dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-4cbd87311b894e64af3aedbc4e278737 | ClCCCBr.c1ccc(CCN2CCNCC2)cc1>>Cl.Cl.ClCCCN1CCN(CCc2ccccc2)CC1 | C(CC1=CC=CC=C1)N1CCNCC1.[OH-].[K+].BrCCCCl>>Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCCl | Br[CH2:6][CH2:5][CH2:4][Cl:1].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1 | ClCCCBr.c1ccc(CCN2CCNCC2)cc1 | Cl.Cl.ClCCCN1CCN(CCc2ccccc2)CC1 | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CCN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 188.8 | [{"value": 64.0, "product": "Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 188.8, "product": "Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(a) was followed, using 29.4 g of 1-phenethyl piperazine, 25.0 g of potassium hydroxide, 100 ml of dimethyl sulfoxide and 24.0 g of 1-bromo-3-chloropropane. Work-up, as described above, gave 32.6 g (64% of theory) of 1-phenethyl-4-(3-chloropropyl)piperazine dihydrochloride as an off-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | CS(=O)C | null | null | ClCCCBr.c1ccc(CCN2CCNCC2)cc1>CS(=O)C>Cl.Cl.ClCCCN1CCN(CCc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a12cdbab8eb74afc9c6c800abef1a068 | Cl.ClCCCN1CCN(CCc2ccccc2)CC1.NC(N)=S>>Cl.SCCCN1CCN(CCc2ccccc2)CC1 | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCCl>>Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCS | [ClH:2].Cl[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1 | Cl.ClCCCN1CCN(CCc2ccccc2)CC1.NC(N)=S | Cl.SCCCN1CCN(CCc2ccccc2)CC1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CCN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 81.6 | [{"value": 79.0, "product": "Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 15.2 g of thiourea, 32.6 g of 1-phenethyl-4-(3-chloropropyl)piperazine dihydrochloride, 20.0 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 10.0 g of sodium hydroxide in 40 ml of water. Work-up, as described above, gave 26.4... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.ClCCCN1CCN(CCc2ccccc2)CC1.NC(N)=S>C(C)O.O>Cl.SCCCN1CCN(CCc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5ecfcbe5ec174867b5a9332b168281de | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCc2ccccc2)CC1>>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | C1(=CC=CC=C1)N=C=O.Cl.Cl.C(CC1=CC=CC=C1)N1CCN(CC1)CCCS.C(C)N(CC)CC>>O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=CC=C1 | [ClH:2].[O:3]=[C:5]=[N:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[SH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH2:30]1>>[ClH:2].[OH2:3].[OH:4][C:5]([NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[SH:13][CH2:14][CH2:15][CH2:16][N:17]1... | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCc2ccccc2)CC1 | Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 3bf647ffd3af34283e2312f784edbca620c93d73a88c64f1c90f0c5841a13287 | c6ec1d581e09757064752f97a5c83429292625d25a23d379af2b6feb108d2455 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[O;D1;H1:10])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9].[OH2;D0;+0:4] | 67.9 | [{"value": 35.0, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.4 g of phenyl isocyanate, 4.0 g of 3-(4-phenethylpiperazin-1-yl)propanethiol dihydrochloride, 2.4 g of triethylamine and 50 ml of methylene chloride, to give 1.9 g (35% of theory) of N-phenyl-S-[3-(4-phenethylpiperazin-1-yl)propyl]thiocarbamate dihydrochloride ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCc2ccccc2)CC1>C(Cl)Cl>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3718907b4bb04353b2d6e7ee3e40a47d | ClCCCBr.Clc1ccc(CCN2CCNCC2)cc1>>Cl.Cl.ClCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | ClC1=CC=C(CCN2CCNCC2)C=C1.[OH-].[K+].BrCCCCl>>Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCCl)C=C1 | Br[CH2:6][CH2:5][CH2:4][Cl:1].