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-e04cbcb18b1d47e8b7a7115f33cccf17 | Cc1ccsc1C(=O)O.O=C(Cl)C(=O)Cl>>Cc1ccsc1C(=O)Cl | CC1=C(SC=C1)C(=O)O.C(C(=O)Cl)(=O)Cl>>CC1=C(SC=C1)C(=O)Cl | O[C:7]([c:6]1[c:2]([CH3:1])[cH:3][cH:4][s:5]1)=[O:8].O=C(Cl)C(=O)[Cl:9]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[C:7](=[O:8])[Cl:9] | Cc1ccsc1C(=O)O.O=C(Cl)C(=O)Cl | Cc1ccsc1C(=O)Cl | null | null | C1=CC=CC=C1 | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccsc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 100.3 | [{"value": 100.3, "product": "CC1=C(SC=C1)C(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 100 ml of benzene was suspended 3.00 g (21.1 mmol) of 3-methyl-2-thiophenecarboxylic acid, oxalyl chloride [7.36 ml (84.4 mmol)] was added and the mixture was refluxed for 2 hours. After cooling, the solvent was distilled off to obtain 3.40 g of 3-methylthenoyl chloride (yield: quant.). To a solution of 1.50 g (6.23... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccsc1 | HCl | C1=CC=CC=C1 | null | null | Cc1ccsc1C(=O)O.O=C(Cl)C(=O)Cl>C1=CC=CC=C1>Cc1ccsc1C(=O)Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f56f6d364c6f42abae9c794c891f57f9 | Cc1ccsc1C(=O)Cl.NCCCSc1ccncc1>>Cc1ccsc1C(=O)NCCCSc1ccncc1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.CC1=C(SC=C1)C(=O)Cl>>CC1=C(SC=C1)C(=O)NCCCSC1=CC=NC=C1 | Cl[C:7]([c:6]1[c:2]([CH3:1])[cH:3][cH:4][s:5]1)=[O:8].[NH2:9][CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | Cc1ccsc1C(=O)Cl.NCCCSc1ccncc1 | Cc1ccsc1C(=O)NCCCSc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1cccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 84.5 | [{"value": 84.5, "product": "CC1=C(SC=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "CC1=C(SC=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 100 ml of benzene was suspended 3.00 g (21.1 mmol) of 3-methyl-2-thiophenecarboxylic acid, oxalyl chloride [7.36 ml (84.4 mmol)] was added and the mixture was refluxed for 2 hours. After cooling, the solvent was distilled off to obtain 3.40 g of 3-methylthenoyl chloride (yield: quant.). To a solution of 1.50 g (6.23... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | Cc1ccsc1C(=O)Cl.NCCCSc1ccncc1>C(Cl)Cl>Cc1ccsc1C(=O)NCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c3e25c8a85d44ea5a75bc8f82e1e111d | CCN(CC)CC.CN(C)C(=O)Sc1cccnc1.CO>>O=C1c2ccccc2C(=O)N1CSc1cccnc1 | CN(C(=O)SC=1C=NC=CC1)C.[OH-].[Na+].CO.C(C)N(CC)CC>>C1(C=2C(C(N1CSC=1C=NC=CC1)=O)=CC=CC2)=O | C(N([CH2:4][CH3:3])[CH2:7][CH3:6])[CH3:5].[O:1]=[C:2]([N:11]([CH3:8])[CH3:12])[S:13][c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1.[CH3:9][OH:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][S:13][c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1 | CCN(CC)CC.CN(C)C(=O)Sc1cccnc1.CO | O=C1c2ccccc2C(=O)N1CSc1cccnc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | f6e1d45e9221ee6e026b35747c95fb0c38d15ea43d755f8997202c8b68cc288f | 0eafb27fde53390e73581c39f563745aa9ec1ae457b9845f07dfd55c08d54d24 | O=C1c2ccccc2C(=O)N1CSc1cccnc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-N(-C-[CH3;D1;+0:3])-[CH2;D2;+0:4]-[CH3;D1;+0:5].[CH3;D1;+0:6]-[N;H0;D3;+0:7](-[CH3;D1;+0:8])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[S;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]:[#7;a:15]:[c:16].[CH3;D1;+0:17]-[OH;D1;+0:18]>>[O;D1;H0:10]=[C;H0;D3;+0:9]1-[N;H0;D3;+0:7](-[CH2;D2;+0:6]-[S;H0;D2;+0:11]-[c:12](:... | 80.9 | [{"value": 80.9, "product": "C1(C=2C(C(N1CSC=1C=NC=CC1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 1.00 g (5.49 mmol) of 3-(dimethylaminocarbonylthio)pyridine in 50 ml of methanol, 5.49 ml (5.49 mmol) of a 1N aqueous solution of sodium hydroxide was added. The mixture was heated at 60° C. for 1 hour with stirring. After cooling, the solvent was distilled off. The residue was dissolved in ethanol and... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amine.Monosulfide.Methanol | Substituted dicarboximide.Monosulfide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | Other | C(C)O | 60 | null | CCN(CC)CC.CN(C)C(=O)Sc1cccnc1.CO>C(C)O>O=C1c2ccccc2C(=O)N1CSc1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dd7bd97cca9b4017bd4ae008bd7dac34 | O=C1c2ccccc2C(=O)N1CCl.Oc1ccncc1>>O=C1c2ccccc2C(=O)N1COc1ccncc1 | OC1=CC=NC=C1.ClCN1C(C=2C(C1=O)=CC=CC2)=O.C1CCC2=NCCCN2CC1>>C1(C=2C(C(N1COC1=CC=NC=C1)=O)=CC=CC2)=O | Cl[CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[OH:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][O:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | O=C1c2ccccc2C(=O)N1CCl.Oc1ccncc1 | O=C1c2ccccc2C(=O)N1COc1ccncc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fdeaab08fdcfd316930ef1175816bd95f7da676fa892aa1cc7c464d4492570d3 | fecbd7b649db84f1531203fbcee385caf3cdb6e47086797236a63b91a6e50ba8 | O=C1c2ccccc2C(=O)N1COc1ccncc1 | Cl-[CH2;D2;+0:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]-[C:7]-1=[O;D1;H0:8].[OH;D1;+0:9]-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[O;D1;H0:8]=[C:7]1-[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#7:2]-1-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1 | 21 | [{"value": 21.0, "product": "C1(C=2C(C(N1COC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.0, "product": "C1(C=2C(C(N1COC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 10.76 g (55 mmol) of N-chloromethylphthalimide in 80 ml of DMF, 8.23 ml (55 mmol) of 1,8-diazabicyclo[5,4,0]-7-undecene was added. The mixture was stirred at room temperature for 2 hours. After the solvent was distilled off, the reaction mixture was poured into... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Substituted dicarboximide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HCl | CN(C)C=O | null | 2 | O=C1c2ccccc2C(=O)N1CCl.Oc1ccncc1>CN(C)C=O>O=C1c2ccccc2C(=O)N1COc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-80d6d35a6b1b4822a93a6f325c74f83a | NCc1cccs1.OCCCSc1ccncc1>>c1csc(CNCCCSc2ccncc2)c1 | OCCCSC1=CC=NC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl.S1C(=CC=C1)CN>>S1C(=CC=C1)CNCCCSC1=CC=NC=C1 | [cH:1]1[cH:2][s:3][c:4]([CH2:5][NH2:6])[cH:17]1.O[CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[cH:1]1[cH:2][s:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][CH2:9][S:10][c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[cH:17]1 | NCc1cccs1.OCCCSc1ccncc1 | c1csc(CNCCCSc2ccncc2)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1csc(CNCCCSc2ccncc2)c1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[#16;a:4]:[c:5]-[C:6]-[NH2;D1;+0:7]>>[#16;a:4]:[c:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3] | 29.1 | [{"value": 29.1, "product": "S1C(=CC=C1)CNCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.1, "product": "S1C(=CC=C1)CNCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In 200 ml of methylene chloride were dissolved 10.34 g (61.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 10.2 ml (73.3 mmol) of triethylamine, methanesulfonyl chloride [5.7 ml (73.3 mmol)] was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1ccsc1.c1ccncc1 | HO- | C(Cl)Cl | null | 0.5 | NCc1cccs1.OCCCSc1ccncc1>C(Cl)Cl>c1csc(CNCCCSc2ccncc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6ab3399bbe384df4a016cb4e27a3ec16 | Nc1ncccc1CCN1C(=O)c2ccccc2C1=O>>Nc1ncccc1CCN1C(=O)c2ccccc2C1=O | Cl.NC1=NC=CC=C1CCN1C(C=2C(C1=O)=CC=CC2)=O>>Cl.NC1=NC=CC=C1CCN1C(C=2C(C1=O)=CC=CC2)=O | [NH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21]>>[NH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21] | Nc1ncccc1CCN1C(=O)c2ccccc2C1=O | Nc1ncccc1CCN1C(=O)c2ccccc2C1=O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1c2ccccc2C(=O)N1CCc1cccnc1 | null | 79 | [{"value": 79.0, "product": "Cl.NC1=NC=CC=C1CCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In 5 ml of methanol was dissolved 237 mg (0.792 mmol) of 2-amino-3-[2-(phthalimido)ethyl]pyridine. The solution was treated with 5 ml (10 mmol) of a 2N solution of hydrogen chloride in methanol. The solvent was distilled off to obtain the desired powder. The powder thus obtained was washed with ether to obtain 233 mg o... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.c1ccc2c(c1)C[NH]C2 | null | CO | null | null | Nc1ncccc1CCN1C(=O)c2ccccc2C1=O>CO>Nc1ncccc1CCN1C(=O)c2ccccc2C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-78e604ab97a5457d90db9847ffc8eaa3 | OCCCBr.Sc1ccncc1>>OCCCSc1ccncc1 | SC1=CC=NC=C1.C(C)N(CC)CC.BrCCCO>>OCCCSC1=CC=NC=C1 | Br[CH2:4][CH2:3][CH2:2][OH:1].[SH:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[OH:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | OCCCBr.Sc1ccncc1 | OCCCSc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 62.9 | [{"value": 62.9, "product": "OCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.9, "product": "OCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | In 250 ml of methylene chloride was dissolved 22.2 g (200 mmol) of 4-mercaptopyridine and 27.9 ml (200 mmol) of triethylamine. Thereto was added 18.1 g (200 mmol) of 3-bromo-1-propanol. The mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with a 1N aqueous solution of sodium hydroxid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1 | HBr | C(Cl)Cl | null | 3 | OCCCBr.Sc1ccncc1>C(Cl)Cl>OCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cead92d510b44868b7a17bfdcce47e62 | NCc1ccccc1.OCCCSc1ccncc1>>c1ccc(CNCCCSc2ccncc2)cc1 | C(C1=CC=CC=C1)N.OCCCSC1=CC=NC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C1=CC=CC=C1)NCCCSC1=CC=NC=C1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:17][cH:18]1.O[CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][CH2:9][S:10][c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][cH:18]1 | NCc1ccccc1.OCCCSc1ccncc1 | c1ccc(CNCCCSc2ccncc2)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1ccc(CNCCCSc2ccncc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[C:5]-[c:6] | 16.1 | [{"value": 16.1, "product": "C(C1=CC=CC=C1)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.1, "product": "C(C1=CC=CC=C1)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In 150 ml of methylene chloride were dissolved 5.22 g (30.8 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.16 ml (37.0 mmol) of triethylamine, methanesulfonyl chloride [2.86 ml (37.0 mmol)] was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1 | HO- | C(Cl)Cl | null | 0.5 | NCc1ccccc1.OCCCSc1ccncc1>C(Cl)Cl>c1ccc(CNCCCSc2ccncc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a2293b8478224028b214fce323cd3c06 | CC(=O)Cl.c1ccc(CNCCCSc2ccncc2)cc1>>CC(=O)N(CCCSc1ccncc1)Cc1ccccc1 | C(C1=CC=CC=C1)NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C)(=O)Cl>>C(C1=CC=CC=C1)N(C(C)=O)CCCSC1=CC=NC=C1 | Cl[C:2]([CH3:1])=[O:3].[NH:4]([CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][C:2](=[O:3])[N:4]([CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CC(=O)Cl.c1ccc(CNCCCSc2ccncc2)cc1 | CC(=O)N(CCCSc1ccncc1)Cc1ccccc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(CNCCCSc2ccncc2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[c:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7]-[c:8])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 84.3 | [{"value": 84.2, "product": "C(C1=CC=CC=C1)N(C(C)=O)CCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.3, "product": "C(C1=CC=CC=C1)N(C(C)=O)CCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.0 g (3.87 mmol) of 4-[3-(N-benzylamino)propylthio)-pyridine and 0.65 ml (4.64 mmol) of triethylamine in 25 ml of methylene chloride, 0.49 ml (4.64 mmol) of acetyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | CC(=O)Cl.c1ccc(CNCCCSc2ccncc2)cc1>C(Cl)Cl>CC(=O)N(CCCSc1ccncc1)Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d1810d5f436433ea51dce05a3b95637 | O=C(Cl)c1ccccc1.c1ccc(CNCCCSc2ccncc2)cc1>>O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccc1 | Cl.Cl.C(C1=CC=CC=C1)NCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>Cl.C(C1=CC=CC=C1)N(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1 | Cl[C:3](=[O:2])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[NH:10]([CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1)[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[O:2]=[C:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]([CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1)[CH... | O=C(Cl)c1ccccc1.c1ccc(CNCCCSc2ccncc2)cc1 | O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[c:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[c:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 50.4 | [{"value": 50.4, "product": "Cl.C(C1=CC=CC=C1)N(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.6, "product": "Cl.C(C1=CC=CC=C1)N(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 400 mg (1.21 mmol) of 4-[3-(N-benzylamino)propylthio] pyridine dihydrochloride and 0.55 ml (4.00 mmol) of triethylamine in 5 ml of methylene chloride, 0.17 ml (1.45 mmol) of benzoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | O=C(Cl)c1ccccc1.c1ccc(CNCCCSc2ccncc2)cc1>C(Cl)Cl>O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9a9a1fc08b224050b6bc9bda7fc64182 | NCc1ccccn1.OCCCSc1ccncc1>>c1ccc(CNCCCSc2ccncc2)nc1 | NCC1=NC=CC=C1.OCCCSC1=CC=NC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>N1=C(C=CC=C1)CNCCCSC1=CC=NC=C1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[n:17][cH:18]1.O[CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][CH2:9][S:10][c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[n:17][cH:18]1 | NCc1ccccn1.OCCCSc1ccncc1 | c1ccc(CNCCCSc2ccncc2)nc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1ccc(CNCCCSc2ccncc2)nc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]-[C:6]-[NH2;D1;+0:7]>>[#7;a:4]:[c:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3] | 25.4 | [{"value": 25.4, "product": "N1=C(C=CC=C1)CNCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.4, "product": "N1=C(C=CC=C1)CNCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 5.26 g (31.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.20 ml (37.3 mmol) of triethylamine in 150 ml of methylene chloride, 2.90 ml (37.3 mmol) of methanesulfonyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccncc1 | HO- | C(Cl)Cl | 80 | null | NCc1ccccn1.OCCCSc1ccncc1>C(Cl)Cl>c1ccc(CNCCCSc2ccncc2)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c1f38a3c62784772a0ad020614ddd68f | CC(=O)Cl.c1ccc(CNCCCSc2ccncc2)nc1>>CC(=O)N(CCCSc1ccncc1)Cc1ccccn1 | N1=C(C=CC=C1)CNCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C)(=O)Cl>>N1=C(C=CC=C1)CN(C(C)=O)CCCSC1=CC=NC=C1 | Cl[C:2]([CH3:1])=[O:3].[NH:4]([CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][n:21]1>>[CH3:1][C:2](=[O:3])[N:4]([CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][n:21]1 | CC(=O)Cl.c1ccc(CNCCCSc2ccncc2)nc1 | CC(=O)N(CCCSc1ccncc1)Cc1ccccn1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(CNCCCSc2ccncc2)nc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[#7;a:4]:[c:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 85.6 | [{"value": 85.6, "product": "N1=C(C=CC=C1)CN(C(C)=O)CCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "N1=C(C=CC=C1)CN(C(C)=O)CCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.62 g (6.24 mmol) of 4-[3-(N-2pyridylmethylamino)propylthio]pyridine and 1.10 ml (7.80 mmol) of triethylamine in 10 ml of methylene chloride, 0.51 ml (7.80 mmol) of acetyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccncc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | CC(=O)Cl.c1ccc(CNCCCSc2ccncc2)nc1>C(Cl)Cl>CC(=O)N(CCCSc1ccncc1)Cc1ccccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f6517c3bd51c417b92bd4b78dfc8e915 | O=C(Cl)c1ccccc1.c1ccc(CNCCCSc2ccncc2)nc1>>O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccn1 | N1=C(C=CC=C1)CNCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>N1=C(C=CC=C1)CN(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[NH:9]([CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1)[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][n:26]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]([CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1)[CH2:2... | O=C(Cl)c1ccccc1.c1ccc(CNCCCSc2ccncc2)nc1 | O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccn1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 58.9 | [{"value": 58.9, "product": "N1=C(C=CC=C1)CN(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.9, "product": "N1=C(C=CC=C1)CN(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.60 g (6.17 mmol) of 4-[3-(N-2-pyridylmethylamino)propylthio)pyridine and 1.05 ml (7.40 mmol) of triethylamine in 10 ml of methylene chloride, 0.86 ml (7.40 mmol) of benzoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | O=C(Cl)c1ccccc1.c1ccc(CNCCCSc2ccncc2)nc1>C(Cl)Cl>O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1ccccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9416feec1e0e4637adb9bb2ca9dd4492 | O=C1c2ccccc2C(=O)N1CCCBr.Oc1ccncc1>>O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | OC1=CC=NC=C1.BrCCCN1C(C=2C(C1=O)=CC=CC2)=O.C1CCC2=NCCCN2CC1>>C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O | Br[CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[OH:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | O=C1c2ccccc2C(=O)N1CCCBr.Oc1ccncc1 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 16.4 | [{"value": 16.4, "product": "C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.4, "product": "C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 14.75 g (55 mmol) of N-(3-bromopropyl)phthalimide in 80 ml of DMF was added 8.23 ml (55 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene. The mixture was stirred at room temperature for 6 hours. After the solvent was distilled off, the mixture was poured into water ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HBr | CN(C)C=O | null | 6 | O=C1c2ccccc2C(=O)N1CCCBr.Oc1ccncc1>CN(C)C=O>O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8ddd5dd4e0684c5fbacd7457ef7264ca | O=C1c2ccccc2C(=O)N1CCCCBr.Oc1ccncc1>>O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 | OC1=CC=NC=C1.BrCCCCN1C(C=2C(C1=O)=CC=CC2)=O.C1CCC2=NCCCN2CC1>>C1(C=2C(C(N1CCCCOC1=CC=NC=C1)=O)=CC=CC2)=O | Br[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[OH:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | O=C1c2ccccc2C(=O)N1CCCCBr.Oc1ccncc1 | O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 17.8 | [{"value": 17.2, "product": "C1(C=2C(C(N1CCCCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.8, "product": "C1(C=2C(C(N1CCCCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 15.52 g (55 mmol) of N-(4bromobutyl)phthalimide in 80 ml of DMF was added 8.23 ml (5 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene. The mixture was stirred at room temperature for 7 hours. After the solvent was distilled off, the mixture was poured into water and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HBr | CN(C)C=O | null | 7 | O=C1c2ccccc2C(=O)N1CCCCBr.Oc1ccncc1>CN(C)C=O>O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9078b706d8484760a405cf9de643eb4b | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>>NCCCOc1ccncc1 | O.NN.C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O.C(C)(=O)OCC>>NCCCOC1=CC=NC=C1 | O=C1c2ccccc2C(=O)[N:1]1[CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | NCCCOc1ccncc1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccncc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 99.5 | [{"value": 99.5, "product": "NCCCOC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "NCCCOC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Hydrazine monohydrate [2.99 ml (61.6 mmol)] was added to a suspension of 5.80 g (20.5 mol) of 4-(3-phthalimidopropyloxy)pyridine in 50 ml of ethanol, and the mixture was stirred at room temperature for 3 hours. 