c141776cc38 | CC(=O)OC(C)=O.COC(=O)CNC1c2ccccc2CCC1(C)C>>COC(=O)CN(C=O)C1c2ccccc2CCC1(C)C | COC(CNC1C(CCC2=CC=CC=C12)(C)C)=O.C(C)(=O)OC(C)=O>>COC(CN(C1C(CCC2=CC=CC=C12)(C)C)C=O)=O | CC(=O)O[C:7](C)=[O:8].[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[CH2:16][CH2:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]([CH:7]=[O:8])[CH:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[CH2:16][CH2:17][C:18]1([CH3:19])[CH3:20] | CC(=O)OC(C)=O.COC(=O)CNC1c2ccccc2CCC1(C)C | COC(=O)CN(C=O)C1c2ccccc2CCC1(C)C | null | null | C(=O)O | Acylation | OtherReaction | 72a6d1966b6b15ac7195d4682af251dc9ffac857f784a4242970ab5c7a529369 | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | c1ccc2c(c1)CCCC2 | C-C(=O)-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[C:4](-[NH;D2;+0:5]-[C:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[c:11]>>[C:3]-[C:4](-[N;H0;D3;+0:5](-[C:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[CH;D2;+0:1]=[O;D1;H0:2])-[c:11] | null | [] | null | null | 70 | HOUR | The complete yield of N-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)glycine methyl ester of the process a) is added dropwise with cooling to 5° C. to 67.8 ml of formic acid. Additionally 24.9 ml of acetic anhydride are added, and the mixture is kept at room temperature for 70 hours. Destillation under vacuum afford... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | null | null | c1ccc2c(c1)CCCC2 | HO- | C(=O)O | null | 70 | CC(=O)OC(C)=O.COC(=O)CNC1c2ccccc2CCC1(C)C>C(=O)O>COC(=O)CN(C=O)C1c2ccccc2CCC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-90f241a6026441e4b5bbd36ef857d8ed | CC(=O)OC(C)=O.COC(=O)CNC1c2ccccc2CC1(C)C>>COC(=O)CN(C=O)C1c2ccccc2CC1(C)C | COC(CNC1C(CC2=CC=CC=C12)(C)C)=O.C(C)(=O)OC(C)=O>>COC(CN(C1C(CC2=CC=CC=C12)(C)C)C=O)=O | CC(=O)O[C:7](C)=[O:8].[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[CH2:16][C:17]1([CH3:18])[CH3:19]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]([CH:7]=[O:8])[CH:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[CH2:16][C:17]1([CH3:18])[CH3:19] | CC(=O)OC(C)=O.COC(=O)CNC1c2ccccc2CC1(C)C | COC(=O)CN(C=O)C1c2ccccc2CC1(C)C | null | null | C(=O)O | Acylation | OtherReaction | 72a6d1966b6b15ac7195d4682af251dc9ffac857f784a4242970ab5c7a529369 | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | c1ccc2c(c1)CCC2 | C-C(=O)-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[C:4](-[NH;D2;+0:5]-[C:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[c:11]>>[C:3]-[C:4](-[N;H0;D3;+0:5](-[C:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[CH;D2;+0:1]=[O;D1;H0:2])-[c:11] | null | [] | null | null | 18.5 | HOUR | 936 g of N-(2,2-dimethyl-indan-1-yl)glycine methyl ester are added dropwise with cooling to 5° C. to 1817 ml of formic acid. Additionally 664 ml of acetic anhydride are added, and the mixture is kept at room temperature for 18.5 hours. Destillation under vacuum affords 1015 g of N-formyl-N-(2,2-dimethyl-indan-1-yl)glyc... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | null | null | c1ccc2c(c1)CCC2 | HO- | C(=O)O | null | 18.5 | CC(=O)OC(C)=O.COC(=O)CNC1c2ccccc2CC1(C)C>C(=O)O>COC(=O)CN(C=O)C1c2ccccc2CC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-13f80b85ece745a599e02367384e39e8 | COC(=O)c1cnc(S)n1C1c2ccccc2CC1(C)C>>COC(=O)c1cncn1C1c2ccccc2CC1(C)C | [OH-].[Na+].N(=O)[O-].[Na+].[N+](=O)(O)[O-].COC(=O)C1=CN=C(N1C1C(CC2=CC=CC=C12)(C)C)S>>COC(=O)C1=CN=CN1C1C(CC2=CC=CC=C12)(C)C | S[c:8]1[n:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][C:18]1([CH3:19])[CH3:20]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][C:18]1([CH3:19])[CH3:20] | COC(=O)c1cnc(S)n1C1c2ccccc2CC1(C)C | COC(=O)c1cncn1C1c2ccccc2CC1(C)C | null | null | O | Reduction | OtherReaction | eae27167089e95faf7ce5ed478321b2a0cf6e27101b71987c0c66ed8073c81f6 | 6dfa579c3c25232785e7dcb34dfc1e7688e0474e6615711d0e6a05188bc6f710 | c1ccc2c(c1)CCC2n1ccnc1 | S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#7;a:8]:1-[C:9]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:3]:[#7;a:2]:[cH;D2;+0:1]:[#7;a:8]:1-[C:9] | 96.7 | [{"value": 96.7, "product": "COC(=O)C1=CN=CN1C1C(CC2=CC=CC=C12)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 2 g of sodium nitrite and 17.4 ml of nitric acid are solved in 140 ml of deionisized water. Within 20 min. 28 g of 1-(2,2-dimethyl-indan-1-yl)-2-mercapto-5-imidazolecarboxylic acid methyl ester are added portionwise at a temperature between 30° C. and 50° C. The reaction mixture is treated with conc. aqueous sodium hyd... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2c(c1)CCC2 | Other | O | null | 0.333333 | COC(=O)c1cnc(S)n1C1c2ccccc2CC1(C)C>O>COC(=O)c1cncn1C1c2ccccc2CC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37a0638f1dc84d4298b53e5aaef50245 | COC(=O)c1cncn1C1c2ccccc2CCC1(C)C.[OH-]>>COC(=O)c1cncn1C1c2ccccc2C(=O)CC1(C)C | COC(=O)C1=CN=CN1C1C(CCC2=CC=CC=C12)(C)C.[OH-].[Na+]>>COC(=O)C1=CN=CN1C1C(CC(C2=CC=CC=C12)=O)(C)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][CH2:19][C:20]1([CH3:21])[CH3:22].[OH-:18]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17](=[O:18])[CH2:19][C:20]1([CH3:21])[CH3:22] | COC(=O)c1cncn1C1c2ccccc2CCC1(C)C.[OH-] | COC(=O)c1cncn1C1c2ccccc2C(=O)CC1(C)C | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 17ac1d8e8ffb91d08f39e971f0bcfc22ee244df26ff57dd988bb7232a176ede7 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C1CCC(n2ccnc2)c2ccccc21 | [C:1]-[C:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6].[OH-;D0:7]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:7])-[c:4](:[c:5]):[c:6] | 28.2 | [{"value": 28.2, "product": "COC(=O)C1=CN=CN1C1C(CC(C2=CC=CC=C12)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 142 g of 1-(2,2-dimethyl-tetralin-1-yl)-5-imidazolecarboxylic acid methyl ester are dispersed in 1 liter of deionisized water. The suspension is heated to +87° C., and within a period of 1.5 hours a total of 335 g of ammoniaperoxodisulfate is added portionwise in such a manner, that the temperature does not exceed +90°... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1c[nH]cn1.c1ccc2c(c1)CCCC2 | null | O | null | null | COC(=O)c1cncn1C1c2ccccc2CCC1(C)C.[OH-]>O>COC(=O)c1cncn1C1c2ccccc2C(=O)CC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d340505be6cf4a148cb1322f1bc7b740 | CC1(C)C(=O)N(Br)C(=O)N1Br.COC(=O)c1cncn1C1c2ccccc2CCC1(C)C>>COC(=O)c1cncn1C1c2ccccc2C(Br)=CC1(C)C | COC(=O)C1=CN=CN1C1C(CCC2=CC=CC=C12)(C)C.BrN1C(=O)N(C(=O)C1(C)C)Br>>COC(=O)C1=CN=CN1C1C(C=C(C2=CC=CC=C12)Br)(C)C | CC1(C)C(=O)N(Br)C(=O)N1[Br:18].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][CH2:19][C:20]1([CH3:21])[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]([Br:18])=[CH:19][C:20]1([CH3:21... | CC1(C)C(=O)N(Br)C(=O)N1Br.COC(=O)c1cncn1C1c2ccccc2CCC1(C)C | COC(=O)c1cncn1C1c2ccccc2C(Br)=CC1(C)C | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | e505f7c41876ffbb88c042e3c5c1b11785785d2fa8ff6a1328717c49a2b88c29 | 17cbffb6a81e2a92eac972329bd87d2c6ed7c1b3f29193aa2663709d2f8ac83f | C1=Cc2ccccc2C(n2ccnc2)C1 | Br-N1-C(=O)-N(-[Br;H0;D1;+0:1])-C(-C)(-C)-C-1=O.[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[C:5]-[c:6]:[c:7](:[c:8])-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1>>[Br;H0;D1;+0:1]-[C;H0;D3;+0:9]1=[CH;D2;+0:10]-[C:3](-[C;D1;H3:2])(-[C;D1;H3:4])-[C:5]-[c:6]:[c:7]-1:[c:8] | 51.9 | [{"value": 51.9, "product": "COC(=O)C1=CN=CN1C1C(C=C(C2=CC=CC=C12)Br)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8.5 g of 1-(2,2-dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester in 100 ml of carbon tetrachloride is treated with 8.6 g of 1,3-dibromo-5,5-dimethylhydantoin and heated to reflux for 1 hour, while the reaction vessel is exposed to a 100W-irradiation lamp. The mixture is cooled to room temper... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Tertiary amide | Alkenyl halide | C1CNCN1.c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | c1c[nH]cn1.C1=Cc2ccccc2CC1 | HBr | C(Cl)(Cl)(Cl)Cl | null | null | CC1(C)C(=O)N(Br)C(=O)N1Br.COC(=O)c1cncn1C1c2ccccc2CCC1(C)C>C(Cl)(Cl)(Cl)Cl>COC(=O)c1cncn1C1c2ccccc2C(Br)=CC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5e6d61be575e48c1b3148f75190618fb | COC(=O)c1cncn1C1c2ccccc2CC1(C)C.O=S(=O)(O)O>>COC(=O)c1cncn1C1c2ccccc2C(=O)C1(C)C | [OH-].[Na+].COC(=O)C1=CN=CN1C1C(CC2=CC=CC=C12)(C)C.S(O)(O)(=O)=O>>COC(=O)C1=CN=CN1C1C(C(C2=CC=CC=C12)=O)(C)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][C:19]1([CH3:20])[CH3:21].O=S(O)(O)=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17](=[O:18])[C:19]1([CH3:20])[CH3:21] | COC(=O)c1cncn1C1c2ccccc2CC1(C)C.O=S(=O)(O)O | COC(=O)c1cncn1C1c2ccccc2C(=O)C1(C)C | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 32ab24ed955b97edb4307c2f3e4046b88d7a3304f9d6f8e3f49a6ef57e022b90 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C1CC(n2ccnc2)c2ccccc21 | O-S(-O)(=O)=[O;H0;D1;+0:1].[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[C:5]-[c:6]:[c:7](:[c:8])-[CH2;D2;+0:9]-1>>[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[C:5]-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:1] | 60.2 | [{"value": 60.2, "product": "COC(=O)C1=CN=CN1C1C(C(C2=CC=CC=C12)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 30 g of 1-(2,2-dimethyl-indan-1-yl)-5-imidazolecarboxylic acid methyl ester, 150 ml of water and 17 g of sulfuric acid is heated to +80° C. Within a period of 1.5 hours an aqueous solution of 114 g of ammoniaperoxodisulfate is added dropwise. The reaction mixture is cooled to +7° C. and the pH-value is adj... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1c[nH]cn1.c1ccc2c(c1)CCC2 | HO- | O | null | null | COC(=O)c1cncn1C1c2ccccc2CC1(C)C.O=S(=O)(O)O>O>COC(=O)c1cncn1C1c2ccccc2C(=O)C1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-48e222cb04ad453db4f252afa1c90d91 | COC(=O)c1cncn1C1c2ccccc2C(=O)C1(C)C.FS(F)(F)F>>COC(=O)c1cncn1C1c2ccccc2C(F)(F)C1(C)C | COC(=O)C1=CN=CN1C1C(C(C2=CC=CC=C12)=O)(C)C.S(F)(F)(F)F.F>>COC(=O)C1=CN=CN1C1C(C(C2=CC=CC=C12)(F)F)(C)C | O=[C:17]1[c:16]2[c:11]([cH:12][cH:13][cH:14][cH:15]2)[CH:10]([n:9]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][n:7][cH:8]2)[C:20]1([CH3:21])[CH3:22].FS(F)([F:18])[F:19]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]([F:18])([F:19])[C:20]1([CH3:21])[CH3:22] | COC(=O)c1cncn1C1c2ccccc2C(=O)C1(C)C.FS(F)(F)F | COC(=O)c1cncn1C1c2ccccc2C(F)(F)C1(C)C | null | null | null | Functional Group Interconversion | OtherReaction | c04761b116f8f1d87ea7ec401f8b69cf89b1bacf0f356541b04c249a65ea80ad | 2296f264e64b8bfbfcbc70726e7ebb990eb0ff1d1f55dd16887952425668883a | c1ccc2c(c1)CCC2n1ccnc1 | F-S(-F)(-[F;H0;D1;+0:1])-[F;H0;D1;+0:2].O=[C;H0;D3;+0:3]1-[c:4](:[c:5]):[c:6]-[C:7]-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[C:8]1(-[C;D1;H3:10])-[C:7]-[c:6]:[c:4](:[c:5])-[C;H0;D4;+0:3]-1(-[F;H0;D1;+0:1])-[F;H0;D1;+0:2] | 68.4 | [{"value": 68.4, "product": "COC(=O)C1=CN=CN1C1C(C(C2=CC=CC=C12)(F)F)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 11.4 g of 1-(2,2-dimethyl-3-oxo-indan-1-yl)-5-imidazolecarboxylic acid methyl ester, 43 g of sulfur tetrafluoride and 160 g of hydrogen fluoride is heated for 24 hours to +50° C. in an acid-resistant autoclave. The pressure is about 7 bars. The unreacted hydrogen fluoride is removed and the residue is take... