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-c34472859da14a81bfe0f74e60f15c43 | ord-a4cfa4d84dac4bab831418d092d51e52 | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2cccc(C(F)(F)F)c2)SC2CC(=O)N12>>O=C([O-])C1=C(Oc2cccc(C(F)(F)F)c2)SC2CC(=O)N12 | O=C1CC2SC(=C(N12)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC(=CC=C1)C(F)(F)F.C([O-])(O)=O.[Na+]>>O=C1CC2SC(=C(N12)C(=O)[O-])OC1=CC(=CC=C1)C(F)(F)F.[Na+] | O=[N+]([O-])c1ccc(C[O:3][C:2](=[O:1])[C:4]2=[C:5]([O:6][c:7]3[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]3)[S:17][CH:18]3[CH2:19][C:20](=[O:21])[N:22]23)cc1>>[O:1]=[C:2]([O-:3])[C:4]1=[C:5]([O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]2)[S:17][CH:18]2[CH2:19][C:20](=[O:21])... | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2cccc(C(F)(F)F)c2)SC2CC(=O)N12 | O=C([O-])C1=C(Oc2cccc(C(F)(F)F)c2)SC2CC(=O)N12 | null | [Pd] | O1CCOCC1.O | Miscellaneous | Ester to carboxylate | 44f4ca8fa6db8bf6ed2065c1ada1557da240f35fc0d170173f2ffb8dd19aae75 | 572c1e76b1abdca43e2a1bb50332b6c1ee49391ecad01eed2f9507f24676fa6d | O=C1CC2SC(Oc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5](-[#8:6])-[#16:7])-[#7:8]-[C:9]=[O;D1;H0:10]):c:c:1>>[#16:7]-[C:5](-[#8:6])=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | null | null | A mixture of a solution of 602 mg of 4-nitrobenzyl 7-oxo-3-(3-trifluoromethylphenoxy)-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 108 mg sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 60 minutes.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | null | c1ccccc1 | null | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2cccc(C(F)(F)F)c2)SC2CC(=O)N12>[Pd].O1CCOCC1.O>O=C([O-])C1=C(Oc2cccc(C(F)(F)F)c2)SC2CC(=O)N12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a21876ed30be4c5880830910e25f5acc | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1cccc2ccccc12)C(=O)C(C)(C)C.ClCl>>CC(C)(C)C(=O)C(Oc1cccc2ccccc12)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | C(C=C)SC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=CC2=CC=CC=C12)=O.ClCl>>ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=CC2=CC=CC=C12)=O | C=CCS[CH:37]1[N:33]([C:19](=[C:7]([C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[O:8][c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[C:20](=[S:21])[O:22][CH2:23][c:24]2[cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[cH:31][cH:32]2)[C:34](=[O:35])[CH2:36]1.Cl[Cl:38]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:... | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1cccc2ccccc12)C(=O)C(C)(C)C.ClCl | CC(C)(C)C(=O)C(Oc1cccc2ccccc12)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl | null | null | ClCCl.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d4a1f45948ca6338d13758a8eb064414f490d5560b79b989b8f902e12590b6c8 | 7fecd9068ed121180c7c8f39a016405d4e3d2c3ae4d3dd36c097f13d461df37e | O=C1CCN1C(=COc1cccc2ccccc12)C(=S)OCc1ccccc1 | C=C-C-S-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-1-[C:6](-[C:7](-[#8:8])=[S;D1;H0:9])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13].Cl-[Cl;H0;D1;+0:14]>>[#8:8]-[C:7](=[S;D1;H0:9])-[C:6](-[#7:5]1-[C:3](=[O;D1;H0:4])-[C:2]-[CH;D3;+0:1]-1-[Cl;H0;D1;+0:14])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13] | 73.7 | [{"value": 73.7, "product": "ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=CC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7.1 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(1-naphthyloxy)-3-trimethylacetylthiopropenate in dichloromethane at -20° was added a solution of 23 mmol of chlorine in carbon tetrachloride. After 30 minutes the mixture was warmed to room temperature, evaporated in vacuo, and the residual oi... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Allyl | Secondary halide | C1C[NH]C1 | C1C[NH]C1 | c1ccc2ccccc2c1.c1ccccc1.C1C[NH]C1 | HCl | ClCCl.C(Cl)(Cl)(Cl)Cl | null | null | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1cccc2ccccc12)C(=O)C(C)(C)C.ClCl>ClCCl.C(Cl)(Cl)(Cl)Cl>CC(C)(C)C(=O)C(Oc1cccc2ccccc12)=C(C(=S)OCc1ccc([N+](=O)[O-])cc1)N1C(=O)CC1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5f54f4ebec484876b29f0018a9c011bd | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2cccc3ccccc23)SC2CC(=O)N12>>O=C([O-])C1=C(Oc2cccc3ccccc23)SC2CC(=O)N12 | C1(=CC=CC2=CC=CC=C12)OC1=C(N2C(CC2S1)=O)C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-].C([O-])(O)=O.[Na+]>>C1(=CC=CC2=CC=CC=C12)OC1=C(N2C(CC2S1)=O)C(=O)[O-].[Na+] | O=[N+]([O-])c1ccc(C[O:3][C:2](=[O:1])[C:4]2=[C:5]([O:6][c:7]3[cH:8][cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]34)[S:17][CH:18]3[CH2:19][C:20](=[O:21])[N:22]23)cc1>>[O:1]=[C:2]([O-:3])[C:4]1=[C:5]([O:6][c:7]2[cH:8][cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[S:17][CH:18]2[CH2:19][C:20](=[O:21])[N... | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2cccc3ccccc23)SC2CC(=O)N12 | O=C([O-])C1=C(Oc2cccc3ccccc23)SC2CC(=O)N12 | null | [Pd] | O1CCOCC1.O | Miscellaneous | Ester to carboxylate | 44f4ca8fa6db8bf6ed2065c1ada1557da240f35fc0d170173f2ffb8dd19aae75 | 572c1e76b1abdca43e2a1bb50332b6c1ee49391ecad01eed2f9507f24676fa6d | O=C1CC2SC(Oc3cccc4ccccc34)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5](-[#8:6])-[#16:7])-[#7:8]-[C:9]=[O;D1;H0:10]):c:c:1>>[#16:7]-[C:5](-[#8:6])=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | null | null | A mixture of a solution of 800 mg of 4-nitrobenzyl 3-(1-naphthyloxy)-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 150 mg of sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 60 minutes.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | null | c1ccccc1 | null | c1ccc2ccccc2c1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | O=C(OCc1ccc([N+](=O)[O-])cc1)C1=C(Oc2cccc3ccccc23)SC2CC(=O)N12>[Pd].O1CCOCC1.O>O=C([O-])C1=C(Oc2cccc3ccccc23)SC2CC(=O)N12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8bbbfe7fd6c44376ad072001ed220af4 | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Sc1ccc(C)cc1)C(=O)C(C)(C)C.ClCl>>Cc1ccc(SC(C(=O)C(C)(C)C)=C(C(=S)OCc2ccc([N+](=O)[O-])cc2)N2C(=O)CC2Cl)cc1 | C(C=C)SC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)SC1=CC=C(C=C1)C)=O.ClCl>>ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)SC1=CC=C(C=C1)C)=O | C=CCS[CH:32]1[N:28]([C:14](=[C:7]([S:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]2)[C:8](=[O:9])[C:10]([CH3:11])([CH3:12])[CH3:13])[C:15](=[S:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26][cH:27]2)[C:29](=[O:30])[CH2:31]1.Cl[Cl:33]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6][C:7]([C:8](=[O:... | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Sc1ccc(C)cc1)C(=O)C(C)(C)C.ClCl | Cc1ccc(SC(C(=O)C(C)(C)C)=C(C(=S)OCc2ccc([N+](=O)[O-])cc2)N2C(=O)CC2Cl)cc1 | null | null | ClCCl.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d4a1f45948ca6338d13758a8eb064414f490d5560b79b989b8f902e12590b6c8 | 7fecd9068ed121180c7c8f39a016405d4e3d2c3ae4d3dd36c097f13d461df37e | O=C1CCN1C(=CSc1ccccc1)C(=S)OCc1ccccc1 | C=C-C-S-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-1-[C:6](-[C:7](-[#8:8])=[S;D1;H0:9])=[C:10](-[#16:11])-[C:12]=[O;D1;H0:13].Cl-[Cl;H0;D1;+0:14]>>[#16:11]-[C:10](-[C:12]=[O;D1;H0:13])=[C:6](-[#7:5]1-[C:3](=[O;D1;H0:4])-[C:2]-[CH;D3;+0:1]-1-[Cl;H0;D1;+0:14])-[C:7](-[#8:8])=[S;D1;H0:9] | 69.5 | [{"value": 69.5, "product": "ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)SC1=CC=C(C=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2.28 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-methylthiophenoxy)-3-trimethylacetylthiopropenate in dichloromethane at -20° , was added solution of 7.6 mmol of chlorine in carbon tetrachloride. After 30 minutes the mixture was warmed to room temperature, evaporated in vacuo, and the res... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Allyl | Secondary halide | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.c1ccccc1.C1C[NH]C1 | HCl | ClCCl.C(Cl)(Cl)(Cl)Cl | null | null | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Sc1ccc(C)cc1)C(=O)C(C)(C)C.ClCl>ClCCl.C(Cl)(Cl)(Cl)Cl>Cc1ccc(SC(C(=O)C(C)(C)C)=C(C(=S)OCc2ccc([N+](=O)[O-])cc2)N2C(=O)CC2Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-708832323170435e8c8a68dfd1f9ceec | Cc1ccc(SC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>>Cc1ccc(SC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | CC1=CC=C(SC2=C(N3C(CC3S2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1.C([O-])(O)=O.[Na+]>>CC1=CC=C(SC2=C(N3C(CC3S2)=O)C(=O)[O-])C=C1.[Na+] | O=[N+]([O-])c1ccc(C[O:11][C:9]([C:8]2=[C:7]([S:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]3)[S:17][CH:16]3[N:12]2[C:13](=[O:14])[CH2:15]3)=[O:10])cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6][C:7]2=[C:8]([C:9](=[O:10])[O-:11])[N:12]3[C:13](=[O:14])[CH2:15][CH:16]3[S:17]2)[cH:18][cH:19]1 | Cc1ccc(SC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1 | Cc1ccc(SC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | null | [Pd] | O1CCOCC1.O | Miscellaneous | Ester to carboxylate | 44f4ca8fa6db8bf6ed2065c1ada1557da240f35fc0d170173f2ffb8dd19aae75 | 572c1e76b1abdca43e2a1bb50332b6c1ee49391ecad01eed2f9507f24676fa6d | O=C1CC2SC(Sc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5](-[#16:6])-[#16:7])-[#7:8]-[C:9]=[O;D1;H0:10]):c:c:1>>[#16:7]-[C:5](-[#16:6])=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | null | null | A mixture of a solution of 70 mg of 4-nitrobenzyl 3-(4-methylthiophenoxy)-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 13 mg of sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 35° for 60 minutes.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | null | c1ccccc1 | null | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | Cc1ccc(SC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>[Pd].O1CCOCC1.O>Cc1ccc(SC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7c95f89235eb4b3db8041d63efaff3e4 | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(S(C)=O)cc1)C(=O)C(C)(C)C.ClCl>>CS(=O)c1ccc(OC(C(=O)C(C)(C)C)=C(C(=S)OCc2ccc([N+](=O)[O-])cc2)N2C(=O)CC2Cl)cc1 | C(C=C)SC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)S(=O)C)=O.ClCl>>ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)S(=O)C)=O | C=CCS[CH:34]1[N:30]([C:16](=[C:9]([O:8][c:7]2[cH:6][cH:5][c:4]([S:2]([CH3:1])=[O:3])[cH:37][cH:36]2)[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[C:17](=[S:18])[O:19][CH2:20][c:21]2[cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]2)[C:31](=[O:32])[CH2:33]1.Cl[Cl:35]>>[CH3:1][S:2](=[O:3])[c:4]1[cH:5][cH:6... | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(S(C)=O)cc1)C(=O)C(C)(C)C.ClCl | CS(=O)c1ccc(OC(C(=O)C(C)(C)C)=C(C(=S)OCc2ccc([N+](=O)[O-])cc2)N2C(=O)CC2Cl)cc1 | null | null | ClCCl.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d4a1f45948ca6338d13758a8eb064414f490d5560b79b989b8f902e12590b6c8 | 7fecd9068ed121180c7c8f39a016405d4e3d2c3ae4d3dd36c097f13d461df37e | O=C1CCN1C(=COc1ccccc1)C(=S)OCc1ccccc1 | C=C-C-S-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-1-[C:6](-[C:7](-[#8:8])=[S;D1;H0:9])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13].Cl-[Cl;H0;D1;+0:14]>>[#8:8]-[C:7](=[S;D1;H0:9])-[C:6](-[#7:5]1-[C:3](=[O;D1;H0:4])-[C:2]-[CH;D3;+0:1]-1-[Cl;H0;D1;+0:14])=[C:10](-[#8:11])-[C:12]=[O;D1;H0:13] | 52.5 | [{"value": 52.5, "product": "ClC1CC(N1C(C(=S)OCC1=CC=C(C=C1)[N+](=O)[O-])=C(C(C(C)(C)C)=O)OC1=CC=C(C=C1)S(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.488 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-methylsulphinylphenoxy)-3-trimethylacetylthiopropenate in dichloromethane at -20°, was added dropwise a solution of 1.58 mmol of chlorine in carbon tetrachloride. After 30 minutes the mixture was warmed to room temperature, evaporated in v... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Allyl | Secondary halide | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.c1ccccc1.C1C[NH]C1 | HCl | ClCCl.C(Cl)(Cl)(Cl)Cl | null | null | C=CCSC1CC(=O)N1C(C(=S)OCc1ccc([N+](=O)[O-])cc1)=C(Oc1ccc(S(C)=O)cc1)C(=O)C(C)(C)C.ClCl>ClCCl.C(Cl)(Cl)(Cl)Cl>CS(=O)c1ccc(OC(C(=O)C(C)(C)C)=C(C(=S)OCc2ccc([N+](=O)[O-])cc2)N2C(=O)CC2Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3d2edff3e0434297b73939225c1538f0 | CS(=O)c1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>>CS(=O)c1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | CS(=O)C1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C=C1.C([O-])(O)=O.[Na+]>>CS(=O)C1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)[O-])C=C1.[Na+] | O=[N+]([O-])c1ccc(C[O:13][C:11]([C:10]2=[C:9]([O:8][c:7]3[cH:6][cH:5][c:4]([S:2]([CH3:1])=[O:3])[cH:21][cH:20]3)[S:19][CH:18]3[N:14]2[C:15](=[O:16])[CH2:17]3)=[O:12])cc1>>[CH3:1][S:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][C:9]2=[C:10]([C:11](=[O:12])[O-:13])[N:14]3[C:15](=[O:16])[CH2:17][CH:18]3[S:19]2)[cH:20][cH:21]1 | CS(=O)c1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1 | CS(=O)c1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 | null | [Pd] | O1CCOCC1.O | Miscellaneous | Ester to carboxylate | 44f4ca8fa6db8bf6ed2065c1ada1557da240f35fc0d170173f2ffb8dd19aae75 | 572c1e76b1abdca43e2a1bb50332b6c1ee49391ecad01eed2f9507f24676fa6d | O=C1CC2SC(Oc3ccccc3)=CN12 | O=[N+](-[O-])-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5](-[#8:6])-[#16:7])-[#7:8]-[C:9]=[O;D1;H0:10]):c:c:1>>[#16:7]-[C:5](-[#8:6])=[C:4](-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3])-[#7:8]-[C:9]=[O;D1;H0:10] | 109.8 | [{"value": 109.8, "product": "CS(=O)C1=CC=C(OC2=C(N3C(CC3S2)=O)C(=O)[O-])C=C1.[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of a solution of 70 mg of 4-nitrobenzyl 3-(4-methylsulphinylphenoxy)-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 13 mg of sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 60 minutes. Then, the mixture was filtered through Gelite, and lyop... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | null | c1ccccc1 | null | c1ccccc1.C1=CN2CCC2S1 | HO- | [Pd].O1CCOCC1.O | null | null | CS(=O)c1ccc(OC2=C(C(=O)OCc3ccc([N+](=O)[O-])cc3)N3C(=O)CC3S2)cc1>[Pd].O1CCOCC1.O>CS(=O)c1ccc(OC2=C(C(=O)[O-])N3C(=O)CC3S2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dc0b89bdedb5477fb9033545f5af6b61 | CC(C)(C)OC(=O)CI.NC1Cc2ccccc2NC1=O>>CC(C)(C)OC(=O)CN1C(=O)C(N)Cc2ccccc21 | Cl.NC1C(NC2=CC=CC=C2C1)=O.[H-].[Na+].ICC(=O)OC(C)(C)C.[H][H]>>C(C)(C)(C)OC(=O)CN1C(=O)C(CC2=CC=CC=C12)N | I[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:9]1[C:10](=[O:11])[CH:12]([NH2:13])[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][N:9]1[C:10](=[O:11])[CH:12]([NH2:13])[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | CC(C)(C)OC(=O)CI.NC1Cc2ccccc2NC1=O | CC(C)(C)OC(=O)CN1C(=O)C(N)Cc2ccccc21 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Boc amine protection (ethyl Boc) | 00bdf42034ad419e8a7421c967f14ba303b548b011e99dd40ab321f2309531bf | 933a6f1013d44497c9c5902b73c24fbdc7813d20b886bdbc4c670d5b43ca2182 | O=C1CCc2ccccc2N1 | I-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]-[C:10](=[O;D1;H0:11])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C:9]-[C:10](=[O;D1;H0:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-[c:13](:[c:14]):[c:15] | 73 | [{"value": 73.0, "product": "C(C)(C)(C)OC(=O)CN1C(=O)C(CC2=CC=CC=C12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 2.42 gm NaH (50% oil dispersion washed 3×hexanes) in 50 ml of THF at 0° C. was added solid 5 gm (0.025 mol) of 3-aminodihydrocarbostyrilhydrochloride (T. J. McCord, Arch. of Biochem. & Biophys. 102 48 (1963)) stirring at 0° C. until the evolution of hydrogen had ceased at which time the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide | Ester.Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | HI | C1CCOC1 | null | 1 | CC(C)(C)OC(=O)CI.NC1Cc2ccccc2NC1=O>C1CCOC1>CC(C)(C)OC(=O)CN1C(=O)C(N)Cc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-68c35c50649b4a169b7dad29368e7ca8 | C1=CCC2SC=CC2=C1.CC(=O)N(C)C>>CC(=O)c1cc2ccccc2s1 | S1C=CC=2C1CC=CC2.[OH-].[K+].CC(=O)N(C)C.Cl>>C(C)(=O)C=1SC2=C(C1)C=CC=C2 | [CH:4]1=[CH:5][C:6]2=[CH:7][CH:8]=[CH:9][CH2:10][CH:11]2[S:12]1.CN(C)[C:2]([CH3:1])=[O:3]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[s:12]1 | C1=CCC2SC=CC2=C1.CC(=O)N(C)C | CC(=O)c1cc2ccccc2s1 | null | [Cu] | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 51f37af0025519de3472ec47d2ee9cf1eea9f404aa794312c364cac875b2133a | 738ebe845e134b97f5c03ccfa6305783ef5d7282ba500cda23b85f728978db4f | c1ccc2sccc2c1 | C-N(-C)-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[CH2;D2;+0:4]1-[CH;D2;+0:5]=[CH;D2;+0:6]-[CH;D2;+0:7]=[C;H0;D3;+0:8]2-[CH;D2;+0:9]=[CH;D2;+0:10]-[S;H0;D2;+0:11]-[CH;D3;+0:12]-1-2>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:10]1:[cH;D2;+0:9]:[c;H0;D3;+0:8]2:[cH;D2;+0:7]:[cH;D2;+0:6]:[cH;D2;+0:5]:[cH;D2;+0:4]:... | 70 | [{"value": 70.0, "product": "C(C)(=O)C=1SC2=C(C1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The amino ester (2) was converted to the diazonium salt and reduced by boiling in ethanol containing finely divided copper to give the pure ester (3). Hydrolysis of the ester with aqueous ethanolic KOH followed by acidification with 5M HCl, gave the acid (4) in approximately 70% yield. The acid was converted to the cor... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Conjugated diene | Ketone | C1=CCC2SC=CC2=C1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | Other | [Cu].C(C)O | null | null | C1=CCC2SC=CC2=C1.CC(=O)N(C)C>[Cu].C(C)O>CC(=O)c1cc2ccccc2s1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4fc6a07ca93446d38317ff7a8bd2f484 | C=C(Cl)C#N.NNc1ccccc1>>Nc1ccnn1-c1ccccc1 | [OH-].[Na+].C1(=CC=CC=C1)NN.ClC(C#N)=C>>C1(=CC=CC=C1)N1N=CC=C1N | Cl[C:3]([C:2]#[N:1])=[CH2:4].[NH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[NH2:1][c:2]1[cH:3][cH:4][n:5][n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=C(Cl)C#N.NNc1ccccc1 | Nc1ccnn1-c1ccccc1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 73db7ff77744011e446624a12a8f2967f91e152d48aa4b0429cb6519236bbd1a | 0ef1207b247725ba3e9988175e67d1a1cbc24b547bfa121f8d76996eaac432f4 | c1ccc(-n2cccn2)cc1 | Cl-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[NH2;D1;+0:5]-[NH;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[NH2;D1;+0:4]-[c;H0;D3;+0:3]1:[cH;D2;+0:1]:[cH;D2;+0:2]:[n;H0;D2;+0:5]:[n;H0;D3;+0:6]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | null | [] | null | null | 6 | HOUR | To a mixture consisting of 680 parts water, 216 parts of phenylhydrazine and 164 parts of 2-chloroacrylonitrile 220 parts of a 30% sodium hydroxide solution are added dropwise at room temperature. After six hours the reaction is completed. The resulting 1-phenyl-5-aminopyrazole is isolated from that phase which has bee... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Alkenyl halide.Nitrile.Vinyl | Primary amine | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccccc1 | HCl | O | null | 6 | C=C(Cl)C#N.NNc1ccccc1>O>Nc1ccnn1-c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7bca2b98e81b4d6c8d6a97745045e45b | O=C(O)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-].O=S(Cl)Cl>>O=C(Cl)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C(=O)O)C=C(C=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl.S(=O)(Cl)Cl>>[N+](=O)([O-])C1=C(C(=O)Cl)C=C(C=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl | O[C:2](=[O:1])[c:4]1[cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]2[Cl:18])[cH:19][cH:20][c:21]1[N+:22](=[O:23])[O-:24].