100 ml of ethyl acetate was added and insoluble materials were filtered off. The volatile component in the fi... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccncc1 | HO- | C(C)O | null | 3 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>C(C)O>NCCCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cc46162356544f669d9d762c2d76ff4b | CC(C)(C)C(=O)Cl.NCCCOc1ccncc1>>CC(C)(C)C(=O)NCCCOc1ccncc1 | NCCCOC1=CC=NC=C1.C(C)N(CC)CC.C(C(C)(C)C)(=O)Cl>>C(C(C)(C)C)(=O)NCCCOC1=CC=NC=C1 | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1 | CC(C)(C)C(=O)Cl.NCCCOc1ccncc1 | CC(C)(C)C(=O)NCCCOc1ccncc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6] | 77.3 | [{"value": 77.3, "product": "C(C(C)(C)C)(=O)NCCCOC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "C(C(C)(C)C)(=O)NCCCOC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 700 mg (4.60 mmol) of 4-(3-aminopropyloxy)pyridine and 0.77 ml (5.52 mmol) of triethylamine in 30 ml of methylene chloride, 0.57 ml (4.63 mmol) of pivaloyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed succ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CC(C)(C)C(=O)Cl.NCCCOc1ccncc1>C(Cl)Cl>CC(C)(C)C(=O)NCCCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-21c6230f734548bda488fe39bf56a85a | NCCCOc1ccncc1.O=C(Cl)c1cccnc1>>O=C(NCCCOc1ccncc1)c1cccnc1 | NCCCOC1=CC=NC=C1.C(C)N(CC)CC.Cl.C(C1=CN=CC=C1)(=O)Cl>>C(C1=CN=CC=C1)(=O)NCCCOC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1 | NCCCOc1ccncc1.O=C(Cl)c1cccnc1 | O=C(NCCCOc1ccncc1)c1cccnc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCOc1ccncc1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 88.7 | [{"value": 85.8, "product": "C(C1=CN=CC=C1)(=O)NCCCOC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.7, "product": "C(C1=CN=CC=C1)(=O)NCCCOC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 700 mg (4.60 mmol) of 4-(3-aminopropyloxy)pyridine and 1.54 ml (11.0 mmol) of triethylamine in 30 ml of methylene chloride, 830 mg (4.66 mmol) of nicotinoyl chloride hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1 | HCl | C(Cl)Cl | null | null | NCCCOc1ccncc1.O=C(Cl)c1cccnc1>C(Cl)Cl>O=C(NCCCOc1ccncc1)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6aaafa271c764cd7bffa5143f19ab4b3 | NCCCOc1ccncc1.O=C(Cl)c1cccs1>>O=C(NCCCOc1ccncc1)c1cccs1 | NCCCOC1=CC=NC=C1.C(C)N(CC)CC.C1(=CC=CS1)C(=O)Cl>>C1(=CC=CS1)C(=O)NCCCOC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][s:18]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][s:18]1 | NCCCOc1ccncc1.O=C(Cl)c1cccs1 | O=C(NCCCOc1ccncc1)c1cccs1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCOc1ccncc1)c1cccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 70.4 | [{"value": 70.0, "product": "C1(=CC=CS1)C(=O)NCCCOC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "C1(=CC=CS1)C(=O)NCCCOC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 700 mg (4.60 mmol) of 4-(3-aminopropyloxy)pyridine and 0.77 ml (5.52 mmol) of triethylamine in 30 ml of methylene chloride, 0.50 ml (4.68 mmol) of thenoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed succe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccsc1 | HCl | C(Cl)Cl | null | null | NCCCOc1ccncc1.O=C(Cl)c1cccs1>C(Cl)Cl>O=C(NCCCOc1ccncc1)c1cccs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-531cdb8862114a2b971e4b24c41a9947 | O=C(Cl)c1ccccc1.c1csc(CNCCCSc2ccncc2)c1>>O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1cccs1 | S1C(=CC=C1)CNCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>S1C(=CC=C1)CN(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[NH:9]([CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1)[CH2:20][c:21]1[cH:22][cH:23][cH:24][s:25]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]([CH2:10][CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1)[CH2:20][c:21... | O=C(Cl)c1ccccc1.c1csc(CNCCCSc2ccncc2)c1 | O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1cccs1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1cccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#16;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#16;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 35.9 | [{"value": 35.9, "product": "S1C(=CC=C1)CN(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.9, "product": "S1C(=CC=C1)CN(C(C1=CC=CC=C1)=O)CCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2.5 g (9.45 mmol) of 4-[3-(N-(2-thienylmethyl)amino)propylthio]pyridine and 1.32 ml (9.45 mmol) of triethylamine in 50 ml of methylene chloride, 1.1 ml (9.45 mmol) of benzoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.c1ccsc1 | HCl | C(Cl)Cl | null | null | O=C(Cl)c1ccccc1.c1csc(CNCCCSc2ccncc2)c1>C(Cl)Cl>O=C(c1ccccc1)N(CCCSc1ccncc1)Cc1cccs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e49129c86d4242ec88a7e0cdf427a563 | CCCCCCCCCCCCN.OCCCSc1ccncc1>>CCCCCCCCCCCCNCCCSc1ccncc1 | OCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(CCCCCCCCCCC)N.CS(=O)(=O)Cl>>C(CCCCCCCCCCC)NCCCSC1=CC=NC=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][NH2:13].O[CH2:14][CH2:15][CH2:16][S:17][c:18]1[cH:19][cH:20][n:21][cH:22][cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][S:17][c:18]1[cH:19][cH:20][n:2... | CCCCCCCCCCCCN.OCCCSc1ccncc1 | CCCCCCCCCCCCNCCCSc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1ccncc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 29.5 | [{"value": 29.5, "product": "C(CCCCCCCCCCC)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.5, "product": "C(CCCCCCCCCCC)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In 120 ml of methylene chloride was dissolved 5.60 g (33.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.53 ml (39.7 mmol) of triethylamine. 3.07 ml (39.7 mmol) of methanesulfonyl chloride was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | 0.5 | CCCCCCCCCCCCN.OCCCSc1ccncc1>C(Cl)Cl>CCCCCCCCCCCCNCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c02e45927e744116961d5f80a7284f40 | O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CCl.Sc1ccncc1>>O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CSc1ccncc1 | ClCN1C(C=2C(C1=O)=CC(=CC2)[N+](=O)[O-])=O.SC1=CC=NC=C1.C(C)N(CC)CC>>[N+](=O)([O-])C=1C=C2C(C(=O)N(C2=O)CSC2=CC=NC=C2)=CC1 | Cl[CH2:15][N:14]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]2[C:12]1=[O:13].[SH:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]2[C:12](=[O:13])[N:14]1[CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CCl.Sc1ccncc1 | O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CSc1ccncc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 670a330769b87d9fd3df1128eae04bdefd1a0d70c3e632885aa0e6a5b15fccc1 | fcd4bd1a4380f5eecf1a2477e13ea8343f264aec0388929401fe7448dc3025d8 | O=C1c2ccccc2C(=O)N1CSc1ccncc1 | Cl-[CH2;D2;+0:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]-[C:7]-1=[O;D1;H0:8].[SH;D1;+0:9]-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[O;D1;H0:4]=[C:3]1-[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[#7:2]-1-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1 | 63.1 | [{"value": 63.1, "product": "[N+](=O)([O-])C=1C=C2C(C(=O)N(C2=O)CSC2=CC=NC=C2)=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "[N+](=O)([O-])C=1C=C2C(C(=O)N(C2=O)CSC2=CC=NC=C2)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | N-Chloromethyl-4-nitrophthalimide [2.89 g (12 mmol)] was added under ice-cooling with stirring to a suspension of 1.11 g (10 mmol) of 4-mercaptopyridine and 1.4 ml (12 mmol) of triethylamine in 50 ml of ethanol. The mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Substituted dicarboximide.Aromatic thiol | Substituted dicarboximide.Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HCl | C(C)O | null | 16 | O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CCl.Sc1ccncc1>C(C)O>O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d07aa11821184f368af462667f02ae8c | O=C1c2ccccc2C(=O)N1CSc1ccncc1>>O=C1c2ccccc2C(O)N1CSc1ccncc1 | C1(C=2C(C(N1CSC1=CC=NC=C1)=O)=CC=CC2)=O.[BH4-].[Na+].C(C)(=O)O>>OC1N(C(C2=CC=CC=C12)=O)CSC1=CC=NC=C1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | O=C1c2ccccc2C(=O)N1CSc1ccncc1 | O=C1c2ccccc2C(O)N1CSc1ccncc1 | null | null | CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1CSc1ccncc1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 58.3 | [{"value": 58.3, "product": "OC1N(C(C2=CC=CC=C12)=O)CSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "OC1N(C(C2=CC=CC=C12)=O)CSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 4.01 g (14.8 mmol) of 4-(phthalimidomethylthio)pyridine in 25 ml of methanol, a solution of 1.08 g (29.7 mmol) of sodium borohydride in 20 ml of methanol was added. The mixture was stirred at room temperature for 4 hours. Glacial acetic acid (0.5 ml) was added to quench the reaction, and then the solve... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | CO | null | 4 | O=C1c2ccccc2C(=O)N1CSc1ccncc1>CO>O=C1c2ccccc2C(O)N1CSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-73cf2bb5afde4483b79e29dae5dd822c | O=C1c2ccccc2C(=O)N1CCBr.Oc1ccncc1>>O=C1c2ccccc2C(=O)N1CCOc1ccncc1 | OC1=CC=NC=C1.BrCCN1C(C=2C(C1=O)=CC=CC2)=O.C1CCC2=NCCCN2CC1>>C1(C=2C(C(N1CCOC1=CC=NC=C1)=O)=CC=CC2)=O | Br[CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[OH:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1 | O=C1c2ccccc2C(=O)N1CCBr.Oc1ccncc1 | O=C1c2ccccc2C(=O)N1CCOc1ccncc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1c2ccccc2C(=O)N1CCOc1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[OH;D1;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[O;D1;H0:7]=[C:6]-[#7:3](-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[C:4]=[O;D1;H0:5] | 3.1 | [{"value": 3.1, "product": "C1(C=2C(C(N1CCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.1, "product": "C1(C=2C(C(N1CCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 32 | HOUR | To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 13.97 g (55 mmol) of N-(2-bromoethyl)phthalimide in 80 ml of DMF, 8.23 ml (55 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added. The mixture was stirred at room temperature for 32 hours. After the solvent was distilled off, the mixture was poured into water... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HBr | CN(C)C=O | null | 32 | O=C1c2ccccc2C(=O)N1CCBr.Oc1ccncc1>CN(C)C=O>O=C1c2ccccc2C(=O)N1CCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-65c49a041cb1404cbaeaf61fdae85da3 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>>O=C1c2ccccc2C(O)N1CCCOc1ccncc1 | [BH4-].[Na+].C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O>>OC1N(C(C2=CC=CC=C12)=O)CCCOC1=CC=NC=C1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | O=C1c2ccccc2C(O)N1CCCOc1ccncc1 | null | null | C(C)O | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1CCCOc1ccncc1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 54.2 | [{"value": 54.2, "product": "OC1N(C(C2=CC=CC=C12)=O)CCCOC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.2, "product": "OC1N(C(C2=CC=CC=C12)=O)CCCOC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Sodium borohydride [1.89 g (50 mmol)] was added to a solution of 2.82 g (10.0 mmol) of 4-(3-phthalimidopropyloxy)pyridine in 150 ml of ethanol. The mixture was stirred at room temperature for 15 minutes. After the solvent was distilled off, brine was added to the residue. The mixture was extracted with chloroform and d... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | C(C)O | null | 0.25 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>C(C)O>O=C1c2ccccc2C(O)N1CCCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4dbf302df4464d14a210fcb5a6554452 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>>O=C(NCCCOc1ccncc1)c1ccccc1CO | [BH4-].[Na+].C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O>>OCC1=C(C(=O)NCCCOC2=CC=NC=C2)C=CC=C1 | [O:1]=[C:2]1[N:3]([CH2:4][CH2:5][CH2:6][O:7][c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[C:20](=[O:21])[c:19]2[c:14]1[cH:15][cH:16][cH:17][cH:18]2>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[CH2:20][OH:21] | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | O=C(NCCCOc1ccncc1)c1ccccc1CO | null | null | C(C)O | Reduction | OtherReaction | d08271d0eab427d20e9711b6b92c8b05348d13735b33b77d21de7bf6727ba260 | a2b47173662031a6246dc71f980ac535bbdf2e2fb828bdc621ee9b3169b07859 | O=C(NCCCOc1ccncc1)c1ccccc1 | [C:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[CH2;D2;+0:9]-[OH;D1;+0:10]):[c:8] | 52 | [{"value": 52.0, "product": "OCC1=C(C(=O)NCCCOC2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.0, "product": "OCC1=C(C(=O)NCCCOC2=CC=NC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Sodium borohydride [3.78 g (100 mmol)] was added to a solution of 2.82 g (10.0 mmol) of 4-(3-phthalimidopropyloxy)pyridine in 150 ml of ethanol. The mixture was stirred at room temperature for 3 hours. After the solvent was distiled off, brine was added to the residue. The mixture was extracted with chloroform and drie... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary amide.Primary alcohol | c1ccc2c(c1)C[NH]C2 | null | c1ccncc1.c1ccccc1 | null | C(C)O | null | 3 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>C(C)O>O=C(NCCCOc1ccncc1)c1ccccc1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b2748f3faf0e4cadb94edae14f08f39f | O=C1c2ccccc2C(=O)N1CCSc1ccncc1>>O=C(NCCSc1ccncc1)c1ccccc1CO | C(C)O.C(C)(=O)OCC.C1(C=2C(C(N1CCSC1=CC=NC=C1)=O)=CC=CC2)=O.[BH4-].[Na+]>>OCC1=C(C(=O)NCCSC2=CC=NC=C2)C=CC=C1 | [O:1]=[C:2]1[N:3]([CH2:4][CH2:5][S:6][c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[C:19](=[O:20])[c:18]2[c:13]1[cH:14][cH:15][cH:16][cH:17]2>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH2:19][OH:20] | O=C1c2ccccc2C(=O)N1CCSc1ccncc1 | O=C(NCCSc1ccncc1)c1ccccc1CO | null | null | C(C)O | Reduction | OtherReaction | d08271d0eab427d20e9711b6b92c8b05348d13735b33b77d21de7bf6727ba260 | a2b47173662031a6246dc71f980ac535bbdf2e2fb828bdc621ee9b3169b07859 | O=C(NCCSc1ccncc1)c1ccccc1 | [C:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[CH2;D2;+0:9]-[OH;D1;+0:10]):[c:8] | 77.8 | [{"value": 77.8, "product": "OCC1=C(C(=O)NCCSC2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "OCC1=C(C(=O)NCCSC2=CC=NC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2.84 g (10.0 mmol) of 4-(2-phthalimidoethylthio)pyridine in 150 ml of ethanol, 3.78 g (100 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chlo... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary amide.Primary alcohol | c1ccc2c(c1)C[NH]C2 | null | c1ccncc1.c1ccccc1 | null | C(C)O | null | 3 | O=C1c2ccccc2C(=O)N1CCSc1ccncc1>C(C)O>O=C(NCCSc1ccncc1)c1ccccc1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-971581ad4e8b4fdcb8263bf8c74245a7 | O=C1c2ccccc2C(=O)N1CCSc1ccncc1>>O=C1c2ccccc2C(O)N1CCSc1ccncc1 | C1(C=2C(C(N1CCSC1=CC=NC=C1)=O)=CC=CC2)=O.[BH4-].[Na+]>>OC1N(C(C2=CC=CC=C12)=O)CCSC1=CC=NC=C1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1 | O=C1c2ccccc2C(=O)N1CCSc1ccncc1 | O=C1c2ccccc2C(O)N1CCSc1ccncc1 | null | null | C(C)O | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1CCSc1ccncc1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 63.4 | [{"value": 63.4, "product": "OC1N(C(C2=CC=CC=C12)=O)CCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "OC1N(C(C2=CC=CC=C12)=O)CCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 5.69 g (20.0 mmol) of 4-(2-phthalimidoethylthio)pyridine in 150 ml of ethanol, 2.27 g (60 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 15 minutes. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with ch... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | C(C)O | null | 0.25 | O=C1c2ccccc2C(=O)N1CCSc1ccncc1>C(C)O>O=C1c2ccccc2C(O)N1CCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5cf6e169638414f92985c34a5a2a735 | O=C(NCCSc1ccncc1)c1ccccc1CO>>O=C1c2ccccc2CN1CCSc1ccncc1 | OCC1=C(C(=O)NCCSC2=CC=NC=C2)C=CC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>C1(N(CC2=CC=CC=C12)CCSC1=CC=NC=C1)=O | O[CH2:9][c:8]1[c:3]([C:2](=[O:1])[NH:10][CH2:11][CH2:12][S:13][c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[cH:4][cH:5][cH:6][cH:7]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][N:10]1[CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | O=C(NCCSc1ccncc1)c1ccccc1CO | O=C1c2ccccc2CN1CCSc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1b80d36cd86c1f0c2ab7ea6bfe3b27d1140e09d54a6c4337a116e3cf30d8d950 | 53e9ea6bdc0d22524e13e79960e55c0106a6cc8b9aed21c29c8c6a7e9792ce5b | O=C1c2ccccc2CN1CCSc1ccncc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:9]-[C:8]-[N;H0;D3;+0:7]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]-1=[O;D1;H0:6] | 57.6 | [{"value": 57.6, "product": "C1(N(CC2=CC=CC=C12)CCSC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "C1(N(CC2=CC=CC=C12)CCSC1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.153 g (4.0 mmol) of 4-[2-(2-hydroxymethylbenzoyl)aminoethylthio]pyridine and 1.68 ml (12.1 mmol) of triethylamine in 50 ml of methylene chloride, 0.62 ml (8.0 mmol) of methanesulfonyl chloride was added with stirring at room temperature, and the mixture was stirred at room temperature for 30 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary alcohol | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HO- | C(Cl)Cl | null | null | O=C(NCCSc1ccncc1)c1ccccc1CO>C(Cl)Cl>O=C1c2ccccc2CN1CCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b088d415086140f09c65a666de315251 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1>>O=C(NCCCCSc1ccncc1)c1ccccc1CO | C1(C=2C(C(N1CCCCSC1=CC=NC=C1)=O)=CC=CC2)=O.[BH4-].[Na+]>>OCC1=C(C(=O)NCCCCSC2=CC=NC=C2)C=CC=C1 | [O:1]=[C:2]1[N:3]([CH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[C:21](=[O:22])[c:20]2[c:15]1[cH:16][cH:17][cH:18][cH:19]2>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[CH2:21][OH:22] | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1 | O=C(NCCCCSc1ccncc1)c1ccccc1CO | null | null | C(C)O | Reduction | OtherReaction | d08271d0eab427d20e9711b6b92c8b05348d13735b33b77d21de7bf6727ba260 | a2b47173662031a6246dc71f980ac535bbdf2e2fb828bdc621ee9b3169b07859 | O=C(NCCCCSc1ccncc1)c1ccccc1 | [C:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[CH2;D2;+0:9]-[OH;D1;+0:10]):[c:8] | 73.2 | [{"value": 73.1, "product": "OCC1=C(C(=O)NCCCCSC2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "OCC1=C(C(=O)NCCCCSC2=CC=NC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 6.25 g of (20.0 mmol) of 4-(4-phthalimidobutylthio)pyridine in 300 ml of ethanol, 7.57 g (200 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 14 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary amide.Primary alcohol | c1ccc2c(c1)C[NH]C2 | null | c1ccncc1.c1ccccc1 | null | C(C)O | null | 14 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1>C(C)O>O=C(NCCCCSc1ccncc1)c1ccccc1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-923c49f34b564c8dbe84a85dc91bb505 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1>>O=C1c2ccccc2C(O)N1CCCCSc1ccncc1 | C1(C=2C(C(N1CCCCSC1=CC=NC=C1)=O)=CC=CC2)=O.[BH4-].[Na+]>>OC1N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1 | O=C1c2ccccc2C(O)N1CCCCSc1ccncc1 | null | null | C(C)O | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1CCCCSc1ccncc1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 27.5 | [{"value": 27.5, "product": "OC1N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "OC1N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of 6.25 g (20.0 mol) of 4-(4-phthalimidobutylthio)pyridine in 300 ml of ethanol, 1.51 g (40 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 2.5 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chlo... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | C(C)O | null | 2.5 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1>C(C)O>O=C1c2ccccc2C(O)N1CCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f7c946d278a44fe28f799ef9783e5d4b | O=C1c2ccccc2C(=O)N1CCCSc1ccncc1>>O=C(NCCCSc1ccncc1)c1ccccc1CO | C1(C=2C(C(N1CCCSC1=CC=NC=C1)=O)=CC=CC2)=O.[BH4-].[Na+]>>OCC1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1 | [O:1]=[C:2]1[N:3]([CH2:4][CH2:5][CH2:6][S:7][c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[C:20](=[O:21])[c:19]2[c:14]1[cH:15][cH:16][cH:17][cH:18]2>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[CH2:20][OH:21] | O=C1c2ccccc2C(=O)N1CCCSc1ccncc1 | O=C(NCCCSc1ccncc1)c1ccccc1CO | null | null | C(C)O | Reduction | OtherReaction | d08271d0eab427d20e9711b6b92c8b05348d13735b33b77d21de7bf6727ba260 | a2b47173662031a6246dc71f980ac535bbdf2e2fb828bdc621ee9b3169b07859 | O=C(NCCCSc1ccncc1)c1ccccc1 | [C:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[CH2;D2;+0:9]-[OH;D1;+0:10]):[c:8] | 78.2 | [{"value": 78.2, "product": "OCC1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "OCC1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 5.97 g (20.0 mmol) of 4-(3-phthalimidopropylthio)pyridine in 300 ml of ethanol, 7.57 g (200 mmol) of sodium borohydride was added, and stirred at room temperature for 24 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary amide.Primary alcohol | c1ccc2c(c1)C[NH]C2 | null | c1ccncc1.c1ccccc1 | null | C(C)O | null | 24 | O=C1c2ccccc2C(=O)N1CCCSc1ccncc1>C(C)O>O=C(NCCCSc1ccncc1)c1ccccc1CO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-84539951ddac46c78e3e61887eb06d08 | O=C(NCCCCSc1ccncc1)c1ccccc1CO>>O=C1c2ccccc2CN1CCCCSc1ccncc1 | OCC1=C(C(=O)NCCCCSC2=CC=NC=C2)C=CC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>C1(N(CC2=CC=CC=C12)CCCCSC1=CC=NC=C1)=O | O[CH2:9][c:8]1[c:3]([C:2](=[O:1])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[cH:4][cH:5][cH:6][cH:7]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | O=C(NCCCCSc1ccncc1)c1ccccc1CO | O=C1c2ccccc2CN1CCCCSc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1b80d36cd86c1f0c2ab7ea6bfe3b27d1140e09d54a6c4337a116e3cf30d8d950 | 53e9ea6bdc0d22524e13e79960e55c0106a6cc8b9aed21c29c8c6a7e9792ce5b | O=C1c2ccccc2CN1CCCCSc1ccncc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:9]-[C:8]-[N;H0;D3;+0:7]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]-1=[O;D1;H0:6] | 72.1 | [{"value": 72.1, "product": "C1(N(CC2=CC=CC=C12)CCCCSC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "C1(N(CC2=CC=CC=C12)CCCCSC1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.58 g (5.0 mmol) of 4-[4-(2-hydroxymethylbenzoyl)aminobutylthio]pyridine and 2.09 ml (15.0 mmol) of triethylamine in 50 ml of methylene chloride, 0.77 ml (10.0 mmol) of methanesulfonyl chloride was added with stirring at room temperature, and the mixture was stirred at room temperature for 30 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary alcohol | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HO- | C(Cl)Cl | null | null | O=C(NCCCCSc1ccncc1)c1ccccc1CO>C(Cl)Cl>O=C1c2ccccc2CN1CCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f61c39e9b64e46f3aa67a30fba7b886d | O=C1c2ccccc2C(=O)N1CCCSc1ccncc1>>O=C1c2ccccc2C(O)N1CCCSc1ccncc1 | C(C)O.C(C)(=O)OCC.C1(C=2C(C(N1CCCSC1=CC=NC=C1)=O)=CC=CC2)=O.[BH4-].[Na+]>>OC1N(C(C2=CC=CC=C12)=O)CCCSC1=CC=NC=C1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | O=C1c2ccccc2C(=O)N1CCCSc1ccncc1 | O=C1c2ccccc2C(O)N1CCCSc1ccncc1 | null | null | C(C)O | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1CCCSc1ccncc1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 54.4 | [{"value": 54.4, "product": "OC1N(C(C2=CC=CC=C12)=O)CCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "OC1N(C(C2=CC=CC=C12)=O)CCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 5.97 g (20.0 mmol) of 4-(3-phthalimidopropylthio)pyridine in 300 ml of ethanol, 1.51 g (40 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chlo... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | C(C)O | null | 5 | O=C1c2ccccc2C(=O)N1CCCSc1ccncc1>C(C)O>O=C1c2ccccc2C(O)N1CCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0be3a0bcf2234748992476eebd2f65be | O=C(NCCCSc1ccncc1)c1ccccc1CO>>O=C1c2ccccc2CN1CCCSc1ccncc1 | OCC1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>C1(N(CC2=CC=CC=C12)CCCSC1=CC=NC=C1)=O | O[CH2:9][c:8]1[c:3]([C:2](=[O:1])[NH:10][CH2:11][CH2:12][CH2:13][S:14][c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[cH:4][cH:5][cH:6][cH:7]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1 | O=C(NCCCSc1ccncc1)c1ccccc1CO | O=C1c2ccccc2CN1CCCSc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1b80d36cd86c1f0c2ab7ea6bfe3b27d1140e09d54a6c4337a116e3cf30d8d950 | 53e9ea6bdc0d22524e13e79960e55c0106a6cc8b9aed21c29c8c6a7e9792ce5b | O=C1c2ccccc2CN1CCCSc1ccncc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:9]-[C:8]-[N;H0;D3;+0:7]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]-1=[O;D1;H0:6] | 78.9 | [{"value": 78.9, "product": "C1(N(CC2=CC=CC=C12)CCCSC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "C1(N(CC2=CC=CC=C12)CCCSC1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.51 g (5.0 mmol) of 4-[3-(2-hydroxymethylbenzoyl)aminopropylthio]pyridine and 2.09 ml (15.0 mmol) of triethylamine in 50 ml of methylene chloride, 0.77 ml (10.0 mmol) of methanesulfonyl chloride was added with stirring at room temperature, and the mixture was stirred at room temperature for 30 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary alcohol | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | HO- | C(Cl)Cl | null | null | O=C(NCCCSc1ccncc1)c1ccccc1CO>C(Cl)Cl>O=C1c2ccccc2CN1CCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4a5162e35a304121b841b3e3f39d8e9f | CN.O=C1c2ccccc2C(=O)N1CSc1ccncc1>>CNC(=O)c1ccccc1C(=O)NCSc1ccncc1 | CN.CO.C1(C=2C(C(N1CSC1=CC=NC=C1)=O)=CC=CC2)=O.CN.CO>>CNC(=O)C1=C(C(=O)NCSC2=CC=NC=C2)C=CC=C1 | [CH3:1][NH2:2].[C:3]1(=[O:4])[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11](=[O:12])[N:13]1[CH2:14][S:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[NH:13][CH2:14][S:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | CN.O=C1c2ccccc2C(=O)N1CSc1ccncc1 | CNC(=O)c1ccccc1C(=O)NCSc1ccncc1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | 66718301acef3d8bc25ae8613c1648aa67ee84cf1a582b43da3ed3cccd3e499c | c5dbbff33268430c8bfa22331d710773ca50cd979a5fb6dcb4356e0495eb059b | O=C(NCSc1ccncc1)c1ccccc1 | [#16:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;D1;H0:10].[C;D1;H3:11]-[NH2;D1;+0:12]>>[#16:1]-[C:2]-[NH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:12]-[C;D1;H3:11]):[c:8] | 35.1 | [{"value": 35.1, "product": "CNC(=O)C1=C(C(=O)NCSC2=CC=NC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 6.76 g (25.0 mmol) of 4-phthalimidomethylthiopyridine in 100 ml of chloroform, 5 ml of 40% methylamine-methanol solution was added, and the mixture was stirred at room temperature for 3 hours. Additional 5 ml of 40% methylamine-methanol solution was added, and the mixture was stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide.Primary amine | Secondary amide.Secondary amide | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1ccncc1 | null | C(Cl)(Cl)Cl | null | 3 | CN.O=C1c2ccccc2C(=O)N1CSc1ccncc1>C(Cl)(Cl)Cl>CNC(=O)c1ccccc1C(=O)NCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c962e1c87c844b4594420eb59c04a717 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>>O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O.Cl.CO>>Cl.C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O | [O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 | null | 64.8 | [{"value": 64.8, "product": "Cl.C1(C=2C(C(N1CCCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.41 g (5.0 mmol) of 4-(3-phthalimidopropyloxy)pyridine in 20 ml of methanol, 10 ml of hydrogen chloride-methanol was added. The solvent was distilled off and acetone was added to the residue. The resulting crystals were collected by filtration and washed with acetone to give 1.03 g of the desired comp... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | CO | null | null | O=C1c2ccccc2C(=O)N1CCCOc1ccncc1>CO>O=C1c2ccccc2C(=O)N1CCCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7872d2ae7d2e4c56a28ce90cf19a337d | O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1>>O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 | C1(C=2C(C(N1CCCCOC1=CC=NC=C1)=O)=CC=CC2)=O.Cl.CO>>Cl.C1(C=2C(C(N1CCCCOC1=CC=NC=C1)=O)=CC=CC2)=O | [O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][n:21][cH:22][cH:23]1>>[O:2]=[C:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][n:21][cH:22][cH:23]1 | O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 | O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 | null | 86.3 | [{"value": 86.3, "product": "Cl.C1(C=2C(C(N1CCCCOC1=CC=NC=C1)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 1.48 g (5.0 mmol) of 4-(4-phthalimidobutyloxy)pyridine in 20 ml of methanol, 15 ml of hydrogen chloride-methanol was added and dissolve. The solvent was distilled off and the residue was crystallized from acetone-ether. The resulting crystals were collected by filtration and washed with ether to give... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1 | null | CO | null | null | O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1>CO>O=C1c2ccccc2C(=O)N1CCCCOc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d55965f78437450f9aef72b94ae9f168 | NCCCSc1ccncc1.O=C(O)c1cnccn1>>O=C(NCCCSc1ccncc1)c1cnccn1 | Cl.Cl.NCCCSC1=CC=NC=C1.N1=C(C=NC=C1)C(=O)O.ON1C(CCC1=O)=O.Cl.C(C)N=C=NCCCN(C)C>>N1=C(C=NC=C1)C(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.O[C:2](=[O:1])[c:14]1[cH:15][n:16][cH:17][cH:18][n:19]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][n:16][cH:17][cH:18][n:19]1 | NCCCSc1ccncc1.O=C(O)c1cnccn1 | O=C(NCCCSc1ccncc1)c1cnccn1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCSc1ccncc1)c1cnccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1 | 34 | [{"value": 34.0, "product": "N1=C(C=NC=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.0, "product": "N1=C(C=NC=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (8.06 mmol) of 2-pyrazinecarboxylic acid and 1.21 g (10.5 mmol) of N-hydroxysuccinimide in 70 ml of methylene-chloride, 1.85 g (9.67 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was added with stirring under ice-cooling, and the mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1cnccn1 | HO- | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(O)c1cnccn1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1cnccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eada9dfe6c2247098ac3fc6740df3411 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1>>NCCCCSc1ccncc1 | C(C)(=O)OCC.C1(C=2C(C(N1CCCCSC1=CC=NC=C1)=O)=CC=CC2)=O.O.NN>>NCCCCSC1=CC=NC=C1 | O=C1c2ccccc2C(=O)[N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1 | NCCCCSc1ccncc1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccncc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH2;D1;+0:1] | 100.1 | [{"value": 100.1, "product": "NCCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a suspension of 12.50 g (40 mmol) of 4-(4-phthalimidobutylthio)pyridine in 200 ml of ethanol, 5.82 ml (120 mmol) of hydrazine monohydrate was added, and the mixture was stirred at room temperature for 4 hours. Then, 200 ml of ethyl acetate was-added, and the insoluble material was filtered off. The volatile componen... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccncc1 | HO- | C(C)O | null | 4 | O=C1c2ccccc2C(=O)N1CCCCSc1ccncc1>C(C)O>NCCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b219b6ddb6814fc39f98caa37e23e5ac | NCCCCSc1ccncc1.O=C(Cl)c1ccccc1>>O=C(NCCCCSc1ccncc1)c1ccccc1 | NCCCCSC1=CC=NC=C1.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)NCCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1.Cl[C:2](=[O:1])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | NCCCCSc1ccncc1.O=C(Cl)c1ccccc1 | O=C(NCCCCSc1ccncc1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCCSc1ccncc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 34.4 | [{"value": 34.4, "product": "C(C1=CC=CC=C1)(=O)NCCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.3, "product": "C(C1=CC=CC=C1)(=O)NCCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.00 g (5.49 mmol) of 4-(4-aminobutylthio)pyridine and 0.92 ml (6.60 mmol) of triethylamine in 30 ml of methylene chloride, 0.67 ml (5.77 mmol) of benzoyl chloride was added with stirring under ice-cooling and the mixture was stirred at room temperature for 13 hours. The mixture was washed with saturat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | NCCCCSc1ccncc1.O=C(Cl)c1ccccc1>C(Cl)Cl>O=C(NCCCCSc1ccncc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eac925e9b2f940fdb1f04bc16132b520 | O=C(NCO)c1cccnc1.Sc1ccncc1>>O=C(NCSc1ccncc1)c1cccnc1 | SC1=CC=NC=C1.OCNC(C1=CN=CC=C1)=O>>N1=CC(=CC=C1)C(=O)NCSC1=CC=NC=C1 | O[CH2:4][NH:3][C:2](=[O:1])[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1.[SH:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[O:1]=[C:2]([NH:3][CH2:4][S:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1 | O=C(NCO)c1cccnc1.Sc1ccncc1 | O=C(NCSc1ccncc1)c1cccnc1 | null | null | FC(C(=O)O)(F)F | Heteroatom Alkylation and Arylation | OtherReaction | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | O=C(NCSc1ccncc1)c1cccnc1 | O-[CH2;D2;+0:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7].[SH;D1;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[#7;a:7]:[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#7:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 15.9 | [{"value": 15.9, "product": "N1=CC(=CC=C1)C(=O)NCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.9, "product": "N1=CC(=CC=C1)C(=O)NCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 1.11 g (10 mmol) of 4-mercaptopyridine and 1.52 g (10 mmol) of N-(hydroxymethyl)nicotinamide, 30 ml of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off and 30 ml of ethanol was added to the residue. The solvent was distilled off an... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccncc1 | HO- | FC(C(=O)O)(F)F | null | 1 | O=C(NCO)c1cccnc1.Sc1ccncc1>FC(C(=O)O)(F)F>O=C(NCSc1ccncc1)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-223b53ba401c4783b307cafc7579f4f4 | CC1(C)NC(=O)NC1=O.ClCCCCSc1ccncc1>>CC1(C)NC(=O)N(CCCCSc2ccncc2)C1=O | C(C)(=O)OCC.CC1(C(NC(N1)=O)=O)C.ClCCCCSC1=CC=NC=C1.C1CCC2=NCCCN2CC1>>CC1(C(N(C(N1)=O)CCCCSC1=CC=NC=C1)=O)C | [CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[O:6])[NH:7][C:19]1=[O:20].Cl[CH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[O:6])[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[C:19]1=[O:20] | CC1(C)NC(=O)NC1=O.ClCCCCSc1ccncc1 | CC1(C)NC(=O)N(CCCCSc2ccncc2)C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 4af6a84b2b0a49ef91adc20903acb4fb123b5aba0377309152c828b38a40c4ee | 71185a09698a72d85470086badab5839fe3f255541f1fa400a1649b43c12f685 | O=C1CNC(=O)N1CCCCSc1ccncc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[C:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:5](=[O;D1;H0:4])-[C:6]-[#7:7]-[C:8]-1=[O;D1;H0:9] | 56.8 | [{"value": 56.8, "product": "CC1(C(N(C(N1)=O)CCCCSC1=CC=NC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "CC1(C(N(C(N1)=O)CCCCSC1=CC=NC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 43 | HOUR | To a solution of 2.56 g (20 mmol) of 5,5-dimethylhydantoin and 4.03 g (20 mmol) of 4-(4-chlorobutylthio)pyridine in 20 ml of N,N-dimethylformamide, 3.00 ml (20 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at room temperature for 43 hours, followed by further stirring at 70° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea.Substituted dicarboximide | C1CNCN1 | C1C[NH]CN1 | C1C[NH]CN1.c1ccncc1 | HCl | CN(C=O)C | null | 43 | CC1(C)NC(=O)NC1=O.ClCCCCSc1ccncc1>CN(C=O)C>CC1(C)NC(=O)N(CCCCSc2ccncc2)C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f99fd64ecadc4d6fbfc0db3ce5607ef8 | O=C1CSC(=O)N1.O=Cc1ccccc1>>O=C1NC(=O)C(=Cc2ccccc2)S1 | S1C(NC(C1)=O)=O.C(C1=CC=CC=C1)=O.N1CCCCC1>>C(C1=CC=CC=C1)=C1C(NC(S1)=O)=O | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH2:6][S:14]1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6](=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[S:14]1 | O=C1CSC(=O)N1.O=Cc1ccccc1 | O=C1NC(=O)C(=Cc2ccccc2)S1 | null | null | C(C)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=O)C(=Cc2ccccc2)S1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-1>>[O;D1;H0:5]=[C:6]1-[#16:7]-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#7:11]-1 | 90.4 | [{"value": 90.4, "product": "C(C1=CC=CC=C1)=C1C(NC(S1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.2, "product": "C(C1=CC=CC=C1)=C1C(NC(S1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 20 g (171 mmol) of 2,4-thiazolidinedione and 17.4 ml (171 mmol) of benzaldehyde in 350 ml of ethanol, 1.68 ml (17.1 mmol) of piperidine was added, and the mixture was heated under reflux for 5 hours. After cooling, the precipitated crystals were filtered and washed with cooled ethanol to give 31.67 g o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | C1CSCN1.c1ccccc1 | HO- | C(C)O | null | null | O=C1CSC(=O)N1.O=Cc1ccccc1>C(C)O>O=C1NC(=O)C(=Cc2ccccc2)S1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f955cb05073547f09e8e193f4ca25145 | O=C1CSC(=O)N1.O=Cc1ccc(Cl)cc1>>O=C1NC(=O)C(=Cc2ccc(Cl)cc2)S1 | S1C(NC(C1)=O)=O.ClC1=CC=C(C=O)C=C1.N1CCCCC1>>ClC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1 | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH2:6][S:15]1.O=[CH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6](=[CH:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15]1 | O=C1CSC(=O)N1.O=Cc1ccc(Cl)cc1 | O=C1NC(=O)C(=Cc2ccc(Cl)cc2)S1 | null | null | C(C)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=O)C(=Cc2ccccc2)S1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#16:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-1>>[O;D1;H0:5]=[C:6]1-[#16:7]-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#7:11]-1 | 43.4 | [{"value": 43.4, "product": "ClC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.3, "product": "ClC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 20 g (171 mmol) of 2,4-thiazolidinedione and 17.4 ml (171 mmol) of 4-chlorobenzaldehyde in 350 ml of ethanol, 1.68 ml (17.1 mmol) of piperidine was added, and the mixture was heated under reflux for 5 hours. After cooling, the precipitated crystals were filtered and washed with cooled ethanol to give 1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | C1CSCN1.c1ccccc1 | HO- | C(C)O | null | null | O=C1CSC(=O)N1.O=Cc1ccc(Cl)cc1>C(C)O>O=C1NC(=O)C(=Cc2ccc(Cl)cc2)S1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d824881d53434cb8beb91cc10043c497 | O=C1CSC(=S)N1.O=Cc1ccccc1>>O=C1NC(=S)SC1=Cc1ccccc1 | S1C(=S)NC(=O)C1.C(C1=CC=CC=C1)=O.N1CCCCC1>>C(C1=CC=CC=C1)=C1C(NC(S1)=S)=O | [O:1]=[C:2]1[NH:3][C:4](=[S:5])[S:6][CH2:7]1.O=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]1[NH:3][C:4](=[S:5])[S:6][C:7]1=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | O=C1CSC(=S)N1.O=Cc1ccccc1 | O=C1NC(=S)SC1=Cc1ccccc1 | null | null | C(C)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=S)SC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 66.6 | [{"value": 66.6, "product": "C(C1=CC=CC=C1)=C1C(NC(S1)=S)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "C(C1=CC=CC=C1)=C1C(NC(S1)=S)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10 g (75.1 mmol) of rhodanine and 7.63 ml (75.1 mmol) of benzaldehyde in 150 ml of ethanol, 0.74 ml (7.5 mmol) of piperidine was added, and the mixture was heated under reflux for 5 hours. After cooling, the precipitated crystals were filtered and washed with cooled ethanol to give 11.07 g of the desir... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | C1CSCN1.c1ccccc1 | HO- | C(C)O | null | null | O=C1CSC(=S)N1.O=Cc1ccccc1>C(C)O>O=C1NC(=S)SC1=Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fe71a2c02edc41da90a957171964ea9f | O=C1CSC(=O)N1.O=Cc1cccs1>>O=C1NC(=O)C(=Cc2cccs2)S1 | S1C(NC(C1)=O)=O.S1C(=CC=C1)C=O.N1CCCCC1>>S1C(=CC=C1)C=C1C(NC(S1)=O)=O | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[CH2:6][S:13]1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][s:12]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[C:6](=[CH:7][c:8]2[cH:9][cH:10][cH:11][s:12]2)[S:13]1 | O=C1CSC(=O)N1.O=Cc1cccs1 | O=C1NC(=O)C(=Cc2cccs2)S1 | null | null | C(C)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=O)C(=Cc2cccs2)S1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#16:8]-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1>>[O;D1;H0:6]=[C:7]1-[#16:8]-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5])-[C:10](=[O;D1;H0:11])-[#7:12]-1 | 66.6 | [{"value": 66.6, "product": "S1C(=CC=C1)C=C1C(NC(S1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "S1C(=CC=C1)C=C1C(NC(S1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 20 g (171 mmol) of 2,4-thiazolidinedione and 16.0 ml (171 mmol) of 2-thiophenecarboxaldehyde in 350 ml of ethanol, 1.68 ml (17.1 mmol) of piperidine was added, and the mixture was heated under reflux for 5 hours. After cooling, the precipitated crystals were filtered and washed with cooled ethanol to g... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | C1CSCN1.c1ccsc1 | HO- | C(C)O | null | null | O=C1CSC(=O)N1.O=Cc1cccs1>C(C)O>O=C1NC(=O)C(=Cc2cccs2)S1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e9a40193820a432da78afb9efd42f92a | ClCCCCBr.Sc1ccccn1>>ClCCCCSc1ccccn1 | SC1=NC=CC=C1.C(C)N(CC)CC.BrCCCCCl>>ClCCCCSC1=NC=CC=C1 | Br[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1].[SH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][n:12]1>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][cH:11][n:12]1 | ClCCCCBr.Sc1ccccn1 | ClCCCCSc1ccccn1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | 65.5 | [{"value": 65.5, "product": "ClCCCCSC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.5, "product": "ClCCCCSC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 25.0 g (225 mmol) of 2-mercaptopyridine and 34.5 ml (247 mmol) of triethylamine in 300 ml of ethanol, 28.5 ml (247 mmol) of 1-bromo-4-chlorobutane was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1 | HBr | C(C)O | null | null | ClCCCCBr.Sc1ccccn1>C(C)O>ClCCCCSc1ccccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d1d9d0850f644a438eba335e3ea1f8ab | NCCCSc1ccncc1.O=C(Cl)c1cnc2ccccc2n1>>O=C(NCCCSc1ccncc1)c1cnc2ccccc2n1 | Cl.Cl.NCCCSC1=CC=NC=C1.C(C)N(CC)CC.N1=C(C=NC2=CC=CC=C12)C(=O)Cl>>N1=C(C=NC2=CC=CC=C12)C(=O)NCCCSC1=CC=NC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.Cl[C:2](=[O:1])[c:14]1[cH:15][n:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[n:23]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][n:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[n:23]1 | NCCCSc1ccncc1.O=C(Cl)c1cnc2ccccc2n1 | O=C(NCCCSc1ccncc1)c1cnc2ccccc2n1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCSc1ccncc1)c1cnc2ccccc2n1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1 | 48.9 | [{"value": 48.9, "product": "N1=C(C=NC2=CC=CC=C12)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.8, "product": "N1=C(C=NC2=CC=CC=C12)C(=O)NCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4.30 g (17.8 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 8.68 ml (62.3 mmol) of triethylamine in 200 ml of methylene chloride, 3.43 g (17.8 mmol) of 2-quinoxaloyl chloride was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2nccnc2c1 | HCl | C(Cl)Cl | null | null | NCCCSc1ccncc1.O=C(Cl)c1cnc2ccccc2n1>C(Cl)Cl>O=C(NCCCSc1ccncc1)c1cnc2ccccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-06a787a9c29b4bc098767573585c59cc | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=O)N1>>C=S1C(=O)NC(=O)C1c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 | S1C(NC(C1)=O)=O.C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C.N1CCCCC1>>C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C1C(NC(S1=C)=O)=O | O=[CH:1][c:9]1[cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([OH:17])[c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23]1.[S:2]1[C:3](=[O:4])[NH:5][C:6](=[O:7])[CH2:8]1>>[CH2:1]=[S:2]1[C:3](=[O:4])[NH:5][C:6](=[O:7])[CH:8]1[c:9]1[cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([OH:17])[c:18]([C:19]([CH3:2... | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=O)N1 | C=S1C(=O)NC(=O)C1c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 6e6467835f9a62a25304d3858bc1affbf4c7760e3ef4399f410153ebdcde4e82 | d146119986570e7245608221d3867968dca480d3d9ca0151c47f335a9f4464ad | C=S1C(=O)NC(=O)C1c1ccccc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[O;D1;H0:7]=[C:8]1-[#7:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[S;H0;D2;+0:13]-1>>[CH2;D1;+0:1]=[S;H0;D3;+0:13]1-[C:8](=[O;D1;H0:7])-[#7:9]-[C:10](=[O;D1;H0:11])-[CH;D3;+0:12]-1-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6] | 424.3 | [{"value": 42.8, "product": "C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C1C(NC(S1=C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 424.3, "product": "C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C1C(NC(S1=C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 12.5 g (107 mmol) of 2,4-thiazolidinedione and 25.0 g (107 mmol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde in 300 ml of ethanol, 1.05 ml (10.7 mmol) of piperidine was added, and the mixture was heated under reflux for 5 hours. After cooling, the precipitated crystals were filtered and washed with cool... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | null | c1ccccc1.C1CSCN1 | C1CSCN1.c1ccccc1 | C1CSCN1.c1ccccc1 | Other | C(C)O | null | null | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=O)N1>C(C)O>C=S1C(=O)NC(=O)C1c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1bac2bc6a24d41cca0817ee8dd549bfa | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=S)N1>>CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O | S1C(=S)NC(=O)C1.C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C.N1CCCCC1>>C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O | O=[CH:8][c:7]1[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[c:22]([OH:23])[c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:16]1.[CH2:9]1[S:10][C:11](=[S:12])[NH:13][C:14]1=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[C:9]2[S:10][C:11](=[S:12])[NH:13][C:14]2=[O:15])[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[... | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=S)N1 | CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O | null | null | C(C)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=S)SC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 69.7 | [{"value": 69.7, "product": "C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 14.6 g (110 mmol) of rhodanine and 25.7 g (110 mmol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde in 150 ml of ethanol, 1.08 ml (11.0 mmol) of piperidine was added, and the mixture was heated under reflux for 5 hours. After cooling, the precipitated crystals were filtered and washed with cooled ethanol t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1ccccc1.C1CSCN1 | HO- | C(C)O | null | null | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=S)N1>C(C)O>CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7c0a9d74a2794bf09aa140d9698f4f5f | O=C(NCCCSc1ccncc1)c1cnccn1>>Cl.O=C(NCCCSc1ccncc1)c1cnccn1 | N1=C(C=NC=C1)C(=O)NCCCSC1=CC=NC=C1.Cl.CO>>Cl.Cl.N1=C(C=NC=C1)C(=O)NCCCSC1=CC=NC=C1 | [O:3]=[C:4]([NH:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1)[c:16]1[cH:17][n:18][cH:19][cH:20][n:21]1>>[ClH:2].[O:3]=[C:4]([NH:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1)[c:16]1[cH:17][n:18][cH:19][cH:20][n:21]1 | O=C(NCCCSc1ccncc1)c1cnccn1 | Cl.O=C(NCCCSc1ccncc1)c1cnccn1 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(NCCCSc1ccncc1)c1cnccn1 | null | 85.6 | [{"value": 85.6, "product": "Cl.Cl.N1=C(C=NC=C1)C(=O)NCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 704.5 mg (2.57 mmol) of 4-[3-(2-pyrazinecarbonylamino)propylthio]pyridine in 30 ml of methanol, 70 ml of 10% hydrochloric acid-methanol was added, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off and the residue was purified by recrystallization (solvent: ethan... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.c1cnccn1 | Other | CO | null | 2 | O=C(NCCCSc1ccncc1)c1cnccn1>CO>Cl.O=C(NCCCSc1ccncc1)c1cnccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bcf7a1386a3647debe56a5b796b263a1 | O=C1c2ccccc2C(O)N1CSc1ccncc1>>O=C1c2ccccc2CN1CSc1ccncc1 | O.N.OC1N(C(C2=CC=CC=C12)=O)CSC1=CC=NC=C1.[BH4-].[Na+]>>C1(N(CC2=CC=CC=C12)CSC1=CC=NC=C1)=O | O[CH:9]1[c:8]2[c:3]([cH:4][cH:5][cH:6][cH:7]2)[C:2](=[O:1])[N:10]1[CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][N:10]1[CH2:11][S:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1 | O=C1c2ccccc2C(O)N1CSc1ccncc1 | O=C1c2ccccc2CN1CSc1ccncc1 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 6edf8215b233e57f6f4321f4b7bccecd4275fe90ce30e97960f31ca67074cfef | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | O=C1c2ccccc2CN1CSc1ccncc1 | O-[CH;D3;+0:1]1-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-1:[c:8]>>[C:3]-[#7:2]1-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:6]-[C:4]-1=[O;D1;H0:5] | 54.6 | [{"value": 54.6, "product": "C1(N(CC2=CC=CC=C12)CSC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.6, "product": "C1(N(CC2=CC=CC=C12)CSC1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 681 mg (2.5 mmol) of 4-[(3-hydroxyisoindolin-1-on-2-yl)methylthio]pyridine in 6 ml of trifluoroacetic acid, 0.30 g (7.93 mmol) of sodium borohydride was added in small portions, and the mixture was stirred for 15 minutes. The reaction mixture was poured into cold water and aqueous ammonia was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccncc1 | Other | FC(C(=O)O)(F)F | null | 0.25 | O=C1c2ccccc2C(O)N1CSc1ccncc1>FC(C(=O)O)(F)F>O=C1c2ccccc2CN1CSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ec2bad3e6dba47c4a66e47e6b4dbd056 | Nc1ccccc1C(=O)NCCCSc1ccncc1.O=C(n1ccnc1)n1ccnc1>>O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 | NC1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1>>N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1.c1cn([C:2](n2ccnc2)=[O:1])cn1>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]1[CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | Nc1ccccc1C(=O)NCCCSc1ccncc1.O=C(n1ccnc1)n1ccnc1 | O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 3e8b3bc12468184c65ca5d4345dcd6a9a2bd9361910d94045ee52e07d8a4b796 | fddc47fd7ce043f5eaeb1a75ba9d7112d180caa5d986cf9717333edef1364690 | O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].[O;D1;H0:11]=[C;H0;D3;+0:12](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c;H0;D3;+0:4](=[O;D1;H0:5]):[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:12]:1=[O;D1;H0:11] | 65.7 | [{"value": 65.7, "product": "N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.6, "product": "N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Under nitrogen atmosphere, to a solution of 718 mg (2.5 mmol) of 4-[3-(2-aminobenzoylamino)propylthio]pyridine in 15 ml of tetrahydrofuran. 811 mg (5.0 mmol) of 1,1'carbonyldiimidazole was added, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was dissolved in... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | null | c1ccccc1.c1c[nH]cn1.c1c[nH]cn1 | c1ncc2ccccc2n1 | c1ncc2ccccc2n1.c1ccncc1 | Other | O1CCCC1 | null | 16 | Nc1ccccc1C(=O)NCCCSc1ccncc1.O=C(n1ccnc1)n1ccnc1>O1CCCC1>O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-60d992e5f70047c985ad708eb5f4a3b2 | Nc1ccccc1C(=O)NCCCSc1ccncc1.S=C(n1ccnc1)n1ccnc1>>O=c1c2ccccc2[nH]c(=S)n1CCCSc1ccncc1 | NC1=C(C(=O)NCCCSC2=CC=NC=C2)C=CC=C1.C(=S)(N1C=NC=C1)N1C=NC=C1>>N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=S | [O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9])[NH:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1.c1cn([C:10](n2ccnc2)=[S:11])cn1>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[nH:9][c:10](=[S:11])[n:12]1[CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | Nc1ccccc1C(=O)NCCCSc1ccncc1.S=C(n1ccnc1)n1ccnc1 | O=c1c2ccccc2[nH]c(=S)n1CCCSc1ccncc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 2b1a5626aec4d5fa3a98e3e4c9eb7ca479c1fa140a59f5106857e53480b10644 | ae2e858e699afe0a746047a0d81b45616cc8ac2e8f8c70be12af20e9ea591ceb | O=c1c2ccccc2[nH]c(=S)n1CCCSc1ccncc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].