dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c62f99d0fed4032b2e1262e33a10198 | CC(C)(C)c1ccc(S(N)(=O)=O)cc1.Clc1cc(Cl)ncn1>>CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(Cl)ncn2)cc1 | ClC1=NC=NC(=C1)Cl.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)N.[H-].[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH2:12])[cH:20][cH:21]1.Cl[c:13]1[cH:14][c:15]([Cl:16])[n:17][cH:18][n:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]2[cH:14][c:15]([Cl:16])[n:17][cH:18][n:19]2)[cH:20][cH:21]1 | CC(C)(C)c1ccc(S(N)(=O)=O)cc1.Clc1cc(Cl)ncn1 | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(Cl)ncn2)cc1 | null | null | CN(C=O)C.Cl.O | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(Nc1ccncn1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1.[NH2;D1;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]>>[Cl;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]):[c:7]:1 | 69.4 | [{"value": 69.4, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4,6-dichloropyrimidine (1.33 g) and 4-tert-butylbenzenesulfonamide (1.96 g) in dimethylformamide (20 ml) is added sodium hydride (60% dispersion-type, 714 mg). The mixture is stirred at room temperature for two hours, and the reaction solution is diluted with 10% hydrochloric acid and water. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | CN(C=O)C.Cl.O | null | 2 | CC(C)(C)c1ccc(S(N)(=O)=O)cc1.Clc1cc(Cl)ncn1>CN(C=O)C.Cl.O>CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(Cl)ncn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a389d63ceeae4459863ae17f76d2bba8 | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(Cl)ncn2)cc1.OCCO>>CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(OCCO)ncn2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)Cl.[H-].[Na+].C(CO)O.Cl>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)OCCO | Cl[c:15]1[cH:14][c:13]([NH:12][S:9]([c:8]2[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:24][cH:23]2)(=[O:10])=[O:11])[n:22][cH:21][n:20]1.[OH:16][CH2:17][CH2:18][OH:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]2[cH:14][c:15]([O:16][CH2:17][CH2:18][OH:19])[n:20][c... | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(Cl)ncn2)cc1.OCCO | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(OCCO)ncn2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccncn1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[C:8]-[C:9]-[OH;D1;+0:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[C:9]-[C:8]):[c:7]:1 | null | [] | 60 | CELSIUS | 20 | HOUR | To ethylene glycol (20 ml) is added sodium hydride (60% dispersion-type, 1.03 g), and thereto is added 4-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide (1.66 g). The mixture is stirred at 60° C. for 20 hours. After cooling, the mixture is acidified with 10% hydrochloric acid, and extracted with ethyl acetate. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | 60 | 20 | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(Cl)ncn2)cc1.OCCO>>CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(OCCO)ncn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-da9e15d8493a44cfbbae58022cf084ac | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(OCCO)ncn2)cc1.O=C1CCC(=O)N1Br>>CC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCO)c2Br)cc1 | S(=O)(O)[O-].[Na+].C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1)OCCO.BrN1C(CCC1=O)=O>>BrC=1C(=NC=NC1OCCO)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]2[n:14][cH:15][n:16][c:17]([O:18][CH2:19][CH2:20][OH:21])[cH:22]2)[cH:24][cH:25]1.O=C1CCC(=O)N1[Br:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]2[n:14][cH:15][n:16][c:17]([O:18][CH... | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(OCCO)ncn2)cc1.O=C1CCC(=O)N1Br | CC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCO)c2Br)cc1 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | ce862b99084d022122186a4bb29e2cc909823387b5fab03ae9d40a04a60bbc3f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=S(=O)(Nc1ccncn1)c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[#8:8]):[cH;D2;+0:9]:1>>[#7:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[#8:8]):[c;H0;D3;+0:9]:1-[Br;H0;D1;+0:1] | 65.7 | [{"value": 65.7, "product": "BrC=1C(=NC=NC1OCCO)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamide (210 mg) in dimethylformamide (4 ml) is added N-bromosuccinimide (116 mg), and the mixture is stirred at room temperature for one hour. The mixture is treated with aqueous sodium hydrogen sulfite solution, and extracted with ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cncnc1.C1CCNC1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | CN(C=O)C | null | 1 | CC(C)(C)c1ccc(S(=O)(=O)Nc2cc(OCCO)ncn2)cc1.O=C1CCC(=O)N1Br>CN(C=O)C>CC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCO)c2Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b4685538e6b8446fb9eabb0b5495e015 | CC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCO)c2Br)cc1.CSc1cnc(Cl)nc1>>CSc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Br)nc1 | BrC=1C(=NC=NC1OCCO)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C.[H-].[Na+].Cl.[Cl-].[NH4+].ClC1=NC=C(C=N1)SC>>BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C | [OH:7][CH2:8][CH2:9][O:10][c:11]1[n:12][cH:13][n:14][c:15]([NH:16][S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]2)[c:30]1[Br:31].Cl[c:6]1[n:5][cH:4][c:3]([S:2][CH3:1])[cH:33][n:32]1>>[CH3:1][S:2][c:3]1[cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][n... | CC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCO)c2Br)cc1.CSc1cnc(Cl)nc1 | CSc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Br)nc1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1cc(OCCOc2ncccn2)ncn1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 83.6 | [{"value": 83.6, "product": "BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (3.10 g) in dimethylacetamide (30 ml) is added sodium hydride (60% dispersion-type, 720 mg), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added 2-chloro-5-methylthiopyrimidine (1.51 g), and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cncnc1.c1ccccc1 | HCl | CC(=O)N(C)C | null | 0.5 | CC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCO)c2Br)cc1.CSc1cnc(Cl)nc1>CC(=O)N(C)C>CSc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Br)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f570953042144533ac7122491f64e455 | Clc1cc(Cl)ncn1.OCCO>>OCCOc1cc(Cl)ncn1 | ClC1=NC=NC(=C1)Cl.C(CO)O.[H-].[Na+]>>ClC1=CC(=NC=N1)OCCO | Cl[c:5]1[cH:6][c:7]([Cl:8])[n:9][cH:10][n:11]1.[OH:1][CH2:2][CH2:3][OH:4]>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7]([Cl:8])[n:9][cH:10][n:11]1 | Clc1cc(Cl)ncn1.OCCO | OCCOc1cc(Cl)ncn1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1.[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1 | null | [] | null | null | 2 | HOUR | To a mixture of 4,6-dichloropyrimidine (5.0 g), ethylene glycol (100 ml) and tetrahydrofuran (100 ml)is added sodium hydride (60% dispersion-type, 1.34 g) under ice-cooling. The mixture is stirred at the same temperature for two hours, and evaporated to remove the solvent. The residue is extracted with ethyl acetate, a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | O1CCCC1 | null | 2 | Clc1cc(Cl)ncn1.OCCO>O1CCCC1>OCCOc1cc(Cl)ncn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fca1a49f76c14ce8bae2a93158f456ab | OCCOc1cc(Cl)ncn1.[N-]=[N+]=[N-]>>[N-]=[N+]=Nc1cc(OCCO)ncn1 | O.ClC1=CC(=NC=N1)OCCO.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])C1=CC(=NC=N1)OCCO | Cl[c:4]1[cH:5][c:6]([O:7][CH2:8][CH2:9][OH:10])[n:11][cH:12][n:13]1.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][c:4]1[cH:5][c:6]([O:7][CH2:8][CH2:9][OH:10])[n:11][cH:12][n:13]1 | OCCOc1cc(Cl)ncn1.[N-]=[N+]=[N-] | [N-]=[N+]=Nc1cc(OCCO)ncn1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 48465a5e07f474e518aa4021a9b68659838d8b370bfeed26501047d7c300e8e7 | df579c5e1cf1cc42720dad6dd16c8deec88e9170508fbd47357453cfc40bcb7a | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1.[N-;H0;D1:8]=[#7;+:9]=[N;-;D1;H0:10]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D2;+0:8]=[#7;+:9]=[N;-;D1;H0:10]):[c:7]:1 | 28.9 | [{"value": 28.9, "product": "N(=[N+]=[N-])C1=CC(=NC=N1)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 20 | HOUR | To a solution of 2-(6-chloropyrimidin-4-yloxy)ethanol (5.61 g) in dimethylformamide (60 ml) is added sodium azide (4.18 g), and the mixture is stirred at 70° C. for 20 hours. After cooling, the reaction solution is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is dried, and evaporated to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Azide | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | CN(C=O)C | 70 | 20 | OCCOc1cc(Cl)ncn1.[N-]=[N+]=[N-]>CN(C=O)C>[N-]=[N+]=Nc1cc(OCCO)ncn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa1f51d360144913905861053111ec80 | [N-]=[N+]=Nc1cc(OCCO)ncn1>>Nc1cc(OCCO)ncn1 | N(=[N+]=[N-])C1=CC(=NC=N1)OCCO>>NC1=CC(=NC=N1)OCCO | [N-]=[N+]=[N:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][OH:8])[n:9][cH:10][n:11]1>>[NH2:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][OH:8])[n:9][cH:10][n:11]1 | [N-]=[N+]=Nc1cc(OCCO)ncn1 | Nc1cc(OCCO)ncn1 | null | [C].[Pd] | C(C)O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1cncnc1 | [N-]=[N+]=[N;H0;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1>>[NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 79 | [{"value": 79.0, "product": "NC1=CC(=NC=N1)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 2-(6-azidopyrimidin-4-yloxy)ethanol (1.64 g), 10% palladium-carbon (0.25 g) and ethanol (20 ml) is subjected to catalytic hydrogenation at room temperature for one hour under hydrogen atmosphere (1 atm). The catalyst is removed by filtration, and the filtrate is concentrated. The residue is recrystallized ... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1cncnc1 | Other | [C].[Pd].C(C)O | null | 1 | [N-]=[N+]=Nc1cc(OCCO)ncn1>[C].[Pd].C(C)O>Nc1cc(OCCO)ncn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f3278729434431a9be2a0b527dc71ea | BrBr.Nc1cc(OCCO)ncn1>>Nc1ncnc(OCCO)c1Br | NC1=CC(=NC=N1)OCCO.BrBr>>NC1=C(C(=NC=N1)OCCO)Br | Br[Br:12].[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][OH:10])[cH:11]1>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][OH:10])[c:11]1[Br:12] | BrBr.Nc1cc(OCCO)ncn1 | Nc1ncnc(OCCO)c1Br | null | null | CO | Functional Group Interconversion | Bromination | b0bb6940bdaa4f483f95617a9ee5e6563c160ea710db3fde10ee056459a3fce1 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cncnc1 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[N;D1;H2:8]):[cH;D2;+0:9]:1>>[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[N;D1;H2:8]):[c;H0;D3;+0:9]:1-[Br;H0;D1;+0:1] | 104.7 | [{"value": 104.7, "product": "NC1=C(C(=NC=N1)OCCO)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 2-(6-aminopyrimidin-4-yloxy)ethanol (400 mg) in methanol (4 ml) is added dropwise a solution of bromine (437 mg) in methanol (2 ml). The mixture is evaporated to remove the solvent, and the residue is dissolved in ethyl acetate. The mixture is treated with saturated aqueous sodium hydrogen carbonate ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | CO | null | null | BrBr.Nc1cc(OCCO)ncn1>CO>Nc1ncnc(OCCO)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4bd91debc1224985b59b17dd05823067 | CSc1cnc(Cl)nc1.Nc1ncnc(OCCO)c1Br>>CSc1cnc(OCCOc2ncnc(N)c2Br)nc1 | ClC1=NC=C(C=N1)SC.NC1=C(C(=NC=N1)OCCO)Br.[H-].[Na+]>>BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)N | Cl[c:6]1[n:5][cH:4][c:3]([S:2][CH3:1])[cH:20][n:19]1.[OH:7][CH2:8][CH2:9][O:10][c:11]1[n:12][cH:13][n:14][c:15]([NH2:16])[c:17]1[Br:18]>>[CH3:1][S:2][c:3]1[cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][n:14][c:15]([NH2:16])[c:17]2[Br:18])[n:19][cH:20]1 | CSc1cnc(Cl)nc1.Nc1ncnc(OCCO)c1Br | CSc1cnc(OCCOc2ncnc(N)c2Br)nc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cnc(OCCOc2ccncn2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 53.6 | [{"value": 53.6, "product": "BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 2-(6-amino-5-bromopyrimidin-4-yloxy)ethanol (611 mg) in dimethylformamide (20 ml) is added sodium hydride (60% dispersion-type, 125 mg), and the mixture is stirred for 20 minutes. To the mixture is added 2-chloro-5-methylthiopyrimidine (461 mg), and the mixture is stirred at room temperature for three ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cncnc1 | HCl | CN(C=O)C | null | 0.333333 | CSc1cnc(Cl)nc1.Nc1ncnc(OCCO)c1Br>CN(C=O)C>CSc1cnc(OCCOc2ncnc(N)c2Br)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad49e82362d34ffea232b146b2698729 | CC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.CSc1cnc(OCCOc2ncnc(N)c2Br)nc1>>CSc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Br)nc1 | [Cl-].[NH4+].C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)Cl.BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)N.[H-].[Na+]>>BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C | Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1.[CH3:1][S:2][c:3]1[cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][n:14][c:15]([NH2:16])[c:30]2[Br:31])[n:32][cH:33]1>>[CH3:1][S:2][c:3]1[cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][n... | CC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.CSc1cnc(OCCOc2ncnc(N)c2Br)nc1 | CSc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Br)nc1 | null | null | N1=CC=CC=C1.O.O1CCCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1cc(OCCOc2ncccn2)ncn1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1)-[c:4](:[c:5]):[c:6] | 85.5 | [{"value": 85.5, "product": "BrC=1C(=NC=NC1OCCOC1=NC=C(C=N1)SC)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine (102 mg) in tetrahydrofuran (2 ml) is added sodium hydride (60% dispersion-type, 34 mg), and thereto is added 4-tert-butylbenzenesulfonyl chloride (198 mg). The mixture is stirred at room temperature for 20 minutes, and thereto are a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cncnc1.c1cncnc1.c1ccccc1 | HCl | N1=CC=CC=C1.O.O1CCCC1 | null | 0.333333 | CC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.CSc1cnc(OCCOc2ncnc(N)c2Br)nc1>N1=CC=CC=C1.O.O1CCCC1>CSc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Br)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fcdab10bc84144e59957a7d86566aed7 | CCCC(=N)N.CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1>>CCCc1nc(O)c(-c2ccc(C)cc2)c(O)n1 | C(C)OC(C(C(=O)OCC)C1=CC=C(C=C1)C)=O.Cl.C(CCC)(=N)N.C[O-].[Na+]>>CC1=CC=C(C=C1)C=1C(=NC(=NC1O)CCC)O | [CH3:1][CH2:2][CH2:3][C:4](=[NH:5])[NH2:18].CCO[C:6](=[O:7])[CH:8]([c:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]1)[C:16](OCC)=[O:17]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([OH:7])[c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]2)[c:16]([OH:17])[n:18]1 | CCCC(=N)N.CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1 | CCCc1nc(O)c(-c2ccc(C)cc2)c(O)n1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2cncnc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[C:11]-[C:12]-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[NH;D1;+0:15]>>[C:11]-[C:12]-[c;H0;D3;+0:13]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[c;H0;D3;+0:3](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:... | 56.1 | [{"value": 56.1, "product": "CC1=CC=C(C=C1)C=1C(=NC(=NC1O)CCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of diethyl(4-methylphenyl)malonate (9.45 g) and butyramidine hydrochloride (5.00 g) in methanol (25 ml) is added 28% sodium methoxide (19.67 g) under ice-cooling, and the mixture is stirred at room temperature overnight. After the reaction is complete, the reaction solution is concentrated to the half vol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | CO | null | 8 | CCCC(=N)N.CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1>CO>CCCc1nc(O)c(-c2ccc(C)cc2)c(O)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ce4869becc14147b48b50fb8a727e75 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.c1ccsc1>>Cc1ccc(-c2c(Cl)nc(-c3cccs3)nc2Cl)cc1 | S1C=CC=C1.C(CCC)[Li].CCCCCC.ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O.C.CC1=CC=C(C=C1)C=1C(=NC=NC1Cl)Cl>>CC1=CC=C(C=C1)C=1C(=NC(=NC1Cl)C=1SC=CC1)Cl | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][cH:10][n:16][c:17]2[Cl:18])[cH:19][cH:20]1.[cH:11]1[cH:12][cH:13][cH:14][s:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][s:15]3)[n:16][c:17]2[Cl:18])[cH:19][cH:20]1 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.c1ccsc1 | Cc1ccc(-c2c(Cl)nc(-c3cccs3)nc2Cl)cc1 | null | null | C(C)(=O)O.O.O1CCCC1 | C-C Coupling | OtherReaction | 7477d571945f2e3c2b5e66e8121ec6c1e6cb8c3c83feee0f74fa4cf43ecd0b4c | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc(-c2cnc(-c3cccs3)nc2)cc1 | [#16;a:1]1:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1.[c:6]:[#7;a:7]:[cH;D2;+0:8]:[#7;a:9]:[c:10]>>[c:6]:[#7;a:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:5]1:[#16;a:1]:[c:2]:[c:3]:[c:4]:1):[#7;a:9]:[c:10] | 49.1 | [{"value": 49.1, "product": "CC1=CC=C(C=C1)C=1C(=NC(=NC1Cl)C=1SC=CC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | To a solution of thiophene (1.69 g) in anhydrous tetrahydrofuran (20 ml) is added dropwise a 1.6M n-butyl lithium/n-hexane solution (11.4 ml) at 0° C. under argon atmosphere over a period of 30 minutes. To the mixture is added dropwise and gradually a solution of 5-(4-methylphenyl)-4,6-dichloropyrimidine (4.0 g) in anh... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cncnc1.c1ccsc1 | c1cncnc1.c1ccsc1 | c1ccccc1.c1cncnc1.c1ccsc1 | null | C(C)(=O)O.O.O1CCCC1 | 0 | 1.5 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.c1ccsc1>C(C)(=O)O.O.O1CCCC1>Cc1ccc(-c2c(Cl)nc(-c3cccs3)nc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-92159ddf5fca43a09bd60ede97b3d342 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.[Li][c]1ccccc1>>Cc1ccc(-c2c(Cl)nc(-c3ccccc3)nc2Cl)cc1 | CC1=CC=C(C=C1)C=1C(=NC=NC1Cl)Cl.C1(=CC=CC=C1)[Li].C1CCCCC1>>CC1=CC=C(C=C1)C=1C(=NC(=NC1Cl)C1=CC=CC=C1)Cl | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][cH:10][n:17][c:18]2[Cl:19])[cH:20][cH:21]1.[Li][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][c:18]2[Cl:19])[cH:20][cH:21]1 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.[Li][c]1ccccc1 | Cc1ccc(-c2c(Cl)nc(-c3ccccc3)nc2Cl)cc1 | null | null | CCOCC | C-C Coupling | OtherReaction | 9a72b30d15d3a170453b5c35266e9d70841a0bbb9087716a1c585ee74f1223ea | cc013e751ce1c06538b7045e86b7a6f2058a4a034157294a153dbe8bc23160ba | c1ccc(-c2cnc(-c3ccccc3)nc2)cc1 | [Li]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[c:6]:[#7;a:7]:[cH;D2;+0:8]:[#7;a:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[#7;a:7]:[c:6]):[#7;a:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | A solution of 5-(4-methylphenyl)-4,6-dichloropyrimidine in ether is cooled at -30° C., and thereto is added dropwise a 1.8M phenyl lithium/cyclohexane solution. The reaction mixture is treated in the same manner as in Reference Example 20-(1) to give 5-(4-methylphenyl)-4,6-dichloro-2-phenylpyrimidine as crystalline pow... | 10.6084/m9.figshare.5104873.v1 | null | Aryl lithium | null | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | Li | CCOCC | null | null | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.