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]2[Cl:18])[cH:19][cH:20][c:21]1[N+:22... | O=C(O)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-].O=S(Cl)Cl | O=C(Cl)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-] | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc(Oc2ccccc2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 0.3 Part of 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid and 0.83 part of thionyl chloride for 2 hours. After the reaction, the excess of thionyl chloride was removed under reduced pressure to give 0.31 part of 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride. The resulting benzoyl chloride wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | O=C(O)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-].O=S(Cl)Cl>>O=C(Cl)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-43deab324a3240d394a7343e641e646e | CC(Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1)C(=O)Cl.CCCCCCCCCCCCO>>CCCCCCCCCCCCOC(=O)C(C)Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1 | FC(C=1C=CC(=NC1)OC1=CC=C(OC(C(=O)Cl)C)C=C1)(F)F.C(CCCCCCCCCCC)O.C(C)N(CC)CC>>FC(C=1C=CC(=NC1)OC1=CC=C(OC(C(=O)OCCCCCCCCCCCC)C)C=C1)(F)F | Cl[C:14](=[O:15])[CH:16]([CH3:17])[O:18][c:19]1[cH:20][cH:21][c:22]([O:23][c:24]2[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][n:33]2)[cH:34][cH:35]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9... | CC(Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1)C(=O)Cl.CCCCCCCCCCCCO | CCCCCCCCCCCCOC(=O)C(C)Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccc(Oc2ccccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4])-[C;D1;H3:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:7]-[C:6] | null | [] | 10 | CELSIUS | null | null | n-Dodecanol(2.5 grams; 0.134mol), toluene (80 ml) and triethylamine (5 ml) were placed into a 300 ml, 3-necked glass reaction flask equipped with stirrer, thermometer, reflux condenser, and nitrogen line. 2-[4-(5-trifluoromethyl-2-pyridinyloxy)phenoxy]propanoic acid chloride (4.45 grams; 0.0125 mol) in toluene (30 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1.c1ccncc1 | HCl | C1(=CC=CC=C1)C | 10 | null | CC(Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1)C(=O)Cl.CCCCCCCCCCCCO>C1(=CC=CC=C1)C>CCCCCCCCCCCCOC(=O)C(C)Oc1ccc(Oc2ccc(C(F)(F)F)cn2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f55734ffe0484999bc43846da7949556 | Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1>>c1ccc(OC(Oc2ccccc2)c2ccccn2)cc1 | ClC1=CC=CC(=N1)C(OC1=CC=CC=C1)OC1=CC=CC=C1.C(C)N(CC)CC.[H][H]>>O(C1=CC=CC=C1)C(C1=NC=CC=C1)OC1=CC=CC=C1 | Cl[c:18]1[cH:17][cH:16][cH:15][c:14]([CH:6]([O:5][c:4]2[cH:3][cH:2][cH:1][cH:21][cH:20]2)[O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:19]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][CH:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][cH:17][cH:18][n:19]2)[cH:20][cH:21]1 | Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 | c1ccc(OC(Oc2ccccc2)c2ccccn2)cc1 | null | [Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | ea85ec2fde5700c76b45764563e70d433b50e38e1af4209f646f155266c8ec96 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(OC(Oc2ccccc2)c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c:4]:[c:5] | null | [] | null | null | null | null | To a solution of 10.42 grams (g) (0.032 mole (m)) of 6-chloro-2-(diphenoxy-methyl)pyridine, 8.02 g (0.079 m) of triethylamine in 200 milliliters (ml) of absolute ethanol in a Parr shaker bottle was added 0.5 g of 5 percent palladium on charcoal. Hydrogen was passed over the liquid surface using a Parr hydrogenator unti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccccc1.c1ccncc1 | Other | [Pd].C(C)O | null | null | Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1>[Pd].C(C)O>c1ccc(OC(Oc2ccccc2)c2ccccn2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b5500c318dd6471eb5ce61af6b4af19b | CCO.Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1>>CCOc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 | [H][H].[Na].C(C)O.[Na].ClC1=CC=CC(=N1)C(OC1=CC=CC=C1)OC1=CC=CC=C1>>C(C)OC1=CC=CC(=N1)C(OC1=CC=CC=C1)OC1=CC=CC=C1 | [CH3:1][CH2:2][OH:3].Cl[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:... | CCO.Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 | CCOc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OC(Oc2ccccc2)c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | 24 | HOUR | To 30.0 ml of ethanol was added 1.10 g of sodium pellets. After the sodium had dissolved, 10.14 g of 6-chloro-2-(diphenoxymethyl)pyridine in 50 ml of DMSO was added dropwise. The mixture was heated to 80° C. and held there for 24 hours. The reaction was considered complete as seen by the NMR. The reaction mixture was c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HCl | O.CS(=O)C | 80 | 24 | CCO.Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1>O.CS(=O)C>CCOc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1c364b92de084a02a850268fe3d787b6 | CS.Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1>>CSc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 | ClC1=CC=CC(=N1)C(OC1=CC=CC=C1)OC1=CC=CC=C1.C[O-].[Na+].[Na].CS>>CSC1=CC=CC(=N1)C(OC1=CC=CC=C1)OC1=CC=CC=C1 | [CH3:1][SH:2].Cl[c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23]1 | CS.Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 | CSc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 | null | null | CS(=O)C.CO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 83e1471f87e837809a4e2fb3e1de305c0d7a6603480e04a86024c7cd55ed85fb | b7fe376f7aad2517725eef26ab981e4baa6c31c5f38fdf89e7c52a4a2c6cc1d2 | c1ccc(OC(Oc2ccccc2)c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[SH;D1;+0:7]>>[C;D1;H3:6]-[S;H0;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 13 | CELSIUS | null | null | To a mixture of sodium methoxide (made from 100 ml (2.47 m) of methanol and 1.50 g (0.652 m) of sodium metal) which had been cooled to 13° C. was added 7.0 ml (0.126 m) of methylmercaptan. The mixture was allowed to warm to room temperature and then 20.0 g of 6-chloro-2-(diphenoxymethyl)pyridine and 150 ml of dimethyls... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aliphatic thiol | Monosulfide | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HCl | CS(=O)C.CO | 13 | null | CS.Clc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1>CS(=O)C.CO>CSc1cccc(C(Oc2ccccc2)Oc2ccccc2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d502269df27c49a786d313339978d5bd | CSC(=NC#N)SC.NS(=O)(=O)c1ccccc1[N+](=O)[O-]>>CSC(=NC#N)NS(=O)(=O)c1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N.CSC(=NC#N)SC.C(=O)([O-])[O-].[K+].[K+]>>C(#N)N=C(NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])SC | CS[C:3]([S:2][CH3:1])=[N:4][C:5]#[N:6].[NH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][S:2][C:3](=[N:4][C:5]#[N:6])[NH:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19] | CSC(=NC#N)SC.NS(=O)(=O)c1ccccc1[N+](=O)[O-] | CSC(=NC#N)NS(=O)(=O)c1ccccc1[N+](=O)[O-] | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ba95383ce51db2717e65e6a878156c5ff7d731f3f5512dc0487b6cd8ce3c344d | 113461c1621d86500c6bddb99471970dcbe90dcd3b57be697f00b24c57c3b50f | c1ccccc1 | C-S-[C;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3])=[#7:4]-[C:5]#[N;D1;H0:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[C;D1;H3:3]-[#16:2]-[C;H0;D3;+0:1](=[#7:4]-[C:5]#[N;D1;H0:6])-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11] | 55 | [{"value": 55.0, "product": "C(#N)N=C(NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.9, "product": "C(#N)N=C(NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 2.02 g (10.0 mmol) of 2-nitrobenzene-sulfonamide, 1.46 g (10.0 mmol) of dimethyl N-cyanodithioiminocarbonate and 1.38 g (10.0 mmol) of powdered, anydrous K2CO3 in 16 ml of acetone was heated at reflux for 20 hours. The reaction mixture was filtered and the solid collected was washed several times with acet... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Monosulfide.Monosulfide | Sulfonamide.Monosulfide | null | null | c1ccccc1 | Other | CC(=O)C | null | 1 | CSC(=NC#N)SC.NS(=O)(=O)c1ccccc1[N+](=O)[O-]>CC(=O)C>CSC(=NC#N)NS(=O)(=O)c1ccccc1[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1be0027e2f07480ca70d4b072b028c1d | CSC(=NC#N)NS(=O)(=O)c1ccccc1[N+](=O)[O-].NN>>Nc1nc(NS(=O)(=O)c2ccccc2[N+](=O)[O-])n[nH]1 | C(#N)N=C(NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])SC.NN>>NC1=NC(=NN1)NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-] | CS[C:4](=[N:3][C:2]#[N:1])[NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17].[NH2:18][NH2:19]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N+:15](=[O:16])[O-:17])[n:18][nH:19]1 | CSC(=NC#N)NS(=O)(=O)c1ccccc1[N+](=O)[O-].NN | Nc1nc(NS(=O)(=O)c2ccccc2[N+](=O)[O-])n[nH]1 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 4334099462ff9bb73d9e35682bf6cbb1a8632d3da77de0bc558fc71a8eb2c1bd | 846c6feeda9d596d616e97acabee3af65330745e99fec7539883dfed54df91fa | O=S(=O)(Nc1nc[nH]n1)c1ccccc1 | C-S-[C;H0;D3;+0:1](-[#7:2]-[#16:3])=[N;H0;D2;+0:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6].[NH2;D1;+0:7]-[NH2;D1;+0:8]>>[#16:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[nH;D2;+0:8]:[c;H0;D3;+0:5](-[NH2;D1;+0:6]):[n;H0;D2;+0:4]:1 | 82.2 | [{"value": 82.2, "product": "NC1=NC(=NN1)NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 9 | DAY | A suspension of 29.4 g (98.0 mmol) of N'-Cyano-N-(2-nitrophenylsulfonyl)-S-methylisothiourea in 100 ml of acetonitrile was treated with 6.2 ml (6.3 g, 0.20 mol) of anhydrous hydrazine. A mild exothermic reaction occurred as the reaction mixture became homogeneous. After stirring for 9 days the precipitated solid was co... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Nitrile.Monosulfide | Primary amine | null | c1nnc[nH]1 | c1nnc[nH]1.c1ccccc1 | Other | C(C)#N | null | 216 | CSC(=NC#N)NS(=O)(=O)c1ccccc1[N+](=O)[O-].NN>C(C)#N>Nc1nc(NS(=O)(=O)c2ccccc2[N+](=O)[O-])n[nH]1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-12c44bf2a720460bb09bece297db259d | CSC(=NC#N)SC.NS(=O)(=O)c1cc(Cl)ccc1Cl>>CSC(=NC#N)NS(=O)(=O)c1cc(Cl)ccc1Cl | ClC1=C(C=C(C=C1)Cl)S(=O)(=O)N.CSC(=NC#N)SC.[OH-].[Na+].Cl>>C(#N)N=C(NS(=O)(=O)C1=C(C=CC(=C1)Cl)Cl)SC | CS[C:3]([S:2][CH3:1])=[N:4][C:5]#[N:6].[NH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][S:2][C:3](=[N:4][C:5]#[N:6])[NH:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[Cl:18] | CSC(=NC#N)SC.NS(=O)(=O)c1cc(Cl)ccc1Cl | CSC(=NC#N)NS(=O)(=O)c1cc(Cl)ccc1Cl | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | ba95383ce51db2717e65e6a878156c5ff7d731f3f5512dc0487b6cd8ce3c344d | 113461c1621d86500c6bddb99471970dcbe90dcd3b57be697f00b24c57c3b50f | c1ccccc1 | C-S-[C;H0;D3;+0:1](-[#16:2]-[C;D1;H3:3])=[#7:4]-[C:5]#[N;D1;H0:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[C;D1;H3:3]-[#16:2]-[C;H0;D3;+0:1](=[#7:4]-[C:5]#[N;D1;H0:6])-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11] | 60.7 | [{"value": 60.7, "product": "C(#N)N=C(NS(=O)(=O)C1=C(C=CC(=C1)Cl)Cl)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 10.6 g (43.2 mmol) of 2,5-dichlorobenzenesulfonamide, 7.15 g (44.0 mmol) of 90 percent dimethyl N-cyanodithioiminocarbonate and 1.8 g (44 mmol) of NaOH in 60 ml of ethanol and 10 ml of H2O was heated at reflux for 6 hours. After cooling to room temperature the reaction mixture was poured into 600 ml of ic... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Monosulfide.Monosulfide | Sulfonamide.Monosulfide | null | null | c1ccccc1 | Other | O.C(C)O | null | null | CSC(=NC#N)SC.NS(=O)(=O)c1cc(Cl)ccc1Cl>O.C(C)O>CSC(=NC#N)NS(=O)(=O)c1cc(Cl)ccc1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6342821919ea4f479e4c2717e781a086 | CSC(=NC#N)NS(=O)(=O)c1cc(Cl)ccc1Cl.NN>>Nc1nc(NS(=O)(=O)c2cc(Cl)ccc2Cl)n[nH]1 | C(#N)N=C(NS(=O)(=O)C1=C(C=CC(=C1)Cl)Cl)SC.O.NN>>NC1=NC(=NN1)NS(=O)(=O)C1=C(C=CC(=C1)Cl)Cl | CS[C:4](=[N:3][C:2]#[N:1])[NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]1[Cl:16].[NH2:17][NH2:18]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][S:6](=[O:7])(=[O:8])[c:9]2[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]2[Cl:16])[n:17][nH:18]1 | CSC(=NC#N)NS(=O)(=O)c1cc(Cl)ccc1Cl.NN | Nc1nc(NS(=O)(=O)c2cc(Cl)ccc2Cl)n[nH]1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 4334099462ff9bb73d9e35682bf6cbb1a8632d3da77de0bc558fc71a8eb2c1bd | 846c6feeda9d596d616e97acabee3af65330745e99fec7539883dfed54df91fa | O=S(=O)(Nc1nc[nH]n1)c1ccccc1 | C-S-[C;H0;D3;+0:1](-[#7:2]-[#16:3])=[N;H0;D2;+0:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6].[NH2;D1;+0:7]-[NH2;D1;+0:8]>>[#16:3]-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[nH;D2;+0:8]:[c;H0;D3;+0:5](-[NH2;D1;+0:6]):[n;H0;D2;+0:4]:1 | 63.2 | [{"value": 57.0, "product": "NC1=NC(=NN1)NS(=O)(=O)C1=C(C=CC(=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "NC1=NC(=NN1)NS(=O)(=O)C1=C(C=CC(=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 8.51 g (26.2 mmol) of N'-cyano-N-(2,5-dichlorophenylsulfonyl)-S-methylisothiourea and 10 ml (10 g, 0.20 mol) of hydrazine monohydrate in 85 ml of ethanol was heated at reflux for 30 minutes. After cooling to room temperature, the solid which separated was collected and suspended in 170 ml of H2O and the su... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Nitrile.Monosulfide | Primary amine | null | c1nnc[nH]1 | c1nnc[nH]1.c1ccccc1 | Other | C(C)O | null | 4 | CSC(=NC#N)NS(=O)(=O)c1cc(Cl)ccc1Cl.NN>C(C)O>Nc1nc(NS(=O)(=O)c2cc(Cl)ccc2Cl)n[nH]1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a3f93e06bdb3443090fa16797409ab1b | CC(=O)Cl.CCOC(C)=N>>CCOC(C)=NC(C)=O | CCOCC.C(C)N(CC)CC.Cl.C(C)(OCC)=N.C(C)(=O)Cl>>C(C)(=O)N=C(C)OCC | Cl[C:7]([CH3:8])=[O:9].[CH3:1][CH2:2][O:3][C:4]([CH3:5])=[NH:6]>>[CH3:1][CH2:2][O:3][C:4]([CH3:5])=[N:6][C:7]([CH3:8])=[O:9] | CC(=O)Cl.CCOC(C)=N | CCOC(C)=NC(C)=O | null | null | C(Cl)Cl | Acylation | OtherReaction | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | null | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[C:5](-[C;D1;H3:6])=[NH;D1;+0:7]>>[#8:4]-[C:5](-[C;D1;H3:6])=[N;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 1 | HOUR | A slurry of 50.0 gm (405 mmol) of ethyl acetimidate hydrochloride in 500 ml of methylene chloride was mechanically stirred and treated dropwise with 81.9 gm (809 mmol) of triethylamine while keeping the temperature at less than 25° C. The resulting slurry was then treated dropwise with 31.8 gm (405 mmol) of acetyl chlo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | null | HCl | C(Cl)Cl | null | 1 | CC(=O)Cl.CCOC(C)=N>C(Cl)Cl>CCOC(C)=NC(C)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3873046c49ec48d7830f08215588ea91 | C=O.COc1cc(C)nc(N)n1.Sc1ccc(Cl)cc1>>COc1cc(C)nc(NCSc2ccc(Cl)cc2)n1 | NC1=NC(=CC(=N1)OC)C.ClC1=CC=C(C=C1)S.C=O.C(C)(=O)O>>ClC1=CC=C(C=C1)SCNC1=NC(=CC(=N1)OC)C | O=[CH2:10].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:19]1.[SH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH:9][CH2:10][S:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[n:19]1 | C=O.COc1cc(C)nc(N)n1.Sc1ccc(Cl)cc1 | COc1cc(C)nc(NCSc2ccc(Cl)cc2)n1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 2d0fe4ff000088d00236210328e6740a8e7263313cbd40d392304d162b9c89b9 | 6e2397efe34d7315a5ce483455c7df26531092f417dbaca10e4c007fcfdb0f77 | c1ccc(SCNc2ncccn2)cc1 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[S;H0;D2;+0:8]-[CH2;D2;+0:1]-[NH;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]):[c:11] | null | [] | null | null | null | null | A mixture of 13.99 g of 2-amino-4-methoxy-6-methylpyrimidine (0.1 mole), 14.8 g of 4-chlorothiophenol (0.1 mole), 9.4 g of aqueous 35% formaldehyde (0.11 mole) and 1 g of acetic acid are heated under reflux for 1 hour in 100 ml of methanol. The resultant solution is clarified by filtration, diluted with 150 ml of tolue... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine.Aromatic thiol | Secondary amine.Monosulfide | null | null | c1cncnc1.c1ccccc1 | HO- | CO | null | null | C=O.COc1cc(C)nc(N)n1.Sc1ccc(Cl)cc1>CO>COc1cc(C)nc(NCSc2ccc(Cl)cc2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6791810aca4f480999d23281a8ce7cc3 | C=O.COc1nc(N)nc(N(C)C)n1.Cc1ccc(S(=O)O)cc1>>COc1nc(NCS(=O)(=O)c2ccc(C)cc2)nc(N(C)C)n1 | NC1=NC(=NC(=N1)N(C)C)OC.C1(=CC=C(C=C1)S(=O)O)C.CS(=O)(=O)O.C=O.[Na]>>CN(C1=NC(=NC(=N1)OC)NCS(=O)(=O)C1=CC=C(C=C1)C)C | O=[CH2:7].[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:18][c:19]([N:20]([CH3:21])[CH3:22])[n:23]1.[S:8]([OH:9])(=[O:10])[c:11]1[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][CH2:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[n:18][c:19]([N:20]([CH3:21])[CH3:... | C=O.COc1nc(N)nc(N(C)C)n1.Cc1ccc(S(=O)O)cc1 | COc1nc(NCS(=O)(=O)c2ccc(C)cc2)nc(N(C)C)n1 | null | null | O.CO | Oxidation | OtherReaction | 4c8dd97d415b48657455bb0302975e9329dde32a651672aa651ffaf78b0a7de9 | 52176cde990f5626106e5ae726067cfff0928faa899ed213a94af53862fdf1d0 | O=S(=O)(CNc1ncncn1)c1ccccc1 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:1.[O;D1;H0:9]=[S;H0;D3;+0:10](-[OH;D1;+0:11])-[c:12](:[c:13]):[c:14]>>[O;D1;H0:9]=[S;H0;D4;+0:10](=[O;H0;D1;+0:11])(-[CH2;D2;+0:1]-[NH;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:1)-[c:12](:[c:13]):[c:14] | null | [] | null | null | 30 | MINUTE | 8.5 g (0.05 mole) of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine and 9.1 g (0.05 mole) of toluene-4-sulfinic acid, sodium salt, are suspended in 100 ml of methanol and to the stirred suspension are added, in succession, 4.8 g (0.05 mole) of methanesulfonic acid and 4.7 g (0.055 mole) of aqueous 35% formaldehyde. T... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine.Sulfinic acid | Tosylate.Secondary amine | null | null | c1ncncn1.c1ccccc1 | HO- | O.CO | null | 0.5 | C=O.COc1nc(N)nc(N(C)C)n1.Cc1ccc(S(=O)O)cc1>O.CO>COc1nc(NCS(=O)(=O)c2ccc(C)cc2)nc(N(C)C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9ea8c5f23c574b2e8a2a3b12fa410e55 | C=O.Cc1cc(C)nc(N)n1.Cc1cccc(S(=O)(=O)O)c1>>Cc1ccc(S(=O)(=O)CNc2nc(C)cc(C)n2)cc1 | NC1=NC(=CC(=N1)C)C.CS(=O)(=O)O.C1(=CC(=CC=C1)S(=O)(=O)O)C.[Na].C=O>>CC1=NC(=NC(=C1)C)NCS(=O)(=O)C1=CC=C(C=C1)C | O=[CH2:9].[NH2:10][c:11]1[n:12][c:13]([CH3:14])[cH:15][c:16]([CH3:17])[n:18]1.O[S:6](=[O:7])(=[O:8])[c:19]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[CH2:9][NH:10][c:11]2[n:12][c:13]([CH3:14])[cH:15][c:16]([CH3:17])[n:18]2)[cH:19][cH:20]1 | C=O.Cc1cc(C)nc(N)n1.Cc1cccc(S(=O)(=O)O)c1 | Cc1ccc(S(=O)(=O)CNc2nc(C)cc(C)n2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 7bba7f008d6d215a625995cd0c52299c1a291736daf4b92e547b292fd3935501 | b8d22e398bb2141ed6bf44c041465a74f13a3a3980569b6b5ed75cf915e69b0a | O=S(=O)(CNc1ncccn1)c1ccccc1 | O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1.O=[CH2;D1;+0:10].[NH2;D1;+0:11]-[c:12](:[#7;a:13]:[c:14]):[#7;a:15]:[c:16]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[CH2;D2;+0:10]-[NH;D2;+0:11]-[c:12](:[#7;a:13]:[c:14]):[#7;a:15]:[c:16])-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[... | null | [] | 90 | CELSIUS | 30 | MINUTE | 12.7 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine are suspended in 200 ml of water and then 9.7 g (0.1 mole) of methanesulfonic acid are stirred in to form a solution. To the stirred solution are added, in succession, 18.22 g (0.1 mole) of toluene-3-sulfonic acid, sodium salt, and 9.4 g (0.11 mole) of aqueous 35% for... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine.Sulfonic acid | Tosylate.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1 | HO- | O | 90 | 0.5 | C=O.Cc1cc(C)nc(N)n1.Cc1cccc(S(=O)(=O)O)c1>O>Cc1ccc(S(=O)(=O)CNc2nc(C)cc(C)n2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-78661fbdfa654983baaed09f4ca62550 | C1COCCN1.C=O.Cc1cc(C)nc(N)n1.S=C=S>>Cc1cc(C)nc(NCSC(=S)N2CCOCC2)n1 | [OH-].[K+].N1CCOCC1.C=O.NC1=NC(=CC(=N1)C)C.CS(=O)(=O)O.C(=S)=S>>CC1=NC(=NC(=C1)C)NCSC(=S)N1CCOCC1 | [NH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.O=[CH2:9].[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH2:8])[n:19]1.[S:10]=[C:11]=[S:12]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][CH2:9][S:10][C:11](=[S:12])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[n:19]1 | C1COCCN1.C=O.Cc1cc(C)nc(N)n1.S=C=S | Cc1cc(C)nc(NCSC(=S)N2CCOCC2)n1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 622ede3764689099a2c31b37fbc8717beac4ccad2e490216abada1042cfab33f | 80788209fd0aae246bafc18ed21d4b215eaa8c214878a69f8c868fb82a169d89 | S=C(SCNc1ncccn1)N1CCOCC1 | O=[CH2;D1;+0:1].[#8:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13].[S;D1;H0:14]=[C;H0;D2;+0:15]=[S;H0;D1;+0:16]>>[S;D1;H0:14]=[C;H0;D3;+0:15](-[S;H0;D2;+0:16]-[CH2;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13])-[N;H0;D3;+0:5]1-[C:4]-[C:3]-[#8:2]-[C:7... | null | [] | null | null | null | null | 6.6 g (0.1 mole) of 85% potassium hydroxide and 8.9 g (0.1 mole) of morpholine are dissolved in 200 ml of water and, with cooling, 7.7 g (0.1 mole) of carbon disulfide are added. The mixture is stirred until a yellowish homogeneous solution is obtained. With cooling and stirring, 9.4 g (0.11 mole) of aqueous 35% formal... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine.Secondary amine | Thioamide.Secondary amine.Monosulfide | C1COCCN1 | C1COCC[NH]1 | c1cncnc1.C1COCC[NH]1 | HO- | O | null | null | C1COCCN1.C=O.Cc1cc(C)nc(N)n1.S=C=S>O>Cc1cc(C)nc(NCSC(=S)N2CCOCC2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e6ac12f889244b25b87f4427cb95a90e | C=O.COc1cc(C)nc(N)n1.c1nc[nH]n1>>COc1cc(C)nc(NCn2cncn2)n1 | NC1=NC(=CC(=N1)OC)C.N1N=CN=C1.C=O.C(C)(=O)O>>COC1=NC(=NC(=C1)C)NCN1N=CN=C1 | O=[CH2:10].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:16]1.