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-01dbb772c5e249108f0b191ed17a2c0c | ord-06b4a9fc73af486aaef1030ea95c72c8 | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1cccnc1)c1cccs1>>O=C(O)CCCC/C=C(/c1cccnc1)c1cccs1 | C(C1=CN=CC=C1)(=O)C=1SC=CC1.[H-].[Na+].CS(=O)C.[Br-].C(=O)(O)CCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C=1SC=CC1 | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])cc1.O=[C:9]([c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][s:20]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9](/[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][s:20]1 | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1cccnc1)c1cccs1 | O=C(O)CCCC/C=C(/c1cccnc1)c1cccs1 | null | null | O.O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 6dd0a5c38831fb7d6f247fdce547914e97c2a39af502d5696ce93cba92b782d4 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | [CH]=C(c1cccnc1)c1cccs1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[c:7](:[c:8]):[#16;a:9]:[c:10].[C:11]-[C:12]-[CH2;D2;+0:13]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:11]-[C:12]/[CH;D2;+0:13]=[C;H0;D3;+0:1](/[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[c:7](:[c:8]):[#16;a:9]:[c:10] | 29 | [{"value": 29.0, "product": "N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.5, "product": "N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 8 | HOUR | Sodium hydride (60% in oil, 10 g, 0.25 mole) was added to dimethyl sulfoxide (250 ml) under argon and the mixture was stirred at 85° C. for an hour. The mixture was then cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (52 g, 0.11 mole) was added gradually with the temperature being maintained... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccncc1.c1ccsc1 | HO- | O.O1CCCC1 | 85 | 8 | O=C(O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(c1cccnc1)c1cccs1>O.O1CCCC1>O=C(O)CCCC/C=C(/c1cccnc1)c1cccs1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-469f9aa04d4a4ee282aa8435ec72848a | CC(=O)CCl.CC1(C)NC(=O)c2cc(O)ccc2O1>>CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2 | ClCC(C)=O.C([O-])([O-])=O.[K+].[K+].ClCC(C)=O.CC1(OC2=C(C(N1)=O)C=C(C=C2)O)C>>CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)=O)C | Cl[CH2:4][C:2]([CH3:1])=[O:3].[OH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[NH:14][C:15]([CH3:16])([CH3:17])[O:18]2>>[CH3:1][C:2](=[O:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[NH:14][C:15]([CH3:16])([CH3:17])[O:18]2 | CC(=O)CCl.CC1(C)NC(=O)c2cc(O)ccc2O1 | CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C1NCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 70 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one are refluxed for 30 hours, whilst stirring, in 400 ml of acetonitrile with 100 g of potassium carbonate and 32 ml of chloroacetone. After the addition of a further 3.2 ml of chloroacetone, the reaction mixture is heated for a further 15 to 20 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccc2c(c1)CNCO2 | HCl | C(C)#N | null | null | CC(=O)CCl.CC1(C)NC(=O)c2cc(O)ccc2O1>C(C)#N>CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-93a5ea0a4f844f3b992c9c05b03c834a | CC(=O)COc1ccc(O)c(C(N)=O)c1.NCc1ccccc1>>CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1 | C(C1=CC=CC=C1)N.S(O)(O)(=O)=O.O=C(COC1=CC=C(C(C(=O)N)=C1)O)C.[H][H]>>C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C | O=[C:2]([CH3:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([NH2:12])=[O:13])[cH:14]1.[NH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([NH2:12])=[O:13])[cH:14]1)[NH:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(=O)COc1ccc(O)c(C(N)=O)c1.NCc1ccccc1 | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1 | null | [Pt] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CNCCOc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[#8:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | 55 g of benzylamine and 1.25 g of concentrated sulphuric acid are added to a solution of 104.5 g of 5-(2-oxopropoxy)salicylamide in 100 ml of methanol and hydrogenated in the presence of 3.0 g of Pt/C-catalyst at room temperature and atmospheric pressure until 1 equivalent of hydrogen has been absorbed. The catalyst is... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pt].CO | null | null | CC(=O)COc1ccc(O)c(C(N)=O)c1.NCc1ccccc1>[Pt].CO>CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-828bade31618484ebf88db104605db75 | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.COCCOc1ccc(OCC2CO2)cc1>>COCCOc1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc(O)c(C(N)=O)c2)cc1 | O1C(COC2=CC=C(C=C2)OCCOC)C1.C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C>>C(N)(=O)C=1C=C(OCC(C)N(CC(COC2=CC=C(C=C2)OCCOC)O)CC2=CC=CC=C2)C=CC1O | [NH:15]([CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH:23]([CH3:24])[CH2:25][O:26][c:27]1[cH:28][cH:29][c:30]([OH:31])[c:32]([C:33]([NH2:34])=[O:35])[cH:36]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]2[O:13][CH2:14]2)[cH:37][cH:38]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7]... | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.COCCOc1ccc(OCC2CO2)cc1 | COCCOc1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc(O)c(C(N)=O)c2)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc(CN(CCCOc2ccccc2)CCOc2ccccc2)cc1 | [C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5]-[c:6].[C:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:7]-[C:8](-[OH;D1;+0:10])-[CH2;D2;+0:9]-[N;H0;D3;+0:4](-[C:5]-[c:6])-[C:2](-[C:1])-[C;D1;H3:3] | null | [] | null | null | null | null | A solution of 10.2 g of 1-(2,3-epoxypropoxy)-4-(2-methoxyethoxy)benzene and 11.0 g of 5-[2-(benzylamino)propoxy]salicylamide in 200 ml of isopropanol is refluxed for 24 hours. By concentration of the solution by evaporation, crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethyl]benzylamino]-3-[4-(2-methoxyethoxy)p... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C(C)(C)O | null | null | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.COCCOc1ccc(OCC2CO2)cc1>C(C)(C)O>COCCOc1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc(O)c(C(N)=O)c2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d820998eb2b146de9eeca6c829a21010 | BrCCBr.CC1(C)NC(=O)c2cc(O)ccc2O1>>CC1(C)NC(=O)c2cc(OCCBr)ccc2O1 | CC1(OC2=C(C(N1)=O)C=C(C=C2)O)C.C([O-])([O-])=O.[K+].[K+].BrCCBr>>BrCCOC=1C=CC2=C(C(NC(O2)(C)C)=O)C1 | Br[CH2:11][CH2:12][Br:13].[CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[O:6])[c:7]2[cH:8][c:9]([OH:10])[cH:14][cH:15][c:16]2[O:17]1>>[CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[O:6])[c:7]2[cH:8][c:9]([O:10][CH2:11][CH2:12][Br:13])[cH:14][cH:15][c:16]2[O:17]1 | BrCCBr.CC1(C)NC(=O)c2cc(O)ccc2O1 | CC1(C)NC(=O)c2cc(OCCBr)ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1NCOc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[Br;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of 48.2 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one, 70 g of potassium carbonate and 250 ml of 1,2-dibromoethane is refluxed for 4 hours whilst stirring. The semi-liquid reaction mixture is extracted 3 to 4 times whilst hot with 1 liter of methanol each time; the combined methanol extracts... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CNCO2 | HBr | null | null | null | BrCCBr.CC1(C)NC(=O)c2cc(O)ccc2O1>>CC1(C)NC(=O)c2cc(OCCBr)ccc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e1fe952fc9394d3395d3744c308e4732 | COCCOc1ccc(OCC(O)CN(CCCc2ccc(O)c(C(N)=O)c2)Cc2ccccc2)cc1>>COCCOc1ccc(OCC(O)CNCCCc2ccc(O)c(C(N)=O)c2)cc1 | C(N)(=O)C=1C=C(C=CC1O)CCCN(CC(COC1=CC=C(C=C1)OCCOC)O)CC1=CC=CC=C1.Cl>>C(N)(=O)C=1C=C(C=CC1O)CCCNCC(COC1=CC=C(C=C1)OCCOC)O.Cl | c1ccc(C[N:15]([CH2:14][CH:12]([CH2:11][O:10][c:9]2[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:30][cH:29]2)[OH:13])[CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][c:22]([OH:23])[c:24]([C:25]([NH2:26])=[O:27])[cH:28]2)cc1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]([OH:13])[CH2:1... | COCCOc1ccc(OCC(O)CN(CCCc2ccc(O)c(C(N)=O)c2)Cc2ccccc2)cc1 | COCCOc1ccc(OCC(O)CNCCCc2ccc(O)c(C(N)=O)c2)cc1 | null | null | CO | Deprotection | Hydrogenolysis of tertiary amines | c7b12980b0925f19f153d220e0d23df430cf55f157d3497ce9d59af5c5715792 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(CCCNCCCOc2ccccc2)cc1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of 16 g of crude 1-[N-[3-(3-carbamoyl-4-hydroxyphenyl)propyl]benzylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol is hydrogenated analogously to Example 1. The hydrogenating solution is neutralised with a solution of hydrochloric acid gas in methanol, concentrated by evaporation and crystallised from aceto... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | COCCOc1ccc(OCC(O)CN(CCCc2ccc(O)c(C(N)=O)c2)Cc2ccccc2)cc1>CO>COCCOc1ccc(OCC(O)CNCCCc2ccc(O)c(C(N)=O)c2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fd4698988d234a8f8d1a1ebb6b9094bc | CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2.NCc1ccccc1>>CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1 | CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)=O)C.C(C1=CC=CC=C1)N.S(O)(O)(=O)=O.[H][H]>>C(C1=CC=CC=C1)NC(COC=1C=CC2=C(C(NC(O2)(C)C)=O)C1)C | O=[C:2]([CH3:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[O:17]2.[NH2:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[O:17]2)[NH:18][CH2:19]... | CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2.NCc1ccccc1 | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1 | null | [Pt] | C(C)(C)O.CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=C1NCOc2ccc(OCCNCc3ccccc3)cc21 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[#8:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | A solution of 49.8 g of 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one and 21.4 g of benzylamine in 700 ml of methanol is hydrogenated with the addition of 0.5 g of concentrated sulphuric acid and 3 g of Pt/C-catalyst (5%) until the equivalent amount of hydrogen has been asborbed. Working up analogou... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccc2c(c1)CNCO2.c1ccccc1 | Other | [Pt].C(C)(C)O.CO | null | null | CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2.NCc1ccccc1>[Pt].C(C)(C)O.CO>CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-75fb8b38e64d40b591e7fff45e062a05 | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1.c1ccc(COc2ccc(OCC3CO3)cc2)cc1>>CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)N(Cc1ccccc1)CC(O)COc1ccc(OCc2ccccc2)cc1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)OCC1CO1.C(C1=CC=CC=C1)NC(COC=1C=CC2=C(C(NC(O2)(C)C)=O)C1)C>>CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)N(CC(COC2=CC=C(C=C2)OCC2=CC=CC=C2)O)CC2=CC=CC=C2)C | [CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[O:17]2)[NH:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[CH2:26]1[CH:27]([CH2:29][O:30][c:31]2[cH:32][cH:33][c:34]([O:35][CH2:36][c:37]3[cH:38][cH:39][cH:40][cH:41][cH:42]3)[cH:43][cH:44]2)[O:28]1... | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1.c1ccc(COc2ccc(OCC3CO3)cc2)cc1 | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)N(Cc1ccccc1)CC(O)COc1ccc(OCc2ccccc2)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | O=C1NCOc2ccc(OCCN(CCCOc3ccc(OCc4ccccc4)cc3)Cc3ccccc3)cc21 | [C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5]-[c:6].[C:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:7]-[C:8](-[OH;D1;+0:10])-[CH2;D2;+0:9]-[N;H0;D3;+0:4](-[C:5]-[c:6])-[C:2](-[C:1])-[C;D1;H3:3] | null | [] | null | null | null | null | A solution of 15.4 g of benzyl [4-(2,3-epoxypropoxy)phenyl]ether and 17.0 g of 6-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one in 100 ml of isopropanol is refluxed for 24 hours, filtered and concentrated by evaporation. Trituration of the residue with approximately 200 ml of ether results in c... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2c(c1)CNCO2.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(C)(C)O | null | null | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1.c1ccc(COc2ccc(OCC3CO3)cc2)cc1>C(C)(C)O>CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)N(Cc1ccccc1)CC(O)COc1ccc(OCc2ccccc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3d6d6e38432d46b8a8a0b5dc77aff31a | CNC(=O)c1ccc(OCC(O)CNC(C)COc2ccc3c(c2)C(=O)NC(C)(C)O3)cc1>>CNC(=O)c1ccc(OCC(O)CNC(C)COc2ccc(O)c(C(N)=O)c2)cc1 | C(C)(C)N.CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)NCC(COC2=CC=C(C=C2)C(NC)=O)O)C>>C(N)(=O)C=1C=C(OCC(C)NCC(COC2=CC=C(C=C2)C(NC)=O)O)C=CC1O | CC1(C)[O:23][c:22]2[cH:21][cH:20][c:19]([O:18][CH2:17][CH:15]([NH:14][CH2:13][CH:11]([CH2:10][O:9][c:8]3[cH:7][cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:30][cH:29]3)[OH:12])[CH3:16])[cH:28][c:24]2[C:25](=[O:27])[NH:26]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]([OH:12])[CH2:13][NH:14][CH:1... | CNC(=O)c1ccc(OCC(O)CNC(C)COc2ccc3c(c2)C(=O)NC(C)(C)O3)cc1 | CNC(=O)c1ccc(OCC(O)CNC(C)COc2ccc(O)c(C(N)=O)c2)cc1 | null | null | CO | Deprotection | OtherReaction | 661fe1514f857633b73b0e1dad02767458f868ce5bca59d8faf17042ddb8af57 | 2902eb625a981761c5a520410afd09a992616e1a3bd271f13be71d300d901240 | c1ccc(OCCCNCCOc2ccccc2)cc1 | C-C1(-C)-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](:[c:6])-[O;H0;D2;+0:7]-1>>[NH2;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[OH;D1;+0:7]):[c:6] | null | [] | null | null | null | null | 80 ml of isopropylamine are added to a solution of 18.0 g of crude 1-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol in 300 ml of methanol and the solution is refluxed for 1 hour. The reaction mixture is concentrated by evaporation and the oil re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | Primary amide.Aromatic alcohol | c1ccc2c(c1)CNCO2 | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | CNC(=O)c1ccc(OCC(O)CNC(C)COc2ccc3c(c2)C(=O)NC(C)(C)O3)cc1>CO>CNC(=O)c1ccc(OCC(O)CNC(C)COc2ccc(O)c(C(N)=O)c2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fe8a390673e842ac9509d98d9cab3091 | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1.CNC(=O)c1ccc(OCC2CO2)cc1>>CNC(=O)c1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc3c(c2)C(=O)NC(C)(C)O3)cc1 | C(C1=CC=CC=C1)NC(COC=1C=CC2=C(C(NC(O2)(C)C)=O)C1)C.O1C(COC2=CC=C(C(=O)NC)C=C2)C1>>CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)N(CC(COC2=CC=C(C=C2)C(NC)=O)O)CC2=CC=CC=C2)C | [NH:14]([CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[CH:22]([CH3:23])[CH2:24][O:25][c:26]1[cH:27][cH:28][c:29]2[c:30]([cH:31]1)[C:32](=[O:33])[NH:34][C:35]([CH3:36])([CH3:37])[O:38]2.[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]2[O:12][CH2:13]2)[cH:39][cH:40]1>>[CH3:1][NH:2][C:3](=[O:4]... | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1.CNC(=O)c1ccc(OCC2CO2)cc1 | CNC(=O)c1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc3c(c2)C(=O)NC(C)(C)O3)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | O=C1NCOc2ccc(OCCN(CCCOc3ccccc3)Cc3ccccc3)cc21 | [C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5]-[c:6].[C:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:7]-[C:8](-[OH;D1;+0:10])-[CH2;D2;+0:9]-[N;H0;D3;+0:4](-[C:5]-[c:6])-[C:2](-[C:1])-[C;D1;H3:3] | null | [] | null | null | null | null | A solution of 13.6 g of 6-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one and 10.4 g of 4-(2,3-epoxypropoxy)-N-methylbenzamide in 80 ml of isopropanol is refluxed for 30 hours. The residue remaining after the solvent has been evaporated off is divided between ether and 2N hydrochloric acid. The ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CNCO2 | null | C(C)(C)O | null | null | CC(COc1ccc2c(c1)C(=O)NC(C)(C)O2)NCc1ccccc1.CNC(=O)c1ccc(OCC2CO2)cc1>C(C)(C)O>CNC(=O)c1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc3c(c2)C(=O)NC(C)(C)O3)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-673f9bcee80c4146a206f2b200ea78e4 | C=CCOc1ccccc1OCC(O)CN.CC(=O)COc1ccc(O)c(C(N)=O)c1>>C=CCOc1ccccc1OCC(O)CNC(C)COc1ccc(O)c(C(N)=O)c1 | O.C(C=C)OC1=C(OCC(CN)O)C=CC=C1.O=C(COC1=CC=C(C(C(=O)N)=C1)O)C.O>>C(C=C)OC1=C(OCC(CNC(COC2=CC(=C(C=C2)O)C(N)=O)C)O)C=CC=C1 | [CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]([OH:14])[CH2:15][NH2:16].O=[C:17]([CH3:18])[CH2:19][O:20][c:21]1[cH:22][cH:23][c:24]([OH:25])[c:26]([C:27]([NH2:28])=[O:29])[cH:30]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]([OH:14])[CH2:15]... | C=CCOc1ccccc1OCC(O)CN.CC(=O)COc1ccc(O)c(C(N)=O)c1 | C=CCOc1ccccc1OCC(O)CNC(C)COc1ccc(O)c(C(N)=O)c1 | null | C(C)(=O)O | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(OCCCNCCOc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#8:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | 8 | HOUR | A mixture of 11.2 g of 1-(2-allyloxyphenoxy)-3-aminopropan-2-ol and 10.5 g of 5-(2-oxopropoxy)salicylamide is boiled using a water separator in 200 ml of toluene with the addition of a few drops of acetic acid. After the splitting off of water has ceased (after about 2-3 hours), the solution is concentrated by evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)O.C1(=CC=CC=C1)C | null | 8 | C=CCOc1ccccc1OCC(O)CN.CC(=O)COc1ccc(O)c(C(N)=O)c1>C(C)(=O)O.C1(=CC=CC=C1)C>C=CCOc1ccccc1OCC(O)CNC(C)COc1ccc(O)c(C(N)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a1f901233c8e48c982691f27cf0723c8 | C=CCOc1ccccc1OCC(O)CN.NC(=O)c1cc(OCCBr)ccc1O>>C=CCOc1ccccc1OCC(O)CNCCOc1ccc(O)c(C(N)=O)c1 | BrCCOC1=CC=C(C(C(=O)N)=C1)O.C(C=C)OC1=C(OCC(CN)O)C=CC=C1>>C(C=C)OC1=C(OCC(CNCCOC2=CC(=C(C=C2)O)C(N)=O)O)C=CC=C1 | [CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]([OH:14])[CH2:15][NH2:16].Br[CH2:17][CH2:18][O:19][c:20]1[cH:21][cH:22][c:23]([OH:24])[c:25]([C:26]([NH2:27])=[O:28])[cH:29]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH:13]([OH:14])[CH2:15][NH:16][... | C=CCOc1ccccc1OCC(O)CN.NC(=O)c1cc(OCCBr)ccc1O | C=CCOc1ccccc1OCC(O)CNCCOc1ccc(O)c(C(N)=O)c1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(OCCCNCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | null | [] | null | null | 1 | HOUR | A mixture of 6.5 g of 5-(2-bromoethoxy)salicylamide and 8.9 g of 1-(2-allyloxyphenoxy)-3-aminopropan-2-ol is melted in an oil bath at 100° and stirred for 1 hour using a magnetic stirrer. The working up is carried out analogously to Example 11 and yields 1-(2-allyloxyphenoxy)-3-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylami... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)(C)O | null | 1 | C=CCOc1ccccc1OCC(O)CN.NC(=O)c1cc(OCCBr)ccc1O>C(C)(C)O>C=CCOc1ccccc1OCC(O)CNCCOc1ccc(O)c(C(N)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-da6fedaf49bb44f0a01d1ff0ecf5e09e | NC(=O)c1ccccc1OCc1ccccc1>>NCc1ccccc1OCc1ccccc1 | O.