[Li][c]1ccccc1>CCOCC>Cc1ccc(-c2c(Cl)nc(-c3ccccc3)nc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1f983a1da36340b0869e30cda784fc40 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1.Clc1ncc(Br)cn1>>Clc1ncc(-c2ccco2)cn1 | ClC1=NC=C(C=N1)Br.O1C(=CC=C1)[Sn](CCCC)(CCCC)CCCC>>ClC1=NC=C(C=N1)C=1OC=CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[cH:7][cH:8][cH:9][o:10]1.Br[c:5]1[cH:4][n:3][c:2]([Cl:1])[n:12][cH:11]1>>[Cl:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][o:10]2)[cH:11][n:12]1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1.Clc1ncc(Br)cn1 | Clc1ncc(-c2ccco2)cn1 | null | null | null | C-C Coupling | Stille reaction_aryl | 521e946f48ccffcbe6b23a0e1f700a0148118f44680a29c08207616fca9cfae6 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1coc(-c2cncnc2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7]1:[#8;a:8]:[c:9]:[c:10]:[c:11]:1>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7]2:[#8;a:8]:[c:9]:[c:10]:[c:11]:2):[c:6]:[#7;a:5]:[c:4]:1 | null | [] | null | null | null | null | 2-Chloro-5-bromopyrimidine and 2-furyltributyltin are treated in the same manner as in Example 190 to give 2-chloro-5-(2-furyl)pyrimidine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1cncnc1 | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1.Clc1ncc(Br)cn1>>Clc1ncc(-c2ccco2)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e36bdd34f9c40229a1193bb06a3ce85 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccsc1.Clc1ncc(Br)cn1>>Clc1ncc(-c2ccsc2)cn1 | ClC1=NC=C(C=N1)Br.S1C=C(C=C1)[Sn](CCCC)(CCCC)CCCC>>ClC1=NC=C(C=N1)C1=CSC=C1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[cH:7][cH:8][s:9][cH:10]1.Br[c:5]1[cH:4][n:3][c:2]([Cl:1])[n:12][cH:11]1>>[Cl:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][s:9][cH:10]2)[cH:11][n:12]1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccsc1.Clc1ncc(Br)cn1 | Clc1ncc(-c2ccsc2)cn1 | null | null | null | C-C Coupling | Stille reaction_aryl | 199420dc5768b1af27f86d7ad18eaf1b793cb98fd661ec8a8f552e8c67ad2d1d | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ncc(-c2ccsc2)cn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1>>[#16;a:9]1:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:2):[c:11]:[c:10]:1 | null | [] | null | null | null | null | 2-Chloro-5-bromopyrimidine and 3-thienyltributyltin are treated in the same manner as in Example 190 to give 2-chloro-5-(3-thienyl)pyrimidine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccsc1.c1cncnc1 | c1cncnc1.c1ccsc1 | c1cncnc1.c1ccsc1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccsc1.Clc1ncc(Br)cn1>>Clc1ncc(-c2ccsc2)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-271624f9843942ab8442a38e02129aa7 | ClCc1ccsc1.Oc1cnc(Cl)nc1>>Clc1ncc(OCc2ccsc2)cn1 | ClC1=NC=C(C=N1)O.ClCC1=CSC=C1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>ClC1=NC=C(C=N1)OCC1=CSC=C1 | Cl[CH2:7][c:8]1[cH:9][cH:10][s:11][cH:12]1.[Cl:1][c:2]1[n:3][cH:4][c:5]([OH:6])[cH:13][n:14]1>>[Cl:1][c:2]1[n:3][cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][s:11][cH:12]2)[cH:13][n:14]1 | ClCc1ccsc1.Oc1cnc(Cl)nc1 | Clc1ncc(OCc2ccsc2)cn1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ncc(OCc2ccsc2)cn1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1.[OH;D1;+0:7]-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1>>[#16;a:4]1:[c:5]:[c:6]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8]2:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:2):[c:3]:1 | 99.3 | [{"value": 99.3, "product": "ClC1=NC=C(C=N1)OCC1=CSC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | A mixture of 2-chloro-5-hydroxypyrimidine (200 mg), 3-chloromethylthiophene (610 mg), potassium carbonate (635 mg) and dimethylformamide (3 ml) is stirred at 50° C. for one hour. After the reaction is complete, to the reaction mixture is added water, and extracted with ethyl acetate. The organic layer is washed with wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cncnc1.c1ccsc1 | HCl | O | 50 | 1 | ClCc1ccsc1.Oc1cnc(Cl)nc1>O>Clc1ncc(OCc2ccsc2)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-202ad24f23144e29a486e05cf3ccb4db | NC(=O)c1cc(N)ccc1C(=O)Nc1ccc(N)cc1>>N#Cc1cc(N)ccc1C(=O)Nc1ccc(N)cc1 | CC(=O)C.OS(=O)(=O)O.O=S(=O)=O.NC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C(=C1)C(N)=O.[NH4+].[OH-]>>NC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C(=C1)C#N | O=[C:2]([NH2:1])[c:3]1[cH:4][c:5]([NH2:6])[cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([NH2:17])[cH:18][cH:19]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([NH2:6])[cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([NH2:17])[cH:18][cH:19]1 | NC(=O)c1cc(N)ccc1C(=O)Nc1ccc(N)cc1 | N#Cc1cc(N)ccc1C(=O)Nc1ccc(N)cc1 | null | null | C(C)O | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=C(Nc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3](:[c:4]):[c:5]-[C:6](-[#7:7])=[O;D1;H0:8]>>[#7:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:3](-[C;H0;D2;+0:1]#[N;H0;D1;+0:2]):[c:4] | null | [] | null | null | null | null | 350 ml of oleum (30% by weight) was cooled down below 0° C. using an ice bath, 99.6 g (0.368 mol) of 4,4'-diamino-6-carbamoyl benzanilide in a powder form was added below 5° C. with stirring. The stirring was continued to the next day, and the solution was neutralized by adding 1100 ml of NH4OH (28% by weight) already ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | NC(=O)c1cc(N)ccc1C(=O)Nc1ccc(N)cc1>C(C)O>N#Cc1cc(N)ccc1C(=O)Nc1ccc(N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9cf0611d38749c6a169a2037a147be6 | C1CCOC1.O=C1N[C@H](c2ccccc2)CO1>>CCCC[N+](CCCC)(CCCC)CCCC.O=C1N[C@H](c2ccccc2)CO1 | C1(=CC=CC=C1)[C@H]1NC(OC1)=O.[H-].[Na+].C1CCOC1>>C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)[C@H]1NC(OC1)=O | O1[CH2:1][CH2:14][CH2:15][CH2:16]1.[NH:5]1[C:19](=[O:18])[O:29][CH2:28][C@H:21]1[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N+:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:14][CH2:15][CH2:16][CH3:17].[O:18]=[C:19]1[NH:20][C@H:21]([c:22]2[cH:23][cH:24][cH:25][cH:26... | C1CCOC1.O=C1N[C@H](c2ccccc2)CO1 | CCCC[N+](CCCC)(CCCC)CCCC.O=C1N[C@H](c2ccccc2)CO1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | C-C Coupling | OtherReaction | 09778d9af7fde04154af0e39592ee4ce448955ccce539b65b1ac70ac1566a02b | c65c4f96eb20735d6c3621ff639a0b1b80493ea2862415b9e2d7a24c0b0536a0 | O=C1N[C@H](c2ccccc2)CO1 | O1-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[O;D1;H0:5]=[C;H0;D3;+0:6]1-[#8:7]-[C:8]-[C@@H;D3;+0:9](-[c:10](:[c:11]):[c:12])-[NH;D2;+0:13]-1>>[C:14]-[C:15]-[N+;H0;D4:13](-[C:16]-[C:17]-[C:18]-[CH3;D1;+0:4])(-[C:19]-[C:20])-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[C;D1;H3:21].[O;D1;H0:5]=[C;H0;D3;+0:6]1-[#7:22]-[C@H;... | null | [] | null | null | 30 | MINUTE | To a stirred solution of (R)-4-phenyl-2-oxazolidinone (174 mg, 1.06 mmol) in THF (4 mL) at 0° C., add NaH (4.3 mg, 60% emulsion in oil, 0.106 mmol). Allow the temperature to rise to room temperature over 30 min., then add tetra n-butylammonium bromide (34 mg, 0.106 mmol) to the mixture and stir for another 30 min. to o... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether | Carbamic ester.Ether | C1CCOC1.C1COCN1 | C1COCN1 | C1COCN1.c1ccccc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | 0.5 | C1CCOC1.O=C1N[C@H](c2ccccc2)CO1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>CCCC[N+](CCCC)(CCCC)CCCC.O=C1N[C@H](c2ccccc2)CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76651472f2d84918bce8909e6a061689 | Clc1ccc(I)cc1.Clc1ccccc1Cl.c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1>>Clc1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccc(Cl)cc3)cc2)cc1 | C1(=CC=CC=C1)NC1=CC=C(C=C1)NC1=CC=CC=C1.IC1=CC=C(C=C1)Cl.C1COCCOCCOCCOCCOCCO1.C([O-])([O-])=O.[K+].[K+].ClC1=C(C=CC=C1)Cl>>C1(=CC=CC=C1)N(C1=CC=C(C=C1)N(C1=CC=C(C=C1)Cl)C1=CC=CC=C1)C1=CC=C(C=C1)Cl | I[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:34][cH:33]1.Cl[c:23]1[c:18]([Cl:28])[cH:19][cH:20][cH:21][cH:22]1.[NH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([NH:17][c:24]2[cH:25][cH:26][cH:27][cH:29][cH:30]2)[cH:31][cH:32]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12... | Clc1ccc(I)cc1.Clc1ccccc1Cl.c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1 | Clc1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccc(Cl)cc3)cc2)cc1 | null | [Cu] | CCCCCC.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a653c775af516c3ff5ab1e2464b502a5e949e2df9114685330a6fec3418ed0b4 | f418d6272dad02aa82458c3dd91cd15bb8781bb54b86d001423e443c7ae41e4e | c1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccccc3)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-[Cl;H0;D1;+0:7].I-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[c:13]:[c:14](-[NH;D2;+0:15]-[c:16]1:[c:17]:[c:18]:[c:19](-[NH;D2;+0:20]-[c:21]2:[c:22]:[c:23]:[cH;D2;+0:24]:[c:25]:[c:26]:2):[c:27]:[c:28]:1):[c:29]>>[Cl;H0;D1;+0:7]-[c;H0;D3;+0:24]1:[c:23]:[c:22]:... | null | [] | 200 | CELSIUS | null | null | A 1 L, three-necked, round-bottomed flask, equipped with an overhead stirrer, a nitrogen inlet and a reflux condenser, was charged with N,N'-diphenyl-1,4-phenylenediamine (13.0 g, 0.05 mol), 4-iodochlorobenzene (31.0 g, 0.13 mol), copper bronze powder (12.7 g, 0.20 mol), 18-crown-6 ether (2.6 g, 0.10 mol), powdered pot... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Secondary amine.Secondary amine | Aromatic halide.Tertiary amine.Tertiary amine | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl.I- | [Cu].CCCCCC.C(Cl)Cl | 200 | null | Clc1ccc(I)cc1.Clc1ccccc1Cl.c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1>[Cu].CCCCCC.C(Cl)Cl>Clc1ccc(N(c2ccccc2)c2ccc(N(c3ccccc3)c3ccc(Cl)cc3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ec0108d9114945ba9e887e8acb30ed7f | NC(=O)Nc1ccccc1.NN>>NNC(=O)Nc1ccccc1 | NN.C1(=CC=CC=C1)NC(=O)N.NN>>C1(=CC=CC=C1)NC(NN)=O | [NH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.N[NH2:1]>>[NH2:1][NH:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | NC(=O)Nc1ccccc1.NN | NNC(=O)Nc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | e1c7dc7a5e70fef253b7e7f40a6385158a3c16d71bafa884450868de51a521b9 | 29efa48fb47552659a572494b97672efdaf1b6ae73a63009d32288dec9b93edb | c1ccccc1 | N-[NH2;D1;+0:1].[NH2;D1;+0:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6]>>[NH2;D1;+0:1]-[NH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6] | null | [] | null | null | null | null | Other known methods for the preparation of 4-aryl-1,2,4-triazol-3-ones involve the use of hydrazine as a raw material. In one such method, phenylurea is reacted with hydrazine to give a 4-phenylsemicarbazide. The semicarbazide is then condensed with ethyl formate to give the 4-phenyltriazolone. The overall yield from t... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Urea | Acylhydrazine | null | null | c1ccccc1 | Other | null | null | null | NC(=O)Nc1ccccc1.NN>>NNC(=O)Nc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e99cd70b8d1c4b8eabefb6d92273d488 | NNC(=O)Nc1ccccc1.O=CO>>O=CNNC(=O)Nc1ccccc1 | C1(=CC=CC=C1)NC(NN)=O.C(=O)O>>C(=O)NNC(=O)NC1=CC=CC=C1 | [NH2:3][NH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][NH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | NNC(=O)Nc1ccccc1.O=CO | O=CNNC(=O)Nc1ccccc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[#7:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[NH2;D1;+0:7]>>[#7:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[NH;D2;+0:7]-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | null | null | Other known methods for the preparation of 4-aryl-1,2,4-triazol-3-ones involve the use of hydrazine as a raw material. In one such method, phenylurea is reacted with hydrazine to give a 4-phenylsemicarbazide. The semicarbazide is then condensed with ethyl formate to give the 4-phenyltriazolone. The overall yield from t... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1 | HO- | null | null | null | NNC(=O)Nc1ccccc1.O=CO>>O=CNNC(=O)Nc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c607dee34d244a7e8f565c496317fb94 | FC(F)=CCCBr.Sc1nc2ccccc2s1>>FC(F)=CCCSc1nc2ccccc2s1 | BrCCC=C(F)F.BrCCC=C(F)F.C([O-])([O-])=O.[K+].[K+].SC=1SC2=C(N1)C=CC=C2.C([O-])([O-])=O.[K+].[K+]>>FC(=CCCSC=1SC2=C(N1)C=CC=C2)F | Br[CH2:6][CH2:5][CH:4]=[C:2]([F:1])[F:3].[SH:7][c:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[s:16]1>>[F:1][C:2]([F:3])=[CH:4][CH2:5][CH2:6][S:7][c:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[s:16]1 | FC(F)=CCCBr.Sc1nc2ccccc2s1 | FC(F)=CCCSc1nc2ccccc2s1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc2scnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]=[C:4](-[F;D1;H0:5])-[F;D1;H0:6].[SH;D1;+0:7]-[c:8]1:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:1>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])=[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[c:8]1:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:1 | 63 | [{"value": 63.0, "product": "FC(=CCCSC=1SC2=C(N1)C=CC=C2)F", "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 6 | HOUR | To the solution of 4-bromo-1,1-difluorobut-1-ene prepared in Example 6 was added potassium carbonate (10.76 g) and 2-mercaptobenzthiazole (9.18 g). The mixture was stirred at 55° C. for 6 hours and then at room temperature overnight. Gas-liquid chromatography of a sample of the reaction mixture showed that a small amou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2scnc2c1 | HBr | ClCCl | 55 | 6 | FC(F)=CCCBr.Sc1nc2ccccc2s1>ClCCl>FC(F)=CCCSc1nc2ccccc2s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e60c0ccb53946718e5945e7423510f1 | FC(CCBr)C(F)(F)Br.Sc1nc2ccccc2o1>>FC(F)=CCCSc1nc2ccccc2o1 | BrC(C(CCBr)F)(F)F.SC=1OC2=C(N1)C=CC=C2>>FC(=CCCSC=1OC2=C(N1)C=CC=C2)F | F[CH:4]([C:2](Br)([F:1])[F:3])[CH2:5][CH2:6]Br.[SH:7][c:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[o:16]1>>[F:1][C:2]([F:3])=[CH:4][CH2:5][CH2:6][S:7][c:8]1[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[o:16]1 | FC(CCBr)C(F)(F)Br.Sc1nc2ccccc2o1 | FC(F)=CCCSc1nc2ccccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3cdc643e2774edc9dd189ce32ffd0fa7797615837737c802aea81ea08103e059 | cb2f0132bcb1bf39bd4ac1f7bebbd736b8da28ab9cc03a2c62b248ebd3ed904b | c1ccc2ocnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[CH;D3;+0:3](-F)-[C;H0;D4;+0:4](-Br)(-[F;D1;H0:5])-[F;D1;H0:6].[SH;D1;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#8;a:12]:1>>[F;D1;H0:5]-[C;H0;D3;+0:4](-[F;D1;H0:6])=[CH;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#8;a:12]:1 | null | [] | null | null | null | null | To the solution of 4-bromo-1,1-difluorobut-1-ene prepared in Example 6 was added potassium carbonate (10.76 g) and 2-mercaptobenzthiazole (9.18 g). The mixture was stirred at 55° C. for 6 hours and then at room temperature overnight. Gas-liquid chromatography of a sample of the reaction mixture showed that a small amou... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Secondary halide.Primary halide.Aromatic thiol | Alkenyl halide.Alkenyl halide.Monosulfide | null | null | c1ccc2ocnc2c1 | HF.Br- | null | null | null | FC(CCBr)C(F)(F)Br.Sc1nc2ccccc2o1>>FC(F)=CCCSc1nc2ccccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-640b83ec08f243538919c6f734081f30 | C[Si](C)(C)CCOCn1nccc1C(=O)c1ccccc1[N+](=O)[O-]>>C[Si](C)(C)CCOCn1nccc1C(=O)c1ccccc1N | [N+](=O)([O-])C1=C(C(=O)C2=CC=NN2COCC[Si](C)(C)C)C=CC=C1>>NC1=C(C(=O)C2=CC=NN2COCC[Si](C)(C)C)C=CC=C1 | O=[N+:22]([O-])[c:21]1[c:16]([C:14]([c:13]2[n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[n:10][cH:11][cH:12]2)=[O:15])[cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][cH:12][c:13]1[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[NH2:... | C[Si](C)(C)CCOCn1nccc1C(=O)c1ccccc1[N+](=O)[O-] | C[Si](C)(C)CCOCn1nccc1C(=O)c1ccccc1N | null | null | C1CCOC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)c1ccn[nH]1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6] | 49 | [{"value": 49.0, "product": "NC1=C(C(=O)C2=CC=NN2COCC[Si](C)(C)C)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.8, "product": "NC1=C(C(=O)C2=CC=NN2COCC[Si](C)(C)C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The mixture of pyrazoles of examples 13C and 13D (2.35 g, 6.772 mmol) was taken up in dry THF (100 ml) and degassed. 5% Pd.-on-carbon (1.2 g) was added and the mixture hydrogenated at 30 psi and ambient temperature for 2 h. The mixture was filtered (celite filter aid) and evaporated and then chromatographed (eluant 30%... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccn[nH]1.c1ccccc1 | Other | C1CCOC1 | null | 2 | C[Si](C)(C)CCOCn1nccc1C(=O)c1ccccc1[N+](=O)[O-]>C1CCOC1>C[Si](C)(C)CCOCn1nccc1C(=O)c1ccccc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39eb4353217146abafbc990f86f0185c | CCOC(=O)NC1N=C(c2ccccn2)c2ccccc2N(CC(=O)C(C)(C)C)C1=O>>CC(C)(C)C(=O)CN1C(=O)C(N)N=C(c2ccccn2)c2ccccc21 | C(C)OC(=O)NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O.Br>>NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O | CCOC(=O)[NH:12][CH:11]1[C:9](=[O:10])[N:8]([CH2:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[c:26]2[c:21]([cH:22][cH:23][cH:24][cH:25]2)[C:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)=[N:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[CH2:7][N:8]1[C:9](=[O:10])[CH:11]([NH2:12])[N:13]=[C:14]([c:15]2[cH:16][cH:17]... | CCOC(=O)NC1N=C(c2ccccn2)c2ccccc2N(CC(=O)C(C)(C)C)C1=O | CC(C)(C)C(=O)CN1C(=O)C(N)N=C(c2ccccn2)c2ccccc21 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 878b485764081f6281e68f2ba6bab7d31c31c0c91b0b8d3614e74f76907da827 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C1CN=C(c2ccccn2)c2ccccc2N1 | C-C-O-C(=O)-[NH;D2;+0:1]-[C:2](-[#7:3]=[C:4])-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8]-[C:9]=[O;D1;H0:10])-[c:11]>>[C:4]=[#7:3]-[C:2](-[NH2;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8]-[C:9]=[O;D1;H0:10])-[c:11] | 91 | [{"value": 91.0, "product": "NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | (3RS)-Ethyloxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (IV, 250 mg, 0.592 mmol) was taken up in dry DCM (10 ml) at 0° C. and saturated with dry HBr gas. The mixture was stoppered and stirred at r.t. for 64 h. The solvent was evaporated and the product partitioned b... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | null | null | c1ccncc1.C1=NCC[NH]c2ccccc21 | HO- | C(Cl)Cl | null | 64 | CCOC(=O)NC1N=C(c2ccccn2)c2ccccc2N(CC(=O)C(C)(C)C)C1=O>C(Cl)Cl>CC(C)(C)C(=O)CN1C(=O)C(N)N=C(c2ccccn2)c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5570e335404a45e8bde112385306c6b2 | Nc1cccc(C(=O)O)c1.O=CO>>O=CNc1cccc(C(=O)O)c1 | C(C)(=O)OC(C)=O.C(=O)O.NC=1C=C(C(=O)O)C=CC1>>C(=O)NC=1C=C(C(=O)O)C=CC1 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12]1.O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12]1 | Nc1cccc(C(=O)O)c1.O=CO | O=CNc1cccc(C(=O)O)c1 | null | null | O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Acetic anhydride (76 ml) was added to 98% formic acid (130 ml) and the mixture stirred at r.t. 30 min, then 3-aminobenzoic acid (15 g, 109.5 mmol) added. The mixture was stirred at r.t. for 1 h, then water (1.3 L) added and stirring continued overnight. The resultant white precipitate was collected, washed with water a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O | null | null | Nc1cccc(C(=O)O)c1.O=CO>O>O=CNc1cccc(C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a5a2655fdf3f4f1cbc09910d0b12df9c | CI.O=CNc1cccc(C(=O)O)c1>>CN(C=O)c1ccccc1C(=O)O | IC.CN(C)C=O.C(=O)NC=1C=C(C(=O)O)C=CC1.[H-].[Na+].CN(C)C=O.IC>>C(=O)N(C)C1=C(C(=O)O)C=CC=C1 | I[CH3:1].[NH:2]([CH:3]=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:10]([C:11](=[O:12])[OH:13])[cH:9]1>>[CH3:1][N:2]([CH:3]=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[OH:13] | CI.O=CNc1cccc(C(=O)O)c1 | CN(C=O)c1ccccc1C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c9d83082ec710521e15304c050f42d0f8122726753293668018fe69df2107ba0 | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | c1ccccc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[O;D1;H1:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[C:11]=[O;D1;H0:12]):[cH;D2;+0:13]:1>>[CH3;D1;+0:1]-[N;H0;D3;+0:10](-[C:11]=[O;D1;H0:12])-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[cH;D2;+0:6]:[cH;D2;+0:13]:[c;H0;D3;+0:5]:1-[C:3](=[O;D1;H0:2])-[O;D1;H1:4] | 86 | [{"value": 86.0, "product": "C(=O)N(C)C1=C(C(=O)O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 3-Formylamino benzoic acid (2.28 g, 13.8 mmol) was taken up in DMF (25 ml) and added dropwise to a suspension of sodium hydride (1.05 g, 80% disp. in oil) in DMF (15 ml) at 0° C. The mixture was allowed to warm to r.t. over 1 h and then iodomethane (0.95 ml) added. A second portion of iodomethane (0.95 ml) was added af... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | null | null | 8 | CI.O=CNc1cccc(C(=O)O)c1>>CN(C=O)c1ccccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-21d973d5e9c342b28599ca4532af6af7 | C=CCCC(=O)Cl.COC(=O)c1cccc(N)c1>>C=CCCC(=O)Nc1cccc(C(=O)OC)c1 | COC(C1=CC(=CC=C1)N)=O.C(CCC=C)(=O)Cl.C(CCC=C)(=O)O.S(=O)(Cl)Cl>>C(CCC=C)(=O)NC=1C=C(C(=O)OC)C=CC1 | Cl[C:5]([CH2:4][CH2:3][CH:2]=[CH2:1])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17]1 | C=CCCC(=O)Cl.COC(=O)c1cccc(N)c1 | C=CCCC(=O)Nc1cccc(C(=O)OC)c1 | null | null | C(Cl)Cl.N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[C;D1;H2:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H2:6]=[C:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 32 | [{"value": 32.0, "product": "C(CCC=C)(=O)NC=1C=C(C(=O)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Methyl(3-amino)benzoate (4.5 g, 29.8 mmol) was taken up in DCM (10 ml) and pyridine (1 ml) at 0° C. 4-Pentenoyl chloride (freshly prepared from 4-pentenoic acid (3.0 g, 29.97 mmol) and thionyl chloride (6.6 ml) at r.t. for 1 h, evaporated and azeotroped with DCM) was added dropwise in DCM (3 ml). The mixture was allowe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(Cl)Cl.N1=CC=CC=C1 | null | 8 | C=CCCC(=O)Cl.COC(=O)c1cccc(N)c1>C(Cl)Cl.N1=CC=CC=C1>C=CCCC(=O)Nc1cccc(C(=O)OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39e2a12366cc4afaa1054c2e96602afd | COC(=O)c1cccc(NC(=O)CCCCBr)c1>>COC(=O)c1cccc(N2CCCCC2=O)c1 | BrCCCCC(=O)NC=1C=C(C(=O)OC)C=CC1.[H-].[Na+]>>O=C1N(CCCC1)C=1C=C(C(=O)OC)C=CC1 | Br[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17]1)=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2=[O:16])[cH:17]1 | COC(=O)c1cccc(NC(=O)CCCCBr)c1 | COC(=O)c1cccc(N2CCCCC2=O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 9dfd2b7906d79dea91b8c168207af33ec48cc64e1e8d843c068b11dc21f26e62 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCCCN1c1ccccc1 | 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]>>[O;D1;H0:6]=[C:5]1-[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]-1-[c:8](:[c:9]):[c:10] | 56.2 | [{"value": 56.0, "product": "O=C1N(CCCC1)C=1C=C(C(=O)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "O=C1N(CCCC1)C=1C=C(C(=O)OC)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | The bromide of Example 36 (1.50 g, 4.88 mmol) was taken up in dry DMF (40 ml) and treated with NaH (160 mg, 80% disp. in oil) at 0° C. The mixture was stirred at r.t. under nitrogen for 10 min, then KI (80 mg) added and the mixture heated at 70° C. for 4 h. The mixture was evaporated and partitioned between EtOAc and 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | CN(C)C=O | null | 0.166667 | COC(=O)c1cccc(NC(=O)CCCCBr)c1>CN(C)C=O>COC(=O)c1cccc(N2CCCCC2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b2a2fb45af4f44099c49615f8d09865c | COC(=O)c1cccc(N2CCCCC2=O)c1>>COC(=O)c1cccc(N2CCCCC2)c1 | O=C1N(CCCC1)C=1C=C(C(=O)OC)C=CC1.B.O1CCCC1>>N1(CCCCC1)C=1C=C(C(=O)OC)C=CC1 | O=[C:15]1[N:10]([c:9]2[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:16]2)[CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:16]1 | COC(=O)c1cccc(N2CCCCC2=O)c1 | COC(=O)c1cccc(N2CCCCC2)c1 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | a9fd579e7faaaa094227b38014f5494172546cdc7c9d2d1b8815d615c0aa21f2 | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc(N2CCCCC2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[#7:4](-[c:5])-[C:6]>>[C:6]-[#7:4](-[c:5])-[CH2;D2;+0:1]-[C:2]-[C:3] | 90 | [{"value": 90.0, "product": "N1(CCCCC1)C=1C=C(C(=O)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "N1(CCCCC1)C=1C=C(C(=O)OC)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound of Example 37 (640 mg, 2.75 mmol) was dissolved in dry THF (30 ml) and borane-tetrahydrofuran complex (5 ml, 1M solution in THF) was added. The mixture was stirred under nitrogen under reflux for 1 h, then cooled and evaporated. The residue was taken up in MeOH/acetic acid (6/1, v/v, 70 ml) and heated unde... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | Other | C1CCOC1 | null | null | COC(=O)c1cccc(N2CCCCC2=O)c1>C1CCOC1>COC(=O)c1cccc(N2CCCCC2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-227139b0204b412c8ef4f1e745340ffc | COC(=O)c1cccc(N2CCCCC2)c1>>O=C(O)c1cccc(N2CCCCC2)c1 | N1(CCCCC1)C=1C=C(C(=O)OC)C=CC1.O.[OH-].[Li+].C(C)(=O)O>>N1(CCCCC1)C=1C=C(C(=O)O)C=CC1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15]1 | COC(=O)c1cccc(N2CCCCC2)c1 | O=C(O)c1cccc(N2CCCCC2)c1 | null | null | O.O1CCOCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(N2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 90 | [{"value": 90.0, "product": "N1(CCCCC1)C=1C=C(C(=O)O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "N1(CCCCC1)C=1C=C(C(=O)O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 1 | HOUR | The compound of Example 38 (540 mg, 2.466 mmol) was dissolved in dioxan (12 ml) and water (8 ml). Lithium hydroxide hydrate (300 mg, 7.143 mmol) was added and the mixture stirred at 40° C. for 1 h. The mixture was acidified with acetic acid, evaporated, azeotroped with toluene and chromatographed on silica (eluant 60/4... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]CC1 | Other | O.O1CCOCC1 | 40 | 1 | COC(=O)c1cccc(N2CCCCC2)c1>O.O1CCOCC1>O=C(O)c1cccc(N2CCCCC2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5df61b0f843d454b91abd7c3ea08a12b | CCOC(N)=O.O=CC(=O)O.c1ccc2[nH]nnc2c1>>CCOC(=O)N(CC(=O)O)n1nnc2ccccc21 | C(N)(OCC)=O.O.C(C=O)(=O)O.N1N=NC2=C1C=CC=C2>>C(C)OC(=O)N(CC(=O)O)N1N=NC2=C1C=CC=C2 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[NH2:6].O=[CH:7][C:8](=[O:9])[OH:10].[nH:11]1[n:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]([CH2:7][C:8](=[O:9])[OH:10])[n:11]1[n:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CCOC(N)=O.O=CC(=O)O.c1ccc2[nH]nnc2c1 | CCOC(=O)N(CC(=O)O)n1nnc2ccccc21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | f2955afb7a3443f2b2c397c64400d5c18b12961d9a2e873e83477c7c17c5b083 | 75f6f3cbd3c0325a929f41a15c9cdeffc50914512b22e7019b0acebcd00ef2c9 | c1ccc2[nH]nnc2c1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[C:5]-[#8:6]-[C:7](-[NH2;D1;+0:8])=[O;D1;H0:9].[c:10]:[c:11]1:[#7;a:12]:[#7;a:13]:[nH;D2;+0:14]:[c:15]:1:[c:16]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:9])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[n;H0;D3;+0:14]1:[#7;a:13]:[#7;a:12]:[c:11](:[c:10]):[c:15]:1:[c... | 96 | [{"value": 96.0, "product": "C(C)OC(=O)N(CC(=O)O)N1N=NC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C(C)OC(=O)N(CC(=O)O)N1N=NC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 8 | HOUR | Ethyl carbamate (69.0 g, 774.5 mmol), glyoxylic acid hydrate (71.3 g, 774.5 mmol) and benzotriazole (92.0 g, 774.5 mmol) were dissolved in toluene (2.3 1) and the mixture was heated with distillation for 3 h to precipitate the product. The mixture was diluted with toluene (totally 2.3 1) and stirred at 15° C. overnight... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester | Carbamic ester | c1ccc2[nH]nnc2c1 | c1ccc2[nH]nnc2c1 | c1ccc2[nH]nnc2c1 | HO- | C1(=CC=CC=C1)C | 15 | 8 | CCOC(N)=O.O=CC(=O)O.c1ccc2[nH]nnc2c1>C1(=CC=CC=C1)C>CCOC(=O)N(CC(=O)O)n1nnc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ddb2942de49c4b9a90cdb5a3cda50c77 | CCOC(=O)NC1N=C(c2ccccn2)c2ccccc2N(CC(=O)C(C)(C)C)C1=O>>CC(C)(C)C(=O)CN1C(=O)C(N)N=C(c2ccccn2)c2ccccc21 | C(C)OC(=O)NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O.Cl>>NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O | CCOC(=O)[NH:12][CH:11]1[C:9](=[O:10])[N:8]([CH2:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[c:26]2[c:21]([cH:22][cH:23][cH:24][cH:25]2)[C:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)=[N:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[CH2:7][N:8]1[C:9](=[O:10])[CH:11]([NH2:12])[N:13]=[C:14]([c:15]2[cH:16][cH:17]... | CCOC(=O)NC1N=C(c2ccccn2)c2ccccc2N(CC(=O)C(C)(C)C)C1=O | CC(C)(C)C(=O)CN1C(=O)C(N)N=C(c2ccccn2)c2ccccc21 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 878b485764081f6281e68f2ba6bab7d31c31c0c91b0b8d3614e74f76907da827 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C1CN=C(c2ccccn2)c2ccccc2N1 | C-C-O-C(=O)-[NH;D2;+0:1]-[C:2](-[#7:3]=[C:4])-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8]-[C:9]=[O;D1;H0:10])-[c:11]>>[C:4]=[#7:3]-[C:2](-[NH2;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8]-[C:9]=[O;D1;H0:10])-[c:11] | 93.3 | [{"value": 93.0, "product": "NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "NC1C(N(C2=C(C(=N1)C1=NC=CC=C1)C=CC=C2)CC(=O)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 50 | HOUR | A solution of (3RS)-ethoxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (10.0 g, 23.7 mmol) in DCM (40 ml) was added to the above solution below 25° C. and the mixture was stirred for 50 h. The mixture was then poured into 3M HCl (80 ml) below 25° C. and the aqueous por... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | null | null | c1ccncc1.C1=NCC[NH]c2ccccc21 | HO- | C(Cl)Cl | null | 50 | CCOC(=O)NC1N=C(c2ccccn2)c2ccccc2N(CC(=O)C(C)(C)C)C1=O>C(Cl)Cl>CC(C)(C)C(=O)CN1C(=O)C(N)N=C(c2ccccn2)c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-55f511a55d61454a83be8c226edee531 | Cl>>Cl | C(C)(C)(C)C(=O)CN1C([C@@H](N=C(C2=C1C=CC=C2)C2=NC=CC=C2)NC(=O)NC2=CC(=CC=C2)N(C)C)=O.C(C)O.Cl>>Cl.C(C)(C)(C)C(=O)CN1C([C@@H](N=C(C2=C1C=CC=C2)C2=NC=CC=C2)NC(=O)NC2=CC(=CC=C2)N(C)C)=O | [ClH:39]>>[ClH:39] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 50 | CELSIUS | 8 | HOUR | N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-dimethylaminophenyl)urea (70 g, 136.6 mmol) was taken up in ethanol (1 l) and 2.26M HCl ethanol (63.5 ml, 143.4 mmol) was added dropwise. The mixture was warmed up to 50° C. to afford a clear solution, which was seeded, ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | 50 | 8 | Cl>C(C)O>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0e3813329fd4701a3a3f986ee306d00 | CCOC(=O)Cl.CN(C(=O)OC(C)(C)C)c1cccc(C(=O)O)c1>>CN(C(=O)OC(C)(C)C)c1cccc(N=C=O)c1 | [N-]=[N+]=[N-].[Na+].CCN(CC)CC.ClC(=O)OCC.O(C(C)(C)C)C(=O)N(C)C=1C=C(C(=O)O)C=CC1>>O(C(C)(C)C)C(=O)N(C)C=1C=C(C=CC1)N=C=O | CCO[C:16](Cl)=[O:17].O=C(O)[c:14]1[cH:13][cH:12][cH:11][c:10]([N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[cH:18]1>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([N:15]=[C:16]=[O:17])[cH:18]1 | CCOC(=O)Cl.CN(C(=O)OC(C)(C)C)c1cccc(C(=O)O)c1 | CN(C(=O)OC(C)(C)C)c1cccc(N=C=O)c1 | null | null | C1(=CC=CC=C1)C.O.CC(=O)C | Protection | OtherReaction | c10a61766aae74484ca819d3bc673441d5a3ac212905587e31e25acab95896c9 | ad3ce9de5d008e6fe42518a159a24df64edec84808853d24edaa142b8df8c38e | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].O-C(=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[#7:8]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7] | 78.5 | [{"value": 78.0, "product": "O(C(C)(C)C)C(=O)N(C)C=1C=C(C=CC1)N=C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "O(C(C)(C)C)C(=O)N(C)C=1C=C(C=CC1)N=C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Et3N (3.71 g, 36.7 mmol) and a solution of ethyl chloroformate (4.31 g, 39.7 mmol) in acetone (10 ml) were successively added dropwise to a solution of 3-(N-tert-butoxylcarbonyl-N-methylamino)benzoic acid (8.0 g, 31.8 mmol) in acetone (64 ml) below 5° C. After stirring for 30 min, a solution of NaN3 (3.10 g, 47.7 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether | Isocyanate | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C1(=CC=CC=C1)C.O.CC(=O)C | null | 0.5 | CCOC(=O)Cl.CN(C(=O)OC(C)(C)C)c1cccc(C(=O)O)c1>C1(=CC=CC=C1)C.O.CC(=O)C>CN(C(=O)OC(C)(C)C)c1cccc(N=C=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d183881774224975a1ab61e1760c6bad | Cc1ccc(S(=O)(=O)Cl)cc1.OCC(O)CO>>Cc1ccc(S(=O)(=O)OCC(O)COS(=O)(=O)c2ccc(C)cc2)cc1 | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.OCC(O)CO.Cl>>S(=O)(=O)(C1=CC=C(C)C=C1)OCC(O)COS(=O)(=O)C1=CC=C(C)C=C1 | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:26][cH:25]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH:11]([OH:12])[CH2:22][OH:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH:11]([OH:12])[CH2:13][O:14][S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][c:21]([CH3:22])[cH:23][cH:24]2)[cH:25][cH:26]1 | Cc1ccc(S(=O)(=O)Cl)cc1.OCC(O)CO | Cc1ccc(S(=O)(=O)OCC(O)COS(=O)(=O)c2ccc(C)cc2)cc1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 051c238cc697fb95d521a378790a706996235c75768c9bc7f5f19c4bbb363bb0 | be3f629adcb32a776ba877fc0c1beb58f88fbbb93daba66fe1621aea210f656a | O=S(=O)(OCCCOS(=O)(=O)c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[O;D1;H1:7]-[CH;D3;+0:8](-[C:9]-[OH;D1;+0:10])-[CH2;D2;+0:11]-[OH;D1;+0:12]>>[CH3;D1;+0:11]-[c:13](:[c:14]):[c:15].[O;D1;H0:16]=[#16:17](=[O;D1;H0:18])(-[c:19])-[O;H0;D2;+0:12]-[C:20]-[CH;D3;+0:8](-[O;D1;H1:7])-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1... | null | [] | null | null | null | null | Compound 2 was synthesized according to the previous reported method with modifications (Benbouzid et al., 1988). p-Toluenesulfonyl chloride (10.29 g, 54 mmol) dissolved in dry pyridine was added to a stirred solution of anhydrous glycerol (2.48 g, 27 mmol) in dry pyridine (30 ml at 0° C.). The solution was added slowl... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Primary alcohol.Secondary alcohol.Sulfonyl halide | Tosylate.Tosylate.Secondary alcohol | null | c1ccccc1 | c1ccccc1.c1ccccc1 | null | N1=CC=CC=C1 | null | null | Cc1ccc(S(=O)(=O)Cl)cc1.OCC(O)CO>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)OCC(O)COS(=O)(=O)c2ccc(C)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0fdf59899d7d46d0ae418ee316a592b9 | CCCCc1nc(Cl)c(CO)[nH]1>>CCCCc1nc(Cl)c(C=O)[nH]1 | C(CCC)C=1NC(=C(N1)Cl)CO.O>>C(CCC)C=1NC(=C(N1)Cl)C=O | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH2:10][OH:11])[nH:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH:10]=[O:11])[nH:12]1 | CCCCc1nc(Cl)c(CO)[nH]1 | CCCCc1nc(Cl)c(C=O)[nH]1 | null | [O-2].[O-2].[Mn+4] | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1c[nH]cn1 | [Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8]>>[Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[CH;D2;+0:7]=[O;H0;D1;+0:8] | 86.3 | [{"value": 86.0, "product": "C(CCC)C=1NC(=C(N1)Cl)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "C(CCC)C=1NC(=C(N1)Cl)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 2-n-butyl-4-chloro-5-hydroxymethylimidazole (15.00 g, 0.0795 mol) and activated manganese dioxide (40.00 g) in 600 ml of methylene chloride was refluxed for 24 h using a water separator. The mixture was filtered hot through a Celite® pad. The Celite® pad was washed several times with hot methylene ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1c[nH]cn1 | null | [O-2].[O-2].[Mn+4].C(Cl)Cl | null | null | CCCCc1nc(Cl)c(CO)[nH]1>[O-2].[O-2].[Mn+4].C(Cl)Cl>CCCCc1nc(Cl)c(C=O)[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2843bd13368f422ab3826093b175bc25 | CCCCC(=N)N.CCO.COC(=O)C=CC=O>>CCCCc1nc(CC(=O)OCC)c[nH]1 | C(=O)C=CC(=O)OC.[H-].[Na+].C(C)O.Cl.C(CCCC)(=N)N>>C(CCC)C=1NC=C(N1)CC(=O)OCC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[NH:6])[NH2:15].OC[CH3:13].O=[CH:14][CH:7]=[CH:8][C:9](=[O:10])[O:11][CH3:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([CH2:8][C:9](=[O:10])[O:11][CH2:12][CH3:13])[cH:14][nH:15]1 | CCCCC(=N)N.CCO.COC(=O)C=CC=O | CCCCc1nc(CC(=O)OCC)c[nH]1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | f6d52ea8c1ef3a677e8faa4e6193cce69d7709e564ab85a4c0c46d0a6694d531 | 373cfe5f2ced9afde13ee4279ab98d0c57bacbc28362be854cec0c75098b2267 | c1c[nH]cn1 | O-C-[CH3;D1;+0:1].O=[CH;D2;+0:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[CH3;D1;+0:8].[C:9]-[C:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[NH;D1;+0:13]>>[C:9]-[C:10]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:3](-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[CH2;D2;+0:8]-[CH3;D1;+0:1]):[cH;D2;+0:2]:[nH;D2;+0:12]:... | null | [] | null | null | null | null | Sodium hydride (2.82 g, 0,117 mol) was dissolved in 30 ml of absolute ethanol at 0° C. Valeramidine hydrochloride (16.71 g, 0.123 mol) was added to this solution, and after 15 minutes the solution was filtered and the collected solid was washed with 20 ml of ethanol and 50 ml of benzene. The combined filtrates were dil... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Primary alcohol.Primary amine | Ester | null | c1c[nH]cn1 | c1c[nH]cn1 | HO- | C1=CC=CC=C1 | null | null | CCCCC(=N)N.CCO.COC(=O)C=CC=O>C1=CC=CC=C1>CCCCc1nc(CC(=O)OCC)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-132a212c419b44f6b52e3b5ef79af5b4 | CCCCc1nc(CO)c[nH]1.O=C1CCC(=O)N1I>>CCCCc1nc(I)c(CO)[nH]1 | IN1C(CCC1=O)=O.C(CCC)C=1NC=C(N1)CO>>C(CCC)C=1NC(=C(N1)I)CO | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[nH:6][cH:7][c:9]([CH2:10][OH:11])[n:12]1.O=C1CCC(=O)N1[I:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([I:8])[c:9]([CH2:10][OH:11])[nH:12]1 | CCCCc1nc(CO)c[nH]1.O=C1CCC(=O)N1I | CCCCc1nc(I)c(CO)[nH]1 | null | null | C(C)O.O | Functional Group Interconversion | OtherReaction | 339179e6c50945dd3ac07a96a57059a7154e475073d7636ad2fc68e36469c54f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1c[nH]cn1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[C:2]-[c:3]1:[cH;D2;+0:4]:[nH;D2;+0:5]:[c:6](-[C:7]):[n;H0;D2;+0:8]:1>>[C:2]-[c:3]1:[nH;D2;+0:8]:[c:6](-[C:7]):[n;H0;D2;+0:5]:[c;H0;D3;+0:4]:1-[I;H0;D1;+0:1] | 95 | [{"value": 95.0, "product": "C(CCC)C=1NC(=C(N1)I)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-iodosuccinimide (148.75 g, 0.661 mol) was added to a stirred solution of 2-n-butyl-4-hydroxymethylimidazole (100.78 g, 0.652 mol) in 500 ml of absolute ethanol. After 20 minutes the solution was heated to 40°-45° C. for 45 minutes, diluted with 2.5 L of water, and chilled. The crystalline product which formed was col... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1c[nH]cn1.C1CCNC1 | c1c[nH]cn1 | c1c[nH]cn1 | HO- | C(C)O.O | null | null | CCCCc1nc(CO)c[nH]1.O=C1CCC(=O)N1I>C(C)O.O>CCCCc1nc(I)c(CO)[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-de21b1de13124c589802a272f7412025 | CCCCc1nc(I)c(CO)[nH]1>>CCCCc1nc(I)c(C=O)[nH]1 | C(CCC)C=1NC(=C(N1)I)CO>>C(CCC)C=1NC(=C(N1)I)C=O | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([I:8])[c:9]([CH2:10][OH:11])[nH:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([I:8])[c:9]([CH:10]=[O:11])[nH:12]1 | CCCCc1nc(I)c(CO)[nH]1 | CCCCc1nc(I)c(C=O)[nH]1 | null | [O-2].[O-2].[Mn+4] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1c[nH]cn1 | [I;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8]>>[I;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[CH;D2;+0:7]=[O;H0;D1;+0:8] | 84.2 | [{"value": 84.0, "product": "C(CCC)C=1NC(=C(N1)I)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "C(CCC)C=1NC(=C(N1)I)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 174.1 g (0.62 mol) of 2-n-butyl-5-hydroxymethyl-4-iodoimidazole and 360 g (4.14 mol) of manganese dioxide in 3 L of dichloromethane was refluxed for 24 hr using a trap to remove water. The hot reaction mixture was filtered through a Celite® pad which was then washed with 4.5 L of boiling methylene ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1c[nH]cn1 | null | [O-2].[O-2].[Mn+4].ClCCl | null | null | CCCCc1nc(I)c(CO)[nH]1>[O-2].[O-2].[Mn+4].ClCCl>CCCCc1nc(I)c(C=O)[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ff9fddba17f84a17b2c77c4ed15d72d3 | CCCCc1nc(I)c(C=O)[nH]1.COC(=O)c1ccc(CBr)c2ccccc12>>CCCCC1N=C(I)C(C=O)(Cc2ccc(C(=O)OC)c3ccccc23)N1 | C([O-])([O-])=O.[K+].[K+].C(CCC)C=1NC(=C(N1)I)C=O.BrCC1=CC=C(C2=CC=CC=C12)C(=O)OC.O>>C(CCC)C1NC(C(=N1)I)(C=O)CC1=CC=C(C2=CC=CC=C12)C(=O)OC | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([I:8])[c:9]([CH:10]=[O:11])[nH:27]1.Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[O:19][CH3:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[N:6]=[C:7]([I:8])[C:9]([CH:10]=[O:11])([CH2:12][c:13]2[cH:14][cH:15][c:16]([C:17](=[O:18])... | CCCCc1nc(I)c(C=O)[nH]1.COC(=O)c1ccc(CBr)c2ccccc12 | CCCCC1N=C(I)C(C=O)(Cc2ccc(C(=O)OC)c3ccccc23)N1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | d8c74bd68b3292fafed319bd6ec34baf915d17a5e15132d7b20991dcb6ff2b9a | 1fb0e31b83cdc0f1a3d139358556d22838f4ec7845f0c3ac45c5d2b6cea2942b | C1=NCNC1Cc1cccc2ccccc12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[I;D1;H0:10]):[c;H0;D3;+0:11](-[C:12]=[O;D1;H0:13]):[nH;D2;+0:14]:1>>[C:5]-[C:6]-[CH;D3;+0:7]1-[N;H0;D2;+0:8]=[C;H0;D3;+0:9](-[I;D1;H0:10])-[C;H0;D4;+0:11](-[C:12]=[O;D1;H0:13])(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:... | 85 | [{"value": 85.0, "product": "C(CCC)C1NC(C(=N1)I)(C=O)CC1=CC=C(C2=CC=CC=C12)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "C(CCC)C1NC(C(=N1)I)(C=O)CC1=CC=C(C2=CC=CC=C12)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 15 | HOUR | A suspension of 29.53 g (0.214 mol) of powdered potassium carbonate, 60.00 g (0.214 mol) of 2-butyl-4-iodoimidazole-5-carboxaldehyde, and 65.68 g (0.235 mol) of methyl 4-bromomethylnaphthalene-1-carboxylate (E. A. Dixon, A. Fischer, and F. P. Robinson, Can. J. Chem. 59, 2629 (1981)) in 600 ml of dimethylformamide was s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Aldehyde | Alkenyl halide.Aldehyde.Secondary amine | c1c[nH]cn1 | C1=NCNC1 | C1=NCNC1.c1ccc2ccccc2c1 | Br- | CN(C=O)C | 70 | 15 | CCCCc1nc(I)c(C=O)[nH]1.COC(=O)c1ccc(CBr)c2ccccc12>CN(C=O)C>CCCCC1N=C(I)C(C=O)(Cc2ccc(C(=O)OC)c3ccccc23)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f310c91312a24ed185ed64c535694b9b | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1.[NH4+]>>COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | C1(C=2C(C(N1C(CC(=O)O)C1=CC(=C(C=C1)OC)OC1CCCC1)=O)=CC=CC2)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.[OH-].[NH4+]>>C1(C=2C(C(N1C(CC(=O)N)C1=CC(=C(C=C1)OC)OC1CCCC1)=O)=CC=CC2)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[cH:23]1)[N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22])=[O:11].[NH4+:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9]([NH2:10])=[O:11])[N:12]2[C:13](=[O:14])[c:15... | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1.[NH4+] | COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | null | CN(C1=CC=NC=C1)C | O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1c2ccccc2C(=O)N1Cc1cccc(OC2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 62.2 | [{"value": 62.2, "product": "C1(C=2C(C(N1C(CC(=O)N)C1=CC(=C(C=C1)OC)OC1CCCC1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 1.5 | HOUR | A mixture of 3-phthalimido-3-(3-cyclopentyloxy-4-methoxyphenyl)propionic acid (2.05 g, 5.00 mmol), 1,1'-carbonyldiimidazole (0.91 g, 5.5 mmol) and 4-dimethylaminopyridine (trace) in tetrahydrofuran (20 mL) was stirred for 1.5 hours under nitrogen at approximately 25° C. To the solution was added ammonium hydroxide (1.0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | CN(C1=CC=NC=C1)C.O1CCCC1 | 25 | 1.5 | COc1ccc(C(CC(=O)O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1.[NH4+]>CN(C1=CC=NC=C1)C.O1CCCC1>COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48bcadbbba7b4f4299bd816594d61a87 | COc1ccc(C=O)cc1OC1CCCC1.C[Si](C)(C)N[Si](C)(C)C>>CCC(N)c1ccc(OC)c(OC2CCCC2)c1 | C(C)[Mg]Br.C(CCC)[Li].C[Si](N[Si](C)(C)C)(C)C.C1(CCCC1)OC=1C=C(C=O)C=CC1OC.[Cl-].[NH4+]>>C1(CCCC1)OC=1C=C(C=CC1OC)C(CC)N | O=[CH:3][c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18]1.C[Si](C)(C)[NH:4][Si](C)(C)C>>[CH3:1][CH2:2][CH:3]([NH2:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18]1 | COc1ccc(C=O)cc1OC1CCCC1.C[Si](C)(C)N[Si](C)(C)C | CCC(N)c1ccc(OC)c(OC2CCCC2)c1 | null | null | CC#N.CCCCCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 13e3e72401395cfde3aa1eedd418837033025f6f253a59da5c4d1e1750b92879 | 49265bb2bfa9eef218bd07821ad7c78053d001bea6481ce70742cda21ee85079 | c1ccc(OC2CCCC2)cc1 | C-[Si](-C)(-C)-[NH;D2;+0:1]-[Si](-C)(-C)-C.O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C:7]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | To an ice bath cooled stirred solution of 1,1,1,3,3,3-hexamethyldisilazane (2.5M, 4.1 mL, 19.5 mmol) in tetrahydrofuran (5 mL) under nitrogen, was added a hexane solution of butyl lithium (7.2 mL, 18 mmol) via syringe. The ice bath was removed and the solution was stirred for 30 minutes at room temperature. This soluti... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine.Silyl protective group.Silyl protective group | Primary amine | null | null | c1ccccc1.C1CCCC1 | HO- | CC#N.CCCCCC.O1CCCC1 | null | 0.5 | COc1ccc(C=O)cc1OC1CCCC1.C[Si](C)(C)N[Si](C)(C)C>CC#N.CCCCCC.O1CCCC1>CCC(N)c1ccc(OC)c(OC2CCCC2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a172f4e4b1614e5bac954c6d01d97ff6 | COc1ccc(C=O)cc1OC1CCc2ccccc21.C[Si](C)(C)N[Si](C)(C)C>>CCC(N)c1ccc(OC)c(OC2CCc3ccccc32)c1 | C(C)[Mg]Br.C(CCC)[Li].C[Si](N[Si](C)(C)C)(C)C.C1(CCC2=CC=CC=C12)OC=1C=C(C=O)C=CC1OC.[Cl-].[NH4+]>>C1(CCC2=CC=CC=C12)OC=1C=C(C=CC1OC)C(CC)N | O=[CH:3][c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH:13]2[CH2:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22]1.C[Si](C)(C)[NH:4][Si](C)(C)C>>[CH3:1][CH2:2][CH:3]([NH2:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH:13]2[CH2:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22... | COc1ccc(C=O)cc1OC1CCc2ccccc21.C[Si](C)(C)N[Si](C)(C)C | CCC(N)c1ccc(OC)c(OC2CCc3ccccc32)c1 | null | null | CC#N.CCCCCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 13e3e72401395cfde3aa1eedd418837033025f6f253a59da5c4d1e1750b92879 | 49265bb2bfa9eef218bd07821ad7c78053d001bea6481ce70742cda21ee85079 | c1ccc(OC2CCc3ccccc32)cc1 | C-[Si](-C)(-C)-[NH;D2;+0:1]-[Si](-C)(-C)-C.O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C:7]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[c:3](:[c:4]):[c:5] | 9 | [{"value": 9.0, "product": "C1(CCC2=CC=CC=C12)OC=1C=C(C=CC1OC)C(CC)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 25 | MINUTE | To an ice bath cooled stirred solution of 1,1,1,3,3,3-hexamethyldisilazane (2.7 mL, 13 mmol) in tetrahydrofuran (5 mL) under nitrogen, was added a hexane solution of butyl lithium (2.5M, 4.8 mL, 12 mmol) via syringe. The ice bath was removed and the solution was stirred for 25 minutes at room temperature. This solution... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine.Silyl protective group.Silyl protective group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC2 | HO- | CC#N.CCCCCC.O1CCCC1 | null | 0.416667 | COc1ccc(C=O)cc1OC1CCc2ccccc21.C[Si](C)(C)N[Si](C)(C)C>CC#N.CCCCCC.O1CCCC1>CCC(N)c1ccc(OC)c(OC2CCc3ccccc32)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e365fd6c4897470482774680a6343b87 | CCOc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OCC>>CCOc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OCC | CC#N.OP(=O)(O)O.C(=O)(O)[O-].[Na+].C1(C=2C(C(N1C(CC(=O)N)C1=CC(=C(C=C1)OCC)OCC)=O)=CC=CC2)=O.CN1CCOCC1.S(=O)(Cl)Cl>>C1(C=2C(C(N1C(CC#N)C1=CC(=C(C=C1)OCC)OCC)=O)=CC=CC2)=O | O=[C:10]([CH2:9][CH:8]([c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:24]([O:25][CH2:26][CH3:27])[cH:23]1)[N:12]1[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22])[NH2:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH2:9][C:10]#[N:11])[N:12]2[C:13](=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:... | CCOc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OCC | CCOc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OCC | null | null | CN(C)C=O | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[C;H0;D2;+0:1]#[N;H0;D1;+0:2] | 55 | [{"value": 55.0, "product": "C1(C=2C(C(N1C(CC#N)C1=CC(=C(C=C1)OCC)OCC)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.9, "product": "C1(C=2C(C(N1C(CC#N)C1=CC(=C(C=C1)OCC)OCC)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To an ice bath cooled stirred suspension of 3-phthalimido-3-(3,4-diethoxyphenyl)propionamide (0.96 g, 2.5 mmol) and 4-methylmorpholine (0.66 mL, 6 mmol) in DMF (9 mL) under nitrogen, was added thionyl chloride (0.35 mL, 4.8 mmol) dropwise. There was a slight exotherm after which the mixture was stirred at 0°-5° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | CN(C)C=O | null | null | CCOc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OCC>CN(C)C=O>CCOc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2751c75ddf0c486a8d95a650128f9c7e | C/C=C\C.O.O=C1CCCCC1>>C1=CCOC2(CCCCC2)OC1 | C\C=C/C.C1(CCCCC1)=O.O>>C1CCCCC12OCC=CCO2 | [CH:1](=[CH:2]\[CH3:3])\[CH3:12].[OH2:11].[O:4]=[C:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH:1]1=[CH:2][CH2:3][O:4][C:5]2([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[O:11][CH2:12]1 | C/C=C\C.O.O=C1CCCCC1 | C1=CCOC2(CCCCC2)OC1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | a8e59b804e0a5a5ee2234051e1e76f1119fd05c6f713dec2babad68cb085ae6d | 6c57eaf115312957a9a907ba5f895cbf506b497e86f310f03cc08f79ec3ac645 | C1=CCOC2(CCCCC2)OC1 | [CH3;D1;+0:1]/[C:2]=[C:3]\[CH3;D1;+0:4].[C:5]-[C:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9]-[C:10].[OH2;D0;+0:11]>>[C:5]-[C:6]-[C;H0;D4;+0:7]1(-[C:9]-[C:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2]=[C:3]-[CH2;D2;+0:4]-[O;H0;D2;+0:8]-1 | 92 | [{"value": 92.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Cis-but-2-ene, 4-diol (50 g), cyclohexanone (50 g) and SNCA catalyst (2.5 g) were refluxed in benzene (75 ml) using a Deanstark water separator. The catalyst was filtered, the solvent evaporated and the residue distilled at 80°-85° C./4 torr to give 7,12-dioxaspiro[5,6]dodec-9-ene of formula III (92%) of the drawings.
... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ether.Ether | C1CCCCC1 | C1=CCOC2(CCCCC2)OC1 | C1=CCOC2(CCCCC2)OC1 | null | C1=CC=CC=C1 | null | null | C/C=C\C.O.O=C1CCCCC1>C1=CC=CC=C1>C1=CCOC2(CCCCC2)OC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68ed201820eb41f482bf2de3bfa7daba | O=CC1CCOC2(CCCCC2)OC1>>OCC1CCOC2(CCCCC2)OC1 | C(=O)C1COC2(CCCCC2)OCC1.[BH4-].[Na+]>>OCC1COC2(CCCCC2)OCC1 | [O:1]=[CH:2][CH:3]1[CH2:4][CH2:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[O:13][CH2:14]1>>[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[O:13][CH2:14]1 | O=CC1CCOC2(CCCCC2)OC1 | OCC1CCOC2(CCCCC2)OC1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | C1CCC2(CC1)OCCCCO2 | [#8:1]-[C:2]-[C:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6]>>[#8:1]-[C:2]-[C:3](-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6] | null | [] | 10 | CELSIUS | null | null | To a solution of 9-formyl-7, 12-dioxaspiro[5,6]dodecane of formula IV (5 g) in methanol (15 ml) was added in small portions NaBH4 (0.5 g) while stirring the solution and maintaining the temperature at 10° C. After complete addition, the reaction mixture was stirred for 3 hr at 20° C. The product residue obtained after ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | C1CCC2(CC1)OCCCCO2 | null | CO | 10 | null | O=CC1CCOC2(CCCCC2)OC1>CO>OCC1CCOC2(CCCCC2)OC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-41c36e816c8a49348cb7de1b22c2c650 | OCC1CCOC2(CCCCC2)OC1>>OCCC1COC2(CCCCC2)OC1 | O.OCC1COC2(CCCCC2)OCC1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>OCCC1COC2(CCCCC2)OC1 | [OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[O:13][CH2:14]1>>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:5][O:6][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[O:13][CH2:14]1 | OCC1CCOC2(CCCCC2)OC1 | OCCC1COC2(CCCCC2)OC1 | null | null | C1=CC=CC=C1 | Miscellaneous | OtherReaction | ab9c52a3476cf18303bd43755898a9308c36629ed14c627b72ab190f6929f44e | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | C1CCC2(CC1)OCCCO2 | [O;D1;H1:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[#8:5]-[C:6]-[#8:7]-[C:8]-[CH2;D2;+0:9]-1>>[O;D1;H1:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:9]1-[C:8]-[#8:7]-[C:6]-[#8:5]-[CH2;D2;+0:4]-1 | 70 | [{"value": 70.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 9-hydroxymethyl-7, 12-dioxaspiro[5,6]dodecane of the formula V (4 g) of the drawings in benzene (15 ml) was stirred at 10° C. for 5 hr with anhydrous p-toluenesulphonic acid (0.2 g). The reaction mixture was made alkaline by adding TEA and water. The benzene layer was separated and the aqueous layer extra... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | C1CCC2(CC1)OCCCCO2 | C1CCC2(CC1)OCCCO2 | C1CCC2(CC1)OCCCO2 | null | C1=CC=CC=C1 | null | null | OCC1CCOC2(CCCCC2)OC1>C1=CC=CC=C1>OCCC1COC2(CCCCC2)OC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f10081548cf4415e81c4b90bffd29a7a | C=CC(C)(C)O.CC[SiH](CC)CC>>CC[Si](CC)(CC)CCC(C)(C)O | CC(C=C)(C)O.C(C)[SiH](CC)CC>>CC(CC[Si](CC)(CC)CC)(C)O | [CH2:8]=[CH:9][C:10]([CH3:11])([CH3:12])[OH:13].[CH3:1][CH2:2][SiH:3]([CH2:4][CH3:5])[CH2:6][CH3:7]>>[CH3:1][CH2:2][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[CH2:8][CH2:9][C:10]([CH3:11])([CH3:12])[OH:13] | C=CC(C)(C)O.CC[SiH](CC)CC | CC[Si](CC)(CC)CCC(C)(C)O | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.C(CCC)O.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | C(CCC)O | Miscellaneous | OtherReaction | 6cc3f1eadda1112665613ad4e645127424bc2dc3fb86a0dd60a3ed530956e2e3 | 7be997182052ef72a2b91e5073ef9f506315a8ba0f0d67d5adf9938c2c0d61f5 | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[O;D1;H1:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C;D1;H3:7]-[C:8]-[SiH;D3;+0:9](-[C:10]-[C;D1;H3:11])-[C:12]-[C;D1;H3:13]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[O;D1;H1:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[Si;H0;D4;+0:9](-[C:8]-[C;D1;H3:7])(-[C:10]-[C;D1;H3:11])-[C:12]-[C;D1;H3:13] | 81.1 | [{"value": 81.1, "product": "CC(CC[Si](CC)(CC)CC)(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Into a four-necked 500 mL-flask equipped with a stirring apparatus, a thermometer and a dropping funnel, 81.2 g (0.943 mole) of 3-methyl-1-buten-3-ol and 0.2 g of an n-butanol solution containing chloroplatinic acid at a concentration of 2 weight % were charged, and they were heated to 80° C. with stirring. From the dr... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | Silyl protective group | null | null | null | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.C(CCC)O.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.C(CCC)O | 80 | null | C=CC(C)(C)O.CC[SiH](CC)CC>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.C(CCC)O.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.C(CCC)O>CC[Si](CC)(CC)CCC(C)(C)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-623e76f5d131438c908eae7b5ce8e7ac | C=CC(=O)O.COc1ccc(Br)cc1>>COc1ccc(C=CC(=O)O)cc1 | BrC1=CC=C(C=C1)OC.C(C=C)(=O)O.C(C)N(CC)CC>>COC1=CC=C(C=CC(=O)O)C=C1 | [CH2:7]=[CH:8][C:9](=[O:10])[OH:11].Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[CH:8][C:9](=[O:10])[OH:11])[cH:12][cH:13]1 | C=CC(=O)O.COc1ccc(Br)cc1 | COc1ccc(C=CC(=O)O)cc1 | null | Cl[Pd]Cl | O | C-C Coupling | Heck terminal vinyl | 55becfded1a3842d5a03bbf3e1610411c659aff0806930400c4db2ef61f9c87f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH2;D1;+0:6]=[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[C:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 81.2 | [{"value": 81.2, "product": "COC1=CC=C(C=CC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | p-bromo anisole (8.4 g), acrylic acid (3.9 g), water (13.5 g), PdCl2 (0.3 mg) and triethyamine (14.3 g, 89.3% pure by titration, the balance being water, recovered by phase separation from a previous run) were charged into an autoclave and heated for 2 hours at 130° C. The work up detailed in Example 1 gave 6.5 g (81%)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | Cl[Pd]Cl.O | 130 | null | C=CC(=O)O.COc1ccc(Br)cc1>Cl[Pd]Cl.O>COc1ccc(C=CC(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83277f5bcbe3453880c179fb06727b5a | CC(=O)OC(C)=O.O=C(O)c1ccc(O)cc1F>>CC(=O)Oc1ccc(C(=O)O)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1)O.