[nH:11]1[cH:12][n:13][cH:14][n:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH:9][CH2:10][n:11]2[cH:12][n:13][cH:14][n:15]2)[n:16]1 | C=O.COc1cc(C)nc(N)n1.c1nc[nH]n1 | COc1cc(C)nc(NCn2cncn2)n1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 8c84100e28a403468c817276a093b527e625f7bba994cd1da5e6792c1b1cf4c1 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1cnc(NCn2cncn2)nc1 | O=[CH2;D1;+0:1].[#7;a:2]1:[c:3]:[nH;D2;+0:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[c:10]:[#7;a:9]:[c:8](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[n;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[#7;a:2]:[c:3]:1):[#7;a:11]:[c:12] | null | [] | null | null | null | null | With stirring, a mixture of 13.9 g (0.1 mole) of 2-amino-4-methoxy-6-methylpyrimidine, 7 g (0.1 mole) of 1,2,4,-triazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of methanol is refluxed for 11/2 hours. First a clear solution forms, from which the reaction product precipitates in c... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1nc[nH]n1 | c1nc[nH]n1 | c1cncnc1.c1nc[nH]n1 | HO- | CO | null | null | C=O.COc1cc(C)nc(N)n1.c1nc[nH]n1>CO>COc1cc(C)nc(NCn2cncn2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-96190d336abf42e882d1fda197689a7c | C=O.COc1nc(N)nc(N(C)C)n1.c1ccc2[nH]nnc2c1>>COc1nc(NCn2nnc3ccccc32)nc(N(C)C)n1 | NC1=NC(=NC(=N1)N(C)C)OC.N1N=NC2=C1C=CC=C2.C=O.C(C)(=O)O>>N1(N=NC2=C1C=CC=C2)CNC2=NC(=NC(=N2)N(C)C)OC | O=[CH2:7].[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:17][c:18]([N:19]([CH3:20])[CH3:21])[n:22]1.[nH:8]1[n:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][CH2:7][n:8]2[n:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[n:17][c:18]([N:19]([CH3:20])[CH3:21])[n:22]1 | C=O.COc1nc(N)nc(N(C)C)n1.c1ccc2[nH]nnc2c1 | COc1nc(NCn2nnc3ccccc32)nc(N(C)C)n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 964b08c92ca6a1eb522d1beec780c5667fd2506de546d8bb86662dc90843a206 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc2c(c1)nnn2CNc1ncncn1 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:1.[c:9]:[c:10]1:[#7;a:11]:[#7;a:12]:[nH;D2;+0:13]:[c:14]:1:[c:15]>>[c:9]:[c:10]1:[#7;a:11]:[#7;a:12]:[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[NH;D2;+0:2]-[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:2):[c:14]:1:[c:15] | null | [] | null | null | null | null | With stirring, a mixture of 16.9 g (0.1 mole) of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine, 12 g (0.1 mole) of benztriazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of ethanol is heated under reflux for 2 hours. The still hot solution is clarified by filtration and crystals... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1ccc2[nH]nnc2c1 | c1ccc2[nH]nnc2c1 | c1ncncn1.c1ccc2[nH]nnc2c1 | HO- | C(C)O | null | null | C=O.COc1nc(N)nc(N(C)C)n1.c1ccc2[nH]nnc2c1>C(C)O>COc1nc(NCn2nnc3ccccc32)nc(N(C)C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9db9650dad6b4080bfc625b5cf3e8620 | Cc1cc(C)nc(NCn2cncn2)n1.O=C=NS(=O)(=O)c1ccccc1Cl>>Cc1cc(C)nc(N(Cn2cncn2)C(=O)NS(=O)(=O)c2ccccc2Cl)n1 | N1(N=CN=C1)CNC1=NC(=CC(=N1)C)C.ClC1=C(C=CC=C1)S(=O)(=O)N=C=O>>ClC1=C(C=CC=C1)S(=O)(=O)NC(=O)N(C1=NC(=CC(=N1)C)C)CN1N=CN=C1 | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][CH2:9][n:10]2[cH:11][n:12][cH:13][n:14]2)[n:28]1.[C:15](=[O:16])=[N:17][S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[Cl:27]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([N:8]([CH2:9][n:10]2[cH:11][n:12][cH:13][n:14]2)[C:15](=[O:16])[NH:17][S:18](=[... | Cc1cc(C)nc(NCn2cncn2)n1.O=C=NS(=O)(=O)c1ccccc1Cl | Cc1cc(C)nc(N(Cn2cncn2)C(=O)NS(=O)(=O)c2ccccc2Cl)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and secondary amine | 80efce6ceeace49536a85672860e2a5e31d8b9c94341eecb2be7c2c049271cea | c54c1ed6f5693fe7284d99bae8ce6ef1af2bc669c2b604d5d1041c83f556df82 | O=C(NS(=O)(=O)c1ccccc1)N(Cn1cncn1)c1ncccn1 | [#7;a:1]-[C:2]-[NH;D2;+0:3]-[c:4](:[#7;a:5]:[c:6]):[#7;a:7]:[c:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[#16:12](=[O;D1;H0:13])(=[O;D1;H0:14])-[c:15]>>[#7;a:1]-[C:2]-[N;H0;D3;+0:3](-[C;H0;D3;+0:10](=[O;D1;H0:9])-[NH;D2;+0:11]-[#16:12](=[O;D1;H0:13])(=[O;D1;H0:14])-[c:15])-[c:4](:[#7;a:5]:[c:6]):[#7;a:7]:[c:8] | 62.4 | [{"value": 62.0, "product": "ClC1=C(C=CC=C1)S(=O)(=O)NC(=O)N(C1=NC(=CC(=N1)C)C)CN1N=CN=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.4, "product": "ClC1=C(C=CC=C1)S(=O)(=O)NC(=O)N(C1=NC(=CC(=N1)C)C)CN1N=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 4 g (0.019 mole) of 2-(1,2,4-triazol-1-ylmethylamino)-4,6-dimethylpyrimidine are suspended in 100 ml of absolute acetonitrile and then 4.3 g (0.019 mole) of 2-chlorophenylsulfonylisocyanate are stirred into the suspension. The batch is stirred for 24 hours at room temperature and the resultant solution is finally conce... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Sulfonamide.Urea | null | null | c1cncnc1.c1nc[nH]n1.c1ccccc1 | null | C(C)#N | null | 24 | Cc1cc(C)nc(NCn2cncn2)n1.O=C=NS(=O)(=O)c1ccccc1Cl>C(C)#N>Cc1cc(C)nc(N(Cn2cncn2)C(=O)NS(=O)(=O)c2ccccc2Cl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ed5ce096de33477dad5a1554e18687b9 | CC(C)(C)NS(=O)(=O)c1ccccc1C=C1CCOC1=O>>NS(=O)(=O)c1ccccc1C=C1CCOC1=O | CC(C)(C)NS(=O)(=O)C1=C(C=CC=C1)C=C1C(OCC1)=O>>O=C1OCCC1=CC1=C(C=CC=C1)S(=O)(=O)N | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[C:12]1[CH2:13][CH2:14][O:15][C:16]1=[O:17]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[C:12]1[CH2:13][CH2:14][O:15][C:16]1=[O:17] | CC(C)(C)NS(=O)(=O)c1ccccc1C=C1CCOC1=O | NS(=O)(=O)c1ccccc1C=C1CCOC1=O | null | null | FC(C(=O)O)(F)F | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C1OCCC1=Cc1ccccc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 88.8 | [{"value": 88.0, "product": "O=C1OCCC1=CC1=C(C=CC=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "O=C1OCCC1=CC1=C(C=CC=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5.0 g (0.016 mol) of the product of Example 2 in 70 mL trifluoroacetic acid was stirred at room temperature overnight and was then evaporated to yield 3.6 g (88%) of the title compound: m.p. 178°-180°; IR (nujol) 3330, 3230, 3220, 1720, 1640, 1340, 1160 cm-1 ; NMR (DMSO-d6, 200 MHz) δ 3.12 (2H, m), 4.36 (... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.C1CCOC1 | Other | FC(C(=O)O)(F)F | null | null | CC(C)(C)NS(=O)(=O)c1ccccc1C=C1CCOC1=O>FC(C(=O)O)(F)F>NS(=O)(=O)c1ccccc1C=C1CCOC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-248ffe0971b44f2582d70db20b332f12 | COc1cc(OC)nc(NC(=O)Oc2ccccc2)n1.NS(=O)(=O)c1ccccc1C=C1CCOC1=O>>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2C=C2CCOC2=O)n1 | Cl.O=C1OCCC1=CC1=C(C=CC=C1)S(=O)(=O)N.COC1=NC(=NC(=C1)OC)NC(OC1=CC=CC=C1)=O.N12CCCCCC2=NCCC1>>COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C=C1C(OCC1)=O | c1ccc(O[C:11]([NH:10][c:9]2[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:30]2)=[O:12])cc1.[NH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[CH:23]=[C:24]1[CH2:25][CH2:26][O:27][C:28]1=[O:29]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15]... | COc1cc(OC)nc(NC(=O)Oc2ccccc2)n1.NS(=O)(=O)c1ccccc1C=C1CCOC1=O | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2C=C2CCOC2=O)n1 | null | null | C(C)#N.O | Acylation | OtherReaction | 667fe6067474f88ffbad5ef8e75ea479abb1dcdb90207bfe1bf5fbbda20a2b82 | 7357574545fa4eeb65dbf65b1651a3185814d8225c8c3386649f2331a5a0c761 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1C=C1CCOC1=O | [#7;a:1]:[c:2](-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-c1:c:c:c:c:c:1):[#7;a:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[#7;a:1]:[c:2](-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]):[#7;a:6] | 64 | [{"value": 64.0, "product": "COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C=C1C(OCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C=C1C(OCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred suspension of 0.09 g (0.0004 mol) of the product of Example 3 and 0.15 g (0.0005 mol) of (4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester in 1 mL dry acetonitrile under nitrogen was added dropwise 0.08 mL (0.08 g, 0.0005 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carbamic ester.Ether | Sulfonamide.Urea | c1ccccc1 | null | c1cncnc1.c1ccccc1.C1CCOC1 | HO- | C(C)#N.O | null | 0.5 | COc1cc(OC)nc(NC(=O)Oc2ccccc2)n1.NS(=O)(=O)c1ccccc1C=C1CCOC1=O>C(C)#N.O>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2ccccc2C=C2CCOC2=O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ce37ff459f5848f19fc1dbc7eb1ac0e2 | COc1cc(OC)nc(NC(=O)Oc2ccccc2)n1.NS(=O)(=O)c1cccc(Cl)c1C=C1CCOC1=O>>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2cccc(Cl)c2C=C2CCOC2=O)n1 | Cl.ClC=1C(=C(C=CC1)S(=O)(=O)N)C=C1C(OCC1)=O.COC1=NC(=NC(=C1)OC)NC(OC1=CC=CC=C1)=O.N12CCCCCC2=NCCC1>>ClC=1C(=C(C=CC1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC)C=C1C(OCC1)=O | c1ccc(O[C:11]([NH:10][c:9]2[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:31]2)=[O:12])cc1.[NH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][c:21]([Cl:22])[c:23]1[CH:24]=[C:25]1[CH2:26][CH2:27][O:28][C:29]1=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][S:14]... | COc1cc(OC)nc(NC(=O)Oc2ccccc2)n1.NS(=O)(=O)c1cccc(Cl)c1C=C1CCOC1=O | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2cccc(Cl)c2C=C2CCOC2=O)n1 | null | null | C(C)#N.O | Acylation | OtherReaction | 667fe6067474f88ffbad5ef8e75ea479abb1dcdb90207bfe1bf5fbbda20a2b82 | 7357574545fa4eeb65dbf65b1651a3185814d8225c8c3386649f2331a5a0c761 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1C=C1CCOC1=O | [#7;a:1]:[c:2](-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-c1:c:c:c:c:c:1):[#7;a:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[#7;a:1]:[c:2](-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]):[#7;a:6] | 85.3 | [{"value": 83.0, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC)C=C1C(OCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC)C=C1C(OCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred suspension of 0.15 g (0.0005 mol) of the product of Example 7 and 0.21 g (0.0008 mol) of (4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester in 1 mL dry acetonitrile under nitrogen was added dropwise 0.12 mL (0.12 g, 0.0008 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carbamic ester.Ether | Sulfonamide.Urea | c1ccccc1 | null | c1cncnc1.c1ccccc1.C1CCOC1 | HO- | C(C)#N.O | null | 1 | COc1cc(OC)nc(NC(=O)Oc2ccccc2)n1.NS(=O)(=O)c1cccc(Cl)c1C=C1CCOC1=O>C(C)#N.O>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2cccc(Cl)c2C=C2CCOC2=O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-132d57a3cbc44f74a5722eea269ca6a1 | C1CO1.CN(C)C.CN(C)C.O>>C=O.C[N+](C)(C)CCO | CN(C)C.C1CO1.CN(C)C.O>>OCC[N+](C)(C)C.C=O | [CH2:1]1[O:2][CH2:8]1.[CH3:3][N:4]([CH3:6])[CH3:7].CN(C)[CH3:5].[OH2:9]>>[CH2:1]=[O:2].[CH3:3][N+:4]([CH3:5])([CH3:6])[CH2:7][CH2:8][OH:9] | C1CO1.CN(C)C.CN(C)C.O | C=O.C[N+](C)(C)CCO | null | null | CO | Acylation | OtherReaction | c4cae58d4998d89ea221170ced61c2f4e01f2f1a5c40e1945038df4cf31725ca | d5f253a16a8cbc6a682b244c7c69606dd4698869e69432db144dfe507f28473e | null | C-N(-C)-[CH3;D1;+0:1].[C;D1;H3:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH3;D1;+0:5].[CH2;D2;+0:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1.[OH2;D0;+0:9]>>[C;D1;H3:2]-[N+;H0;D4:3](-[C;D1;H3:4])(-[CH3;D1;+0:1])-[CH2;D2;+0:5]-[CH2;D2;+0:7]-[OH;D1;+0:9].[CH2;D1;+0:6]=[O;H0;D1;+0:8] | null | [] | null | null | null | null | 45% by weight choline base in methanol was prepared by the reaction of ethylene oxide with a methanolic solution of 1:1 trimethylamine/water. The trimethylamine content of the stock solution as prepared was 19 ppm. Sufficient paraformaldehyde to give solutions containing 0.05%, 0.1%, 0.5%, and 1% by weight of paraforma... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amine.Tertiary amine | Formaldehyde.Primary alcohol | C1CO1 | null | null | Other | CO | null | null | C1CO1.CN(C)C.CN(C)C.O>CO>C=O.C[N+](C)(C)CCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-847683fa01a94eecbf93753ed93e77bd | Cc1ccc(O)cc1.OO>>Cc1ccc(O)c(O)c1 | OO.OO.C1=CC(=CC=C1O)C>>CC=1C=C(C(O)=CC1)O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][cH:9]1.O[OH:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([OH:8])[cH:9]1 | Cc1ccc(O)cc1.OO | Cc1ccc(O)c(O)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | ae2c40671d5fdb818f0b6d803c1d8cceca080b6105aceeca1808a097ec52d441 | a2fdf414569b219d462bc05c91ebf31e5426b96645f5c78cb091f50cc92fc345 | c1ccccc1 | O-[OH;D1;+0:1].[O;D1;H1:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H1:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[OH;D1;+0:1]):[c:6]:[c:7] | 65.1 | [{"value": 65.1, "product": "CC=1C=C(C(O)=CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A water-free solution of 3.40 grams of H2O2 (0.1 mole) in 108.1 grams (1.0 mole) of p-cresol was heated to 95° C. and treated with 0.018 gram (0.00015 mole) of SeO2. The temperature increased in connection therewith to 161° C. After 15 minutes there was determined a hydrogen peroxide reaction of 99.4%. At that time the... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O | null | 0.25 | Cc1ccc(O)cc1.OO>O>Cc1ccc(O)c(O)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bf696a9a0941417da664285712a10733 | FC1(F)C(Cl)=C(Cl)C(F)(F)C1(F)F.OC1CCCC1>>FC1(F)C(Cl)=C(OC2CCCC2)C(F)(F)C1(F)F | C1(CCCC1)O.[Na].O1CCCC1.ClC1=C(C(C(C1(F)F)(F)F)(F)F)Cl>>C1(CCCC1)OC1=C(C(C(C1(F)F)(F)F)(F)F)Cl | Cl[C:6]1=[C:4]([Cl:5])[C:2]([F:1])([F:3])[C:16]([F:17])([F:18])[C:13]1([F:14])[F:15].[OH:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>>[F:1][C:2]1([F:3])[C:4]([Cl:5])=[C:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[C:13]([F:14])([F:15])[C:16]1([F:17])[F:18] | FC1(F)C(Cl)=C(Cl)C(F)(F)C1(F)F.OC1CCCC1 | FC1(F)C(Cl)=C(OC2CCCC2)C(F)(F)C1(F)F | null | null | CCOCC | Acylation | Williamson Ether Synthesis | e1886bb86311b4c11f16e746fcfb243de4783d54bc2b43a5210a5ef250fe1061 | 8b2d7ad98b9e5b3aa4ef11010bc628a0a98442b0fea590e26be12d72c542b653 | C1=C(OC2CCCC2)CCC1 | Cl-[C;H0;D3;+0:1]1=[C:2](-[Cl;D1;H0:3])-[C:4]-[C:5]-[C:6]-1(-[F;D1;H0:7])-[F;D1;H0:8].[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[O;H0;D2;+0:11]-[C;H0;D3;+0:1]1=[C:2](-[Cl;D1;H0:3])-[C:4]-[C:5]-[C:6]-1(-[F;D1;H0:7])-[F;D1;H0:8])-[C:12] | 79 | [{"value": 79.0, "product": "C1(CCCC1)OC1=C(C(C(C1(F)F)(F)F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Cyclopentanol (23 g, 0.27 mol) and sodium metal (5.6 g, 0.24 mol) were refluxed with 25 ml dry tetrahydrofuran (THF) overnight. The reaction mixture was diluted with 200 ml of dry ether and then added to 1,2-dichlorohexafluorocyclopentene (49 g, 0.2 mol) in 100 ml of dry ether at room temperature with stirring over 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Secondary alcohol | Ether | C1=CCCC1 | C1=CCCC1 | C1=CCCC1.C1CCCC1 | HCl | CCOCC | null | 0.333333 | FC1(F)C(Cl)=C(Cl)C(F)(F)C1(F)F.OC1CCCC1>CCOCC>FC1(F)C(Cl)=C(OC2CCCC2)C(F)(F)C1(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8a125ea60f50441aa95a30af6dfecf36 | CCCCCCCCCN.O=C1CCC(=O)O1>>CCCCCCCCCNC(=O)CCC(=O)O | C1(CCC(=O)O1)=O.C(CCCCCCCC)N>>C(CCCCCCCC)NC(CCC(=O)O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].[C:11]1(=[O:12])[CH2:13][CH2:14][C:15](=[O:16])[O:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[CH2:13][CH2:14][C:15](=[O:16])[OH:17] | CCCCCCCCCN.O=C1CCC(=O)O1 | CCCCCCCCCNC(=O)CCC(=O)O | null | null | CC(=O)C | Protection | OtherReaction | 058bd4c79f70dc248cff01dbd6bcb24847e7daaca3b07e9cb2eccef1b565fa6e | d83a5fe7c1575bfa4f6a9dc1cf7406e299c5c7ecfc75f13bc6d348857a70653f | null | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10] | 79.7 | [{"value": 79.7, "product": "C(CCCCCCCC)NC(CCC(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of succinic anhydride (25.0 g, 0.25 mol) in 150 mL acetone was added dropwise 35.8 g (0.25 mol) of nonylamine. The addition of the amine required 15 minutes, with the acetone solution reaching reflux before the addition was complete. Five minutes after the end of addition, a precipitate formed and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Carboxylic acid.Secondary amide | C1CCOC1 | null | null | null | CC(=O)C | null | 1 | CCCCCCCCCN.O=C1CCC(=O)O1>CC(=O)C>CCCCCCCCCNC(=O)CCC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dfb6c7d8e04e492d834e68ed06daa65a | CCCCCCCCCNC(=O)CCC(=O)O.OO>>CCCCCCCCCNC(=O)CCC(=O)OO | C(CCCCCCCC)NC(CCC(=O)O)=O.OO>>C(CCCCCCCC)NC(CCC(=O)OO)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[CH2:13][CH2:14][C:15](=[O:16])[OH:17].O[OH:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[CH2:13][CH2:14][C:15](=[O:16])[O:17][OH:18] | CCCCCCCCCNC(=O)CCC(=O)O.OO | CCCCCCCCCNC(=O)CCC(=O)OO | null | null | CS(=O)(=O)O | Miscellaneous | OtherReaction | b226d77ae30ca76c37fc9cde5a987164e66aa37df4d2cd5f82b4f127c5a14a47 | db20d33edf4ed6ad1c56374c48bc4c8c17a482c7135e5fe809b17d99f36da805 | null | O-[OH;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[OH;D1;+0:1] | 89.3 | [{"value": 89.3, "product": "C(CCCCCCCC)NC(CCC(=O)OO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | null | null | A 500 mL beaker was charged with 50.0 g (0.205 mol) of 4-nonylamino-4-oxobutyric acid and 100 mL of 98% methanesulfonic acid. The resulting solution was cooled in an ice bath and, with stirring, 38.8 g of 90% hydrogen peroxide (34.9 g, 1.03 mol of hydrogen peroxide) was added dropwise at a rate such that the temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Peroxide | Peroxide | null | null | null | HO- | CS(=O)(=O)O | -15 | null | CCCCCCCCCNC(=O)CCC(=O)O.OO>CS(=O)(=O)O>CCCCCCCCCNC(=O)CCC(=O)OO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-db3f623b9a90456fae3c2ef1e6893c91 | CCCCCCCCCN.COC(=O)CCCCC(=O)Cl>>CCCCCCCCCNC(=O)CCCCC(=O)O | [OH-].[Na+].C(=O)(OC)CCCCC(=O)Cl.[OH-].[Na+].O.C(CCCCCCCC)N>>C(CCCCCCCC)NC(CCCCC(=O)O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].C[O:19][C:17]([CH2:16][CH2:15][CH2:14][CH2:13][C:11](Cl)=[O:12])=[O:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[OH:19] | CCCCCCCCCN.COC(=O)CCCCC(=O)Cl | CCCCCCCCCNC(=O)CCCCC(=O)O | null | null | CCOCC | Acylation | OtherReaction | ef24946e812c58ec5646342efa5dafd5ed10bf586e98ff0052340ef0daf33e7e | 5dbbcac586755560aba4a2c29e7a14cbdd68815807327d0e3fd0dd155b11b926 | null | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].Cl-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7]-[C:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:8]-[C:7]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:11]-[C:10]-[C:9] | null | [] | null | null | null | null | A two liter beaker fitted with a mechanical stirrer, ice bath, and pH electrode, was charged with 700 mL of water and 89.4 g (0.624 mol) of nonylamine in 200 mL of ether. To this stirred mixture was added dropwise over a 30 minute period a solution of the above 5-carbomethoxyvaleryl chloride in 100 mL of ether. Concurr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | null | HCl | CCOCC | null | null | CCCCCCCCCN.COC(=O)CCCCC(=O)Cl>CCOCC>CCCCCCCCCNC(=O)CCCCC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-48cc3136eead4903b29f1eb676c3acbe | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCCCCCCCC(=O)Cl | C(CCCCCCCCCCCCCCCCC)(=O)O.S(=O)(Cl)Cl>>C(CCCCCCCCCCCCCCCCC)(=O)Cl | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].O=S(Cl)[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[Cl:20] | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCCCCCCCC(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | Stearic acid (25 g) was reacted with thionylchloride (30 g) to form stearoylchloride, which was further reacted with indigo (5.2 g) in pyridine to obtain N,N'-distearoylindigo in per se conventional manners.