[S;D1;H0:11]=[C;H0;D3;+0:12](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c;H0;D3;+0:12](=[S;D1;H0:11]):[nH;D2;+0:9]:[c:8](:[c:10]):[c:6](:[c:7]):[c;H0;D3;+0:4]:1=[O;D1;H0:5] | 68.5 | [{"value": 68.5, "product": "N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | Under nitrogen atmosphere, to a solution of 1.48 g (5.15 mmol) of 4-[3-(2-aminobenzoylamino)propylthio]pyridine in 30 ml of tetrahydrofuran, 1.84 g (10.3 mmol) of 1,1'-thiocarbonyldiimidazole was added, and the mixture was stirred at room temperature for 64 hours. The solvent was distilled off and the residue was washe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine.Thiocarbonyl | Thiocarbonyl | c1ccccc1.c1c[nH]cn1.c1c[nH]cn1 | c1ncc2ccccc2n1 | c1ncc2ccccc2n1.c1ccncc1 | Other | O1CCCC1 | null | 64 | Nc1ccccc1C(=O)NCCCSc1ccncc1.S=C(n1ccnc1)n1ccnc1>O1CCCC1>O=c1c2ccccc2[nH]c(=S)n1CCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-32b0f994e35548499b85f980112ef12f | Nc1ccccc1C(=O)NCCCCSc1ccccn1.O=C(n1ccnc1)n1ccnc1>>O=c1[nH]c2ccccc2c(=O)n1CCCCSc1ccccn1 | NC1=C(C(=O)NCCCCSC2=NC=CC=C2)C=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1>>N1=C(C=CC=C1)SCCCCN1C(NC2=CC=CC=C2C1=O)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17][c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1.c1cn([C:2](n2ccnc2)=[O:1])cn1>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]1[CH2:13][CH2:14][CH2:15][CH2:16][S:17][c:18]1[cH:19][cH:20][cH:21][... | Nc1ccccc1C(=O)NCCCCSc1ccccn1.O=C(n1ccnc1)n1ccnc1 | O=c1[nH]c2ccccc2c(=O)n1CCCCSc1ccccn1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 3e8b3bc12468184c65ca5d4345dcd6a9a2bd9361910d94045ee52e07d8a4b796 | fddc47fd7ce043f5eaeb1a75ba9d7112d180caa5d986cf9717333edef1364690 | O=c1[nH]c2ccccc2c(=O)n1CCCCSc1ccccn1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10].[O;D1;H0:11]=[C;H0;D3;+0:12](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c;H0;D3;+0:4](=[O;D1;H0:5]):[c:6](:[c:7]):[c:8](:[c:10]):[nH;D2;+0:9]:[c;H0;D3;+0:12]:1=[O;D1;H0:11] | 68.8 | [{"value": 68.8, "product": "N1=C(C=CC=C1)SCCCCN1C(NC2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "N1=C(C=CC=C1)SCCCCN1C(NC2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Under nitrogen atmosphere, to a solution of 452 mg (1.5 mmol) of 2-[4-(2-aminobenzoylamino)butylthio]pyridine in 20 ml of tetrahydrofuran, 486 mg (3.0 mmol) of 1,1'-carbonyldiimidazole was added, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was dissolved in... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | null | c1ccccc1.c1c[nH]cn1.c1c[nH]cn1 | c1ncc2ccccc2n1 | c1ncc2ccccc2n1.c1ccncc1 | Other | O1CCCC1 | null | 16 | Nc1ccccc1C(=O)NCCCCSc1ccccn1.O=C(n1ccnc1)n1ccnc1>O1CCCC1>O=c1[nH]c2ccccc2c(=O)n1CCCCSc1ccccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1dd6d24ee72c4a7caa0ee1e9472a73e8 | ClCCCSc1ccncc1.O=c1[nH]c(=O)c2ccccc2[nH]1>>O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 | O.C1=CC=C2C(=C1)C(=O)NC(=O)N2.ClCCCSC1=CC=NC=C1.C1CCC2=NCCCN2CC1>>N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=O | Cl[CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1.[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[nH:12]1>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]1[CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | ClCCCSc1ccncc1.O=c1[nH]c(=O)c2ccccc2[nH]1 | O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3708cb06644489eacd277cd5ae5b40bafb4efb35fe31ebfe1203528f95cc75ab | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:5](=[O;D1;H0:4]):[c:6]:[c:7]:[#7;a:8]:[c:9]:1=[O;D1;H0:10] | 31.1 | [{"value": 31.1, "product": "N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.0, "product": "N1=CC=C(C=C1)SCCCN1C(NC2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | To a solution of 1.62 g (10 mmol) of benzoylene urea and 1.88 g (10 mmol) of 4-(3-chloropropylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2ccccc2n1 | c1ncc2ccccc2n1 | c1ncc2ccccc2n1.c1ccncc1 | HCl | CN(C=O)C | 80 | 16 | ClCCCSc1ccncc1.O=c1[nH]c(=O)c2ccccc2[nH]1>CN(C=O)C>O=c1[nH]c2ccccc2c(=O)n1CCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9bc7f16969ba4b2985a63d53dcd01956 | C1CCC2=NCCCN2CC1.ClCCCCSc1ccccn1.O=c1[nH]c(=O)c2ccccc2[nH]1>>O=c1c2ccccc2n(CCCCSc2ccccn2)c(=O)n1CCCCSc1ccccn1 | O.C1=CC=C2C(=C1)C(=O)NC(=O)N2.ClCCCCSC1=NC=CC=C1.C1CCC2=NCCCN2CC1>>N1=C(C=CC=C1)SCCCCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=NC=CC=C1)=O | N1=[C:27]2[CH2:31][CH2:30][CH2:29][CH2:32][CH2:33][N:34]2[CH2:24][CH2:25][CH2:26]1.Cl[CH2:10][CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1.[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[nH:9][c:21](=[O:22])[nH:23]1>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[n:9]([CH2:10][CH2:11][CH2:... | C1CCC2=NCCCN2CC1.ClCCCCSc1ccccn1.O=c1[nH]c(=O)c2ccccc2[nH]1 | O=c1c2ccccc2n(CCCCSc2ccccn2)c(=O)n1CCCCSc1ccccn1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d8f534adcea29c7c6c43643fcd89ca9404f765d91ca336bdf1b590b13af086ba | f34bbe5984ba8bee4a20e6b052b51263121b2e0f3c1e349eaacd87d49f81c7ec | O=c1c2ccccc2n(CCCCSc2ccccn2)c(=O)n1CCCCSc1ccccn1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N1=[C;H0;D3;+0:4]2-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[N;H0;D3;+0:10]-2-[CH2;D2;+0:11]-[C:12]-[CH2;D2;+0:13]-1.[O;D1;H0:14]=[c:15]1:[c:16]:[c:17](:[c:18]):[nH;D2;+0:19]:[c:20](=[O;D1;H0:21]):[nH;D2;+0:22]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:19]1:[c:20... | 9 | [{"value": 4.6, "product": "N1=C(C=CC=C1)SCCCCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=NC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.0, "product": "N1=C(C=CC=C1)SCCCCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=NC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | To a solution of 1.62 g (10 mmol) of benzoylene urea and 2.02 g (10 mmol) of 2-(4-chlorobutylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | Monosulfide | C1CCC2=NCCCN2CC1.c1ncc2ccccc2n1 | c1ccc2ncncc2c1.c1ccncc1 | c1ccc2ncncc2c1.c1ccncc1.c1ccncc1 | HCl | CN(C=O)C | 80 | 16 | C1CCC2=NCCCN2CC1.ClCCCCSc1ccccn1.O=c1[nH]c(=O)c2ccccc2[nH]1>CN(C=O)C>O=c1c2ccccc2n(CCCCSc2ccccn2)c(=O)n1CCCCSc1ccccn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-83a7c62c23a249aeb76e978fdd928305 | ClCSc1ccncc1.O=c1[nH]c2ccccc2c(=O)n1CCCCSc1ccncc1>>O=c1c2ccccc2n(CSc2ccncc2)c(=O)n1CCCCSc1ccncc1 | O.N1=CC=C(C=C1)SCCCCN1C(NC2=CC=CC=C2C1=O)=O.ClCSC1=CC=NC=C1.C1CCC2=NCCCN2CC1>>N1=CC=C(C=C1)SCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1)=O | Cl[CH2:10][S:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1.[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[nH:9][c:18](=[O:19])[n:20]1[CH2:21][CH2:22][CH2:23][CH2:24][S:25][c:26]1[cH:27][cH:28][n:29][cH:30][cH:31]1>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[n:9]([CH2:10][S:11][c:12]2[cH:13][cH:14][n:15][cH:16][... | ClCSc1ccncc1.O=c1[nH]c2ccccc2c(=O)n1CCCCSc1ccncc1 | O=c1c2ccccc2n(CSc2ccncc2)c(=O)n1CCCCSc1ccncc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ed0ecfb808bbf35afb68da1838f95fdf0d1e93f83b5a2b57280fca17f7a0b388 | 1a7a00854822988bd22b9e70c1384da74bf98232059fa099ce8b594ffd264593 | O=c1c2ccccc2n(CSc2ccncc2)c(=O)n1CCCCSc1ccncc1 | Cl-[CH2;D2;+0:1]-[#16:2]-[c:3].[C:4]-[#7;a:5]1:[c:6]:[c:7]:[c:8](:[c:9]):[nH;D2;+0:10]:[c:11]:1=[O;D1;H0:12]>>[C:4]-[#7;a:5]1:[c:6]:[c:7]:[c:8](:[c:9]):[n;H0;D3;+0:10](-[CH2;D2;+0:1]-[#16:2]-[c:3]):[c:11]:1=[O;D1;H0:12] | 46.7 | [{"value": 46.7, "product": "N1=CC=C(C=C1)SCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "N1=CC=C(C=C1)SCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | To a solution of 491 mg (1.5 mmol) of 3-[4-(4-pyridylthio)butyl]quinazoline-2,4(1H,3H)-dione and 287 mg (1.8 mmol) of 4-chloromethylthiopyridine in 15 ml of dimethylformamide, 0.27 ml (1.8 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Monosulfide | Monosulfide | c1ncc2ccccc2n1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccncc1.c1ccncc1 | HCl | CN(C=O)C | 80 | 16 | ClCSc1ccncc1.O=c1[nH]c2ccccc2c(=O)n1CCCCSc1ccncc1>CN(C=O)C>O=c1c2ccccc2n(CSc2ccncc2)c(=O)n1CCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-190cc34a0d224df4a3612d1206af180e | ClCCCCSc1ccncc1.O=c1c2ccccc2[nH]c(=S)n1CCCCSc1ccncc1>>O=c1c2ccccc2n(CCCCSc2ccncc2)c(=S)n1CCCCSc1ccncc1 | O.N1=CC=C(C=C1)SCCCCN1C(NC2=CC=CC=C2C1=O)=S.ClCCCCSC1=CC=NC=C1.C1CCC2=NCCCN2CC1>>N1=CC=C(C=C1)SCCCCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1)=S | Cl[CH2:10][CH2:11][CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1.[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[nH:9][c:21](=[S:22])[n:23]1[CH2:24][CH2:25][CH2:26][CH2:27][S:28][c:29]1[cH:30][cH:31][n:32][cH:33][cH:34]1>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[n:9]([CH2:10][CH2:11][CH2:12][... | ClCCCCSc1ccncc1.O=c1c2ccccc2[nH]c(=S)n1CCCCSc1ccncc1 | O=c1c2ccccc2n(CCCCSc2ccncc2)c(=S)n1CCCCSc1ccncc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0024151b25c56ede0e7ce80f2021719ad30c68b18a1f302e7ad0ba2aa518bc5b | d72e642f974cd00fafea01e0aa99ac249acb85af83d41d15686326e5a60030bb | O=c1c2ccccc2n(CCCCSc2ccncc2)c(=S)n1CCCCSc1ccncc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[c:7]:[c:8](:[c:9]):[nH;D2;+0:10]:[c:11]:1=[S;D1;H0:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:11](=[S;D1;H0:12]):[#7;a:5](-[C:4]):[c:6]:[c:7]:[c:8]:1:[c:9] | 97.1 | [{"value": 97.1, "product": "N1=CC=C(C=C1)SCCCCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "N1=CC=C(C=C1)SCCCCN1C(N(C(C2=CC=CC=C12)=O)CCCCSC1=CC=NC=C1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | To a solution of 515 mg (1.5 mmol) of 3-[4-(4-pyridylthio)butyl]quinazoline-2 (1H)-thion-4(3H)-one and 332 mg (1.65 mmol) of 4-(4-chlorobutylthio)pyridine in 15 ml of dimethylformamide, 0.25 ml (1.65 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiocarbonyl | Thiocarbonyl | c1ncc2ccccc2n1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccncc1.c1ccncc1 | HCl | CN(C=O)C | 80 | 16 | ClCCCCSc1ccncc1.O=c1c2ccccc2[nH]c(=S)n1CCCCSc1ccncc1>CN(C=O)C>O=c1c2ccccc2n(CCCCSc2ccncc2)c(=S)n1CCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a61d1f22e885485180fc72a79cdacf3e | CC1(C)NC(=O)N(CCCCSc2ccncc2)C1=O.ClCCCCSc1ccncc1>>CC1(C)C(=O)N(CCCCSc2ccncc2)C(=O)N1CCCCSc1ccncc1 | O.ClCCCCSC1=CC=NC=C1.[H-].[Na+].N1=CC=C(C=C1)SCCCCN1C(NC(C1=O)(C)C)=O>>N1=CC=C(C=C1)SCCCCN1C(=O)N(C(=O)C1(C)C)CCCCSC1=CC=NC=C1 | [CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][S:11][c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[C:18](=[O:19])[NH:20]1.Cl[CH2:21][CH2:22][CH2:23][CH2:24][S:25][c:26]1[cH:27][cH:28][n:29][cH:30][cH:31]1>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][S:11][c:12]2[cH:13][cH... | CC1(C)NC(=O)N(CCCCSc2ccncc2)C1=O.ClCCCCSc1ccncc1 | CC1(C)C(=O)N(CCCCSc2ccncc2)C(=O)N1CCCCSc1ccncc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1d1fbd8c788960a5b6c1c5f03d883d9998e8a29ba0dc902a98e33cdbd0c845a0 | 9068cdf0ef9ef7510e3ed725979384397a613e011a5abb0653feb8d5b2408c81 | O=C1CN(CCCCSc2ccncc2)C(=O)N1CCCCSc1ccncc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7:5]1-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C:12]-1=[O;D1;H0:13]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:6](=[O;D1;H0:7])-[#7:5](-[C:4])-[C:12](=[O;D1;H0:13])-[C:9]-1(-[C;D1;H3:10])-[C;D1;H3:11] | 80.7 | [{"value": 80.7, "product": "N1=CC=C(C=C1)SCCCCN1C(=O)N(C(=O)C1(C)C)CCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "N1=CC=C(C=C1)SCCCCN1C(=O)N(C(=O)C1(C)C)CCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of 96 mg (2.4 mmol) of 60% sodium hydride (oily) in 15 ml of dimethylformamide, 587 mg (2.0 mmol) of 3-[4-(4-pyridylthio)butyl]-5,5-dimethylhydantoin was added, and the mixture was stirred at room temperature for 10 minutes. To this reaction mixture, 807 mg (4.0 mmol) of 4-(4-chlorobutylthio)pyridine wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea | C1C[NH]CN1 | C1C[NH]C[NH]1 | C1C[NH]C[NH]1.c1ccncc1.c1ccncc1 | HCl | CN(C=O)C | null | 0.166667 | CC1(C)NC(=O)N(CCCCSc2ccncc2)C1=O.ClCCCCSc1ccncc1>CN(C=O)C>CC1(C)C(=O)N(CCCCSc2ccncc2)C(=O)N1CCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-100d3d0cc94243f9be6bff4a345d975c | CCC(=O)Nc1ccccc1NC(=O)CC.ClCCCCBr>>CCC(=O)N(CCCCCl)c1ccccc1N(CCCCCl)C(=O)CC | C(CC)(=O)NC1=C(C=CC=C1)NC(CC)=O.BrCCCCCl>>ClCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCCl)C(CC)=O | [CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[NH:17][C:23](=[O:24])[CH2:25][CH3:26].Br[CH2:6][CH2:7][CH2:8][CH2:9][Cl:10]>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][Cl:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][Cl:22])[C:23](=[... | CCC(=O)Nc1ccccc1NC(=O)CC.ClCCCCBr | CCC(=O)N(CCCCCl)c1ccccc1N(CCCCCl)C(=O)CC | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | [OH-].[Na+].C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 4558de55e09b8b817c30da9a143db92605f7343bd4b80f7284db3426de0bb3af | 1b4d57d9adbf5ad6d8d51be36d67937944263d1424dbbd9216901e389aa3cf77 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH;D2;+0:11]-[C:12](-[C:13])=[O;D1;H0:14]):[c:15]>>[C:16]-[C:17]-[N;H0;D3;+0:7](-[C:5](-[C:4])=[O;D1;H0:6])-[c:8](:[c:9]):[c:10](-[N;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:12](-[C:13])=[O;D1;H0:14]):[c:15] | 12.6 | [{"value": 12.6, "product": "ClCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCCl)C(CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.6, "product": "ClCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCCl)C(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a suspension of 3.27 g (15 mmol) of 1,2-di-propionylaminobenzene, 4.32 ml (37.5 mmol) of 4-bromo-1-chlorobutane, and 0.96 g (3.0 mmol) of tetrabutylammonium bromide in 25 ml of toluene, 5.6 ml of 50% aqueous sodium hydroxide was added at room temperature, and the mixture was stirred for 16 hours. The organic layer w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide.Secondary amide | Primary halide.Tertiary amide.Tertiary amide | null | null | c1ccccc1 | Br- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.[OH-].[Na+].C1(=CC=CC=C1)C | null | 16 | CCC(=O)Nc1ccccc1NC(=O)CC.ClCCCCBr>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.[OH-].[Na+].C1(=CC=CC=C1)C>CCC(=O)N(CCCCCl)c1ccccc1N(CCCCCl)C(=O)CC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-037000249bf248819c335444fe0d73ae | CCC(=O)N(CCCCCl)c1ccccc1N(CCCCCl)C(=O)CC.Sc1ccncc1>>CCC(=O)N(CCCCSc1ccncc1)c1ccccc1N(CCCCSc1ccncc1)C(=O)CC | O.SC1=CC=NC=C1.[OH-].[K+].ClCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCCl)C(CC)=O>>N1=CC=C(C=C1)SCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCSC1=CC=NC=C1)C(CC)=O | Cl[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[N:23]([CH2:24][CH2:25][CH2:26][CH2:31]Cl)[C:35](=[O:36])[CH2:37][CH3:38].[SH:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][... | CCC(=O)N(CCCCCl)c1ccccc1N(CCCCCl)C(=O)CC.Sc1ccncc1 | CCC(=O)N(CCCCSc1ccncc1)c1ccccc1N(CCCCSc1ccncc1)C(=O)CC | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | 0a603e62127a82876015e05ff0fdd4be754b3daaa7727a875a252d121d24df21 | 48e4666c504a6dac125cad805af6583baf72152192dc93c9aef146ff85aee226 | c1ccc(NCCCCSc2ccncc2)c(NCCCCSc2ccncc2)c1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].Cl-[CH2;D2;+0:5]-[C:6]-[C:7].[SH;D1;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C:4]-[C:3]-[CH2;D2;+0:2]-[C:15]-[#16:16]-[c:17]:[c:18]:[cH;D2;+0:1]:[#7;a:19]:[c:20].[C:7]-[C:6]-[CH2;D2;+0:5]-[S;H0;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 81 | [{"value": 81.0, "product": "N1=CC=C(C=C1)SCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCSC1=CC=NC=C1)C(CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "N1=CC=C(C=C1)SCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCSC1=CC=NC=C1)C(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 525 mg (4.7 mmol) of 4-mercaptopyridine and 265 mg (4.7 mmol) of potassium hydroxide in 20 ml of dimethyl sulfoxide, 760 mg (1.89 mmol) of 1,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene was added at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was poured into wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic thiol | Monosulfide.Monosulfide | null | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccncc1 | null | CS(=O)C | null | 2 | CCC(=O)N(CCCCCl)c1ccccc1N(CCCCCl)C(=O)CC.Sc1ccncc1>CS(=O)C>CCC(=O)N(CCCCSc1ccncc1)c1ccccc1N(CCCCSc1ccncc1)C(=O)CC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-84de096b7dbe4838b438dd20613401fa | Cl>>Cl.Cl | N1=CC=C(C=C1)SCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCSC1=CC=NC=C1)C(CC)=O.Cl.CO>>Cl.Cl.N1=CC=C(C=C1)SCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCSC1=CC=NC=C1)C(CC)=O | [ClH:39]>>[ClH:39].[ClH:40] | Cl | Cl.Cl | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 74.1 | [{"value": 74.1, "product": "Cl.Cl.N1=CC=C(C=C1)SCCCCN(C(CC)=O)C1=C(C=CC=C1)N(CCCCSC1=CC=NC=C1)C(CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 840 mg (1.53 mmol) of 1,2-bis[N-[4-(4-pyridylthio)butyl]-N-propionylamino]benzene in 20 ml of methanol, 80 ml of 10% hydrochloric acid/methanol was added, and the mixture was stirred for 30 minutes. The solvent was distilled off and the residue was recrystallized from ethanol/ether to give 707 mg of th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CO | null | 0.5 | Cl>CO>Cl.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-15f297c6101148ec9fd927b43a15d2da | CC(C)(C)OC(=O)NCCCSc1ccncc1.O=C(OO)c1cccc(Cl)c1>>CC(C)(C)OC(=O)NCCCS(=O)c1ccncc1 | C(C)(C)(C)OC(=O)NCCCSC1=CC=NC=C1.ClC1=CC(=CC=C1)C(=O)OO>>C(C)(C)(C)OC(=O)NCCCS(=O)C1=CC=NC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][S:12][c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1.O=C(O[OH:13])c1cccc(Cl)c1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][S:12](=[O:13])[c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | CC(C)(C)OC(=O)NCCCSc1ccncc1.O=C(OO)c1cccc(Cl)c1 | CC(C)(C)OC(=O)NCCCS(=O)c1ccncc1 | null | null | C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | c1ccncc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C:2]-[C:3]-[S;H0;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:2]-[C:3]-[S;H0;D3;+0:4](=[O;H0;D1;+0:1])-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 79 | [{"value": 78.9, "product": "C(C)(C)(C)OC(=O)NCCCS(=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "C(C)(C)(C)OC(=O)NCCCS(=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4.03 g (15.0 mmol) of 4-[3-(t-butoxycarbonylamino)propylthio]pyridine in 100 ml of methylene chloride, 3.05 g (15.0 mmol) of m-chloroperbenzoic acid was added with stirring under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed two times with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccncc1 | HCl | C(Cl)Cl | null | null | CC(C)(C)OC(=O)NCCCSc1ccncc1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CC(C)(C)OC(=O)NCCCS(=O)c1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4aaaa3a6821445dabee298f6b50af2bd | ClCCCCBr.Sc1ccncc1>>ClCCCCSc1ccncc1 | SC1=CC=NC=C1.BrCCCCCl.C(C)N(CC)CC>>ClCCCCSC1=CC=NC=C1 | Br[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1].