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary halide.Tertiary halide | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1c[nH]cn1.c1ccc2c(c1)CCC2 | Other | null | null | null | COC(=O)c1cncn1C1c2ccccc2C(=O)C1(C)C.FS(F)(F)F>>COC(=O)c1cncn1C1c2ccccc2C(F)(F)C1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-65d806fc62d34034938ca2f29c783c94 | CI.CI.O=C1CCc2c(Cl)cccc21>>CC1(C)Cc2c(Cl)cccc2C1=O | [OH-].[K+].ClC1=C2CCC(C2=CC=C1)=O.CI.CN(C=O)C.O.CI>>CC1(C(C2=CC=CC(=C2C1)Cl)=O)C | I[CH3:1].I[CH3:3].[CH2:2]1[CH2:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]2[C:12]1=[O:13]>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]2[C:12]1=[O:13] | CI.CI.O=C1CCc2c(Cl)cccc21 | CC1(C)Cc2c(Cl)cccc2C1=O | null | null | null | C-C Coupling | OtherReaction | 05f10ef4d1ab771e97c7b7be0989d91b62b233a8c3db90531562574485d68797 | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1CCc2ccccc21 | I-[CH3;D1;+0:1].I-[CH3;D1;+0:2].[O;D1;H0:3]=[C:4]1-[CH2;D2;+0:5]-[C:6]-[c:7]:[c:8]-1>>[CH3;D1;+0:1]-[C;H0;D4;+0:5]1(-[CH3;D1;+0:2])-[C:6]-[c:7]:[c:8]-[C:4]-1=[O;D1;H0:3] | null | [] | null | null | 0.5 | HOUR | 22.4 g of pulverized potassium hydroxide and 0.1 g of 18-dibenzocrown-6 are added portionwise to a solution of 25 g of 4-chloroindanone and 56.7 g of methyl iodide in 120 ml of dimethylformamide in such a manner that the temperature is kept below +70° C. When the exothermic reaction is over, 5.6 g of methyl iodide are ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HI | null | null | 0.5 | CI.CI.O=C1CCc2c(Cl)cccc21>>CC1(C)Cc2c(Cl)cccc2C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-085932d48bf14331abdf9a25304a46c5 | CC1(C)Cc2c(Cl)cccc2C1N=CNC#N.COC(=O)CBr>>COC(=O)c1cncn1C1c2cccc(Cl)c2CC1(C)C | C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[K+].[K+].C(#N)NC=NC1C(CC2=C(C=CC=C12)Cl)(C)C.BrCC(=O)OC>>COC(=O)C1=CN=CN1C1C(CC2=C(C=CC=C12)Cl)(C)C | N#[C:6][NH:7][CH:8]=[N:9][CH:10]1[c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]2[CH2:18][C:19]1([CH3:20])[CH3:21].Br[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]2[CH2:18][C:19]1([CH3:20])[CH3:21] | CC1(C)Cc2c(Cl)cccc2C1N=CNC#N.COC(=O)CBr | COC(=O)c1cncn1C1c2cccc(Cl)c2CC1(C)C | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | db02dc5dfb17181a055b24a942b62fc5275836628b97c95a452453eeef19bfc6 | 5d337f1b3dd397171244b5ace24da000a36b300a6429db4e96009e07843a18d8 | c1ccc2c(c1)CCC2n1ccnc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].N#[C;H0;D2;+0:6]-[NH;D2;+0:7]-[CH;D2;+0:8]=[N;H0;D2;+0:9]-[C:10](-[C:11])-[c:12]>>[C:11]-[C:10](-[n;H0;D3;+0:9]1:[cH;D2;+0:8]:[n;H0;D2;+0:7]:[cH;D2;+0:6]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[c:12] | 49.2 | [{"value": 49.2, "product": "COC(=O)C1=CN=CN1C1C(CC2=C(C=CC=C12)Cl)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 12.7 g of potassium carbonate are added to a solution of 21 g of N-cyano-N'-(2,2-dimethyl-4-chloroindan-1-yl)formamidine in 80 ml of dimethylformamide. 14.1 g of methyl bromoacetate are added dropwise. After the exothermic reaction has ceased the mixture is agitated for 1.5 hours at +50° C. another portion of 12.7 g of... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ester | Ester | null | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2c(c1)CCC2 | HBr | CN(C=O)C | null | 18 | CC1(C)Cc2c(Cl)cccc2C1N=CNC#N.COC(=O)CBr>CN(C=O)C>COC(=O)c1cncn1C1c2cccc(Cl)c2CC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e1764cad45a24269bfb95b0d00a282b2 | CC1CC(=O)c2ccccc21.COC(=O)CN>>CC1CC(N(C)CC(=O)O)c2ccccc21 | CC1CC(C2=CC=CC=C12)=O.NCC(=O)OC.S1C=CC=C1.C(=O)[O-].[Na+]>>CN(CC(=O)O)C1CC(C2=CC=CC=C12)C | O=[C:4]1[CH2:3][CH:2]([CH3:1])[c:16]2[c:11]1[cH:12][cH:13][cH:14][cH:15]2.C[O:10][C:8]([CH2:7][NH2:5])=[O:9]>>[CH3:1][CH:2]1[CH2:3][CH:4]([N:5]([CH3:6])[CH2:7][C:8](=[O:9])[OH:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | CC1CC(=O)c2ccccc21.COC(=O)CN | CC1CC(N(C)CC(=O)O)c2ccccc21 | null | [Pd] | CO | Heteroatom Alkylation and Arylation | OtherReaction | 2bc4eaa73f23ffd8d982e8944fe469fcba8b9dee744e421bad001b3fc257f848 | df47b4fe566332b22ca06efbaad8d3ee4806fcbd642480aefc26d5d77242391e | c1ccc2c(c1)CCC2 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[NH2;D1;+0:5].O=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[c:9]:[c:10]-1:[c:11]>>[C;D1;H3:12]-[N;H0;D3;+0:5](-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[CH;D3;+0:6]1-[C:7]-[C:8]-[c:9]:[c:10]-1:[c:11] | 54.1 | [{"value": 54.1, "product": "CN(CC(=O)O)C1CC(C2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 21 parts of 2,3-dihydro-3-methyl-1H-inden-1-one, 25 parts of methyl 2-aminoacetate, 2 parts of a solution of thiophene in methanol 4%, 25 parts of sodium formate and 480 parts of methanol is hydrogenated in a Parr-apparatus and at 50° C. with 5 parts of palladium-on-charcoal catalyst 10%. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Carboxylic acid.Tertiary amine | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | [Pd].CO | null | null | CC1CC(=O)c2ccccc21.COC(=O)CN>[Pd].CO>CC1CC(N(C)CC(=O)O)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a873420835704421bdbe4d1c155cadc8 | CC1CC(N(C)CC(=O)O)c2ccccc21.O=CO>>CC1CC(N(C=O)C(C)C(=O)O)c2ccccc21 | CN(CC(=O)O)C1CC(C2=CC=CC=C12)C.C(C)(=O)OC(C)=O.C(=O)O>>CC(N(C=O)C1CC(C2=CC=CC=C12)C)C(=O)O | [CH3:1][CH:2]1[CH2:3][CH:4]([N:5]([CH2:8][C:10](=[O:11])[OH:12])[CH3:9])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21.O[CH:6]=[O:7]>>[CH3:1][CH:2]1[CH2:3][CH:4]([N:5]([CH:6]=[O:7])[CH:8]([CH3:9])[C:10](=[O:11])[OH:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | CC1CC(N(C)CC(=O)O)c2ccccc21.O=CO | CC1CC(N(C=O)C(C)C(=O)O)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | e4fb14ba8d9fa2f7234edf0d64af7f50d102f78c1ee2361f849352db9a0089c6 | e56af770732f724a4446b034cf73b7c95d8ca0204a8c1cd008a666e4b19159c2 | c1ccc2c(c1)CCC2 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4](-[N;H0;D3;+0:5](-[CH3;D1;+0:6])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[c:11]>>[C:3]-[C:4](-[N;H0;D3;+0:5](-[CH;D2;+0:1]=[O;D1;H0:2])-[CH;D3;+0:7](-[CH3;D1;+0:6])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[c:11] | 78.7 | [{"value": 78.7, "product": "CC(N(C=O)C1CC(C2=CC=CC=C12)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 17 parts of methyl N-(2,3-dihydro-3-methyl-1H-inden-1-yl)glycine in 60 parts of formic acid and 20 parts of acetic acid anhydride is stirred overnight at room temperature. The reaction mixture is evaporated in vacuo and the residue is taken up in 1,1'-oxybisethane. The organic layer is washed with a sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Tertiary amide | null | null | c1ccc2c(c1)CCC2 | HO- | null | null | null | CC1CC(N(C)CC(=O)O)c2ccccc21.O=CO>>CC1CC(N(C=O)C(C)C(=O)O)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a725ac383d3d49d4a25d7e2303a9b53c | COC(=O)c1cnc(S)n1C1CC(C)c2ccccc21>>COC(=O)c1cncn1C1CC(C)c2ccccc21 | [OH-].[Na+].CC1CC(C2=CC=CC=C12)N1C(=NC=C1C(=O)OC)S.[N+](=O)(O)[O-]>>[N+](=O)(O)[O-].CC1CC(C2=CC=CC=C12)N1C=NC=C1C(=O)OC | S[c:8]1[n:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:9]1[CH:10]1[CH2:11][CH:12]([CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH:10]1[CH2:11][CH:12]([CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | COC(=O)c1cnc(S)n1C1CC(C)c2ccccc21 | COC(=O)c1cncn1C1CC(C)c2ccccc21 | null | null | null | Reduction | OtherReaction | eae27167089e95faf7ce5ed478321b2a0cf6e27101b71987c0c66ed8073c81f6 | 6dfa579c3c25232785e7dcb34dfc1e7688e0474e6615711d0e6a05188bc6f710 | c1ccc2c(c1)CCC2n1ccnc1 | S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#7;a:8]:1-[C:9]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:3]:[#7;a:2]:[cH;D2;+0:1]:[#7;a:8]:1-[C:9] | 62.6 | [{"value": 62.6, "product": "[N+](=O)(O)[O-].CC1CC(C2=CC=CC=C12)N1C=NC=C1C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 10 parts of methyl 1-(2,3-dihydro-3-methyl-1H-inden-1-yl)-2-mercapto-1H-imidazole-5-carboxylate and 120 parts of a nitric acid solution 30% is stirred for 30 minutes at room temperature (intense reaction). The reaction mixture is poured into crushed ice and treated with a sodium hydroxide solution. The pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2c(c1)CCC2 | Other | null | null | 0.5 | COC(=O)c1cnc(S)n1C1CC(C)c2ccccc21>>COC(=O)c1cncn1C1CC(C)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a31b6d4ef7e040b1a5ea277dc09e088c | COC(=O)c1cncn1C1CC(C)c2ccccc21>>CC1CC(n2cncc2C(=O)O)c2ccccc21 | [N+](=O)(O)[O-].CC1CC(C2=CC=CC=C12)N1C=NC=C1C(=O)OC.[OH-].[Na+]>>CC1CC(C2=CC=CC=C12)N1C=NC=C1C(=O)O | C[O:12][C:10]([c:9]1[n:5]([CH:4]2[CH2:3][CH:2]([CH3:1])[c:18]3[c:13]2[cH:14][cH:15][cH:16][cH:17]3)[cH:6][n:7][cH:8]1)=[O:11]>>[CH3:1][CH:2]1[CH2:3][CH:4]([n:5]2[cH:6][n:7][cH:8][c:9]2[C:10](=[O:11])[OH:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | COC(=O)c1cncn1C1CC(C)c2ccccc21 | CC1CC(n2cncc2C(=O)O)c2ccccc21 | null | null | C(C)(=O)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)CCC2n1ccnc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | 90 | [{"value": 90.0, "product": "CC1CC(C2=CC=CC=C12)N1C=NC=C1C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3.6 parts of methyl 1-(2,3-dihydro-3-methyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate mononitrate in 50 parts of a sodium hydroxide solution 20% is stirred for 1.5 hours at reflux temperature. After cooling, the reaction mixture is neutralized with acetic acid. The product is extracted with 1,1'-oxybiseth... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc[nH]1.c1ccc2c(c1)CCC2 | Other | C(C)(=O)O | null | null | COC(=O)c1cncn1C1CC(C)c2ccccc21>C(C)(=O)O>CC1CC(n2cncc2C(=O)O)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4af060a23de24f8e80acbb43ee1a8a58 | COCCCl.O=C(O)c1cncn1C1CCCc2ccccc21>>COCCOC(=O)c1cncn1C1CCCc2ccccc21 | C1(CCCC2=CC=CC=C12)N1C=NC=C1C(=O)O.[H-].[Na+].ClCCOC>>C1(CCCC2=CC=CC=C12)N1C=NC=C1C(=O)OCCOC | Cl[CH2:4][CH2:3][O:2][CH3:1].[OH:5][C:6](=[O:7])[c:8]1[cH:9][n:10][cH:11][n:12]1[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[cH:9][n:10][cH:11][n:12]1[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | COCCCl.O=C(O)c1cncn1C1CCCc2ccccc21 | COCCOC(=O)c1cncn1C1CCCc2ccccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccc2c(c1)CCCC2n1ccnc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7;a:4]:[c:5]:[c:6](-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[#7;a:10]>>[#7;a:4]:[c:5]:[c:6](-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[#7;a:10] | 46.7 | [{"value": 46.7, "product": "C1(CCCC2=CC=CC=C12)N1C=NC=C1C(=O)OCCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4.8 Parts of 1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole-5-carboxylic acid are dissolved in 94 parts of warm N,N-dimethylformamide. 