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | null | null | null | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCCCCCCCC(=O)Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-50543bc6295b422e96997e76c434c439 | C=C(C)C(=O)Cl.OCC(F)(F)C(F)C(F)(F)F>>C=C(C)C(=O)OCC(F)(F)C(F)C(F)(F)F | COC1=CC=C(OC)C=C1.C(C(=C)C)(=O)Cl.FC(CO)(C(C(F)(F)F)F)F>>C(C(=C)C)(=O)OCC(C(C(F)(F)F)F)(F)F | Cl[C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[OH:6][CH2:7][C:8]([F:9])([F:10])[CH:11]([F:12])[C:13]([F:14])([F:15])[F:16]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][C:8]([F:9])([F:10])[CH:11]([F:12])[C:13]([F:14])([F:15])[F:16] | C=C(C)C(=O)Cl.OCC(F)(F)C(F)C(F)(F)F | C=C(C)C(=O)OCC(F)(F)C(F)C(F)(F)F | null | null | null | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5] | null | [] | null | null | null | null | To 12 parts of methacrylic acid chloride were added 60 parts of 2,2,3,4,4,4-hexafluorobutyl alcohol as a reactant and a solvent and 0.1 part of hydroquinone dimethyl ether as a polymerization inhibitor. The mixture was heated at a temperature of 90° to 100° C. for 3 hours. The reaction mixture was distilled to give 15 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | null | HCl | null | null | null | C=C(C)C(=O)Cl.OCC(F)(F)C(F)C(F)(F)F>>C=C(C)C(=O)OCC(F)(F)C(F)C(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a5d60f6518044b008e9086f16febeedf | CCc1c(Cl)cc([N+](=O)[O-])c(O)c1Cl>>CCc1c(Cl)cc(N)c(O)c1Cl.Cl | [N+](=O)([O-])C1=C(C(=C(C(=C1)Cl)CC)Cl)O>>Cl.NC1=C(C(=C(C(=C1)Cl)CC)Cl)O | O=[N+:8]([O-])[c:7]1[cH:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[c:11]([Cl:12])[c:9]1[OH:10]>>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([NH2:8])[c:9]([OH:10])[c:11]1[Cl:12].[ClH:13] | CCc1c(Cl)cc([N+](=O)[O-])c(O)c1Cl | CCc1c(Cl)cc(N)c(O)c1Cl.Cl | null | [Ni] | C(C)(C)O | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 525 ml of isopropyl alcohol, 125 g of the same 2-nitro-4,6-dichloro-5-ethylphenol as described above in (1) and 7.5 g of Raney nickel were placed in 1 liter of autoclave, and then the mixture was stirred until absorbing the theoretical amount of hydrogen gas under 10 kg/cm2 of initial pressure of hydrogen at 50° C. or ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C(C)(C)O | null | null | CCc1c(Cl)cc([N+](=O)[O-])c(O)c1Cl>[Ni].C(C)(C)O>CCc1c(Cl)cc(N)c(O)c1Cl.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-036d8b08607c4f47ab181493a52479ca | COC(=O)Cc1occ(O)c2c3ccccc3nc1-2>>O=C(O)CC1=C2N=c3ccccc3=C2C(=O)CO1 | COC(CC=1OC=C(C=2C1N=C1C=CC=CC21)O)=O>>O=C1COC(=C2N=C3C=CC=CC3=C21)CC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][c:5]1[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]-2[c:15]([OH:16])[cH:17][o:18]1>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]1=[C:6]2[N:7]=[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3=[C:14]2[C:15](=[O:16])[CH2:17][O:18]1 | COC(=O)Cc1occ(O)c2c3ccccc3nc1-2 | O=C(O)CC1=C2N=c3ccccc3=C2C(=O)CO1 | null | [O-2].[O-2].[Mn+4] | null | Reduction | OtherReaction | 46c3591f22021913f3445ab6ce7ff044c9e99ac0449e68592c19e655b73f5c8b | 2ae22b122b56b931fdbae62284a684d6d7c36387d89e3096cc7518e51dc2b69a | O=C1COC=C2N=c3ccccc3=C12 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[c;H0;D3;+0:5]1:[o;H0;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[OH;D1;+0:9]):[c;H0;D3;+0:10]2:[c;H0;D3;+0:11]3:[c:12]:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16]:3:[n;H0;D2;+0:17]:[c;H0;D3;+0:18]:1-2>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C;H0;D3;+0:5]1=[C;H0;D3;+0:18]2-[N;H0;D2;+0:17... | null | [] | null | null | null | null | Oxidation of 4-hydroxypyrano[3,4-b]indole acetic acid methyl ester 15 with manganese dioxide, followed by hydrolysis, afforded 4-oxopyrano[3,4-b]-indole acetic acid 18. When 15 was treated with urea in acidified aqueous tetrahydrofuran, a quantitative conversion to 4-ureidopyrano[3,4-b]indole acetic acid methyl ester 1... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol | Carboxylic acid.Ketone.Ether | c1ccc2c(c1)nc1coccc12 | C1=C2N=c3ccccc3=C2CCO1 | C1=C2N=c3ccccc3=C2CCO1 | Other | [O-2].[O-2].[Mn+4] | null | null | COC(=O)Cc1occ(O)c2c3ccccc3nc1-2>[O-2].[O-2].[Mn+4]>O=C(O)CC1=C2N=c3ccccc3=C2C(=O)CO1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-589aecb4d1ef418abc0ff082e9f786cc | CCOC(=O)C(=O)c1c[nH]c2c(CC)cccc12.NO>>CCOC(=O)C(=NO)c1c[nH]c2c(CC)cccc12 | C(C)(=O)[O-].[Na+].Cl.NO.C(C)OC(C(C1=CNC2=C(C=CC=C12)CC)=O)=O>>C(C)OC(C(C1=CNC2=C(C=CC=C12)CC)=NO)=O | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:9]1[cH:10][nH:11][c:12]2[c:13]([CH2:14][CH3:15])[cH:16][cH:17][cH:18][c:19]12.[NH2:7][OH:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[N:7][OH:8])[c:9]1[cH:10][nH:11][c:12]2[c:13]([CH2:14][CH3:15])[cH:16][cH:17][cH:18][c:19]12 | CCOC(=O)C(=O)c1c[nH]c2c(CC)cccc12.NO | CCOC(=O)C(=NO)c1c[nH]c2c(CC)cccc12 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3b5816f78673484492f1e9027ec8b06843f9965cc3956d1b299528352460e3cb | d9a243f6ba886d56e0d31608707ecf09182055b9e74cac0b23531362bbd3484b | c1ccc2[nH]ccc2c1 | O=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:1.[NH2;D1;+0:11]-[O;D1;H1:12]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[C;H0;D3;+0:1](=[N;H0;D2;+0:11]-[O;D1;H1:12])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 75.7 | [{"value": 75.0, "product": "C(C)OC(C(C1=CNC2=C(C=CC=C12)CC)=NO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "C(C)OC(C(C1=CNC2=C(C=CC=C12)CC)=NO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Solutions of sodium acetate (43.7 g, 0.53 mol) in water (100 mL) and hydroxylamine hydrochloride (37 g, 0.53 mol) in water (100 mL) were added to 7-ethyl-α-oxo-1H-indole-3-acetic acid ethyl ester 4 (17.4 g, 0.07 mol), in ethanol (250 mL) and the mixture was heated at reflux for 12 hours. The ethanol was removed by dist... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ester.Oxime | null | null | c1ccc2[nH]ccc2c1 | HO- | O.C(C)O | null | null | CCOC(=O)C(=O)c1c[nH]c2c(CC)cccc12.NO>O.C(C)O>CCOC(=O)C(=NO)c1c[nH]c2c(CC)cccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bdf81a0e5dcd428ba7545489b8cf51ff | CCOC(=O)C(=NO)c1c[nH]c2c(CC)cccc12>>CCOC(=O)C(N)c1c[nH]c2c(CC)cccc12 | C(C)OC(C(C1=CNC2=C(C=CC=C12)CC)=NO)=O.Cl>>C(C)OC(C(C1=CNC2=C(C=CC=C12)CC)N)=O | O[N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:8]1[cH:9][nH:10][c:11]2[c:12]([CH2:13][CH3:14])[cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH2:7])[c:8]1[cH:9][nH:10][c:11]2[c:12]([CH2:13][CH3:14])[cH:15][cH:16][cH:17][c:18]12 | CCOC(=O)C(=NO)c1c[nH]c2c(CC)cccc12 | CCOC(=O)C(N)c1c[nH]c2c(CC)cccc12 | null | [Pd] | C(C)O | Reduction | OtherReaction | 5ebe1a7876a79df84d3f4f7109df26bec79a6cac71893193e6457f66a461ae8a | ee0cd665e3f8693724283a166fc970d164796173c71ad91aea78c9e71235c1fa | c1ccc2[nH]ccc2c1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:1>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:2](-[NH2;D1;+0:1])-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:1 | null | [] | null | null | 4 | HOUR | To 7-ethyl-α-(hydroxyimino)-1H-indole-3-acetic acid ethyl ester 5 (7.3 g, 0.028 mol) in ethanol (200 mL) was added concentrated HCl (3 mL) a nd 10% Pd/C (1.0 g). The mixture was hydrogenated at 40 p.s.i. for 4 hours at 22° C. The catalyst and the solvent were removed and the residue was dissolved in water. After washin... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Oxime | Ester.Primary amine | null | null | c1ccc2[nH]ccc2c1 | Other | [Pd].C(C)O | null | 4 | CCOC(=O)C(=NO)c1c[nH]c2c(CC)cccc12>[Pd].C(C)O>CCOC(=O)C(N)c1c[nH]c2c(CC)cccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5631154fce2f4da7b70e4f6954297de1 | CCOC(=O)C(N)c1c[nH]c2c(CC)cccc12>>CCc1cccc2c(C(N)CO)c[nH]c12 | C(C)OC(C(C1=CNC2=C(C=CC=C12)CC)N)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>NC(CO)C1=CNC2=C(C=CC=C12)CC | CCO[C:11]([CH:9]([c:8]1[c:7]2[cH:6][cH:5][cH:4][c:3]([CH2:2][CH3:1])[c:15]2[nH:14][cH:13]1)[NH2:10])=[O:12]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([NH2:10])[CH2:11][OH:12])[cH:13][nH:14][c:15]12 | CCOC(=O)C(N)c1c[nH]c2c(CC)cccc12 | CCc1cccc2c(C(N)CO)c[nH]c12 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2[nH]ccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[N;D1;H2:4])-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[C:3](-[N;D1;H2:4])-[CH2;D2;+0:1]-[OH;D1;+0:2] | 85.7 | [{"value": 85.7, "product": "NC(CO)C1=CNC2=C(C=CC=C12)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.7, "product": "NC(CO)C1=CNC2=C(C=CC=C12)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | α-Amino-7-ethyl-1H-indole-3-acetic acid ethyl ester 6 (4.9 g, 0.02 mol) in THF (50 mL) was added to LiAlH4 (2.3 g, 0.06 mol) in THF (25 mL) and the mixture was refluxed for 2 hours to give β-amino-7-ethyl-1H-indole-3-ethanol 7 (3.5 g, 85.7%). A sample recrystallized from ethyl acetate-hexane had m.p. 84°-86° C.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2[nH]ccc2c1 | HO- | C1CCOC1 | null | null | CCOC(=O)C(N)c1c[nH]c2c(CC)cccc12>C1CCOC1>CCc1cccc2c(C(N)CO)c[nH]c12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-61de906e5c764fd4a50908f805402d9d | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3NC=O>>CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3N | COC(CC1(OCC(C2=C1NC1=C(C=CC=C21)CC)NC=O)CC)=O>>COC(CC1(OCC(C2=C1NC1=C(C=CC=C21)CC)N)CC)=O | O=C[NH:23][CH:22]1[c:8]2[c:7]3[cH:6][cH:5][cH:4][c:3]([CH2:2][CH3:1])[c:11]3[nH:10][c:9]2[C:12]([CH2:13][CH3:14])([CH2:15][C:16](=[O:17])[O:18][CH3:19])[O:20][CH2:21]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]3[c:9]([nH:10][c:11]12)[C:12]([CH2:13][CH3:14])([CH2:15][C:16](=[O:17])[O:18][CH3:19])[O:20][CH2:21][C... | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3NC=O | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3N | null | null | CO.C | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc2c3c([nH]c2c1)COCC3 | O=C-[NH;D2;+0:1]-[C:2](-[C:3]-[#8:4])-[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]-[C:2](-[NH2;D1;+0:1])-[C:3]-[#8:4] | 50 | [{"value": 50.0, "product": "COC(CC1(OCC(C2=C1NC1=C(C=CC=C21)CC)N)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.9, "product": "COC(CC1(OCC(C2=C1NC1=C(C=CC=C21)CC)N)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,8-Diethyl-4-formylamino-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester 10 (5.5 g, 0.01 mol) in 1N methan olic HCl (4.2 mL) and methanol (18 mL) was stirred at 25° C. for 72 hours, then concentrated in vacuo, diluted with water and extracted with ethyl acetate. The aqueous phase was basified with con... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2c3c([nH]c2c1)COCC3 | Other | CO.C | null | null | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3NC=O>CO.C>CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5676fe6ae17343b787074a067fa5a00b | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3=O>>CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)O)OCC3=O | COC(CC1(OCC(C2=C1NC1=C(C=CC=C21)CC)=O)CC)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C)C1(OCC(C2=C1NC1=C(C=CC=C21)CC)=O)CC(=O)O | C[O:18][C:16]([CH2:15][C:12]1([CH2:13][CH3:14])[c:9]2[c:8]([c:7]3[cH:6][cH:5][cH:4][c:3]([CH2:2][CH3:1])[c:11]3[nH:10]2)[C:21](=[O:22])[CH2:20][O:19]1)=[O:17]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]3[c:9]([nH:10][c:11]12)[C:12]([CH2:13][CH3:14])([CH2:15][C:16](=[O:17])[OH:18])[O:19][CH2:20][C:21]3=[O:22] | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3=O | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)O)OCC3=O | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1COCc2[nH]c3ccccc3c21 | 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] | 93 | [{"value": 93.0, "product": "C(C)C1(OCC(C2=C1NC1=C(C=CC=C21)CC)=O)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(C)C1(OCC(C2=C1NC1=C(C=CC=C21)CC)=O)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 1,8-Diethyl-1,3,4,9-tetrahydro-4-oxopyrano[3,4-b]indole-1-acetic acid methyl ester 17 (1.5 g, 4.8 mmol) was suspended in 30 mL of MeOH and a solution of K2CO3 (3.5 g) in 30 mL of H2O was added. The mixture was heated to reflux, upon which the solution became homogeneous. After refluxing for 2 hours, the solution was co... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c3c([nH]c2c1)COCC3 | Other | O.CO | null | 8 | CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)OC)OCC3=O>O.CO>CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)O)OCC3=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a52449461f8f4b61888e8d7e221d8387 | C=O.CCC1(CC(=O)OC)OCC(N)c2c1[nH]c1ccccc21>>CCC1(CC(=O)OC)OCC(O)c2c1[nH]c1ccccc21 | COC(CC1(OCC(C2=C1NC1=CC=CC=C21)N)CC)=O.O.C=O>>COC(CC1(OCC(C2=C1NC1=CC=CC=C21)O)CC)=O | C=[O:12].N[CH:11]1[CH2:10][O:9][C:3]([CH2:2][CH3:1])([CH2:4][C:5](=[O:6])[O:7][CH3:8])[c:14]2[c:13]1[c:21]1[c:16]([nH:15]2)[cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][CH2:2][C:3]1([CH2:4][C:5](=[O:6])[O:7][CH3:8])[O:9][CH2:10][CH:11]([OH:12])[c:13]2[c:14]1[nH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]21 | C=O.CCC1(CC(=O)OC)OCC(N)c2c1[nH]c1ccccc21 | CCC1(CC(=O)OC)OCC(O)c2c1[nH]c1ccccc21 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | a61cf887c730d83a5dc90e7e80969da43e9c1cb20f0e7096428d2e48ae452b8b | fc7a06eef0b725456f5d7d585d8f3990139808113f032d36dc88ae53908dc6c8 | c1ccc2c3c([nH]c2c1)COCC3 | C=[O;H0;D1;+0:1].N-[CH;D3;+0:2]1-[C:3]-[#8:4]-[C:5]-[c:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10]:2-1>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[#8:4]-[C:5]-[c:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10]:2-1 | 66.4 | [{"value": 66.4, "product": "COC(CC1(OCC(C2=C1NC1=CC=CC=C21)O)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-amino-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester (6 g, 0.020 mol) in 50 mL THF was added 50 mL of H2O and paraformaldehyde (5 g) and the solution was heated at reflux for 2 hours under nitrogen. It was then cooled, concentrated in vacuo, and diluted with ethyl acetate. T... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary alcohol | c1ccc2c3c([nH]c2c1)COCC3 | c1ccc2c3c([nH]c2c1)COCC3 | c1ccc2c3c([nH]c2c1)COCC3 | Other | C1CCOC1 | null | null | C=O.CCC1(CC(=O)OC)OCC(N)c2c1[nH]c1ccccc21>C1CCOC1>CCC1(CC(=O)OC)OCC(O)c2c1[nH]c1ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3c249d2ea45e4d7eb9c39839b84aa498 | CCC1(CC(=O)OC)OCC(O)c2c1[nH]c1ccccc21.[Br][Mg][CH2]c1ccccc1>>CCC1(CC(=O)OC)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21 | COC(CC1(OCC(C2=C1NC1=CC=CC=C21)O)CC)=O.C(C1=CC=CC=C1)[Mg]Br>>COC(CC1(OCC(C2=C1NC1=CC=CC=C21)CC2=CC=CC=C2)CC)=O | O[CH:11]1[CH2:10][O:9][C:3]([CH2:2][CH3:1])([CH2:4][C:5](=[O:6])[O:7][CH3:8])[c:20]2[c:19]1[c:27]1[c:22]([nH:21]2)[cH:23][cH:24][cH:25][cH:26]1.[Br][Mg][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][C:3]1([CH2:4][C:5](=[O:6])[O:7][CH3:8])[O:9][CH2:10][CH:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:... | CCC1(CC(=O)OC)OCC(O)c2c1[nH]c1ccccc21.[Br][Mg][CH2]c1ccccc1 | CCC1(CC(=O)OC)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21 | null | Cl[Ti](Cl)(Cl)Cl | CCOCC.C(Cl)Cl | C-C Coupling | OtherReaction | 55904116283037b89c67502d0ac999187ea061c8887574f4269605b8ffb73765 | e5f803b5eba1fcad9c7b7e86e1e67a2a3eda9454e1436fa466e9dc7992ab4bdf | c1ccc(CC2COCc3[nH]c4ccccc4c32)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#8:3]-[C:4]-[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-1.[Br]-[Mg]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[CH2;D2;+0:10]-[CH;D3;+0:1]1-[C:2]-[#8:3]-[C:4]-[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-1):[c:13] | 51.5 | [{"value": 51.5, "product": "COC(CC1(OCC(C2=C1NC1=CC=CC=C21)CC2=CC=CC=C2)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | To a solution of 1-ethyl-4-hydroxy-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester (1 g, 3.6 mmol) in 60 mL of dry methylene chloride at -78° C. under nitrogen was added TiCl4 in one portion and then after ~10 minutes, a solution of benzyl magnesium bromide in ether was added in one portion and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Secondary alcohol | null | c1ccc2c3c([nH]c2c1)COCC3 | c1ccc2c3c([nH]c2c1)COCC3 | c1ccccc1.c1ccc2c3c([nH]c2c1)COCC3 | HBr.Mg | Cl[Ti](Cl)(Cl)Cl.CCOCC.C(Cl)Cl | -78 | null | CCC1(CC(=O)OC)OCC(O)c2c1[nH]c1ccccc21.[Br][Mg][CH2]c1ccccc1>Cl[Ti](Cl)(Cl)Cl.CCOCC.C(Cl)Cl>CCC1(CC(=O)OC)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9556cefffb024358a20dc4af2da2b613 | CCC1(CC(=O)OC)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21>>CCC1(CC(=O)O)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21 | COC(CC1(OCC(C2=C1NC1=CC=CC=C21)CC2=CC=CC=C2)CC)=O.[OH-].[Na+]>>C(C1=CC=CC=C1)C1COC(C=2NC3=CC=CC=C3C21)(CC(=O)O)CC | C[O:7][C:5]([CH2:4][C:3]1([CH2:2][CH3:1])[O:8][CH2:9][CH:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[c:19]1[nH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]21)=[O:6]>>[CH3:1][CH2:2][C:3]1([CH2:4][C:5](=[O:6])[OH:7])[O:8][CH2:9][CH:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[c:19]1... | CCC1(CC(=O)OC)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21 | CCC1(CC(=O)O)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21 | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CC2COCc3[nH]c4ccccc4c32)cc1 | 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] | 82 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)C1COC(C=2NC3=CC=CC=C3C21)(CC(=O)O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "C(C1=CC=CC=C1)C1COC(C=2NC3=CC=CC=C3C21)(CC(=O)O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-benzyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester (0.67 g, 1.8 mmol) in 30 mL of ethanol was added 30 mL of 10% solution of sodium hydroxide and heated at reflux for 2 hours under nitrogen. The reaction mixture was then cooled and concentrated in vacuo, diluted with 20 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c3c([nH]c2c1)COCC3 | Other | C(C)O | null | null | CCC1(CC(=O)OC)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21>C(C)O>CCC1(CC(=O)O)OCC(Cc2ccccc2)c2c1[nH]c1ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-01fa6ac283af4ba48f163633f0be11dd | CCOC(=O)c1ncc[nH]1.O=[N+]([O-])c1ccccc1CCl>>CCOC(=O)c1nccn1Cc1ccccc1[N+](=O)[O-] | N1C(=NC=C1)C(=O)OCC.[N+](=O)([O-])C1=C(CCl)C=CC=C1.C([O-])([O-])=O.[K+].[K+]>>[N+](=O)([O-])C1=C(CN2C(=NC=C2)C(=O)OCC)C=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][cH:9][nH:10]1.Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][cH:9][n:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CCOC(=O)c1ncc[nH]1.O=[N+]([O-])c1ccccc1CCl | CCOC(=O)c1nccn1Cc1ccccc1[N+](=O)[O-] | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5118ce9eea46859cccf16d01cf8151757afd816de0c93fe6fcb74a0ee15c5a67 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccnc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[n;H0;D3;+0:13]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 85.4 | [{"value": 85.4, "product": "[N+](=O)([O-])C1=C(CN2C(=NC=C2)C(=O)OCC)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.4, "product": "[N+](=O)([O-])C1=C(CN2C(=NC=C2)C(=O)OCC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 14 g (0.1 mol) of ethyl imidazol-2-carboxylate, 18.9 g (0.11 mol) of o-nitrobenzyl chloride, 13.8 g (0.1 mol) of anhydrous potassium carbonate and 100 ml of dimethylformamide was heated at 100° C. for 2 hours while stirring. Then, the solvent was substantially distilled off in vacuo, the residue was mixed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1 | HCl | CN(C=O)C | 100 | null | CCOC(=O)c1ncc[nH]1.O=[N+]([O-])c1ccccc1CCl>CN(C=O)C>CCOC(=O)c1nccn1Cc1ccccc1[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1127223cbea3488e85342ef665537ecd | CCOC(=O)c1nccn1Cc1ccccc1[N+](=O)[O-]>>CCOC(=O)c1nccn1Cc1ccccc1N | [N+](=O)([O-])C1=C(CN2C(=NC=C2)C(=O)OCC)C=CC=C1>>NC1=C(CN2C(=NC=C2)C(=O)OCC)C=CC=C1 | O=[N+:18]([O-])[c:17]1[c:12]([CH2:11][n:10]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:7][cH:8][cH:9]2)[cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][cH:9][n:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[NH2:18] | CCOC(=O)c1nccn1Cc1ccccc1[N+](=O)[O-] | CCOC(=O)c1nccn1Cc1ccccc1N | null | [Ni] | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Cn2ccnc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 85.4 | [{"value": 85.4, "product": "NC1=C(CN2C(=NC=C2)C(=O)OCC)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.4, "product": "NC1=C(CN2C(=NC=C2)C(=O)OCC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 49.6 g (0.18 mol) of ethyl 1-(2-nitrobenzyl)-imidazole-2-carboxylate were hydrogenated in 500 ml of tetrahydrofuran at room temperature under a pressure of 5 bar in the presence of Raney nickel. After the theoretical quantity of hydrogen had been absorbed, the catalyst was suction-filtered off, and the filtrate was eva... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ncc[nH]1.c1ccccc1 | Other | [Ni].O1CCCC1 | null | null | CCOC(=O)c1nccn1Cc1ccccc1[N+](=O)[O-]>[Ni].O1CCCC1>CCOC(=O)c1nccn1Cc1ccccc1N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-938dad52bf424847b5a87b0af4a64a9c | CCCCCCCCCCCCCCCCCCN.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O | C(CCCCCCCCCCCCCCCCC)N.