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=CC(=C(C(=O)O)C=C1)F | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]([F:13])[cH:14]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]([F:13])[cH:14]1 | CC(=O)OC(C)=O.O=C(O)c1ccc(O)cc1F | CC(=O)Oc1ccc(C(=O)O)c(F)c1 | null | S(O)(O)(=O)=O | O | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 80 | CELSIUS | null | null | 4.3 Grams of 2-fluoro-4-hydroxybenzoic acid and 8.4 g of acetic anhydride were placed in a two-necked flask and mixed. While the mixture was cooled with water, 5 drops of sulfuric acid was added. After the heat generation ended, the mixture was heated at 80° C. for 30 minutes. Then, the reaction mixture was poured into... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | S(O)(O)(=O)=O.O | 80 | null | CC(=O)OC(C)=O.O=C(O)c1ccc(O)cc1F>S(O)(O)(=O)=O.O>CC(=O)Oc1ccc(C(=O)O)c(F)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2416e9807d124e3c9adcf5213d44dca1 | CCCCC[PH](=O)CCCCC.ClP(Cl)Cl>>CCCCCP(Cl)CCCCC | BrCCCCC.C(CCCC)P(CCCCC)=O.P(Cl)(Cl)Cl>>ClP(CCCCC)CCCCC | O=[PH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].ClP(Cl)[Cl:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][P:6]([Cl:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12] | CCCCC[PH](=O)CCCCC.ClP(Cl)Cl | CCCCCP(Cl)CCCCC | null | null | null | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | Cl-P(-Cl)-[Cl;H0;D1;+0:1].O=[PH;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6]>>[C:4]-[C:3]-[P;H0;D3;+0:2](-[Cl;H0;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | null | null | Following the procedure of Example 3, 1-bromopentane (181.2 g) was used as starting material to prepare di-n-pentylphosphine oxide (22.4 g), and this compound was further reacted with phosphorus trichloride to give chloro di-n-pentylphosphine, b.p. 88° C. at a pressure of 0.3 mm of mercury. This compound (10.4 g) was a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | HCl | null | null | null | CCCCC[PH](=O)CCCCC.ClP(Cl)Cl>>CCCCCP(Cl)CCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4e1b2e431c034625a9d3cefb9103c42d | CCCC(C)Br.CCCCOP(=O)([O-])OCCCC.CCC[CH](C)[Mg][Br]>>CCCC(C)[PH](=O)C(C)CCC | P(=O)(OCCCC)(OCCCC)[O-].BrC(C)CCC.[Mg].S(O)(O)(=O)=O.CC(CCC)[Mg]Br>>CC(CCC)P(C(C)CCC)=O | Br[CH:4]([CH2:3][CH2:2][CH3:1])[CH3:5].CCCCO[P:6](=O)(OCCCC)[O-:7].[Br][Mg][CH:8]([CH3:9])[CH2:10][CH2:11][CH3:12]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[PH:6](=[O:7])[CH:8]([CH3:9])[CH2:10][CH2:11][CH3:12] | CCCC(C)Br.CCCCOP(=O)([O-])OCCCC.CCC[CH](C)[Mg][Br] | CCCC(C)[PH](=O)C(C)CCC | null | null | O1CCCC1.C(C)OCC | Miscellaneous | OtherReaction | bc46d22f8fd7373712bd6257e5bb2db15253d0fdc7b45372c6127c408ee0ba3b | 1c6e19e36a4ffeed138891b863c1e8d9668014808d1141eef3237f611a831e96 | null | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].C-C-C-C-O-[P;H0;D4;+0:5](=O)(-[O-;H0;D1:6])-O-C-C-C-C.[Br]-[Mg]-[CH;D3;+0:7](-[C;D1;H3:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[CH;D3;+0:7](-[C;D1;H3:8])-[PH;D3;+0:5](=[O;H0;D1;+0:6])-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4] | 52.6 | [{"value": 52.6, "product": "CC(CCC)P(C(C)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 1 | HOUR | A Grignard solution prepared from 2-bromopentane (227.3 g, 1.5 moles) and magnesium (39.6 g) in tetrahydrofuran (500 cm3) was estimated by a standard procedure and found to contain 1.05 moles of 2-pentyl magnesium bromide. The solution was diluted with diethyl ether (250 cm3) and cooled to 10° C. in an atmosphere of ni... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Secondary halide | null | null | null | null | HBr.Mg | O1CCCC1.C(C)OCC | 10 | 1 | CCCC(C)Br.CCCCOP(=O)([O-])OCCCC.CCC[CH](C)[Mg][Br]>O1CCCC1.C(C)OCC>CCCC(C)[PH](=O)C(C)CCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e7d8772123ce4e13a0605b2c4b96576a | CCC[CH2][Mg][Cl].C[C](C)(C)[Mg][Cl].ClP(Cl)Cl>>CCCCP(Cl)C(C)(C)C | C(C)(C)(C)[Mg]Cl.P(Cl)(Cl)Cl.C(CCC)[Mg]Cl>>C(CCC)P(Cl)C(C)(C)C | [Cl][Mg][CH2:4][CH2:3][CH2:2][CH3:1].[Cl][Mg][C:7]([CH3:8])([CH3:9])[CH3:10].Cl[P:5](Cl)[Cl:6]>>[CH3:1][CH2:2][CH2:3][CH2:4][P:5]([Cl:6])[C:7]([CH3:8])([CH3:9])[CH3:10] | CCC[CH2][Mg][Cl].C[C](C)(C)[Mg][Cl].ClP(Cl)Cl | CCCCP(Cl)C(C)(C)C | null | null | C(C)OCC | Miscellaneous | OtherReaction | 448099601124fb8afc117e286cdaae18f0245af2a68c13e2e971c18b863f6b67 | 5b2a4af98860610907e140d97ebfaf696209e389093bac2abfdbece94c83a55f | null | Cl-[P;H0;D3;+0:1](-Cl)-[Cl;D1;H0:2].[C;D1;H3:3]-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[Mg]-[Cl].[C:7]-[C:8]-[CH2;D2;+0:9]-[Mg]-[Cl]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[P;H0;D3;+0:1](-[Cl;D1;H0:2])-[C;H0;D4;+0:4](-[C;D1;H3:3])(-[C;D1;H3:5])-[C;D1;H3:6] | null | [] | -25 | CELSIUS | 30 | MINUTE | To a solution of phosphorus trichloride (55 g) in dry diethyl ether (200 cm3) stirred and maintained at between -25° C. and -30° C. in an atmosphere of dry nitrogen a 2 molar solution of tert-butyl magnesium chloride in diethyl ether (200 cm3, solution supplied by Aldrich Chemical Co.) was added during 45 min. After a ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Magnesium halide | null | null | null | null | Mg | C(C)OCC | -25 | 0.5 | CCC[CH2][Mg][Cl].C[C](C)(C)[Mg][Cl].ClP(Cl)Cl>C(C)OCC>CCCCP(Cl)C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f09ba275a47d468cb9ceb88c522a8f48 | CC[CH](C)[Mg][Cl].C[C](C)(C)[Mg][Cl].ClP(Cl)Cl>>CCC(C)P(Cl)C(C)(C)C | C(C)(C)(C)[Mg]Cl.P(Cl)(Cl)Cl.CC(CC)[Mg]Cl>>CC(CC)P(Cl)C(C)(C)C | [Cl][Mg][CH:3]([CH2:2][CH3:1])[CH3:4].[Cl][Mg][C:7]([CH3:8])([CH3:9])[CH3:10].Cl[P:5](Cl)[Cl:6]>>[CH3:1][CH2:2][CH:3]([CH3:4])[P:5]([Cl:6])[C:7]([CH3:8])([CH3:9])[CH3:10] | CC[CH](C)[Mg][Cl].C[C](C)(C)[Mg][Cl].ClP(Cl)Cl | CCC(C)P(Cl)C(C)(C)C | null | null | C(C)OCC | Miscellaneous | OtherReaction | 448099601124fb8afc117e286cdaae18f0245af2a68c13e2e971c18b863f6b67 | 5b2a4af98860610907e140d97ebfaf696209e389093bac2abfdbece94c83a55f | null | Cl-[P;H0;D3;+0:1](-Cl)-[Cl;D1;H0:2].[C;D1;H3:3]-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[Mg]-[Cl].[C;D1;H3:7]-[C:8]-[CH;D3;+0:9](-[C;D1;H3:10])-[Mg]-[Cl]>>[C;D1;H3:3]-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[P;H0;D3;+0:1](-[Cl;D1;H0:2])-[CH;D3;+0:9](-[C;D1;H3:10])-[C:8]-[C;D1;H3:7] | null | [] | -25 | CELSIUS | 45 | MINUTE | To a solution of phosphorus trichloride (55 g) in dry diethyl ether (200 cm3) stirred and maintained at between -25° C. and -30° C. in an atmosphere of dry nitrogen, a 2 molar solution of tert-butyl magnesium chloride in diethyl ether (200 cm3, solution supplied by Aldrich Chemical Co.) was added during 45 min. After a... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Magnesium halide | null | null | null | null | Mg | C(C)OCC | -25 | 0.75 | CC[CH](C)[Mg][Cl].C[C](C)(C)[Mg][Cl].ClP(Cl)Cl>C(C)OCC>CCC(C)P(Cl)C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0308ebab0a1b4896a483600b07def253 | Cc1ccc(O)c(C)c1.S=P(Cl)(Cl)Cl>>Cc1ccc(OP(=S)(Cl)Oc2ccc(C)cc2C)c(C)c1 | P(=S)(Cl)(Cl)Cl.CC1=C(C=CC(=C1)C)O>>P(=S)(OC1=C(C=C(C=C1)C)C)(OC1=C(C=C(C=C1)C)C)Cl | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:19]([CH3:20])[cH:21]1.Cl[P:7](Cl)(=[S:8])[Cl:9]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][P:7](=[S:8])([Cl:9])[O:10][c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][c:17]2[CH3:18])[c:19]([CH3:20])[cH:21]1 | Cc1ccc(O)c(C)c1.S=P(Cl)(Cl)Cl | Cc1ccc(OP(=S)(Cl)Oc2ccc(C)cc2C)c(C)c1 | null | null | C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | bf12adbba621223d3feca21c5b95fc7ec55684e22bc36f75ac8bba03ce37ea71 | 212bb5eaccca98121639811e71e750c4cbfba99e07094c3a0cf2d1400ec85f5f | S=[PH](Oc1ccccc1)Oc1ccccc1 | Cl-[P;H0;D4;+0:1](-Cl)(-[Cl;D1;H0:2])=[S;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[Cl;D1;H0:2]-[P;H0;D4;+0:1](=[S;D1;H0:3])(-[#8:8]-[c:9])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 89.9 | [{"value": 89.9, "product": "P(=S)(OC1=C(C=C(C=C1)C)C)(OC1=C(C=C(C=C1)C)C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | Thiophosphoryl chloride (17.0 g) was dissolved in tuoluene (250 cm3) and triethylamine (21.5 g) was added. The solution was stirred at 20° C. and 2,4-dimethylphenol (24.4 g) was added in portions during 1 hr. The mixture was stirred for 2 hr. and then heated and stirred at 80° C. for a further 2 hr. and then cooled and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | null | c1ccccc1 | c1ccccc1.c1ccccc1 | null | C(C)N(CC)CC | 20 | null | Cc1ccc(O)c(C)c1.S=P(Cl)(Cl)Cl>C(C)N(CC)CC>Cc1ccc(OP(=S)(Cl)Oc2ccc(C)cc2C)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-edafaca1912e4767aa73ecb661b50df1 | C1CCOC1.CCOP(=S)(Cl)OCC.N.O=S(=O)(O)O>>CCOP(=O)(NP(=S)(OCC)OCC)OCC | P(=S)(OCC)(OCC)Cl.N.O1CCCC1.S(O)(O)(=O)=O>>O(P(OCC)(=S)NP(=O)(OCC)OCC)CC | O1[CH2:2][CH2:1][CH2:14][CH2:13]1.Cl[P:4]([O:3][CH2:10][CH3:11])(=[S:8])[O:15][CH2:16][CH3:17].[NH3:6].O=S(=[O:5])([OH:9])[OH:12]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([NH:6][P:7](=[S:8])([O:9][CH2:10][CH3:11])[O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17] | C1CCOC1.CCOP(=S)(Cl)OCC.N.O=S(=O)(O)O | CCOP(=O)(NP(=S)(OCC)OCC)OCC | null | null | ClCCl | Protection | OtherReaction | b1264ad81432c1a30deb65dcc866383e68d87c295b3970c5ce4335c14e69801b | e5a804eb0b1df43ecdb81750f9496bf5176f3accfd96a6411b341e34f9f5447f | null | Cl-[P;H0;D4;+0:1](=[S;H0;D1;+0:2])(-[#8:3]-[C:4])-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[C;D1;H3:7].O1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1.O=S(=[O;H0;D1;+0:12])(-[OH;D1;+0:13])-[OH;D1;+0:14].[NH3;D0;+0:15]>>[C:4]-[#8:3]-[P;H0;D4;+0:1](=[O;H0;D1;+0:12])(-[NH;D2;+0:15]-[#15:16](=[S;H0;D1;+0:2])(-[O;H0;D2;+... | null | [] | 65 | CELSIUS | 2 | HOUR | Diethyl chlorothiophosphate (25.04 g, supplied by Aldrich Chemical Company Ltd.) was added dropwise with stirring to a saturated solution of ammonia in tetrahydrofuran (250 cm3). Stirring was continued for two hr. The mixture was filtered to remove precipitated ammonium chloride and then concentrated by distillation of... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary amine | C1CCOC1 | null | null | HCl | ClCCl | 65 | 2 | C1CCOC1.CCOP(=S)(Cl)OCC.N.O=S(=O)(O)O>ClCCl>CCOP(=O)(NP(=S)(OCC)OCC)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4cdef75204d84d62a9005173b427b859 | CC[CH](C)[Mg][Cl].ClP(Cl)Cl>>CCC(C)P(Cl)C(C)CC | P(Cl)(Cl)Cl.CC(CC)[Mg]Cl>>CC(CC)P(Cl)C(C)CC | [Cl][Mg][CH:3]([CH2:2][CH3:1])[CH3:4].Cl[P:5](Cl)[Cl:6]>>[CH3:1][CH2:2][CH:3]([CH3:4])[P:5]([Cl:6])[CH:7]([CH3:8])[CH2:9][CH3:10] | CC[CH](C)[Mg][Cl].ClP(Cl)Cl | CCC(C)P(Cl)C(C)CC | null | null | C(C)OCC | C-C Coupling | OtherReaction | ed6fb77c42e402438fb059abb66e2fd1d9dd9b973de8deccb8fe05f61ee9052c | 8bca8ca721f0288f0875e75b7f264133e86623956746bda21982177c5da407f2 | null | Cl-[P;H0;D3;+0:1](-Cl)-[Cl;D1;H0:2].[C;D1;H3:3]-[C:4]-[CH;D3;+0:5](-[C;D1;H3:6])-[Mg]-[Cl]>>[C:7]-[C:8](-[C;D1;H3:9])-[P;H0;D3;+0:1](-[Cl;D1;H0:2])-[CH;D3;+0:5](-[C;D1;H3:6])-[C:4]-[C;D1;H3:3] | null | [] | null | null | null | null | In the manner of Examples 6 and 7, 2-butyl magnesium chloride (800 cm3 of a 2M solution in diethyl ether supplied by Aldrich Chemical Co.) was reacted with phosphorus trichloride (110 g) in diethyl ether (450 cm3) to give di-2-butylchlorophosphine (77.8 g, b.p. 84° C. at a pressure of 15 mm of mercury), and this compou... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide | null | null | null | null | null | C(C)OCC | null | null | CC[CH](C)[Mg][Cl].ClP(Cl)Cl>C(C)OCC>CCC(C)P(Cl)C(C)CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-94ebb151cdce429fa9a1e76ab6551460 | Cc1cc(Cl)ccc1O.NP(N)(N)=S.S=P(Cl)(Cl)Cl.[O-]P([O-])(=S)Cl>>Cc1cc(Cl)ccc1OP(=O)(NP(=S)(Oc1ccc(Cl)cc1C)Oc1ccc(Cl)cc1C)Oc1ccc(Cl)cc1C | ClC1=CC(=C(C=C1)O)C.[H-].[Na+].P(=S)(N)(N)N.N.P(=S)(Cl)(Cl)Cl.[H-].[Na+].P(=S)([O-])([O-])Cl.P(=S)(N)(N)N>>O(P(OC1=C(C=C(C=C1)Cl)C)(=S)NP(=O)(OC1=C(C=C(C=C1)Cl)C)OC1=C(C=C(C=C1)Cl)C)C1=C(C=C(C=C1)Cl)C | [CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[OH:9].N[P:13](N)([NH2:12])=[S:14].S=P(Cl)([Cl:20])[Cl:38].S=[P:10]([O-:11])([O-:15])[Cl:29]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[O:9][P:10](=[O:11])([NH:12][P:13](=[S:14])([O:15][c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]1[CH3:23])[O:24][c:25]1[cH:... | Cc1cc(Cl)ccc1O.NP(N)(N)=S.S=P(Cl)(Cl)Cl.[O-]P([O-])(=S)Cl | Cc1cc(Cl)ccc1OP(=O)(NP(=S)(Oc1ccc(Cl)cc1C)Oc1ccc(Cl)cc1C)Oc1ccc(Cl)cc1C | null | null | C1(=CC=CC=C1)C.CCCCCC.CCOCC.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | fbc357d27ff55096b0900ea3c41337d8d576fb2aada92aa1cf54f0c27217023d | 207ba4347e7ae3f1de3e65e474b89eab295dfec83cd096679dca90feff0c43f0 | O=P(NP(=S)(Oc1ccccc1)Oc1ccccc1)(Oc1ccccc1)Oc1ccccc1 | Cl-P(=S)(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].N-[P;H0;D4;+0:3](-N)(-[NH2;D1;+0:4])=[S;D1;H0:5].S=[P;H0;D4;+0:6](-[Cl;H0;D1;+0:7])(-[O-;H0;D1:8])-[O-;H0;D1:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[Cl;H0;D1;+0:7]-[c:14](:[c:15]):[c:16].[Cl;H0;D1;+0:2]-[c:17](:[c:18]):[c:19].[Cl;H0;D1;+0:1]-[c:20]1:[c:21]:[c:22]:[c:23](-[O;... | null | [] | null | null | 3 | HOUR | 4-chloro-2-methylphenol (142.5 g) was dissolved in a mixture of hexane (200 cm3) and toluene (400 cm3) and sodium hydride (30.0 g of 80% suspension in mineral oil) was added. After stirring for 3 hrs, this suspension was added during 2 hr to a stirred solution of thiophosphoryl chloride (84.5 g) in hexane (100 cm3). Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Primary amine.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide.Secondary amine | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C.CCCCCC.CCOCC.O1CCCC1 | null | 3 | Cc1cc(Cl)ccc1O.NP(N)(N)=S.S=P(Cl)(Cl)Cl.[O-]P([O-])(=S)Cl>C1(=CC=CC=C1)C.CCCCCC.CCOCC.O1CCCC1>Cc1cc(Cl)ccc1OP(=O)(NP(=S)(Oc1ccc(Cl)cc1C)Oc1ccc(Cl)cc1C)Oc1ccc(Cl)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6780bd14b0b34526b70c2eaf4a175924 | Cc1ccc(C(C)C)c(O)c1.S=P(Cl)(Cl)Cl>>Cc1ccc(C(C)C)c(OP(=S)(Cl)Oc2cc(C)ccc2C(C)C)c1 | C(C)(C)C1=C(C=C(C=C1)C)O.[H-].[Na+].P(=S)(Cl)(Cl)Cl>>P(=S)(OC1=C(C=CC(=C1)C)C(C)C)(OC1=C(C=CC(=C1)C)C(C)C)Cl | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([CH3:7])[CH3:18])[c:9]([OH:10])[cH:25]1.Cl[P:11](Cl)(=[S:12])[Cl:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][P:11](=[S:12])([Cl:13])[O:14][c:15]2[cH:16][c:17]([CH3:18])[cH:19][cH:20][c:21]2[CH:22]([CH3:23])[CH3:24])[cH:25]1 | Cc1ccc(C(C)C)c(O)c1.S=P(Cl)(Cl)Cl | Cc1ccc(C(C)C)c(OP(=S)(Cl)Oc2cc(C)ccc2C(C)C)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | bf12adbba621223d3feca21c5b95fc7ec55684e22bc36f75ac8bba03ce37ea71 | 212bb5eaccca98121639811e71e750c4cbfba99e07094c3a0cf2d1400ec85f5f | S=[PH](Oc1ccccc1)Oc1ccccc1 | Cl-[P;H0;D4;+0:1](-Cl)(-[Cl;D1;H0:2])=[S;D1;H0:3].[C;D1;H3:4]-[CH;D3;+0:5](-[CH3;D1;+0:6])-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:4]-[CH;D3;+0:5](-[C;D1;H3:12])-[c:7](:[c:8]):[c:9](-[O;H0;D2;+0:10]-[P;H0;D4;+0:1](-[Cl;D1;H0:2])(=[S;D1;H0:3])-[#8:13]-[c:14]:[c:15]:[c:16](-[CH3;D1;+0:6]):[c:17]):[c:11] | 63 | [{"value": 63.0, "product": "P(=S)(OC1=C(C=CC(=C1)C)C(C)C)(OC1=C(C=CC(=C1)C)C(C)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-isopropyl-5-methylphenol was reacted with sodium hydride and thiophosphoryl chloride using the procedure of Example 21 to form bis(2-isopropyl-5-methylphenyl) chlorothiophosphate (31PNMR, singlet, 57 ppm). This compound was reacted with diphenylphosphonothioic amide by the General Method C(ii) (THF) yielding the comp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | null | c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | Cc1ccc(C(C)C)c(O)c1.S=P(Cl)(Cl)Cl>>Cc1ccc(C(C)C)c(OP(=S)(Cl)Oc2cc(C)ccc2C(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-49348a03da5449a3a6fa1f38365b6d60 | CC(=O)Cl.Cc1ccc2c(C(C)CCO)ccc(C(C)C)cc1-2>>CC(=O)OCCC(C)c1ccc(C(C)C)cc2c(C)ccc1-2 | C(C)(=O)Cl.C(C)(C)C1=CC=C(C2=CC=C(C2=C1)C)C(CCO)C.N1=CC=CC=C1>>C(C)(=O)OCCC(C)C=1C2=CC=C(C2=CC(=CC1)C(C)C)C | Cl[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][CH:7]([CH3:8])[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[c:18]([CH3:19])[cH:20][cH:21][c:22]1-2>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH:7]([CH3:8])[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[c:18]([CH3:19])[cH:20][cH:21][c:... | CC(=O)Cl.Cc1ccc2c(C(C)CCO)ccc(C(C)C)cc1-2 | CC(=O)OCCC(C)c1ccc(C(C)C)cc2c(C)ccc1-2 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccc2cccc-2cc1 | Cl-[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 | 1 | HOUR | 4.8 g (0.063 mol) of acetyl chloride in 20 ml of dichloromethane were added dropwise at 0° C. to a solution of 12.1 g (0.05 mol) of 3-(7-isopropyl-1-methylazulen-4-yl)butanol and 7.9 g (0.1 mol) of pyridine in 100 ml of dichloromethane, and the mixture was stirred at room temperature for 1 hour. It was then extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccc2cccc2cc1 | HCl | ClCCl | null | 1 | CC(=O)Cl.Cc1ccc2c(C(C)CCO)ccc(C(C)C)cc1-2>ClCCl>CC(=O)OCCC(C)c1ccc(C(C)C)cc2c(C)ccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f7d58edbb5e54cc089f19cc68f88af86 | C/C=C/C(=O)Cl.CCN(CC)CC.Cc1ccc2c(C(C)CCO)ccc(CC(C)C)cc1-2>>C=CCCC(=O)OCCC(C)c1ccc(CC(C)C)cc2c(C)ccc1-2 | O.C(\C=C\C)(=O)Cl.C(C(C)C)C1=CC=C(C2=CC=C(C2=C1)C)C(CCO)C.C(C)N(CC)CC>>C(CC=C)C(=O)OCCC(C)C=1C2=CC=C(C2=CC(=CC1)CC(C)C)C | Cl[C:5](/[CH:4]=[CH:3]/[CH3:2])=[O:6].CCN(CC)C[CH3:1].[OH:7][CH2:8][CH2:9][CH:10]([CH3:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[cH:20][c:21]2[c:22]([CH3:23])[cH:24][cH:25][c:26]1-2>>[CH2:1]=[CH:2][CH2:3][CH2:4][C:5](=[O:6])[O:7][CH2:8][CH2:9][CH:10]([CH3:11])[c:12]1[cH:13][cH:14][c:15]([CH2:16... | C/C=C/C(=O)Cl.CCN(CC)CC.Cc1ccc2c(C(C)CCO)ccc(CC(C)C)cc1-2 | C=CCCC(=O)OCCC(C)c1ccc(CC(C)C)cc2c(C)ccc1-2 | null | null | O1CCCC1 | Acylation | OtherReaction | 342207de4c335b59324a35212f1f158240c295dd2d150892d3db08d21b0f5356 | 40fdba0dae1a5a857a281d8885f2ac044c84690ddfd78f39e9253756e50a80a4 | c1ccc2cccc-2cc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[C;H0;D3;+0:2](=[O;D1;H0:3])/[CH;D2;+0:4]=[CH;D2;+0:5]/[CH3;D1;+0:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH;D2;+0:6]=[CH2;D1;+0:1] | null | [] | null | null | 2 | HOUR | 10.0 g (0.07 mol) of crotonyl chloride were added dropwise at room temperature to a solution of 7.26 g (0.03 mol) of 3-(7-isobutyl-1-methylazulen-4-yl)butanol and 30 ml of triethylamine in 100 ml of tetrahydrofuran, and the mixture was stirred for 2 hours. 50 ml of water were then added, and the batch was thoroughly st... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol.Tertiary amine | Ester.Allyl | null | null | c1ccc2cccc2cc1 | HCl | O1CCCC1 | null | 2 | C/C=C/C(=O)Cl.CCN(CC)CC.Cc1ccc2c(C(C)CCO)ccc(CC(C)C)cc1-2>O1CCCC1>C=CCCC(=O)OCCC(C)c1ccc(CC(C)C)cc2c(C)ccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7d6fec5e6d54cc5b295691760de5f99 | CC(=O)OC(C)C(=O)N1c2ccccc2C(C)CC1(C)C>>CC1CC(C)(C)c2cccc(N)c21 | N.C(C)(=O)[O-].C(C)(=O)OC(C(=O)N1C(CC(C2=CC=CC=C12)C)(C)C)C.OS(=O)(=O)O>>NC1=C2C(CC(C2=CC=C1)(C)C)C | CC(=O)OC(C)C(=O)[N:12]1[C:4]([CH3:5])([CH3:6])[CH2:3][CH:2]([CH3:1])[c:13]2[cH:7][cH:8][cH:9][cH:10][c:11]21>>[CH3:1][CH:2]1[CH2:3][C:4]([CH3:5])([CH3:6])[c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[c:13]21 | CC(=O)OC(C)C(=O)N1c2ccccc2C(C)CC1(C)C | CC1CC(C)(C)c2cccc(N)c21 | null | null | C(C)(=O)O.O | Functional Group Interconversion | OtherReaction | 751b997eceb2879c79880df7df2a573ebf671ecfbfe066920fb5ebb1bc6a5f31 | 63989af454af4021ebf3b6c605c13acad5bf9e2283cf20379910b86126ac543d | c1ccc2c(c1)CCC2 | C-C(-O-C(-C)=O)-C(=O)-[N;H0;D3;+0:1]1-[c:2]2:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:2-[C:8]-[C:9]-[C;H0;D4;+0:10]-1(-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:11]-[C;H0;D4;+0:10]1(-[C;D1;H3:12])-[C:9]-[C:8]-[c:7]2:[c:2](-[NH2;D1;+0:1]):[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:2-1 | 75 | [{"value": 69.0, "product": "NC1=C2C(CC(C2=CC=C1)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "NC1=C2C(CC(C2=CC=C1)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | The acetate compound prepared in B (ii) (55 g, GC purity 91%, 0.172 moles) was added over 45 minutes to 98% H2SO4 (50 ml) at 25°-60° C. (exotherm). After stirring for a further 30 minutes at 60° C., water (50 ml) containing acetic acid (10 ml) was cautiously added dropwise and the mixture heated at 100° C. for 3 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Primary amine | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(C)(=O)O.O | 60 | 0.5 | CC(=O)OC(C)C(=O)N1c2ccccc2C(C)CC1(C)C>C(C)(=O)O.O>CC1CC(C)(C)c2cccc(N)c21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5330fe2873fa4dd296b870c5f2f16b19 | CCCCC[C@H]1[C@@H](CC(=O)O)CC[C@H]1O>>CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O | O[C@H]1[C@H]([C@H](CC1)CC(=O)O)CCCCC.[N+](=[N-])=C>>O[C@H]1[C@H]([C@H](CC1)CC(=O)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:7]([CH2:8][C:9](=[O:10])[OH:11])[CH2:13][CH2:14][C@H:15]1[OH:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:7]([CH2:8][C:9](=[O:10])[O:11][CH3:12])[CH2:13][CH2:14][C@H:15]1[OH:16] | CCCCC[C@H]1[C@@H](CC(=O)O)CC[C@H]1O | CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O | null | null | CCOCC | Miscellaneous | OtherReaction | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | C1CCCC1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;D1;H3:5] | null | [] | null | null | null | null | It is to be noted that (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid, used as starting product in this variant of the process of the invention, can also be directly methylated, for example by reacting it with an excess of diazomethane in ether solution, to provide pratically pure methyl (+)-(1R,2S,3R)-3-h... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | C1CCCC1 | Other | CCOCC | null | null | CCCCC[C@H]1[C@@H](CC(=O)O)CC[C@H]1O>CCOCC>CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9351ff791ece43d89068d7c5e43ad1d4 | CCO.CCO.C[C@H](N)c1ccccc1.O=C(O)C(O)C(O)C(=O)O>>CCCCC[C@H]1[C@@H](CC(=O)O)CC[C@H]1O.CCCCC[C@H]1[C@@H](CC(=O)[O-])CC[C@H]1O.C[C@H]([NH3+])c1ccccc1 | C1(=CC=CC=C1)[C@H](C)N.C(C)O.C(C)O.C(C(C(=O)O)O)(C(=O)O)O>>O[C@H]1[C@H]([C@H](CC1)CC(=O)[O-])CCCCC.C1(=CC=CC=C1)[C@H](C)[NH3+].O[C@H]1[C@H]([C@H](CC1)CC(=O)O)CCCCC | O[CH2:19][CH3:20].[CH3:16][CH2:17][OH:30].[CH3:31][C@H:32]([NH2:33])[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1.O[CH:3]([CH:2]([C:1](=[O:10])[OH:11])[OH:15])[C:24](=[O:25])[OH:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:7]([CH2:8][C:9](=[O:10])[OH:11])[CH2:12][CH2:13][C@H:14]1[OH:15].[CH3:16][CH2:17][CH2:18][... | CCO.CCO.C[C@H](N)c1ccccc1.O=C(O)C(O)C(O)C(=O)O | CCCCC[C@H]1[C@@H](CC(=O)O)CC[C@H]1O.CCCCC[C@H]1[C@@H](CC(=O)[O-])CC[C@H]1O.C[C@H]([NH3+])c1ccccc1 | null | null | null | Acylation | OtherReaction | de2ad0bd7c39560a69b3b3d1fe2cfe0e1edce6eb87dd7e51b82c0953a8dd5326 | feccad8295f640ff4fd9de21f05c157d1cf018b16fa25ae9bb222c8953cc88e2 | C1CCCC1.C1CCCC1.c1ccccc1 | O-[CH2;D2;+0:1]-[CH3;D1;+0:2].O-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[CH;D3;+0:7](-[OH;D1;+0:8])-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[OH;D1;+0:11].[C;D1;H3:12]-[CH2;D2;+0:13]-[OH;D1;+0:14].[C;D1;H3:15]-[C:16](-[NH2;D1;+0:17])-[c:18]>>[C;D1;H3:15]-[C:16](-[NH3+;D1:17])-[c:18].[C:19]-[C:20](-[OH;D1;+0:14... | null | [] | null | null | null | null | This acid presented the analytical characters of the racemic acid described under b) and a [α]20D =-12° (c=1.15, ethanol) (purity: 99%; e.r. 99.2:0.8). Proceeding in a manner analogous to that described here-above, but using (-)-(S)-1-penylethylamine (Fluka purum; e.r. 98:2), there was obtained (1R,2S,3R)-3-hydroxy-2-p... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Primary amine | Carboxylic acid.Secondary alcohol.Secondary alcohol | null | C1CCCC1.C1CCCC1 | C1CCCC1.C1CCCC1.c1ccccc1 | null | null | null | null | CCO.CCO.C[C@H](N)c1ccccc1.O=C(O)C(O)C(O)C(=O)O>>CCCCC[C@H]1[C@@H](CC(=O)O)CC[C@H]1O.CCCCC[C@H]1[C@@H](CC(=O)[O-])CC[C@H]1O.C[C@H]([NH3+])c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a0652456c8c14b52877012b598e65bcc | CCCCCC1=C(CC(=O)O)CCC1=O>>CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)O | O=C1C(=C(CC1)CC(=O)O)CCCCC.C(Cl)Cl.C(C)N(CC)CC>>O=C1[C@H]([C@H](CC1)CC(=O)O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1=[C:11]([CH2:12][C:13](=[O:14])[OH:15])[CH2:10][CH2:9][C:7]1=[O:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@@H:11]1[CH2:12][C:13](=[O:14])[OH:15] | CCCCCC1=C(CC(=O)O)CCC1=O | CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)O | null | null | CO | Reduction | Hydrogenation (double to single) | 86ab11674f5c386e6bf85e3207d59c3e1c24536199ef80ba4c93b215304815db | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1CCCC1 | [C:1]-[C:2]-[C;H0;D3;+0:3]1=[C;H0;D3;+0:4](-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8])-[C:9]-[C:10]-[C:11]-1=[O;D1;H0:12]>>[C:1]-[C:2]-[C@@H;D3;+0:3]1-[C:11](=[O;D1;H0:12])-[C:10]-[C:9]-[C@@H;D3;+0:4]-1-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | null | [] | null | null | 5 | MINUTE | Into a Schlenk type vessel, kept anhydrous and under Ar, there was injected the precatalytic solution (6.75 ml) containing 47 mg (0.05 mmole) of bis(trifluoro-acetato)[(+)-(R)-2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl]ruthenium (II), 3-oxo-2-pentyl-1-cyclopentene-1-acetic acid (0.5 g, 2.4 mmole), CH2Cl2 (5 ml), meth... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | CO | null | 0.083333 | CCCCCC1=C(CC(=O)O)CCC1=O>CO>CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5e5ea1bad7f34a958fa0ed6555062f7d | CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O>>CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)OC | O[C@H]1[C@H]([C@H](CC1)CC(=O)OC)CCCCC.C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl.C(C)(=O)[O-].[Na+]>>O=C1[C@H]([C@H](CC1)CC(=O)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]1[C@H:7]([OH:8])[CH2:9][CH2:10][C@@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O | CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)OC | null | null | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 6ad3a11b438c0e1c50a70c6d16bbab7d61c75949455edc72e81522617519349d | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCC1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[C@H;D3;+0:6]-1-[OH;D1;+0:7]>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6]-1=[O;H0;D1;+0:7] | 94.9 | [{"value": 92.7, "product": "O=C1[C@H]([C@H](CC1)CC(=O)OC)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "O=C1[C@H]([C@H](CC1)CC(=O)OC)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This ester (2.85 g) was then oxidized by means of PCC, in the presence of sodium acetate, in a manner analogous to the method described in Example 1 d), to yield 2.68 g of the desired methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (colorless oil; purity 98.5%; yield 92.7%).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCCC1 | C1CCCC1 | C1CCCC1 | null | null | null | null | CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O>>CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4de432ae17d04f5487e4f075f169e736 | CCCCC[C@@H]1[C@H](CC(=O)OC)CC[C@@H]1O>>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | O[C@@H]1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC>>O=C1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:7]([OH:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCC[C@@H]1[C@H](CC(=O)OC)CC[C@@H]1O | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | null | null | CO | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 6ad3a11b438c0e1c50a70c6d16bbab7d61c75949455edc72e81522617519349d | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCC1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[C@@H;D3;+0:6]-1-[OH;D1;+0:7]>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6]-1=[O;H0;D1;+0:7] | null | [] | null | null | null | null | The intermediate methyl (-)-(1S,2R,3S)-3-hydroxy-2-pentyl-1-cyclopentane acetate presented a [α]20D =-16° (c=1.805, methanol)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCCC1 | C1CCCC1 | C1CCCC1 | null | CO | null | null | CCCCC[C@@H]1[C@H](CC(=O)OC)CC[C@@H]1O>CO>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c559e57f319541fc972edd30a8da1304 | CCCCCC1=C(CC(=O)O)CCC1=O.CCN(CC)CC>>CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)OC | O=C1C(=C(CC1)CC(=O)O)CCCCC.C(C)N(CC)CC.[H][H]>>O=C1[C@H]([C@H](CC1)CC(=O)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1=[C:11]([CH2:12][C:13](=[O:14])[OH:15])[CH2:10][CH2:9][C:7]1=[O:8].CCN(CC)C[CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCCC1=C(CC(=O)O)CCC1=O.CCN(CC)CC | CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)OC | null | null | C1CCOC1.CO | Heteroatom Alkylation and Arylation | OtherReaction | da196e3236d736556fdcfb1837b2770790986d12ec118891fa08f19c2fb48760 | 1780374e34072fe6cc492484130d27a3000ef633f8afc7bcab57f8989bcf035e | O=C1CCCC1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].[C:2]-[C:3]-[C;H0;D3;+0:4]1=[C;H0;D3;+0:5](-[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9])-[C:10]-[C:11]-[C:12]-1=[O;D1;H0:13]>>[C:2]-[C:3]-[C@@H;D3;+0:4]1-[C:12](=[O;D1;H0:13])-[C:11]-[C:10]-[C@@H;D3;+0:5]-1-[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH3;D1;+0:1] | null | [] | null | null | 4 | HOUR | To a solution of 252 mg (1.20 mmole) 3-oxo-2-pentyl-1 cyclopentene-1-acetic acid, in a mixture of 7 ml of THF and 21 ml of methanol, there were added 2 ml of the catalyst solution obtained in a) (0.025 mmole, 0.021 eq.) and 10.4 μl of triethylamine (0.075 mmole, 3 eq.) under stirring at r.t. This solution, prepared in ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Tertiary amine | Ketone.Ester | C1=CCCC1 | C1CCCC1 | C1CCCC1 | Other | C1CCOC1.CO | null | 4 | CCCCCC1=C(CC(=O)O)CCC1=O.CCN(CC)CC>C1CCOC1.CO>CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13f0bb09496b4e76add90df9bebc924b | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)O.COC(=O)OC(=O)OC>>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | O=C1[C@@H]([C@@H](CC1)CC(=O)O)CCCCC.C(=O)(OC)OC(=O)OC>>O=C1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][C:13](=[O:14])[OH:15].COC(=O)OC(=O)O[CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)O.COC(=O)OC(=O)OC | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | ab70ccb44fd2770c6bb4cd50876c98fd63fd5433f67c38378b2c3cf9fd8e3bb7 | 98c84e009887ebe0ace192c2ccbdd6041fa48ce8e27f6f302e5a3939fc247f0b | O=C1CCCC1 | C-O-C(=O)-O-C(=O)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 90 | [{"value": 90.0, "product": "O=C1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 104 Mg (0.49 mmole) of (+)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid (97:3 cis/trans ratio) in 0.5 ml of methanol were treated with 76 μl of dimethyl dicarbonate [CH3O(CO)O(CO)OCH3, origin: Bayer; 96 mg, 0.72 mmole, 1.5 eq.]. The resulting solution was heated to 45° during 16 h and then evaporated under vacuum. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Carboxylic acid | Ester | null | null | C1CCCC1 | HO- | CO | null | null | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)O.COC(=O)OC(=O)OC>CO>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cb6326117e3045cb93e4c9a0471e9b58 | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)O.COS(=O)(=O)OC>>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | CCOCC.COS(=O)(=O)OC.O=C1[C@@H]([C@@H](CC1)CC(=O)O)CCCCC>>O=C1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][C:13](=[O:14])[OH:15].COS(=O)(=O)O[CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)O.COS(=O)(=O)OC | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | O=C1CCCC1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 89.8 | [{"value": 84.0, "product": "O=C1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "O=C1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 104 mg (0.49 mmole) of (±)cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid (93:7 cis/trans ratio) in 1 ml of (CH3)2CO there were added, first 56 μl of (CH3)2SO4 (74 ml, 0.59 mmole, 1.2 eq.) and then 81 mg (0.59 mmole, 1.2 eq.) of anhydrous solid K2 CO3. The resulting suspension was heated at r.t. during 4 h and taken in... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | C1CCCC1 | HO- | O.CC(=O)C | null | null | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)O.COS(=O)(=O)OC>O.CC(=O)C>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-796c9df1b95145c8a5bab3faf51eb692 | CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O>>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | O[C@H]1[C@H]([C@H](CC1)CC(=O)OC)CCCCC>>O=C1[C@@H]([C@@H](CC1)CC(=O)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]1[C@H:7]([OH:8])[CH2:9][CH2:10][C@@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O | CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC | null | null | CO | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 6ad3a11b438c0e1c50a70c6d16bbab7d61c75949455edc72e81522617519349d | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCC1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[C@H;D3;+0:6]-1-[OH;D1;+0:7]>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6]-1=[O;H0;D1;+0:7] | null | [] | null | null | null | null | methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate, characterized by a [α]20D superior to +17° (c=1.795 g/ 100 ml, methanol).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCCC1 | C1CCCC1 | C1CCCC1 | null | CO | null | null | CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O>CO>CCCCC[C@H]1C(=O)CC[C@H]1CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d6f1159968164ca59973a165fcea56a0 | COC(=O)c1ccc2cc(C(=O)OC)ccc2c1>>O=C(O)c1ccc2cc(C(=O)O)ccc2c1 | COC(=O)C1=CC2=CC=C(C=C2C=C1)C(=O)OC.COC(=O)C1=CC2=CC=C(C=C2C=C1)C(=O)OC>>C1=C(C=CC2=CC(=CC=C12)C(=O)O)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[O:12]C)[cH:13][cH:14][c:15]2[cH:16]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]2[cH:16]1 | COC(=O)c1ccc2cc(C(=O)OC)ccc2c1 | O=C(O)c1ccc2cc(C(=O)O)ccc2c1 | null | [Cr].[Co] | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc2ccccc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | null | [] | null | null | null | null | Dimethyl-2,6-naphthalenedicarboxylate was hydrolyzed at elevated temperatures and elevated pressures in the batch-mode in a stirred, 300 ml Hastelloy C autoclave reactor. 37.5 Grams of dimethyl-2,6-naphthalenedicarboxylate were charged to the reactor. No catalyst was used. The 2,6-NDA product was separated from the mot... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccc2ccccc2c1 | Other | [Cr].[Co] | null | null | COC(=O)c1ccc2cc(C(=O)OC)ccc2c1>[Cr].[Co]>O=C(O)c1ccc2cc(C(=O)O)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-558175fef481481a9e6bb6eb3ef92dfd | COC(=O)c1ccc2cc(C(=O)OC)ccc2c1>>O=C(O)c1ccc2cc(C(=O)O)ccc2c1 | COC(=O)C1=CC2=CC=C(C=C2C=C1)C(=O)OC>>C1=C(C=CC2=CC(=CC=C12)C(=O)O)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[O:12]C)[cH:13][cH:14][c:15]2[cH:16]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]2[cH:16]1 | COC(=O)c1ccc2cc(C(=O)OC)ccc2c1 | O=C(O)c1ccc2cc(C(=O)O)ccc2c1 | null | [Ti] | null | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc2ccccc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | null | [] | null | null | null | null | The hydrolysis of dimethyl-2,6-naphthalenedicarboxylate was conducted in the batch-mode in a 2 liter, stirred, titanium-lined reactor. The reaction time, temperature, pressure and analysis of the resulting 2,6-naphthalenedicarboxylic acid are provided in Table 5.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccc2ccccc2c1 | Other | [Ti] | null | null | COC(=O)c1ccc2cc(C(=O)OC)ccc2c1>[Ti]>O=C(O)c1ccc2cc(C(=O)O)ccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-82f26f3da9b94277b41d5e2a0b568816 | O=[N+]([O-])c1ccccc1S(=O)(=O)Cl.[OH-].[OH-]>>Nc1ccc(-c2ccc(N)c(S(=O)(=O)O)c2)cc1S(=O)(=O)O | Cl.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl.[OH-].[Na+].[OH-].[Na+]>>NC1=C(C=C(C=C1)C1=CC(=C(C=C1)N)S(=O)(=O)O)S(=O)(=O)O | Cl[S:12]([c:11]1[c:9]([N+:1]([O-:15])=[O:21])[cH:2][cH:5][cH:6][cH:16]1)(=[O:13])=[O:14].[OH-:20].[OH-:22]>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:11]([S:12](=[O:13])(=[O:14])[OH:15])[cH:16]2)[cH:17][c:18]1[S:19](=[O:20])(=[O:21])[OH:22] | O=[N+]([O-])c1ccccc1S(=O)(=O)Cl.[OH-].[OH-] | Nc1ccc(-c2ccc(N)c(S(=O)(=O)O)c2)cc1S(=O)(=O)O | null | [Zn] | null | Aromatic Heterocycle Formation | OtherReaction | 2ddb7c090d049d9b01b596b1c5531306ec590605e5521218aaf87a1a76a70d6e | b985031033afe35c77179a62d23d1deb378f8cb143d9567147a092876a6f49a9 | c1ccc(-c2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9]:1-[N+;H0;D3:10](-[O-;H0;D1:11])=[O;H0;D1;+0:12].[OH-;D0:13].[OH-;D0:14]>>[N;D1;H2:15]-[c;H0;D3;+0:9]1:[c:16]:[c:17]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7]2:[c:18]:[c:19](-[#16:20](=[O;H0;D1;+0:13])(=[O;H0;D1;+0:12])... | 28.6 | [{"value": 28.6, "product": "NC1=C(C=C(C=C1)C1=CC(=C(C=C1)N)S(=O)(=O)O)S(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.2, "product": "NC1=C(C=C(C=C1)C1=CC(=C(C=C1)N)S(=O)(=O)O)S(=O)(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | A 500 mL flask equipped with mechanical stirrer, condenser, addition funnel, and thermometer was charged with 50.0 g (0.255 mol) of 2-nitrobenzene sulfonyl chloride (Aldrich). Upon dropwise addition of 5M aqueous sodium hydroxide (125 mL, 0.625 mol) the reaction mixture warmed to 80° C. and a dark red/brown solution re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Sulfonyl halide | Primary amine.Primary amine.Sulfonic acid.Sulfonic acid | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | [Zn] | 80 | 1 | O=[N+]([O-])c1ccccc1S(=O)(=O)Cl.[OH-].