[OH-].[Na+].O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1=CC=CC=C1)OC1=C(C(=O)N)C=CC=C1>>C(C1=CC=CC=C1)OC1=C(CN)C=CC=C1 | O=[C:2]([NH2:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | NC(=O)c1ccccc1OCc1ccccc1 | NCc1ccccc1OCc1ccccc1 | null | null | CCOCC | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccc(COc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[c:3](:[c:4]):[c:5]>>[N;D1;H2:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 21 | HOUR | In a Soxhlet apparatus 18.4 g of lithium aluminium hydride in 1800 ml of dry ether are boiled under a nitrogen atmosphere at a bath temperature of 70°, 5.3 g of 2-benzyloxybenzamide being introduced into the Soxhlet thimble. After 21 hours the reaction mixture is immersed in an ice bath, and 18.4 ml of water, 18.4 ml o... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccccc1.c1ccccc1 | Other | CCOCC | null | 21 | NC(=O)c1ccccc1OCc1ccccc1>CCOCC>NCc1ccccc1OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c809392bdfff4c2c992ddff80aae92cb | NCc1ccccc1OCc1ccccc1.O=C(Cl)Cl>>O=C=NCc1ccccc1OCc1ccccc1 | Cl.C(C1=CC=CC=C1)OC1=C(CN)C=CC=C1.C(=O)(Cl)Cl.C(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC1=C(CN=C=O)C=CC=C1 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.Cl[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | NCc1ccccc1OCc1ccccc1.O=C(Cl)Cl | O=C=NCc1ccccc1OCc1ccccc1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccc(COc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[C:4]-[c:5]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[C:4]-[c:5] | null | [] | null | null | 10 | MINUTE | 38.5 g of 2-benzyloxybenzylamine hydrochloride are suspended in 400 ml of distilled toluene and heated at a bath temperature of 140°. Whilst stirring, phosgene is introduced and after about 50 minutes the solution becomes clear. After a further 10 minutes, the addition of phosgene is interrupted and boiling is continue... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | 0.166667 | NCc1ccccc1OCc1ccccc1.O=C(Cl)Cl>C1(=CC=CC=C1)C>O=C=NCc1ccccc1OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4afce8da2eda47f08ce5d071551bbc2e | NCCO.O=C=NCc1ccccc1OCc1ccccc1>>O=C(NCCO)NCc1ccccc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(CN=C=O)C=CC=C1.C(O)CN>>OCCNC(=O)NCC1=C(C=CC=C1)OCC1=CC=CC=C1 | [NH2:3][CH2:4][CH2:5][OH:6].[O:1]=[C:2]=[N:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | NCCO.O=C=NCc1ccccc1OCc1ccccc1 | O=C(NCCO)NCc1ccccc1OCc1ccccc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(COc2ccccc2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[C:7]-[c:8]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[C:7]-[c:8] | null | [] | null | null | null | null | A solution of 73.6 g of crude 2-benzyloxybenzyl isocyanate in 120 ml of methylene chloride is added dropwise in the course of 50 minutes in a solution of 36.8 ml of ethanolamine in 370 ml of methylene chloride. The reaction is slightly exothermic. After 2 hours the reaction solution is washed three times with 200 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | NCCO.O=C=NCc1ccccc1OCc1ccccc1>C(Cl)Cl>O=C(NCCO)NCc1ccccc1OCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-454c2953ea5c47808d6c09c24f3fa513 | O=C(NCCO)NCc1ccccc1OCc1ccccc1>>O=C(NCCO)NCc1ccccc1O | OCCNC(=O)NCC1=C(C=CC=C1)OCC1=CC=CC=C1>>OCCNC(=O)NCC1=C(C=CC=C1)O | c1ccc(C[O:15][c:14]2[c:9]([CH2:8][NH:7][C:2](=[O:1])[NH:3][CH2:4][CH2:5][OH:6])[cH:10][cH:11][cH:12][cH:13]2)cc1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15] | O=C(NCCO)NCc1ccccc1OCc1ccccc1 | O=C(NCCO)NCc1ccccc1O | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 2 | HOUR | 59.6 g of N-(2-hydroxyethyl)-N'-(2-benzyloxybenzyl)urea are dissolved in 600 ml of methanol and hydrogenated in the presence of 6 g of Pd/C-catalyst (5%). After 2 hours the hydrogenation ceases. The catalyst is suction-filtered, and the filtrate concentrated by evaporation in vacuo. The residue is recrystallised from 3... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1 | Other | [Pd].CO | null | 2 | O=C(NCCO)NCc1ccccc1OCc1ccccc1>[Pd].CO>O=C(NCCO)NCc1ccccc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b83de7ddf3984ec7810453a88a6980b1 | ClCC1CO1.O=C(NCCO)NCc1ccccc1O>>O=C(NCCO)NCc1ccccc1OCC1CO1 | OCCNC(=O)NCC1=C(C=CC=C1)O.C([O-])([O-])=O.[K+].[K+].C(Cl)C1CO1>>O1C(COC2=C(CNC(=O)NCCO)C=CC=C2)C1 | Cl[CH2:16][CH:17]1[CH2:18][O:19]1.[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][CH:17]1[CH2:18][O:19]1 | ClCC1CO1.O=C(NCCO)NCc1ccccc1O | O=C(NCCO)NCc1ccccc1OCC1CO1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC2CO2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | 6 | HOUR | A mixture of 29.2 g of N-(2-hydroxyethyl)-N'-(2-hydroxybenzyl)urea, 440 ml of epichlorohydrin and 38.9 g of potassium carbonate is stirred for 6 hours at 90°. The solids are then suction-filtered whilst hot, washed with acetonitrile and the filtrate is concentrated by evaporation in vacuo. The oil remaining crystallise... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CO1 | HCl | null | null | 6 | ClCC1CO1.O=C(NCCO)NCc1ccccc1O>>O=C(NCCO)NCc1ccccc1OCC1CO1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1b52e7de41e1401c8a5258398141f605 | BrCCBr.CC1(C)NC(=O)c2ccc(O)cc2O1>>CC1(C)NC(=O)c2ccc(OCCBr)cc2O1 | CC1(OC2=C(C(N1)=O)C=CC(=C2)O)C.BrCCBr>>CC1(OC2=C(C(N1)=O)C=CC(=C2)OCCBr)C | Br[CH2:12][CH2:13][Br:14].[CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[O:6])[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:15][c:16]2[O:17]1>>[CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[O:6])[c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][Br:14])[cH:15][c:16]2[O:17]1 | BrCCBr.CC1(C)NC(=O)c2ccc(O)cc2O1 | CC1(C)NC(=O)c2ccc(OCCBr)cc2O1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1NCOc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[Br;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 16.2 g of 2,3-dihydro-2,2-dimethyl-7-hydroxy-4H-1,3-benzoxazin-4-one are reacted analogously to Example (3a) with 84 ml of 1,2-dibromoethane and yield 2,3-dihydro-2,2-dimethyl-7-(2-bromoethoxy)-4H-1,3-benzoxazin-4-one having a melting point of 156°-158° (from isopropanol).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CNCO2 | HBr | C(C)(C)O | null | null | BrCCBr.CC1(C)NC(=O)c2ccc(O)cc2O1>C(C)(C)O>CC1(C)NC(=O)c2ccc(OCCBr)cc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2158019772d240b48c99ecea1fc7c2f3 | BrCCBr.NC(=O)c1c(O)cccc1O>>NC(=O)c1c(O)cccc1OCCBr | OC1=C(C(=O)N)C(=CC=C1)O.C([O-])([O-])=O.[K+].[K+].BrCCBr>>BrCCOC=1C=CC=C(C1C(=O)N)O | Br[CH2:12][CH2:13][Br:14].[NH2:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]1[OH:11]>>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][Br:14] | BrCCBr.NC(=O)c1c(O)cccc1O | NC(=O)c1c(O)cccc1OCCBr | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[Br;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:5](-[N;D1;H2:4])=[O;D1;H0:6] | null | [] | null | null | null | null | A mixture of 23.0 g of 2,6-dihydroxybenzamide, 20.7 g of potassium carbonate and 28.2 g of 1,2-dibromoethane is refluxed, whilst stirring, for 2-3 hours in 300 ml of acetonitrile. The reaction mixture is filtered whilst still warm, the filtrate concentrated by evaporation and the residue recrystallised from a little me... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | null | BrCCBr.NC(=O)c1c(O)cccc1O>C(C)#N>NC(=O)c1c(O)cccc1OCCBr |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5b74e8a69c9c4ca0b289ab0ce493c1ed | CC(C)(N)COc1ccc(O)c(C(N)=O)c1.N#Cc1ccccc1OCC1CO1>>CC(C)(COc1ccc(O)c(C(N)=O)c1)NCC(O)COc1ccccc1C#N | NC(COC1=CC=C(C(C(=O)N)=C1)O)(C)C.O1C(COC2=C(C#N)C=CC=C2)C1>>C(N)(=O)C=1C=C(OCC(C)(C)NCC(COC2=C(C=CC=C2)C#N)O)C=CC1O | [CH3:1][C:2]([CH3:3])([CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([C:12]([NH2:13])=[O:14])[cH:15]1)[NH2:16].[CH2:17]1[CH:18]([CH2:20][O:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]#[N:29])[O:19]1>>[CH3:1][C:2]([CH3:3])([CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([C:12]([NH2:13])=[O:14])[cH:15]1)[NH... | CC(C)(N)COc1ccc(O)c(C(N)=O)c1.N#Cc1ccccc1OCC1CO1 | CC(C)(COc1ccc(O)c(C(N)=O)c1)NCC(O)COc1ccccc1C#N | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(OCCCNCCOc2ccccc2)cc1 | [C:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH2;D1;+0:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C:6]-[C:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[NH;D2;+0:5]-[C:2](-[C:1])(-[C;D1;H3:3])-[C;D1;H3:4] | null | [] | null | null | null | null | The solution of 2.24 g of 5-(2-amino-2-methylpropoxy)salicylamide in 30 ml of dioxan is refluxed for 7 hours after the addition of 2.3 g of 2-(2,3-epoxypropoxy)benzonitrile, and then concentrated by evaporation. The residue is divided between 10 ml of 2N hydrochloric acid and 100 ml of ethyl acetate. The acidic aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.c1ccccc1 | null | O1CCOCC1 | null | null | CC(C)(N)COc1ccc(O)c(C(N)=O)c1.N#Cc1ccccc1OCC1CO1>O1CCOCC1>CC(C)(COc1ccc(O)c(C(N)=O)c1)NCC(O)COc1ccccc1C#N |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f856ad7b2cbf4d718c46453c87b095f0 | CC(C)(COc1ccc(O)c(C(N)=O)c1)[N+](=O)[O-]>>CC(C)(N)COc1ccc(O)c(C(N)=O)c1 | CC(COC1=CC=C(C(C(=O)N)=C1)O)(C)[N+](=O)[O-]>>NC(COC1=CC=C(C(C(=O)N)=C1)O)(C)C | O=[N+:4]([O-])[C:2]([CH3:1])([CH3:3])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[c:12]([C:13]([NH2:14])=[O:15])[cH:16]1>>[CH3:1][C:2]([CH3:3])([NH2:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[c:12]([C:13]([NH2:14])=[O:15])[cH:16]1 | CC(C)(COc1ccc(O)c(C(N)=O)c1)[N+](=O)[O-] | CC(C)(N)COc1ccc(O)c(C(N)=O)c1 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | null | null | 11.5 g 5-(2-methyl-2-nitropropoxy)salicylamide are hydrogenated in 150 ml of methanol at 40°-50° and 80 bar over 5 g of Raney nickel until hydrogen absorption ceases. By filtration and concentration of the filtrate by evaporation, crude 5-(2-amino-2-methylpropoxy)salicylamide is obtained, which, after standing for a re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CO | null | null | CC(C)(COc1ccc(O)c(C(N)=O)c1)[N+](=O)[O-]>CO>CC(C)(N)COc1ccc(O)c(C(N)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b1956ecd3bfc4500ac0ede3e046b88ed | COC(=O)c1ccc(OCC(O)CNC(C)COc2ccc(O)c(C(N)=O)c2)cc1O.N>>CC(COc1ccc(O)c(C(N)=O)c1)NCC(O)COc1ccc(C(N)=O)c(O)c1 | N.C(N)(=O)C=1C=C(OCC(C)NCC(COC2=CC(=C(C=C2)C(=O)OC)O)O)C=CC1O>>C(N)(=O)C1=C(C=C(OCC(CNC(COC2=CC(=C(C=C2)O)C(N)=O)C)O)C=C1)O | CO[C:25]([c:24]1[cH:23][cH:22][c:21]([O:20][CH2:19][CH:17]([CH2:16][NH:15][CH:2]([CH3:1])[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([NH2:12])=[O:13])[cH:14]2)[OH:18])[cH:30][c:28]1[OH:29])=[O:27].[NH3:26]>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([NH2:12])=[O:13])[cH:14]1)[NH... | COC(=O)c1ccc(OCC(O)CNC(C)COc2ccc(O)c(C(N)=O)c2)cc1O.N | CC(COc1ccc(O)c(C(N)=O)c1)NCC(O)COc1ccc(C(N)=O)c(O)c1 | null | null | O1CCOCC1 | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc(OCCCNCCOc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1.5 | HOUR | A mixture of 50 ml of dioxan and 500 ml of concentrated ammonia solution is added to 21.5 g of 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)propan-2-ol. The reaction mixture is stirred for 1-2 hours, and as soon as it is homogeneous, left to stand for 3 days at 20°-30°. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCOCC1 | null | 1.5 | COC(=O)c1ccc(OCC(O)CNC(C)COc2ccc(O)c(C(N)=O)c2)cc1O.N>O1CCOCC1>CC(COc1ccc(O)c(C(N)=O)c1)NCC(O)COc1ccc(C(N)=O)c(O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-04f489d6f4b84e0caced2494d503c25d | COC(=O)c1ccc(O)cc1O.ClCC1CO1>>COC(=O)c1ccc(OCC2CO2)cc1O | COC(C1=C(C=C(C=C1)O)O)=O.C(Cl)C1CO1.C([O-])([O-])=O.[K+].[K+]>>COC(C=1C(O)=CC(=CC1)OCC1CO1)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:14][c:15]1[OH:16].Cl[CH2:10][CH:11]1[CH2:12][O:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]2[CH2:12][O:13]2)[cH:14][c:15]1[OH:16] | COC(=O)c1ccc(O)cc1O.ClCC1CO1 | COC(=O)c1ccc(OCC2CO2)cc1O | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC2CO2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | null | null | By refluxing 34 g of 2,4-dihydroxybenzoic acid methyl ester with 185 g of epichlorohydrin and 35 g of potassium carbonate for 2 to 3 hours, and chromatographing the crude product on 100 g of silica gel (elution with toluene), 4-(2,3-epoxypropoxy)salicylic acid methyl ester having a melting point of 53°-55° is obtained.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CO1 | HCl | null | null | null | COC(=O)c1ccc(O)cc1O.ClCC1CO1>>COC(=O)c1ccc(OCC2CO2)cc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7f10f021005f4af18df8b64a1ea0e211 | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.COC(=O)c1ccc(OCC2CO2)cc1O>>COC(=O)c1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc(O)c(C(N)=O)c2)cc1O | COC(C=1C(O)=CC(=CC1)OCC1CO1)=O.C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C>>C(N)(=O)C=1C=C(OCC(C)N(CC(COC2=CC(=C(C=C2)C(=O)OC)O)O)CC2=CC=CC=C2)C=CC1O | [NH:14]([CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[CH:22]([CH3:23])[CH2:24][O:25][c:26]1[cH:27][cH:28][c:29]([OH:30])[c:31]([C:32]([NH2:33])=[O:34])[cH:35]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]2[O:12][CH2:13]2)[cH:36][c:37]1[OH:38]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][... | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.COC(=O)c1ccc(OCC2CO2)cc1O | COC(=O)c1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc(O)c(C(N)=O)c2)cc1O | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc(CN(CCCOc2ccccc2)CCOc2ccccc2)cc1 | [C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5]-[c:6].[C:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:7]-[C:8](-[OH;D1;+0:10])-[CH2;D2;+0:9]-[N;H0;D3;+0:4](-[C:5]-[c:6])-[C:2](-[C:1])-[C;D1;H3:3] | null | [] | null | null | 40 | HOUR | After 40 hours' boiling and working up analogously to Example (4a), 22.4 g of 4-(2,3-epoxypropoxy)salicylic acid methyl ester and 30 g of 5-(2-benzylaminopropoxy)salicylamide in 200 ml of isopropanol yield crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethyl]benzylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)prop... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C(C)(C)O | null | 40 | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.COC(=O)c1ccc(OCC2CO2)cc1O>C(C)(C)O>COC(=O)c1ccc(OCC(O)CN(Cc2ccccc2)C(C)COc2ccc(O)c(C(N)=O)c2)cc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bdd53f2aa794405982b767a086f662bc | COC(=O)c1cccc(O)c1O.ClCCN(Cc1ccccc1)Cc1ccccc1>>COC(=O)c1cccc(OCCN(Cc2ccccc2)Cc2ccccc2)c1O | COC(C1=C(C(=CC=C1)O)O)=O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1>>COC(C=1C(O)=C(C=CC1)OCCN(CC1=CC=CC=C1)CC1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[c:28]1[OH:29].Cl[CH2:11][CH2:12][N:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17... | COC(=O)c1cccc(O)c1O.ClCCN(Cc1ccccc1)Cc1ccccc1 | COC(=O)c1cccc(OCCN(Cc2ccccc2)Cc2ccccc2)c1O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(CN(CCOc2ccccc2)Cc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 2,3-dihydroxybenzoic acid methyl ester is reacted in the presence of potassium carbonate in acetonitrile with 1.1 equivalents of 1-dibenzylamino-2-chloroethane for 18 hours at 82°. The crude 3-(2-dibenzylaminoethoxy)salicyclic acid methyl ester obtained after working up is put to further use without further purificatio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(C)#N | null | null | COC(=O)c1cccc(O)c1O.ClCCN(Cc1ccccc1)Cc1ccccc1>C(C)#N>COC(=O)c1cccc(OCCN(Cc2ccccc2)Cc2ccccc2)c1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4138b5976c30454da791ce9f725bb448 | COCCOc1ccc(OCC2CO2)cc1.NC(=O)c1cccc(OCCNCc2ccccc2)c1O>>COCCOc1ccc(OCC(O)CN(CCOc2cccc(C(N)=O)c2O)Cc2ccccc2)cc1 | O1C(COC2=CC=C(C=C2)OCCOC)C1.C(C1=CC=CC=C1)NCCOC1=C(C(C(=O)N)=CC=C1)O>>C(N)(=O)C=1C(=C(OCCN(CC(COC2=CC=C(C=C2)OCCOC)O)CC2=CC=CC=C2)C=CC1)O | [CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]2[O:13][CH2:14]2)[cH:36][cH:37]1.[NH:15]([CH2:16][CH2:17][O:18][c:19]1[cH:20][cH:21][cH:22][c:23]([C:24]([NH2:25])=[O:26])[c:27]1[OH:28])[CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]... | COCCOc1ccc(OCC2CO2)cc1.NC(=O)c1cccc(OCCNCc2ccccc2)c1O | COCCOc1ccc(OCC(O)CN(CCOc2cccc(C(N)=O)c2O)Cc2ccccc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc(CN(CCCOc2ccccc2)CCOc2ccccc2)cc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[c:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C:6]-[C:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[N;H0;D3;+0:3](-[C:2]-[C:1])-[C:4]-[c:5] | null | [] | null | null | null | null | By reacting 2.5 g of 1-(2,3-epoxypropoxy)-4-(2-methoxyethoxy)benzene with 2.9 g of crude 3-(2-benzylaminoethoxy)salicylamide obtained according to Example (25c), analogously to Example (4a), 1-[N-[2-(3-carbamoyl-2-hydroxyphenoxy)ethyl]benzylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol is obtained as an oil which is... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | COCCOc1ccc(OCC2CO2)cc1.NC(=O)c1cccc(OCCNCc2ccccc2)c1O>>COCCOc1ccc(OCC(O)CN(CCOc2cccc(C(N)=O)c2O)Cc2ccccc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-152204720d674800a0350d569265abe5 | C=CCBr.CC1(C)NC(=O)c2cc(O)ccc2O1>>C=CCOc1ccc2c(c1)C(=O)NC(C)(C)O2 | CC1(OC2=C(C(N1)=O)C=C(C=C2)O)C.C(C=C)Br.C([O-])([O-])=O.[K+].[K+]>>CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC=C)C | Br[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[O:17]2>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[O:17]2 | C=CCBr.CC1(C)NC(=O)c2cc(O)ccc2O1 | C=CCOc1ccc2c(c1)C(=O)NC(C)(C)O2 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1NCOc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A solution of 9.65 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one and 9.1 g of allyl bromide in 150 ml of acetonitrile is refluxed for 5 hours, whilst stirring, with the addition of 10.3 g of dry potassium carbonate. The reaction mixture is filtered whilst warm, the filtrate is concentrated by evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CNCO2 | HBr | C(C)#N | null | null | C=CCBr.CC1(C)NC(=O)c2cc(O)ccc2O1>C(C)#N>C=CCOc1ccc2c(c1)C(=O)NC(C)(C)O2 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2ae538c41730482c9160ea66680d7309 | COCCOc1ccc(OCC(O)CN(CCCCOc2ccc(O)c(C(N)=O)c2)Cc2ccccc2)cc1>>COCCOc1ccc(OCC(O)CNCCCCOc2ccc(O)c(C(N)=O)c2)cc1 | C(N)(=O)C=1C=C(OCCCCN(CC(COC2=CC=C(C=C2)OCCOC)O)CC2=CC=CC=C2)C=CC1O>>C(N)(=O)C=1C=C(OCCCCNCC(COC2=CC=C(C=C2)OCCOC)O)C=CC1O | c1ccc(C[N:15]([CH2:14][CH:12]([CH2:11][O:10][c:9]2[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:32][cH:31]2)[OH:13])[CH2:16][CH2:17][CH2:18][CH2:19][O:20][c:21]2[cH:22][cH:23][c:24]([OH:25])[c:26]([C:27]([NH2:28])=[O:29])[cH:30]2)cc1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12](... | COCCOc1ccc(OCC(O)CN(CCCCOc2ccc(O)c(C(N)=O)c2)Cc2ccccc2)cc1 | COCCOc1ccc(OCC(O)CNCCCCOc2ccc(O)c(C(N)=O)c2)cc1 | null | null | CO | Deprotection | Hydrogenolysis of tertiary amines | c7b12980b0925f19f153d220e0d23df430cf55f157d3497ce9d59af5c5715792 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(OCCCCNCCCOc2ccccc2)cc1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of 25 g of crude 1-[N-[4-(3-carbamoyl-4-hydroxyphenoxy)butyl]benzylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol in 250 ml of methanol is hydrogenated and worked up analogously to Example 4. The resulting crystalline crude product is recrystallised from isopropanol and yields 1-[4-(3-carbamoyl-4-hydroxyph... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | COCCOc1ccc(OCC(O)CN(CCCCOc2ccc(O)c(C(N)=O)c2)Cc2ccccc2)cc1>CO>COCCOc1ccc(OCC(O)CNCCCCOc2ccc(O)c(C(N)=O)c2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d6c6a7798fa54baab3dca6d9fadb6042 | N#Cc1ccccc1OCC1CO1.NCCCCc1ccc(O)c(C(N)=O)c1.O>>N#Cc1ccccc1OCC(O)CNCCCCOc1ccc(O)c(C(N)=O)c1 | O1C(COC2=C(C#N)C=CC=C2)C1.NCCCCC1=CC=C(C(C(=O)N)=C1)O.O>>C(N)(=O)C=1C=C(OCCCCNCC(COC2=C(C=CC=C2)C#N)O)C=CC1O | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH:11]1[O:12][CH2:13]1.[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][c:20]1[cH:21][cH:22][c:23]([OH:24])[c:25]([C:26]([NH2:27])=[O:28])[cH:29]1.[OH2:19]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH:11]([OH:12])[CH2:13][NH:14][CH2:15][CH2:16][CH... | N#Cc1ccccc1OCC1CO1.NCCCCc1ccc(O)c(C(N)=O)c1.O | N#Cc1ccccc1OCC(O)CNCCCCOc1ccc(O)c(C(N)=O)c1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 2383759c28423fe23dc3978d8f72631023d43d05d9999ec1b518cb56ec13023f | dfe0a3132ae2d4b52e59b1af4237b3e361ae8af87add3fd0f2cd99e5ed320ee8 | c1ccc(OCCCCNCCCOc2ccccc2)cc1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[N;D1;H2:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]:[c;H0;D3;+0:10](-[CH2;D2;+0:11]-[C:12]-[C:13]-[C:14]-[NH2;D1;+0:15]):[c:16]:[c:17].[OH2;D0;+0:18]>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[NH;D2;+0:15]-[C:14]-[C:13]-[C:12]-[CH2;D2;+0:11]-[O;H0;D2;+0:18]-[c;H0;D3;+0:10](:[c:16]:[c... | null | [] | null | null | 1 | HOUR | 7.3 g of 2-(2,3-epoxypropoxy)benzonitrile are added to a solution of 6.7 g of 5-(4-aminobutyl)salicylamide in 60 ml of dimethyl sulphoxide and the mixture is stirred for 1 hour in a bath at 90°. The reaction mixture is poured into 300 ml of water and extracted twice with 200 ml of ethyl acetate each time. Working up an... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Ether.Secondary alcohol.Secondary amine | C1CO1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | CS(=O)C | null | 1 | N#Cc1ccccc1OCC1CO1.NCCCCc1ccc(O)c(C(N)=O)c1.O>CS(=O)C>N#Cc1ccccc1OCC(O)CNCCCCOc1ccc(O)c(C(N)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-13fff069e6674f938ae4987e19fdf4d8 | CC(COc1ccc(C(N)=O)c(O)c1)N(Cc1ccccc1)CC(O)COc1ccc(NS(C)(=O)=O)cc1>>CC(COc1ccc(C(N)=O)c(O)c1)NCC(O)COc1ccc(NS(C)(=O)=O)cc1 | C(N)(=O)C1=C(C=C(OCC(C)N(CC(COC2=CC=C(C=C2)NS(=O)(=O)C)O)CC2=CC=CC=C2)C=C1)O>>C(N)(=O)C1=C(C=C(OCC(C)NCC(COC2=CC=C(C=C2)NS(=O)(=O)C)O)C=C1)O | c1ccc(C[N:15]([CH:2]([CH3:1])[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[c:12]([OH:13])[cH:14]2)[CH2:16][CH:17]([OH:18])[CH2:19][O:20][c:21]2[cH:22][cH:23][c:24]([NH:25][S:26]([CH3:27])(=[O:28])=[O:29])[cH:30][cH:31]2)cc1>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[c:12]([... | CC(COc1ccc(C(N)=O)c(O)c1)N(Cc1ccccc1)CC(O)COc1ccc(NS(C)(=O)=O)cc1 | CC(COc1ccc(C(N)=O)c(O)c1)NCC(O)COc1ccc(NS(C)(=O)=O)cc1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | c7b12980b0925f19f153d220e0d23df430cf55f157d3497ce9d59af5c5715792 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(OCCCNCCOc2ccccc2)cc1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4](-[C:5])-[C;D1;H3:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4](-[C:5])-[C;D1;H3:6] | null | [] | null | null | null | null | A solution of 20.0 g of crude 1-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethyl]-benzylamino]-3-(4-methanesulfonylamino-phenoxy)-2-propanol in 250 ml of methanol is hydrogenated, after the addition of 2.5 g of Pd/C catalyst (5%), under normal conditions until debenzylation is completed (DC control), for which an a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | [Pd].CO | null | null | CC(COc1ccc(C(N)=O)c(O)c1)N(Cc1ccccc1)CC(O)COc1ccc(NS(C)(=O)=O)cc1>[Pd].CO>CC(COc1ccc(C(N)=O)c(O)c1)NCC(O)COc1ccc(NS(C)(=O)=O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-00674f642fd141148364d4aaddd6f279 | NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O>>NC(=O)c1cc(OCCNCC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O | C(N)(=O)C=1C=C(OCCN(CC(COC2=CC=C(C=C2)CCOCC2CC2)O)CC2=CC=CC=C2)C=CC1O.[H][H]>>C(N)(=O)C=1C=C(OCCNCC(COC2=CC=C(C=C2)CCOCC2CC2)O)C=CC1O | c1ccc(C[N:10]([CH2:9][CH2:8][O:7][c:6]2[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:31]([OH:32])[cH:30][cH:29]2)[CH2:11][CH:12]([OH:13])[CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([CH2:20][CH2:21][O:22][CH2:23][CH:24]3[CH2:25][CH2:26]3)[cH:27][cH:28]2)cc1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][CH2:9][NH:10][CH2:11][C... | NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O | NC(=O)c1cc(OCCNCC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | c7b12980b0925f19f153d220e0d23df430cf55f157d3497ce9d59af5c5715792 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(OCCNCCCOc2ccc(CCOCC3CC3)cc2)cc1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of 30 g of crude 1-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-benzylamino]-3-[4-[2-(cyclopropylmethoxy)ethyl]-phenoxy]-2-propanol in 600 ml of methanol is hydrogenated, with the addition of 4 g of a Pd/C catalyst (5%), under normal conditions until 1 mol-equivalent of hydrogen has been absorbed. By the add... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1.C1CC1 | Other | [Pd].CO | null | null | NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O>[Pd].CO>NC(=O)c1cc(OCCNCC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-364286022957480fb90d4b28428360df | CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2>>CC(=O)COc1ccc(O)c(C(N)=O)c1 | CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)=O)C>>O=C(COC1=CC=C(C(C(=O)N)=C1)O)C | CC1(C)[O:10][c:9]2[cH:8][cH:7][c:6]([O:5][CH2:4][C:2]([CH3:1])=[O:3])[cH:15][c:11]2[C:12](=[O:14])[NH:13]1>>[CH3:1][C:2](=[O:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([C:12]([NH2:13])=[O:14])[cH:15]1 | CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2 | CC(=O)COc1ccc(O)c(C(N)=O)c1 | null | null | Cl.O1CCOCC1 | Deprotection | OtherReaction | 661fe1514f857633b73b0e1dad02767458f868ce5bca59d8faf17042ddb8af57 | 2902eb625a981761c5a520410afd09a992616e1a3bd271f13be71d300d901240 | c1ccccc1 | C-C1(-C)-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](:[c:6])-[O;H0;D2;+0:7]-1>>[NH2;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[OH;D1;+0:7]):[c:6] | null | [] | null | null | null | null | 74 g of the resulting 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one in a mixture of 150 ml of dioxane and 450 ml of 2N hydrochloric acid are heated for 45 minutes on a water bath. The solvent is evaporated off, and the crystalline residue is triturated with water and then filtered off with suction. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | Primary amide.Aromatic alcohol | c1ccc2c(c1)CNCO2 | null | c1ccccc1 | Other | Cl.O1CCOCC1 | null | null | CC(=O)COc1ccc2c(c1)C(=O)NC(C)(C)O2>Cl.O1CCOCC1>CC(=O)COc1ccc(O)c(C(N)=O)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fd0ebe5400be4198acdf81230619e204 | CC(=O)COc1ccc(O)c(C(N)=O)c1.NCc1ccccc1>>CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1 | [H][H].C(C1=CC=CC=C1)N.S(O)(O)(=O)=O.O=C(COC1=CC=C(C(C(=O)N)=C1)O)C>>C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C | O=[C:2]([CH3:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([NH2:12])=[O:13])[cH:14]1.[NH2:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([NH2:12])=[O:13])[cH:14]1)[NH:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(=O)COc1ccc(O)c(C(N)=O)c1.NCc1ccccc1 | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1 | null | [Pt] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CNCCOc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[#8:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | 55 g of benzylamine and 1.25 g of conc. sulfuric acid are added to a solution of 104.5 g of 5-(2-oxo-propoxy)salicylamide in 1000 ml of methanol, and the mixture is hydrogenated, in the presence of 3.0 g of a Pt/C catalyst under normal conditions until 1 equivalent of hydrogen has been absorbed. The catalyst is filtere... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pt].CO | null | null | CC(=O)COc1ccc(O)c(C(N)=O)c1.NCc1ccccc1>[Pt].CO>CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b95195d2cd784a148d1234c8bc6ee701 | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.c1cc(OCC2CO2)ccc1CCOCC1CC1>>NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O | C1(CC1)COCCC1=CC=C(C=C1)OCC1CO1.C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C>>C(N)(=O)C=1C=C(OCCN(CC(COC2=CC=C(C=C2)CCOCC2CC2)O)CC2=CC=CC=C2)C=CC1O | C[CH:9]([CH2:8][O:7][c:6]1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:38]([OH:39])[cH:37][cH:36]1)[NH:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[CH2:18]1[CH:19]([CH2:21][O:22][c:23]2[cH:24][cH:25][c:26]([CH2:27][CH2:28][O:29][CH2:30][CH:31]3[CH2:32][CH2:33]3)[cH:34][cH:35]2)[O:20]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5... | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.c1cc(OCC2CO2)ccc1CCOCC1CC1 | NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc(CN(CCCOc2ccc(CCOCC3CC3)cc2)CCOc2ccccc2)cc1 | C-[CH;D3;+0:1](-[C:2]-[#8:3])-[NH;D2;+0:4]-[C:5]-[c:6].[C:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:5]-[c:6])-[CH2;D2;+0:9]-[C:8](-[C:7])-[OH;D1;+0:10] | null | [] | null | null | null | null | A solution of 14.3 g of 1-[2-(cyclopropyl-methoxy)ethyl]-4-(2,3-epoxypropoxy)-benzene (German Offenlegungsschrift No. 2,649,605) and 16.3 g of 5-[2-(benzylamino)propoxy]-salicylamide in 200 ml of isopropanol is refluxed for 18 hours. The reaction mixture is concentrated by evaporation to leave crude 1-[N-[2-(3-carbamoy... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC1 | Other | C(C)(C)O | null | null | CC(COc1ccc(O)c(C(N)=O)c1)NCc1ccccc1.c1cc(OCC2CO2)ccc1CCOCC1CC1>C(C)(C)O>NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(CCOCC3CC3)cc2)ccc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a3fc75976eb84e38ac08b331292e5971 | NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(OCCO)cc2)ccc1O>>NC(=O)c1cc(OCCNCC(O)COc2ccc(OCCO)cc2)ccc1O | C(N)(=O)C=1C=C(OCCN(CC(COC2=CC=C(C=C2)OCCO)O)CC2=CC=CC=C2)C=CC1O.[H][H]>>C(N)(=O)C=1C=C(OCCNCC(COC2=CC=C(C=C2)OCCO)O)C=CC1O | c1ccc(C[N:10]([CH2:9][CH2:8][O:7][c:6]2[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:28]([OH:29])[cH:27][cH:26]2)[CH2:11][CH:12]([OH:13])[CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([O:20][CH2:21][CH2:22][OH:23])[cH:24][cH:25]2)cc1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][CH2:9][NH:10][CH2:11][CH:12]([OH:13])[CH2:14][O:1... | NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(OCCO)cc2)ccc1O | NC(=O)c1cc(OCCNCC(O)COc2ccc(OCCO)cc2)ccc1O | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | c7b12980b0925f19f153d220e0d23df430cf55f157d3497ce9d59af5c5715792 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(OCCCNCCOc2ccccc2)cc1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of 23 g of crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)ethyl]-benzylamino]-3-[4-(2-hydroxyethoxy)phenoxy]-2-propanol in 500 ml of methanol is hydrogenated, under normal conditions, with the addition of 2 g of 5% palladium on carbon catalyst, until hydrogen absorption has ceased. The catalyst is then removed ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | [Pd].CO | null | null | NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(OCCO)cc2)ccc1O>[Pd].CO>NC(=O)c1cc(OCCNCC(O)COc2ccc(OCCO)cc2)ccc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-74326da63a1b43b7b1f17eec13973a19 | ClCC1CO1.OCCOc1ccc(O)cc1>>OCCOc1ccc(OCC2CO2)cc1 | OCCOC1=CC=C(C=C1)O.C(Cl)C1CO1.C([O-])([O-])=O.[K+].[K+]>>O1C(COC2=CC=C(C=C2)OCCO)C1 | Cl[CH2:10][CH:11]1[CH2:12][O:13]1.[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:14][cH:15]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH:11]2[CH2:12][O:13]2)[cH:14][cH:15]1 | ClCC1CO1.OCCOc1ccc(O)cc1 | OCCOc1ccc(OCC2CO2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC2CO2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | null | null | With stirring, 13 g of crude 4-(2-hydroxyethoxy)phenol, 35 m of epichlorohydrin and 23.5 g of potassium carbonate are heated for 11/2 hours to reflux temperature. The reaction mixture is filtered and the filtrate is concentrated by evaporation under reduced pressure. The residual oil gradually congeals to a crystalline... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CO1 | HCl | null | null | null | ClCC1CO1.OCCOc1ccc(O)cc1>>OCCOc1ccc(OCC2CO2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-56876a15c54c4de4818fa1eeae7b7038 | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.CI>>CCOC(=O)c1cn(C)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O.C([O-])([O-])=O.[K+].[K+].CI>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C)C(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:10]2[cH:11][c:12](-[n:13]3[cH:14][cH:15][cH:16][cH:17]3)[c:18]([F:19])[cH:20][c:21]2[c:22]1[OH:23].I[CH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH3:9])[c:10]2[cH:11][c:12](-[n:13]3[cH:14][cH:15][cH:16][cH:17]3)[c:18]([F:19])[cH:20][c:21]2[c:22]1=[O:23] | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.CI | CCOC(=O)c1cn(C)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | CN(C=O)C | Acylation | OtherReaction | 141cc6b0b1f246b2bc40e33f6ee5f70d3157f77fa765a089a7aee4950b06efc7 | 112bab89a832807e83a4911f32b3895489765458263eca889524c8ed19f7b9da | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | I-[CH3;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[n;H0;D2;+0:8]:[c:9](:[c:10]):[c:11](:[c:12]):[c;H0;D3;+0:13]:1-[OH;D1;+0:14]>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[n;H0;D3;+0:8](-[CH3;D1;+0:1]):[c:9](:[c:10]):[c:11](:[c:12]):[c;H0;D3;+0:13]:1=[O;H0;D1;+0:14] | 76.4 | [{"value": 76.4, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 1.5 g (0.005 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 1.4 g (0.01 mol) of potassium carbonate in 10 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 2.15 g (3×0.005 mol) of methyl iodide are added, the mixture is heated at 80°-90° C. for 4 hour... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cc[nH]c1 | HI | CN(C=O)C | 60 | null | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.CI>CN(C=O)C>CCOC(=O)c1cn(C)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5aa3d23c953f421bba97f65963e5ba38 | CCOC(=O)c1cn(C)c2cc(-n3cccc3)c(F)cc2c1=O>>Cn1cc(C(=O)O)c(=O)c2cc(F)c(-n3cccc3)cc21 | Cl.FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C)C(=O)OCC)=O.C(C)O.[OH-].[Na+]>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C)C(=O)O)=O | CC[O:7][C:5]([c:4]1[cH:3][n:2]([CH3:1])[c:21]2[c:10]([c:8]1=[O:9])[cH:11][c:12]([F:13])[c:14](-[n:15]1[cH:16][cH:17][cH:18][cH:19]1)[cH:20]2)=[O:6]>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8](=[O:9])[c:10]2[cH:11][c:12]([F:13])[c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21]12 | CCOC(=O)c1cn(C)c2cc(-n3cccc3)c(F)cc2c1=O | Cn1cc(C(=O)O)c(=O)c2cc(F)c(-n3cccc3)cc21 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 68.6 | [{"value": 68.6, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.2 g of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate, 10 ml of ethanol, 15 ml of 10% sodium hydroxide solution and 10 ml of water is heated under reflux for 2 hours. 30 ml of 8M hydrochloric acid are added, the mixture is left to cool and the product is filtered off, wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1.c1cc[nH]c1 | Other | O | null | null | CCOC(=O)c1cn(C)c2cc(-n3cccc3)c(F)cc2c1=O>O>Cn1cc(C(=O)O)c(=O)c2cc(F)c(-n3cccc3)cc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d71e37624aff4110a72e833bc5f49268 | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.OCCBr>>CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O.C([O-])([O-])=O.[K+].[K+].C(CO)Br>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCO)C(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[c:20]([F:21])[cH:22][c:23]2[c:24]1[OH:25].Br[CH2:9][CH2:10][OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][CH2:10][OH:11])[c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[c:20]([F:2... | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.OCCBr | CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | CN(C=O)C | Acylation | OtherReaction | e80027ca46b6efa11719ae5e345757a72e21785d9f10a526dcedbc5985f6dbf4 | 1ace3814128badf62d481904cb0fc2463e51f1c5bfb35fa1f883a03bb843d915 | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[OH;D1;+0:16]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[n;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3]):[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1=[O;H0;D1;+0:... | 45.9 | [{"value": 45.9, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCO)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 2 g (0.0076 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-caboxylate and 1.85 g (2×0.0076 mol) of potassium carbonate in 20 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 3.35 g (4×0.0076 mol) of ethylene bromohydrin are added, the mixture is heated at 80°-90° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cc[nH]c1 | HBr | CN(C=O)C | 60 | null | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.OCCBr>CN(C=O)C>CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6b9597b166164c3394f566c446f2efe8 | CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cn(CCCl)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCO)C(=O)OCC)=O.P(=O)(Cl)(Cl)Cl>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCCl)C(=O)OCC)=O | O[CH2:10][CH2:9][n:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:24](=[O:25])[c:23]2[c:12]1[cH:13][c:14](-[n:15]1[cH:16][cH:17][cH:18][cH:19]1)[c:20]([F:21])[cH:22]2.O=P(Cl)(Cl)[Cl:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][CH2:10][Cl:11])[c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19... | CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O.O=P(Cl)(Cl)Cl | CCOC(=O)c1cn(CCCl)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_POCl3 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[#7;a:4]>>[#7;a:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | null | [] | null | null | 2 | HOUR | 3.5 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate are suspended in 30 ml chloroform, 3 ml of Cl3PO are added, the mixture is kept at room temperature for 2 hours and evaporated to dryness, the residue is redissolved in chloroform, the resulting solution is wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2ncccc2c1.c1cc[nH]c1 | HCl | C(Cl)(Cl)Cl | null | 2 | CCOC(=O)c1cn(CCO)c2cc(-n3cccc3)c(F)cc2c1=O.O=P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>CCOC(=O)c1cn(CCCl)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fd0d21daeb32407586c452e4c390cba8 | BrCC1CC1.