[SH:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1 | ClCCCCBr.Sc1ccncc1 | ClCCCCSc1ccncc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 89.7 | [{"value": 89.7, "product": "ClCCCCSC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.7, "product": "ClCCCCSC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a suspension of 33.35 g (0.30 mol) of 4-mercaptopyridine and 51.44 g (0.30 mol) of 1-bromo-4-chlorobutane in 500 ml of ethanol, 41.9 ml (0.30 mol) of triethylamine was added, and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off and chloroform was added to the residue. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1 | HBr | C(C)O | null | 5 | ClCCCCBr.Sc1ccncc1>C(C)O>ClCCCCSc1ccncc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0ab8bbc1253f48d2a40e581350c80b04 | C=CC(=O)Cl.COC1(c2ccccc2)OCC(CO)O1>>C=CC(=O)OCC1COC(OC)(c2ccccc2)O1 | OCC1OC(OC1)(C1=CC=CC=C1)OC.C(C)N(CC)CC.C(C=C)(=O)Cl>>C(C=C)(=O)OCC1OC(OC1)(C1=CC=CC=C1)OC | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][O:9][C:10]([O:11][CH3:12])([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[O:19]1>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][O:9][C:10]([O:11][CH3:12])([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[O:19]1 | C=CC(=O)Cl.COC1(c2ccccc2)OCC(CO)O1 | C=CC(=O)OCC1COC(OC)(c2ccccc2)O1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccc(C2OCCO2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4] | null | [] | null | null | null | null | The procedure of Example A was repeated, employing 21 grams (100 mmol.) of 4-hydroxymethyl-2-methoxy-2-phenyl-1,3-dioxolane, 25.3 grams (250 mmol.) of triethylamine, 9.5 grams (105 mmol.) of acryloyl chloride and 150 ml. of methylene chloride. The crude product was purified by column chromatography over basic alumina, ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1COCO1.c1ccccc1 | HCl | C(Cl)Cl | null | null | C=CC(=O)Cl.COC1(c2ccccc2)OCC(CO)O1>C(Cl)Cl>C=CC(=O)OCC1COC(OC)(c2ccccc2)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b17abff2b44840dd9b7ca02149e953e2 | Nc1ccc(Nc2ccccc2)cc1.O=C(O)CCS>>O=C(CCS)Nc1ccc(Nc2ccccc2)cc1 | C1(=CC=CC=C1)NC1=CC=C(C=C1)N.SCCC(=O)O.C=1(C(=CC=CC1)C)C>>N(C1=CC=CC=C1)C1=CC=C(C=C1)NC(CCS)=O | [NH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1.O[C:2](=[O:1])[CH2:3][CH2:4][SH:5]>>[O:1]=[C:2]([CH2:3][CH2:4][SH:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1 | Nc1ccc(Nc2ccccc2)cc1.O=C(O)CCS | O=C(CCS)Nc1ccc(Nc2ccccc2)cc1 | null | null | CCCCCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 140 | CELSIUS | null | null | A mixture of 18.4 grams of N-phenyl-p-phenylene diamine, 10.6 grams of β-mercaptopropionic acid and 120 milliliters of xylene (technical grade) was heated to reflux (about 140° C.) under nitrogen atmosphere, with stirring. A 1.6 milliliter quantity of water (90% of theory) was removed from this mixture by azetropic dis... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CCCCCC | 140 | null | Nc1ccc(Nc2ccccc2)cc1.O=C(O)CCS>CCCCCC>O=C(CCS)Nc1ccc(Nc2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e9e9e922e064d3ba03f213d5729e9eb | N#Cc1c(Oc2ccc3c(c2)C=C3)cccc1Oc1ccc2c(c1)C=C2>>NCc1c(Oc2ccc3c(c2)C=C3)cccc1Oc1ccc2c(c1)C=C2 | C1=CC2=C1C=CC(=C2)OC2=C(C#N)C(=CC=C2)OC2=CC1=C(C=C1)C=C2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C1=CC2=C1C=CC(=C2)OC2=C(CN)C(=CC=C2)OC2=CC1=C(C=C1)C=C2 | [N:1]#[C:2][c:3]1[c:4]([O:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[CH:12]=[CH:13]3)[cH:14][cH:15][cH:16][c:17]1[O:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24]1)[CH:25]=[CH:26]2>>[NH2:1][CH2:2][c:3]1[c:4]([O:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[CH:12]=[CH:13]3)[cH:14][cH:15][cH:16][c:17]1[O:18][c:19]1[cH:20][cH... | N#Cc1c(Oc2ccc3c(c2)C=C3)cccc1Oc1ccc2c(c1)C=C2 | NCc1c(Oc2ccc3c(c2)C=C3)cccc1Oc1ccc2c(c1)C=C2 | null | null | C(C)OCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1=Cc2cc(Oc3cccc(Oc4ccc5c(c4)C=C5)c3)ccc21 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 15 | MINUTE | In a 500 ml, 4-necked round-bottomed flask equipped with an overhead mechanical stirrer, a thermometer/adaptor, a reflux condensor and a funnel was added 2,6-di-(4-benzocyclobutenoxy)benzonitrile followed by 260 ml of anhydrous diethyl ether. The resultant mixture was placed in an ice bath and stirred under anitrogen a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.C1=Cc2ccccc21.C1=Cc2ccccc21 | null | C(C)OCC | null | 0.25 | N#Cc1c(Oc2ccc3c(c2)C=C3)cccc1Oc1ccc2c(c1)C=C2>C(C)OCC>NCc1c(Oc2ccc3c(c2)C=C3)cccc1Oc1ccc2c(c1)C=C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-71e3ae6057b24905aebe514e2d6cc7ed | BrCCCCCCCCCCBr.CC(C)=O.COc1cc(C=O)ccc1O.O=C([O-])[O-]>>COc1cc(C=O)ccc1OCCCCCCCCCCOc1ccc(C=O)cc1OC | O=CC1=CC(OC)=C(O)C=C1.BrCCCCCCCCCCBr.C([O-])([O-])=O.[K+].[K+].CC(=O)C>>COC1=C(OCCCCCCCCCCOC2=C(C=C(C=C2)C=O)OC)C=CC(=C1)C=O | Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.O=[C:3]([CH3:1])[CH3:24].[c:5]1([CH:6]=[O:7])[cH:8][cH:9][c:23]([OH:22])[c:30]([O:31][CH3:32])[cH:29]1.[O-:2][C:27]([O-:11])=[O:28]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][C... | BrCCCCCCCCCCBr.CC(C)=O.COc1cc(C=O)ccc1O.O=C([O-])[O-] | COc1cc(C=O)ccc1OCCCCCCCCCCOc1ccc(C=O)cc1OC | null | null | O | Aromatic Heterocycle Formation | OtherReaction | d8b09204afcff0574fcc1e547d0c752ec6c19e94f0279576b6ad2c5cb824ae19 | 325f167d8f5f8c8d486fe211b7741ee3cecfa3178b343d3635d0779e7f4b61df | c1ccc(OCCCCCCCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].Br-[CH2;D2;+0:4]-[C:5]-[C:6].O=[C;H0;D3;+0:7](-[CH3;D1;+0:8])-[CH3;D1;+0:9].[#8:10]-[c:11]1:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[C:14]=[O;D1;H0:15]):[c:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18]:1-[OH;D1;+0:19].[O-;H0;D1:20]-[C;H0;D3;+0:21](-[O-;H0;D1:22])=[O;D1;H0:23]>>[#8:10]-[c:11]1:[cH;D2;+0:12]:[c:2... | null | [] | 5 | CELSIUS | 48 | HOUR | A slurry of 13.42 g of vanillin, 11.99 g of 1,10-dibromodecane, 6.16 g of anhydrous potassium carbonate and 300 ml of acetone was refluxed with stirring for 48 h, cooled and diluted with 400 ml of water. After the salts had dissolved, the mixture was chilled overnight at 5° C. The solid product was filtered, washed twi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aldehyde.Ketone.Aromatic alcohol | Aldehyde.Aldehyde.Ether.Ether.Ether | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | O | 5 | 48 | BrCCCCCCCCCCBr.CC(C)=O.COc1cc(C=O)ccc1O.O=C([O-])[O-]>O>COc1cc(C=O)ccc1OCCCCCCCCCCOc1ccc(C=O)cc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-68af85f3122543a7bc6f77f268cb1285 | CC(=O)c1ccc(F)cc1.Oc1ccc(C(c2ccccc2)(c2ccc(O)cc2)C(F)(F)F)cc1.Oc1cccc(-c2ccccc2O)c1>>CC(=O)c1ccc(Oc2ccc(C(c3ccccc3)(c3ccc(Oc4ccc(C(C)=O)cc4)cc3)C(F)(F)F)cc2)cc1 | C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C=C1)C(C(F)(F)F)(C1=CC=CC=C1)C1=CC=C(C=C1)O.C1=CC=C(C(=C1)C2=CC(=CC=C2)O)O.CC(=O)C1=CC=C(C=C1)F.C1=CC=C(C(=C1)C2=CC(=CC=C2)O)O>>C(C)(=O)C1=CC=C(OC2=CC=C(C=C2)C(C(F)(F)F)(C2=CC=CC=C2)C2=CC=C(C=C2)OC2=CC=C(C=C2)C(C)=O)C=C1 | F[c:25]1[cH:26][cH:27][c:28]([C:29]([CH3:30])=[O:31])[cH:32][cH:33]1.[OH:8][c:9]1[cH:10][cH:11][c:12]([C:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)([c:20]2[cH:21][cH:22][c:23]([OH:24])[cH:34][cH:35]2)[C:36]([F:37])([F:38])[F:39])[cH:40][cH:41]1.Oc1cc[cH:1]c(-[c:4]2[cH:5][cH:6][cH:7][cH:42][c:43]2O)c1>>[CH3:1][C:2... | CC(=O)c1ccc(F)cc1.Oc1ccc(C(c2ccccc2)(c2ccc(O)cc2)C(F)(F)F)cc1.Oc1cccc(-c2ccccc2O)c1 | CC(=O)c1ccc(Oc2ccc(C(c3ccccc3)(c3ccc(Oc4ccc(C(C)=O)cc4)cc3)C(F)(F)F)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a384ee17c5b86ec6db3aa57afcafb5f4f8d0f89875ab9fb8f6d7035197efba77 | 64d1960390043da01c7e3d5fa149706f0e8b47a38c6e1cb9dc5f08e732a60424 | c1ccc(Oc2ccc(C(c3ccccc3)c3ccc(Oc4ccccc4)cc3)cc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-[c;H0;D3;+0:6]1:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:1-c1:[cH;D2;+0:12]:c:c:c(-O):c:1.[OH;D1;+0:13]-[c:14](:[c:15]):[c:16].[OH;D1;+0:17]-[c:18](:[c:19]):[c:20]>>[CH3;D1;+0:12]-[C:21](=[O;D1;H0:22])-[c;H0;D3;+0:11]1:[c:10]:[c:9]:[c;H0;D3;+0:8](-[O;H0;D2;+0:17]-[c:1... | null | [] | null | null | null | null | A suspension of 15.2 grams (0.11 moles) anhydrous potassium carbonate in 370 milliliters of N2N'-dimethylacetamide is prepared in a 1 liter, 2-necked round bottom flask equipped with a reflux condensor and a nitrogen gas inlet. To the suspension is added 16.61 grams (0.05 moles) of 1,1-bis-(4-hydroxyphenyl)-1-phenyl-2,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | Ketone.Ether.Ether | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HF | null | null | null | CC(=O)c1ccc(F)cc1.Oc1ccc(C(c2ccccc2)(c2ccc(O)cc2)C(F)(F)F)cc1.Oc1cccc(-c2ccccc2O)c1>>CC(=O)c1ccc(Oc2ccc(C(c3ccccc3)(c3ccc(Oc4ccc(C(C)=O)cc4)cc3)C(F)(F)F)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7ba62443ec7649e18842d3f4e41dec27 | COc1ccccc1.O=C(c1ccccc1)C(F)(F)F>>Oc1ccc(C(c2ccccc2)(c2ccc(O)cc2)C(F)(F)F)cc1 | FC(C(=O)C1=CC=CC=C1)(F)F.FC(S(=O)(=O)O)(F)F.C1(=CC=CC=C1)OC.Br>>OC1=CC=C(C=C1)C(C(F)(F)F)(C1=CC=CC=C1)C1=CC=C(C=C1)O | [CH3:4][O:17][c:16]1[cH:15][cH:14][cH:13][cH:19][cH:18]1.[O:1]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:20]([F:21])([F:22])[F:23]>>[OH:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)([c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]2)[C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]1 | COc1ccccc1.O=C(c1ccccc1)C(F)(F)F | Oc1ccc(C(c2ccccc2)(c2ccc(O)cc2)C(F)(F)F)cc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | a72ec60e45c36f8c7f1bc4c1f3a2bfbd3a7fbd4644c34189c3a0c1d7665ae4d4 | 604a51ed69f11cbca51f2d4914d9db2bcecd47e66534bb9a0d52940ec959a73c | c1ccc(C(c2ccccc2)c2ccccc2)cc1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1.[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[c:15](:[c:16]):[c:17]>>[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[C;H0;D4;+0:13](-[c:18]1:[c:19]:[c:20]:[c:21](-[OH;D1;+0:14]):[c:22]:[cH;D2;+0:1]:1)(-[c:... | null | [] | null | null | 24 | HOUR | A mixture of 100 grams (0.57 mol) of trifluoroacetophenone, 100 grams (0.7 mol) trifluoromethane sulfonic acid, and 100 grams (10.9 mol) anisole is stirred at room temperature for 24 hours. The mixture is then transferred to a separatory funnel and the organic material is washed with water (3×11), saturated bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)O | null | 24 | COc1ccccc1.O=C(c1ccccc1)C(F)(F)F>C(C)(=O)O>Oc1ccc(C(c2ccccc2)(c2ccc(O)cc2)C(F)(F)F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5e96e77a6ea242f0b4bfc5496ffdd983 | CCNCCO.O=Cc1ccc(F)cc1>>CCN(CCO)c1ccc(C=O)cc1 | FC1=CC=C(C=O)C=C1.C(C)NCCO.C([O-])([O-])=O.[K+].[K+]>>OCCN(CC)C1=CC=C(C=O)C=C1 | [CH3:1][CH2:2][NH:3][CH2:4][CH2:5][OH:6].F[c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][OH:6])[c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13][cH:14]1 | CCNCCO.O=Cc1ccc(F)cc1 | CCN(CCO)c1ccc(C=O)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C;D1;H3:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C;D1;H3:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 95 | CELSIUS | null | null | To a three neck flask fitted with a mechanical stirrer, a thermometer, and a condenser, is added 124 g (1 mole) of 4-fluorobenzaldehyde, 89.1 g (1 mole) of 2-(N-ethylamino)ethanol, 138.2 g (1 mole) of anhydrous potassium carbonate, and dimethylsulfoxide. The mixture is heated at 95° C. for 3 hours. After cooling to roo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CS(=O)C | 95 | null | CCNCCO.O=Cc1ccc(F)cc1>CS(=O)C>CCN(CCO)c1ccc(C=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e8332f792cb943259f780b7e96c92708 | CCN(CCOC(C)=O)c1ccc(C=O)cc1>>CCN(CCO)c1ccc(C=CC=O)cc1 | [Cl-].[Na+].C(C)(=O)OCCN(CC)C1=CC=C(C=O)C=C1.[Br-].O1C(OCC1)C[P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+]>>OCCN(CC)C1=CC=C(C=CC=O)C=C1 | O=[CH:11][c:10]1[cH:9][cH:8][c:7]([N:3]([CH2:2][CH3:1])[CH2:4][CH2:5][O:6][C:13]([CH3:12])=[O:14])[cH:16][cH:15]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][OH:6])[c:7]1[cH:8][cH:9][c:10]([CH:11]=[CH:12][CH:13]=[O:14])[cH:15][cH:16]1 | CCN(CCOC(C)=O)c1ccc(C=O)cc1 | CCN(CCO)c1ccc(C=CC=O)cc1 | null | null | CN(C=O)C.Cl.O | Miscellaneous | OtherReaction | 716d431b21b76dc7be86288acf6b079ba424a010e3c36e2883035373997c7f75 | 8312bfe1cc7896204f42ca6a876ec15c050ef293944cf9da7ac1091018dad53e | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:8](-[CH3;D1;+0:9])=[O;D1;H0:10]>>[C:5]-[C:6]-[OH;D1;+0:7].[O;D1;H0:10]=[CH;D2;+0:8]-[CH;D2;+0:9]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | 16 | HOUR | To a solution of 235.3 g (1 mole) of 4-(N-2-acetoxyethyl-N-ethylamino)benzaldehyde in dimethylformamide is added 738.7 g (2.0 moles) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide, and the mixture is heated at 90° C. Potassium t-butoxide (224.4 g, 2.0 moles) is added, and heating is continue... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Aldehyde.Primary alcohol | null | null | c1ccccc1 | Other | CN(C=O)C.Cl.O | 90 | 16 | CCN(CCOC(C)=O)c1ccc(C=O)cc1>CN(C=O)C.Cl.O>CCN(CCO)c1ccc(C=CC=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a7fdbb7f8cd94053be30d2daa540915e | CCN(CCO)c1ccc(C=CC=O)cc1.Nc1ccccc1.O=C(O)Cc1ccc([N+](=O)[O-])cc1>>CCN(CCO)C(=CC=Cc1ccccc1)c1ccc([N+](=O)[O-])cc1 | OCCN(CC)C1=CC=C(C=CC=O)C=C1.NC1=CC=CC=C1.C=1(C(=CC=CC1)S(=O)(=O)O)C.C(C(=C)C)(=O)O.[N+](=O)([O-])C1=CC=C(C=C1)CC(=O)O>>OCCN(CC)C(=CC=CC1=CC=CC=C1)C1=CC=C(C=C1)[N+](=O)[O-] | O=C[CH:9]=[CH:10][c:11]1ccc([N:3]([CH2:2][CH3:1])[CH2:4][CH2:5][OH:6])c[cH:16]1.Nc1c[cH:15][cH:14][cH:13][cH:12]1.O=[C:8](O)[CH2:7][c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][OH:6])[C:7](=[CH:8][CH:9]=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[... | CCN(CCO)c1ccc(C=CC=O)cc1.Nc1ccccc1.O=C(O)Cc1ccc([N+](=O)[O-])cc1 | CCN(CCO)C(=CC=Cc1ccccc1)c1ccc([N+](=O)[O-])cc1 | null | null | C1(=CC=CC=C1)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 9e2980e417c83e0bf41fd27676942bc4bd19d262e4edb49eda3aeea031ce50ea | 1a583843e9b96e1db3bc4296c45825b4414c285767a137bcc7a95757ef2442ec | C(C=Cc1ccccc1)=Cc1ccccc1 | N-c1:[cH;D2;+0:1]:[c:2]:[c:3]:[cH;D2;+0:4]:c:1.O-[C;H0;D3;+0:5](=O)-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9].O=C-[CH;D2;+0:10]=[C:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:c:c(-[N;H0;D3;+0:14](-[C:15]-[C;D1;H3:16])-[C:17]-[C:18]):c:c:1>>[C:18]-[C:17]-[N;H0;D3;+0:14](-[C:15]-[C;D1;H3:16])-[C;H0;D3;+0:6](=[CH;D2;+0:5]-[CH;D2;+0:10]=[C... | null | [] | null | null | 3 | HOUR | A solution of 21.9 g (0.1 mole) of 4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde, 9.3 g (1 mole) of aniline, and 0.19 g (1 mole %) of toluenesulfonic acid in toluene is heated at reflux for 17 hours with azeotropic removal of water. After the mixture is cooled to room temperature, 17.2 g (0.2 mole) of methacrylic aci... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Primary amine.Tertiary amine | Enamine.Conjugated diene | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.O | null | 3 | CCN(CCO)c1ccc(C=CC=O)cc1.Nc1ccccc1.O=C(O)Cc1ccc([N+](=O)[O-])cc1>C1(=CC=CC=C1)C.O>CCN(CCO)C(=CC=Cc1ccccc1)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4683026ba7114d0ab4a570be14f1d8a7 | CCCCNCCCCO.O=Cc1ccc(F)cc1>>CCCCN(CCCCO)c1ccc(C=O)cc1 | FC1=CC=C(C=O)C=C1.C(CCC)NCCCCO.C([O-])([O-])=O.[K+].[K+]>>OCCCCN(CCCC)C1=CC=C(C=O)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].F[c:11]1[cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[c:11]1[cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1 | CCCCNCCCCO.O=Cc1ccc(F)cc1 | CCCCN(CCCCO)c1ccc(C=O)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 95 | CELSIUS | null | null | To a three neck flask fitted with a mechanical stirrer, a thermometer, and a condenser, is added 124 g (1 mole) of 4-fluorobenzaldehyde, 145.3 g (1 mole) of N-butyl-N-4-hydroxybutylamine, 138.2 g (1 mole) of anhydrous potassium carbonate, and dimethylsulfoxide. The mixture is then heated at 95° C. until the reaction is... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CS(=O)C | 95 | null | CCCCNCCCCO.O=Cc1ccc(F)cc1>CS(=O)C>CCCCN(CCCCO)c1ccc(C=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3b600f4c7ca4476a9e47d62d4b288b7e | CC(=O)OC(C)=O.CCCCN(CCCCO)c1ccc(C=O)cc1>>CCCCN(CCCCOC(C)=O)c1ccc(C=O)cc1 | OCCCCN(CCCC)C1=CC=C(C=O)C=C1.C(C)(=O)OC(C)=O.C(C)N(CC)CC>>C(C)(=O)OCCCCN(CCCC)C1=CC=C(C=O)C=C1 | CC(=O)O[C:11]([CH3:12])=[O:13].[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[c:14]1[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]([CH3:12])=[O:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]1 | CC(=O)OC(C)=O.CCCCN(CCCCO)c1ccc(C=O)cc1 | CCCCN(CCCCOC(C)=O)c1ccc(C=O)cc1 | null | null | ClCCl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 16 | HOUR | To a stirred solution of 249.4 g (1 mole) of 4-(N-4-hydroxybutyl-N-butylamino)benzaldehyde in dichloromethane are added 153.1 g (1.5 moles) of acetic anhydride, 151.8 g (1.5 moles) of triethylamine, and 8.5 g (7 mole %) of 4-N,N-dimethylaminopyridine. The reaction mixture is stirred at room temperature for 16 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | ClCCl | null | 16 | CC(=O)OC(C)=O.CCCCN(CCCCO)c1ccc(C=O)cc1>ClCCl>CCCCN(CCCCOC(C)=O)c1ccc(C=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a8052ae73acf41bcbeb0aa54d437ed4a | CCCCN(CCCCOC(C)=O)c1ccc(C=O)cc1>>CCCCN(CCCCO)c1ccc(C=CC=O)cc1 | [Cl-].