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>C(CCCCCCCCCCCCCCCCC)NC1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].O=[CH:20][C@H:22]([OH:21])[C@@H:25]([OH:26])[C@H:27]([OH:28])[C@@H:29]([CH2:23][OH:24])[OH:30]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][... | CCCCCCCCCCCCCCCCCCN.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 700d99fb45e8c08897a966fba4f347880bc47ef6e630efe8f099c330952bc13f | 7b4a51bec8d1f2dbd10dc44a9694073db624a60f2ad010a97db84ae5bad43264 | C1CCOCC1 | O=[CH;D2;+0:1]-[C@H;D3;+0:2](-[OH;D1;+0:3])-[C:4](-[O;D1;H1:5])-[C:6](-[O;D1;H1:7])-[C@H;D3;+0:8](-[O;D1;H1:9])-[CH2;D2;+0:10]-[O;D1;H1:11].[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[CH;D3;+0:1]1-[O;H0;D2;+0:3]-[C@H;D3;+0:2](-[CH2;D2;+0:10]-[O;D1;H1:11])-[C:4](-[O;D1;H1:5])-[C:6](-[O;D1;H1:7])-[C@H;D3;+... | null | [] | 70 | CELSIUS | 15 | MINUTE | 20 g of octadecylamine are dissolved in 120 ml of ethanol and the solution is warmed to 70° C. 11 g of anhydrous D-glucose are added. After a clear solution has formed, stirring is continued at 70° C. for a further 15 minutes. The solution is cooled to 10° C. and left to stand for 15 minutes. The crystal sludge formed ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Secondary alcohol.Secondary alcohol.Primary amine | Ether.Primary alcohol.Secondary alcohol.Secondary amine | null | C1CCOCC1 | C1CCOCC1 | HO- | C(C)O | 70 | 0.25 | CCCCCCCCCCCCCCCCCCN.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>C(C)O>CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e81b667d9aad48d78623dcbfce1d50b3 | CCCCCCCCCCCCN.O=C[C@@H](O)[C@@H](O)[C@H](O)CO>>CCCCCCCCCCCCN(C(=O)CCCCCCCCCCC)C1OC[C@@H](O)[C@H](O)[C@@H]1O | O=C[C@@H](O)[C@@H](O)[C@H](O)CO.O.C(CCCCCCCCCCC)N>>C1([C@@H](O)[C@@H](O)[C@H](O)CO1)N(C(CCCCCCCCCCC)=O)CCCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].[CH:14](=[O:15])[C@H:16]([C@H:17]([C@@H:18]([CH2:29][OH:28])[OH:33])[OH:35])[OH:31]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:14](=[O:15])[CH2:16][CH2:17][CH2:18][CH2:1... | CCCCCCCCCCCCN.O=C[C@@H](O)[C@@H](O)[C@H](O)CO | CCCCCCCCCCCCN(C(=O)CCCCCCCCCCC)C1OC[C@@H](O)[C@H](O)[C@@H]1O | null | null | C(C)(C)O | Acylation | OtherReaction | bd12222f5a1dbc90ca4ad198aa569e19fc1d179bf399e9bbb35041bb97e6d0ae | 9f2b424da96061e4cbc2dc7b3a873dbb8a3ff62181cbd30d1d5a49c911995492 | C1CCOCC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[CH;D2;+0:5]-[C@@H;D3;+0:6](-[OH;D1;+0:7])-[C@@H;D3;+0:8](-[OH;D1;+0:9])-[C@H;D3;+0:10](-[OH;D1;+0:11])-[CH2;D2;+0:12]-[OH;D1;+0:13]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C:14]1-[O;H0;D2;+0:13]-[CH2;D2;+0:12]-[C:15](-[OH;D1;+0:7])-[C:16](-[OH;D1;+0:11])-[C:17]-1-[OH;D1;+0:9])-[C;H0;D3;+0:5... | null | [] | null | null | null | null | 10 g of D-lyxose are dissolved in 120 ml of isopropanol and 60 ml of water and the solution is warmed to 70° C. 18 g of dodecylamine are added. After a clear solution has formed, the temperature is maintained for a further 15 minutes. The mixture is cooled to room temperature and evaporated in vacuo. 10 g of the result... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Primary amine | Ether.Tertiary amide.Secondary alcohol.Secondary alcohol.Secondary alcohol | null | C1CCOCC1 | C1CCOCC1 | Other | C(C)(C)O | null | null | CCCCCCCCCCCCN.O=C[C@@H](O)[C@@H](O)[C@H](O)CO>C(C)(C)O>CCCCCCCCCCCCN(C(=O)CCCCCCCCCCC)C1OC[C@@H](O)[C@H](O)[C@@H]1O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c0f934309e2b409e80e6ac307eb62b54 | CC12OC1C(=O)c1ccccc1C2=O>>CC1=CC(=O)c2ccccc2C1=O | O1C2(C(C3=CC=CC=C3C(C21)=O)=O)C>>CC1=CC(C2=CC=CC=C2C1=O)=O | O1[C:2]2([CH3:1])[CH:3]1[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[C:12]2=[O:13]>>[CH3:1][C:2]1=[CH:3][C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]1=[O:13] | CC12OC1C(=O)c1ccccc1C2=O | CC1=CC(=O)c2ccccc2C1=O | null | null | C(C)O | Miscellaneous | OtherReaction | d9329f4b756907c222746c94c6a03d3126b49c1318996b5c6b83c4aa3a1d40af | 4332fe0ec601bde18c21b5783b9089cdaa378b1cc06a7c680f8caa518ecaad9e | O=C1C=CC(=O)c2ccccc21 | [C;D1;H3:1]-[C;H0;D4;+0:2]12-O-[CH;D3;+0:3]-1-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-[C:8]-2=[O;D1;H0:9]>>[C;D1;H3:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-[C:8]-1=[O;D1;H0:9] | null | [] | null | null | null | null | According to Flowchart V, 2,3-epoxy-2-methyl-1,4-naphthoquinone 11 is reacted with an amine 2, where R2, R3, R4 and R5 are as described above, in absolute ethanol with heat for several hours, producing the 3-methyl-1,4-naphthalenedione derivatives 12.
Conditions: See reaction.notes.procedure_details.
Workup: with heat ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether | Ketone.Ketone | c1ccc2c(c1)CC1OC1C2 | C1=CCc2ccccc2C1 | C1=CCc2ccccc2C1 | Other | C(C)O | null | null | CC12OC1C(=O)c1ccccc1C2=O>C(C)O>CC1=CC(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5e5ab1b93bec4eba8877cca84ee8b3fb | CCOC(=O)N1CCNCC1.O=C1C(Cl)=C(Cl)C(=O)c2ccccc21>>CCOC(=O)N1CCN(C2=C(Cl)C(=O)c3ccccc3C2=O)CC1 | ClC=1C(C2=CC=CC=C2C(C1Cl)=O)=O.N1(CCNCC1)C(=O)OCC>>ClC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][NH:9][CH2:23][CH2:24]1.Cl[C:10]1=[C:11]([Cl:12])[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10]2=[C:11]([Cl:12])[C:13](=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[C:21]2=... | CCOC(=O)N1CCNCC1.O=C1C(Cl)=C(Cl)C(=O)c2ccccc21 | CCOC(=O)N1CCN(C2=C(Cl)C(=O)c3ccccc3C2=O)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0912e26e7d1eb0222158d18478bb8682658ea8b99a047d9cfd5ddf1ce0ba8013 | 933b337e66ad3bf71c4790533c0d1ebcae3a16ae4bb9f3b59c4a11d8d3c64228 | O=C1C=C(N2CCNCC2)C(=O)c2ccccc21 | Cl-[C;H0;D3;+0:1]1=[C:2](-[Cl;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-[C:8]-1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[Cl;D1;H0:3]-[C:2]1=[C;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2)-[C:8](=[O;D1;H0:9])-[c:7]:[c:6]-[C:4]-1=[O;D1;H0:5] | 45.9 | [{"value": 45.9, "product": "ClC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 11.35 g of 2,3-dichloro-1,4-naphthoquinone, 15.8 g of 1-piperazinecarboxylic acid, ethyl ester and 400 ml of absolute ethanol was heated at reflux for 3 hours and then evaporated to dryness. The residue was taken up in 300 ml of dichloromethane and filtered through silica gel. The filtrate was evaporated a... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Secondary amine | Enamine | C1C[NH]CCN1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | HCl | C(C)O | null | null | CCOC(=O)N1CCNCC1.O=C1C(Cl)=C(Cl)C(=O)c2ccccc21>C(C)O>CCOC(=O)N1CCN(C2=C(Cl)C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1eafa52968e943938f9fb0c465258a6f | CNCCN(C)Cc1ccccc1.O=C1C(Cl)=C(Cl)C(=O)c2ccccc21>>CN(CCN(C)C1=C(Cl)C(=O)c2ccccc2C1=O)Cc1ccccc1.Cl | CNCCN(CC1=CC=CC=C1)C.ClC=1C(C2=CC=CC=C2C(C1Cl)=O)=O>>Cl.ClC=1C(C2=CC=CC=C2C(C1N(CCN(CC1=CC=CC=C1)C)C)=O)=O | [CH3:1][N:2]([CH2:3][CH2:4][NH:5][CH3:6])[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[C:7]1([Cl:27])=[C:8]([Cl:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][N:2]([CH2:3][CH2:4][N:5]([CH3:6])[C:7]1=[C:8]([Cl:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]1... | CNCCN(C)Cc1ccccc1.O=C1C(Cl)=C(Cl)C(=O)c2ccccc21 | CN(CCN(C)C1=C(Cl)C(=O)c2ccccc2C1=O)Cc1ccccc1.Cl | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6f37a459d2fb11a17a9e97f5cd042e976fec1a8ec93175c8f9dea954d9e1125b | d366d1b6aa9b6e9510093ba8fd2f2edd66587096816415e691b2ed113a22fc6c | O=C1C=C(NCCNCc2ccccc2)C(=O)c2ccccc21 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[Cl;D1;H0:5]-[C:6]1=[C;H0;D3;+0:7](-[Cl;H0;D1;+0:8])-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-[C:13]-1=[O;D1;H0:14]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[C;H0;D3;+0:7]1=[C:6](-[Cl;D1;H0:5])-[C:13](=[O;D1;H0:14])-[c:12]:[c:11]-[C:9]-1=[O;D1;H0:10].[ClH;D0;+0:8] | null | [] | -10 | CELSIUS | 16 | HOUR | A 4.5 g portion of methyl 2-[methyl(phenylmethyl)amino]ethylamine was added to a stirred slurry of 5.6 g of 2,3-dichloro-1,4-naphthoquinone in 150 ml of absolute ethanol. Stirring was continued for 16 hours, then the mixture was heated at reflux for one hour and filtered while hot. The mixture was then cooled at -10° C... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Secondary amine | Enamine.Ketone | C1=CCc2ccccc2C1 | C1=CCc2ccccc2C1 | C1=CCc2ccccc2C1.c1ccccc1 | null | C(C)O | -10 | 16 | CNCCN(C)Cc1ccccc1.O=C1C(Cl)=C(Cl)C(=O)c2ccccc21>C(C)O>CN(CCN(C)C1=C(Cl)C(=O)c2ccccc2C1=O)Cc1ccccc1.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bbb9c2f74808455388a035da8c8a3eeb | CC(=O)NC1=C(Cl)C(=O)c2ccccc2C1=O.c1ccc(CN2CCNCC2)cc1>>CC(=O)NC1=C(N2CCN(Cc3ccccc3)CC2)C(=O)c2ccccc2C1=O | C(C)(=O)NC=1C(C2=CC=CC=C2C(C1Cl)=O)=O.C(C1=CC=CC=C1)N1CCNCC1>>O=C1C(=C(C(C2=CC=CC=C12)=O)N1CCN(CC1)CC1=CC=CC=C1)NC(C)=O | Cl[C:6]1=[C:5]([NH:4][C:2]([CH3:1])=[O:3])[C:28](=[O:29])[c:27]2[c:22]([cH:23][cH:24][cH:25][cH:26]2)[C:20]1=[O:21].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>>[CH3:1][C:2](=[O:3])[NH:4][C:5]1=[C:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH... | CC(=O)NC1=C(Cl)C(=O)c2ccccc2C1=O.c1ccc(CN2CCNCC2)cc1 | CC(=O)NC1=C(N2CCN(Cc3ccccc3)CC2)C(=O)c2ccccc2C1=O | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | d4a0d8c63c5bbf8e6b2a19dd3b1761c1fda17365ba7c27585f8e97bb31c6dca1 | 2f1af1bc2b6a104816ee6e304bb76145e9e36ef858bc716179b7b9df9c8858ef | O=C1C=C(N2CCN(Cc3ccccc3)CC2)C(=O)c2ccccc21 | Cl-[C;H0;D3;+0:1]1=[C:2](-[#7:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-[C:11]-1=[O;D1;H0:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[C;D1;H3:5]-[C:4](=[O;D1;H0:6])-[#7:3]-[C:2]1=[C;H0;D3;+0:1](-[N;H0;D3;+0:16]2-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-2)-[C:11](=[O;D1;H0:12])-[c:10... | 89.7 | [{"value": 89.7, "product": "O=C1C(=C(C(C2=CC=CC=C12)=O)N1CCN(CC1)CC1=CC=CC=C1)NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 500 mg of 2-acetylamino-3-chloro-1,4-naphthoquinone, 880 mg of N-benzylpiperazine and 40 ml of absolute ethanol was heated at reflux for 3 hours, then the solvent was removed. The remainder was passed through a small plug of silica gel and eluted with chloroform. The eluate was concentrated to a solid whic... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Alkenyl halide.Ketone.Secondary amine | Enamine.Enamine | C1=CCc2ccccc2C1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.c1ccccc1.C1=CCc2ccccc2C1 | HCl | C(C)O | null | null | CC(=O)NC1=C(Cl)C(=O)c2ccccc2C1=O.c1ccc(CN2CCNCC2)cc1>C(C)O>CC(=O)NC1=C(N2CCN(Cc3ccccc3)CC2)C(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-da7582724371467fa51419dee56b16ee | CCCCOC(=O)Cl.O=C1C(Cl)=C(N2CCNCC2)C(=O)c2ccccc21>>CC(C)COC(=O)N1CCN(C2=C(Cl)C(=O)c3ccccc3C2=O)CC1 | ClC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCNCC1.ClC(=O)OCCCC.O1CCCC1.O1CCCC1>>ClC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C(=O)OCC(C)C | Cl[C:6]([O:5][CH2:4][CH2:2][CH2:1][CH3:3])=[O:7].[NH:8]1[CH2:9][CH2:10][N:11]([C:12]2=[C:13]([Cl:14])[C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C:23]2=[O:24])[CH2:25][CH2:26]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12]2=[C:13]([Cl:14])[C:15](=[O:16])[c:17]3[cH:18][... | CCCCOC(=O)Cl.O=C1C(Cl)=C(N2CCNCC2)C(=O)c2ccccc21 | CC(C)COC(=O)N1CCN(C2=C(Cl)C(=O)c3ccccc3C2=O)CC1 | null | null | null | C-C Coupling | OtherReaction | 09de75b17c7eee1289e3b190226d6ad52495b2ae0a16b9cd4889f920cc52f2c2 | af3aa3e2f147b2df60916d28a16c97cabb605429e921245c8b8e12ed2ec35188 | O=C1C=C(N2CCNCC2)C(=O)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[CH3;D1;+0:6]-[CH;D3;+0:5](-[CH3;D1;+0:7])-[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1 | null | [] | null | null | 20 | MINUTE | A solution of 830 mg of 3-chloro-2-piperazinyl-1,4-naphthoquinone in 50 ml of tetrahydrofuran was added dropwise to a solution of 0.39 ml of butyl chloroformate in 10 ml of tetrahydrofuran. This mixture was stirred for 20 minutes, then filtered and the filtrate concentrated to an oil. The oil was recrystallized from et... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester.Ether | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | HCl | null | null | 0.333333 | CCCCOC(=O)Cl.O=C1C(Cl)=C(N2CCNCC2)C(=O)c2ccccc21>>CC(C)COC(=O)N1CCN(C2=C(Cl)C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bd93f5c31e3a4d1182f4de13828044bc | CC12OC1C(=O)c1ccccc1C2=O.CCOC(=O)N1CCNCC1>>CCOC(=O)N1CCN(C2=C(C)C(=O)c3ccccc3C2=O)CC1 | O1C2C(C3=CC=CC=C3C(C21C)=O)=O.N1(CCNCC1)C(=O)OCC>>CC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C(=O)OCC | O1[CH:10]2[C:11]1([CH3:12])[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[C:21]2=[O:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][NH:9][CH2:23][CH2:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10]2=[C:11]([CH3:12])[C:13](=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[C:21... | CC12OC1C(=O)c1ccccc1C2=O.CCOC(=O)N1CCNCC1 | CCOC(=O)N1CCN(C2=C(C)C(=O)c3ccccc3C2=O)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c7d49f3b46b25ba8d4f47861ba897f9b2a406154c4f8af99f3731b072bf67e93 | 85d3530ea2ab12eabae6f8a679c30f9a97b0d5a6a810726450a36f9da54ec15c | O=C1C=C(N2CCNCC2)C(=O)c2ccccc21 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[C;D1;H3:7]-[C;H0;D4;+0:8]12-O-[CH;D3;+0:9]-1-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]-[C:14]-2=[O;D1;H0:15]>>[C;D1;H3:7]-[C;H0;D3;+0:8]1=[C;H0;D3;+0:9](-[N;H0;D3;+0:4]2-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-2)-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]-[C:14]-1=[O;D1;H0:15] | 30.5 | [{"value": 30.5, "product": "CC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 12 | HOUR | A mixture of 1.88 g of 2,3-epoxy-3-methyl-1,4-naphthoquinone, 3.16 g of piperazinecarboxylic acid, ethyl ester and 100 ml of absolute ethanol was stirred for 12 hours at 50° C. The solvent was then removed and the remainder filtered through a one inch plug of silica gel and eluted with chloroform. The eluate was evapor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Secondary amine | Enamine | c1ccc2c(c1)CC1OC1C2.C1C[NH]CCN1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | HO- | C(C)O | 50 | 12 | CC12OC1C(=O)c1ccccc1C2=O.CCOC(=O)N1CCNCC1>C(C)O>CCOC(=O)N1CCN(C2=C(C)C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9932b54276624110a863e2acdaabdbe2 | CC1=C(N2CCNCC2)C(=O)c2ccccc2C1=O.O=C=Nc1ccc(Cl)cc1>>CC1=C(N2CCN(C(=O)Nc3ccc(Cl)cc3)CC2)C(=O)c2ccccc2C1=O | CC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCNCC1.ClC1=CC=C(C=C1)N=C=O>>ClC1=CC=C(C=C1)NC(=O)N1CCN(CC1)C=1C(C2=CC=CC=C2C(C1C)=O)=O | [CH3:1][C:2]1=[C:3]([N:4]2[CH2:5][CH2:6][NH:7][CH2:18][CH2:19]2)[C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]1=[O:29].[C:8](=[O:9])=[N:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1>>[CH3:1][C:2]1=[C:3]([N:4]2[CH2:5][CH2:6][N:7]([C:8](=[O:9])[NH:10][c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c... | CC1=C(N2CCNCC2)C(=O)c2ccccc2C1=O.O=C=Nc1ccc(Cl)cc1 | CC1=C(N2CCN(C(=O)Nc3ccc(Cl)cc3)CC2)C(=O)c2ccccc2C1=O | null | null | O1CCCC1 | Acylation | Urea synthesis via isocyanate and secondary amine | 6fdae4b903e981d8b7a376762a2f4ccd0c6fe7e77f0529898c101f9e9062d1aa | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C1C=C(N2CCN(C(=O)Nc3ccccc3)CC2)C(=O)c2ccccc21 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 83.4 | [{"value": 83.4, "product": "ClC1=CC=C(C=C1)NC(=O)N1CCN(CC1)C=1C(C2=CC=CC=C2C(C1C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A solution of 150 mg of 3-methyl-2-piperazinyl-1,4-naphthoquinone in 50 ml of tetrahydrofuran was treated with a solution of 100 mg of 4-chlorophenylisocyanate in 10 ml of tetrahydrofuran. This mixture was stirred 1/2 hour, then evaporated in vacuo and the residue taken up in dichloromethane and filtered. The filtrate ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.C1=CCc2ccccc2C1 | null | O1CCCC1 | null | 0.5 | CC1=C(N2CCNCC2)C(=O)c2ccccc2C1=O.O=C=Nc1ccc(Cl)cc1>O1CCCC1>CC1=C(N2CCN(C(=O)Nc3ccc(Cl)cc3)CC2)C(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e28d3533b1644cf894614640d3f6f843 | O=C1C(Cl)=C(N2CCNCC2)C(=O)c2ccccc21.O=S(=O)(Cl)c1ccccc1C(F)(F)F>>O=C1C(Cl)=C(N2CCN(S(=O)(=O)c3ccccc3C(F)(F)F)CC2)C(=O)c2ccccc21 | ClC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCNCC1.FC(C1=C(C=CC=C1)S(=O)(=O)Cl)(F)F>>ClC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)S(=O)(=O)C1=C(C=CC=C1)C(F)(F)F | [O:1]=[C:2]1[C:3]([Cl:4])=[C:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:23][CH2:24]2)[C:25](=[O:26])[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]21.Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22]>>[O:1]=[C:2]1[C:3]([Cl:4])=[C:5]([N:6]2[CH2:7][CH2:8][N:9]([S:10](=[O:11])(=[O:12])[c:13... | O=C1C(Cl)=C(N2CCNCC2)C(=O)c2ccccc21.O=S(=O)(Cl)c1ccccc1C(F)(F)F | O=C1C(Cl)=C(N2CCN(S(=O)(=O)c3ccccc3C(F)(F)F)CC2)C(=O)c2ccccc21 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C1C=C(N2CCN(S(=O)(=O)c3ccccc3)CC2)C(=O)c2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A 1.5 g portion of 3-chloro-2-piperazinyl-1,4-naphthoquinone and 1.26 g of 2-trifluoromethylbenzenesulfonyl chloride were reacted as described in Example 56, giving 1.53 g of the desired product, mp 122°-124° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.C1=CCc2ccccc2C1 | HCl | null | null | null | O=C1C(Cl)=C(N2CCNCC2)C(=O)c2ccccc21.O=S(=O)(Cl)c1ccccc1C(F)(F)F>>O=C1C(Cl)=C(N2CCN(S(=O)(=O)c3ccccc3C(F)(F)F)CC2)C(=O)c2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-56336ee2ad824b1f9857b1d476eadee3 | CC(=O)N(C(C)=O)C1=C(Cl)C(=O)c2ccccc2C1=O.Fc1ccc(N2CCNCC2)cc1>>CC(=O)N(C(C)=O)C1=C(N2CCN(c3ccc(F)cc3)CC2)C(=O)c2ccccc2C1=O | C(C)(=O)N(C(C)=O)C=1C(C2=CC=CC=C2C(C1Cl)=O)=O.FC1=CC=C(C=C1)N1CCNCC1>>C(C)(=O)N(C(C)=O)C=1C(C2=CC=CC=C2C(C1N1CCN(CC1)C1=CC=C(C=C1)F)=O)=O | Cl[C:9]1=[C:8]([N:4]([C:2]([CH3:1])=[O:3])[C:5]([CH3:6])=[O:7])[C:31](=[O:32])[c:30]2[c:25]([cH:26][cH:27][cH:28][cH:29]2)[C:23]1=[O:24].[NH:10]1[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][C:2](=[O:3])[N:4]([C:5]([CH3:6])=[O:7])[C:8]1=[C:9]([N:10]2[CH2:11][CH2:12... | CC(=O)N(C(C)=O)C1=C(Cl)C(=O)c2ccccc2C1=O.Fc1ccc(N2CCNCC2)cc1 | CC(=O)N(C(C)=O)C1=C(N2CCN(c3ccc(F)cc3)CC2)C(=O)c2ccccc2C1=O | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | d4a0d8c63c5bbf8e6b2a19dd3b1761c1fda17365ba7c27585f8e97bb31c6dca1 | 2f1af1bc2b6a104816ee6e304bb76145e9e36ef858bc716179b7b9df9c8858ef | O=C1C=C(N2CCN(c3ccccc3)CC2)C(=O)c2ccccc21 | Cl-[C;H0;D3;+0:1]1=[C:2](-[#7:3](-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]-[C:14]-1=[O;D1;H0:15].[#7:16]1-[C:17]-[C:18]-[NH;D2;+0:19]-[C:20]-[C:21]-1>>[C;D1;H3:5]-[C:4](=[O;D1;H0:6])-[#7:3](-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[C:2]1=[C;H0;D3;+0:1](-[N;H0;D3;+0:... | null | [] | null | null | null | null | A mixture of 1.66 g of 2-[N,N-diacetylamino]-3-chloro-1,4-naphthoquinone and 1.441 g of 1-(4-fluorophenyl)piperazine in 50 ml of ethanol was refluxed overnight, then evaporated in vacuo. The residue was dissolved in dichloromethane, filtered through silica gel and eluted with chloroform:methanol (100:2). The eluent was... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Alkenyl halide.Ketone.Secondary amine | Enamine.Enamine | C1=CCc2ccccc2C1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.c1ccccc1.C1=CCc2ccccc2C1 | HCl | C(C)O | null | null | CC(=O)N(C(C)=O)C1=C(Cl)C(=O)c2ccccc2C1=O.Fc1ccc(N2CCNCC2)cc1>C(C)O>CC(=O)N(C(C)=O)C1=C(N2CCN(c3ccc(F)cc3)CC2)C(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ce5069d4005549b6a217e8c95207166c | FC(F)(F)c1cccc(N2CCNCC2)c1.O=C1c2ccccc2C(=O)C2OC12>>O=C1C(O)=C(N2CCN(c3cccc(C(F)(F)F)c3)CC2)C(=O)c2ccccc21 | O1C2C(C3=CC=CC=C3C(C21)=O)=O.FC(C=1C=C(C=CC1)N1CCNCC1)(F)F>>OC=1C(C2=CC=CC=C2C(C1N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F)=O)=O | [NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]2)[CH2:20][CH2:21]1.