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O>>CCOC(=O)c1cn(CC2CC2)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O.C([O-])([O-])=O.[K+].[K+].C1(CC1)CBr>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CC1CC1)C(=O)OCC)=O | Br[CH2:9][CH:10]1[CH2:11][CH2:12]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:13]2[cH:14][c:15](-[n:16]3[cH:17][cH:18][cH:19][cH:20]3)[c:21]([F:22])[cH:23][c:24]2[c:25]1[OH:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][CH:10]2[CH2:11][CH2:12]2)[c:13]2[cH:14][c:15](-[n:16]3[cH:17][cH:18][cH:19]... | BrCC1CC1.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O | CCOC(=O)c1cn(CC2CC2)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | CN(C=O)C | Acylation | OtherReaction | e80027ca46b6efa11719ae5e345757a72e21785d9f10a526dcedbc5985f6dbf4 | 1ace3814128badf62d481904cb0fc2463e51f1c5bfb35fa1f883a03bb843d915 | O=c1ccn(CC2CC2)c2cc(-n3cccc3)ccc12 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[n;H0;D2;+0:11]:[c:12](:[c:13]):[c:14](:[c:15]):[c;H0;D3;+0:16]:1-[OH;D1;+0:17]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2]2-[C:3]-[C:4]-2):[c:12](:[c:13]):[c:14](:[c:15]):[c;H0;D3;+0:16]:1=[O;H... | 62.3 | [{"value": 62.3, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CC1CC1)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | A mixture of 3.6 g (0.012 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 4.15 g (0.03 mol) of potassium carbonate in 30 ml of dimethlformamide is heated for 30 minutes at 80° C. and left to cool, 8 g (0.06 mol) of cyclopropylmethyl bromide are added, the mixture is kept for 12 hours at 90° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC1.c1ccc2ncccc2c1.c1cc[nH]c1 | HBr | CN(C=O)C | 80 | 12 | BrCC1CC1.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O>CN(C=O)C>CCOC(=O)c1cn(CC2CC2)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-be0c48a785594e99ae9be16e912872eb | CCCBr.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O>>CCCn1cc(C(=O)OCC)c(=O)c2cc(F)c(-n3cccc3)cc21 | FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O.C([O-])([O-])=O.[K+].[K+].CCCBr>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCC)C(=O)OCC)=O | Br[CH2:3][CH2:2][CH3:1].[n:4]1[cH:5][c:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]([OH:13])[c:14]2[cH:15][c:16]([F:17])[c:18](-[n:19]3[cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25]12>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][c:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12](=[O:13])[c:14]2[cH:15][c:16]([F:17])[c:18](-[n:19]3[cH:20... | CCCBr.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O | CCCn1cc(C(=O)OCC)c(=O)c2cc(F)c(-n3cccc3)cc21 | null | null | O | Acylation | OtherReaction | e80027ca46b6efa11719ae5e345757a72e21785d9f10a526dcedbc5985f6dbf4 | 1ace3814128badf62d481904cb0fc2463e51f1c5bfb35fa1f883a03bb843d915 | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | Br-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[OH;D1;+0:16]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[n;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3]):[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1=[O;H0;D1;+0:... | 70.1 | [{"value": 70.1, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCC)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate, 2.8 g (0.02 mol) of potassium carbonate and 6 g (0.04 mol) of n-propyl bromide is heated for 5 hours at 80°-90° C. and left to cool, water is added and the precipitate formed is filtered off, washed with water and recrystall... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cc[nH]c1 | HBr | O | null | null | CCCBr.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O>O>CCCn1cc(C(=O)OCC)c(=O)c2cc(F)c(-n3cccc3)cc21 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-961546021a8f448e97a2a1b9f8a02a55 | CC(F)Br.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O>>CCOC(=O)c1cn(C(C)F)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O.C([O-])([O-])=O.[K+].[K+].BrC(C)F>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C(C)F)C(=O)OCC)=O | Br[CH:9]([CH3:10])[F:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[c:20]([F:21])[cH:22][c:23]2[c:24]1[OH:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]([CH3:10])[F:11])[c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[c:20]([F:2... | CC(F)Br.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O | CCOC(=O)c1cn(C(C)F)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | CN(C=O)C | Acylation | OtherReaction | 26e2764f6349b1245ccb983aab344ab3d7453f5246ffb0f41168acc036813e28 | 2deb21a7840c572d064e3e4d240974ef5f59a93f77954a133a0dbf85fe46db9d | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[F;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[OH;D1;+0:16]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[n;H0;D3;+0:10](-[CH;D3;+0:1](-[C;D1;H3:2])-[F;D1;H0:3]):[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:... | 61.7 | [{"value": 61.7, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C(C)F)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 7 | HOUR | A mixture of 3.2 g (0.011 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 4 g (2.5×0.011 mol) of potassium carbonate in 20 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 7 g (5×0.011 mol) of bromofluoroethane are added, the mixture is kept for 7 hours at 80° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Aromatic alcohol | Secondary halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cc[nH]c1 | HBr | CN(C=O)C | 60 | 7 | CC(F)Br.CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O>CN(C=O)C>CCOC(=O)c1cn(C(C)F)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-26cbc7a835c94c10aedfdc353735302f | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1>>CCOC(=O)c1cn(N)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O.C([O-])([O-])=O.[K+].[K+].[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])NO>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)N)C(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:10]2[cH:11][c:12](-[n:13]3[cH:14][cH:15][cH:16][cH:17]3)[c:18]([F:19])[cH:20][c:21]2[c:22]1[OH:23].O=[N+]([O-])c1ccc(NO)c([N+:9](=O)[O-])c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([NH2:9])[c:10]2[cH:11][c:12](-[n:13]3[cH:14][cH:15][cH:16][cH:17]3)[c:18]([F:... | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1 | CCOC(=O)c1cn(N)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | CN(C=O)C | Acylation | OtherReaction | a12ee36d9722483abad7fdb9f97ec4f6fa412f5f0bcb89db0c911c01310df9c5 | f3e640ef0cc3e392b2a1f4cf1d9f505e95083c74f398b27b5b948d2133c880ac | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | O-N-c1:c:c:c(-[N+](=O)-[O-]):c:c:1-[N+;H0;D3:1](=O)-[O-].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[n;H0;D2;+0:8]:[c:9](:[c:10]):[c:11](:[c:12]):[c;H0;D3;+0:13]:1-[OH;D1;+0:14]>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[n;H0;D3;+0:8](-[NH2;D1;+0:1]):[c:9](:[c:10]):[c:11](:[c:12]):[c;H0;D3;+0:13]:1=[O;H0;D1;+0:... | 23.8 | [{"value": 23.8, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)N)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 24 | HOUR | A mixture of 6 g (0.02 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate and 5.6 g (0.04 mol) of potassium carbonate in 80 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 8.5 g (0.042 mol) of 2,4-dinitrophenylhydroxylamine are added, the mixture is kept for 24 hours at... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group.Aromatic alcohol.Secondary amine | Primary amine | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cc[nH]c1 | HO- | CN(C=O)C | 60 | 24 | CCOC(=O)c1cnc2cc(-n3cccc3)c(F)cc2c1O.O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1>CN(C=O)C>CCOC(=O)c1cn(N)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8adc3019916d41df93e9978debdaa4cb | CC(=O)OC(C)=O.CCOC(=O)c1cn(N)c2cc(-n3cccc3)c(F)cc2c1=O>>CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)N)C(=O)OCC)=O.C(C)(=O)OC(C)=O>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)NC=O)C(=O)OCC)=O | CC(=O)O[C:10](C)=[O:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([NH2:9])[c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[c:20]([F:21])[cH:22][c:23]2[c:24]1=[O:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([NH:9][CH:10]=[O:11])[c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[c:20... | CC(=O)OC(C)=O.CCOC(=O)c1cn(N)c2cc(-n3cccc3)c(F)cc2c1=O | CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | C(=O)O | Acylation | OtherReaction | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | C-C(=O)-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[NH2;D1;+0:3]-[#7;a:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[#7;a:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | null | null | A solution of 3.15 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-amino-4-oxo-1,4-dihydroquinoline-3-carboxylate in 25 ml of formic acid is added dropwise to a mixture of 9.5 ml (0.01 mol) of acetic anhydride and 4 ml (0.01 mol) of formic acid, cooled to 0° C., the addition being carried out so as to maintain room te... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccc2ncccc2c1.c1cc[nH]c1 | HO- | C(=O)O | 0 | null | CC(=O)OC(C)=O.CCOC(=O)c1cn(N)c2cc(-n3cccc3)c(F)cc2c1=O>C(=O)O>CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a25eb7b5f55f482ab43f2e9c4ec90170 | CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O.CI>>CCOC(=O)c1cn(NCC=O)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)NC=O)C(=O)OCC)=O.C([O-])([O-])=O.[K+].[K+].CI>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)NCC=O)C(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([NH:9][CH:11]=[O:12])[c:13]2[cH:14][c:15](-[n:16]3[cH:17][cH:18][cH:19][cH:20]3)[c:21]([F:22])[cH:23][c:24]2[c:25]1=[O:26].I[CH3:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([NH:9][CH2:10][CH:11]=[O:12])[c:13]2[cH:14][c:15](-[n:16]3[cH:17][cH:18][cH:19][cH:20]... | CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O.CI | CCOC(=O)c1cn(NCC=O)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | CN(C=O)C | C-C Coupling | OtherReaction | f2088841e4ff4a0ed964245d0643ba9fa2a35bccb64c0cfae5ec144f60486d33 | dbb88e10ee36ed59beb374cee68ffa8c8d7fa2a34f779ee8bf45b81ba6545809 | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[CH;D2;+0:3]-[NH;D2;+0:4]-[#7;a:5](:[c:6]):[c:7]>>[O;D1;H0:2]=[CH;D2;+0:3]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[#7;a:5](:[c:6]):[c:7] | 40 | [{"value": 40.0, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)NCC=O)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 35 | CELSIUS | 3 | HOUR | A mixture of 3.47 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate and 3 g (~0.02 mol) of potassium carbonate in 25 ml of dimethylformamide is heated for 10 minutes at 35° C. It is kept at room temperature for 2 hours in a partially precipitated state, 4.3 g (0.03 mo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Aldehyde.Secondary amine | null | null | c1ccc2ncccc2c1.c1cc[nH]c1 | HI | CN(C=O)C | 35 | 3 | CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O.CI>CN(C=O)C>CCOC(=O)c1cn(NCC=O)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7771b7d4dfd64e73b2d9da266949289a | CCI.CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O>>CCOC(=O)c1cn(NC(C)C=O)c2cc(-n3cccc3)c(F)cc2c1=O | FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)NC=O)C(=O)OCC)=O.C([O-])([O-])=O.[K+].[K+].C(C)I>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)NC(C)C=O)C(=O)OCC)=O | I[CH2:10][CH3:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([NH:9][CH:12]=[O:13])[c:14]2[cH:15][c:16](-[n:17]3[cH:18][cH:19][cH:20][cH:21]3)[c:22]([F:23])[cH:24][c:25]2[c:26]1=[O:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([NH:9][CH:10]([CH3:11])[CH:12]=[O:13])[c:14]2[cH:15][c:16](-[n:17]3[cH:18][cH:... | CCI.CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O | CCOC(=O)c1cn(NC(C)C=O)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 86e111b3210c84427f691a9a1271e3566662bace168334e06d4f7ae7843bcfab | ad7877b6b513505adbfe83191b42a8e1c6b89ac9523846ac59a04bfd75ec73e0 | O=c1cc[nH]c2cc(-n3cccc3)ccc12 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[CH;D2;+0:4]-[NH;D2;+0:5]-[#7;a:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[CH;D3;+0:1](-[CH;D2;+0:4]=[O;D1;H0:3])-[NH;D2;+0:5]-[#7;a:6](:[c:7]):[c:8] | 37.7 | [{"value": 37.7, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)NC(C)C=O)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 1.5 g (0.005 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate and 1.3 g (0.01 mol) of potassium carbonate in 10 ml of dimethylformamide is stirred for 3 hours at room temperature, 2.35 g (0.015 mol) of ethyl iodide are then added and the mixture is kept for 4 ho... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Aldehyde.Secondary amine | null | null | c1ccc2ncccc2c1.c1cc[nH]c1 | HI | CN(C=O)C | null | 3 | CCI.CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O>CN(C=O)C>CCOC(=O)c1cn(NC(C)C=O)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dc223d62d465498286c60c57753211e7 | COC1(OC)CCCO1.Nc1cc(F)c(C(=O)O)cc1F>>O=C(O)c1cc(F)c(-n2cccc2)cc1F | FC1=C(C(=O)O)C=C(C(=C1)N)F.COC1(OCCC1)OC.O>>FC1=C(C(=O)O)C=C(C(=C1)N1C=CC=C1)F | CO[C:10]1(OC)O[CH2:13][CH2:12][CH2:11]1.[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([NH2:9])[cH:14][c:15]1[F:16]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8](-[n:9]2[cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]1[F:16] | COC1(OC)CCCO1.Nc1cc(F)c(C(=O)O)cc1F | O=C(O)c1cc(F)c(-n2cccc2)cc1F | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 0e9d22b0723ec2930c6f0b28cb06c2d86835df697b962917265b2a52889a76e9 | 37da407ba22aeb87f9320448e7710117027e549cd7c89e722598c54789c5481f | c1ccc(-n2cccc2)cc1 | C-O-[C;H0;D4;+0:1]1(-O-C)-O-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[F;D1;H0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[NH2;D1;+0:9]):[c:10]:[c:11]>>[F;D1;H0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[n;H0;D3;+0:9]1:[cH;D2;+0:1]:[cH;D2;+0:4]:[cH;D2;+0:3]:[cH;D2;+0:2]:1):[c:10]:[c:11] | 79.2 | [{"value": 79.2, "product": "FC1=C(C(=O)O)C=C(C(=C1)N1C=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.2 grams (0.03 mol) of 2,5-difluoro-4-aminobenzoic acid, melting at 250°-3°, are dissolved in 60 ml of glacial acetic acid, and 4 grams (0.03 mol) of dimethoxytetrahydrofuran are added. The mixture is heated at the boil for 10 minutes, 20 ml of water are added and the resulting mixture is left to cool. The precipitate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine | null | C1CCOC1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | HO- | C(C)(=O)O | null | null | COC1(OC)CCCO1.Nc1cc(F)c(C(=O)O)cc1F>C(C)(=O)O>O=C(O)c1cc(F)c(-n2cccc2)cc1F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a4b80bde42b64cf99f5959c49c2e964f | CCOC(=O)CC(=O)c1cc(F)c(-n2cccc2)cc1F.NC1CC1>>CCOC(=O)C(=CNC1CC1)C(=O)c1cc(F)c(-n2cccc2)cc1F | C(OCC)([O-])[O-].FC1=C(C(=O)CC(=O)OCC)C=C(C(=C1)N1C=CC=C1)F.C1(CC1)N>>C1(CC1)NC=C(C(=O)OCC)C(C1=C(C=C(C(=C1)F)N1C=CC=C1)F)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18](-[n:19]2[cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1[F:26].[NH2:8][CH:9]1[CH2:10][CH2:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][NH:8][CH:9]1[CH2:10][CH2:11]1)[C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18](-[n:19]2[cH:2... | CCOC(=O)CC(=O)c1cc(F)c(-n2cccc2)cc1F.NC1CC1 | CCOC(=O)C(=CNC1CC1)C(=O)c1cc(F)c(-n2cccc2)cc1F | null | null | C(C)(=O)OC(C)=O | Heteroatom Alkylation and Arylation | OtherReaction | 2308c5562a388f5a3972b1c218a1d28a1c29d68e0019b4c583e0642f86effe2c | 386abf15293513363decea2e36c34c5591e7bebcecf634963fbfb09ec1e3b1bc | O=C(C=CNC1CC1)c1ccc(-n2cccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8].[NH2;D1;+0:9]-[C:10]1-[C:11]-[C:12]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[C:13]-[NH;D2;+0:9]-[C:10]1-[C:11]-[C:12]-1)-[C:6](=[O;D1;H0:7])-[c:8] | 36.1 | [{"value": 36.1, "product": "C1(CC1)NC=C(C(=O)OCC)C(C1=C(C=C(C(=C1)F)N1C=CC=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1 g (0.0068 mol) of ethyl orthoformate is added to a solution of 1.1 g (0.00315 mol) of ethyl 2,5-difluoro-4-(pyrrol-1-yl)benzoylacetate in 3 ml of acetic anhydride and the mixture is refluxed for 3 hours. It is evaporated to dryness, the residue is dissolved in 10 ml of ethanol, 0.3 ml (0.0034 mol) of cyclopropylamine... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Enamine | null | null | C1CC1.c1ccccc1.c1cc[nH]c1 | Other | C(C)(=O)OC(C)=O | null | 1 | CCOC(=O)CC(=O)c1cc(F)c(-n2cccc2)cc1F.NC1CC1>C(C)(=O)OC(C)=O>CCOC(=O)C(=CNC1CC1)C(=O)c1cc(F)c(-n2cccc2)cc1F |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0a1010327ec546d5a8e17196d15dca2f | CCOC(=O)C(=CNC1CC1)C(=O)c1cc(F)c(-n2cccc2)cc1F>>CCOC(=O)c1cn(C2CC2)c2cc(-n3cccc3)c(F)cc2c1=O | O.[H-].