0.96 Parts of a sodium hydride dispersion 50% are added portionwise to the thus obtained reaction mixture. Upon complete addition, stirring is continued for 1 hour at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1c[nH]cn1.c1ccc2c(c1)CCCC2 | HCl | CN(C=O)C | null | 1 | COCCCl.O=C(O)c1cncn1C1CCCc2ccccc21>CN(C=O)C>COCCOC(=O)c1cncn1C1CCCc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9fc75b912d0046a3a872e761ace84d22 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1.CN1CCNCC1>>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCN(C)CC2)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)N=C=S)N2CCC(CC2)C.CN1CCNCC1>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)N2CCN(CC2)C)N2CCC(CC2)C | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[N:19]=[C:20]=[S:21])[CH2:29][CH2:30]1.[NH:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:1... | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1.CN1CCNCC1 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCN(C)CC2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | ffc0a97fbb7803c8ffec3d1f54c2fb07d25092ebf582a6d00ebbacbd14015afa | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | S=C(Nc1cc2scnc2cc1N1CCCCC1)N1CCNCC1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[S;D1;H0:7]):[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;D1;H0:7])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1):[c:8] | 95.1 | [{"value": 95.1, "product": "C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)N2CCN(CC2)C)N2CCC(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of 90 g of 2-tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole in 900 ml of methylene chloride is added dropwise 26 g of N-methylpiperazine. The solution is stirred for 1 hour, washed with water, dried over anhydrous sodium sulphate and evaporated to give 110 g of 2-tert-butyl-6-... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2scnc2c1.C1C[NH]CC[NH]1 | null | C(Cl)Cl | null | 1 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1.CN1CCNCC1>C(Cl)Cl>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCN(C)CC2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-269df9c1e534472b9cb72738c8208fee | CC(C)(C)c1nc2cc(Cl)c([N+](=O)[O-])cc2s1.CC1CCNCC1>>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 | O.C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)[N+](=O)[O-])Cl.CC1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)[N+](=O)[O-])N2CCC(CC2)C | Cl[c:6]1[cH:7][c:8]2[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]2[cH:17][c:18]1[N+:19](=[O:20])[O-:21].[CH3:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:22][CH2:23]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[N+:19](=[O:20])[O-:21]... | CC(C)(C)c1nc2cc(Cl)c([N+](=O)[O-])cc2s1.CC1CCNCC1 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 | null | null | C(Cl)(Cl)Cl.CS(=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 23940903aa7aade562a2a6bb5bb712c644c4ccfd92817133b79b0dc88344f250 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1nc2cc(N3CCCCC3)ccc2s1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:2:[c:8]:[c:9]:1-[#7;+:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[#7;+:10]-[c:9]1:[c:8]:[c:7]2:[#16;a:6]:[c:5]:[#7;a:4]:[c:3]:2:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:13](-[C:12]-[C:11])-[C:14]-[C:15] | null | [] | null | null | null | null | A solution of 32,4 g of 2-tert-butyl-5-chloro-6-nitrobenzothiazole, (described in European patent application 85810418.5 published under No. 0175650) in 300 ml of dimethylsulphoxide, is stirred and heated at 140° for 6 hours with 12.8 g of 4-methylpiperidine and 35.8 g of anhydrous potassium carbonate, cooled and poure... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2scnc2c1.C1CCNCC1 | C1CC[NH]CC1.c1ccc2scnc2c1 | C1CC[NH]CC1.c1ccc2scnc2c1 | HCl | C(Cl)(Cl)Cl.CS(=O)C | null | null | CC(C)(C)c1nc2cc(Cl)c([N+](=O)[O-])cc2s1.CC1CCNCC1>C(Cl)(Cl)Cl.CS(=O)C>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d2d2589cd1d140879dce79874d0e6100 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1>>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)[N+](=O)[O-])N2CCC(CC2)C>>NC1=CC2=C(N=C(S2)C(C)(C)C)C=C1N1CCC(CC1)C | O=[N+:19]([O-])[c:18]1[c:6]([N:5]2[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:21][CH2:20]2)[cH:7][c:8]2[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]2[cH:17]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[NH2:19])[CH2:20][CH2:21]1 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1 | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1nc2cc(N3CCCCC3)ccc2s1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | null | null | A solution of 15.2 g of 2-tert-butyl-5-(4-methyl-piperidin-1-yl)-6-nitrobenzothiazole in 600 ml of methanol is hydrogenated in presence of 6.5 g of Raney Nickel at room temperature. After removing the catalyst the solution is concentrated and the solid filtered to give 6-amino-2-tert-butyl-5-(4-methylpiperidin-1-yl)ben... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]CC1.c1ccc2scnc2c1 | Other | [Ni].CO | null | null | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1>[Ni].CO>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6cc07c4d63d84829877b5eb5f5957d9d | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1.S=C(Cl)Cl>>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 | C(=S)(Cl)Cl.NC1=CC2=C(N=C(S2)C(C)(C)C)C=C1N1CCC(CC1)C.C([O-])(O)=O.[K+]>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)N=C=S)N2CCC(CC2)C | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[NH2:19])[CH2:22][CH2:23]1.Cl[C:20](Cl)=[S:21]>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[N:19]=[C:20]=[S:21]... | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1.S=C(Cl)Cl | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | c1nc2cc(N3CCCCC3)ccc2s1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[#16;a:3]:[c:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8]>>[#16;a:3]:[c:4]:[c:5]:[c:6](-[N;H0;D2;+0:7]=[C;H0;D2;+0:1]=[S;D1;H0:2]):[c:8] | null | [] | null | null | 2 | HOUR | To a cooled mixture of 2.1 g of 6-amino-2-tert-butyl-5-(4-methylpiperidin-1-yl)benzothiazole and 2.8 g of potassium bicarbonate in 20 ml of chloroform is added dropwise 1.6 g of thiophosgene in 5 ml of chloroform under stirring. The stirring is continued for 2 hours maintaining the temperature at 0°-2° . The solid is f... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | C1CC[NH]CC1.c1ccc2scnc2c1 | HCl | C(Cl)(Cl)Cl | null | 2 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1.S=C(Cl)Cl>C(Cl)(Cl)Cl>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c586dd8d365640deae3890d8575254f9 | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1.CN1CCNCC1>>CN1CCN(C(=S)Nc2cc3sc(C(C)(C)C)nc3cc2N2CCN(C)CC2)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)N=C=S)N2CCN(CC2)C.CN1CCNCC1>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)N2CCN(CC2)C)N2CCN(CC2)C | [C:6](=[S:7])=[N:8][c:9]1[cH:10][c:11]2[s:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[n:18][c:19]2[cH:20][c:21]1[N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:29][CH2:30]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[S:7])[NH:8][c:9]2[cH:10][c:11]3[s:12][c:13]([C:14]([CH3:... | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1.CN1CCNCC1 | CN1CCN(C(=S)Nc2cc3sc(C(C)(C)C)nc3cc2N2CCN(C)CC2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | thiourea | beb066691ff40a37c26bc4234840e891c6843c6d14f49542e84576855b81b429 | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | S=C(Nc1cc2scnc2cc1N1CCNCC1)N1CCNCC1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[S;D1;H0:7]):[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;D1;H0:7])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1):[c:8] | null | [] | null | null | null | null | Using the procedure described in Example 1 by reaction of 2-tert-butyl-6-isothiocyanato-5-(4-methyl-piperazin-1-yl)benzothiazole with 4-methylpiperazine is obtained 2-tert-butyl-6[(4-methylpiperazin-1-yl)thiocarbonylamino]-5-(4-methyl-piperazin-1-yl)benzothiazole, melting at 190°-193°.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1.C1C[NH]CC[NH]1 | null | null | null | null | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1.CN1CCNCC1>>CN1CCN(C(=S)Nc2cc3sc(C(C)(C)C)nc3cc2N2CCN(C)CC2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8d6c5e55a6af4dfdb2e2e90fcdc60967 | CC(C)(C)C(=S)Nc1cc(Cl)c([N+](=O)[O-])cc1Cl.CN1CCNCC1>>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 | C(C)(C)(C)C(=S)NC1=C(C=C(C(=C1)Cl)[N+](=O)[O-])Cl.CN1CCNCC1.O>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)[N+](=O)[O-])N2CCN(CC2)C | Cl[c:6]1[cH:7][c:8]([NH:9][C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])=[S:15])[c:16](Cl)[cH:17][c:18]1[N+:19](=[O:20])[O-:21].[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:22][CH2:23]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[N+:19](=[O:20])[O-... | CC(C)(C)C(=S)Nc1cc(Cl)c([N+](=O)[O-])cc1Cl.CN1CCNCC1 | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | 297f82e651599316300ea4f144d833ce40a1bbc8b8cc5d293abe23ff11a6a397 | 3d6aed948203792cde1994139fdaf33ee119c39bdeb5518dc010f2535b646762 | c1nc2cc(N3CCNCC3)ccc2s1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7;+:4]):[c;H0;D3;+0:5](-Cl):[c:6]:[c:7]:1-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[S;H0;D1;+0:10])-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14].[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[#7;+:4]-[c:3]1:[c:2]:[c;H0;D3;+0:1]2:[s;H0;D2;+0:10]:[c;H0;D3;+0:9](-[C:11](-[C;D1;H3:12])(-[... | null | [] | null | null | null | null | A solution of 171 g of N-tert-butylthiocarbonyl-2,5-dichloro-4-nitroaniline (described in European patent application No. 85810418.5 published under No. 0175650) and 605 ml of N-methylpiperazine in 1700 ml of dimethylsulphoxide is heated at 140° for 8 hours, cooled and poured into water. The solid is filtered, washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Thioamide.Secondary amine | Tertiary amine | c1ccccc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1 | HCl | CS(=O)C | null | null | CC(C)(C)C(=S)Nc1cc(Cl)c([N+](=O)[O-])cc1Cl.CN1CCNCC1>CS(=O)C>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c4b9469cd7684e858e4abf2ec83970cc | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1>>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)[N+](=O)[O-])N2CCN(CC2)C>>NC1=CC2=C(N=C(S2)C(C)(C)C)C=C1N1CCN(CC1)C | O=[N+:19]([O-])[c:18]1[c:6]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:21][CH2:20]2)[cH:7][c:8]2[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]2[cH:17]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[NH2:19])[CH2:20][CH2:21]1 | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1 | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1 | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1nc2cc(N3CCNCC3)ccc2s1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | null | null | A solution of 86 g of the above nitro compound in 150 ml of ethanol is hydrogenated in presence of 30 g of Raney nickel at 45°. The solution is filtered to give 6-amino-2-tert-butyl-5-(4-methylpiperazin-1-yl)benzothiazole, melting at 130° C.