[OH-]>[Zn]>Nc1ccc(-c2ccc(N)c(S(=O)(=O)O)c2)cc1S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-07ac67ae638344aebabaeb810563c749 | O=C(NC(CO)CO)c1c(I)c(O)c(I)c(C(=O)NC(CO)CO)c1I>>C[C@H](Oc1c(I)c(C(=O)NC(CO)CO)c(I)c(C(=O)NC(CO)CO)c1I)C(N)=O | [Na].OCC(CO)NC(=O)C1=C(C(=C(C(=C1I)O)I)C(=O)NC(CO)CO)I>>NC([C@@H](OC=1C(=C(C(=C(C1I)C(=O)NC(CO)CO)I)C(=O)NC(CO)CO)I)C)=O | [CH2:1]([CH:22]([NH:21][C:19]([c:18]1[c:16]([I:17])[c:7]([C:8](=[O:9])[NH:10][CH:11]([CH2:12][OH:13])[CH2:14][OH:15])[c:5]([I:6])[c:4]([OH:3])[c:27]1[I:28])=[O:20])[CH2:29][OH:31])[OH:24]>>[CH3:1][C@H:2]([O:3][c:4]1[c:5]([I:6])[c:7]([C:8](=[O:9])[NH:10][CH:11]([CH2:12][OH:13])[CH2:14][OH:15])[c:16]([I:17])[c:18]([C:19]... | O=C(NC(CO)CO)c1c(I)c(O)c(I)c(C(=O)NC(CO)CO)c1I | C[C@H](Oc1c(I)c(C(=O)NC(CO)CO)c(I)c(C(=O)NC(CO)CO)c1I)C(N)=O | null | null | COCCO | Miscellaneous | OtherReaction | 6c8f2b3bb952a7fe9d9ba1794c21b2ecbef479b16f5b4683569e954e672b1596 | 7e4dda57e0c86b8a383110aab23b72da24ab712be2c6b3824e86a807871fa757 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[#7:3]-[CH;D3;+0:4](-[CH2;D2;+0:5]-[OH;D1;+0:6])-[CH2;D2;+0:7]-[OH;D1;+0:8])-[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[CH3;D1;+0:5]-[C:14](-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]:[c:9]-[C:2](=[O;D1;H0:1])-[#7:3]-[CH;D3;+0:4](-[C:15]-[OH;D1;+0:6])-[C:16]-[O;D1;H1:17])-[C;H0;D3;+0:7](-[N;D1;H2:18])=... | 90.3 | [{"value": 45.0, "product": "NC([C@@H](OC=1C(=C(C(=C(C1I)C(=O)NC(CO)CO)I)C(=O)NC(CO)CO)I)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "NC([C@@H](OC=1C(=C(C(=C(C1I)C(=O)NC(CO)CO)I)C(=O)NC(CO)CO)I)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | To a solution of 21.8 g of N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-hydroxy-2,4,6-triiodo-1,3-benzenedicarboxamide sodium salt (prepared according to the procedure described in patent EP 185130) (0.03 mol) in 70 mL of methyl cellosolve, heated to 80° C., 14.6 g of R-2-[[(4-methylphenyl)sulfonyl]oxy]propanamide (pre... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Aromatic alcohol | Ether.Primary amide.Primary alcohol.Primary alcohol | null | null | c1ccccc1 | Other | COCCO | 80 | 8 | O=C(NC(CO)CO)c1c(I)c(O)c(I)c(C(=O)NC(CO)CO)c1I>COCCO>C[C@H](Oc1c(I)c(C(=O)NC(CO)CO)c(I)c(C(=O)NC(CO)CO)c1I)C(N)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d0de86ea40e4c07a7ac73d256823ecf | C=CN(C=O)CCC(=O)OC.OCCNCCO>>C=CN(C=O)CCC(=O)N(CCO)CCO | C(=C)N(C=O)CCC(=O)OC.N(CCO)CCO.C[O-].[Na+]>>OCCN(C(CCN(C=O)C=C)=O)CCO | CO[C:8]([CH2:7][CH2:6][N:3]([CH:2]=[CH2:1])[CH:4]=[O:5])=[O:9].[NH:10]([CH2:11][CH2:12][OH:13])[CH2:14][CH2:15][OH:16]>>[CH2:1]=[CH:2][N:3]([CH:4]=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[N:10]([CH2:11][CH2:12][OH:13])[CH2:14][CH2:15][OH:16] | C=CN(C=O)CCC(=O)OC.OCCNCCO | C=CN(C=O)CCC(=O)N(CCO)CCO | null | null | CO | Acylation | Aminolysis of esters | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | 90 | CELSIUS | 2 | HOUR | A 50 mL single-neck round bottom flask equipped with a distillation head was charged with 15.1 grams (0.096 mole) of methyl 3-(N-vinylformamido)propionate, 9.95 grams (0.09 mole) of diethanolamine and 0.15 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 2 hours and the generated... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | null | HO- | CO | 90 | 2 | C=CN(C=O)CCC(=O)OC.OCCNCCO>CO>C=CN(C=O)CCC(=O)N(CCO)CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d45c299f3f91429abf2d8013fc0f56fb | C=CN(C=O)CCC(=O)OCC.C[O-].NCCN.NCCN>>C=CN(C=O)CCC(=O)NCCNC(=O)CCN(C=C)C=O | C(CN)N.C(=C)N(C=O)CCC(=O)OCC.C(CN)N.C[O-].[Na+]>>C(=C)N(C=O)CCC(=O)NCCNC(CCN(C=O)C=C)=O | [CH2:1]=[CH:2][N:3]([CH:4]=[O:15])[CH2:6][CH2:7][C:8]([O:5][CH2:19][CH3:20])=[O:9].[CH3:21][O-:22].N[CH2:16][CH2:17][NH2:18].[NH2:10][CH2:11][CH2:14][NH2:13]>>[CH2:1]=[CH:2][N:3]([CH:4]=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:15])[CH2:16][CH2:17][N:18]([CH:19]=[CH2:20])[CH:21]=[O:22] | C=CN(C=O)CCC(=O)OCC.C[O-].NCCN.NCCN | C=CN(C=O)CCC(=O)NCCNC(=O)CCN(C=C)C=O | null | null | CO | C-C Coupling | OtherReaction | 62ae3da8cb19b8d040118904bcb1f3a539341fc71d3ddcfc2887e79538c70173 | 9ec590a7bb0409b1f6b8f9fad2afd2457245fdc91c202c3ff73cfd6ce32440ce | null | N-[CH2;D2;+0:1]-[C:2]-[NH2;D1;+0:3].[C;D1;H2:4]=[C:5]-[#7:6](-[C:7]-[C:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:12]-[CH3;D1;+0:13])-[CH;D2;+0:14]=[O;H0;D1;+0:15].[CH3;D1;+0:16]-[O-;H0;D1:17].[NH2;D1;+0:18]-[CH2;D2;+0:19]-[CH2;D2;+0:20]-[NH2;D1;+0:21]>>[C;D1;H2:4]=[C:5]-[#7:6](-[C:7]-[C:8]-[C;H0;D3;+0... | null | [] | 90 | CELSIUS | 3 | HOUR | The apparatus of Example 2 was charged with 17.1 grams (0.1 mole) of ethyl 3-(N-vinylformamido)propionate, 3.0 grams (0.05 mole) of ethylenediamine and 0.12 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 3 hours, after which the ethanol coproduct was removed by distillation at ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide.Primary amine.Primary amine.Primary amine.Primary amine | Enamine.Secondary amide.Secondary amide.Tertiary amide.Tertiary amide | null | null | null | null | CO | 90 | 3 | C=CN(C=O)CCC(=O)OCC.C[O-].NCCN.NCCN>CO>C=CN(C=O)CCC(=O)NCCNC(=O)CCN(C=C)C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-575fdaab9b024e09a2ac34fb099e5fd0 | C=CN(C=O)CCC(=O)OC.NCCCCCO>>C=CN(C=O)CCC(=O)NCCCCCO | C(=C)N(C=O)CCC(=O)OC.NCCCCCO.C[O-].[Na+]>>OCCCCCNC(CCN(C=O)C=C)=O | CO[C:8]([CH2:7][CH2:6][N:3]([CH:2]=[CH2:1])[CH:4]=[O:5])=[O:9].[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16]>>[CH2:1]=[CH:2][N:3]([CH:4]=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16] | C=CN(C=O)CCC(=O)OC.NCCCCCO | C=CN(C=O)CCC(=O)NCCCCCO | null | null | CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | The apparatus of Example 2 was charged with 15.7 grams (0.1 mol) of methyl 3-(N-vinylformamido)propionate, 10.3 grams (0.1 mol) of 5-amino-1-pentanol and 0.12 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 3 hours after which the methanol coproduct was removed by distillation a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | null | HO- | CO | null | null | C=CN(C=O)CCC(=O)OC.NCCCCCO>CO>C=CN(C=O)CCC(=O)NCCCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9263fd3c38db4e7d8af1acf74087dcb3 | C=CN(C=O)CCC(=O)OCC.OCCO>>C=CN(C=O)CCC(=O)OCCO | C(C)O.C(=C)N(C=O)CCC(=O)OCC.C(CO)O.C[O-].[Na+]>>C(=C)N(C=O)CCC(=O)OCCO | CCO[C:8]([CH2:7][CH2:6][N:3]([CH:2]=[CH2:1])[CH:4]=[O:5])=[O:9].[OH:10][CH2:11][CH2:12][OH:13]>>[CH2:1]=[CH:2][N:3]([CH:4]=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[O:10][CH2:11][CH2:12][OH:13] | C=CN(C=O)CCC(=O)OCC.OCCO | C=CN(C=O)CCC(=O)OCCO | null | null | CO | Acylation | Transesterification | c42e047d71ad2593a6d29093d1fe2ca16ccfd6db7b15eecf1eab340181aef83e | cb08be6428b0a3737df44d00995165c06a05fb7dec4fab744c09315c4f7771d4 | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | 90 | CELSIUS | 2 | HOUR | The apparatus of Example 2 was charged with 17.1 grams (0.1 mol) of ethyl 3-(N-vinylformamido)propionate, 6.2 grams (0.1 mol) of ethylene glycol, and 0.15 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 2 hours. No evolution of ethanol was observed during the reaction period. He... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | null | HO- | CO | 90 | 2 | C=CN(C=O)CCC(=O)OCC.OCCO>CO>C=CN(C=O)CCC(=O)OCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e627c68d0c1743fc987ec32e90fb2b64 | C=CCN.C=CN(C=O)CCC(=O)OCC>>C=CCNC(=O)CCN(C=C)C=O | C(=C)N(C=O)CCC(=O)OCC.C(C=C)N.C[O-].[Na+]>>C(C=C)NC(CCN(C=O)C=C)=O | [CH2:1]=[CH:2][CH2:3][NH2:4].CCO[C:5](=[O:6])[CH2:7][CH2:8][N:9]([CH:10]=[CH2:11])[CH:12]=[O:13]>>[CH2:1]=[CH:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][CH2:8][N:9]([CH:10]=[CH2:11])[CH:12]=[O:13] | C=CCN.C=CN(C=O)CCC(=O)OCC | C=CCNC(=O)CCN(C=C)C=O | null | null | CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H2:5]=[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]-[C:6]=[C;D1;H2:5] | null | [] | 90 | CELSIUS | null | null | A 100mL stainless steel high pressure reactor was charged with 17.1 grams (0.1 mol) of ethyl 3-(N-vinylformamido)propionate, 5.7 grams (0.1 mol) of allylamine and 0.15 gram of 25% sodium methoxide in methanol solution. The mixture was heated at 90° C. for 3 hours. Subsequent NMR analysis of the reaction mixture showed ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | null | HO- | CO | 90 | null | C=CCN.C=CN(C=O)CCC(=O)OCC>CO>C=CCNC(=O)CCN(C=C)C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-355d5064f2ac4906ba01a2625517f872 | CN(C)S(=O)(=O)Cl.COc1ccc(CCNC(=O)[C@@H](N)C(C)C)cc1OC>>COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)(=O)N(C)C)cc1OC | Cl.COC=1C=C(C=CC1OC)CCNC([C@H](C(C)C)N)=O.C(C)N(CC)CC.CN(S(=O)(=O)Cl)C>>COC=1C=C(C=CC1OC)CCNC([C@](C(C)C)(S(N(C)C)(=O)=O)N)=O | Cl[S:17](=[O:18])(=[O:19])[N:20]([CH3:21])[CH3:22].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C:10](=[O:11])[C@@H:12]([NH2:13])[CH:14]([CH3:15])[CH3:16])[cH:23][c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C:10](=[O:11])[C@:12]([NH2:13])([CH:14]([CH3:15])[CH3:16])[S:17](=... | CN(C)S(=O)(=O)Cl.COc1ccc(CCNC(=O)[C@@H](N)C(C)C)cc1OC | COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)(=O)N(C)C)cc1OC | null | null | O1CCOCC1 | Acylation | OtherReaction | 03df169542e61bc25f850d05576488c0b54839b94e3082a72ebb3e4f24252841 | 46615a373e6434dd65776b88d9fcc22218d37124c5265a98f610d7564f54362b | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C@@H;D3;+0:11](-[N;D1;H2:12])-[C:13](-[C;D1;H3:14])-[C;D1;H3:15]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C@;H0;D4;+0:11](-[N;D1;H2:12])(-[C:13](-[C;D1;H3:14])-[C;D1;H3:15])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H... | null | [] | null | null | null | null | 7.2 g of (S)-2-amino-3-methyl-butyric acid N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide and 4 ml of triethylamine are initially introduced in 120 ml of 1,4-dioxane at room temperature, while stirring. 2.8 ml of N,N-dimethylsulfamoyl chloride are added dropwise in the course of 5 minutes. The reaction mixture is then stirred... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | HCl | O1CCOCC1 | null | null | CN(C)S(=O)(=O)Cl.COc1ccc(CCNC(=O)[C@@H](N)C(C)C)cc1OC>O1CCOCC1>COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)(=O)N(C)C)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b5f4cb68ad14383914fad9f4aa70cd0 | COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)C(C)C)cc1OC.[O]=[Mn](=[O])(=[O])[O-]>>COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)(=O)C(C)C)cc1OC | [Mn](=O)(=O)(=O)[O-].[K+].COC=1C=C(C=CC1OC)CCNC([C@](C(C)C)(S(=O)C(C)C)N)=O.[Mn](=O)(=O)(=O)[O-]>>COC=1C=C(C=CC1OC)CCNC([C@](C(C)C)(S(=O)(=O)C(C)C)N)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C:10](=[O:11])[C@:12]([NH2:13])([CH:14]([CH3:15])[CH3:16])[S:17](=[O:19])[CH:20]([CH3:21])[CH3:22])[cH:23][c:24]1[O:25][CH3:26].[O]=[Mn](=[O])([O-])=[O:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C:10](=[O:11])[C@:12]([NH2:13])([CH:14]([CH3:15])... | COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)C(C)C)cc1OC.[O]=[Mn](=[O])(=[O])[O-] | COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)(=O)C(C)C)cc1OC | null | null | CC(=O)C | Oxidation | OtherReaction | 4094c25cd21292bb2390398fbe546de8c52271a05feb5a2820ad8177c82110cf | 0aef586d3f180a46df69203cc9de96c5ad7ea89db37e5615426f6677f8f720be | c1ccccc1 | [C:1]-[C:2](-[N;D1;H2:3])(-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7])-[S;H0;D3;+0:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])-[C;D1;H3:12].[O-]-[Mn](=[O;H0;D1;+0:13])(=[O])=[O]>>[C:1]-[C:2](-[N;D1;H2:3])(-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7])-[S;H0;D4;+0:8](=[O;D1;H0:9])(=[O;H0;D1;+0:13])-[C:10](-[C;D1;H3:11])-[C;D1;H3:12] | null | [] | null | null | 45 | MINUTE | 3.7 g of (S)-2-(isopropylsulfinyl)-amino-3-methyl-butyric acid N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide (Example 3.90) are dissolved in 50 ml of acetone at room temperature. An acetone solution saturated with potassium permanganate is added dropwise to this stirred solution until the reaction mixture retains the violet ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfoxide | Sulfone | null | null | c1ccccc1 | Other | CC(=O)C | null | 0.75 | COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)C(C)C)cc1OC.[O]=[Mn](=[O])(=[O])[O-]>CC(=O)C>COc1ccc(CCNC(=O)[C@](N)(C(C)C)S(=O)(=O)C(C)C)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f69d3edd52d44422a14f922f370dc48b | Cc1ccc(S(=O)(=O)Cl)cc1.Clc1ccccc1>>Cc1ccc(S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=CC=C1.[Cl-].[Al+3].[Cl-].[Cl-].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(C=C2)Cl | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1)(=[O:7])=[O:8].[cH:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][cH:17]1 | Cc1ccc(S(=O)(=O)Cl)cc1.Clc1ccccc1 | Cc1ccc(S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | O | Functional Group Interconversion | OtherReaction | 36deba09936956b4316cc53d96fe21a3482dda4886181801fc9170bba0f4e08d | fcd366d2a12b9f2b1304281b4b55e60873460be0844fd3f482f05b099eb21cf7 | O=S(=O)(c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[c;H0;D3;+0:9](:[c:8]:[c:7]):[c:10]:[c:11] | null | [] | 55 | CELSIUS | 3 | HOUR | To 150 ml of chlorobenzene, 100.1 g (0.75 mol) of aluminum chloride was added, and further 143 g (0.75 mol) of p-toluenesulfonyl chloride was added dropwise over 1 hour. After stirred for 3 hours at 55° C., the reaction mixture was poured into 1.5 liter of water, and then the obtained crystal was filtered off and washe... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | O | 55 | 3 | Cc1ccc(S(=O)(=O)Cl)cc1.Clc1ccccc1>O>Cc1ccc(S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ceb80269f1a342758c971e5e753be1b3 | Cc1ccc(S(=O)(=O)c2ccc(Cl)cc2)cc1.O=C(O)CS>>Cc1ccc(S(=O)(=O)c2ccc(CC(O)=S)cc2)cc1 | CC(C)O.CC1=CC=C(C=C1)S(=O)(=O)C2=CC=C(C=C2)Cl.C(CS)(=O)O.[OH-].[K+]>>CC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)CC(=S)O | Cl[c:12]1[cH:11][cH:10][c:9]([S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]2)(=[O:7])=[O:8])[cH:18][cH:17]1.O=[C:13]([CH2:14][SH:16])[OH:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][c:12]([CH2:13][C:14]([OH:15])=[S:16])[cH:17][cH:18]2)[cH:19][cH:20]1 | Cc1ccc(S(=O)(=O)c2ccc(Cl)cc2)cc1.O=C(O)CS | Cc1ccc(S(=O)(=O)c2ccc(CC(O)=S)cc2)cc1 | null | null | CN(C=O)C.O | Acylation | OtherReaction | 980d98ef4cff4e80fbd917f0526f30a1edfd5a34853250effb1682e610753519 | f99f3b1b8bff52575f3754c7ceba936ca4a0377e8b7a16a1536128e4240695d4 | O=S(=O)(c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=[C;H0;D3;+0:6](-[OH;D1;+0:7])-[CH2;D2;+0:8]-[SH;D1;+0:9]>>[OH;D1;+0:7]-[C;H0;D3;+0:8](=[S;H0;D1;+0:9])-[CH2;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 120 | CELSIUS | 6 | HOUR | In 250 ml of N,N-dimethylformamide, 140 g of 4-methyl-4'-chlorodiphenylsulfone was dissolved, and further 77 g of thioglycolic acid and 71 g of 85% potassium hydroxide pellet were added and stirred for 6 hours at 120° C. The reaction mixture was poured into 2-propanol and filtered off to obtain a precipitate. After the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Aliphatic thiol | Thiocarbonyl | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.O | 120 | 6 | Cc1ccc(S(=O)(=O)c2ccc(Cl)cc2)cc1.O=C(O)CS>CN(C=O)C.O>Cc1ccc(S(=O)(=O)c2ccc(CC(O)=S)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-18b5af8851614af6b29619286f6beb4b | CCc1ccc(S(=O)(=O)c2ccc(CC(O)=S)cc2)cc1.Cc1ccc(S(=O)(=O)c2ccc(S(=O)(=O)CC(=O)O)cc2)cc1>>CCc1ccc(S(=O)(=O)c2ccc(S(=O)(=O)CC(=O)O)cc2)cc1 | CC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)S(=O)(=O)CC(=O)O.C(C)C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)CC(=S)O>>C(C)C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)S(=O)(=O)CC(=O)O | O=S(=O)(c1ccc(CC(O)=S)cc1)c1ccc(C[CH3:1])cc1.[CH3:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][c:13]([S:14](=[O:15])(=[O:16])[CH2:17][C:18](=[O:19])[OH:20])[cH:21][cH:22]2)[cH:23][cH:24]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][c:13]([S:14](=[O:15])(=[O:... | CCc1ccc(S(=O)(=O)c2ccc(CC(O)=S)cc2)cc1.Cc1ccc(S(=O)(=O)c2ccc(S(=O)(=O)CC(=O)O)cc2)cc1 | CCc1ccc(S(=O)(=O)c2ccc(S(=O)(=O)CC(=O)O)cc2)cc1 | null | null | null | C-C Coupling | C-methylation | 0d792d43f0e84cdc445469eaab43b42dbd3bb565785bce19074c0f35bf28b708 | 72ed4a4d50b24ee609b5dd3617a985d9e1247237aa6a989345a62e0ac155b36d | O=S(=O)(c1ccccc1)c1ccccc1 | O-C(=S)-C-c1:c:c:c(-S(=O)(=O)-c2:c:c:c(-C-[CH3;D1;+0:1]):c:c:2):c:c:1.[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | The intended 4-(4-ethylphenylsulfonyl)phenylsulfonyl acetic acid was prepared in the same manner as in the synthesis of 4-(4-methylphenylsulfonyl)phenylsulfonyl acetic acid of Example 6 except that 104 g of 4-(4-ethylphenylsulfonyl)phenylthio acetic acid was used in place of 100 g of 4-(4-methylphenylsulfonyl)phenylthi... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Thiocarbonyl.Sulfone | null | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | TsOH | null | null | null | CCc1ccc(S(=O)(=O)c2ccc(CC(O)=S)cc2)cc1.Cc1ccc(S(=O)(=O)c2ccc(S(=O)(=O)CC(=O)O)cc2)cc1>>CCc1ccc(S(=O)(=O)c2ccc(S(=O)(=O)CC(=O)O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a215651ccfd41dd9aa2a1416e37b1fc | COc1ccc(C(=O)c2ccc(OC)cc2OC)c(OC)c1>>O=C(c1ccc(O)cc1O)c1ccc(O)cc1O | [Al+3].[Cl-].[Cl-].[Cl-].CN(C=O)C.COC1=C(C(=O)C2=C(C=C(C=C2)OC)OC)C=CC(=C1)OC>>OC1=C(C(=O)C2=C(C=C(C=C2)O)O)C=CC(=C1)O | C[O:7][c:6]1[cH:5][cH:4][c:3]([C:2](=[O:1])[c:11]2[cH:12][cH:13][c:14]([O:15]C)[cH:16][c:17]2[O:18]C)[c:9]([O:10]C)[cH:8]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]1[OH:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]1[OH:18] | COc1ccc(C(=O)c2ccc(OC)cc2OC)c(OC)c1 | O=C(c1ccc(O)cc1O)c1ccc(O)cc1O | null | null | O | Deprotection | OtherReaction | c9880ca160f0c4ae2189b61831917f8d0a43b3234e3cf24dfacfce49c06cf551 | 5bfe12e4c5805fe4d4a54cd53f600057b4fffbdf3214f3b83139c3362aecb6bc | O=C(c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](-[O;H0;D2;+0:8]-C):[c:9]:[c:10](-[O;H0;D2;+0:11]-C):[c:12]):[c:13]:[c:14](-[O;H0;D2;+0:15]-C):[c:16]>>[O;D1;H0:5]=[C:4](-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10](-[OH;D1;+0:11]):[c:12])-[c:3]:[c:2](-[OH;D1;+0:1]):[c:13]:[c:14](-[OH;D1;+0:15]):[c:16] | null | [] | 30 | CELSIUS | 4.5 | HOUR | 440 g (3.30 mol) of AlCl3 were stirred into 120 g (1.64 mol) of dimethylformamide in such a way that the temperature remained below 160° C. After cooling to 30° C., 60.5 g (0.20 mol) of 2,2',4,4'-tetramethoxybenzophenone were introduced into the mixture, which was easily stirrable. The mixture was stirred at about 50°-... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | O | 30 | 4.5 | COc1ccc(C(=O)c2ccc(OC)cc2OC)c(OC)c1>O>O=C(c1ccc(O)cc1O)c1ccc(O)cc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3dda345d3c8b43eca91644036bf8ff3e | COc1ccc(C(=O)c2ccc(OC)cc2O)c(O)c1>>O=C(c1ccc(O)cc1O)c1ccc(O)cc1O | OC1=C(C(=O)C2=C(C=C(C=C2)OC)O)C=CC(=C1)OC.[Al+3].[Cl-].[Cl-].