[O:1]=[C:2]1[CH:3]2[O:4][CH:5]2[C:22](=[O:23])[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21>>[O:1]=[C:2]1[C:3]([OH:4])=[C:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[cH:11][cH:12][cH:13][c:14]([C:15]([F:16])([F:... | FC(F)(F)c1cccc(N2CCNCC2)c1.O=C1c2ccccc2C(=O)C2OC12 | O=C1C(O)=C(N2CCN(c3cccc(C(F)(F)F)c3)CC2)C(=O)c2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | d159dfad41809e764977fe62b321d77c82e03faa2312b9af50da554c86691eac | 9eb32644625dfa7918a42cd35d30ff1a368832023364da9d9ecebca843a55107 | O=C1C=C(N2CCN(c3ccccc3)CC2)C(=O)c2ccccc21 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13]2-[O;H0;D2;+0:14]-[CH;D3;+0:15]-1-2>>[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[C;H0;D3;+0:13](-[N;H0;D3;+0:4]2-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-2)=[C;H0;D3;+0:15]-1-[OH;D1;+0:14] | 29.9 | [{"value": 29.9, "product": "OC=1C(C2=CC=CC=C2C(C1N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A mixture of 1.74 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone and 2.30 g of N-[3-(trifluoromethyl)phenyl]piperazine in 100 ml of absolute ethanol was stirred for 20 hours, then evaporated. The residue was dissolved in dichloromethane, filtered through hydrous magnesium silicate and then chromatographed on silica gel,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Secondary amine | Enamine.Ketone.Ketone.Enol | C1CNCC[NH]1.c1ccc2c(c1)CC1OC1C2 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.c1ccccc1.C1=CCc2ccccc2C1 | null | C(C)O | null | 20 | FC(F)(F)c1cccc(N2CCNCC2)c1.O=C1c2ccccc2C(=O)C2OC12>C(C)O>O=C1C(O)=C(N2CCN(c3cccc(C(F)(F)F)c3)CC2)C(=O)c2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dbaeee1d10774d5b9ecd93a63368c816 | CNCCN(C)Cc1ccccc1.O=C1c2ccccc2C(=O)C2OC12>>CN(CCN(C)C1=C(O)C(=O)c2ccccc2C1=O)Cc1ccccc1 | O1C2C(C3=CC=CC=C3C(C21)=O)=O.C(C1=CC=CC=C1)N(CCNC)C>>OC=1C(C2=CC=CC=C2C(C1N(CCN(CC1=CC=CC=C1)C)C)=O)=O | [CH3:1][N:2]([CH2:3][CH2:4][NH:5][CH3:6])[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[CH:7]12[CH:8]([O:9]1)[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[C:18]2=[O:19]>>[CH3:1][N:2]([CH2:3][CH2:4][N:5]([CH3:6])[C:7]1=[C:8]([OH:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]1=[O:19]... | CNCCN(C)Cc1ccccc1.O=C1c2ccccc2C(=O)C2OC12 | CN(CCN(C)C1=C(O)C(=O)c2ccccc2C1=O)Cc1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 0028c448e315ec41f72d3c8a14ffdb1089cc2267edd908074c6e06b32c404332 | 9eb32644625dfa7918a42cd35d30ff1a368832023364da9d9ecebca843a55107 | O=C1C=C(NCCNCc2ccccc2)C(=O)c2ccccc21 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[c:7]:[c:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11]2-[O;H0;D2;+0:12]-[CH;D3;+0:13]-1-2>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[C;H0;D3;+0:11]1=[C;H0;D3;+0:13](-[OH;D1;+0:12])-[C:6](=[O;D1;H0:5])-[c:7]:[c:8]-[C:9]-1=[O;D1;H0:10] | null | [] | null | null | 20 | HOUR | A mixture of 2.61 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone, 2.67 g of N-benzyl-N,N'-dimethylethylenediamine and 150 ml of absolute ethanol was stirred for 20 hours, then concentrated to one-half its original volume and refrigerated overnight. The solvent was removed, the residue dissolved in dichloromethane and pa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Secondary amine | Enamine.Ketone.Ketone.Enol | c1ccc2c(c1)CC1OC1C2 | C1=CCc2ccccc2C1 | C1=CCc2ccccc2C1.c1ccccc1 | null | C(C)O | null | 20 | CNCCN(C)Cc1ccccc1.O=C1c2ccccc2C(=O)C2OC12>C(C)O>CN(CCN(C)C1=C(O)C(=O)c2ccccc2C1=O)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-76e2664d978c4a2197ffbdd9fcee90d3 | O=C1c2ccccc2C(=O)C2OC12.O=CN1CCNCC1>>O=CN1CCN(C2=C(O)C(=O)c3ccccc3C2=O)CC1 | O1C2C(C3=CC=CC=C3C(C21)=O)=O.N1(CCNCC1)C=O>>OC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C=O | [CH:7]12[CH:8]([O:9]1)[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[C:18]2=[O:19].[O:1]=[CH:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:20][CH2:21]1>>[O:1]=[CH:2][N:3]1[CH2:4][CH2:5][N:6]([C:7]2=[C:8]([OH:9])[C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18]2=[O:19])[CH2:20][CH2:21]1 | O=C1c2ccccc2C(=O)C2OC12.O=CN1CCNCC1 | O=CN1CCN(C2=C(O)C(=O)c3ccccc3C2=O)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3d62cca493370f2e39512df12599eb3940fa8a217b80897143eb7507fe49beac | 9eb32644625dfa7918a42cd35d30ff1a368832023364da9d9ecebca843a55107 | O=C1C=C(N2CCNCC2)C(=O)c2ccccc21 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13]2-[O;H0;D2;+0:14]-[CH;D3;+0:15]-1-2>>[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[C;H0;D3;+0:13](-[N;H0;D3;+0:4]2-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-2)=[C;H0;D3;+0:15]-1-[OH;D1;+0:14] | null | [] | null | null | 20 | HOUR | A mixture of 3.48 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone, 2.28 of 1-piperazinecarboxaldehyde and 200 ml of absolute ethanol was stirred for 20 hours, then concentrated to one-half its original volume and refrigerated overnight. The solid was collected and recrystallized from dichloromethane/ethanol, giving 2.65 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Secondary amine | Enamine.Ketone.Ketone.Enol | c1ccc2c(c1)CC1OC1C2.C1C[NH]CCN1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | null | C(C)O | null | 20 | O=C1c2ccccc2C(=O)C2OC12.O=CN1CCNCC1>C(C)O>O=CN1CCN(C2=C(O)C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4a85381d106d486ab137598d3b983c45 | O=C1c2ccccc2C(=O)C2OC12.c1ccc2oc(N3CCNCC3)nc2c1>>O=C1C(O)=C(N2CCN(c3nc4ccccc4o3)CC2)C(=O)c2ccccc21 | O1C2C(C3=CC=CC=C3C(C21)=O)=O.N1(CCNCC1)C=1OC2=C(N1)C=CC=C2>>O1C(=NC2=C1C=CC=C2)N2CCN(CC2)C=2C(C1=CC=CC=C1C(C2O)=O)=O | [O:1]=[C:2]1[CH:3]2[O:4][CH:5]2[C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21.[NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[o:18]2)[CH2:19][CH2:20]1>>[O:1]=[C:2]1[C:3]([OH:4])=[C:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[n:11][c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[o:18]3)... | O=C1c2ccccc2C(=O)C2OC12.c1ccc2oc(N3CCNCC3)nc2c1 | O=C1C(O)=C(N2CCN(c3nc4ccccc4o3)CC2)C(=O)c2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | d159dfad41809e764977fe62b321d77c82e03faa2312b9af50da554c86691eac | 9eb32644625dfa7918a42cd35d30ff1a368832023364da9d9ecebca843a55107 | O=C1C=C(N2CCN(c3nc4ccccc4o3)CC2)C(=O)c2ccccc21 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13]2-[O;H0;D2;+0:14]-[CH;D3;+0:15]-1-2>>[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[C;H0;D3;+0:13](-[N;H0;D3;+0:4]2-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-2)=[C;H0;D3;+0:15]-1-[OH;D1;+0:14] | 14.2 | [{"value": 14.2, "product": "O1C(=NC2=C1C=CC=C2)N2CCN(CC2)C=2C(C1=CC=CC=C1C(C2O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 3.48 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone, 2.03 g of 2-(1-piperazinyl)benzoxazole and 200 ml of absolute ethanol was stirred for 18 hours and then filtered. The filtrate was concentrated to dryness and the residue flash chromatographed, eluting with dichloromethane, then 1% methanol in dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Secondary amine | Enamine.Ketone.Ketone.Enol | c1ccc2c(c1)CC1OC1C2.C1CNCC[NH]1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.c1ccc2ocnc2c1.C1=CCc2ccccc2C1 | null | C(C)O | null | 18 | O=C1c2ccccc2C(=O)C2OC12.c1ccc2oc(N3CCNCC3)nc2c1>C(C)O>O=C1C(O)=C(N2CCN(c3nc4ccccc4o3)CC2)C(=O)c2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-befc1a5140b3477ba8bc5c430cf45d86 | CCOC(=O)N1CCNCC1.O=C1c2ccccc2C(=O)C2OC12>>CCOC(=O)N1CCN(C2=C(O)C(=O)c3ccccc3C2=O)CC1 | O1C2C(C3=CC=CC=C3C(C21)=O)=O.CCOC(=O)N1CCNCC1>>OC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][NH:9][CH2:23][CH2:24]1.[CH:10]12[CH:11]([O:12]1)[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[C:21]2=[O:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10]2=[C:11]([OH:12])[C:13](=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[C:21]2=... | CCOC(=O)N1CCNCC1.O=C1c2ccccc2C(=O)C2OC12 | CCOC(=O)N1CCN(C2=C(O)C(=O)c3ccccc3C2=O)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3d62cca493370f2e39512df12599eb3940fa8a217b80897143eb7507fe49beac | 9eb32644625dfa7918a42cd35d30ff1a368832023364da9d9ecebca843a55107 | O=C1C=C(N2CCNCC2)C(=O)c2ccccc21 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13]2-[O;H0;D2;+0:14]-[CH;D3;+0:15]-1-2>>[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[C;H0;D3;+0:13](-[N;H0;D3;+0:4]2-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-2)=[C;H0;D3;+0:15]-1-[OH;D1;+0:14] | 44.9 | [{"value": 44.9, "product": "OC1=C(C(C2=CC=CC=C2C1=O)=O)N1CCN(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 1.174 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone, 1.58 g of ethyl-N-piperazinocarboxylate and 100 ml of absolute ethanol was stirred for 24 hours, then evaporated. The residue was chromatographed on silica gel, eluting with 5% methanol in chloroform, giving 1.0 g of the desired product, mp 115°-118° C.
... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ether.Secondary amine | Enamine.Ketone.Ketone.Enol | C1C[NH]CCN1.c1ccc2c(c1)CC1OC1C2 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | C1C[NH]CC[NH]1.C1=CCc2ccccc2C1 | null | C(C)O | null | 24 | CCOC(=O)N1CCNCC1.O=C1c2ccccc2C(=O)C2OC12>C(C)O>CCOC(=O)N1CCN(C2=C(O)C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-40f86100453649baaaad16821658abaf | CC(=O)c1ccc(Cl)nc1.[N-]=[N+]=[N-]>>CC(=O)c1ccc2nnnn2c1 | Cl.ClC1=NC=C(C=C1)C(C)=O.[N-]=[N+]=[N-].[Na+].C(C)O>>C(C)(=O)C=1C=CC=2N(C1)N=NN2 | Cl[c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:12][n:11]1.[N-:8]=[N+:10]=[N-:9]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][n:9][n:10][n:11]2[cH:12]1 | CC(=O)c1ccc(Cl)nc1.[N-]=[N+]=[N-] | CC(=O)c1ccc2nnnn2c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 60967d0a10df13474ce7ef580cb6a95c4a598735845b09f5aad8d662786255e3 | 155f764f095c8454a4ad08aaa42f1abcb15d5bc1d4f122e4bcc624dd834362f2 | c1ccn2nnnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8]:[n;H0;D2;+0:9]:1.[N-;H0;D1:10]=[N+;H0;D2:11]=[N-;H0;D1:12]>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:8]:[n;H0;D3;+0:9]2:[n;H0;D2;+0:11]:[n;H0;D2;+0:12]:[n;H0;D2;+0:10]:[c;H0;D3;+0:1]:2:[c:2]:[c:3]:1 | null | [] | null | null | null | null | To a stirred solution of 8.4 gm. (51.6 mmoles) of 2-chloro-5-acetylpyridine and 8.4 gm. (129 mmoles) of sodium azide in 150 ml. of ethanol and 150 ml. of water was added 75 ml. of 10% HCl over a period of 20min. The reaction mixture was then heated to reflux for 18 hours, cooled in an ice bath and the resulting crystal... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccn2nnnc2c1 | c1ccn2nnnc2c1 | Other | O | null | null | CC(=O)c1ccc(Cl)nc1.[N-]=[N+]=[N-]>O>CC(=O)c1ccc2nnnn2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8ec6bc0ba583456dba19b4ce1259fcc1 | O=C(O)c1ccc(F)nc1>>CC(=O)c1ccc(F)nc1 | FC1=NC=C(C=C1)C(=O)O.C[Li]>>C(C)(=O)C=1C=CC(=NC1)F | O[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[n:9][cH:10]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[n:9][cH:10]1 | O=C(O)c1ccc(F)nc1 | CC(=O)c1ccc(F)nc1 | null | null | CCOCC | Functional Group Interconversion | OtherReaction | e9c3cedbcda67d0df54f9106bb41f00b64c34f45c22680bd429b0c3cd51664a5 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[C;D1;H3:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | 2 | HOUR | To suspension of 20 gm. (]42 mmoles) of 2-fluoro-5-pyridinecarboxylic acid (J.Am. Chem. Soc., 71, 1125 (1949)) in 750 ml. of ether, stirred and cooled in ice, was added 225 ml. of 1.6 M methyl lithium (360 mmoles) in ether over 1 hr. The reaction was stirred for an additional 2 hr., then 300 ml. of ice water was added.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | null | null | c1ccncc1 | null | CCOCC | null | 2 | O=C(O)c1ccc(F)nc1>CCOCC>CC(=O)c1ccc(F)nc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b71060c88f1e48328aff893e3244c153 | N#CCc1coc2ccccc12>>NCCc1coc2ccccc12 | C(#N)CC=1C2=C(OC1)C=CC=C2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>O1C2=C(C(=C1)CCN)C=CC=C2 | [N:1]#[C:2][CH2:3][c:4]1[cH:5][o:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12>>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][o:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | N#CCc1coc2ccccc12 | NCCc1coc2ccccc12 | null | null | CCOCC.C(C)OCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2occc2c1 | [#8;a:1]:[c:2]:[c:3]-[C:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[#8;a:1]:[c:2]:[c:3]-[C:4]-[CH2;D2;+0:5]-[NH2;D1;+0:6] | 79.4 | [{"value": 79.4, "product": "O1C2=C(C(=C1)CCN)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3.97 g (0.025 mole) of 3-cyanomethylbenzo[b]furan in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hrs., cooled and water was slowly added. The suspension was filtered through a pad of filte... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2occc2c1 | null | CCOCC.C(C)OCC | null | null | N#CCc1coc2ccccc12>CCOCC.C(C)OCC>NCCc1coc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9b18f248c70e4a0392e77af9b435df2f | CCOC=O.NCCc1coc2ccccc12>>O=CNCCc1coc2ccccc12 | O1C2=C(C(=C1)CCN)C=CC=C2.C(=O)OCC.Cl>>C(=O)NCCC=1C2=C(OC1)C=CC=C2 | CCO[CH:2]=[O:1].[NH2:3][CH2:4][CH2:5][c:6]1[cH:7][o:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[O:1]=[CH:2][NH:3][CH2:4][CH2:5][c:6]1[cH:7][o:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | CCOC=O.NCCc1coc2ccccc12 | O=CNCCc1coc2ccccc12 | null | null | null | Acylation | OtherReaction | 003d6e284475e7d4fe43f9e91e4ad7ca9bf4d7f2029a8fe4e8eed7dbde0fdef0 | 25423bd5162c5be916302ae1ac632b1f2d5d912d0ee7eadf1b5b1259507dc6c3 | c1ccc2occc2c1 | C-C-O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[NH;D2;+0:5]-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | null | null | A solution of 2.35 g (0.015 mole) of 2-(3-benzo[b]furanyl)ethylamine and 5 mL of ethyl formate was heated at 60° C. for 3 hours, poured into 2N HCl and washed with methylene chloride which in turn was washed with 5% sodium hydroxide (w/v), dried (MgSO4), filtered and concentrated to give 2.70 g of product.
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amide | null | null | c1ccc2occc2c1 | HO- | null | null | null | CCOC=O.NCCc1coc2ccccc12>>O=CNCCc1coc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d376c969a22a4ad9a4185fd147ab4198 | CC(=O)Cl.O=Cc1ccc(CO)cc1>>CC(=O)OCc1ccc(C=O)cc1 | OCC1=CC=C(C=O)C=C1.C(C)N(CC)CC.C(C)(=O)Cl>>C(C)(=O)OCC1=CC=C(C=O)C=C1 | Cl[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13]1 | CC(=O)Cl.O=Cc1ccc(CO)cc1 | CC(=O)OCc1ccc(C=O)cc1 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[C:5]-[c:6]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C:5]-[c:6] | 67.6 | [{"value": 67.6, "product": "C(C)(=O)OCC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 54.2 g of 4-hydroxymethylbenzaldehyde, together with 40 g of triethylamine, are dissolved in 350 ml of dichloromethane. After the dropwise addition of 31.2 g of acetyl chloride at 0° to 5° C., the reaction mixture is allowed to stand overnight at room temperature. Thereafter, the precipitated triethylammonium chloride ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | ClCCl | null | 8 | CC(=O)Cl.O=Cc1ccc(CO)cc1>ClCCl>CC(=O)OCc1ccc(C=O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4262ef1b8922496ebfefb960ef4290bd | CC(=O)CCl.Nc1nccc2c(Cl)cccc12>>Cc1cn2ccc3c(Cl)cccc3c2n1 | ClC1=C2C=CN=C(C2=CC=C1)N.ClCC(C)=O.C([O-])(O)=O.[Na+]>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3)C | O=[C:2]([CH3:1])[CH2:3]Cl.[n:4]1[cH:5][cH:6][c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]2[c:14]1[NH2:15]>>[CH3:1][c:2]1[cH:3][n:4]2[cH:5][cH:6][c:7]3[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1 | CC(=O)CCl.Nc1nccc2c(Cl)cccc12 | Cc1cn2ccc3c(Cl)cccc3c2n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 78935ce312554100564931917e18f278a2f0536f5f6cc66905362a94d2708db3 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc2c(c1)ccn1ccnc21 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[n;H0;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6]):[n;H0;D2;+0:4]:1 | 82.4 | [{"value": 82.4, "product": "ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 5-chloro-1-aminoisoquinoline (2.8 g), chloroacetone (5.4 g) and sodium bicarbonate (7.6 g) in anhydrous ethanol (35 ml) was heated at 60° C. for 16 hours and filtered by suction. The filtrate was evaporated in vacuo and the residual solid was washed with ethanol to give 7-chloro-2-methylimidazo[2,1-a]isoqu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccc2cnccc2c1 | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | HCl | C(C)O | 60 | null | CC(=O)CCl.Nc1nccc2c(Cl)cccc12>C(C)O>Cc1cn2ccc3c(Cl)cccc3c2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-181a7e40fb93472d9d081e58c92d33b5 | C=O.CNC.Cc1cn2ccc3c(Cl)cccc3c2n1>>Cc1nc2c3cccc(Cl)c3ccn2c1CN(C)C | [OH-].[Na+].C=O.CNC.ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3)C>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CN(C)C)C | O=[CH2:19].[CH3:16][NH:17][CH3:18].[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[cH:15]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][N:17]([CH3:18])[CH3:19] | C=O.CNC.Cc1cn2ccc3c(Cl)cccc3c2n1 | Cc1nc2c3cccc(Cl)c3ccn2c1CN(C)C | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | f926e897ee7bad83fc9082ae29360b37528a72be55856903bdf8153b0d2166fe | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2c(c1)ccn1ccnc21 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[CH3;D1;+0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8](:[c:9]):[#7;a:10](:[c:11]):[cH;D2;+0:12]:1>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[CH3;D1;+0:1])-[CH2;D2;+0:4]-[c;H0;D3;+0:12]1:[#7;a:10](:[c:11]):[c:8](:[c:9]):[#7;a:7]:[c:6]:1-[C;D1;H3:5] | 71.2 | [{"value": 71.2, "product": "ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CN(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3.5 | HOUR | To a solution of 37% aqueous formaldehyde (0.42 g) and 50% aqueous dimethylamine (0.46 g) in acetic acid (3.2 ml) was added 7-chloro-2-methylimidazo[2,1-a]isoquinoline (1 g) and the mixture was warmed at 50° C. with stirring for 3.5 hours. The solution was poured into ice water and neutralized with an aqueous solution ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | HO- | C(C)(=O)O | 50 | 3.5 | C=O.CNC.Cc1cn2ccc3c(Cl)cccc3c2n1>C(C)(=O)O>Cc1nc2c3cccc(Cl)c3ccn2c1CN(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-05a503c69e62474e8c0cab369e6ea2f1 | COS(=O)(=O)OC.Cc1nc2c3ccccc3ccn2c1CN(C)C>>COS(=O)(=O)[O-].Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C | CN(C)CC1=C(N=C2N1C=CC1=CC=CC=C21)C.S(=O)(=O)(OC)OC.C(C)OCC>>COS(=O)(=O)[O-].CC=1N=C2N(C=CC3=CC=CC=C23)C1C[N+](C)(C)C | [CH3:1][O:2][S:3](=[O:4])(=[O:5])[O:6][CH3:23].[CH3:7][c:8]1[n:9][c:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][n:19]2[c:20]1[CH2:21][N:22]([CH3:24])[CH3:25]>>[CH3:1][O:2][S:3](=[O:4])(=[O:5])[O-:6].[CH3:7][c:8]1[n:9][c:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][n:19]2[c:20]1[CH2:21][... | COS(=O)(=O)OC.Cc1nc2c3ccccc3ccn2c1CN(C)C | COS(=O)(=O)[O-].Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | c1c361ee4cbadaf5c6784ce94893dc199b85d8bd1f54519979f4b44d8dfd8b3e | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc2c(c1)ccn1ccnc21 | [#7;a:1]:[c:2](-[C:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6]):[c:7]:[#7;a:8].[C;D1;H3:9]-[#8:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[O;H0;D2;+0:14]-[CH3;D1;+0:15]>>[#7;a:1]:[c:2](-[C:3]-[N+;H0;D4:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:15]):[c:7]:[#7;a:8].[C;D1;H3:9]-[#8:10]-[#16:11](-[O-;H0;D1:14])(=[O;D1;H0:1... | null | [] | null | null | null | null | A solution of 3-dimethylaminomethyl-2-methylimidazo[2,1-a]isoquinoline (7.7 g) in tetrahydrofuran (20 ml) was added dropwise to a solution of dimethyl sulfate (15 ml) in tetrahydrofuran (40 ml) with ice-cooling and stirring, and the mixture was stirred for 2 hours under the same conditions. To the reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | null | null | c1ccc2c(c1)ccn1ccnc21 | null | O1CCCC1 | null | null | COS(=O)(=O)OC.Cc1nc2c3ccccc3ccn2c1CN(C)C>O1CCCC1>COS(=O)(=O)[O-].Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-93256b0b1b2d4e259b6a55c562dc49d1 | CI.Cc1nc2c3ccc(Cl)cc3ccn2c1CN(C)C>>Cc1nc2c3ccc(Cl)cc3ccn2c1C[N+](C)(C)C.[I-] | CI.ClC=1C=C2C=CN3C(C2=CC1)=NC(=C3CN(C)C)C>>[I-].ClC=1C=C2C=CN3C(C2=CC1)=NC(=C3C[N+](C)(C)C)C | [CH3:18][I:21].[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][N:17]([CH3:19])[CH3:20]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][N+:17]([CH3:18])([CH3:19])[CH3:20].[I-:21] | CI.Cc1nc2c3ccc(Cl)cc3ccn2c1CN(C)C | Cc1nc2c3ccc(Cl)cc3ccn2c1C[N+](C)(C)C.[I-] | null | null | C(C)O | Functional Group Interconversion | OtherReaction | c1c361ee4cbadaf5c6784ce94893dc199b85d8bd1f54519979f4b44d8dfd8b3e | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc2c(c1)ccn1ccnc21 | [#7;a:1]:[c:2](-[C:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6]):[c:7]:[#7;a:8].[CH3;D1;+0:9]-[I;H0;D1;+0:10]>>[#7;a:1]:[c:2](-[C:3]-[N+;H0;D4:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:9]):[c:7]:[#7;a:8].