[Na+].C(C)(=O)OCCCCN(CCCC)C1=CC=C(C=O)C=C1.[Br-].O1C(OCC1)C[P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+]>>OCCCCN(CCCC)C1=CC=C(C=CC=O)C=C1 | O=[CH:15][c:14]1[cH:13][cH:12][c:11]([N:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:17]([CH3:16])=[O:18])[cH:20][cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[c:11]1[cH:12][cH:13][c:14]([CH:15]=[CH:16][CH:17]=[O:18])[cH:19][cH:20]1 | CCCCN(CCCCOC(C)=O)c1ccc(C=O)cc1 | CCCCN(CCCCO)c1ccc(C=CC=O)cc1 | null | null | CN(C=O)C.Cl.O | Miscellaneous | OtherReaction | 716d431b21b76dc7be86288acf6b079ba424a010e3c36e2883035373997c7f75 | 8312bfe1cc7896204f42ca6a876ec15c050ef293944cf9da7ac1091018dad53e | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:8](-[CH3;D1;+0:9])=[O;D1;H0:10]>>[C:5]-[C:6]-[OH;D1;+0:7].[O;D1;H0:10]=[CH;D2;+0:8]-[CH;D2;+0:9]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | 16 | HOUR | To a solution of 29.1 g (0.1 mole) of 4-(N-4-acetoxybutyl-N-butylamino)benzaldehyde in dimethylformamide is added 73.9 g (0.2 mole) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide, and the mixture is heated at 90° C. Potassium t-butoxide (22.4 g, 0.2 mole) is added, and heating is continued a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Aldehyde.Primary alcohol | null | null | c1ccccc1 | Other | CN(C=O)C.Cl.O | 90 | 16 | CCCCN(CCCCOC(C)=O)c1ccc(C=O)cc1>CN(C=O)C.Cl.O>CCCCN(CCCCO)c1ccc(C=CC=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7218c825a19c4b7087dc142778ad78c1 | Cc1ccc(S(=O)(=O)C(F)(F)F)cc1.O=C1CCC(=O)N1Br>>O=S(=O)(c1ccc(CBr)cc1)C(F)(F)F | S(=O)(=O)(C(F)(F)F)C1=CC=C(C=C1)C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>S(=O)(=O)(C(F)(F)F)C1=CC=C(C=C1)CBr | [O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:10][cH:11]1)[C:12]([F:13])([F:14])[F:15].O=C1CCC(=O)N1[Br:9]>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([CH2:8][Br:9])[cH:10][cH:11]1)[C:12]([F:13])([F:14])[F:15] | Cc1ccc(S(=O)(=O)C(F)(F)F)cc1.O=C1CCC(=O)N1Br | O=S(=O)(c1ccc(CBr)cc1)C(F)(F)F | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 4366c8ed5252d87d3b8aede79b191acca5264a1f31dcbbbe406186fea61ecf72 | 0e509ce434521037e1886dc905c022287322e8fdd0d4706b9bfbbfdc0a5969b8 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A stirred solution of 22.4 g (0.1 mole) of 4-triflyltoluene, 178 g (0.1 mole) of N-bromosuccinimide, and 0.48 g (0.2 mole %) of benzoyl peroxide in carbon tetrachloride is heated at reflux for 20 hours. After cooling to room temperature, the reaction is diluted by the addition of carbon tetrachloride, and the solid byp... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(S(=O)(=O)C(F)(F)F)cc1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>O=S(=O)(c1ccc(CBr)cc1)C(F)(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c752070c8b524cd1886a9e0e3e0ee605 | O=S(=O)(c1ccc(CBr)cc1)C(F)(F)F.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>O=S(=O)(c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1)C(F)(F)F.[Br-] | S(=O)(=O)(C(F)(F)F)C1=CC=C(C=C1)CBr.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].S(=O)(=O)(C(F)(F)F)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 | [O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([CH2:8][Br:34])[cH:28][cH:29]1)[C:30]([F:31])([F:32])[F:33].[P:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([CH2:8][P+:9]([c:10]2[cH:11][cH:... | O=S(=O)(c1ccc(CBr)cc1)C(F)(F)F.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | O=S(=O)(c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1)C(F)(F)F.[Br-] | null | null | C=1(C(=CC=CC1)C)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | null | [] | null | null | null | null | A solution of 30.3 g (0.1 mole) of 4-triflyl-alpha-bromotoluene and 28.8 g (0.1 mole) of triphenylphosphine in xylene is heated at reflux for 19 hours. 4-Triflylbenzyltriphenylphosphonium bromide is then isolated by filtration, washed with additional portions of xylene, and dried.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C=1(C(=CC=CC1)C)C | null | null | O=S(=O)(c1ccc(CBr)cc1)C(F)(F)F.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C=1(C(=CC=CC1)C)C>O=S(=O)(c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1)C(F)(F)F.[Br-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d48d928ccbcc4d238b26df05d712c5e6 | CCCCN(CCCCO)c1ccc(C=CC=O)cc1.O=S(=O)(c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1)C(F)(F)F>>CCCCN(CCCCO)C(=CC=Cc1ccccc1)c1ccc(S(=O)(=O)C(F)(F)F)cc1 | O.OCCCCN(CCCC)C1=CC=C(C=CC=O)C=C1.[Br-].S(=O)(=O)(C(F)(F)F)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Li]CCCC>>OCCCCN(CCCC)C(=CC=CC1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)C(F)(F)F | O=[CH:12][CH:13]=[CH:14][c:15]1ccc([N:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][CH2:8][CH2:9][OH:10])c[cH:20]1.c1ccc([P+](c2ccccc2)(c2c[cH:19][cH:18][cH:17][cH:16]2)[CH2:11][c:21]2[cH:22][cH:23][c:24]([S:25](=[O:26])(=[O:27])[C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]2)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6... | CCCCN(CCCCO)c1ccc(C=CC=O)cc1.O=S(=O)(c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1)C(F)(F)F | CCCCN(CCCCO)C(=CC=Cc1ccccc1)c1ccc(S(=O)(=O)C(F)(F)F)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | ccfa34830e99154215dc9efa804c077a8eae3d186500f5a39b4a3d89c379fb59 | 486671fa43642ccee0acbfcc882f81c1972f06f8ac2d1775b3a21b51993e48a6 | C(C=Cc1ccccc1)=Cc1ccccc1 | O=[CH;D2;+0:1]-[C:2]=[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:c:c(-[N;H0;D3;+0:6](-[C:7]-[C:8])-[C:9]-[C:10]):c:c:1.[c:11]:[c:12](-[CH2;D2;+0:13]-[P+](-c1:[cH;D2;+0:14]:[c:15]:[c:16]:[cH;D2;+0:17]:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:18]>>[C:8]-[C:7]-[N;H0;D3;+0:6](-[C:9]-[C:10])-[C;H0;D3;+0:13](=[CH;D2;+0:1]-[C:2]=[C:3]... | null | [] | null | null | 18 | HOUR | To a stirred solution of 110 g (0.2 mole) of 4-triflylbenzyltriphenylphosphonium bromide in toluene is added dropwise 0.2 moles of n-BuLi at room temperature. After 2 hours a solution of 27.5 g (0.1 mole) of 4[N-4-hydroxybutyl-N-butylamino]cinnamaldehyde in toluene is added dropwise to the mixture, and the reaction is ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Tertiary amine | Enamine.Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 18 | CCCCN(CCCCO)c1ccc(C=CC=O)cc1.O=S(=O)(c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1)C(F)(F)F>C1(=CC=CC=C1)C>CCCCN(CCCCO)C(=CC=Cc1ccccc1)c1ccc(S(=O)(=O)C(F)(F)F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-002d9f5f7d094a87a267a18d90638473 | OCCCCCCBr.c1ccc2c(c1)CCCN2>>OCCCCCCN1CCCc2ccccc21 | N1CCCC2=CC=CC=C12.BrCCCCCCO.C([O-])([O-])=O.[K+].[K+]>>OCCCCCCN1CCCC2=CC=CC=C12 | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1].[NH:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21 | OCCCCCCBr.c1ccc2c(c1)CCCN2 | OCCCCCCN1CCCc2ccccc21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 219d202b93cb5a235df7e6646f3b9409e60d3c325f1ec37d9b75eb0c3554d20f | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(c1)CCCN2 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | A stirred solution of 133.2 g (1 mole) of 1,2,3,4-tetrahydroquinoline, 181.1 g (1 mole) of 6-bromohexanol, and 138.2 g (1 mole) of potassium carbonate in toluene is heated at 80° C. for 3 hours. The solution is cooled to room temperature, and the solids are removed by filtration. The solvent is removed in vacuo, and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | HBr | C1(=CC=CC=C1)C | null | null | OCCCCCCBr.c1ccc2c(c1)CCCN2>C1(=CC=CC=C1)C>OCCCCCCN1CCCc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bf199b56f7eb4319ac3c695eb26223f8 | CC(=O)OC(C)=O.OCCCCCCN1CCCC2CC=CC=C21>>CC(=O)OCCCCCCN1CCCc2ccccc21 | OCCCCCCN1CCCC2CC=CC=C12.C(C)(=O)OC(C)=O.C(C)N(CC)CC>>C(C)(=O)OCCCCCCN1CCCC2=CC=CC=C12 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH:15]2[CH2:16][CH:17]=[CH:18][CH:19]=[C:20]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | CC(=O)OC(C)=O.OCCCCCCN1CCCC2CC=CC=C21 | CC(=O)OCCCCCCN1CCCc2ccccc21 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 71a761ab5a61f07a9fddedefd628ef697febf2d90d3066ee73430c34a3b09da3 | 222fe5df041850e8bab46bf3676deadbb615af526f2aae9d8f614b82fc5895d7 | c1ccc2c(c1)CCCN2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#7:5]1-[C:6]-[C:7]-[C:8]-[CH;D3;+0:9]2-[CH2;D2;+0:10]-[CH;D2;+0:11]=[CH;D2;+0:12]-[CH;D2;+0:13]=[C;H0;D3;+0:14]-1-2.[C:15]-[C:16]-[OH;D1;+0:17]>>[C:4]-[#7:5]1-[C:6]-[C:7]-[C:8]-[c;H0;D3;+0:9]2:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c;H0;D3;+0:1... | null | [] | null | null | 3 | HOUR | To a stirred solution of 233.4 g (1 mole) of N-hydroxyhexyltetrahydroquinoline and 153.1 g (1.5 moles) of acetic anhydride in dichloromethane are added 151.8 g (1.5 moles) of triethylamine and 8.5 g (1 mole %) of 4-N,N-dimethylaminopyridine, and the reaction is stirred at room temperature for 3 hours. The product solut... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Anhydride.Primary alcohol.Conjugated diene | Ester | C1=CCC2CCC[NH]C2=C1 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | HO- | ClCCl | null | 3 | CC(=O)OC(C)=O.OCCCCCCN1CCCC2CC=CC=C21>ClCCl>CC(=O)OCCCCCCN1CCCc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f11fb9357654407f897a52ae5b73be5e | CC(=O)OCCCCCCN1CCCc2cc(C=O)ccc21>>O=CC=Cc1ccc2c(c1)CCCN2CCCCCCO | [Cl-].[Na+].C(C)(=O)OCCCCCCN1CCCC2=CC(=CC=C12)C=O.[Br-].O1C(OCC1)C[P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+]>>OCCCCCCN1CCCC2=CC(=CC=C12)C=CC=O | O=[CH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:2](=[O:1])[CH3:3]>>[O:1]=[CH:2][CH:3]=[CH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21] | CC(=O)OCCCCCCN1CCCc2cc(C=O)ccc21 | O=CC=Cc1ccc2c(c1)CCCN2CCCCCCO | null | null | CN(C=O)C.Cl.O | Miscellaneous | OtherReaction | 716d431b21b76dc7be86288acf6b079ba424a010e3c36e2883035373997c7f75 | 8312bfe1cc7896204f42ca6a876ec15c050ef293944cf9da7ac1091018dad53e | c1ccc2c(c1)CCCN2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:8](-[CH3;D1;+0:9])=[O;D1;H0:10]>>[C:5]-[C:6]-[OH;D1;+0:7].[O;D1;H0:10]=[CH;D2;+0:8]-[CH;D2;+0:9]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 90 | CELSIUS | 16 | HOUR | To a solution 30.3 g (0.1 mole) of N-acetoxyhexyl-1,2,3,4-tetrahydroquinoline-6-carboxaldehyde in dimethylformamide is added 7.4 g (0.2 mole) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide with magnetic stirring, and the mixture is heated at 90° C. Potassium t-butoxide (22.4 g, 0.2 mole) is ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Aldehyde.Primary alcohol | null | null | c1ccc2c(c1)CCC[NH]2 | Other | CN(C=O)C.Cl.O | 90 | 16 | CC(=O)OCCCCCCN1CCCc2cc(C=O)ccc21>CN(C=O)C.Cl.O>O=CC=Cc1ccc2c(c1)CCCN2CCCCCCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a8c9dc88ef314c6e9a5ee94f173add5d | Cc1ccc(C=O)cc1.Nc1ccccc1O>>Cc1ccc(-c2nc3ccccc3o2)cc1 | C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].[Pb+4].C1(=CC=C(C=C1)C=O)C.NC1=C(C=CC=C1)O.O>>CC1=CC=C(C=C1)C=1OC2=C(N1)C=CC=C2 | O=[CH:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:16][cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1 | Cc1ccc(C=O)cc1.Nc1ccccc1O | Cc1ccc(-c2nc3ccccc3o2)cc1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Benzoxazole formation from aldehyde | 3007b82893b25bcfc73c3208dc34ba7e37187776b8cbc5d23974d3df8a2d6e45 | 3b6ccbcd4ed8797e873d439bcb50326831cedfa183da57a93f69bf0c36077684 | c1ccc(-c2nc3ccccc3o2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | null | [] | null | null | 8 | HOUR | A solution of 12 g (0.1 mole) of 4-tolualdehyde and 10.9 g (0.1 mole) of 2-aminophenol in toluene is heated at reflux with azeotropic removal of water. After 20 hours at reflux, the reaction is cooled to room temperature, 44.3 g (0.1 mole) of lead tetraacetate is added, and the mixture is stirred at room temperature ov... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | null | 8 | Cc1ccc(C=O)cc1.Nc1ccccc1O>C1(=CC=CC=C1)C>Cc1ccc(-c2nc3ccccc3o2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5c4084f677714fefb5da04262b23b483 | Cc1ccc(-c2nc3ccccc3o2)cc1.O=C1CCC(=O)N1Br>>BrCc1ccc(-c2nc3ccccc3o2)cc1 | CC1=CC=C(C=C1)C=1OC2=C(N1)C=CC=C2.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrCC1=CC=C(C=C1)C=1OC2=C(N1)C=CC=C2 | [CH3:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17]1.O=C1CCC(=O)N1[Br:1]>>[Br:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17]1 | Cc1ccc(-c2nc3ccccc3o2)cc1.O=C1CCC(=O)N1Br | BrCc1ccc(-c2nc3ccccc3o2)cc1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2nc3ccccc3o2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A stirred solution of 20.9 g (0.1 mole) of 2-(4-methylphenyl)benzoxazole, 17.8 g (0.1 mole) of N-bromosuccinimide, and 0.4 g (0.2 mole %) of benzoyl peroxide in carbon tetrachloride is heated at reflux for 20 hours. After cooling to room temperature, the reaction is diluted by the addition of carbon tetrachloride, and ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(-c2nc3ccccc3o2)cc1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>BrCc1ccc(-c2nc3ccccc3o2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c3e99be3835445b2abbdee8d3ce15e26 | BrCc1ccc(-c2nc3ccccc3o2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Cc1ccc(-c2nc3ccccc3o2)cc1[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | BrCC1=CC=C(C=C1)C=1OC2=C(N1)C=CC=C2.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:1]([c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[o:14]2)[cH:15][cH:16]1)[Br:36].[P:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][... | BrCc1ccc(-c2nc3ccccc3o2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | Cc1ccc(-c2nc3ccccc3o2)cc1[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | null | C=1(C(=CC=CC1)C)C | Miscellaneous | OtherReaction | 580dbda2d71c1ade592946b82319659b10473e14402a8d60005effee81e40ce7 | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccc([P+](c2ccccc2)(c2ccccc2)c2cccc(-c3nc4ccccc4o3)c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7].[c:8]:[c:9](-[P;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c:14](:[c:15]):[c:16]):[c:17]>>[Br-;H0;D0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[P+;H0;D4:10](-[c:9](:[c:8]):[c:17])(-[c:11](:[c:12]):[c:13])-[c:14](:[c:15]):[c:16]):[c:6]:[c:7] | null | [] | null | null | null | null | A stirred solution of 28.8 g (0.1 mole) of 2-(4-bromomethylphenyl)benzoxazole and 28.8 g (0.1 mole) of triphenylphosphine in xylene is heated at reflux for 19 hours. The product is then isolated by filtration, washed with additional portions of xylene, and dried.
Conditions: See reaction.notes.procedure_details.
Workup... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ocnc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C=1(C(=CC=CC1)C)C | null | null | BrCc1ccc(-c2nc3ccccc3o2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C=1(C(=CC=CC1)C)C>Cc1ccc(-c2nc3ccccc3o2)cc1[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-56e0c8bc731e4aa9a568d920148f452a | Cc1ccc(-c2nc3ccccc3o2)cc1[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=CC=Cc1ccc2c(c1)CCCN2CCCCCCO>>OCCCCCCN1CCCc2cc(C=CC=Cc3ccc(-c4nc5ccccc5o4)cc3)ccc21 | O.[Li]CCCC.[Br-].O1C(=NC2=C1C=CC=C2)C2=CC(=C(C=C2)C)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.OCCCCCCN1CCCC2=CC(=CC=C12)C=CC=O>>OCCCCCCN1CCCC2=CC(=CC=C12)C=CC=CC1=CC=C(C=C1)C=1OC2=C(N1)C=CC=C2 | c1ccc([P+](c2ccccc2)(c2ccccc2)[c:33]2[c:19]([CH3:18])[cH:20][cH:21][c:22](-[c:23]3[n:24][c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]4[o:31]3)[cH:32]2)cc1.O=[CH:17][CH:16]=[CH:15][c:14]1[cH:13][c:12]2[c:36]([cH:35][cH:34]1)[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[CH2:9][CH2:10][CH2:11]2>>[OH:1][CH2:2][CH2:3]... | Cc1ccc(-c2nc3ccccc3o2)cc1[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=CC=Cc1ccc2c(c1)CCCN2CCCCCCO | OCCCCCCN1CCCc2cc(C=CC=Cc3ccc(-c4nc5ccccc5o4)cc3)ccc21 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 543566f4a6674a0bb62a9939a29cc850ad54f05e50d928975c9c5f4e9fb14baf | d70fa5718646c1ca7d5c68acab5b524370b238501cb432d711539d0f01ee6d2b | C(C=Cc1ccc2c(c1)CCCN2)=Cc1ccc(-c2nc3ccccc3o2)cc1 | O=[CH;D2;+0:1]-[C:2]=[C:3]-[c:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]:[c:10]>>[c:4]-[C:3]=[C:2]-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10] | null | [] | null | null | 18 | HOUR | To a stirred mixture of 110 g (0.2 mole) of 4-(benzoxazol-2-yl)tolyltriphenylphosphonium bromide in toluene is added dropwise 0.2 mole of n-BuLi at room temperature. After 2 hours a solution of 28.7 g (0.1 mole) of 3-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)acrolein in toluene is added dropwise to the mixture, a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Conjugated diene | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccc2ocnc2c1 | HO- | C1(=CC=CC=C1)C | null | 18 | Cc1ccc(-c2nc3ccccc3o2)cc1[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=CC=Cc1ccc2c(c1)CCCN2CCCCCCO>C1(=CC=CC=C1)C>OCCCCCCN1CCCc2cc(C=CC=Cc3ccc(-c4nc5ccccc5o4)cc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ed7c34e35eb445bc9fee78139710e092 | CC(C)(C)OC(=O)NC1C=NC=CS1.Nc1cccnc1>>Nc1cnccc1S | NC=1C=NC=CC1.[Cl-].[NH4+].C(C)(C)(C)OC(=O)NC1C=NC=CS1.Cl.NC=1C=NC=CC1.[S].C(C)(C)(C)OC(=O)OC(=O)OC(C)(C)C.C(CCC)[Li].NC1=NC=CC=C1>>Cl.NC=1C=NC=CC1S | CC(C)(C)OC(=O)N[CH:8]1[CH:7]=NC=C[S:9]1.c1c[cH:6][n:5][cH:4][c:3]1[NH2:2]>>[NH2:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[SH:9] | CC(C)(C)OC(=O)NC1C=NC=CS1.Nc1cccnc1 | Nc1cnccc1S | null | null | C(C)(=O)O.O1CCCC1 | Miscellaneous | OtherReaction | 4e53348320e93bccd881d297828ae2b10fd6c1a6b366daeec84e9b9206498efd | bd2e00fab2599223209d95fda741085272d9281a066aab16d41f2878f6c425f2 | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-N-[CH;D3;+0:1]1-[CH;D2;+0:2]=N-C=C-[S;H0;D2;+0:3]-1.