[Na+].C1(CC1)NC=C(C(=O)OCC)C(C1=C(C=C(C(=C1)F)N1C=CC=C1)F)=O>>FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C1CC1)C(=O)OCC)=O | F[c:12]1[cH:13][c:14](-[n:15]2[cH:16][cH:17][cH:18][cH:19]2)[c:20]([F:21])[cH:22][c:23]1[C:24]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][NH:8][CH:9]1[CH2:10][CH2:11]1)=[O:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11]2)[c:12]2[cH:13][c:14](-[n:15]3[cH:16][cH:17][cH:18][cH:19]3)[c:20... | CCOC(=O)C(=CNC1CC1)C(=O)c1cc(F)c(-n2cccc2)cc1F | CCOC(=O)c1cn(C2CC2)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | f1bb464adea8e64c138d384f2f02c35f1978964fc9c160676d8ef60c68e5e3df | ecabf5a50b4453255d534845e8b1084d96a0aaf957abdb24947c6089ec559e5f | O=c1ccn(C2CC2)c2cc(-n3cccc3)ccc12 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](=[CH;D2;+0:8]-[NH;D2;+0:9]-[C:10]1-[C:11]-[C:12]-1)-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]):[c:17]>>[C:16]-[#8:15]-[C:13](=[O;D1;H0:14])-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D3;+0:9](-[C:10]2-[C:11]-[C:12]-2):[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4... | 77.3 | [{"value": 77.3, "product": "FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C1CC1)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 0.07 g (0.00115 mol) of a 60% suspension of sodium hydride in mineral oil is added to a solution of 0.41 g (0.00114 mol) of ethyl 3-cyclopropylamino-2-(2,5-difluoro-4-pyrrol-1-ylbenzoyl)acrylate in 10 ml of anhydrous dioxane. The mixture is heated at 80° C. for 2 hours under a nitrogen atmosphere and left to cool, 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone | Ester | c1ccccc1 | c1ccc2ncccc2c1 | C1CC1.c1ccc2ncccc2c1.c1cc[nH]c1 | HF | O1CCOCC1 | 80 | null | CCOC(=O)C(=CNC1CC1)C(=O)c1cc(F)c(-n2cccc2)cc1F>O1CCOCC1>CCOC(=O)c1cn(C2CC2)c2cc(-n3cccc3)c(F)cc2c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-87a034d6b92e4c48b13cd6d203a3de37 | NCCc1ccc(O)c(O)c1.O=C(O)c1cccnc1>>O=C(NCCc1ccc(O)c(O)c1)c1cccnc1 | Br.NCCC1=CC(O)=C(O)C=C1.C(C1=CN=CC=C1)(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C1=CN=CC=C1)(=O)NCCC1=CC(O)=C(O)C=C1 | [NH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([OH:12])[cH:13]1.O[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([OH:12])[cH:13]1)[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1 | NCCc1ccc(O)c(O)c1.O=C(O)c1cccnc1 | O=C(NCCc1ccc(O)c(O)c1)c1cccnc1 | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccccc1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 70 | [{"value": 70.0, "product": "C(C1=CN=CC=C1)(=O)NCCC1=CC(O)=C(O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a pyridine solution containing 11.7 g (0.05 mol) dopamine hydrobromide and 6.15 g (0.05 mol) nicotinic acid at 0° C. were added 10.3 g (0.05 mol) dicyclohexylcarbodiimide (DCC). The reaction mixture was stirred at room temperature for 24 hours and the formed dicyclohexylurea was removed by filtration. The pyridine w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | N1=CC=CC=C1 | null | 24 | NCCc1ccc(O)c(O)c1.O=C(O)c1cccnc1>N1=CC=CC=C1>O=C(NCCc1ccc(O)c(O)c1)c1cccnc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-77996068530445938300e4a357205a17 | CC(=O)Oc1ccc(CCNC(=O)c2cccnc2)cc1OC(C)=O.CI>>CC(=O)Oc1ccc(CCNC(=O)c2ccc[n+](C)c2)cc1OC(C)=O.[I-] | C(C)(=O)OC=1C=C(C=CC1OC(C)=O)CCNC(=O)C=1C=NC=CC1.C(C)(=O)OC=1C=C(C=CC1OC(C)=O)CCNC(=O)C=1C=NC=CC1.CI>>[I-].C[N+]1=CC(=CC=C1)C(NCCC1=CC(=C(C=C1)OC(C)=O)OC(C)=O)=O | [CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:20]2)[cH:21][c:22]1[O:23][C:24]([CH3:25])=[O:26].[CH3:19][I:27]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][n+:18]([CH3:19])... | CC(=O)Oc1ccc(CCNC(=O)c2cccnc2)cc1OC(C)=O.CI | CC(=O)Oc1ccc(CCNC(=O)c2ccc[n+](C)c2)cc1OC(C)=O.[I-] | null | null | CO | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C(NCCc1ccccc1)c1ccc[nH+]c1 | [#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[n;H0;D2;+0:6]:[c:7]:[c:8].[CH3;D1;+0:9]-[I;H0;D1;+0:10]>>[#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[n+;H0;D3:6](-[CH3;D1;+0:9]):[c:7]:[c:8].[I-;H0;D0:10] | null | [] | null | null | null | null | To a solution of 1.71 g (5 mmol) of 3-{N-[β-(3,4-diacetoxyphenyl)ethyl]}carbamoylpyridine (prepared like compound 8c), 1.41 g (10 mmol) of methyl iodide were added and the mixture was refluxed overnight under stirring. The acetone solution was then decanted from the insoluble oily residue. Ether was added to the aceton... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1 | null | CO | null | null | CC(=O)Oc1ccc(CCNC(=O)c2cccnc2)cc1OC(C)=O.CI>CO>CC(=O)Oc1ccc(CCNC(=O)c2ccc[n+](C)c2)cc1OC(C)=O.[I-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-637be44371d74ee394c7fcecade573e7 | CI.C[n+]1cccc(C(=O)NCCc2ccc(O)c(O)c2)c1>>COc1cc(CCNC(=O)c2ccc[n+](C)c2)ccc1O | CI.[I-].C[N+]1=CC(=CC=C1)C(NCCC1=CC(=C(C=C1)O)O)=O.COC=1C=C(CCN)C=CC1O>>[I-].C[N+]1=CC(=CC=C1)C(NCCC1=CC(=C(C=C1)O)OC)=O | I[CH3:1].[OH:2][c:3]1[cH:4][c:5]([CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n+:15]([CH3:16])[cH:17]2)[cH:18][cH:19][c:20]1[OH:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n+:15]([CH3:16])[cH:17]2)[cH:18][cH:19][c:20]1[OH:21] | CI.C[n+]1cccc(C(=O)NCCc2ccc(O)c(O)c2)c1 | COc1cc(CCNC(=O)c2ccc[n+](C)c2)ccc1O | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=C(NCCc1ccccc1)c1ccc[nH+]c1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | N-nicotinoyl-3-methoxytyramine was prepared by following the procedure used for the preparation of compound 7. The isolated crude amide was quaternized directly with methyl iodide following the method used for the preparation of compound 6a. Crystallization from methanol gave a yellow crystalline compound, m.p. 192°-19... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1.C1=CC=[NH+]C=C1 | HI | null | null | null | CI.C[n+]1cccc(C(=O)NCCc2ccc(O)c(O)c2)c1>>COc1cc(CCNC(=O)c2ccc[n+](C)c2)ccc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c54d5e7c4e7f4a898b89558681cf48a2 | CN1C=CCC(C(=O)NCCc2ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c2)=C1>>COc1cc(CCNC(=O)C2=CN(C)C=CC2)ccc1O | CN1C=C(CC=C1)C(NCCC1=CC(=C(C=C1)OC(C(C)(C)C)=O)OC(C(C)(C)C)=O)=O.[2H]C(Cl)(Cl)Cl.[2H]O[2H]>>CN1C=C(CC=C1)C(NCCC1=CC(=C(C=C1)O)OC)=O | CC(C)(C)C(=O)[O:21][c:20]1[c:3]([O:2][C:1](=O)C(C)(C)C)[cH:4][c:5]([CH2:6][CH2:7][NH:8][C:9](=[O:10])[C:11]2=[CH:12][N:13]([CH3:14])[CH:15]=[CH:16][CH2:17]2)[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][CH2:7][NH:8][C:9](=[O:10])[C:11]2=[CH:12][N:13]([CH3:14])[CH:15]=[CH:16][CH2:17]2)[cH:18][cH:19][c:20]1[OH:2... | CN1C=CCC(C(=O)NCCc2ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c2)=C1 | COc1cc(CCNC(=O)C2=CN(C)C=CC2)ccc1O | null | null | null | Reduction | OtherReaction | 3aaec01a757f6ee96f4e498accfe9ee1eec22fb55b0666b8badf3cee4f881de8 | d41c8338d019a82cc53bc6a399f2c9810e585063f17bc036da4bb6cb6518b4ee | O=C(NCCc1ccccc1)C1=CNC=CC1 | C-C(-C)(-C)-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#8:5]-[C;H0;D3;+0:6](=O)-C(-C)(-C)-C>>[CH3;D1;+0:6]-[#8:5]-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | null | null | This compound was prepared following the same method as for the preparation of compound 5c. The crude solid obtained showed the same NMR (CDCl3 /D2O) pattern as compound 5a, except for a peak at δ 3.5 for the OCH3 protons. It was sufficiently pure for the determination of its retention time following the HPLC method of... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ether.Aromatic alcohol | null | null | c1ccccc1.C1=C[NH]C=CC1 | HO- | null | null | null | CN1C=CCC(C(=O)NCCc2ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c2)=C1>>COc1cc(CCNC(=O)C2=CN(C)C=CC2)ccc1O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-04d2f43c51074e648143c6e7a24764f5 | CI.O=C(NCCc1ccc(O)c(O)c1)c1cccnc1>>C[n+]1cccc(C(=O)NCCc2ccc(O)c(O)c2)c1.[I-] | CI.C(C1=CN=CC=C1)(=O)NCCC1=CC(O)=C(O)C=C1.CI>>[I-].C[N+]1=CC(=CC=C1)C(NCCC1=CC(=C(C=C1)O)O)=O | [CH3:1][I:21].[n:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([OH:16])[c:17]([OH:18])[cH:19]2)[cH:20]1>>[CH3:1][n+:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([OH:16])[c:17]([OH:18])[cH:19]2)[cH:20]1.[I-:21] | CI.O=C(NCCc1ccc(O)c(O)c1)c1cccnc1 | C[n+]1cccc(C(=O)NCCc2ccc(O)c(O)c2)c1.[I-] | null | null | CO | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C(NCCc1ccccc1)c1ccc[nH+]c1 | [#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[n;H0;D2;+0:6]:[c:7]:[c:8].[CH3;D1;+0:9]-[I;H0;D1;+0:10]>>[#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[n+;H0;D3:6](-[CH3;D1;+0:9]):[c:7]:[c:8].[I-;H0;D0:10] | null | [] | null | null | 6 | HOUR | To a solution of 2 g (7.7 mmol) of nicotinoyldopamine in 40 ml of dry methanol were added 2.5 g (17.6 mmol) of methyl iodide. The reaction mixture was refluxed with stirring for 6 hours. Methyl iodide (1.5 g, 1.05 mmol) was added and refluxing was continued overnight. Methanol was removed and ethyl acetate was added, a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1ccccc1 | null | CO | null | 6 | CI.O=C(NCCc1ccc(O)c(O)c1)c1cccnc1>CO>C[n+]1cccc(C(=O)NCCc2ccc(O)c(O)c2)c1.[I-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-89d1bfc898564179b23ca71c5e80d62f | CC(C)C(=O)Oc1ccc(CCNC(=O)c2ccc[n+](C)c2)cc1OC(=O)C(C)C>>CC(C)C(=O)Oc1ccc(CCNC(=O)C2=CN(C)C=CC2)cc1OC(=O)C(C)C | FC(C(=O)[O-])(F)F.C[N+]1=CC(=CC=C1)C(NCCC1=CC(=C(C=C1)OC(C(C)C)=O)OC(C(C)C)=O)=O.CO.C(=O)(O)[O-].[Na+].S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>CN1C=C(CC=C1)C(NCCC1=CC(=C(C=C1)OC(C(C)C)=O)OC(C(C)C)=O)=O | [CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][C:14](=[O:15])[c:16]2[cH:17][n+:18]([CH3:19])[cH:20][cH:21][cH:22]2)[cH:23][c:24]1[O:25][C:26](=[O:27])[CH:28]([CH3:29])[CH3:30]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][C:14](=[O:15... | CC(C)C(=O)Oc1ccc(CCNC(=O)c2ccc[n+](C)c2)cc1OC(=O)C(C)C | CC(C)C(=O)Oc1ccc(CCNC(=O)C2=CN(C)C=CC2)cc1OC(=O)C(C)C | null | null | CCOCC.O.C(C)OCC | Oxidation | OtherReaction | 13b45e156ec657ad0fdecedbaf109895984e5f87d1e6f37af8de99edd6e00b4c | fbae5f1853aa5e17e27560a7033259ef0622ff1b0fa96fba8ff14ddff833ee88 | O=C(NCCc1ccccc1)C1=CNC=CC1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[n+;H0;D3:7](-[C;D1;H3:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5]1=[CH;D2;+0:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[CH2;D2;+0:11]-1 | null | [] | null | null | 30 | MINUTE | A solution of 0.55 g (1 mmol) of 1-methyl-3-{N-[[β-[3,4-bis(isobutyryloxy)phenyl]ethyl]]}carbamoylpyridinium trifluoroacetate in 50 ml of deaerated water containing 10 ml of methanol was extracted three times with 30 ml portions of ether. To the resultant aqueous solution were added NaHCO3 (0.25 g, 3 mmol) and 50 ml of... | 10.6084/m9.figshare.5104873.v1 | null | null | Enamine.Enamine | C1=CC=[NH+]C=C1 | C1=C[NH]C=CC1 | c1ccccc1.C1=C[NH]C=CC1 | null | CCOCC.O.C(C)OCC | null | 0.5 | CC(C)C(=O)Oc1ccc(CCNC(=O)c2ccc[n+](C)c2)cc1OC(=O)C(C)C>CCOCC.O.C(C)OCC>CC(C)C(=O)Oc1ccc(CCNC(=O)C2=CN(C)C=CC2)cc1OC(=O)C(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c4b9f4b95d474b5a9a51663bf3ff7ff1 | O=C(O)c1cccnc1.O=C1CCC(=O)N1O>>O=C(ON1C(=O)CCC1=O)c1cccnc1 | CCOCC.C(C1=CN=CC=C1)(=O)O.ON1C(CCC1=O)=O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C1=CN=CC=C1)(=O)ON1C(CCC1=O)=O | O[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1.[OH:3][N:4]1[C:5](=[O:6])[CH2:7][CH2:8][C:9]1=[O:10]>>[O:1]=[C:2]([O:3][N:4]1[C:5](=[O:6])[CH2:7][CH2:8][C:9]1=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1 | O=C(O)c1cccnc1.O=C1CCC(=O)N1O | O=C(ON1C(=O)CCC1=O)c1cccnc1 | null | null | O1CCOCC1 | Protection | OtherReaction | a1b3ee4184fc00a0730e4c14eca3a5fbe87fccb44744074c13ef1bfbfabde8ad | e66168e1cfeb6611d93ee4c49193aae81e56c700a9fe46743dc42eed291ed0f9 | O=C(ON1C(=O)CCC1=O)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[O;D1;H0:8]=[C:9]1-[C:10]-[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]-1-[OH;D1;+0:15]>>[O;D1;H0:8]=[C:9]1-[C:10]-[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]-1-[O;H0;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 72 | [{"value": 72.0, "product": "C(C1=CN=CC=C1)(=O)ON1C(CCC1=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Nicotinic acid (4.025 g, 0.0327 mol) and N-hydroxysuccinimide (3.763 g, 0.0327 mol) were dissolved in 130 ml of dioxane. Dicyclohexylcarbodiimide (6.75 g, 0.032 mol) in 20 ml of dioxane was added. The reaction mixture was then stirred at room temperature for 3 hours. The dicyclohexylurea which precipitated was removed ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1CC[NH]C1.c1ccncc1 | HO- | O1CCOCC1 | null | 3 | O=C(O)c1cccnc1.O=C1CCC(=O)N1O>O1CCOCC1>O=C(ON1C(=O)CCC1=O)c1cccnc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2f8180b087294f358a57f119070003e4 | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.COC(=O)/C=C(/C)N>>COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1.N\C(=C/C(=O)OC)\C.C(C)O>>CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C | O=[C:9]([CH2:10][C:12](=[O:13])[O:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([NH:22][C:23]([CH3:24])=[O:25])[cH:26][cH:27]1)[CH:11]=[CH:28][c:29]1[cH:30][cH:31][cH:32][c:33]([N+:34](=[O:35])[O-:36])[cH:37]1.[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[C:6](/[CH3:7])[NH2:8]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])... | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.COC(=O)/C=C(/C)N | COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OCCOc1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C;D1;H3:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[NH;D2;+0:19]... | 68 | [{"value": 68.0, "product": "CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | 7 | CELSIUS | null | null | 15 g (0.04 moles) of 2-(4-acetylaminophenoxy)-ethyl 2-(3-nitrobenzilidene)acetylacetate and 4.19 g (0.04 moles) of methyl 3-aminocrotonate are heated for 4 hours under reflux in 40 ml of ethanol. The solution is cooled to 7° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | null | 7 | null | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.COC(=O)/C=C(/C)N>>COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4fb81d80d0c54438990463b5586fc380 | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CSCCOC(=O)/C=C(/C)N>>CSCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1.N\C(=C/C(=O)OCCSC)\C.C(C)O>>CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSC)C | O=[C:12]([CH2:13][C:15](=[O:16])[O:17][CH2:18][CH2:19][O:20][c:21]1[cH:22][cH:23][c:24]([NH:25][C:26]([CH3:27])=[O:28])[cH:29][cH:30]1)[CH:14]=[CH:31][c:32]1[cH:33][cH:34][cH:35][c:36]([N+:37](=[O:38])[O-:39])[cH:40]1.[CH3:1][S:2][CH2:3][CH2:4][O:5][C:6](=[O:7])/[CH:8]=[C:9](/[CH3:10])[NH2:11]>>[CH3:1][S:2][CH2:3][CH2:... | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CSCCOC(=O)/C=C(/C)N | CSCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OCCOc1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[NH;D2;+0:19]-[C:17... | 80 | [{"value": 80.0, "product": "CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSC)C", "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | 15 g (0.04 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 6.37 g (0.04 moles) of 2-methylthioethyl 3-aminocrotonate are heated under reflux in 30 ml of ethanol during 8 hours. The solution is then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-methylthioethox... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | null | -5 | null | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CSCCOC(=O)/C=C(/C)N>>CSCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dc1538eb82734bd38e7cfa4b9f6cdea5 | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CCOC(=O)/C=C(/C)N>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | C(C)O.[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1.N\C(=C/C(=O)OCC)\C>>CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C | O=[C:10]([CH2:11][C:13](=[O:14])[O:15][CH2:16][CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]([NH:23][C:24]([CH3:25])=[O:26])[cH:27][cH:28]1)[CH:12]=[CH:29][c:30]1[cH:31][cH:32][cH:33][c:34]([N+:35](=[O:36])[O-:37])[cH:38]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[C:7](/[CH3:8])[NH2:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1... | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CCOC(=O)/C=C(/C)N | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OCCOc1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[NH;D2;+0:19]-[C:17... | 75 | [{"value": 75.0, "product": "CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | 12.28 g (0.03 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 3.85 (0.03 moles) of ethyl 3-aminocrotonate are heated under reflux in 30 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | null | -5 | null | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CCOC(=O)/C=C(/C)N>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0762afb0cbd843a58951b15e1705bb6e | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CCSCCOC(=O)/C=C(/C)N>>CCSCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1.N\C(=C/C(=O)OCCSCC)\C.C(C)O>>CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSCC)C | O=[C:13]([CH2:14][C:16](=[O:17])[O:18][CH2:19][CH2:20][O:21][c:22]1[cH:23][cH:24][c:25]([NH:26][C:27]([CH3:28])=[O:29])[cH:30][cH:31]1)[CH:15]=[CH:32][c:33]1[cH:34][cH:35][cH:36][c:37]([N+:38](=[O:39])[O-:40])[cH:41]1.[CH3:1][CH2:2][S:3][CH2:4][CH2:5][O:6][C:7](=[O:8])/[CH:9]=[C:10](/[CH3:11])[NH2:12]>>[CH3:1][CH2:2][S... | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CCSCCOC(=O)/C=C(/C)N | CCSCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OCCOc1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[NH;D2;+0:19]-[C:17... | 60 | [{"value": 60.0, "product": "CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSCC)C", "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | 15 g (0.04 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 6.88 g (0.04 moles) of 2-ethylthioethyl 3-aminocrotonate were heated under reflux in 35 ml of ethanol for 8 hours. The solution was then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-ethylthioethoxyca... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | null | -5 | null | CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.CCSCCOC(=O)/C=C(/C)N>>CCSCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d3063e5ebfc341bb90d8962965943e78 | C/C(N)=C/C(=O)OCCSC(C)C.CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1>>CC(=O)Nc1ccc(OCCOC(=O)C2=C(C)NC(C)=C(C(=O)OCCSC(C)C)C2c2cccc([N+](=O)[O-])c2)cc1 | [N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1.N\C(=C/C(=O)OCCSC(C)C)\C.C(C)O>>CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSC(C)C)C | [NH2:18]/[C:19]([CH3:20])=[CH:21]\[C:22](=[O:23])[O:24][CH2:25][CH2:26][S:27][CH:28]([CH3:29])[CH3:30].O=[C:16]([CH2:15][C:13]([O:12][CH2:11][CH2:10][O:9][c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:42][cH:41]1)=[O:14])[CH:17]=[CH:31][c:32]1[cH:33][cH:34][cH:35][c:36]([N+:37](=[O:38])[O-:39])[cH:40]1>>[CH3:1]... | C/C(N)=C/C(=O)OCCSC(C)C.CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1 | CC(=O)Nc1ccc(OCCOC(=O)C2=C(C)NC(C)=C(C(=O)OCCSC(C)C)C2c2cccc([N+](=O)[O-])c2)cc1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OCCOc1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:2]1=[C;H0;D3;+0:1](-[CH3;D1;+0:7])-[NH;D2;+0:19]-[C:17](-[C;D1;H3:18])=[... | 42 | [{"value": 42.0, "product": "CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | 12 g (0l03 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenylidene)acetylacetate and 5.92 g (0.03 moles) of 2-isopropylthioethyl 3-aminocrotonate are heated under reflux in 30 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-isopropylthioeth... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | c1ccccc1.C1=CNC=CC1.c1ccccc1 | HO- | null | -5 | null | C/C(N)=C/C(=O)OCCSC(C)C.CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1>>CC(=O)Nc1ccc(OCCOC(=O)C2=C(C)NC(C)=C(C(=O)OCCSC(C)C)C2c2cccc([N+](=O)[O-])c2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b5c35d1e26be4d9da180372b4123f748 | COC(=O)/C=C(/C)N.O=C(C=Cc1cccc([N+](=O)[O-])c1)CC(=O)OCCNC(=O)c1cccnc1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OCCNC(=O)c2cccnc2)C1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCNC(C2=CN=CC=C2)=O)C=CC1.N\C(=C/C(=O)OC)\C.C(C)O>>CC=1NC(=C(C(C1C(=O)OCCNC(C1=CN=CC=C1)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C | [CH3:1][O:2][C:3](=[O:4])/[CH:5]=[C:6](/[CH3:7])[NH2:8].O=[C:9]([CH:10]=[CH:26][c:27]1[cH:28][cH:29][cH:30][c:31]([N+:32](=[O:33])[O-:34])[cH:35]1)[CH2:11][C:12](=[O:13])[O:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([CH3... | COC(=O)/C=C(/C)N.O=C(C=Cc1cccc([N+](=O)[O-])c1)CC(=O)OCCNC(=O)c1cccnc1 | COC(=O)C1=C(C)NC(C)=C(C(=O)OCCNC(=O)c2cccnc2)C1c1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OCCNC(=O)c1cccnc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C;D1;H3:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:2]1=[C;H0;D3;+0:1](-[CH3;D1;+0:7])-[NH;D2;+0:19]-[C:17](-[C;D1;H3:... | 70 | [{"value": 70.0, "product": "CC=1NC(=C(C(C1C(=O)OCCNC(C1=CN=CC=C1)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 25 g (0.07 moles) of 2-(N-nicotinoylamino)ethyl 2-(3-nitrobenzylidene)acetylacetate and 7.51 g (0.07 moles) of methyl 3-aminocrotonate are heated uner reflux in 70 ml of ethanol for 45 minute. The solution is the cooled to room temperature to obtain 2-(N-nicotinoylamino)ethyl 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitroph... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccncc1.c1ccccc1 | HO- | null | null | null | COC(=O)/C=C(/C)N.O=C(C=Cc1cccc([N+](=O)[O-])c1)CC(=O)OCCNC(=O)c1cccnc1>>COC(=O)C1=C(C)NC(C)=C(C(=O)OCCNC(=O)c2cccnc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9f0b0ca41b4b431daa1c7c12af0a959b | CC1CC(OC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)CC(C)(C)C1.CCOC(=O)/C=C(/C)N>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC2CC(C)CC(C)(C)C2)C1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OC2CC(CC(C2)C)(C)C)C=CC1.N\C(=C/C(=O)OCC)\C.C(C)O>>CC=1NC(=C(C(C1C(=O)OC1CC(CC(C1)C)(C)C)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C | O=[C:10]([CH2:11][C:13](=[O:14])[O:15][CH:16]1[CH2:17][CH:18]([CH3:19])[CH2:20][C:21]([CH3:22])([CH3:23])[CH2:24]1)[CH:12]=[CH:25][c:26]1[cH:27][cH:28][cH:29][c:30]([N+:31](=[O:32])[O-:33])[cH:34]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[C:7](/[CH3:8])[NH2:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9... | CC1CC(OC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)CC(C)(C)C1.CCOC(=O)/C=C(/C)N | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC2CC(C)CC(C)(C)C2)C1c1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OC1CCCCC1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[NH;D2;+0:19]-[C:17... | 37 | [{"value": 37.0, "product": "CC=1NC(=C(C(C1C(=O)OC1CC(CC(C1)C)(C)C)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | 21.87 g (0.06 moles) of 3,3,5-trimethylcyclohexyl 2-(3-nitrobenzylidene)acetylacetate and 7.84 g (0.06 moles) of ethyl 3-aminocrotonate are heated under reflux in 60 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 3,3,5-trimethylcyclohexyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-d... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.C1CCCCC1.c1ccccc1 | HO- | null | -5 | null | CC1CC(OC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)CC(C)(C)C1.CCOC(=O)/C=C(/C)N>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC2CC(C)CC(C)(C)C2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e8342923f9524540becdf8521b43cb93 | CC(=O)CC(=O)OCCOC(=O)c1ccc(NC(C)=O)cc1.CCOC(=O)/C=C(/C)N.O=Cc1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)c2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | C(C)(=O)CC(=O)OCCOC(C1=CC=C(C=C1)NC(C)=O)=O.N\C(=C/C(=O)OCC)\C.[N+](=O)([O-])C=1C=C(C=O)C=CC1>>CC=1NC(=C(C(C1C(=O)OCCOC(C1=CC=C(C=C1)NC(C)=O)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C | O=[C:10]([CH3:11])[CH2:12][C:13](=[O:14])[O:15][CH2:16][CH2:17][O:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([NH:25][C:26]([CH3:27])=[O:28])[cH:29][cH:30]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[C:7](/[CH3:8])[NH2:9].O=[CH:31][c:32]1[cH:33][cH:34][cH:35][c:36]([N+:37](=[O:38])[O-:39])[cH:40]1>>[CH3:1][CH2:2][O:3][... | CC(=O)CC(=O)OCCOC(=O)c1ccc(NC(C)=O)cc1.CCOC(=O)/C=C(/C)N.O=Cc1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)c2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2d6eb759789122e9ec83b9861eb8e597e0c5780f40f69f3aae7699c0785b5370 | 28ba2ddb7f06716163ed355d9b83bce1774d980934be29e1b006e200b14a1fb4 | O=C(OCCOC(=O)c1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:19]-[C:17](-[C;D1;H3:18])=[C... | 46 | [{"value": 46.0, "product": "CC=1NC(=C(C(C1C(=O)OCCOC(C1=CC=C(C=C1)NC(C)=O)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | 20 g (0.07 moles) of 2-(4-acetylaminobenzoyloxy)ethyl acetylacetate, 8.41 (0.07 moles) of ethyl 3-aminocrotonate and 9.84 g (0.07 moles) of 3-nitrobenzaldehyde are heated under reflux in 65 ml of ethanol for 8 hours. The solvent is then evaporated, 15 ml of boiling methanol are added to the residue, the solution is dis... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Ketone | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | C(C)O | -5 | null | CC(=O)CC(=O)OCCOC(=O)c1ccc(NC(C)=O)cc1.CCOC(=O)/C=C(/C)N.O=Cc1cccc([N+](=O)[O-])c1>C(C)O>CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)c2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7474294ae7e34856979084eb68096e62 | CC(=O)Nc1ccc(C(=O)OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.COC(=O)/C=C(/C)N>>COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)c2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC(C2=CC=C(C=C2)NC(C)=O)=O)C=CC1.N\C(=C/C(=O)OC)\C.C(C)O>>CC=1NC(=C(C(C1C(=O)OCCOC(C1=CC=C(C=C1)NC(C)=O)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C | O=[C:9]([CH2:10][C:12](=[O:13])[O:14][CH2:15][CH2:16][O:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([NH:24][C:25]([CH3:26])=[O:27])[cH:28][cH:29]1)[CH:11]=[CH:30][c:31]1[cH:32][cH:33][cH:34][c:35]([N+:36](=[O:37])[O-:38])[cH:39]1.[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[C:6](/[CH3:7])[NH2:8]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1... | CC(=O)Nc1ccc(C(=O)OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.COC(=O)/C=C(/C)N | COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)c2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | c879634b90165a0dcfef41d5a6052913cc640596ce2ad80d54a68cd5d3dce096 | c3a613f0d28158fdfd02e6d314d92803aecfd456b76db2bcbdc1d343fa1a52a5 | O=C(OCCOC(=O)c1ccccc1)C1=CNC=CC1c1ccccc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[C;D1;H3:12]-[#8:13]-[C:14](=[O;D1;H0:15])/[CH;D2;+0:16]=[C:17](/[C;D1;H3:18])-[NH2;D1;+0:19]>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[NH;D2;+0:19]... | 94 | [{"value": 94.0, "product": "CC=1NC(=C(C(C1C(=O)OCCOC(C1=CC=C(C=C1)NC(C)=O)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 20 g (0.05 moles) of 2-(4-acetylaminobenzoyloxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 5.23 g (0.05 moles) of methyl 3-aminocrotonate are heated under reflux in 45 ml of ethanol for 8 hours. The solution is then cooled to room temperature to obtain 2-(4-acetylaminobenzoyloxy)ethyl 2,6-dimethyl-5-methoxycarbonyl-... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester.Ester | Enamine.Enamine.Ester.Ester | null | C1=CNC=CC1 | C1=CNC=CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)Nc1ccc(C(=O)OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1.COC(=O)/C=C(/C)N>>COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)c2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e0ff61d3b6514a55bc0cf587e046c10f | CCOC(=O)C(CCC#N)C(=O)OCC.ClCc1cccc2ccccc12>>CCOC(=O)C(CCC#N)(Cc1cccc2ccccc12)C(=O)OCC | C(#N)CCC(C(=O)O)CC1=CC=CC2=CC=CC=C12.C(C)OC(C(C(=O)OCC)CCC#N)=O.[H-].[Na+].ClCC1=CC=CC2=CC=CC=C12>>C(C)OC(C(C(=O)OCC)(CC1=CC=CC2=CC=CC=C12)CCC#N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][C:9]#[N:10])[C:22](=[O:23])[O:24][CH2:25][CH3:26].Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH2:8][C:9]#[N:10])([CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH... | CCOC(=O)C(CCC#N)C(=O)OCC.ClCc1cccc2ccccc12 | CCOC(=O)C(CCC#N)(Cc1cccc2ccccc12)C(=O)OCC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]-[C:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[C:10]-[C:11])(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | null | [] | null | null | 2 | HOUR | 4-Cyano-2(R,S)-α-naphthylmethylbutyric acid: 2.13 g of 2-cyanoethylmalonic acid diethyl ester are added to a suspension of 0.48 g of sodium hydride dispersion in 25 ml of DMF. The reaction mixture is stirred for 2 hours at 80° and then, at room temperature, 1.77 g of α-chloromethylnaphthalene in 5 ml of DMF are added. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccc2ccccc2c1 | HCl | CN(C)C=O | null | 2 | CCOC(=O)C(CCC#N)C(=O)OCC.ClCc1cccc2ccccc12>CN(C)C=O>CCOC(=O)C(CCC#N)(Cc1cccc2ccccc12)C(=O)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e9adca82e09c421dacd1f2f89a865ee9 | CCOC(=O)C(Cc1cccc2ccccc12)C(=O)OCC.N#CCC(Cc1cccc2ccccc12)C(=O)O>>CCOC(=O)C(CC#N)(Cc1cccc2ccccc12)C(=O)OCC | ClCC#N.[H-].[Na+].C(#N)CC(C(=O)O)CC1=CC=CC2=CC=CC=C12.C(C)OC(C(C(=O)OCC)CC1=CC=CC2=CC=CC=C12)=O>>C(C)OC(C(C(=O)OCC)(CC1=CC=CC2=CC=CC=C12)CC#N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12)[C:21](=[O:22])[O:23][CH2:24][CH3:25].O=C(O)C(Cc1cccc2ccccc12)[CH2:7][C:8]#[N:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][C:8]#[N:9])([CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:... | CCOC(=O)C(Cc1cccc2ccccc12)C(=O)OCC.N#CCC(Cc1cccc2ccccc12)C(=O)O | CCOC(=O)C(CC#N)(Cc1cccc2ccccc12)C(=O)OCC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | bfecf89b6b5ae48c89ff3eb9e6cdb87821b0f7c3253749adacd22eb53d8e3071 | fd1c29f62a00313cae68327e8c993a8897cd9eb1e866631a61b0778362ef8fa0 | c1ccc2ccccc2c1 | O-C(=O)-C(-C-c1:c:c:c:c2:c:c:c:c:c:1:2)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C:9]-[c:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:8](-[C:9]-[c:10])(-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | null | [] | null | null | 1 | HOUR | 2(R,S)-Cyanomethyl-3-α-naphthylpropionic acid: 3.0 g of α-naphthylmethylmalonic acid diethyl ester and, after 30 minutes, 0.6 ml of chloroacetonitrile are added to a stirred suspension of 0.44 g of sodium hydride dispersion in 50 ml of DMF. The reaction mixture is stirred for 1 hour at 50° and then concentrated by evap... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ester | Ester.Ester | c1ccc2ccccc2c1 | null | c1ccc2ccccc2c1 | HO- | CN(C)C=O | null | 1 | CCOC(=O)C(Cc1cccc2ccccc12)C(=O)OCC.N#CCC(Cc1cccc2ccccc12)C(=O)O>CN(C)C=O>CCOC(=O)C(CC#N)(Cc1cccc2ccccc12)C(=O)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-efc6ced26c664eaca2e01d57ea29f564 | O=C(Cl)C(=O)Cl.c1ccc2ccnc-2cc1>>O=Cc1cccc2nccc-2c1 | C(C)(=O)[O-].[Na+].N1=C2C(C=C1)=CC=CC=C2.C(C(=O)Cl)(=O)Cl.N>>N1=C2C(C=C1)=CC(=CC=C2)C=O | O=C(Cl)[C:2](Cl)=[O:1].[cH:3]1[cH:4][cH:5][cH:6][c:7]2[n:8][cH:9][cH:10][c:11]-2[cH:12]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[n:8][cH:9][cH:10][c:11]-2[cH:12]1 | O=C(Cl)C(=O)Cl.c1ccc2ccnc-2cc1 | O=Cc1cccc2nccc-2c1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 3ced9810526be113fa68bdf0ef400500bae1bcbd61adf0158fddbde34e9934dd | 0a55294ee33cff9347c17b969808c7366384c74b5b060fa0a49da4a017a23ca5 | c1ccc2ccnc-2cc1 | Cl-C(=O)-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:5](:[c:4]:[c:3]):[c:6]:[c:7] | null | [] | null | null | 30 | MINUTE | Cyclohepta[b]pyrrole-5-carboxylic acid nitrile: 800 mg of cyclohepta[b]pyrrole (manufactured according to Helv. Chim. Acta 67, 1647 (1984)) are added in portions, at 0°, to a solution of 1.1 ml of oxalyl chloride in 40 ml of DMF. The whole is subsequently stirred for 30 minutes at room temperature, then 60 ml of satura... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide | Aldehyde | c1ccc2ccnc2cc1 | c1ccc2ccnc2cc1 | c1ccc2ccnc2cc1 | Other | CN(C)C=O | null | 0.5 | O=C(Cl)C(=O)Cl.c1ccc2ccnc-2cc1>CN(C)C=O>O=Cc1cccc2nccc-2c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0c2d879632c7416297f9a04382172ffc | CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC.N#CCCC(Oc1cccc2ccccc12)C(=O)O>>CCOC(=O)C(CCC#N)(Oc1cccc2ccccc12)C(=O)OCC | C(#N)CCC(C(=O)O)OC1=CC=CC2=CC=CC=C12.[OH-].[K+].C(C)OC(C(C(=O)OCC)OC1=CC=CC2=CC=CC=C12)=O.C(C=C)#N>>C(C)OC(C(C(=O)OCC)(OC1=CC=CC2=CC=CC=C12)CCC#N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([O:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12)[C:22](=[O:23])[O:24][CH2:25][CH3:26].O=C(O)C(Oc1cccc2ccccc12)[CH2:7][CH2:8][C:9]#[N:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH2:8][C:9]#[N:10])([O:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17... | CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC.N#CCCC(Oc1cccc2ccccc12)C(=O)O | CCOC(=O)C(CCC#N)(Oc1cccc2ccccc12)C(=O)OCC | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | df64c5d53fe4018b334ff627ce4f1f325b7ebcc08a0f6a5be58eabe40875518a | 3a3301898dd0537768086f3ea14ed0e0cb2dc030f3256deb7707d8e800f76526 | c1ccc2ccccc2c1 | O-C(=O)-C(-O-c1:c:c:c:c2:c:c:c:c:c:1:2)-[CH2;D2;+0:1]-[C:2]-[C:3]#[N;D1;H0:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[#8:10]-[c:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[#8:10]-[c:11])(-[CH2;D2;+0:1]-[C:2]-[C:3]#[N;D1;H0:4])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | null | [] | null | null | 5 | DAY | 4-Cyano-2(R,S)-α-naphthoxybutyric acid: 0.11 ml of a 50% aqueous KOH solution is added at 0°, while stirring, to a mixture of 5.0 g of α-naphthoxymalonic acid diethyl ester and 1.09 ml of acrylonitrile. The reaction mixture is stirred for 5 days at room temperature and then dissolved in ethyl acetate. The ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ester.Ether.Ether | Ester.Ester.Ether | c1ccc2ccccc2c1 | null | c1ccc2ccccc2c1 | HO- | C(C)(=O)OCC | null | 120 | CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC.N#CCCC(Oc1cccc2ccccc12)C(=O)O>C(C)(=O)OCC>CCOC(=O)C(CCC#N)(Oc1cccc2ccccc12)C(=O)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9f8a984e88484318932c00f0f1933f40 | CCOC(=O)C(Br)C(=O)OCC.Oc1cccc2ccccc12>>CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC | C1(=CC=CC2=CC=CC=C12)O.[H-].[Na+].C(C)OC(C(C(=O)OCC)Br)=O>>C(C)OC(C(C(=O)OCC)OC1=CC=CC2=CC=CC=C12)=O | Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=[O:19])[O:20][CH2:21][CH3:22].[OH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([O:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12)[C:18](=[O:19])[O:20][CH2:21][CH3:22] | CCOC(=O)C(Br)C(=O)OCC.Oc1cccc2ccccc12 | CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 1abe5687f21dfe01b11318540a21f9edb38806e03f96e75bf8c2106db3fe9462 | 51ddfc8e04785767c04eb49244add5bfc6d44a3e44b55034aace28217a5407e3 | c1ccc2ccccc2c1 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9] | null | [] | null | null | 30 | MINUTE | A solution of 25 g of 1-naphthol in 50 ml of DMF is slowly added dropwise to a solution of 7.6 g of sodium hydride dispersion in 300 ml of DMF. The suspension is stirred for 30 minutes and subsequently 41.5 g of bromomalonic acid diethyl ester in 50 ml of DMF are added dropwise. The reaction mixture is further stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Aromatic alcohol | Ester.Ester.Ether | null | null | c1ccc2ccccc2c1 | HBr | CN(C)C=O | null | 0.5 | CCOC(=O)C(Br)C(=O)OCC.Oc1cccc2ccccc12>CN(C)C=O>CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-822d95ff4f2445239bc38f50ab6bd0a8 | CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC.NC(=O)CCC(Oc1cccc2ccccc12)C(=O)O>>CCOC(=O)C(CCC(N)=O)(Oc1cccc2ccccc12)C(=O)OCC | C(N)(=O)CCC(C(=O)O)OC1=CC=CC2=CC=CC=C12.N12CCCCCC2=NCCC1.C(C)OC(C(C(=O)OCC)OC1=CC=CC2=CC=CC=C12)=O.C(C=C)(=O)N.Cl>>C(C)OC(C(C(=O)OCC)(OC1=CC=CC2=CC=CC=C12)CCC(N)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([O:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12)[C:23](=[O:24])[O:25][CH2:26][CH3:27].O=C(O)C(Oc1cccc2ccccc12)[CH2:7][CH2:8][C:9]([NH2:10])=[O:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH2:8][C:9]([NH2:10])=[O:11])([O:12][c:13]1[cH:14][cH:15]... | CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC.NC(=O)CCC(Oc1cccc2ccccc12)C(=O)O | CCOC(=O)C(CCC(N)=O)(Oc1cccc2ccccc12)C(=O)OCC | null | null | C(C)#N.O | C-C Coupling | OtherReaction | df64c5d53fe4018b334ff627ce4f1f325b7ebcc08a0f6a5be58eabe40875518a | 3a3301898dd0537768086f3ea14ed0e0cb2dc030f3256deb7707d8e800f76526 | c1ccc2ccccc2c1 | O-C(=O)-C(-O-c1:c:c:c:c2:c:c:c:c:c:1:2)-[CH2;D2;+0:1]-[C:2]-[C:3](-[N;D1;H2:4])=[O;D1;H0:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[#8:11]-[c:12])-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D4;+0:10](-[#8:11]-[c:12])(-[CH2;D2;+0:1]-[C:2]-[C:3](-[N;D1;H2:4])=[O;D1;H0:5])-[C:13]... | null | [] | null | null | 24 | HOUR | 4-Carbamoyl-2(R,S)-α-naphthoxybutyric acid: 1.49 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene are added to a solution of 3 g of α-naphthoxymalonic acid diethyl ester (Example 36a) and 0.71 g of acrylamide in 5 ml of acetonitrile and the whole is stirred at room temperature for 24 hours. 25 ml of water are added to the reac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ester.Ether.Ether | Ester.Ester.Ether | c1ccc2ccccc2c1 | null | c1ccc2ccccc2c1 | HO- | C(C)#N.O | null | 24 | CCOC(=O)C(Oc1cccc2ccccc12)C(=O)OCC.NC(=O)CCC(Oc1cccc2ccccc12)C(=O)O>C(C)#N.O>CCOC(=O)C(CCC(N)=O)(Oc1cccc2ccccc12)C(=O)OCC |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-29c1287a74224764a2342d6da5b34f12 | Cl>>Cl | C(C)(C)OC(C)C.Cl.COC1=CC=C(C=C1)C1=NN=C(N1C1=CC=C(C=C1)OC)CC>>Cl.COC1=CC=C(C=C1)C1=NN=C(N1C1=CC=C(C=C1)OC)CC | [ClH:24]>>[ClH:24] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 2.9 ml of a solution of 5.9N hydrogen chloride in ethanol were aded to a solution of 5 g of the product of Example 1 in 5 ml of ethanol and the mixture was stirred while adding isopropyl ether thereto. The mixture was stirred for 24 hours and was filtered. The product was empasted with isopropyl ether, filtered and dri... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-973abaec5c9e43889008b8fe153c5b7e | Cl>>Cl | Cl.C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC.C(C)(C)OC(C)C>>Cl.C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC | [ClH:22]>>[ClH:22] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 2.85 ml of a 6.4N hydrogen chloride solution in ethanol were added to a solution of 5.1 g of the product of Example 6 in 5.1 ml of ethanol and then isopropyl ether was added thereto. The mixture was filtered and the recovered product was empasted several times with isopropyl ether, filtered and was dried. The product w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-afd7c470aaa9450c98ccacd72a59e875 | COc1ccc(C(=O)NNC(C)=O)cc1.Nc1ccccc1>>COc1ccc(-c2nnc(C)n2-c2ccccc2)cc1 | NC1=CC=CC=C1.[P].COC1=CC=C(C(=O)NNC(C)=O)C=C1>>COC1=CC=C(C=C1)C1=NN=C(N1C1=CC=CC=C1)C | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]1)[NH:8][NH:9][C:10](=O)[CH3:11].[NH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9][c:10]([CH3:11])[n:12]2-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | COc1ccc(C(=O)NNC(C)=O)cc1.Nc1ccccc1 | COc1ccc(-c2nnc(C)n2-c2ccccc2)cc1 | null | null | ClC1=C(C=CC=C1)Cl | Aromatic Heterocycle Formation | OtherReaction | dd6aff0a7fa936aa4206620fc45281159b3db63e711bd694b764463daf82cbcc | 1f5c57f9ffab8a5214b697412c1715772187bdfe92c542c30f8b933239b9a67f | c1ccc(-c2nncn2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[NH2;D1;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[n;H0;D3;+0:11]:1-[c;H0... | null | [] | null | null | null | null | Using the procedure of Step B in Example 1, 26.3 ml of aniline, 150 ml of o-dichlorobenzene, 4.65 ml of phosphorus trichlorode and 10 g of N-(4-methoxybenzoyl)-N'-acetyl-hydrazine [prepared by process of J. Org., Vol. 19 (1954), p. 194-201] were reacted to obtain 7.1 g of 3-(4-methoxyphenyl)-4-phenyl-5-methyl -4H-1,2,4... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Primary amine | null | null | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1.c1ccccc1 | HO- | ClC1=C(C=CC=C1)Cl | null | null | COc1ccc(C(=O)NNC(C)=O)cc1.Nc1ccccc1>ClC1=C(C=CC=C1)Cl>COc1ccc(-c2nnc(C)n2-c2ccccc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-43e6192a1fee4a98970c082a16dc1ae7 | COc1ccc(C(=S)Nc2ccc([N+](=O)[O-])cc2)cc1.NN>>COc1ccc(C(=NN)Nc2ccc([N+](=O)[O-])cc2)cc1 | COC1=CC=C(C(=S)NC2=CC=C(C=C2)[N+](=O)[O-])C=C1.O.NN>>COC1=CC=C(C=C1)C(NC1=CC=C(C=C1)[N+](=O)[O-])=NN | S=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]1)[NH:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1.[NH2:8][NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[N:8][NH2:9])[NH:10][c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | COc1ccc(C(=S)Nc2ccc([N+](=O)[O-])cc2)cc1.NN | COc1ccc(C(=NN)Nc2ccc([N+](=O)[O-])cc2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3c53372bbc90f475970c579b2f74cfce0dce40a85514dfc798820726b601021c | 9e62eb731012f88793268a138e2b75455c107ccea6781f13073353f313d518c0 | N=C(Nc1ccccc1)c1ccccc1 | S=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[c:4](:[c:5]):[c:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[N;D1;H2:7]-[N;H0;D2;+0:8]=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A mixture of 10 g of 4-methoxy-4'-nitrothiobenzanilide [prepared by process of Ann. Chem., Vol. 716 (1968), p. 209-211], 100 ml of ethanol and 15 ml of hydrazine hydrate was heated to reflux and then was allowed to return to room temperature and was filtered. The product was washed with ethanol and dried at 80° C. unde... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Thioamide | Hydrazone | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | null | null | COc1ccc(C(=S)Nc2ccc([N+](=O)[O-])cc2)cc1.NN>C(C)O>COc1ccc(C(=NN)Nc2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-118d97fa6ea14796a1c2c555fbaee88f | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc([N+](=O)[O-])cc1>>CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc(N)cc1 | C(C)C1=NN=C(N1C1=CC=C(C=C1)[N+](=O)[O-])C1=CC=C(C=C1)OC>>C(C)C1=NN=C(N1C1=CC=C(C=C1)N)C1=CC=C(C=C1)OC | O=[N+:20]([O-])[c:19]1[cH:18][cH:17][c:16](-[n:15]2[c:3]([CH2:2][CH3:1])[n:4][n:5][c:6]2-[c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]2)[cH:22][cH:21]1>>[CH3:1][CH2:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]2)[n:15]1-[c:16]1[cH:17][cH:18][c:19]([NH2:20])[cH:21][cH:22]1 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc([N+](=O)[O-])cc1 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc(N)cc1 | null | null | Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2nncn2-c2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 41.9 | [{"value": 41.9, "product": "C(C)C1=NN=C(N1C1=CC=C(C=C1)N)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 23 g of stannous chloride in 20 ml of concentrated hydrochloric acid was added all at once to a solution of 10 g of 3-ethyl-5-(4-methoxyphenyl)-4-(4-nitrophenyl)-4H-1,2,4-triazole in 50 ml of concentrated hydrochloric acid and the mixture was vigorously stirred for 2 hours and was filtered. The recovered ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1nc[nH]n1.c1ccccc1.c1ccccc1 | Other | Cl | null | 2 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc([N+](=O)[O-])cc1>Cl>CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc(N)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1fd7cbb8125345dca119b87a84a21449 | CCOC(=O)Cc1nnc(-c2ccc(OC)cc2)n1-c1ccccc1>>COc1ccc(-c2nnc(CC(=O)O)n2-c2ccccc2)cc1 | C(C)OC(CC1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC)=O.[OH-].[Na+]>>COC1=CC=C(C=C1)C=1N(C(=NN1)CC(=O)O)C1=CC=CC=C1 | CC[O:14][C:12]([CH2:11][c:10]1[n:9][n:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23][cH:22]2)[n:15]1-[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9][c:10]([CH2:11][C:12](=[O:13])[OH:14])[n:15]2-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23]1 | CCOC(=O)Cc1nnc(-c2ccc(OC)cc2)n1-c1ccccc1 | COc1ccc(-c2nnc(CC(=O)O)n2-c2ccccc2)cc1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nncn2-c2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 98.2 | [{"value": 98.2, "product": "COC1=CC=C(C=C1)C=1N(C(=NN1)CC(=O)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | A mixture of 4 g of the product of Example 16, 10 ml of 2N sodium hydroxide and 20 ml of ethanol was stirred at 60° C. under argon for 30 minutes and the ethanol was evaporated at 40° C. under reduced pressure. 9.9 ml of 2N hydrochloric acid were added to the aqueous solution and the mixture stood at 0° to 5° C. for 16... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1nc[nH]n1.c1ccccc1 | Other | C(C)O | 60 | 0.5 | CCOC(=O)Cc1nnc(-c2ccc(OC)cc2)n1-c1ccccc1>C(C)O>COc1ccc(-c2nnc(CC(=O)O)n2-c2ccccc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-05f2c0b8eede4b9b9b7b2b83900de675 | CN(C)c1ccc(C(=S)Nc2ccc([N+](=O)[O-])cc2)cc1.NN>>CN(C)c1ccc(C(N)=NNc2ccc([N+](=O)[O-])cc2)cc1 | O.CN(C1=CC=C(C=C1)C(NC1=CC=C(C=C1)[N+](=O)[O-])=S)C.C(C)O.O.NN>>CN(C1=CC=C(C=C1)C(N)=NNC1=CC=C(C=C1)[N+](=O)[O-])C | S=[C:8]([c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:22][cH:21]1)[NH:9][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1.[NH2:10][NH2:11]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([NH2:9])=[N:10][NH:11][c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | CN(C)c1ccc(C(=S)Nc2ccc([N+](=O)[O-])cc2)cc1.NN | CN(C)c1ccc(C(N)=NNc2ccc([N+](=O)[O-])cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 29cc17f84ec422e05e61f206c2fddfda6fcda0429494b214b3d88388d237b446 | 2c9cabc0e41405e0887785b0566b4a207f13df543da8063931b5dc5fb169db73 | C(=NNc1ccccc1)c1ccccc1 | S=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[NH2;D1;+0:12]>>[NH2;D1;+0:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:11]-[NH;D2;+0:12]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c:8](:[c:9]):[c:10] | null | [] | 10 | CELSIUS | null | null | A suspension of 30 g of the product of Step A and 180 ml of ethanol was heated to reflux and 30 ml of hydrazine hydrate were added thereto. The mixture was refluxed for 15 minutes and then 180 ml of distilled water were added thereto. The mixture was cooled to 10° C. and was vacuum filtered. The product was washed with... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Thioamide | Hydrazone.Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | 10 | null | CN(C)c1ccc(C(=S)Nc2ccc([N+](=O)[O-])cc2)cc1.NN>>CN(C)c1ccc(C(N)=NNc2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4d9a7267f4f74c9f8411fea686761629 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc(OC)cc1>>CCc1nnc(-c2ccc(O)cc2)n1-c1ccc(O)cc1 | COC1=CC=C(C=C1)C1=NN=C(N1C1=CC=C(C=C1)OC)CC.Br>>C(C)C1=NN=C(N1C1=CC=C(C=C1)O)C1=CC=C(C=C1)O | C[O:11][c:10]1[cH:9][cH:8][c:7](-[c:6]2[n:5][n:4][c:3]([CH2:2][CH3:1])[n:14]2-[c:15]2[cH:16][cH:17][c:18]([O:19]C)[cH:20][cH:21]2)[cH:13][cH:12]1>>[CH3:1][CH2:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]2)[n:14]1-[c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]1 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc(OC)cc1 | CCc1nnc(-c2ccc(O)cc2)n1-c1ccc(O)cc1 | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(-c2nncn2-c2ccccc2)cc1 | 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] | 80.6 | [{"value": 80.6, "product": "C(C)C1=NN=C(N1C1=CC=C(C=C1)O)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 6 g of 3,4-bis-(4-methoxyphenyl)-5-ethyl-4H-1,2,4-triazole and 25 ml of a solution of hydrobromic acid at 48% was refluxed with stirring for one hour and the hydrobromic acid was distilled under reduced pressure. The crystalline residue was dissolved in 30 ml of hot water and ammonium hydroxide was added ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1nc[nH]n1.c1ccccc1.c1ccccc1 | Other | null | null | 1 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccc(OC)cc1>>CCc1nnc(-c2ccc(O)cc2)n1-c1ccc(O)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5e1d0bd51fd34a7eb7ec41264e86a366 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccccc1>>CCc1nnc(-c2ccc(O)cc2)n1-c1ccccc1 | C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC>>C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)O | C[O:11][c:10]1[cH:9][cH:8][c:7](-[c:6]2[n:5][n:4][c:3]([CH2:2][CH3:1])[n:14]2-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:13][cH:12]1>>[CH3:1][CH2:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]2)[n:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccccc1 | CCc1nnc(-c2ccc(O)cc2)n1-c1ccccc1 | null | null | Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nncn2-c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 88.5 | [{"value": 88.5, "product": "C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 3.86 g of 3-ethyl-5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole and 20 ml of a hydrobromic acid solution at 48% was refluxed with stirring for one hour and the mixture was evaporated to dryness under reduced pressure. The residue was dissolved in 20 ml of hot water and ammonium hydroxide was added until ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1nc[nH]n1.c1ccccc1.c1ccccc1 | Other | Br | null | 1 | CCc1nnc(-c2ccc(OC)cc2)n1-c1ccccc1>Br>CCc1nnc(-c2ccc(O)cc2)n1-c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-02572d7994bc44c39cdf4b16503d331d | CN(C)c1ccc(C(=O)Cl)cc1.COc1ccc(N)cc1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>COc1ccc(NC(=S)c2ccc(N(C)C)cc2)cc1 | COC1=CC=C(C=C1)N.CN(C1=CC=C(C(=O)Cl)C=C1)C.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN(C1=CC=C(C=C1)C(NC1=CC=C(C=C1)OC)=S)C | O=[C:8](Cl)[c:10]1[cH:11][cH:12][c:13]([N:14]([CH3:15])[CH3:16])[cH:17][cH:18]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:19][cH:20]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:9])(S2)S3>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[S:9])[c:10]2[cH:11][cH:12][c:13]([N:14]([CH3:15])[CH3:16])[cH:17][cH:18]2)[cH:19][cH:20]1 | CN(C)c1ccc(C(=O)Cl)cc1.COc1ccc(N)cc1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | COc1ccc(NC(=S)c2ccc(N(C)C)cc2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | afaf3e800867af1ca2177e3f71caf1ba41eb7461b7eb53cfd739e1caf00d2671 | 6b0c38d2b30255f3d3dfd2267502d7ead0ac44907f3892e7c28e85687e5fddde | S=C(Nc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=O)-[c:2](:[c:3]):[c:4].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:5])(-S-2)-S-3.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[S;H0;D1;+0:5]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:2](:[c:3]):[c:4] | 63.5 | [{"value": 63.5, "product": "CN(C1=CC=C(C=C1)C(NC1=CC=C(C=C1)OC)=S)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 1 | HOUR | 13.6 g of p-anisidine were added to a solution of 22.2 g of 4-dimethylamino-benzoic acid chloride in 84 ml of anhydrous pyridine and the mixture was refluxed for one hour and cooled to 30° C. 33 g of phosphorus pentasulfide were added to the mixture which was refluxed for 2 hours and was then poured into an ice water-c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | S1P2SP3SP1SP(S2)S3 | null | c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | 30 | 1 | CN(C)c1ccc(C(=O)Cl)cc1.COc1ccc(N)cc1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>COc1ccc(NC(=S)c2ccc(N(C)C)cc2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1a0aab0702614837a64963489ec21c3d | CC(CN)COc1cccc(CN2CCCCC2)c1.NN.O=C(Oc1ccccc1)Oc1ccccc1>>CC(CNC(=O)NN)COc1cccc(CN2CCCCC2)c1 | O.NN.CC(CN)COC1=CC(=CC=C1)CN1CCCCC1.C1(=CC=CC=C1)OC(OC1=CC=CC=C1)=O>>CC(CNC(=O)NN)COC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][CH:2]([CH2:3][NH2:4])[CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23]1.[NH2:7][NH2:8].c1ccc(O[C:5](Oc2ccccc2)=[O:6])cc1>>[CH3:1][CH:2]([CH2:3][NH:4][C:5](=[O:6])[NH:7][NH2:8])[CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][c:15]([CH2:16][N:17]2[CH2:18][C... | CC(CN)COc1cccc(CN2CCCCC2)c1.NN.O=C(Oc1ccccc1)Oc1ccccc1 | CC(CNC(=O)NN)COc1cccc(CN2CCCCC2)c1 | null | null | C(C)O | Acylation | OtherReaction | a6296f6616de2a322029f7e745d352cd6c62af427a692d16dc3213fd042fb8c8 | ce54bbe05498a8c778a96743eed0f6d1f7ad384b001367fec90aabc78ce1a6a5 | c1ccc(CN2CCCCC2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[N;D1;H2:4]-[NH2;D1;+0:5].[O;D1;H0:6]=[C;H0;D3;+0:7](-O-c1:c:c:c:c:c:1)-O-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[NH;D2;+0:5]-[N;D1;H2:4] | null | [] | null | null | null | null | 2.2 g (8 mmol) of 2-methyl-3-[3-(1-piperidinylmethyl)phenoxy]-1-propanamine in 20 ml of ethanol are stirred together with 1.9 g (8 mmol) of diphenylcarbonate at room temperature for 12 hours. 4 g of hydrazine hydrate is then added to the solution and the reaction mixture is heated under reflux for one hour. Isolation o... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ether.Ether.Primary amine | Acylhydrazine.Urea | c1ccccc1.c1ccccc1 | null | c1ccccc1.C1CC[NH]CC1 | HO- | C(C)O | null | null | CC(CN)COc1cccc(CN2CCCCC2)c1.NN.O=C(Oc1ccccc1)Oc1ccccc1>C(C)O>CC(CNC(=O)NN)COc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0232d71524f549e7b83bb9e370978819 | CN=C=S.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.CN=C=S.CCOCC>>CNC(=S)NNC(NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S | [CH3:1][N:2]=[C:3]=[S:4].[NH2:5][NH:6][C:7](=[S:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26]1>>[CH3:1][NH:2][C:3](=[S:4])[NH:5][NH:6][C:7](=[S:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][... | CN=C=S.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d20aaa746dc43df2f35648d9419db98ed96f2035bae3684b9a4378845ffa3585 | f7e2fc7ab2c341a9e6af0d77ebfb73e49e2475bed2a1247a7f61366f6427f2cf | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[S;D1;H0:9]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[S;D1;H0:9])-[NH;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | 8 | HOUR | 1.62 g (5 mmol) of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydrazine carbothioamide are dissolved in 30 ml of THF, 0.44 g (6 mmol) of methyl isothiocyanate are added, and the reaction mixture is left to stand overnight at room temperature. Ether is added to complete precipitation and the precipitate formed is sucti... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isothiocyanate | Hydrazine.Thiourea | null | null | c1ccccc1.C1CC[NH]CC1 | null | C1CCOC1 | null | 8 | CN=C=S.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>C1CCOC1>CNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d5fc62de4a5646409fb475c73d624309 | CCN=C=S.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C(C)N=C=S>>C(C)NC(=S)NNC(NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S | [CH3:1][CH2:2][N:3]=[C:4]=[S:5].[NH2:6][NH:7][C:8](=[S:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1>>[CH3:1][CH2:2][NH:3][C:4](=[S:5])[NH:6][NH:7][C:8](=[S:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18]... | CCN=C=S.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CCNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d20aaa746dc43df2f35648d9419db98ed96f2035bae3684b9a4378845ffa3585 | f7e2fc7ab2c341a9e6af0d77ebfb73e49e2475bed2a1247a7f61366f6427f2cf | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[C:7]-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[NH;D2;+0:8]-[C:7]-[C;D1;H3:6] | null | [] | null | null | null | null | The above compound is prepared by a method analogous to that of Example 5 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide and ethylisothiocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isothiocyanate | Hydrazine.Thiourea | null | null | c1ccccc1.C1CC[NH]CC1 | null | null | null | null | CCN=C=S.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCNC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-049983a7bc894ccd9b46d98e5ad2a72c | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.S=C=NC1CCCCC1>>S=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C1(CCCCC1)N=C=S>>C1(CCCCC1)NC(=S)NNC(NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S | [S:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1)[NH:21][NH2:22].