Conditions: See reaction.notes.procedure_details.
Workup: The solution is filt... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccc2scnc2c1 | Other | [Ni].C(C)O | null | null | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1>[Ni].C(C)O>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a9b6c5936caf4afa829011ebb019f26e | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1.S=C(Cl)Cl>>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 | [OH-].[Na+].NC1=CC2=C(N=C(S2)C(C)(C)C)C=C1N1CCN(CC1)C.C([O-])(O)=O.[Na+].C(=S)(Cl)Cl>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)N=C=S)N2CCN(CC2)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[NH2:19])[CH2:22][CH2:23]1.Cl[C:20](Cl)=[S:21]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[N:19]=[C:20]=[S:21])[... | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1.S=C(Cl)Cl | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 | null | null | C(Cl)(Cl)Cl.O | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | c1nc2cc(N3CCNCC3)ccc2s1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[#16;a:3]:[c:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8]>>[#16;a:3]:[c:4]:[c:5]:[c:6](-[N;H0;D2;+0:7]=[C;H0;D2;+0:1]=[S;D1;H0:2]):[c:8] | null | [] | null | null | 4 | HOUR | To a stirred mixture of 75 g of 6-Amino-2-tert-butyl-5-(4-methylpiperazin-1-yl)benzothiazole and 29 g of sodium bicarbonate in 1100 ml of chloroform at 0° is added 41 g of thiophosgene and the mixture stirred at 10° for 4 hours. After filtering off the solid, the solution is evaporated to get a yellow solid which is di... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | C1C[NH]CC[NH]1.c1ccc2scnc2c1 | HCl | C(Cl)(Cl)Cl.O | null | 4 | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N)CC1.S=C(Cl)Cl>C(Cl)(Cl)Cl.O>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-498a7819ece24228b5eb4b4daeed8749 | C1CCNCC1.CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1>>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCCCC2)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)N=C=S)N2CCN(CC2)C.N1CCCCC1>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)N2CCCCC2)N2CCN(CC2)C | [NH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1.[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[N:19]=[C:20]=[S:21])[CH2:28][CH2:29]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][... | C1CCNCC1.CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 | CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCCCC2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | thiourea | 22c0be506eba558bc623a80aec10790e7277d2acd89004b822814260d768b6ca | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | S=C(Nc1cc2scnc2cc1N1CCNCC1)N1CCCCC1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[S;D1;H0:7]):[c:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;D1;H0:7])-[N;H0;D3;+0:11](-[C:10]-[C:9])-[C:12]-[C:13]):[c:8] | null | [] | null | null | null | null | Reaction of 2-tert-butyl-6-isothiocyanato-5-(4-methyl-piperazin-1-yl)benzothiazole described in Example 2 with piperidine under conditions described in Example 1 gives 2-tert-butyl-6-[(piperidin-1-yl)thiocarbonylamino]-5-(4-methyl-piperazin-1-yl)benzothiazole, melting at 202°-206°.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | C1CCNCC1 | C1CC[NH]CC1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1.C1CC[NH]CC1 | null | null | null | null | C1CCNCC1.CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1>>CN1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCCCC2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0021d0cc1d434e90be2099cbc1a36c49 | C1CNCCN1.CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1>>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCNCC2)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)N=C=S)N2CCC(CC2)C.N1CCNCC1>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)N2CCNCC2)N2CCC(CC2)C | [NH:22]1[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]1.[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17][c:18]2[N:19]=[C:20]=[S:21])[CH2:28][CH2:29]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15]... | C1CNCCN1.CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCNCC2)CC1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | 0ffd0e1a6ff3ac1a0669a3464c502b065eb1f716362b6957d50d08a7f94ff96f | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | S=C(Nc1cc2scnc2cc1N1CCCCC1)N1CCNCC1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[S;D1;H0:7]):[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;D1;H0:7])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1):[c:8] | 69.6 | [{"value": 69.6, "product": "C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)N2CCNCC2)N2CCC(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 3.45 g of 2-tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole, described in Example 1, and 8.6 g of anhydrous piperazine in 30 ml of chloroform is stirred for 3 hours, washed with water, dried over anhydrous sodium sulphate and evaporated to get a sticky residue which is triturated with ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | C1CNCCN1 | C1C[NH]CCN1 | C1CC[NH]CC1.c1ccc2scnc2c1.C1C[NH]CCN1 | null | C(Cl)(Cl)Cl | null | 3 | C1CNCCN1.CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1>C(Cl)(Cl)Cl>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCNCC2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c1cccb7f4ab14334a9142cd6bd51341b | CC(=O)N1CCNCC1.CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1>>CC(=O)N1CCN(C(=S)Nc2cc3sc(C(C)(C)C)nc3cc2N2CCC(C)CC2)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)N=C=S)N2CCC(CC2)C.C(C)(=O)N1CCNCC1>>C(C)(=O)N1CCN(CC1)C(=S)NC1=CC2=C(N=C(S2)C(C)(C)C)C=C1N1CCC(CC1)C | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:31][CH2:32]1.[C:8](=[S:9])=[N:10][c:11]1[cH:12][c:13]2[s:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][c:21]2[cH:22][c:23]1[N:24]1[CH2:25][CH2:26][CH:27]([CH3:28])[CH2:29][CH2:30]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([C:8](=[S:9])[NH:10][c:11]2[cH:12][... | CC(=O)N1CCNCC1.CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1 | CC(=O)N1CCN(C(=S)Nc2cc3sc(C(C)(C)C)nc3cc2N2CCC(C)CC2)CC1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | beb066691ff40a37c26bc4234840e891c6843c6d14f49542e84576855b81b429 | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | S=C(Nc1cc2scnc2cc1N1CCCCC1)N1CCNCC1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[S;D1;H0:7]):[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[S;D1;H0:7])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1):[c:8] | null | [] | null | null | null | null | A solution of 2.0 g of 2-tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole and 0.78 g of 1-acetyl-piperazine in 30 ml of chloroform is stirred for 30 minutes and the product triturated with petroleum ether to obtain 6-[(4-acetyl-piperazin-1-yl)thiocarbonylamino]-2-tert-butyl-5-(4-methylpiperidin-1-yl)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1.C1CC[NH]CC1 | null | C(Cl)(Cl)Cl | null | null | CC(=O)N1CCNCC1.CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2N=C=S)CC1>C(Cl)(Cl)Cl>CC(=O)N1CCN(C(=S)Nc2cc3sc(C(C)(C)C)nc3cc2N2CCC(C)CC2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-31d1f67ee9ff459da6d1d62523ee490c | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)Oc2ccccc2)CC1.CN1CCNCC1>>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCN(C)CC2)CC1 | C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)OC2=CC=CC=C2)N2CCC(CC2)C.CN1CCNCC1>>C(C)(C)(C)C=1SC2=C(N1)C=C(C(=C2)NC(=S)N2CCN(CC2)C)N2CCC(CC2)C | c1ccc(O[C:20]([NH:19][c:18]2[c:6]([N:5]3[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:30][CH2:29]3)[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[s:15][c:16]3[cH:17]2)=[S:21])cc1.[NH:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]3[n:9][c:10]([C:11]([CH3:12])(... | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)Oc2ccccc2)CC1.CN1CCNCC1 | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCN(C)CC2)CC1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | f203caeb853ec2a5d06ef14ace71f92aa0cf64e04c1926993a6e02783752f4c4 | a7203ce657e7d6b42383ef88862a35a277cf8306602c3faf7b8bbf0a1e9adfe3 | S=C(Nc1cc2scnc2cc1N1CCCCC1)N1CCNCC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[S;D1;H0:7]=[C;H0;D3;+0:8](-O-c1:c:c:c:c:c:1)-[#7:9]-[c:10]>>[S;D1;H0:7]=[C;H0;D3;+0:8](-[#7:9]-[c:10])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | A solution of 0.5 g of 2-tert-butyl-5-(4-methyl-piperidin-1-yl)-6-phenoxythiocarbonylaminobenzothiazole and 0.11 g of 4-methylpiperazine in 20 ml of dioxane is refluxed for 16 hours. Evaporation of the solvent and chromatography of the residue over silica gel and elution with methylene dichloride-methanol (98:2) gives ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Thioamide.Secondary amine | Thiourea | c1ccccc1.C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2scnc2c1.C1C[NH]CC[NH]1 | HO- | O1CCOCC1 | null | null | CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)Oc2ccccc2)CC1.CN1CCNCC1>O1CCOCC1>CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2NC(=S)N2CCN(C)CC2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-776b6e04372e48e3ab61b37e552959a1 | CC1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>>CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | N.NC1=CC=C(C=C1)C=1C(CC(NN1)=O)C.O1C=CC(C=C1)=O.Cl>>CC1CC(NN=C1C1=CC=C(C=C1)N1C=CC(C=C1)=O)=O | [CH3:1][CH:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:20][cH:21]1.o1[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]1>>[CH3:1][CH:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | CC1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1 | CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A stirred mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (1.0 g), 4H-pyran-4-one (0.52 g), water (20 ml), and concentrated hydrochloric acid (0.41 ml) was heated under reflux for 31/2 hours. The resultant solid was dissolved in the minimum of hot water and the solution was neutralised with aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | C1=NNCCC1.c1ccccc1.c1ccncc1 | HO- | O | null | null | CC1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>O>CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-485e041677a3458f8860e1c73bcd36fb | Nc1ccc(C2=NNC(=O)CC2)cc1.O=c1ccocc1>>O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | Cl.NC1=CC=C(C=C1)C=1CCC(NN1)=O.O1C=CC(C=C1)=O.N>>O=C1C=CN(C=C1)C1=CC=C(C=C1)C=1CCC(NN1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:17][cH:18]2)=[N:19][NH:20]1.o1[cH:11][cH:12][c:13](=[O:14])[cH:15][cH:16]1>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9](-[n:10]3[cH:11][cH:12][c:13](=[O:14])[cH:15][cH:16]3)[cH:17][cH:18]2)=[N:19][NH:20]1 | Nc1ccc(C2=NNC(=O)CC2)cc1.O=c1ccocc1 | O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A stirred mixture of 6-(4-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone hydrochloride (1.5 g), 4H-pyran-4-one (0.7 g), and water (20 ml), was heated under reflux for 41/2 hours. The resultant solid was dissolved in the minimum of hot water and the solution was neutralised with ammonia to give the crude product. Recrystal... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | C1=NNCCC1.c1ccccc1.c1ccncc1 | HO- | O | null | null | Nc1ccc(C2=NNC(=O)CC2)cc1.O=c1ccocc1>O>O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e0927e1207d4f81994448ab79173b02 | Nc1ccc(-c2ccc(=O)[nH]n2)cc1.O=c1ccocc1>>O=c1ccn(-c2ccc(-c3ccc(=O)[nH]n3)cc2)cc1 | Cl.NC1=CC=C(C=C1)C=1C=CC(NN1)=O.O1C=CC(C=C1)=O.N>>O=C1C=CN(C=C1)C1=CC=C(C=C1)C=1C=CC(NN1)=O | [NH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13](=[O:14])[nH:15][n:16]2)[cH:17][cH:18]1.o1[cH:4][cH:3][c:2](=[O:1])[cH:20][cH:19]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13](=[O:14])[nH:15][n:16]3)[cH:17][cH:18]2)[cH:19][cH:20]1 | Nc1ccc(-c2ccc(=O)[nH]n2)cc1.O=c1ccocc1 | O=c1ccn(-c2ccc(-c3ccc(=O)[nH]n3)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1ccn(-c2ccc(-c3ccc(=O)[nH]n3)cc2)cc1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A stirred mixture of 6-(4-aminophenyl)-3(2H)-pyridazinone hydrochloride (1.5 g), 4H-pyran-4-one (0.71 g), and water (20 ml), was heated under reflux for 2 hours. The pH of the hot solution was adjusted to 8 with aqueous ammonia and the mixture was cooled to give the crude product, 1.84 g, m.p. 338°-340° C. Recrystallis... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1cccnn1 | HO- | O | null | null | Nc1ccc(-c2ccc(=O)[nH]n2)cc1.O=c1ccocc1>O>O=c1ccn(-c2ccc(-c3ccc(=O)[nH]n3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4206414e65394297bb38130b22a09378 | Nc1ccc(C2=NNC(=O)CS2)cc1.O=c1ccocc1>>O=C1CSC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | N.NC1=CC=C(C=C1)C=1SCC(NN1)=O.O1C=CC(C=C1)=O.Cl>>O=C1C=CN(C=C1)C1=CC=C(C=C1)C=1SCC(NN1)=O | [O:1]=[C:2]1[CH2:3][S:4][C:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:17][cH:18]2)=[N:19][NH:20]1.o1[cH:11][cH:12][c:13](=[O:14])[cH:15][cH:16]1>>[O:1]=[C:2]1[CH2:3][S:4][C:5]([c:6]2[cH:7][cH:8][c:9](-[n:10]3[cH:11][cH:12][c:13](=[O:14])[cH:15][cH:16]3)[cH:17][cH:18]2)=[N:19][NH:20]1 | Nc1ccc(C2=NNC(=O)CS2)cc1.O=c1ccocc1 | O=C1CSC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C1CSC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A stirred mixture of 2-(4-aminophenyl)-4H,6H-1,3,4-thiadiazin-5-one (1.0 g), 4H-pyran-4-one (0.51 g), water (20 ml) and concentrated hydrochloric acid (0.42 ml), was heated under reflux for 3 hours. The warm solution was neutralised with concentrated aqueous ammonia and cooled to give a solid, 1.33 g. Recrystallisation... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | C1=NNCCS1.c1ccccc1.c1ccncc1 | HO- | O | null | null | Nc1ccc(C2=NNC(=O)CS2)cc1.O=c1ccocc1>O>O=C1CSC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2f8234d22a2e4c56b954a52e13ae7222 | CC1SC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>>CC1SC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | NC1=CC=C(C=C1)C1=NNC(SC1C)=O.O1C=CC(C=C1)=O.C(C)(=O)O>>O=C1C=CN(C=C1)C1=CC=C(C=C1)C1=NNC(SC1C)=O | [CH3:1][CH:2]1[S:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:20][cH:21]1.o1[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]1>>[CH3:1][CH:2]1[S:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | CC1SC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1 | CC1SC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C1NN=C(c2ccc(-n3ccc(=O)cc3)cc2)CS1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A stirred mixture of 5-(4-aminophenyl)-6-methyl-3H,6H-1,3,4-thiadiazine-2-one (0.54 g), 4H-pyran-4-one (0.26 g), glacial acetic acid (0.15 g) and water (20 ml) was heated under reflux for 24 hours to give a solid, 0.54 g. Recrystallisation from aqueous ethanol gave the title compound, 0.28 g, which darkened at 265° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | C1=NNCSC1.c1ccccc1.c1ccncc1 | HO- | O | null | null | CC1SC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>O>CC1SC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-acfd563acf594497a8d324ed74eb0b8c | Nc1ccc(-c2c[nH]c(=O)cn2)cc1.O=c1ccocc1>>O=c1ccn(-c2ccc(-c3c[nH]c(=O)cn3)cc2)cc1 | Cl.NC1=CC=C(C=C1)C=1N=CC(NC1)=O.Cl.O1C=CC(C=C1)=O>>O=C1C=CN(C=C1)C1=CC=C(C=C1)C=1N=CC(NC1)=O | [NH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][nH:12][c:13](=[O:14])[cH:15][n:16]2)[cH:17][cH:18]1.o1[cH:4][cH:3][c:2](=[O:1])[cH:20][cH:19]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][nH:12][c:13](=[O:14])[cH:15][n:16]3)[cH:17][cH:18]2)[cH:19][cH:20]1 | Nc1ccc(-c2c[nH]c(=O)cn2)cc1.O=c1ccocc1 | O=c1ccn(-c2ccc(-c3c[nH]c(=O)cn3)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1ccn(-c2ccc(-c3c[nH]c(=O)cn3)cc2)cc1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A stirred mixture of 5-(4-aminophenyl)-2(1H)pyrazinone hydrochloride (1.5 g, from hydrolysis of the corresponding acetamido derivative with hydrochloric acid), 4H-pyran-4-one (0.71 g) and water (15 ml) was heated under reflux for 21/2 hours under a nitrogen atmosphere. The resultant solution was neutralised to give a s... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1cnccn1 | HO- | O | null | null | Nc1ccc(-c2c[nH]c(=O)cn2)cc1.O=c1ccocc1>O>O=c1ccn(-c2ccc(-c3c[nH]c(=O)cn3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f6081b4f6c874294b9305d5620438d99 | Nc1ccc2c(c1)Cc1cc(=O)[nH]nc1-2.O=c1ccocc1>>O=c1ccn(-c2ccc3c(c2)Cc2cc(=O)[nH]nc2-3)cc1 | Cl.NC=1C=C2CC=3C(=NNC(C3)=O)C2=CC1.O1C=CC(C=C1)=O.N>>O=C1C=CN(C=C1)C=1C=C2CC=3C(=NNC(C3)=O)C2=CC1 | [NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][c:13]1[cH:14][c:15](=[O:16])[nH:17][n:18][c:19]1-2.o1[cH:4][cH:3][c:2](=[O:1])[cH:21][cH:20]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[CH2:12][c:13]2[cH:14][c:15](=[O:16])[nH:17][n:18][c:19]2-3)[cH:20][cH:21]1 | Nc1ccc2c(c1)Cc1cc(=O)[nH]nc1-2.O=c1ccocc1 | O=c1ccn(-c2ccc3c(c2)Cc2cc(=O)[nH]nc2-3)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1ccn(-c2ccc3c(c2)Cc2cc(=O)[nH]nc2-3)cc1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A stirred mixture of 7-amino-[5H]indeno[1,2-c]pyridazin-3(2H)-one hydrochloride (1.0 g) and 4H-pyran-4-one (0.48 g) in water (10 ml) was heated under reflux for 1 hour in a nitrogen atmosphere. The warm mixture was neutralised with aqueous ammonia to give a solid, 0.9 g, m.p. >300° C. This solid was triturated with war... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)Cc1ccnnc12 | HO- | O | null | null | Nc1ccc2c(c1)Cc1cc(=O)[nH]nc1-2.O=c1ccocc1>O>O=c1ccn(-c2ccc3c(c2)Cc2cc(=O)[nH]nc2-3)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-59c565222c524969851c7e1b747f4739 | Nc1ccc2c(c1)CCC1CC(=O)NN=C21.O=c1ccocc1>>O=C1CC2CCc3cc(-n4ccc(=O)cc4)ccc3C2=NN1 | Cl.NC=1C=CC2=C(CCC3CC(NN=C23)=O)C1.O1C=CC(C=C1)=O>>O=C1C=CN(C=C1)C=1C=CC2=C(CCC3CC(NN=C23)=O)C1 | [O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][c:7]3[cH:8][c:9]([NH2:10])[cH:17][cH:18][c:19]3[C:20]2=[N:21][NH:22]1.o1[cH:11][cH:12][c:13](=[O:14])[cH:15][cH:16]1>>[O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][c:7]3[cH:8][c:9](-[n:10]4[cH:11][cH:12][c:13](=[O:14])[cH:15][cH:16]4)[cH:17][cH:18][c:19]3[C:20]2=[N:21][NH:22]1 | Nc1ccc2c(c1)CCC1CC(=O)NN=C21.O=c1ccocc1 | O=C1CC2CCc3cc(-n4ccc(=O)cc4)ccc3C2=NN1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C1CC2CCc3cc(-n4ccc(=O)cc4)ccc3C2=NN1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | 10.3 | [{"value": 10.3, "product": "O=C1C=CN(C=C1)C=1C=CC2=C(CCC3CC(NN=C23)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 8-amino-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one hydrochloride (1.5 g) and 4H-pyran-4-one (0.84 g) in water (40 ml) was heated under reflux for 2 hours in a nitrogen atmosphere. The resultant solid was washed with dilute hydrochloric acid to give a crude product, 0.5 g. Purification by column ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccc2c(c1)CCC1CCNN=C21.c1ccncc1 | HO- | O | null | null | Nc1ccc2c(c1)CCC1CC(=O)NN=C21.O=c1ccocc1>O>O=C1CC2CCc3cc(-n4ccc(=O)cc4)ccc3C2=NN1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5b3edb5c38374dab95408851f226d3f9 | Nc1ccc(-c2n[nH]c(=O)s2)cc1.O=c1ccocc1>>O=c1ccn(-c2ccc(-c3n[nH]c(=O)s3)cc2)cc1 | Cl.NC1=CC=C(C=C1)C1=NNC(S1)=O.O1C=CC(C=C1)=O.C(C)O>>O=C1C=CN(C=C1)C1=CC=C(C=C1)C1=NNC(S1)=O | [NH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][nH:12][c:13](=[O:14])[s:15]2)[cH:16][cH:17]1.o1[cH:4][cH:3][c:2](=[O:1])[cH:19][cH:18]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[n:11][nH:12][c:13](=[O:14])[s:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1 | Nc1ccc(-c2n[nH]c(=O)s2)cc1.O=c1ccocc1 | O=c1ccn(-c2ccc(-c3n[nH]c(=O)s3)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1ccn(-c2ccc(-c3n[nH]c(=O)s3)cc2)cc1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A mixture of 5-(4-aminophenyl)-1,3,4-thiadiazol-2(3H)-one hydrochloride (1.25 g), 4H-pyran-4-one (0.58 g), ethanol (10 ml) and water (50 ml) was stirred under reflux under nitrogen for 31/2 hours. The cooled reaction mixture was filtered and the collected orange solid was washed with aqueous potassium hydrogen carbonat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1nncs1 | HO- | O | null | null | Nc1ccc(-c2n[nH]c(=O)s2)cc1.O=c1ccocc1>O>O=c1ccn(-c2ccc(-c3n[nH]c(=O)s3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d3f1608a6b4f44cb9da8fc4248faeacd | O=c1[nH]nc(-c2ccc([N+](=O)[O-])cc2)o1>>Nc1ccc(-c2n[nH]c(=O)o2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C1=NNC(O1)=O>>NC1=CC=C(C=C1)C1=NNC(O1)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][c:9](=[O:10])[o:11]2)[cH:12][cH:13]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][c:9](=[O:10])[o:11]2)[cH:12][cH:13]1 | O=c1[nH]nc(-c2ccc([N+](=O)[O-])cc2)o1 | Nc1ccc(-c2n[nH]c(=O)o2)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]nc(-c2ccccc2)o1 | 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 | 5-(4-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one, (0.65 g) in ethanol (100 ml) was hydrogenated at 276 kPa (40 p.s.i.) in the presence of palladium on carbon at room temperature for one hour. The reaction mixture was filtered, the filtrate was evaporated to dryness and the resultant yellow solid was recrystallised from etha... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1nnco1 | Other | [Pd].C(C)O | null | null | O=c1[nH]nc(-c2ccc([N+](=O)[O-])cc2)o1>[Pd].C(C)O>Nc1ccc(-c2n[nH]c(=O)o2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c091a3ddf3114d9bb84a4a03518b6901 | Nc1ccc(-c2n[nH]c(=O)o2)cc1.O=c1ccocc1>>O=c1ccn(-c2ccc(-c3n[nH]c(=O)o3)cc2)cc1 | N.NC1=CC=C(C=C1)C1=NNC(O1)=O.O1C=CC(C=C1)=O.Cl>>O=C1C=CN(C=C1)C1=CC=C(C=C1)C1=NNC(O1)=O | [NH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][nH:12][c:13](=[O:14])[o:15]2)[cH:16][cH:17]1.o1[cH:4][cH:3][c:2](=[O:1])[cH:19][cH:18]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[n:11][nH:12][c:13](=[O:14])[o:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1 | Nc1ccc(-c2n[nH]c(=O)o2)cc1.O=c1ccocc1 | O=c1ccn(-c2ccc(-c3n[nH]c(=O)o3)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1ccn(-c2ccc(-c3n[nH]c(=O)o3)cc2)cc1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A mixture of 5-(4-aminophenyl)-1,3,4-oxadiazol-2(3H)-one (0.41 g), 4H-pyran-4-one (0.24 g), and hydrochloric acid (2N, 1.15 ml) in water (25 ml) was stirred under reflux for 3 hours to afford a yellow solid. This solid was added to hot water with stirring and the resulting suspension was made alkaline (pH 8) with aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1nnco1 | HO- | O | null | null | Nc1ccc(-c2n[nH]c(=O)o2)cc1.O=c1ccocc1>O>O=c1ccn(-c2ccc(-c3n[nH]c(=O)o3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1945fdf2a7b44ef385a20f3f04cdd9c1 | C[C@@H]1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>>C[C@@H]1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | N.NC1=CC=C(C=C1)C=1[C@@H](CC(NN1)=O)C.O1C=CC(C=C1)=O.Cl>>C[C@@H]1CC(NN=C1C1=CC=C(C=C1)N1C=CC(C=C1)=O)=O | [CH3:1][C@@H:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:20][cH:21]1.o1[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]1>>[CH3:1][C@@H:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | C[C@@H]1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1 | C[C@@H]1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A mixture of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (100 mg), 4H-pyran-4-one (52 mg) and hydrochloric acid (0.1N, 1 ml) in water (1.3 ml) was stirred under reflux under nitrogen for 3 hours. Aqueous ammonia (880, 0.01 ml) was added to the cooled reaction mixture to afford the title compound which... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | C1=NNCCC1.c1ccccc1.c1ccncc1 | HO- | O | null | null | C[C@@H]1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>O>C[C@@H]1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-99bfe2d0d774438586d35308dbb80cd3 | C[C@H]1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>>C[C@H]1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | NC1=CC=C(C=C1)C=1[C@H](CC(NN1)=O)C.O1C=CC(C=C1)=O.Cl>>C[C@H]1CC(NN=C1C1=CC=C(C=C1)N1C=CC(C=C1)=O)=O | [CH3:1][C@H:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:20][cH:21]1.o1[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]1>>[CH3:1][C@H:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | C[C@H]1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1 | C[C@H]1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | null | null | O | Miscellaneous | OtherReaction | 820fdf5c7d90563efa4f0fcdced261f60cc5772161039256cfa8cd4dfa87d9f6 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:o:[cH;D2;+0:11]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]1:[cH;D2;+0:11]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:5]:[c:6] | null | [] | null | null | null | null | A mixture of (S)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (147 mg), 4H-pyran-4-one (78 mg) and hydrochloric acid (0.1N, 1.5 ml) in water (2 ml) was stirred under reflux under nitrogen for 3 hours. The reaction mixture was cooled to afford the title compound, which was collected, washed with water and d... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccocc1 | c1ccncc1 | C1=NNCCC1.c1ccccc1.c1ccncc1 | HO- | O | null | null | C[C@H]1CC(=O)NN=C1c1ccc(N)cc1.O=c1ccocc1>O>C[C@H]1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6a06c5f7ca494a2a99419033715c3d96 | CC(Cl)C(=O)Cl.Fc1ccccc1>>CC(Cl)C(=O)c1ccc(F)cc1 | ClC(C(=O)Cl)C.[Cl-].[Cl-].[Cl-].[Al+3].FC1=CC=CC=C1>>ClC(C(=O)C1=CC=C(C=C1)F)C | Cl[C:4]([CH:2]([CH3:1])[Cl:3])=[O:5].[cH:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[CH3:1][CH:2]([Cl:3])[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1 | CC(Cl)C(=O)Cl.Fc1ccccc1 | CC(Cl)C(=O)c1ccc(F)cc1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[Cl;D1;H0:5].[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:4]-[C:3](-[Cl;D1;H0:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:8](:[c:7]:[c:6]):[c:9]:[c:10] | null | [] | null | null | 10 | MINUTE | A solution of 2-chloropropionyl chloride (49 ml) in dichloromethane (50 ml) was added to a mixture of anhydrous aluminium trichloride (55.5 g) in dichloromethane (120 ml). The mixture was stirred for 10 minutes at room temperature and then a solution of fluorobenzene (39.5 ml) in dichloromethane (30 ml) was added dropw... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | ClCCl | null | 0.166667 | CC(Cl)C(=O)Cl.Fc1ccccc1>ClCCl>CC(Cl)C(=O)c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d092b65cc0c947de9cedeff753e34adf | CC(Cl)C(=O)c1ccc(F)cc1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(C(=O)OCC)C(C)C(=O)c1ccc(F)cc1 | O.[H-].[Na+].C(CC(=O)OCC)(=O)OCC.ClC(C(=O)C1=CC=C(C=C1)F)C>>C(C)OC(=O)C(C(=O)OCC)C(C)C(C1=CC=C(C=C1)F)=O | Cl[CH:12]([CH3:13])[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH:12]([CH3:13])[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1 | CC(Cl)C(=O)c1ccc(F)cc1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(C(=O)OCC)C(C)C(=O)c1ccc(F)cc1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | ddbfd093676894631592cc1860a2cf8bbaf94b988b30cd6f1e79f06ccf4b2a83 | ee836fe12c6e6643596973ababf2df399dc694362c1c015f4160fe4381ae5166 | c1ccccc1 | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 2 | HOUR | Sodium hydride (50% oil dispersion, 3.5 g) was added with caution to a cooled solution of diethyl malonate (11.85 ml) in dimethylformamide (10 ml). The reaction mixture was stirred at room temperature for 30 minutes before a solution of 2-chloro-1-(4-fluorophenyl)-1-propanone (12.13 g) in dimethylformamide (50 ml) was ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Ester | Ketone.Ester.Ester | null | null | c1ccccc1 | HCl | CN(C=O)C | null | 2 | CC(Cl)C(=O)c1ccc(F)cc1.CCOC(=O)CC(=O)OCC>CN(C=O)C>CCOC(=O)C(C(=O)OCC)C(C)C(=O)c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-25e67d7e720b442a8e013d9e9df27485 | CC(CC(=O)O)C(=O)c1ccc(F)cc1.Oc1ccncc1>>CC(CC(=O)O)C(=O)c1ccc(-n2ccc(=O)cc2)cc1 | Cl.FC1=CC=C(C(=O)C(CC(=O)O)C)C=C1.OC1=CC=NC=C1.[OH-].[Na+]>>O=C1C=CN(C=C1)C1=CC=C(C(=O)C(CC(=O)O)C)C=C1 | F[c:12]1[cH:11][cH:10][c:9]([C:7]([CH:2]([CH3:1])[CH2:3][C:4](=[O:5])[OH:6])=[O:8])[cH:21][cH:20]1.[n:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]1>>[CH3:1][CH:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | CC(CC(=O)O)C(=O)c1ccc(F)cc1.Oc1ccncc1 | CC(CC(=O)O)C(=O)c1ccc(-n2ccc(=O)cc2)cc1 | null | null | O | Acylation | OtherReaction | 4308b383a3710ca54de2d883c53ac81bae07d58b1e4603761dc4ccecde83005c | 9fb0a4734c628f8028aa0d8a5f3520861ccd6e9f72791fbc28874467838ebc37 | O=c1ccn(-c2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[n;H0;D2;+0:10]:[c:11]:[c:12]:1>>[O;H0;D1;+0:6]=[c;H0;D3;+0:7]1:[c:8]:[c:9]:[n;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11]:[c:12]:1 | null | [] | null | null | null | null | A solution of 3-(4-fluorobenzoyl)butanoic acid (8 g), 4-hydroxypridine (8 g) and sodium hydroxide (4.6 g) in water (80 ml) was heated in an autoclave at 140° C. for 20 hours. The reaction mixture was cooled and on acidification to pH3 with dilute hydrochloric acid afforded as a white crystalline precipitate 3-[4-(4-oxo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HF | O | null | null | CC(CC(=O)O)C(=O)c1ccc(F)cc1.Oc1ccncc1>O>CC(CC(=O)O)C(=O)c1ccc(-n2ccc(=O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9082b80c2ce84f57abe9c9a2c56ec958 | CC(CC(=O)O)C(=O)c1ccc(-n2ccc(=O)cc2)cc1.NN>>CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | O.NN.O=C1C=CN(C=C1)C1=CC=C(C(=O)C(CC(=O)O)C)C=C1>>CC1CC(NN=C1C1=CC=C(C=C1)N1C=CC(C=C1)=O)=O | O=[C:8]([CH:2]([CH3:1])[CH2:3][C:4](O)=[O:5])[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1.