[I-;H0;D0:10] | 84.2 | [{"value": 84.2, "product": "[I-].ClC=1C=C2C=CN3C(C2=CC1)=NC(=C3C[N+](C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | Methyliodide (1.7 g) was added dropwise to a solution of 8-chloro-3-dimethylaminomethyl-2-methylimidazo[2,1-a]isoquinoline (2.8 g) in ethanol (34 ml) at room temperature and the mixture was stirred for 14 hours. The resulting precipitate was collected by filtration, washed with ethanol and dried in a desiccator to give... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | null | null | c1ccc2c(c1)ccn1ccnc21 | null | C(C)O | null | 14 | CI.Cc1nc2c3ccc(Cl)cc3ccn2c1CN(C)C>C(C)O>Cc1nc2c3ccc(Cl)cc3ccn2c1C[N+](C)(C)C.[I-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0f6d18779fe14bc4b673be47f8748154 | Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C.c1c[nH]cn1>>Cc1nc2c3ccccc3ccn2c1Cc1ncc[nH]1 | COS(=O)(=O)[O-].CC=1N=C2N(C=CC3=CC=CC=C23)C1C[N+](C)(C)C.N1C=NC=C1>>N1C(=NC=C1)CC1=C(N=C2N1C=CC1=CC=CC=C21)C | C[N+](C)(C)[CH2:15][c:14]1[c:2]([CH3:1])[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]21.[cH:16]1[n:17][cH:18][cH:19][nH:20]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]2[c:14]1[CH2:15][c:16]1[n:17][cH:18][cH:19][nH:20]1 | Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C.c1c[nH]cn1 | Cc1nc2c3ccccc3ccn2c1Cc1ncc[nH]1 | null | null | C(C)O | C-C Coupling | OtherReaction | 1ab3da90f58e99b3fa575495e50a72ec8bd1a302aac79a5abf60bcbe0f90c405 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc2c(c1)ccn1c(Cc3ncc[nH]3)cnc21 | C-[N+](-C)(-C)-[CH2;D2;+0:1]-[c:2]1:[#7;a:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8].[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[cH;D2;+0:13]:1>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:3](:[c:4]):[c:2]:1-[CH2;D2;+0:1]-[c;H0;D3;+0:13]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:1 | 71.2 | [{"value": 71.2, "product": "N1C(=NC=C1)CC1=C(N=C2N1C=CC1=CC=CC=C21)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | A mixture of 2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (4.5 g) and imidazole (2.02 g) in ethanol (45 ml) was refluxed with stirring for 7 hours and evaporated in vacuo. To the residue was added water and the resulting precipitates were collected by filtration and recrystallized from a mi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccc2c(c1)ccn1ccnc21.c1c[nH]cn1 | Other | C(C)O | null | 7 | Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C.c1c[nH]cn1>C(C)O>Cc1nc2c3ccccc3ccn2c1Cc1ncc[nH]1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f12ff83f9eeb42828ee17781af946cd5 | Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C.Cc1ncc[nH]1>>Cc1nc2c3ccccc3ccn2c1CC1(C)N=CC=N1 | COS(=O)(=O)[O-].CC=1N=C2N(C=CC3=CC=CC=C23)C1C[N+](C)(C)C.CC=1NC=CN1>>CC=1N=C2N(C=CC3=CC=CC=C23)C1CC1(N=CC=N1)C | C[N+](C)(C)[CH2:15][c:14]1[c:2]([CH3:1])[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]21.[c:16]1([CH3:17])[n:18][cH:19][cH:20][nH:21]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]2[c:14]1[CH2:15][C:16]1([CH3:17])[N:18]=[CH:19][CH:20]=[N:21]1 | Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C.Cc1ncc[nH]1 | Cc1nc2c3ccccc3ccn2c1CC1(C)N=CC=N1 | null | null | C(C)O | C-C Coupling | OtherReaction | 6c285af82090e6b98ef89274178823fb4d2c97d2095bafb6d419249fc6f7f7c0 | 184f7d80dc0b974754f7d3970e9cf720d01c801e7b1a9c0474e0cce2fbfd0bb9 | C1=NC(Cc2cnc3c4ccccc4ccn23)N=C1 | C-[N+](-C)(-C)-[CH2;D2;+0:1]-[c:2]1:[#7;a:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8].[C;D1;H3:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[nH;D2;+0:14]:1>>[C;D1;H3:9]-[C;H0;D4;+0:10]1(-[CH2;D2;+0:1]-[c:2]2:[#7;a:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]:2-[C;D1;H3:8])-[N;H0;D2;+0:11]=[CH;D2;+0:12]-[CH;D2;+... | 37.5 | [{"value": 37.5, "product": "CC=1N=C2N(C=CC3=CC=CC=C23)C1CC1(N=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (3 g) and 2-methylimidazole (1.6 g) in ethanol (50 ml) was refluxed with stirring for 4 hours and evaporated in vacuo. To the residue was added water and the resulting precipitates were collected by filtration, dried and recrystalliz... | 10.6084/m9.figshare.5104873.v1 | null | null | Substituted imine.Substituted imine | c1c[nH]cn1 | C1=NCN=C1 | c1ccc2c(c1)ccn1ccnc21.C1=NCN=C1 | Other | C(C)O | null | 4 | Cc1nc2c3ccccc3ccn2c1C[N+](C)(C)C.Cc1ncc[nH]1>C(C)O>Cc1nc2c3ccccc3ccn2c1CC1(C)N=CC=N1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5cf67d07029a4e36b2dd22857e9ca32e | Cc1nc2c3cccc(Cl)c3ccn2c1C[N+](C)(C)C.c1c[nH]cn1>>Cc1nc2c3cccc(Cl)c3ccn2c1Cc1ncc[nH]1 | C(C)O.COS(=O)(=O)[O-].ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3C[N+](C)(C)C)C.N1C=NC=C1>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CC=3NC=CN3)C | C[N+](C)(C)[CH2:16][c:15]1[c:2]([CH3:1])[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]21.[cH:17]1[n:18][cH:19][cH:20][nH:21]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][c:17]1[n:18][cH:19][cH:20][nH:21]1 | Cc1nc2c3cccc(Cl)c3ccn2c1C[N+](C)(C)C.c1c[nH]cn1 | Cc1nc2c3cccc(Cl)c3ccn2c1Cc1ncc[nH]1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | 1ab3da90f58e99b3fa575495e50a72ec8bd1a302aac79a5abf60bcbe0f90c405 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc2c(c1)ccn1c(Cc3ncc[nH]3)cnc21 | C-[N+](-C)(-C)-[CH2;D2;+0:1]-[c:2]1:[#7;a:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8].[#7;a:9]1:[c:10]:[c:11]:[#7;a:12]:[cH;D2;+0:13]:1>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:3](:[c:4]):[c:2]:1-[CH2;D2;+0:1]-[c;H0;D3;+0:13]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:1 | 41 | [{"value": 41.0, "product": "ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CC=3NC=CN3)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | Ethanol (50 ml) was added to a mixture of 7-chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (2.3 g) and imidazole (0.95 g) in dimethyl sulfoxide (20 ml) and heated at 100° C. with stirring for 5 hours. After the removal of ethanol by distillation, the residue was poured into water. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccc2c(c1)ccn1ccnc21.c1c[nH]cn1 | Other | CS(=O)C | 100 | 5 | Cc1nc2c3cccc(Cl)c3ccn2c1C[N+](C)(C)C.c1c[nH]cn1>CS(=O)C>Cc1nc2c3cccc(Cl)c3ccn2c1Cc1ncc[nH]1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9ea9b772f2ac449680941eb9538ee16f | Cc1nc2c3ccccc3ccn2c1CC#N.[N-]=[N+]=[N-]>>Cc1nc2c3ccccc3ccn2c1Cc1nnn[nH]1 | Cl.C(#N)CC1=C(N=C2N1C=CC1=CC=CC=C21)C.[Cl-].[NH4+].[N-]=[N+]=[N-].[Na+].C([O-])(O)=O.[Na+]>>CC=1N=C2N(C=CC3=CC=CC=C23)C1CC1=NN=NN1 | [CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]2[c:14]1[CH2:15][C:16]#[N:17].[N-:18]=[N+:19]=[N-:20]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]2[c:14]1[CH2:15][c:16]1[n:17][n:18][n:19][nH:20]1 | Cc1nc2c3ccccc3ccn2c1CC#N.[N-]=[N+]=[N-] | Cc1nc2c3ccccc3ccn2c1Cc1nnn[nH]1 | null | null | O.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc2c(c1)ccn1c(Cc3nnn[nH]3)cnc21 | [#7;a:1]:[c:2](-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]):[c:6]:[#7;a:7].[N-;H0;D1:8]=[N+;H0;D2:9]=[N-;H0;D1:10]>>[#7;a:1]:[c:2](-[C:3]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[n;H0;D2;+0:8]:[n;H0;D2;+0:9]:[nH;D2;+0:10]:1):[c:6]:[#7;a:7] | 86.7 | [{"value": 86.7, "product": "CC=1N=C2N(C=CC3=CC=CC=C23)C1CC1=NN=NN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 3-cyanomethyl-2-methylimidazo[2,1-a]isoquinoline (2.8 g), ammonium chloride (0.74 g) and sodium azide (0.9 g) in N,N-dimethylformamide (28 ml) was heated at 120°-125° C. with stirring for 18 hours. The solution was poured into water, acidified with concentrated hydrochloric acid and then neutralized with a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccc2c(c1)ccn1ccnc21.c1nnn[nH]1 | null | O.CN(C=O)C | null | 18 | Cc1nc2c3ccccc3ccn2c1CC#N.[N-]=[N+]=[N-]>O.CN(C=O)C>Cc1nc2c3ccccc3ccn2c1Cc1nnn[nH]1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cb697b53c8a94fa7a4450949dd32dd23 | CN(C)C=O.Cc1cn2ccc3c(Cl)cccc3c2n1>>Cc1nc2c3cccc(Cl)c3ccn2c1C=O | [OH-].[Na+].ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3)C.P(=O)(Cl)(Cl)Cl.CN(C=O)C.CN(C=O)C>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3C=O)C | CN(C)[CH:16]=[O:17].[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[cH:15]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH:16]=[O:17] | CN(C)C=O.Cc1cn2ccc3c(Cl)cccc3c2n1 | Cc1nc2c3cccc(Cl)c3ccn2c1C=O | null | null | null | C-C Coupling | OtherReaction | d5c314a91dcd787871cba8969054bfc3edcf395cb9c2c24e493337f14c07a0da | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc2c(c1)ccn1ccnc21 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C;D1;H3:3]-[c:4]1:[#7;a:5]:[c:6](:[c:7]):[#7;a:8](:[c:9]):[cH;D2;+0:10]:1>>[C;D1;H3:3]-[c:4]1:[#7;a:5]:[c:6](:[c:7]):[#7;a:8](:[c:9]):[c;H0;D3;+0:10]:1-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | 80 | CELSIUS | 6 | HOUR | A solution of 7-chloro-2-methylimidazo[2,1-a]isoquinoline (4 g) in N,N-dimethylformamide (40 ml) was added dropwise to a mixture of N,N-dimethylformamide (5.7 ml) and phosphoryl chloride (1.86 ml) under ice cooling. After being stirred at 85°-90° C. for 6 hours, the mixture was poured into ice-water, basified with aque... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | Other | null | 80 | 6 | CN(C)C=O.Cc1cn2ccc3c(Cl)cccc3c2n1>>Cc1nc2c3cccc(Cl)c3ccn2c1C=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bad33391a14d457ea99c0d986f93938b | CC(C)CCON=O.Cc1cn2ccc3c(Cl)cccc3c2n1>>Cc1nc2c3cccc(Cl)c3ccn2c1N=O | N(=O)OCCC(C)C.ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3)C>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3N=O)C | CC(C)CCO[N:16]=[O:17].[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[cH:15]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[N:16]=[O:17] | CC(C)CCON=O.Cc1cn2ccc3c(Cl)cccc3c2n1 | Cc1nc2c3cccc(Cl)c3ccn2c1N=O | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8a9a27bda14d96d3b7c1d80813b1121948071de1e7bcc58c0b006d6d878ebee4 | cf1232fd5519ec578bdba0cee2907500a1299052406ff82030a98b4dcbee91ea | c1ccc2c(c1)ccn1ccnc21 | C-C(-C)-C-C-O-[N;H0;D2;+0:1]=[O;D1;H0:2].[C;D1;H3:3]-[c:4]1:[#7;a:5]:[c:6](:[c:7]):[#7;a:8](:[c:9]):[cH;D2;+0:10]:1>>[C;D1;H3:3]-[c:4]1:[#7;a:5]:[c:6](:[c:7]):[#7;a:8](:[c:9]):[c;H0;D3;+0:10]:1-[N;H0;D2;+0:1]=[O;D1;H0:2] | 39.7 | [{"value": 39.7, "product": "ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3N=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Isoamyl nitrite (140 g) was added to a suspension of 7-chloro-2-methylimidazo[2,1-a]isoquinoline (17.1 g) in dioxane (170 ml) at 50° C. and the mixture was refluxed for 15 minutes. After being cooled, the resulting precipitate was collected by filtration, washed successively with dioxane and diethyl ether and dried in ... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Nitroso | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | HO- | O1CCOCC1 | null | null | CC(C)CCON=O.Cc1cn2ccc3c(Cl)cccc3c2n1>O1CCOCC1>Cc1nc2c3cccc(Cl)c3ccn2c1N=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0a9890bc81aa4816a540a63440317a80 | Cc1nc2c3cccc(Cl)c3ccn2c1N=O>>Cc1nc2c3cccc(Cl)c3ccn2c1N | ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3N=O)C.C(C)(=O)O>>NC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C | O=[N:16][c:15]1[c:2]([CH3:1])[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]21>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[NH2:16] | Cc1nc2c3cccc(Cl)c3ccn2c1N=O | Cc1nc2c3cccc(Cl)c3ccn2c1N | null | [Zn] | O | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | c1ccc2c(c1)ccn1ccnc21 | O=[N;H0;D2;+0:1]-[c:2]1:[#7;a:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8]>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:3](:[c:4]):[c:2]:1-[NH2;D1;+0:1] | 80.6 | [{"value": 80.6, "product": "NC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Zinc powder (10.2 g) was added portionwise to a mixture of 7-chloro-2-methyl-3-nitrosoimidazo[2,1-a]isoquinoline (7.7 g) and acetic acid (100 ml) in water (77 ml) over a period of 7 hours and then the mixture was filtered by suction. The filtrate was evaporated in vacuo and the residue was extracted with chloroform aft... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1ccc2c(c1)ccn1ccnc21 | Other | [Zn].O | null | null | Cc1nc2c3cccc(Cl)c3ccn2c1N=O>[Zn].O>Cc1nc2c3cccc(Cl)c3ccn2c1N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f3890f0223094eaf9a2ee3e8c44021d2 | CCOC=NC#N.Cc1nc2c3cccc(Cl)c3ccn2c1N>>Cc1nc2c3cccc(Cl)c3ccn2c1N=CNC#N | C(#N)N=COCC.NC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C>>C(#N)NC=NC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C | CCO[CH:17]=[N:18][C:19]#[N:20].[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[NH2:16]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[N:16]=[CH:17][NH:18][C:19]#[N:20] | CCOC=NC#N.Cc1nc2c3cccc(Cl)c3ccn2c1N | Cc1nc2c3cccc(Cl)c3ccn2c1N=CNC#N | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | a37366ff71575f45a48ed3e6fbcb7aa2756c4f130276f97e7773c1fa36ecb300 | 500f5fcf4fe90cec5c76ba5467901dd2145f02581496325c98a098ab95a67794 | c1ccc2c(c1)ccn1ccnc21 | C-C-O-[CH;D2;+0:1]=[N;H0;D2;+0:2]-[C:3]#[N;D1;H0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](:[c:10]):[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](:[c:10]):[c:11]:1-[N;H0;D2;+0:12]=[CH;D2;+0:1]-[NH;D2;+0:2]-[C:3]#[N;D1;H0:4] | 35.5 | [{"value": 35.5, "product": "C(#N)NC=NC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | HOUR | Ethyl N-cyanoformimidate (3.2 g) was added to a suspension of 3-amino-7-chloro-2-methylimidazo[2,1-a]isoquinoline (2.3 g) in ethanol (60 ml) and the mixture was stirred at room temperature for 45 hours. The mixture was evaporated in vacuo and the residual solid was washed successively with diethyl ether and ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Cyanamide | null | null | c1ccc2c(c1)ccn1ccnc21 | HO- | C(C)O | null | 45 | CCOC=NC#N.Cc1nc2c3cccc(Cl)c3ccn2c1N>C(C)O>Cc1nc2c3cccc(Cl)c3ccn2c1N=CNC#N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a2572d18a38f4d67add05b3833facf30 | Cc1nc2c3cccc(Cl)c3ccn2c1CSCCN.O=S1(=O)N=C(Cl)c2ccccc21>>Cc1nc2c3cccc(Cl)c3ccn2c1CSCCNC1=NS(=O)(=O)c2ccccc21 | NCCSCC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C.C(C)N(CC)CC.ClC1=NS(C2=C1C=CC=C2)(=O)=O>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CSCCNC3=NS(C1=C3C=CC=C1)(=O)=O)C | [CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][S:17][CH2:18][CH2:19][NH2:20].Cl[C:21]1=[N:22][S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[C... | Cc1nc2c3cccc(Cl)c3ccn2c1CSCCN.O=S1(=O)N=C(Cl)c2ccccc21 | Cc1nc2c3cccc(Cl)c3ccn2c1CSCCNC1=NS(=O)(=O)c2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_N | 8199fc5915162236b20d33826bdc3127d185693d629514b69e969b9e767eacd2 | c0f977b53197d39fa813083b5189dbda6c3d3288d4a3f9a6de603ab0d69db97f | O=S1(=O)N=C(NCCSCc2cnc3c4ccccc4ccn23)c2ccccc21 | Cl-[C;H0;D3;+0:1]1=[#7:2]-[#16:3]-[c:4]:[c:5]-1:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1]1=[#7:2]-[#16:3]-[c:4]:[c:5]-1:[c:6] | 95.2 | [{"value": 95.2, "product": "ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CSCCNC3=NS(C1=C3C=CC=C1)(=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 3-(2-aminoethyl)thiomethyl-7-chloro-2-methylimidazo[2,1-a]isoquinoline (1.5 g) and triethylamine (0.5 g) in ethyl alcohol (35 ml) was added portionwise 3-chloro-1,2-benzisothiazole-1,1dioxide (1.0 g). After being stirred at ambient temperature for 1 hour, the resulting precipitate was collected by filtr... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Primary amine | Secondary amine | c1ccc2sncc2c1 | c1ccc2sncc2c1 | c1ccc2c(c1)ccn1ccnc21.c1ccc2sncc2c1 | HCl | C(C)O | null | 1 | Cc1nc2c3cccc(Cl)c3ccn2c1CSCCN.O=S1(=O)N=C(Cl)c2ccccc21>C(C)O>Cc1nc2c3cccc(Cl)c3ccn2c1CSCCNC1=NS(=O)(=O)c2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-111a73a408064d02b9746897538f896a | CSCc1c(C)nc2c3cccc(Cl)c3ccn12.O=C(OO)c1cccc(Cl)c1>>Cc1nc2c3cccc(Cl)c3ccn2c1CS(C)=O | ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CSC)C.ClC1=CC(=CC=C1)C(=O)OO>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CS(=O)C)C | [CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][S:17][CH3:18].O=C(O[OH:19])c1cccc(Cl)c1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][S:17]([CH3:18])=[O:19] | CSCc1c(C)nc2c3cccc(Cl)c3ccn12.O=C(OO)c1cccc(Cl)c1 | Cc1nc2c3cccc(Cl)c3ccn2c1CS(C)=O | null | null | C(Cl)(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | c1ccc2c(c1)ccn1ccnc21 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#7;a:2]:[c:3](-[C:4]-[S;H0;D2;+0:5]-[C;D1;H3:6]):[c:7]:[#7;a:8]>>[#7;a:2]:[c:3](-[C:4]-[S;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:1]):[c:7]:[#7;a:8] | 64.3 | [{"value": 64.3, "product": "ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CS(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 7-chloro-2-methyl-3-methylthiomethylimidazo[2,1-a]isoquinoline (2 g) in chloroform (20 ml) was added portionwise 70% m-chloroperbenzoic acid (1.78 g). After being stirred under ice cooling for 30 minutes, the mixture was washed successively with aqueous sodium bicarbonate, water and brine, dried over m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccc2c(c1)ccn1ccnc21 | HCl | C(Cl)(Cl)Cl | null | 0.5 | CSCc1c(C)nc2c3cccc(Cl)c3ccn12.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>Cc1nc2c3cccc(Cl)c3ccn2c1CS(C)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8d9ad75ce0ee48ae823f1d493e44156c | CCOC(=O)Cc1c(C)nc2c3cccc(Cl)c3ccn12>>Cc1nc2c3cccc(Cl)c3ccn2c1CC(=O)O | [OH-].[Na+].ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CC(=O)OCC)C.CO>>C(=O)(O)CC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C | CC[O:19][C:17]([CH2:16][c:15]1[c:2]([CH3:1])[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]21)=[O:18]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[CH2:16][C:17](=[O:18])[OH:19] | CCOC(=O)Cc1c(C)nc2c3cccc(Cl)c3ccn12 | Cc1nc2c3cccc(Cl)c3ccn2c1CC(=O)O | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)ccn1ccnc21 | 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] | 74.2 | [{"value": 74.2, "product": "C(=O)(O)CC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of sodium hydroxide (1.25 g) in water (5 ml) was added to a mixture of 7-chloro-3-ethoxycarbonylmethyl-2-methylimidazo[2,1-a]isoquinoline (4.75 g) and methanol (48 ml) and the mixture was refluxed for 1.5 hours. After being cooled, the mixture was evaporated in vacuo and 1N hydrochloric acid (31.4 ml) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)ccn1ccnc21 | Other | O | null | null | CCOC(=O)Cc1c(C)nc2c3cccc(Cl)c3ccn12>O>Cc1nc2c3cccc(Cl)c3ccn2c1CC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5862c7b217584878baaa24553651cf1a | Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)O.O=S(Cl)Cl>>Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)Cl.Cl | C(=O)(O)C1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C.S(=O)(Cl)Cl>>Cl.ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3C(=O)Cl)C | O[C:16]([c:15]1[c:2]([CH3:1])[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]21)=[O:17].O=S([Cl:18])[Cl:19]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[C:16](=[O:17])[Cl:18].[ClH:19] | Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)O.O=S(Cl)Cl | Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)Cl.Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)ccn1ccnc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]:1-[C;D1;H3:9].O=S(-[Cl;H0;D1;+0:10])-[Cl;H0;D1;+0:11]>>[C;D1;H3:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:4](:[c:5]):[c:3]:1-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:10])=[O;D1;H0:2].[ClH;D0;+0:11] | null | [] | null | null | null | null | A mixture of 3-carboxy-7-chloro-2-methylimidazo[2,1-a]isoquinoline (2.5 g) and thionyl chloride (20 ml) was refluxed for 1 hour and evaporated in vacuo. The residual solid was washed with benzene and dried in a desiccator to give 7-chloro-3-chloroformyl-2-methylimidazo[2,1-a]isoquinoline hydrochloride (2.75 g).