[N;D1;H2:4]-[c;H0;D3;+0:5]1:[c:6]:[#7;a:7]:[cH;D2;+0:8]:c:c:1>>[N;D1;H2:4]-[c;H0;D3;+0:5]1:[c:6]:[#7;a:7]:[cH;D2;+0:8]:[cH;D2;+0:2]:[c;H0;D3;+0:1]:1-[SH;D1;+0:3] | null | [] | null | null | null | null | In Scheme (3), 3-aminopyridine is acylated with di-t-butyldicarbonate to introduce the t-butoxycarbonyl (t-BOC) protecting group. (It will be appreciated that two other pyridinothiazolothio mercaptans may be prepared by known methodology using other amino pyridine isomers.) The t-BOC protected 3-aminopyridine is then t... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted imine.Monosulfide.Boc | Aromatic thiol | C1=CSCC=N1.c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | C(C)(=O)O.O1CCCC1 | null | null | CC(C)(C)OC(=O)NC1C=NC=CS1.Nc1cccnc1>C(C)(=O)O.O1CCCC1>Nc1cnccc1S |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cc2ccc9b22a849008c758e58842ddd19 | CC(C)(C)OC(=O)Nc1cnccc1S>>Nc1cnccc1S | C(C)(C)(C)OC(=O)NC=1C=NC=CC1S.Cl>>Cl.NC=1C=NC=CC1S | CC(C)(C)OC(=O)[NH:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[SH:9]>>[NH2:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[SH:9] | CC(C)(C)OC(=O)Nc1cnccc1S | Nc1cnccc1S | null | null | C(C)(=O)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 100 | [{"value": 100.0, "product": "Cl.NC=1C=NC=CC1S", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 13.78 g (0.06 mol) sample of 3-(t-butyloxycarbonyl)amino-4-mercapto pyridine was dissolved with acetic acid (250 mL) and added to an ice cold solution of ~3N HCl in acetic acid which had been made by bubbling HCl(g) through glacial acetic acid (100 mL). After about four hours the resulting solid was filtered, washed ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1 | HO- | C(C)(=O)O | null | null | CC(C)(C)OC(=O)Nc1cnccc1S>C(C)(=O)O>Nc1cnccc1S |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f8af3a28440c4b40b27400296150885d | O=[N+]([O-])c1cccnc1Cl.[N-]=C=S>>O=[N+]([O-])c1cccnc1N=C=S | ClC1=NC=CC=C1[N+](=O)[O-].[N-]=C=S.[K+]>>N(=C=S)C1=NC=CC=C1[N+](=O)[O-] | Cl[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][n:8]1.[N-:10]=[C:11]=[S:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[N:10]=[C:11]=[S:12] | O=[N+]([O-])c1cccnc1Cl.[N-]=C=S | O=[N+]([O-])c1cccnc1N=C=S | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 27647861574f183f1d13ed634cc9d1fa17a57d6f7f63bbfc9e771872c68742a9 | be6b4969b868b064acf38b0c49ccd15931f1d8d0783e14c59d28ff8ffeddba70 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[N-;H0;D1:7]=[C:8]=[S;D1;H0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D2;+0:7]=[C:8]=[S;D1;H0:9]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | A 10 g sample of 2-chloro-3-nitropyridine, an 8 g sample of potassium isothiocyanate, and 75 ml of acetic acid were combined and refluxed for 2 h. The reaction mixture was then cooled and poured into 400 ml of ice/H2O. The resulting solid was washed with water, redissolved in ethyl acetate and washed (4×) with water. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Isothiocyanate | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C(C)(=O)O | null | null | O=[N+]([O-])c1cccnc1Cl.[N-]=C=S>C(C)(=O)O>O=[N+]([O-])c1cccnc1N=C=S |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-79ee1b74b31a41bdac5b200a71352fcd | ClCCOCCOCCCl.NCc1ccccc1>>c1ccc(CNCCOCCOCCNCc2ccccc2)cc1 | C(C1=CC=CC=C1)N.ClCCOCCOCCCl>>C(C1=CC=CC=C1)NCCOCCOCCNCC1=CC=CC=C1 | Cl[CH2:1][CH2:2][O:12][CH2:11][CH2:3][O:9][CH2:8][CH2:7]Cl.[c:4]1([CH2:5][NH2:6])[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1 | ClCCOCCOCCCl.NCc1ccccc1 | c1ccc(CNCCOCCOCCNCc2ccccc2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b3892053c1eafd59ea3e581bb7123385d14c234c00bae7d2bac72faed5d9fb7e | 9ca3e54d8c2d9428f8929837b66b2f22c82679eae81ee5f0378e863125572ea4 | c1ccc(CNCCOCCOCCNCc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[C:7]-[CH2;D2;+0:8]-Cl.[NH2;D1;+0:9]-[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[c:13]:[c:14]:[c:15]:[cH;D2;+0:16]:1>>[C:17]-[C:18]-[O;H0;D2;+0:3]-[CH2;D2;+0:4]-[C:19]-[O;H0;D2;+0:6]-[C:7]-[CH2;D2;+0:8]-[NH;D2;+0:9]-[C:10]-[c;H0;D3;+0:1... | null | [] | null | null | null | null | J. Gatto, et al. in "4,13-Diaza-18-Crown-6 (1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane)," Organic Synthesis, Vol. 68, 1989, pp. 227-233, teach the preparation of the title compound by a three-step procedure that might be considered the standard preparation for these materials. First, benzylamine is reacted with 1,2-b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Ether.Primary amine | Ether.Ether.Secondary amine.Secondary amine | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | ClCCOCCOCCCl.NCc1ccccc1>>c1ccc(CNCCOCCOCCNCc2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5d6c2380db7048b1ba438d1bba8589f6 | BrC1CC1.CN1Cc2c(C=O)ncn2-c2ccncc2C1=O>>OC(C1=CNc2ccncc2C=N1)C1CC1 | O1CCCC1.C1(CC1)[Mg]Br.[Mg].C1(CC1)Br.O1CCCC1.O1CCCC1.CN1CC=2N(C3=C(C1=O)C=NC=C3)C=NC2C=O>>N1C=C(N=CC2=C1C=CN=C2)C(O)C2CC2 | Br[CH:14]1[CH2:15][CH2:16]1.C[N:13]1Cc2[c:3]([CH:2]=[O:1])n[cH:4][n:5]2-[c:6]2[cH:7][cH:8][n:9][cH:10][c:11]2[C:12]1=O>>[OH:1][CH:2]([C:3]1=[CH:4][NH:5][c:6]2[cH:7][cH:8][n:9][cH:10][c:11]2[CH:12]=[N:13]1)[CH:14]1[CH2:15][CH2:16]1 | BrC1CC1.CN1Cc2c(C=O)ncn2-c2ccncc2C1=O | OC(C1=CNc2ccncc2C=N1)C1CC1 | null | null | CN(P(=O)(N(C)C)N(C)C)C | Heteroatom Alkylation and Arylation | OtherReaction | 195c597aab917323d56570a8e26a88ebc9fc82bd44b596ae21b64111ec4616b8 | 36df40030e480a3681c84c70c6280636c63a4235eafcc1fa595964e12f7e847a | C1=NC(CC2CC2)=CNc2ccncc21 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-1.C-[N;H0;D3;+0:4]1-C-c2:[c;H0;D3;+0:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):n:[cH;D2;+0:8]:[n;H0;D3;+0:9]:2-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:2-[C;H0;D3;+0:16]-1=O>>[OH;D1;+0:7]-[CH;D3;+0:6](-[C;H0;D3;+0:5]1=[CH;D2;+0:8]-[NH;D2;+0:9]-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[#7;a:13]:[... | 5 | [{"value": 5.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of cyclopropyl magnesium bromide in dry tetrahydrofuran (prepared from 72 mg (3 mmole)) of magnesium and 362 mg (3 mmole) of cyclopropyl bromide in 4 ml of tetrahydrofuran was added at room temperature in one portion a suspension of 240 mg (1 mmole)of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo [1,5-a]-pyrido [... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Tertiary amide | Enamine.Substituted imine.Secondary alcohol | C1CC1.c1cc2c(cn1)C[NH]Cc1cncn12 | C1=CNc2ccncc2C=N1.C1CC1 | C1=CNc2ccncc2C=N1.C1CC1 | HBr | CN(P(=O)(N(C)C)N(C)C)C | null | 1 | BrC1CC1.CN1Cc2c(C=O)ncn2-c2ccncc2C1=O>CN(P(=O)(N(C)C)N(C)C)C>OC(C1=CNc2ccncc2C=N1)C1CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5669067be2dd44efab57c051c34b17f5 | NC(=O)c1cnn2c1NCC=C2c1cccc(C(F)(F)F)c1.S=C=S>>CSc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1 | FC(C=1C=C(C=CC1)C1=CCNC=2N1N=CC2C(=O)N)(F)F.CC(C)([O-])C.[K+].C(=S)=S>>CSC1=NC(C=2C=NN3C(=CCN1C32)C3=CC(=CC=C3)C(F)(F)F)=O | [NH2:4][C:5](=[O:6])[c:7]1[cH:8][n:9][n:10]2[c:11]1[NH:12][CH2:13][CH:14]=[C:15]2[c:16]1[cH:17][cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]1.S=[C:3]=[S:2]>>[CH3:1][S:2][c:3]1[n:4][c:5](=[O:6])[c:7]2[cH:8][n:9][n:10]3[c:11]2[n:12]1[CH2:13][CH:14]=[C:15]3[c:16]1[cH:17][cH:18][cH:19][c:20]([C:21]([F:22])([F:2... | NC(=O)c1cnn2c1NCC=C2c1cccc(C(F)(F)F)c1.S=C=S | CSc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 159a87f29c09ab117d87c33456fa0aa717d0c1b5ab1dc6117e9039650144895f | 52ca609e0ddb9fbbdbd11d400361a38aa8d2c2913a103a89bb982ae5f37d98a5 | O=c1ncn2c3c1cnn3C(c1ccccc1)=CC2 | S=[C;H0;D2;+0:1]=[S;H0;D1;+0:2].[NH2;D1;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[#7;a:9]2:[c:10]:1-[NH;D2;+0:11]-[C:12]-[C:13]=[C:14]-2-[c:15]>>[C;D1;H3:16]-[S;H0;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](=[O;D1;H0:5]):[c:6]2:[c:7]:[#7;a:8]:[#7;a:9]3:[c:10]:2:[n;H0;D3;+0:11]:1-[C:12]-[C:13... | 90.5 | [{"value": 90.0, "product": "CSC1=NC(C=2C=NN3C(=CCN1C32)C3=CC(=CC=C3)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "CSC1=NC(C=2C=NN3C(=CCN1C32)C3=CC(=CC=C3)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -6.2 | CELSIUS | 45 | MINUTE | A solution of 3.18 kg of 4,5-dihydro-7-[3-(trifluoromethyl)-phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide in 30 L of tetrahydrofuran is cooled to 2.8° C. under nitrogen and stirred while 1370 g of potassium tert-butoxide is added portionwise over 25 minutes while maintaining a temperature less than 4° C. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amine | Monosulfide | C1=Cn2nccc2NC1 | C1=CCn2cncc3cnn1c32 | C1=CCn2cncc3cnn1c32.c1ccccc1 | null | O1CCCC1 | -6.2 | 0.75 | NC(=O)c1cnn2c1NCC=C2c1cccc(C(F)(F)F)c1.S=C=S>O1CCCC1>CSc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eadcefa2a05d42d58610fc3268716e7a | CC(C)N.CSc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1>>CC(C)Nc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1 | CSC1=NC(C=2C=NN3C(=CCN1C32)C3=CC(=CC=C3)C(F)(F)F)=O.C(C)(C)N.C(C)O.C(C)O>>CC(C)NC1=NC(C=2C=NN3C(=CCN1C32)C3=CC(=CC=C3)C(F)(F)F)=O | [CH3:1][CH:2]([CH3:3])[NH2:4].CS[c:5]1[n:6][c:7](=[O:8])[c:9]2[cH:10][n:11][n:12]3[c:13]2[n:14]1[CH2:15][CH:16]=[C:17]3[c:18]1[cH:19][cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[n:6][c:7](=[O:8])[c:9]2[cH:10][n:11][n:12]3[c:13]2[n:14]1[CH2:15][CH:16]=[C:17]3[c:18]1[cH:1... | CC(C)N.CSc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1 | CC(C)Nc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | ba5bcb07336db7f2300c2868569a4481815a759d4c806fe39f12f9bc7feed0b0 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1ncn2c3c1cnn3C(c1ccccc1)=CC2 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[#7;a:7]3:[c:8]:2:[#7;a:9]:1-[C:10]-[C:11]=[C:12]-3.[C;D1;H3:13]-[C:14](-[C;D1;H3:15])-[NH2;D1;+0:16]>>[C;D1;H3:13]-[C:14](-[C;D1;H3:15])-[NH;D2;+0:16]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[#7;a:7]3:[c:8]:2:[#7;a:9]:1-[C:10]-[C:11]=[C:12]-3 | 62.3 | [{"value": 62.3, "product": "CC(C)NC1=NC(C=2C=NN3C(=CCN1C32)C3=CC(=CC=C3)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "CC(C)NC1=NC(C=2C=NN3C(=CCN1C32)C3=CC(=CC=C3)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of 5.0 g of 5-(methylthio)-8-[3-(trifluoromethyl)phenyl]-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one in 35 ml of acetic acid is added 2.64 g of isopropylamine. The reaction mixture is heated on a steambath for 18 hours. The resulting solution is cooled to room temperature and 17 ml of ethanol added. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | C1=CCn2cncc3cnn1c32 | C1=CCn2cncc3cnn1c32 | C1=CCn2cncc3cnn1c32.c1ccccc1 | Other | C(C)(=O)O | null | 0.5 | CC(C)N.CSc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1>C(C)(=O)O>CC(C)Nc1nc(=O)c2cnn3c2n1CC=C3c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-695590d38ba04361a966067c6963981f | N#Cc1ccccc1N.O=C1CCCC(=O)C1>>N#Cc1ccccc1NC1=CC(=O)CCC1 | NC1=C(C#N)C=CC=C1.C1(CC(CCC1)=O)=O>>O=C1C=C(CCC1)NC1=C(C#N)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].O=[C:10]1[CH2:11][C:12](=[O:13])[CH2:14][CH2:15][CH2:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][C:10]1=[CH:11][C:12](=[O:13])[CH2:14][CH2:15][CH2:16]1 | N#Cc1ccccc1N.O=C1CCCC(=O)C1 | N#Cc1ccccc1NC1=CC(=O)CCC1 | null | O.CC1=CC=C(C=C1)S(=O)(=O)O | O | Heteroatom Alkylation and Arylation | OtherReaction | b5fad61eda15276f50ae7bc35245e587435b6eeee71b12fe6b584707eb92cb10 | 9b8ae7e5b30e191314c6441607ab55dc332b8bb8a66eba32f5a7b73c6f6f2034 | O=C1C=C(Nc2ccccc2)CCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[C:5]1-[C:4]-[C:3]-[C:2]-[C;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])=[CH;D2;+0:7]-1 | 93 | [{"value": 93.0, "product": "O=C1C=C(CCC1)NC1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "O=C1C=C(CCC1)NC1=C(C#N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-aminobenzonitrile (120 g) and 1,3-cyclohexandione (120 g) in water (400 ml) was heated to 40° and 4-methylbenzenesulfonic acid monohydrate (6.2 g) was added, with stirring. The mixture was stirred at 40° for 1 hr. The mixture was filtered, and the filter cake was washed with water to provide 200 g (93%) ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | Enamine | C1CCCCC1 | C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | HO- | O.CC1=CC=C(C=C1)S(=O)(=O)O.O | null | null | N#Cc1ccccc1N.O=C1CCCC(=O)C1>O.CC1=CC=C(C=C1)S(=O)(=O)O.O>N#Cc1ccccc1NC1=CC(=O)CCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ef26d013c4cc405e8068592ad63dfa26 | N#Cc1ccccc1N.O=C1CCCCC1>>Nc1c2c(nc3ccccc13)CCCC2.O | Cl.NC1=C(C#N)C=CC=C1.C1(CCCCC1)=O.Cl>>O.NC=1C2=CC=CC=C2N=C2CCCCC12 | [N:1]#[C:2][c:11]1[c:6]([NH2:5])[cH:7][cH:8][cH:9][cH:10]1.[C:3]1(=[O:16])[CH2:4][CH2:12][CH2:13][CH2:14][CH2:15]1>>[NH2:1][c:2]1[c:3]2[c:4]([n:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]13)[CH2:12][CH2:13][CH2:14][CH2:15]2.[OH2:16] | N#Cc1ccccc1N.O=C1CCCCC1 | Nc1c2c(nc3ccccc13)CCCC2.O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2dd1f9e0e8eafd34226d7996df8c63bc3e7f04d2db44935e4c1d66db8009fc46 | cba055f16bb6d8902fe3b7ee13bd8e7822896a26eeb51828f22dbf1978e995c7 | c1ccc2nc3c(cc2c1)CCCC3 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].[O;H0;D1;+0:8]=[C;H0;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-1>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3](:[c:4]):[c:5](:[c:7]):[n;H0;D2;+0:6]:[c;H0;D3;+0:14]2:[c;H0;D3;+0:9]:1-[C:10]-[C:11]-[C:12]-[C:13]-2.[OH2;D0;+0:8] | 67 | [{"value": 67.0, "product": "O.NC=1C2=CC=CC=C2N=C2CCCCC12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-aminobenzonitrile (120 g), cyclohexanone (115.8 ml), conc hydrochloric acid (9.2 ml), and cuprous chloride (1.21 g) was heated under reflux for 3 days, with stirring. At the end of each 24 hr period, additional cuprous chloride (1.21 g) was added. At the end of the 3rd day, additional conc hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile.Primary amine | Primary amine | c1ccccc1.C1CCCCC1 | c1ccc2nc3c(cc2c1)CCCC3 | c1ccc2nc3c(cc2c1)CCCC3 | null | null | null | null | N#Cc1ccccc1N.O=C1CCCCC1>>Nc1c2c(nc3ccccc13)CCCC2.O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-63b9b2d355cb436f8db69da91037fe95 | CN(C)C=O.COc1cccc(Cl)n1>>COc1nc(Cl)ccc1C=O | C(C)(=O)O.CN(C=O)C.C(C)(C)(C)[Li].ClC1=CC=CC(=N1)OC>>ClC1=CC=C(C(=N1)OC)C=O | CN(C)[CH:10]=[O:11].[CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][cH:8][cH:9]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[CH:10]=[O:11] | CN(C)C=O.COc1cccc(Cl)n1 | COc1nc(Cl)ccc1C=O | null | null | CCOCC.C1CCOC1 | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 75 | [{"value": 75.0, "product": "ClC1=CC=C(C(=N1)OC)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "ClC1=CC=C(C(=N1)OC)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | To a solution of tert-butyllithium (1.7 M in pentane, 48.5 mL, 83.0 mmol) in 150 mL of THF at -78° C. was added 6-chloro-2-methoxypyridine (8.94 mL, 75.0 mmol) over 5 min. The reaction mixture was stirred at -78° C. for 1 h, then dimethylformamide (7.55 mL, 97 mmol) was added and the mixture was stirred at this tempera... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | CCOCC.C1CCOC1 | -78 | 1 | CN(C)C=O.COc1cccc(Cl)n1>CCOCC.C1CCOC1>COc1nc(Cl)ccc1C=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7c63c4175fe54b74b2ffdf5c102f7d48 | COc1nc(Cl)ccc1C=O.II>>COc1nc(Cl)cc(I)c1C=O | II.ClC1=CC=C(C(=N1)OC)C=O.[Li]CCCC.CN(CCNC)C.[Li]CCCC>>ClC1=CC(=C(C(=N1)OC)C=O)I | [CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][cH:8][c:10]1[CH:11]=[O:12].I[I:9]>>[CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][c:8]([I:9])[c:10]1[CH:11]=[O:12] | COc1nc(Cl)ccc1C=O.II | COc1nc(Cl)cc(I)c1C=O | null | null | COCCOC | Functional Group Interconversion | OtherReaction | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | I-[I;H0;D1;+0:1].[#8:2]-[c:3]1:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[cH;D2;+0:8]:[c:9]:1-[C:10]=[O;D1;H0:11]>>[#8:2]-[c:3]1:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[c;H0;D3;+0:8](-[I;H0;D1;+0:1]):[c:9]:1-[C:10]=[O;D1;H0:11] | 51.3 | [{"value": 51.3, "product": "ClC1=CC(=C(C(=N1)OC)C=O)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -23 | CELSIUS | 20 | MINUTE | To a solution of N,N,N'-trimethylethylenediamine (2.46 mL, 19.23 mmol) in 15 mL of 1,2-dimethoxyethane at -23° C. was added n-BuLi (9.22 mL, 19.23 mmol), and the solution was stirred at -23° C. for 20 min. The mixture was transferred using a double-tipped needle to a solution of 6-chloro-2-methoxy-3-pyridinecarboxaldeh... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | COCCOC | -23 | 0.333333 | COc1nc(Cl)ccc1C=O.II>COCCOC>COc1nc(Cl)cc(I)c1C=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-36aa6e8ebe7944bf8139e096653ebd8c | CO.COc1nc(Cl)cc(I)c1C=O>>COCc1c(I)cc(Cl)nc1OC | FC(C(=O)O)(F)F.ClC1=CC(=C(C(=N1)OC)C=O)I.C(C)[SiH](CC)CC.CO.C(=O)(O)[O-].[Na+]>>ClC1=NC(=C(C(=C1)I)COC)OC | O[CH3:1].[O:2]=[CH:3][c:4]1[c:5]([I:6])[cH:7][c:8]([Cl:9])[n:10][c:11]1[O:12][CH3:13]>>[CH3:1][O:2][CH2:3][c:4]1[c:5]([I:6])[cH:7][c:8]([Cl:9])[n:10][c:11]1[O:12][CH3:13] | CO.COc1nc(Cl)cc(I)c1C=O | COCc1c(I)cc(Cl)nc1OC | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 1d76918cc19966c7516bfe9a97a96abd1d20ff1b6b551b7a2a7721be5b12e885 | a9e58bdb270b8602210135fa12a97050bf42474a87c9f2c3a2f396b5330373a5 | c1ccncc1 | O-[CH3;D1;+0:1].[#8:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[CH;D2;+0:7]=[O;H0;D1;+0:8]):[c:9]>>[#8:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[CH3;D1;+0:1]):[c:9] | 93 | [{"value": 93.0, "product": "ClC1=NC(=C(C(=C1)I)COC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "ClC1=NC(=C(C(=C1)I)COC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 14 | HOUR | To a mixture of 6-chloro-4-iodo-2-methoxy-3-pyridinecarboxaldehyde (1.07 g, 3.60 mmol), triethylsilane (0.86 mL, 5.40 mmol) and methanol (0.43 mL, 10.6 mmol) at 0° C. was added trifluoroacetic acid (2.2 mL, 28.6 mmol), and the resulting solution was stirred at 25° C. for 14 h. After dilution with ether (30 mL), saturat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Methanol | Ether | null | null | c1ccncc1 | Other | CCOCC | 25 | 14 | CO.COc1nc(Cl)cc(I)c1C=O>CCOCC>COCc1c(I)cc(Cl)nc1OC |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.