[Cl-].CN(C=O)C>>OC1=C(C(=O)C2=C(C=C(C=C2)O)O)C=CC(=C1)O | C[O:7][c:6]1[cH:5][cH:4][c:3]([C:2](=[O:1])[c:11]2[cH:12][cH:13][c:14]([O:15]C)[cH:16][c:17]2[OH:18])[c:9]([OH:10])[cH:8]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][c:9]1[OH:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]1[OH:18] | COc1ccc(C(=O)c2ccc(OC)cc2O)c(O)c1 | O=C(c1ccc(O)cc1O)c1ccc(O)cc1O | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C(c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 82.2 g (0.30 mol) of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone were reacted with 600 g of AlCl3 (4.50 mol) and 180 g (2.47 mol) of DMF (dimethylformamide) as in Example 2, and the product was worked up as described.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | COc1ccc(C(=O)c2ccc(OC)cc2O)c(O)c1>>O=C(c1ccc(O)cc1O)c1ccc(O)cc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-86e31c9534414a65b91ab486505f6497 | [OH-].c1ccc([P+]2(c3ccccc3)Cc3ccc4ccccc4c3-c3c(ccc4ccccc34)C2)cc1>>Cc1ccc2ccccc2c1-c1c(CP(=O)(c2ccccc2)c2ccccc2)ccc2ccccc12 | [Br-].C1(=CC=CC=C1)[P+]1(CC2=C(C3=C(C1)C=CC1=CC=CC=C13)C=1C=CC=CC1C=C2)C2=CC=CC=C2.[OH-].[Na+]>>C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)CC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)C | [OH-:16].[CH2:1]1[c:2]2[cH:3][cH:4][c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[c:11]2-[c:12]2[c:13]([cH:29][cH:30][c:31]3[cH:32][cH:33][cH:34][cH:35][c:36]23)[CH2:14][P+:15]1([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2... | [OH-].c1ccc([P+]2(c3ccccc3)Cc3ccc4ccccc4c3-c3c(ccc4ccccc34)C2)cc1 | Cc1ccc2ccccc2c1-c1c(CP(=O)(c2ccccc2)c2ccccc2)ccc2ccccc12 | null | null | C(C)O | Miscellaneous | OtherReaction | 5bbd0389cac30f4d822c38d363c23ec25049966d8c909010dd2b41dcd38128d0 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=P(Cc1ccc2ccccc2c1-c1cccc2ccccc12)(c1ccccc1)c1ccccc1 | [OH-;D0:1].[c:2]:[c:3](:[c:4])-[CH2;D2;+0:5]-[P+;H0;D4:6](-[c:7](:[c:8]):[c:9])(-[c:10](:[c:11]):[c:12])-[C:13]-[c:14]>>[CH3;D1;+0:5]-[c:3](:[c:2]):[c:4].[O;H0;D1;+0:1]=[P;H0;D4;+0:6](-[C:13]-[c:14])(-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 4 | HOUR | 4 g (7.3 mmol) of 4,4-diphenyl-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]phosphepinium bromide are suspended in a mixture of 80 ml of 2N sodium hydroxide solution and 30 ml of ethanol and heated to boiling for 4 hours. The reaction solution is subsequently evaporated to dryness at 12 torr/40° C. The residue is taken up i... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)ccc1c2c2c(ccc3ccccc32)C[P+]C1 | null | c1ccc2ccccc2c1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | null | C(C)O | null | 4 | [OH-].c1ccc([P+]2(c3ccccc3)Cc3ccc4ccccc4c3-c3c(ccc4ccccc34)C2)cc1>C(C)O>Cc1ccc2ccccc2c1-c1c(CP(=O)(c2ccccc2)c2ccccc2)ccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-baa38a8e99a645bba8da7e83b29c024a | c1ccc([P+]2(c3ccccc3)Cc3ccc4ccccc4c3-c3c(ccc4ccccc34)C2)cc1>>Cc1ccc2ccccc2c1-c1c(CP(c2ccccc2)c2ccccc2)ccc2ccccc12 | [Br-].C1(=CC=CC=C1)[P+]1(CC2=C(C3=C(C1)C=CC1=CC=CC=C13)C=1C=CC=CC1C=C2)C2=CC=CC=C2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C1(=CC=CC=C1)P(C1=CC=CC=C1)CC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)C | [CH2:1]1[c:2]2[cH:3][cH:4][c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[c:11]2-[c:12]2[c:13]([cH:28][cH:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]23)[CH2:14][P+: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>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[c:11]1-[... | c1ccc([P+]2(c3ccccc3)Cc3ccc4ccccc4c3-c3c(ccc4ccccc34)C2)cc1 | Cc1ccc2ccccc2c1-c1c(CP(c2ccccc2)c2ccccc2)ccc2ccccc12 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 99e36e7f52659b807e758dbd044711de397b08e18d3b7e50a1c0905b20968cc8 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(P(Cc2ccc3ccccc3c2-c2cccc3ccccc23)c2ccccc2)cc1 | [c:1]:[c:2](:[c:3])-[CH2;D2;+0:4]-[P+;H0;D4:5](-[c:6](:[c:7]):[c:8])(-[c:9](:[c:10]):[c:11])-[C:12]-[c:13]>>[CH3;D1;+0:4]-[c:2](:[c:1]):[c:3].[c:13]-[C:12]-[P;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[c:9](:[c:10]):[c:11] | null | [] | null | null | 5 | HOUR | 4 g (7.3 mmol) of 4,4-diphenyl-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]phosphepinium bromide are suspended under a protective gas in 70 ml of absolute toluene. 500 mg (14.3 mmol) of lithium aluminum hydride are added to this suspension and the reaction solution is heated to boiling for 5 hours. Unreacted lithium alumin... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)ccc1c2c2c(ccc3ccccc32)C[P+]C1 | null | c1ccc2ccccc2c1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | null | C1(=CC=CC=C1)C | null | 5 | c1ccc([P+]2(c3ccccc3)Cc3ccc4ccccc4c3-c3c(ccc4ccccc34)C2)cc1>C1(=CC=CC=C1)C>Cc1ccc2ccccc2c1-c1c(CP(c2ccccc2)c2ccccc2)ccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9002cf0b40e547a59ee61a744aa9df18 | c1ccc([P+]2(c3ccccc3)Cc3ccccc3-c3ccccc3C2)cc1>>Cc1ccccc1-c1ccccc1CP(c1ccccc1)c1ccccc1 | [Br-].C1(=CC=CC=C1)[P+]1(CC2=C(C3=C(C1)C=CC=C3)C=CC=C2)C2=CC=CC=C2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C1(=CC=CC=C1)P(C1=CC=CC=C1)CC1=C(C=CC=C1)C1=C(C=CC=C1)C | [CH2:1]1[c:2]2[cH:3][cH:4][cH:5][cH:6][c:7]2-[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14][P+: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>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14][P:15]([c:16]1[cH:17][cH:18][cH:19][c... | c1ccc([P+]2(c3ccccc3)Cc3ccccc3-c3ccccc3C2)cc1 | Cc1ccccc1-c1ccccc1CP(c1ccccc1)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 69605d87899dc0bfea47a101915113dc9389e4ef5e20d0bf01dae30198c0031e | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(-c2ccccc2CP(c2ccccc2)c2ccccc2)cc1 | [c:1]-[C:2]-[P+;H0;D4:3](-[c:4](:[c:5]):[c:6])(-[c:7](:[c:8]):[c:9])-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[CH3;D1;+0:10]-[c:11](:[c:12]):[c:13].[c:1]-[C:2]-[P;H0;D3;+0:3](-[c:4](:[c:5]):[c:6])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | 4 g (9.0 mmol) of 6,6-diphenyl-6,7-dihydro-5H-dibenzo-[c,e]phosphepinium bromide are suspended in 70 ml of absolute toluene under protective gas and reacted with 680 mg (18 mmol) of lithium aluminum hydride using a method analogous to Example 5.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)C[P+]Cc1ccccc12 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | c1ccc([P+]2(c3ccccc3)Cc3ccccc3-c3ccccc3C2)cc1>C1(=CC=CC=C1)C>Cc1ccccc1-c1ccccc1CP(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9144b195488a484e95660584bc9d7fc6 | CCC(C)[P+]1(C(C)CC)Cc2ccc3ccccc3c2-c2c(ccc3ccccc23)C1>>CCC(C)P(Cc1ccc2ccccc2c1-c1c(C)ccc2ccccc12)C(C)CC | [Br-].CC(CC)[P+]1(CC2=C(C3=C(C1)C=CC1=CC=CC=C13)C=1C=CC=CC1C=C2)C(CC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CC(CC)P(C(CC)C)CC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)C | [CH3:1][CH2:2][CH:3]([CH3:4])[P+:5]1([CH:28]([CH3:29])[CH2:30][CH3:31])[CH2:6][c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[c:16]2-[c:17]2[c:18]([cH:20][cH:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]23)[CH2:19]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[P:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH... | CCC(C)[P+]1(C(C)CC)Cc2ccc3ccccc3c2-c2c(ccc3ccccc23)C1 | CCC(C)P(Cc1ccc2ccccc2c1-c1c(C)ccc2ccccc12)C(C)CC | null | null | C=1(C(=CC=CC1)C)C | Functional Group Interconversion | OtherReaction | 99e36e7f52659b807e758dbd044711de397b08e18d3b7e50a1c0905b20968cc8 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2c(-c3cccc4ccccc34)cccc2c1 | [C:1]-[C:2](-[C;D1;H3:3])-[P+;H0;D4:4](-[C:5](-[C:6])-[C;D1;H3:7])(-[C:8]-[c:9])-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[CH3;D1;+0:10]-[c:11](:[c:12]):[c:13].[C:1]-[C:2](-[C;D1;H3:3])-[P;H0;D3;+0:4](-[C:8]-[c:9])-[C:5](-[C:6])-[C;D1;H3:7] | null | [] | null | null | null | null | 4 g (7.9 mmol) of 4,4-di(1'-methylpropyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepinium bromide are suspended in 70 ml of absolute xylene and reacted with 400 mg (10.5 mmol) of lithium aluminum hydride using a method analogous to Example 5.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)ccc1c2c2c(ccc3ccccc32)C[P+]C1 | null | c1ccc2ccccc2c1.c1ccc2ccccc2c1 | null | C=1(C(=CC=CC1)C)C | null | null | CCC(C)[P+]1(C(C)CC)Cc2ccc3ccccc3c2-c2c(ccc3ccccc23)C1>C=1(C(=CC=CC1)C)C>CCC(C)P(Cc1ccc2ccccc2c1-c1c(C)ccc2ccccc12)C(C)CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7819582fed694c3f99e1f2746fab150a | CC(C)[P+]1(C(C)C)Cc2ccc3ccccc3c2-c2c(ccc3ccccc23)C1>>Cc1ccc2ccccc2c1-c1c(CP(C(C)C)C(C)C)ccc2ccccc12 | [Br-].C(C)(C)[P+]1(CC2=C(C3=C(C1)C=CC1=CC=CC=C13)C=1C=CC=CC1C=C2)C(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)(C)P(C(C)C)CC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)C | [CH2:1]1[c:2]2[cH:3][cH:4][c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[c:11]2-[c:12]2[c:13]([cH:22][cH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[CH2:14][P+:15]1([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[c:11]1-[c:12]1[c:13]([CH2:14][P:15]([CH:16](... | CC(C)[P+]1(C(C)C)Cc2ccc3ccccc3c2-c2c(ccc3ccccc23)C1 | Cc1ccc2ccccc2c1-c1c(CP(C(C)C)C(C)C)ccc2ccccc12 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 99e36e7f52659b807e758dbd044711de397b08e18d3b7e50a1c0905b20968cc8 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2c(-c3cccc4ccccc34)cccc2c1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[P+;H0;D4:4](-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])(-[C:8]-[c:9])-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[P;H0;D3;+0:4](-[C:8]-[c:9])-[C:5](-[C;D1;H3:6])-[C;D1;H3:7].[CH3;D1;+0:10]-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | 4 g (8.4 mmol) of 4,4-diisopropyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepinium bromide are suspended in 70 ml of absolute toluene under protective gas and reacted with 400 mg (10.5 mmol) of lithium aluminum hydride using a method analogous to Example 5.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)ccc1c2c2c(ccc3ccccc32)C[P+]C1 | null | c1ccc2ccccc2c1.c1ccc2ccccc2c1 | null | C1(=CC=CC=C1)C | null | null | CC(C)[P+]1(C(C)C)Cc2ccc3ccccc3c2-c2c(ccc3ccccc23)C1>C1(=CC=CC=C1)C>Cc1ccc2ccccc2c1-c1c(CP(C(C)C)C(C)C)ccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c24b8279498c4f1780da6e8b6f498cbc | CCCCCCCC=O.O=Cc1ccccc1>>CCCCCCC(C=O)=Cc1ccccc1.CCCCCCCC=O.O=Cc1ccccc1 | C(CCCCCCC)=O.C(C1=CC=CC=C1)=O>>C(C1=CC=CC=C1)=O.C(CCCCCCC)=O.C(CCCCC)C(C=O)=CC1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[O:9].[cH:10]1[cH:31][cH:30][cH:29][c:28]([CH:27]=[O:26])[cH:33]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH:8]=[O:9])=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[O:25].[O:26]=[CH:27... | CCCCCCCC=O.O=Cc1ccccc1 | CCCCCCC(C=O)=Cc1ccccc1.CCCCCCCC=O.O=Cc1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0372dbf87c8b3baa6111ae193e012612acfceb9695609df4651d1b12bc52db67 | f2d6b3b078203bee78dabcac04571761da415ea369d366eb759c2728ef152f21 | c1ccccc1.c1ccccc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[C:4]=[O;D1;H0:5].[O;D1;H0:6]=[C:7]-[c:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1>>[C:1]-[C:2]-[C;H0;D3;+0:3](-[C:4]=[O;D1;H0:5])=[CH;D2;+0:12]-[c:14](:[c:15]):[c:16].[O;D1;H0:6]=[C:7]-[c:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[c:17]:[cH;D2;+0:13]:1 | null | [] | null | null | null | null | The conversion of the benzaldehyde (bald) amounted to 65.6% and the degree of conversion of octanal to 100%. The selectivities of benzaldehyde and octanal to give α-hexylcinnamaldehyde (α-hex) were 94.9% and 96.2%, respectively, while the selectivity of octanal to give α-hexyldecenal (α-HD) was 1.0%.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Aldehyde.Aldehyde | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | null | CCCCCCCC=O.O=Cc1ccccc1>>CCCCCCC(C=O)=Cc1ccccc1.CCCCCCCC=O.O=Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d3c682656e894ba7964c3b5aa97e319e | CCCCCCCC=O.O=Cc1ccccc1>>CCCCCCC(C=O)=Cc1ccccc1 | C(CCCCCCC)=O.C(C1=CC=CC=C1)=O.N1CCCC1.C1(=CC=CC=C1)NC1=CC=CC=C1.C(C)(=O)O.[OH-].[Na+].C(C)(=O)O.C(CCCCCCC)=O>>C(CCCCC)C(C=O)=CC1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[O:9].O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH:8]=[O:9])=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CCCCCCCC=O.O=Cc1ccccc1 | CCCCCCC(C=O)=Cc1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 154f038b7f5648ae5349abff8a924c982177f620bdfb6a2f53d7ca0fce37c68d | 3174a51604157c488f07402e36f994f716989b8fc10687ee243713b4cfbdb11a | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[C:8]=[O;D1;H0:9]>>[C:5]-[C:6]-[C;H0;D3;+0:7](-[C:8]=[O;D1;H0:9])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 85 | CELSIUS | 180 | MINUTE | The reaction was carried out in a 2.5 litre double-walled glass reactor provided with a cooler, turbine stirrer (6 blades), thermocouple and a submerged metering tube. A mixture of 1065 grams of benzaldehyde (10.0 mol), 48.8 grams of pyrrolidine (0.679 mol) and 1.8 grams of diphenylamine was heated to 85° C. Over a per... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Aldehyde | null | null | c1ccccc1 | HO- | null | 85 | 3 | CCCCCCCC=O.O=Cc1ccccc1>>CCCCCCC(C=O)=Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d50ad566a2f43caa35ed18dd7496bf1 | CCCCCCCC=O.O=Cc1ccccc1>>CCCCCCC(C=O)=Cc1ccccc1 | C(C1=CC=CC=C1)=O.C(CCCCCCC)=O>>C(CCCCC)C(C=O)=CC1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[O:9].O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH:8]=[O:9])=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CCCCCCCC=O.O=Cc1ccccc1 | CCCCCCC(C=O)=Cc1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 154f038b7f5648ae5349abff8a924c982177f620bdfb6a2f53d7ca0fce37c68d | 3174a51604157c488f07402e36f994f716989b8fc10687ee243713b4cfbdb11a | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[C:8]=[O;D1;H0:9]>>[C:5]-[C:6]-[C;H0;D3;+0:7](-[C:8]=[O;D1;H0:9])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The method of claim 1 or 2, wherein α-hexylcinnamaldehyde is prepared via aldol condensation of benzaldehyde and n-octanal.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Aldehyde | null | null | c1ccccc1 | HO- | null | null | null | CCCCCCCC=O.O=Cc1ccccc1>>CCCCCCC(C=O)=Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ef5596a4da4243beba3c5680c17f513e | ClCc1ccccc1.O>>OCc1ccccc1.c1ccc(COCc2ccccc2)cc1 | C(C1=CC=CC=C1)Cl.O>>C(C1=CC=CC=C1)O.C(C1=CC=CC=C1)OCC1=CC=CC=C1 | Cl[CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[OH2:1]>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[cH:9]1[cH:10][cH:11][c:12]([CH2:13][O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23]1 | ClCc1ccccc1.O | OCc1ccccc1.c1ccc(COCc2ccccc2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b3d5a94c37a1c91f1c785fd36b5598c0ee81262b64aead6380d2022741e043ad | e60a1287d01749b8d52e42fb3423e3f2559430d2de6ab05369b4de69515bcf91 | c1ccc(COCc2ccccc2)cc1.c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH2;D0;+0:5]>>[OH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 5.4 | [{"value": 5.4, "product": "C(C1=CC=CC=C1)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 126.5 g (1 mol) of benzyl chloride and 180 g (10 mol) of water were rapidly heated to reflux in a flask with baffles and propeller stirrer with vigorous stirring (250 rpm) under nitrogen. After 240 min reaction time, the mixture was rapidly cooled, the organic phase was separated off after addition of toluene, and anal... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether.Primary alcohol | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | ClCc1ccccc1.O>>OCc1ccccc1.c1ccc(COCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ced4cee9a3c4c979b4e3a0eb0a11cbb | COc1ccccc1N.O=S(=O)(Cl)c1cccnc1>>COc1ccccc1NS(=O)(=O)c1cccnc1 | C([O-])([O-])=O.[Na+].[Na+].N1=CC=CC=C1.COC=1C(=CC=CC1)N.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl>>COC1=C(C=CC=C1)NS(=O)(=O)C=1C=NC=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1 | COc1ccccc1N.O=S(=O)(Cl)c1cccnc1 | COc1ccccc1NS(=O)(=O)c1cccnc1 | null | null | C1(=CC=CC=C1)C.O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cccnc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | 83.5 | [{"value": 83.5, "product": "COC1=C(C=CC=C1)NS(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.5, "product": "COC1=C(C=CC=C1)NS(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1.5 | HOUR | o-Anisidine (377 mg, 3.0 mmol) was dissolved in toluene (10 ml) to which were subsequently added pyridine (0.48 ml, 6.0 mmol) and 3-pyridinesulfonylchloride hydrochloride (642 mg, 3.0 mmol) at room temperature. After 1.5 hours of stirring at 100° C., the resulting reaction solution was mixed with water (20 ml), adjuste... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccncc1 | HCl | C1(=CC=CC=C1)C.O | 100 | 1.5 | COc1ccccc1N.O=S(=O)(Cl)c1cccnc1>C1(=CC=CC=C1)C.O>COc1ccccc1NS(=O)(=O)c1cccnc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-04e2e891f8e24233803e97b3a1a02cf4 | COc1ccccc1N.Cc1ccc(S(=O)(=O)Cl)cc1>>COc1ccccc1NS(=O)(=O)c1ccc(C)cc1 | O.N1=CC=CC=C1.COC=1C(=CC=CC1)N.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>COC1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]1 | COc1ccccc1N.Cc1ccc(S(=O)(=O)Cl)cc1 | COc1ccccc1NS(=O)(=O)c1ccc(C)cc1 | null | CN(C1=CC=NC=C1)C | C1(=CC=CC=C1)C | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 84f0a2c480e4021adb28613388cdf35ca03a8bd65bbdad356e160a1b94684976 | 2988afdf4a13d931f021994343ac8648c6e63ca3a4c0ba598a4b99bbffc001c8 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 62 | [{"value": 62.0, "product": "COC1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "COC1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | o-Anisidine (2.34 ml, 20 mmol) was dissolved in toluene (60 ml) to which were subsequently added, with cooling in an ice bath, pyridine (4.58 ml, 60 mmol), p-toluenesulfonyl chloride (3.89 g, 20 mmol) and a catalytically effective amount of 4-dimethylaminopyridine. After 2.5 hours of stirring at room temperature, the r... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.C1(=CC=CC=C1)C | null | 2.5 | COc1ccccc1N.Cc1ccc(S(=O)(=O)Cl)cc1>CN(C1=CC=NC=C1)C.C1(=CC=CC=C1)C>COc1ccccc1NS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80f67fcb3ee14ef2b196db2ad72d47b4 | COc1ccc(S(=O)(=O)Cl)cc1.COc1ccccc1N>>COc1ccc(S(=O)(=O)Nc2ccccc2OC)cc1 | COC=1C(=CC=CC1)N.COC1=CC=C(C=C1)S(=O)(=O)Cl>>COC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]1)(=[O:8])=[O:9].[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[O:17][CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17][CH3:18])[cH:19][cH:20]1 | COc1ccc(S(=O)(=O)Cl)cc1.COc1ccccc1N | COc1ccc(S(=O)(=O)Nc2ccccc2OC)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 90.1 | [{"value": 90.1, "product": "COC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "COC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using o-anisidine (1.0 ml, 8.55 mmol) and 4-methoxybenzenesulfonyl chloride (1.78 g, 8.55 mmol), the procedure of Reference Example 2 was repeated to obtain 2.26 g (90.1%) of the title compound in the form of colorless powder.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccc(S(=O)(=O)Cl)cc1.COc1ccccc1N>>COc1ccc(S(=O)(=O)Nc2ccccc2OC)cc1 |
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