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)ccn1ccnc21 | Other | null | null | null | Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)O.O=S(Cl)Cl>>Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)Cl.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-723db561936c4818afb8fb304b155dd1 | Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)Cl.[NH4+]>>Cc1nc2c3cccc(Cl)c3ccn2c1C(N)=O | Cl.ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3C(=O)Cl)C.[OH-].[NH4+]>>C(N)(=O)C1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C | Cl[C:16]([c:15]1[c:2]([CH3:1])[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]21)=[O:18].[NH4+:17]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]3[cH:12][cH:13][n:14]2[c:15]1[C:16]([NH2:17])=[O:18] | Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)Cl.[NH4+] | Cc1nc2c3cccc(Cl)c3ccn2c1C(N)=O | null | null | null | Acylation | OtherReaction | 825fddffa01c850bd0103537ce4e244cb6de8bd215cd5da035957375af67e2c9 | 8805c6321825cef45671bed501723a033e52ab76593d6f4fb97580f38c5af25f | c1ccc2c(c1)ccn1ccnc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]:1-[C;D1;H3:9].[NH4+;D0:10]>>[C;D1;H3:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:4](:[c:5]):[c:3]:1-[C;H0;D3;+0:1](-[NH2;D1;+0:10])=[O;D1;H0:2] | null | [] | null | null | null | null | To 28% ammonium hydroxide (50 ml) was added 7-chloro-3-chloroformyl-2-methylimidazo[2,1-a]isoquinoline hydrochloride (1.3 g) and the mixture was stirred under ice-cooling for 40 minutes. The resulting precipitate was collected by filtration, washed with water and recrystallized from a mixture of chloroform and methanol... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Primary amide | null | null | c1ccc2c(c1)ccn1ccnc21 | HCl | null | null | null | Cc1nc2c3cccc(Cl)c3ccn2c1C(=O)Cl.[NH4+]>>Cc1nc2c3cccc(Cl)c3ccn2c1C(N)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1dc58f9bdebb49a9ac8f93e49b2889db | CC(=O)OC(C)=O.Cc1nc2c3cccc(Cl)c3ccn2c1CO>>CC(=O)OCc1c(C)nc2c3cccc(Cl)c3ccn12 | C(C)(=O)OC(C)=O.ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3CO)C>>C(C)(=O)OCC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]3[cH:18][cH:19][n:20]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]3[cH:18][cH:19][n:20]12 | CC(=O)OC(C)=O.Cc1nc2c3cccc(Cl)c3ccn2c1CO | CC(=O)OCc1c(C)nc2c3cccc(Cl)c3ccn12 | null | null | N1=CC=CC=C1 | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccc2c(c1)ccn1ccnc21 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5](-[C:6]-[OH;D1;+0:7]):[c:8]:[#7;a:9]>>[#7;a:4]:[c:5](-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:8]:[#7;a:9] | 35.8 | [{"value": 35.8, "product": "C(C)(=O)OCC1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Acetic anhydride (0.71 g) was added dropwise to a suspension of 7-chloro-3-hydroxymethyl-2-methylimidazo[2,1-a]isoquinoline (1.43 g) in pyridine (14 ml) and the mixture was stirred at room temperature for 24 hours. The mixture was evaporated in vacuo and the residue was extracted with chloroform after an addition of wa... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccc2c(c1)ccn1ccnc21 | HO- | N1=CC=CC=C1 | null | 24 | CC(=O)OC(C)=O.Cc1nc2c3cccc(Cl)c3ccn2c1CO>N1=CC=CC=C1>CC(=O)OCc1c(C)nc2c3cccc(Cl)c3ccn12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-42b24e713fe94be38ed0e09db8750803 | CCOC(=O)C(Br)C(C)=O.Nc1nccc2c(Cl)cccc12>>CCOC(=O)c1c(C)nc2c3cccc(Cl)c3ccn12 | NC1=NC=CC2=C(C=CC=C12)Cl.C(C)(=O)C(C(=O)OCC)Br.C([O-])(O)=O.[Na+]>>ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3C(=O)OCC)C | O=[C:7]([CH:6](Br)[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8].[NH2:9][c:10]1[c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]2[cH:18][cH:19][n:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10]2[c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]3[cH:18][cH:19][n:20]12 | CCOC(=O)C(Br)C(C)=O.Nc1nccc2c(Cl)cccc12 | CCOC(=O)c1c(C)nc2c3cccc(Cl)c3ccn12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 9291871536236f56f37949a16a753eb2f668aa620f1e00d8b8b579b532f4d373 | 31aa25659cf5accd41f8ff85a49e4d2b829110bf1926ff7161f2261cc71e0db2 | c1ccc2c(c1)ccn1ccnc21 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C;H0;D3;+0:6](=O)-[C;D1;H3:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:6](-[C;D1;H3:7]):[n;H0;D2;+0:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1:[c:12]:[c:13] | 59.1 | [{"value": 59.1, "product": "ClC1=C2C=CN3C(C2=CC=C1)=NC(=C3C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-amino-5-chloroisoquinoline (6.1 g), ethyl 2-acetyl-2-bromoacetate (10.75 g) and sodium bicarbonate (14.36 g) in ethanol (72 ml) was refluxed for 2 hours and then filtered by suction. The filtrate was evaporated in vacuo, and the residue was dissolved in a mixture of chloroform and methanol. The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Ester | c1ccc2cnccc2c1 | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | HBr | C(C)O | null | null | CCOC(=O)C(Br)C(C)=O.Nc1nccc2c(Cl)cccc12>C(C)O>CCOC(=O)c1c(C)nc2c3cccc(Cl)c3ccn12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ede232d689f540df962a4f077637f4cb | CC(=O)C(Cl)C(C)=O.Nc1nccc2c(Cl)cccc12>>CC(=O)c1c(C)nc2c3cccc(Cl)c3ccn12 | NC1=NC=CC2=C(C=CC=C12)Cl.ClC(C(C)=O)C(C)=O>>C(C)(=O)C1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C | O=[C:5]([CH:4](Cl)[C:2]([CH3:1])=[O:3])[CH3:6].[NH2:7][c:8]1[c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]2[cH:16][cH:17][n:18]1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[n:7][c:8]2[c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]3[cH:16][cH:17][n:18]12 | CC(=O)C(Cl)C(C)=O.Nc1nccc2c(Cl)cccc12 | CC(=O)c1c(C)nc2c3cccc(Cl)c3ccn12 | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 9f0f2feb819af86b589d5040ae3a0e6b5661f8a161cc2164158df119601b38b0 | bcfaaca1fff120fc45a5fcf802a81a9be77560ebe832f4ae204a887e33863aca | c1ccc2c(c1)ccn1ccnc21 | Cl-[CH;D3;+0:1](-[C:2](-[C;D1;H3:3])=[O;D1;H0:4])-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:5](-[C;D1;H3:6]):[n;H0;D2;+0:7]:[c:8](:[c:9]):[n;H0;D3;+0:10]:1:[c:11]:[c:12] | 9 | [{"value": 9.0, "product": "C(C)(=O)C1=C(N=C2N1C=CC1=C(C=CC=C21)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 1-amino-5-chloroisoquinoline (10 g) in chloroform (150 ml) was added dropwise 3-chloro-2,4-pentanedione (11.3 g). The mixture was refluxed for 6 hours and then allowed to stand at room temperature over night. The mixture was washed successively with aqueous sodium bicarbonate and water, dried over ma... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone.Primary amine | Ketone | c1ccc2cnccc2c1 | c1ccc2c(c1)ccn1ccnc21 | c1ccc2c(c1)ccn1ccnc21 | HCl | C(Cl)(Cl)Cl | null | null | CC(=O)C(Cl)C(C)=O.Nc1nccc2c(Cl)cccc12>C(Cl)(Cl)Cl>CC(=O)c1c(C)nc2c3cccc(Cl)c3ccn12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-55a62297bd47465797a5e421f0df4cfa | O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CO)CS[C@H]12.O=S(Cl)Cl>>O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CCl)CS[C@H]12 | OCC=1CS[C@H]2N(C1C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)C([C@H]2NC(CC2=CC=CC=C2)=O)=O.N1=CC=CC=C1.CN(C=O)C.S(=O)(Cl)Cl>>ClCC=1CS[C@H]2N(C1C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)C([C@H]2NC(CC2=CC=CC=C2)=O)=O | O[CH2:33][C:32]1=[C:15]([C:16](=[O:17])[O:18][CH:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[N:14]2[C:12](=[O:13])[C@@H:11]([NH:10][C:2](=[O:1])[CH2:3][c:4]3[cH:5][cH:6][cH:7][cH:8][cH:9]3)[C@H:37]2[S:36][CH2:35]1.O=S(Cl)[Cl:34]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:... | O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CO)CS[C@H]12.O=S(Cl)Cl | O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CCl)CS[C@H]12 | null | null | O1CCCC1 | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=CCS[C@H]12 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](=[C:4](-[C:5](-[#8:6])=[O;D1;H0:7])-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11]-[#16:12]>>[#16:12]-[C:11]-[C:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1])=[C:4](-[C:5](-[#8:6])=[O;D1;H0:7])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | 10 | MINUTE | 24 ml (0.3 mole) of pyridine, 400 μl of dimethylformamide and 21.6 ml (0.3 mole) of thionyl chloride are added to a solution of 103 g (0.2 mole) of benzhydryl 3-hydroxymethyl-7β-phenylacetamido-3-cephem-4-carboxylate (prepared, for example, in accordance with Helv. Chim. Acta 57, 2044 (1974)) in 3.5 l of absolute tetra... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1=CN2CC[C@H]2SC1 | HCl | O1CCCC1 | null | 0.166667 | O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CO)CS[C@H]12.O=S(Cl)Cl>O1CCCC1>O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CCl)CS[C@H]12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5eb2f821488b423cbb3ed018620cc075 | CCOc1cc(N)cc2c1OCOC2.O=C(Cl)Cl.OCCF>>CCOc1cc(NC(=O)OCCF)cc2c1OCOC2 | NC1=CC2=C(OCOC2)C(=C1)OCC.C(=O)(Cl)Cl.C(C)N(CC)CC.FCCO>>C(C)OC1=CC(=CC2=C1OCOC2)NC(OCCF)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([NH2:7])[cH:14][c:15]2[c:16]1[O:17][CH2:18][O:19][CH2:20]2.Cl[C:8](Cl)=[O:9].[OH:10][CH2:11][CH2:12][F:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][CH2:12][F:13])[cH:14][c:15]2[c:16]1[O:17][CH2:18][O:19][CH2:20]2 | CCOc1cc(N)cc2c1OCOC2.O=C(Cl)Cl.OCCF | CCOc1cc(NC(=O)OCCF)cc2c1OCOC2 | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | b9a97ff2417df5b07cd245547160f318b3ee4c220885157f31c57fa8ad11f8d8 | f648f3bd7738cca164e5812489428a703ee1a6f16fe0021eb651dccc8ad51d2f | c1ccc2c(c1)COCO2 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[C:3]-[C:4]-[OH;D1;+0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:3]-[C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 80.9 | [{"value": 80.9, "product": "C(C)OC1=CC(=CC2=C1OCOC2)NC(OCCF)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 6-amino-8-ethoxy-1,3-benzodioxane (1.95 g) in toluene (20 ml), a toluene solution containing phosgene (10 g) was dropwise added at 10° to 20° C. The resultant mixture was heated gradually and, after being refluxed for 30 minutes, cooled to room temperature. The solvent was removed in vacuo, whereby cru... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol.Primary amine | Carbamic ester | null | null | c1ccc2c(c1)COCO2 | HCl | C1(=CC=CC=C1)C | null | 12 | CCOc1cc(N)cc2c1OCOC2.O=C(Cl)Cl.OCCF>C1(=CC=CC=C1)C>CCOc1cc(NC(=O)OCCF)cc2c1OCOC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-323422090e9547dfb62757ce11acaab4 | CCOc1cc(NC(=O)OC(C)C)cc2c1OCOC2.ClSc1ccccc1>>CCOc1cc(N(Sc2ccccc2)C(=O)OC(C)C)cc2c1OCOC2 | C(C)OC1=CC(=CC2=C1OCOC2)NC(OC(C)C)=O.[H-].[Na+].C1(=CC=CC=C1)SCl>>C1(=CC=CC=C1)SN(C(OC(C)C)=O)C1=CC2=C(OCOC2)C(=C1)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([NH:7][C:15](=[O:16])[O:17][CH:18]([CH3:19])[CH3:20])[cH:21][c:22]2[c:23]1[O:24][CH2:25][O:26][CH2:27]2.Cl[S:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([N:7]([S:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[C:15](=[O:16])[O:17][CH:18]([CH3:19]... | CCOc1cc(NC(=O)OC(C)C)cc2c1OCOC2.ClSc1ccccc1 | CCOc1cc(N(Sc2ccccc2)C(=O)OC(C)C)cc2c1OCOC2 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 904308bf2e7159b3fe00138f3899dcaffed6bbc14abc75a8cb4792c4d62a56f5 | 799664d421c709dc35fc986fe3317bdbac806c17bcf4a7b207ba1607f5e6b494 | c1ccc(SNc2ccc3c(c2)COCO3)cc1 | Cl-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:10](:[c:11]):[c:12] | 87.6 | [{"value": 87.5, "product": "C1(=CC=CC=C1)SN(C(OC(C)C)=O)C1=CC2=C(OCOC2)C(=C1)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "C1(=CC=CC=C1)SN(C(OC(C)C)=O)C1=CC2=C(OCOC2)C(=C1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium hydride (0.107 g; 60% dispersion in mineral oil) was dispersed in N,N-dimethylformamide (20 ml). To this solution was added isopropyl N-(8-ethoxy-1,3-benzodioxan-6-yl)carbamate (0.75 g) under ice-cooling. After being stirred at room temperature for 1 hour, phenylsulfenyl chloride (0.39 g) was added thereto under... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Monosulfide | Carbamic ester.Monosulfide | null | null | c1ccccc1.c1ccc2c(c1)COCO2 | HCl | CN(C=O)C | null | 1 | CCOc1cc(NC(=O)OC(C)C)cc2c1OCOC2.ClSc1ccccc1>CN(C=O)C>CCOc1cc(N(Sc2ccccc2)C(=O)OC(C)C)cc2c1OCOC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fbaca76123ad49008aae318ff22f3088 | CCOC(=O)C1C(=O)N(CC)c2ccc(C3(C)OCCO3)cc21.Nc1ccc(F)cc1F>>CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C3(C)OCCO3)ccc21 | Cl.C(Cl)Cl.C(C)N1C(C(C2=CC(=CC=C12)C1(OCCO1)C)C(=O)OCC)=O.FC1=C(N)C=CC(=C1)F>>FC1=C(C=CC(=C1)F)NC(=O)C1C(N(C2=CC=C(C=C12)C1(OCCO1)C)CC)=O | CCO[C:7]([CH:6]1[C:4](=[O:5])[N:3]([CH2:2][CH3:1])[c:29]2[c:18]1[cH:19][c:20]([C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1)[cH:27][cH:28]2)=[O:8].[NH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]1[F:17]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2... | CCOC(=O)C1C(=O)N(CC)c2ccc(C3(C)OCCO3)cc21.Nc1ccc(F)cc1F | CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C3(C)OCCO3)ccc21 | null | null | C1=CC=CC=C1 | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(Nc1ccccc1)C1C(=O)Nc2ccc(C3OCCO3)cc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[c:4]:[c:5]-[#7:6](-[C:7])-[C:8]-1=[O;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:7]-[#7:6]1-[c:5]:[c:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:8]-1=[O;D1;H0:9] | 80 | [{"value": 80.0, "product": "FC1=C(C=CC(=C1)F)NC(=O)C1C(N(C2=CC=C(C=C12)C1(OCCO1)C)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.0 g. (3.1 mmoles) of ethyl 1-ethyl-5-(2-methyl-4,5-dihydro-1,3-dioxol-2-yl)oxindole-3-carboxylate and 809 mg. (6.3 mmoles) of 2,4-difluoroaniline in 40 ml of benzene was heated to reflux through a soxhlet filled with 4A sieves for 45 minutes. The reaction mixture was cooled and poured into a mixture of 4... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2.C1COCO1 | HO- | C1=CC=CC=C1 | null | null | CCOC(=O)C1C(=O)N(CC)c2ccc(C3(C)OCCO3)cc21.Nc1ccc(F)cc1F>C1=CC=CC=C1>CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C3(C)OCCO3)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-853080dc47954cab85e3613655c71d91 | CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C3(C)OCCO3)ccc21>>CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C(C)=O)ccc21 | FC1=C(C=CC(=C1)F)NC(=O)C1C(N(C2=CC=C(C=C12)C1(OCCO1)C)CC)=O.O1CCCC1.Cl>>FC1=C(C=CC(=C1)F)NC(=O)C1C(N(C2=CC=C(C=C12)C(C)=O)CC)=O | C1C[O:23][C:21]([c:20]2[cH:19][c:18]3[c:26]([cH:25][cH:24]2)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[CH:6]3[C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[F:17])([CH3:22])O1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[F:17])[c:18]2[cH:19][... | CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C3(C)OCCO3)ccc21 | CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C(C)=O)ccc21 | null | null | O | Miscellaneous | Ketal hydrolysis to ketone | bc99a45944d6d67c8bd263755d04463b42623d20ce36570ebfd14e405f44ca50 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C(Nc1ccccc1)C1C(=O)Nc2ccccc21 | [C;D1;H3:1]-[C;H0;D4;+0:2]1(-[c:3](:[c:4]):[c:5])-O-C-C-[O;H0;D2;+0:6]-1>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:6])-[c:3](:[c:4]):[c:5] | 73 | [{"value": 73.0, "product": "FC1=C(C=CC(=C1)F)NC(=O)C1C(N(C2=CC=C(C=C12)C(C)=O)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | N-(2,4-Difluorophenyl)-1-ethyl-5-(2-methyl-4,5-dihydro-1,3-dioxol-2-yl)oxindol-3-carboxamide (636 mg., 1.58 mmoles) was dissolved in 15 ml. of tetrahydrofuran to which was added 10 ml. of 1N hydrochloric acid. The solution was stirred for one hour followed by the addition of an equal volume of water. The resulting prec... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1COCO1 | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | O | null | 1 | CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C3(C)OCCO3)ccc21>O>CCN1C(=O)C(C(=O)Nc2ccc(F)cc2F)c2cc(C(C)=O)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-de8eb938f854499db8dc033cab51fe90 | CCN1C(=O)Cc2ccccc21>>CCN1C(=O)Cc2cc(C=O)ccc21 | COC(Cl)Cl.C(C)N1C(CC2=CC=CC=C12)=O.COC(Cl)Cl>>C(C)N1C(CC2=CC(=CC=C12)C=O)=O | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][cH:9][cH:12][cH:13][c:14]21>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([CH:10]=[O:11])[cH:12][cH:13][c:14]21 | CCN1C(=O)Cc2ccccc21 | CCN1C(=O)Cc2cc(C=O)ccc21 | null | [Ti](Cl)(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl | C(Cl)Cl | Miscellaneous | OtherReaction | 7411dfc8672888ceb211fc5e1d3019bf18f4b5648ebb82adb2b5243009e4359d | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | O=C1Cc2ccccc2N1 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]:[c:5]>>[O;D1;H0:6]=[C:7]-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]:[c:5] | 76 | [{"value": 76.0, "product": "C(C)N1C(CC2=CC(=CC=C12)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 10.5 | DAY | To a solution of 32.2 g. (0.2 mole) of 1-ethyloxindole in 200 ml. of methylene chloride was added 44 ml. (0.4 mole) of titanium tetrachloride followed by 22.6 ml. (0.25 mole) of dichloromethyl methyl ether. The reaction was stirred for 10.5 days at 25° C. followed by the addition of additional titanium tetrachloride an... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | Other | [Ti](Cl)(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl | 25 | 252 | CCN1C(=O)Cc2ccccc21>[Ti](Cl)(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>CCN1C(=O)Cc2cc(C=O)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-13d693696b6c40afae66096a9a28bbb9 | CCN1C(=O)Cc2cc(CCC(=O)OC)ccc21>>CCN1C(=O)Cc2cc(CCC(=O)O)ccc21 | C(C)N1C(CC2=CC(=CC=C12)CCC(=O)OC)=O.[OH-].[Na+].Cl>>C(C)N1C(CC2=CC(=CC=C12)CCC(=O)O)=O | C[O:14][C:12]([CH2:11][CH2:10][c:9]1[cH:8][c:7]2[c:17]([cH:16][cH:15]1)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[CH2:6]2)=[O:13]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([CH2:10][CH2:11][C:12](=[O:13])[OH:14])[cH:15][cH:16][c:17]21 | CCN1C(=O)Cc2cc(CCC(=O)OC)ccc21 | CCN1C(=O)Cc2cc(CCC(=O)O)ccc21 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1Cc2ccccc2N1 | 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] | 93 | [{"value": 93.0, "product": "C(C)N1C(CC2=CC(=CC=C12)CCC(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 12.9 g. (52.2 mmoles) of 1-ethyl-5-(2-carbomethoxyethyl)oxindole in 53 ml. of methanol was added 112.5 ml. of 1N sodium hydroxide solution. After stirring for 1 hour the reaction mixture was acidified by the addition of 165 ml. of 1N hydrochloric acid. The precipitated product was filtered and dried, 1... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)CC[NH]2 | Other | CO | null | 1 | CCN1C(=O)Cc2cc(CCC(=O)OC)ccc21>CO>CCN1C(=O)Cc2cc(CCC(=O)O)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1e2ecc46940240de9aedcef37e969379 | CCCN1C(=O)Cc2cc3c(cc21)C(=O)CC3>>CCN1C(=O)Cc2cc3c(cc21)C(=O)CC3 | CN1C(CC2=CC3=C(C=C12)C(CC3)=O)=O.C1(=CC=CC=C1)N1C(CC2=CC3=C(C=C12)C(CC3)=O)=O.C(CC)N1C(CC2=CC3=C(C=C12)C(CC3)=O)=O.C(C)(C)N1C(CC2=CC3=C(C=C12)C(CC3)=O)=O>>C(C)N1C(CC2=CC3=C(C=C12)C(CC3)=O)=O | C[CH2:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]21)[C:13](=[O:14])[CH2:15][CH2:16]3>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]3[c:10]([cH:11][c:12]21)[C:13](=[O:14])[CH2:15][CH2:16]3 | CCCN1C(=O)Cc2cc3c(cc21)C(=O)CC3 | CCN1C(=O)Cc2cc3c(cc21)C(=O)CC3 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1Cc2cc3c(cc2N1)C(=O)CC3 | C-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5]>>[CH3;D1;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | null | [] | null | null | null | null | Starting with the appropriate 1-substituted-5-hydroxyoxindole and following the procedure of Preparation A, 1-methyl-2,7-dioxo-2,3,5,6-tetrahydro-7H-cyclopenta[f]indole, 1-phenyl-2,7-dioxo-2,3,5,6-tetrahydro-7H-cyclopenta[f]indole, 1-n-propyl-2,7-dioxo-2,3,5,6-tetrahydro-7H-cyclopenta[f]indole and 1-i-propyl-2,7-dioxo-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1c2c(cc3c1CC[NH]3)CCC2 | Other | null | null | null | CCCN1C(=O)Cc2cc3c(cc21)C(=O)CC3>>CCN1C(=O)Cc2cc3c(cc21)C(=O)CC3 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e92da1eef89c454781325f5bee029024 | CCN1C(=O)Cc2cc(O)ccc21.O=C(Cl)CCl>>CCN1C(=O)Cc2cc(OC(=O)CCl)ccc21 | C(C)N1C(CC2=CC(=CC=C12)O)=O.ClCC(=O)Cl.N1=CC=CC=C1>>C(C)N1C(CC2=CC(=CC=C12)OC(CCl)=O)=O | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([OH:10])[cH:15][cH:16][c:17]21.Cl[C:11](=[O:12])[CH2:13][Cl:14]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH2:6][c:7]2[cH:8][c:9]([O:10][C:11](=[O:12])[CH2:13][Cl:14])[cH:15][cH:16][c:17]21 | CCN1C(=O)Cc2cc(O)ccc21.O=C(Cl)CCl | CCN1C(=O)Cc2cc(OC(=O)CCl)ccc21 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C1Cc2ccccc2N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 15 | MINUTE | To a slurry of 100 g. (0.565 mole) of 1-ethyl-5-hydroxyoxindole in 91.3 ml. (1.13 moles) of pyridine and 565 ml. of dichloromethane at 0° C. was added dropwise a solution of 89.3 ml. (1.13 moles) of chloroacetyl chloride in 100 ml. of dichloromethane. The reaction mixture was allowed to stir for 15 minutes, and was the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccc2c(c1)CC[NH]2 | HCl | ClCCl | null | 0.25 | CCN1C(=O)Cc2cc(O)ccc21.O=C(Cl)CCl>ClCCl>CCN1C(=O)Cc2cc(OC(=O)CCl)ccc21 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.