[NH2:6][NH2:7]>>[CH3:1][CH:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | CC(CC(=O)O)C(=O)c1ccc(-n2ccc(=O)cc2)cc1.NN | CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | null | null | O | Acylation | OtherReaction | 16e715242dd5e92f711d46176c552652cef6c6f4fed9bc9a09a311d5b0b86cea | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C;D1;H3:5])-[C;H0;D3;+0:6](=O)-[c:7](:[c:8]):[c:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[C;D1;H3:5]-[C:4]1-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[N;H0;D2;+0:11]=[C;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | Hydrazine hydrate (1.8 g) was added to a suspension of 3-[4-(4-oxo-1,4-dihydropyridin-1-yl)benzoyl]butanoic acid (5 g) in water (60 ml). The resulting solution was stirred under reflux for 2 hours and cooled to afford the title compound as a pale yellow solid, 4.45 g, m.p. 255°-258° C.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=NNCCC1 | C1=NNCCC1.c1ccccc1.c1ccncc1 | HO- | O | null | null | CC(CC(=O)O)C(=O)c1ccc(-n2ccc(=O)cc2)cc1.NN>O>CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c82a189b0657442b9a6978acdd19952a | CC1CC(=O)NN=C1c1ccc(N)cc1.CN(C)C=CC(=O)C=CN(C)C>>CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | Cl.NC1=CC=C(C=C1)C=1C(CC(NN1)=O)C.CN(C=CC(C=CN(C)C)=O)C.Cl>>CC1CC(NN=C1C1=CC=C(C=C1)N1C=CC(C=C1)=O)=O | [CH3:1][CH:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:20][cH:21]1.CN(C)[CH:14]=[CH:15][C:16](=[O:17])[CH:18]=[CH:19]N(C)C>>[CH3:1][CH:2]1[CH2:3][C:4](=[O:5])[NH:6][N:7]=[C:8]1[c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][cH:15][c:16](=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | CC1CC(=O)NN=C1c1ccc(N)cc1.CN(C)C=CC(=O)C=CN(C)C | CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | d7fdb9b56dbbdcfbb3cd6327379e4f0b769c4b1fbcc6777beb6ca87209d9f4f3 | 0e3cef2991b5837f847176871737a49d675b557a92368f3fc16324e7aa459279 | O=C1CCC(c2ccc(-n3ccc(=O)cc3)cc2)=NN1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-N(-C)-C.[NH2;D1;+0:7]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[O;D1;H0:4]=[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[cH;D2;+0:6]:[cH;D2;+0:5]:1 | null | [] | null | null | 4 | HOUR | A mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (101 mg), 1,5-bis(dimethylamino)-1,4-pentadien-3-one (84 mg) and hydrochloric acid (1N, 0.5 ml) in water (1.5 ml) was stirred at room temperature for 4 hours. More hydrochloric acid (1N, 0.5 ml) was added and the reaction mixture was stirred at room... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Ketone.Primary amine | null | null | c1ccncc1 | C1=NNCCC1.c1ccccc1.c1ccncc1 | Other | O | null | 4 | CC1CC(=O)NN=C1c1ccc(N)cc1.CN(C)C=CC(=O)C=CN(C)C>O>CC1CC(=O)NN=C1c1ccc(-n2ccc(=O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9399f232cbbb4b3389dd35141f07ec6e | CN(C)OC(=O)c1c(O)cccc1-c1cc[nH]n1.COc1cc(OC)nc(S(C)(=O)=O)n1>>COc1cc(OC)nc(Oc2cccc(-c3cc[nH]n3)c2C(=O)ON(C)C)n1 | P(O)(O)(O)=O.[H-].[Na+].N1N=C(C=C1)C=1C(=C(C=CC1)O)C(=O)ON(C)C.CS(=O)(=O)C1=NC(=CC(=N1)OC)OC>>N1N=C(C=C1)C1=CC=CC(=C1C(=O)ON(C)C)OC1=NC(=CC(=N1)OC)OC | [OH:10][c:11]1[cH:12][cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][nH:19][n:20]2)[c:21]1[C:22](=[O:23])[O:24][N:25]([CH3:26])[CH3:27].CS(=O)(=O)[c:9]1[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:... | CN(C)OC(=O)c1c(O)cccc1-c1cc[nH]n1.COc1cc(OC)nc(S(C)(=O)=O)n1 | COc1cc(OC)nc(Oc2cccc(-c3cc[nH]n3)c2C(=O)ON(C)C)n1 | null | null | CN(C=O)C.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 1c345af4a3df0f977c6c030350153f590996fc7a2b6ceaf9fe6cff27648ed228 | 5df75ac15caf6173d8206dd70d45a57321a6ccb2169690bfa04f02c58252d4f1 | c1cnc(Oc2cccc(-c3cc[nH]n3)c2)nc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[O;H0;D2;+0:11]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:12] | null | [] | 30 | CELSIUS | 3 | HOUR | At 10° C., 0.30 g (0.01 mol) of sodium hydride (80% strength) is added to a solution of 2.47 g (10 mmol) of 3-pyrazolyl-2-(N,N-dimethylaminooxycarbonyl)-phenol in 25 ml of anhydrous dimethylformamide, and the reaction mixture is stirred for 3 hours at 30° C. 2.18 g (0.01 mol) of 2-methylsulfonyl-4,6-dimethoxypyrimidine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfone | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1cn[nH]c1 | HO- | CN(C=O)C.O.C(C)(=O)OCC | 30 | 3 | CN(C)OC(=O)c1c(O)cccc1-c1cc[nH]n1.COc1cc(OC)nc(S(C)(=O)=O)n1>CN(C=O)C.O.C(C)(=O)OCC>COc1cc(OC)nc(Oc2cccc(-c3cc[nH]n3)c2C(=O)ON(C)C)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-876c69db2b8146499f39252eada8512a | CON1CN(Cl)CN(OC)C1.O=C(O)c1c(O)cccc1-c1ncc[nH]1.On1cccn1>>CON1CN(OC)CN(Oc2cccc(-c3ncc[nH]3)c2C(=O)On2cccn2)C1 | [H-].[Na+].P(O)(O)(O)=O.N1C(=NC=C1)C=1C=CC=C(C1C(=O)O)O.ClN1CN(CN(C1)OC)OC.ON1N=CC=C1>>N1C(=NC=C1)C1=CC=CC(=C1C(=O)ON1N=CC=C1)ON1CN(CN(C1)OC)OC | Cl[N:9]1[CH2:8][N:5]([O:6][CH3:7])[CH2:4][N:3]([O:2][CH3:1])[CH2:30]1.O[C:22]([c:21]1[c:11]([OH:10])[cH:12][cH:13][cH:14][c:15]1-[c:16]1[n:17][cH:18][cH:19][nH:20]1)=[O:23].[OH:24][n:25]1[cH:26][cH:27][cH:28][n:29]1>>[CH3:1][O:2][N:3]1[CH2:4][N:5]([O:6][CH3:7])[CH2:8][N:9]([O:10][c:11]2[cH:12][cH:13][cH:14][c:15](-[c:1... | CON1CN(Cl)CN(OC)C1.O=C(O)c1c(O)cccc1-c1ncc[nH]1.On1cccn1 | CON1CN(OC)CN(Oc2cccc(-c3ncc[nH]3)c2C(=O)On2cccn2)C1 | null | null | O1CCCC1 | Acylation | OtherReaction | 08455edd162739111984b8a1914303a6c0284315761e8cf3e5624a1ddcc7dbe0 | f4525ecd0571b2e0c099853d5f1894c98844f63a04a7bcf4433c9de4b57a1c02 | O=C(On1cccn1)c1c(ON2CNCNC2)cccc1-c1ncc[nH]1 | Cl-[N;H0;D3;+0:1]1-[C:2]-[#7:3](-[#8:4])-[C:5]-[#7:6](-[#8:7])-[C:8]-1.O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](-[OH;D1;+0:14]):[c:15].[#7;a:16]:[#7;a:17](-[OH;D1;+0:18]):[c:19]>>[#7;a:16]:[#7;a:17](-[O;H0;D2;+0:18]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13](-[O;H0;D2;+0:14]-[N;H0;D3;+0:1]1-[C:2... | null | [] | null | null | 30 | MINUTE | 1.75 g (10.8 mmol) of N,N'-carbonylbisimidazole is added to a solution of 1.88 g (10 mmol) of 6-imidazolylsalicylic acid in 30 ml of tetrahydrofuran. After the mixture has been stirred for 30 minutes at room temperature, 9.9 mmol of N-hydroxypyrazole is added and the mixture is stirred for a further 14 hours. The react... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Tertiary amine | Tertiary amine | C1[NH]C[NH]C[NH]1 | C1[NH]C[NH]C[NH]1 | C1[NH]C[NH]C[NH]1.c1ccccc1.c1c[nH]cn1.c1cn[nH]c1 | HCl | O1CCCC1 | null | 0.5 | CON1CN(Cl)CN(OC)C1.O=C(O)c1c(O)cccc1-c1ncc[nH]1.On1cccn1>O1CCCC1>CON1CN(OC)CN(Oc2cccc(-c3ncc[nH]3)c2C(=O)On2cccn2)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-774ce888c2ae4a3eb24f6b6510e760c5 | Clc1cnc2ccccc2n1.[SH-]>>Sc1cnc2ccccc2n1 | ClC1=NC2=CC=CC=C2N=C1.[SH-].[Na+]>>SC1=NC2=CC=CC=C2N=C1 | Cl[c:2]1[cH:3][n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11]1.[SH-:1]>>[SH:1][c:2]1[cH:3][n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11]1 | Clc1cnc2ccccc2n1.[SH-] | Sc1cnc2ccccc2n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 618526068c98548f3e33251e238323468f68913857bd4da8b171e44c07719770 | 5acfc94bcb91f90cc14ddd9f791d64cf2f45381ebe181eac63cc3d2843bb00cd | c1ccc2nccnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[SH-;D0:7]>>[SH;D1;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 157.3 | [{"value": 157.3, "product": "SC1=NC2=CC=CC=C2N=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | 2-Chloroquinoxaline (2 g) and sodium hydrosulphide (1.23 g) were stirred together in 25 ml of dimethylformamide and heated to 100° C. After 3 hours the reaction mixture was allowed to cool and then partitioned between 70 ml of water and 30 ml of ethyl acetate. The organic layer was separated and the aqueous layer extra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic thiol | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | Other | CN(C=O)C | 100 | 3 | Clc1cnc2ccccc2n1.[SH-]>CN(C=O)C>Sc1cnc2ccccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7070d8bc971546909aeafe6e08288d5c | Cc1nc2ccccc2nc1O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>Cc1nc2ccccc2nc1S | OC1=NC2=CC=CC=C2N=C1C.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>SC1=NC2=CC=CC=C2N=C1C | O[c:11]1[c:2]([CH3:1])[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:12])(S2)S3>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10][c:11]1[SH:12] | Cc1nc2ccccc2nc1O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | Cc1nc2ccccc2nc1S | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 6b70c18a601c3d520a3f9bcb8a7122f0554a354c356ace9bcfabb77b02d4a672 | 5064cd713f52475d9702bad414c4e5aaac7fac3150d286577c363bca18bdbe15 | c1ccc2nccnc2c1 | O-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:8])(-S-2)-S-3>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[SH;D1;+0:8] | null | [] | null | null | null | null | 2-Hydroxy-3-methylquinoxaline (2 g) and phosphorus pentasulphide (3.05 g) were stirred together in 40 ml of pyridine and the reaction mixture heated to reflux.
Conditions: See reaction.notes.procedure_details.
Workup: the reaction mixture heated to reflux | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Aromatic thiol | c1ccc2nccnc2c1.S1P2SP3SP1SP(S2)S3 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | Other | N1=CC=CC=C1 | null | null | Cc1nc2ccccc2nc1O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>Cc1nc2ccccc2nc1S |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d5edec4fc25d4165a206856d008fcc0a | CCOC(=O)CBr.Nc1ccc(F)cc1>>CCN(CC(=O)O)c1ccc(F)cc1 | FC1=CC=C(N)C=C1.C([O-])([O-])=O.[K+].[K+].C1COCCOCCOCCOCCOCCO1.C(C)OC(CBr)=O>>C(C)N(CC(=O)O)C1=CC=C(C=C1)F | Br[CH2:4][C:5](=[O:6])[O:7][CH2:2][CH3:1].[NH2:3][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][N:3]([CH2:4][C:5](=[O:6])[OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1 | CCOC(=O)CBr.Nc1ccc(F)cc1 | CCN(CC(=O)O)c1ccc(F)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3d32c7244697cf6aa13f97f5b44e896f7d6e28dca4be367d4c8a70a634f7354e | 8557e77f434d58647556c853429bbd1304f785e81ed25dd3b19413e60d2746ad | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH2;D2;+0:5]-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[CH2;D2;+0:5]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | 4-Fluoroaniline (5 g), potassium carbonate (3.11 g) and a catalytic amount of 18-Crown-6 were stirred together in 50 ml of ethanol. A solution of ethylbromoacetate (7.52 g) in 25 ml of ethanol was added dropwise and the reaction was heated to reflux.
Conditions: See reaction.notes.procedure_details.