[C:23](=[S:24])=[N:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1>>[S:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:... | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.S=C=NC1CCCCC1 | S=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d20aaa746dc43df2f35648d9419db98ed96f2035bae3684b9a4378845ffa3585 | f7e2fc7ab2c341a9e6af0d77ebfb73e49e2475bed2a1247a7f61366f6427f2cf | S=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C:6]-[C:7](-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10])-[C:11]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[NH;D2;+0:8]-[C:7](-[C:6])-[C:11] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 5 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydrazine carbothioamide and cyclohexylisothiocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isothiocyanate | Hydrazine.Thiourea | null | null | c1ccccc1.C1CC[NH]CC1.C1CCCCC1 | null | null | null | null | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.S=C=NC1CCCCC1>>S=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-81260fd740e24913832b9d137938d376 | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C(N=C=S)c1ccccc1>>O=C(NC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)c1ccccc1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(=S)NNC(NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S | [NH2:6][NH:7][C:8](=[S:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1.[O:1]=[C:2]([N:3]=[C:4]=[S:5])[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[O:1]=[C:2]([NH:3][C:4](=[S:5])[NH:6][NH:7][C:8](=[S:9])[NH:10][CH2:11][CH2:12][C... | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C(N=C=S)c1ccccc1 | O=C(NC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d20aaa746dc43df2f35648d9419db98ed96f2035bae3684b9a4378845ffa3585 | f7e2fc7ab2c341a9e6af0d77ebfb73e49e2475bed2a1247a7f61366f6427f2cf | O=C(NC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)c1ccccc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[O;D1;H0:6]=[C:7](-[c:8])-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[S;D1;H0:11]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[S;D1;H0:11])-[NH;D2;+0:9]-[C:7](=[O;D1;H0:6])-[c:8] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 5 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl] hydrazine carbothioamide and benzoyl isothiocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isothiocyanate | Hydrazine.Thiourea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | null | null | null | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C(N=C=S)c1ccccc1>>O=C(NC(=S)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fc8d952f1485405099b4c829a6ef36c1 | CN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.CN=C=O.CCOCC>>CNC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][N:2]=[C:3]=[O:4].[NH2:5][NH:6][C:7](=[S:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26]1>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][NH:6][C:7](=[S:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][... | CN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and diazo | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | 8 | HOUR | 1.62 g (5 mmol) of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydrazine carbothioamide are dissolved in 30 ml of THF, 0.40 g (6 mmol) of methylisocyanate are added and the reaction mixture is left to stand overnight at room temperature. Ether is added to complete the precipitation, and the precipitate is suction filte... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1 | null | C1CCOC1 | null | 8 | CN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>C1CCOC1>CNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-72bdb0e1565e47cbbca78c02ea5bd9c4 | CCN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C(C)N=C=O>>C(C)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][NH:7][C:8](=[S:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][NH:7][C:8](=[S:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18]... | CCN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[C:7]-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;D1;H0:10]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:8]-[C:7]-[C;D1;H3:6] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 9 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide and ethyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1 | null | null | null | null | CCN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c8badcb2ff2d4488bfd347f19c735655 | CC(C)N=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CC(C)NC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C(C)(C)N=C=O>>C(C)(C)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].[NH2:7][NH:8][C:9](=[S:10])[NH:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20]([CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[cH:28]1>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[NH:7][NH:8][C:9](=[S:10])[NH:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH... | CC(C)N=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CC(C)NC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:9]-[C:7](-[C;D1;H3:6])-[C;D1;H3:8] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 9 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide and isopropyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1 | null | null | null | null | CC(C)N=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CC(C)NC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c86fc35ded4042d5a2cef2319811c188 | CCCCN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCCCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C(CCC)N=C=O>>C(CCC)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[O:7].[NH2:8][NH:9][C:10](=[S:11])[NH:12][CH2:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][cH:20][c:21]([CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[NH:8][NH:9][C:10](=[S:11])[NH:12][CH2:13][CH2:14][CH2:15][O... | CCCCN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | CCCCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C:6]-[C:7]-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;D1;H0:10]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 9 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide and n-butylisocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1 | null | null | null | null | CCCCN=C=O.NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1>>CCCCNC(=O)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f93ce2cd39ff47738303912fa288c6fc | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NCc1ccccc1>>O=C(NCc1ccccc1)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C(C1=CC=CC=C1)N=C=O>>C(C1=CC=CC=C1)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [NH2:11][NH:12][C:13](=[S:14])[NH:15][CH2:16][CH2:17][CH2:18][O:19][c:20]1[cH:21][cH:22][cH:23][c:24]([CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[cH:32]1.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][NH:12][C:13](=[S... | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NCc1ccccc1 | O=C(NCc1ccccc1)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | O=C(NCc1ccccc1)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[C:9]-[c:10]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[NH;D2;+0:8]-[C:9]-[c:10] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 9 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide and benzyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.c1ccccc1.C1CC[NH]CC1 | null | null | null | null | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NCc1ccccc1>>O=C(NCc1ccccc1)NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a7b9b934c33046b183af7849a44c12d5 | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccccc1>>O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccccc1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.C1(=CC=CC=C1)N=C=O>>C1(=CC=CC=C1)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [NH2:3][NH:4][C:5](=[S:6])[NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1.[O:1]=[C:2]=[N:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[O:1]=[C:2]([NH:3][NH:4][C:5](=[S:6])[NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:... | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccccc1 | O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccccc1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccccc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 9 from N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-hydrazine carbothioamide and phenyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | null | null | null | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccccc1>>O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-dffbaa0d9e044330a4d2895ea18a8ae7 | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccc(Cl)cc1>>O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccc(Cl)cc1 | N1(CCCCC1)CC=1C=C(OCCCNC(=S)NN)C=CC1.ClC1=CC=C(C=C1)N=C=O>>ClC1=CC=C(C=C1)NC(=O)NNC(=S)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [NH2:3][NH:4][C:5](=[S:6])[NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24]1.[O:1]=[C:2]=[N:25][c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[O:1]=[C:2]([NH:3][NH:4][C:5](=[S:6])[NH:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH... | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccc(Cl)cc1 | O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccc(Cl)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | 4cc4a1adc9245e9f94c26bab10e9433acf819602590c48e1d2f1cb274270f2bb | ff86715ec0916d8bbede65b7f01907f953cbdc6bb1bc08ee40ccb9bbc2c92974 | O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccccc1 | [#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#7:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 9 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carbothioamide and 4-chlorophenyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate | Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | null | null | null | NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1.O=C=Nc1ccc(Cl)cc1>>O=C(NNC(=S)NCCCOc1cccc(CN2CCCCC2)c1)Nc1ccc(Cl)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-43d9b13e76d64c13a9297ad2f6e9042c | CN=C=S.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CNC(=S)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CN=C=S.N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1>>CNC(NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S | [CH3:1][N:2]=[C:3]=[S:4].[NH2:5][NH:6][C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26]1>>[CH3:1][NH:2][C:3](=[S:4])[NH:5][NH:6][C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][... | CN=C=S.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CNC(=S)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8cf946e319fae8c1c495a5ba581fadb7c0a794a27016cbc27d27b73b384322f9 | 05e50e03804c76371713bad755bbf759c85fdf6adcd49cbcec177943dc928c98 | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[S;D1;H0:9]>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[S;D1;H0:9])-[NH;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | 12 | HOUR | 0.5 g (6.6 mmol) of methylisothiocyanate are added to 1.0 g (3.3 mmol) of N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-hydrazine carboxamide in 20 ml of THF and the mixture is stirred at room temperature for 12 hours. The precipitate obtained is filtered off and recrystallised from ethanol. The analytical values are s... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isothiocyanate | Acylhydrazine.Thiourea | null | null | c1ccccc1.C1CC[NH]CC1 | null | C1CCOC1 | null | 12 | CN=C=S.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>C1CCOC1>CNC(=S)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ac82a5d73f44449eb39c524e073e15f2 | CCN=C=S.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CCNC(=S)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.C(C)N=C=S>>C(C)NC(NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S | [CH3:1][CH2:2][N:3]=[C:4]=[S:5].[NH2:6][NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27]1>>[CH3:1][CH2:2][NH:3][C:4](=[S:5])[NH:6][NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18]... | CCN=C=S.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CCNC(=S)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8cf946e319fae8c1c495a5ba581fadb7c0a794a27016cbc27d27b73b384322f9 | 05e50e03804c76371713bad755bbf759c85fdf6adcd49cbcec177943dc928c98 | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[C:7]-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10]>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[NH;D2;+0:8]-[C:7]-[C;D1;H3:6] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 17 from N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-hydrazine carboxamide and ethyl isothiocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isothiocyanate | Acylhydrazine.Thiourea | null | null | c1ccccc1.C1CC[NH]CC1 | null | null | null | null | CCN=C=S.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CCNC(=S)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-db19988b81484840bd818ac30406bb9b | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.S=C=NC1CCCCC1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.C1(CCCCC1)N=C=S>>C1(CCCCC1)NC(NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1)=S | [O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1)[NH:21][NH2:22].[C:23](=[S:24])=[N:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:... | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.S=C=NC1CCCCC1 | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8cf946e319fae8c1c495a5ba581fadb7c0a794a27016cbc27d27b73b384322f9 | 05e50e03804c76371713bad755bbf759c85fdf6adcd49cbcec177943dc928c98 | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH2;D1;+0:6].[C:7]-[C:8](-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[S;D1;H0:11])-[C:12]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[S;D1;H0:11])-[NH;D2;+0:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[#7:2]-[C:1])-[C:12] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 17 from N-[3-[3-(1-piperidinylmethyl) phenoxy]propyl]-hydrazine carboxamide and cyclohexyl isothiocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isothiocyanate | Acylhydrazine.Thiourea | null | null | c1ccccc1.C1CC[NH]CC1.C1CCCCC1 | null | null | null | null | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.S=C=NC1CCCCC1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=S)NC1CCCCC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-897436588fc9496aa5f9329bc5f5f2e2 | CN=C=O.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CN=C=O.N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1>>CNC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][N:2]=[C:3]=[O:4].[NH2:5][NH:6][C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26]1>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][NH:6][C:7](=[O:8])[NH:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][... | CN=C=O.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and diazo | b3b2931bd2f458b740f4abeeb31be326a594e840cc88c239f579c7da38d94f79 | 18d79401d6eac6ed3131910c52d959f2123a060f589e449c7bbc9c4932d9ad2f | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | 1 | HOUR | 0.8 ml (13 mmol) of methylisocyanate are added to 2.0 g (6.6 mmol) of N-[3-[3-(1-piperidinylmethyl)phenoxy]-propyl]-hydrazine carboxamide in 20 ml of THF and the reaction mixture is stirred at room temperature for one hour. The precipitate is filtered off and recrystallised from methanol. The analytical values are summ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isocyanate | Acylhydrazine.Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1 | null | C1CCOC1 | null | 1 | CN=C=O.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>C1CCOC1>CNC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ea4f98007ccd45e0b041cf7726349a40 | CC(C)N=C=O.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CC(C)NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.C(C)(C)N=C=O>>C(C)(C)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].[NH2:7][NH:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20]([CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[cH:28]1>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[NH:7][NH:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH... | CC(C)N=C=O.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | CC(C)NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | b3b2931bd2f458b740f4abeeb31be326a594e840cc88c239f579c7da38d94f79 | 18d79401d6eac6ed3131910c52d959f2123a060f589e449c7bbc9c4932d9ad2f | c1ccc(CN2CCCCC2)cc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH2;D1;+0:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[NH;D2;+0:5]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:9]-[C:7](-[C;D1;H3:6])-[C;D1;H3:8] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 20 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carboxamide and isopropyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isocyanate | Acylhydrazine.Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1 | null | null | null | null | CC(C)N=C=O.NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1>>CC(C)NC(=O)NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-62fc6ffbbc9541a0b667151e506b814b | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NC1CCCCC1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NC1CCCCC1 | N1(CCCCC1)CC=1C=C(OCCCNC(=O)NN)C=CC1.C1(CCCCC1)N=C=O>>C1(CCCCC1)NC(=O)NNC(=O)NCCCOC1=CC(=CC=C1)CN1CCCCC1 | [O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1)[NH:21][NH2:22].[C:23](=[O:24])=[N:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH2:13][N:... | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NC1CCCCC1 | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NC1CCCCC1 | null | null | null | Acylation | Urea synthesis via isocyanate and diazo | b3b2931bd2f458b740f4abeeb31be326a594e840cc88c239f579c7da38d94f79 | 18d79401d6eac6ed3131910c52d959f2123a060f589e449c7bbc9c4932d9ad2f | O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NC1CCCCC1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[NH2;D1;+0:6].[C:7]-[C:8](-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=[O;D1;H0:11])-[C:12]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[NH;D2;+0:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[#7:2]-[C:1])-[C:12] | null | [] | null | null | null | null | The compound is prepared by a method analogous to that of Example 20 from N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-hydrazine carboxamide and cyclohexyl isocyanate. The analytical values are summarized in Table I.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Isocyanate | Acylhydrazine.Acylhydrazine.Urea | null | null | c1ccccc1.C1CC[NH]CC1.C1CCCCC1 | null | null | null | null | NNC(=O)NCCCOc1cccc(CN2CCCCC2)c1.O=C=NC1CCCCC1>>O=C(NCCCOc1cccc(CN2CCCCC2)c1)NNC(=O)NC1CCCCC1 |
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