Workup: the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Carboxylic acid.Tertiary amine | null | null | c1ccccc1 | HBr | C(C)O | null | null | CCOC(=O)CBr.Nc1ccc(F)cc1>C(C)O>CCN(CC(=O)O)c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a3390456313144aa978257dac6d1ec7e | CS(=O)(=O)c1nc(N)n2nc(-c3ccco3)nc2n1.Nc1nc(NCCc2ccc(O)cc2)nc2nc(-c3ccco3)nn12>>Nc1nc(NCCc2ccc(Oc3nc(N)n4nc(-c5ccco5)nc4n3)cc2)nc2nc(-c3ccco3)nn12 | C(Cl)Cl.CO.NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)NCCC2=CC=C(C=C2)O.N12CCCCCC2=NCCC1.NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)S(=O)(=O)C>>NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)OC2=CC=C(C=C2)CCNC2=NC=1N(C(=N2)N)N=C(N1)C=1OC=CC1 | CS(=O)(=O)[c:13]1[n:14][c:15]([NH2:16])[n:17]2[n:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][o:24]3)[n:25][c:26]2[n:27]1.[NH2:1][c:2]1[n:3][c:4]([NH:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:28][cH:29]2)[n:30][c:31]2[n:32][c:33](-[c:34]3[cH:35][cH:36][cH:37][o:38]3)[n:39][n:40]12>>[NH2:1][c:2]1[n:3][c:4]([NH:5]... | CS(=O)(=O)c1nc(N)n2nc(-c3ccco3)nc2n1.Nc1nc(NCCc2ccc(O)cc2)nc2nc(-c3ccco3)nn12 | Nc1nc(NCCc2ccc(Oc3nc(N)n4nc(-c5ccco5)nc4n3)cc2)nc2nc(-c3ccco3)nn12 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 4f28b727ad8941dcd3a706875a7132829b3fbbba254eec3154abc670bf3ca2d6 | 5df75ac15caf6173d8206dd70d45a57321a6ccb2169690bfa04f02c58252d4f1 | c1coc(-c2nc3nc(NCCc4ccc(Oc5ncn6nc(-c7ccco7)nc6n5)cc4)ncn3n2)c1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[#7;a:9]:1.[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[#7;a:9]:1):[c:13] | null | [] | null | null | null | null | 7-amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine (0.91 g) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 0.37 ml) were added to a suspension of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine (0.82 g) in acetonitrile (50 ml) and the resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfone | Ether | c1ncn2ncnc2n1 | c1ncn2ncnc2n1 | c1ccccc1.c1ncn2ncnc2n1.c1ccoc1.c1ncn2ncnc2n1.c1ccoc1 | HO- | C(C)#N | null | null | CS(=O)(=O)c1nc(N)n2nc(-c3ccco3)nc2n1.Nc1nc(NCCc2ccc(O)cc2)nc2nc(-c3ccco3)nn12>C(C)#N>Nc1nc(NCCc2ccc(Oc3nc(N)n4nc(-c5ccco5)nc4n3)cc2)nc2nc(-c3ccco3)nn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-263a470489eb4f31aa2b7a9416d2c743 | CSC(=NC#N)SC.Nc1n[nH]c(-c2ccco2)n1>>CSc1nc(N)n2nc(-c3ccco3)nc2n1 | NC1=NNC(=N1)C=1OC=CC1.CSC(=NC#N)SC>>NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)SC | CS[C:3]([S:2][CH3:1])=[N:4][C:5]#[N:6].[n:7]1[nH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][o:14]2)[n:15][c:16]1[NH2:17]>>[CH3:1][S:2][c:3]1[n:4][c:5]([NH2:6])[n:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][o:14]3)[n:15][c:16]2[n:17]1 | CSC(=NC#N)SC.Nc1n[nH]c(-c2ccco2)n1 | CSc1nc(N)n2nc(-c3ccco3)nc2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 566500fbfb455ebdfa23274308e3d530174cbc8eff3f50b1f36552a70387f76f | 81955634976ddffb98b1dc0b18f40adc0b0fe8c65fec77cb19d2966e57d60ed0 | c1coc(-c2nc3ncncn3n2)c1 | C-S-[C;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3])=[N;H0;D2;+0:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6].[#8;a:7]:[c:8]-[c:9]1:[#7;a:10]:[c:11](-[NH2;D1;+0:12]):[n;H0;D2;+0:13]:[nH;D2;+0:14]:1>>[#8;a:7]:[c:8]-[c:9]1:[#7;a:10]:[c:11]2:[n;H0;D2;+0:12]:[c;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3]):[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[NH2;D1;+0:6]):[n;H0;... | 20.3 | [{"value": 20.3, "product": "NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | null | null | An intimate mixture of 3-amino-5-(2-furyl)-1,2,4-triazole (33.0 g) and dimethyl N-cyanodithioiminocarbonate (33.0 g) was heated at 170° C. for 1 hour, under a slow stream of argon. After cooling, the resulting solid was purified by column chromatography on silica (600 g) eluting with an increasing amount of ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Monosulfide.Monosulfide | Primary amine.Monosulfide | c1nc[nH]n1 | c1ncn2ncnc2n1 | c1ncn2ncnc2n1.c1ccoc1 | Other | null | 170 | null | CSC(=NC#N)SC.Nc1n[nH]c(-c2ccco2)n1>>CSc1nc(N)n2nc(-c3ccco3)nc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-77c7e60be0494129bd4ab11177e4baf3 | Nc1nc(NCc2ccc(OCc3ccccc3)cc2)nc2nc(-c3ccco3)nn12>>Nc1nc(NCc2ccc(O)cc2)nc2nc(-c3ccco3)nn12 | NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)NCC2=CC=C(C=C2)OCC2=CC=CC=C2>>NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)NCC2=CC=C(C=C2)O | c1ccc(C[O:11][c:10]2[cH:9][cH:8][c:7]([CH2:6][NH:5][c:4]3[n:3][c:2]([NH2:1])[n:24]4[c:15]([n:14]3)[n:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][o:22]3)[n:23]4)[cH:13][cH:12]2)cc1>>[NH2:1][c:2]1[n:3][c:4]([NH:5][CH2:6][c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]2)[n:14][c:15]2[n:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][o... | Nc1nc(NCc2ccc(OCc3ccccc3)cc2)nc2nc(-c3ccco3)nn12 | Nc1nc(NCc2ccc(O)cc2)nc2nc(-c3ccco3)nn12 | null | [Pd] | CO.C(C)(=O)OCC | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CNc2ncn3nc(-c4ccco4)nc3n2)cc1 | [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] | null | [] | null | null | null | null | A solution of 7-amino-5-[(4-benzyloxyphenyl)methyl]amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine (2.37 g) in ethyl acetate (150 ml) and methanol (150 ml) was treated with 10% palladium on carbon (3.0 g) and hydrogenated at atmospheric pressure for 2.5 hours. The catalyst was filtered through diatomaceous eart... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ncn2ncnc2n1.c1ccoc1 | Other | [Pd].CO.C(C)(=O)OCC | null | null | Nc1nc(NCc2ccc(OCc3ccccc3)cc2)nc2nc(-c3ccco3)nn12>[Pd].CO.C(C)(=O)OCC>Nc1nc(NCc2ccc(O)cc2)nc2nc(-c3ccco3)nn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b75301676eb1424c9eacfe2ac252c8f5 | Nc1nc(NCCc2ccccc2OCc2ccccc2)nc2nc(-c3ccco3)nn12>>Nc1nc(NCCc2ccccc2O)nc2nc(-c3ccco3)nn12 | NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)NCCC2=C(C=CC=C2)OCC2=CC=CC=C2.[H][H]>>NC1=NC(=NC=2N1N=C(N2)C=2OC=CC2)NCCC2=C(C=CC=C2)O | c1ccc(C[O:14][c:13]2[c:8]([CH2:7][CH2:6][NH:5][c:4]3[n:3][c:2]([NH2:1])[n:25]4[c:16]([n:15]3)[n:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][o:23]3)[n:24]4)[cH:9][cH:10][cH:11][cH:12]2)cc1>>[NH2:1][c:2]1[n:3][c:4]([NH:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[OH:14])[n:15][c:16]2[n:17][c:18](-[c:19]3[cH:20][c... | Nc1nc(NCCc2ccccc2OCc2ccccc2)nc2nc(-c3ccco3)nn12 | Nc1nc(NCCc2ccccc2O)nc2nc(-c3ccco3)nn12 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCNc2ncn3nc(-c4ccco4)nc3n2)cc1 | [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] | null | [] | null | null | null | null | A solution of the product of step (1) (0.9g) in methanol (150 ml) was hydrogenated at room-temperature and pressure using 10% palladium on carbon (0.9 g) catalyst. After the uptake of hydrogen was complete, the catalyst was filtered off and the solvent evaporated. The residue was crystallised from ethanol, and gave 7-a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ncn2ncnc2n1.c1ccoc1 | Other | [Pd].CO | null | null | Nc1nc(NCCc2ccccc2OCc2ccccc2)nc2nc(-c3ccco3)nn12>[Pd].CO>Nc1nc(NCCc2ccccc2O)nc2nc(-c3ccco3)nn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ac2c06d7cbfb4525b6d01a68903c4d4b | O=C1Nc2ccccc2SC1c1ccc(F)cc1>>Fc1ccc(C2CNc3ccccc3S2)cc1 | FC1=CC=C(C=C1)C1SC2=C(NC1=O)C=CC=C2.[BH4-].[Na+].C([O-])([O-])=O.[K+].[K+].Cl>>FC1=CC=C(C=C1)C1SC2=C(NC1)C=CC=C2 | O=[C:7]1[CH:6]([c:5]2[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]2)[S:15][c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[NH:8]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][NH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[S:15]2)[cH:16][cH:17]1 | O=C1Nc2ccccc2SC1c1ccc(F)cc1 | Fc1ccc(C2CNc3ccccc3S2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 1dcd93b688ffb5a97304eaeb9d3e97c68c92ef37b3351d43b5078fead2422b3b | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(C2CNc3ccccc3S2)cc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[c:3]:[c:4]-[#16:5]-[C:6]-1-[c:7]>>[c:7]-[C:6]1-[#16:5]-[c:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-1 | 91.2 | [{"value": 91.0, "product": "FC1=CC=C(C=C1)C1SC2=C(NC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "FC1=CC=C(C=C1)C1SC2=C(NC1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine (4.0 g), sodium borohydride (2.91 g) and tetrahydrofuran (100 ml) is added dropwise with stirring boron trifluoride etherate complex (12. 5 ml) at room temperature, and the mixture is refluxed for 1.5 hour. After cooling, to the mixture is added ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)NCCS2 | c1ccccc1.c1ccc2c(c1)NCCS2 | Other | O1CCCC1 | null | null | O=C1Nc2ccccc2SC1c1ccc(F)cc1>O1CCCC1>Fc1ccc(C2CNc3ccccc3S2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d89b6b0a42ba47e2b52fd965ff8e6b9b | C=CC(=O)Cl.Clc1ccc(C2CNc3ccccc3S2)cc1>>C=CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | C(C=C)(=O)Cl.ClC1=CC=C(C=C1)C1SC2=C(NC1)C=CC=C2.C(O)([O-])=O.[Na+].O>>ClC1=CC=C(C=C1)C1SC2=C(N(C1)C(C=C)=O)C=CC=C2 | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | C=CC(=O)Cl.Clc1ccc(C2CNc3ccccc3S2)cc1 | C=CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 4ce9986a2e7f31aa9eaa0925622c2cb2cd91fbaa9d58585e0420c051b9143356 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(C2CNc3ccccc3S2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[c:5]:[c:6]1:[c:7]-[#16:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H2:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#16:8]-[c:7]:[c:6]-1:[c:5] | 93 | [{"value": 93.0, "product": "ClC1=CC=C(C=C1)C1SC2=C(N(C1)C(C=C)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "ClC1=CC=C(C=C1)C1SC2=C(N(C1)C(C=C)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a mixture of 2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (9.62 g), sodium hydrogen carbonate (6.0 g), methylene chloride (100 ml) and water (50 ml) is added dropwise with stirring a solution of acryloyl chloride (5.0 g) in methylene chloride (20 ml) under ice cooling over a period of about 30 minutes. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)[NH]CCS2 | c1ccccc1.c1ccc2c(c1)[NH]CCS2 | HCl | C(Cl)Cl | null | 3 | C=CC(=O)Cl.Clc1ccc(C2CNc3ccccc3S2)cc1>C(Cl)Cl>C=CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 |
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