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1 | ClCCCBr.Clc1ccc(CCN2CCNCC2)cc1 | Cl.Cl.ClCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CCN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 118.3 | [{"value": 59.0, "product": "Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 118.3, "product": "Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCCl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 17(a) was followed, using 6.5 g of 1-(4-chlorophenethyl)piperazine, 6.0 g of potassium hydroxide, 125 ml of dimethyl sulfoxide and 4.6 g of 1-bromo-3-chloropropane. Work-up, as described above, gave 6.4 g (59% of theory) of 1-(4-chlorophenethyl)-4-(3-chloropropyl)piperazine dihydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | CS(=O)C | null | null | ClCCCBr.Clc1ccc(CCN2CCNCC2)cc1>CS(=O)C>Cl.Cl.ClCCCN1CCN(CCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5c4b8b9e101c4986b417b515edcf6735 | Cl.ClCCCN1CCN(CCc2ccc(Cl)cc2)CC1.NC(N)=S>>Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCCl)C=C1>>Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1 | [ClH:2].Cl[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[CH2:20][CH2:21]1 | Cl.ClCCCN1CCN(CCc2ccc(Cl)cc2)CC1.NC(N)=S | Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CCN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 176.1 | [{"value": 89.0, "product": "Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 176.1, "product": "Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 1.3 g of thiourea, 6.4 g of 1-(4-chlorophenethyl)-4-(3-chloropropyl)piperazine dihydrochloride, 1.6 g of triethylamine and 150 ml of reagent ethanol. The hydrolysis was effected with 3.5 g of sodium hydroxide and 40 ml of water. Work-up, as described above, ga... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.ClCCCN1CCN(CCc2ccc(Cl)cc2)CC1.NC(N)=S>C(C)O.O>Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c3adcdd7c4ee4836a73f889b5c888b78 | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccc(Cl)cc2)CC1 | C1(=CC=CC=C1)N=C=O.Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl | [ClH:2].[O:3]=[C:5]=[N:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[SH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[CH2:30][CH2:31]1>>[ClH:2].[OH2:3].[OH:4][C:5]([NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[SH:13][CH2:14][CH2:15][CH2:16... | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccc(Cl)cc2)CC1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 3bf647ffd3af34283e2312f784edbca620c93d73a88c64f1c90f0c5841a13287 | c6ec1d581e09757064752f97a5c83429292625d25a23d379af2b6feb108d2455 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[O;D1;H1:10])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9].[OH2;D0;+0:4] | 87.4 | [{"value": 44.0, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.6 g of phenyl isocyanate, 5.0 g of 3-[4-(4-chlorophenethyl)piperazin-1-yl]propanethiol dihydrochloride, 1.3 g of triethylamine and 50 ml of methylene chloride, to give 3.0 g (44% of theory) of N-phenyl-S-{3-[4-(4-chlorophenethyl)piperazin-1-yl]propyl}thiocarbam... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>C(Cl)Cl>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-92cc679236af4645bac266887faa5c2d | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>>CCCCc1ccc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc1.Cl | C(CCC)C1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.C(CCC)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N:9]=[C:10]=[O:11])[cH:31][cH:32]1.[ClH:34].[SH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10]([OH:11])=[... | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | CCCCc1ccc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 49.7 | [{"value": 25.0, "product": "Cl.Cl.C(CCC)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.7, "product": "Cl.Cl.C(CCC)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.4 g of 4-n-butylphenyl isocyanate, 3.0 g of 3-[4-(4-chlorophenethyl)piperazin-1-yl]propanethiol dihydrochloride, 0.8 g of triethylamine and 50 ml of methylene chloride, to give 1.1 g (25% of theory) of N-(4-n-butylphenyl)-S-{3-[4-(4-chlorophenethyl)piperazin-1-... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>C(Cl)Cl>CCCCc1ccc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-524f4e4c964d4f9a84b265af1db184ef | COc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>>COc1ccc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc1.Cl | COC1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]=[C:8]=[O:9])[cH:29][cH:30]1.[ClH:32].[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([OH:9])=[SH:10][CH2:11][CH2:12][CH2:13][N:14]... | COc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | COc1ccc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 49.8 | [{"value": 25.0, "product": "Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.8, "product": "Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.7 g of 4-methoxyphenyl isocyanate, 4.0 g of 3-[4-(4-chlorophenethyl)piperazin-1-yl]propanethiol dihydrochloride, 1.1 g of triethylamine and 50 ml of methylene chloride, to give 1.4 g (25% of theory) of N-(4-methoxyphenyl)-S-{3-[4-(4-chlorophenethyl)piperazin-1-... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>C(Cl)Cl>COc1ccc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a578f973ce364f93924ecc2ae775a857 | COc1cc(N=C=O)cc(OC)c1OC.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>>COc1cc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc(OC)c1OC.Cl | COC=1C=C(C=C(C1OC)OC)N=C=O.Cl.Cl.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>Cl.Cl.COC=1C=C(C=C(C1OC)OC)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[C:7]=[O:8])[cH:28][c:29]([O:30][CH3:31])[c:32]1[O:33][CH3:34].[ClH:36].[SH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7]([OH:8])=[SH:9][CH2:10][... | COc1cc(N=C=O)cc(OC)c1OC.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | COc1cc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc(OC)c1OC.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 46.4 | [{"value": 23.0, "product": "Cl.Cl.COC=1C=C(C=C(C1OC)OC)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "Cl.Cl.COC=1C=C(C=C(C1OC)OC)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 2.5 g of 3,4,5-trimethoxyphenyl isocyanate, 4.4 g of 3-[4-(4-chlorophenethyl)piperazin-1-yl]propanethiol dihydrochloride, 1.2 g of triethylamine and 50 ml of methylene chloride, to give 1.6 g (23% of theory) of N-(3,4,5-trimethoxyphenyl)-S-{3-[4-(4-chlorophenethy... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1cc(N=C=O)cc(OC)c1OC.Cl.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>C(Cl)Cl>COc1cc(NC(O)=[SH]CCCN2CCN(CCc3ccc(Cl)cc3)CC2)cc(OC)c1OC.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-249a67ffce174364b0ae5c54cd4ac01c | ClCCCBr.c1ccc(CCCN2CCNCC2)cc1>>Cl.Cl.ClCCCN1CCN(CCCc2ccccc2)CC1 | C1(=CC=CC=C1)CCCN1CCNCC1.[OH-].[K+].BrCCCCl>>Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCCl | Br[CH2:6][CH2:5][CH2:4][Cl:1].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1 | ClCCCBr.c1ccc(CCCN2CCNCC2)cc1 | Cl.Cl.ClCCCN1CCN(CCCc2ccccc2)CC1 | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CCCN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 219.3 | [{"value": 73.0, "product": "Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 219.3, "product": "Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 17(a) was followed, using 36.0 g of (3-phenylpropyl)piperazine, 25.0 g of potassium hydroxide, 125 ml of dimethyl sulfoxide and 28.0 g of 1-bromo-3-chloropropane, to give 46.0 g (73% of theory) of 1-(3-phenylpropyl)-4-(3-chloropropyl)piperazine dihydrochloride.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | CS(=O)C | null | null | ClCCCBr.c1ccc(CCCN2CCNCC2)cc1>CS(=O)C>Cl.Cl.ClCCCN1CCN(CCCc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-63495ea5d1234e62baec2879feb6bdcc | Cl.ClCCCN1CCN(CCCc2ccccc2)CC1.NC(N)=S>>Cl.SCCCN1CCN(CCCc2ccccc2)CC1 | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCCl>>Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCS | [ClH:2].Cl[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1 | Cl.ClCCCN1CCN(CCCc2ccccc2)CC1.NC(N)=S | Cl.SCCCN1CCN(CCCc2ccccc2)CC1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CCCN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 82 | [{"value": 82.0, "product": "Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.9, "product": "Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 19.0 g of thiourea, 44.0 g of 1-(3-phenylpropyl)-4-(3-chloropropyl)piperazine dihydrochloride, 25 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 10.0 g of sodium hydroxide in 50 ml of water. Work-up, as described above, gave... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.ClCCCN1CCN(CCCc2ccccc2)CC1.NC(N)=S>C(C)O.O>Cl.SCCCN1CCN(CCCc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-abf8bcdd1c6d4d7c97ff0a1a653f9a5d | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCCc2ccccc2)CC1>>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCCc2ccccc2)CC1 | C1(=CC=CC=C1)N=C=O.Cl.Cl.C1(=CC=CC=C1)CCCN1CCN(CC1)CCCS.C(C)N(CC)CC>>O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=CC=C1 | [ClH:2].[O:3]=[C:5]=[N:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[SH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1>>[ClH:2].[OH2:3].[OH:4][C:5]([NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[SH:13][CH2:14][CH2:15][CH2:16... | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCCc2ccccc2)CC1 | Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCCc2ccccc2)CC1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 3bf647ffd3af34283e2312f784edbca620c93d73a88c64f1c90f0c5841a13287 | c6ec1d581e09757064752f97a5c83429292625d25a23d379af2b6feb108d2455 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCCc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[O;D1;H1:10])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9].[OH2;D0;+0:4] | 85 | [{"value": 41.0, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "O.Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.2 g of phenyl isocyanate, 4.0 g of 3-[4-(3-phenylpropyl)piperazin-1-yl]propanethiol dihydrochloride, 2.2 g of triethylamine and 50 ml of methylene chloride, to give 2.1 g (41% of theory) of N-phenyl-S-{3-[4-(3-phenylpropyl)piperazin-1-yl]propyl}thiocarbamate di... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | Cl.O=C=Nc1ccccc1.SCCCN1CCN(CCCc2ccccc2)CC1>C(Cl)Cl>Cl.O.OC(Nc1ccccc1)=[SH]CCCN1CCN(CCCc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ad02dc0d397f4092b422fb887e5d9b33 | ClCCCBr.Clc1ccc(CCCN2CCNCC2)cc1>>Cl.Cl.ClCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 | ClC1=CC=C(C=C1)CCCN1CCNCC1.[OH-].[K+].BrCCCCl>>Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCCl | Br[CH2:6][CH2:5][CH2:4][Cl:1].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1 | ClCCCBr.Clc1ccc(CCCN2CCNCC2)cc1 | Cl.Cl.ClCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CCCN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 104.9 | [{"value": 54.0, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.9, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 17(a) was followed, using 27.0 g of 3-(4-chlorophenyl)propyl piperazine, 22.0 g of potassium hydroxide, 250 ml of dimethyl sulfoxide and 17.7 g of 1-bromo-3-chloropropane to give 22.9 g (54% of theory) of 1-[3-(4-chlorophenyl)propyl]-4-(3-chloropropyl)piperazine dihydrochloride.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | CS(=O)C | null | null | ClCCCBr.Clc1ccc(CCCN2CCNCC2)cc1>CS(=O)C>Cl.Cl.ClCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-25a33070dbbc46b2856cae32c57e7fb1 | Cl.Clc1ccc(CCCN2CCN(c3cccc(Cl)c3)CC2)cc1.NC(N)=S>>Cl.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)C1=CC(=CC=C1)Cl>>Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCS | [ClH:2].Clc1cc[cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]3)[CH2:21][CH2:22]2)c1.N[C:4](N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22... | Cl.Clc1ccc(CCCN2CCN(c3cccc(Cl)c3)CC2)cc1.NC(N)=S | Cl.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 | null | null | C(C)O.O | C-C Coupling | OtherReaction | 69195008f3ff4f25000daeb30917666f63686186c48877497716d23c84933d13 | 41a61ea33577e1fce20b89f6335d2850b4b949c2950a98f7fc57fc76dcf35289 | c1ccc(CCCN2CCNCC2)cc1 | Cl-c1:c:c:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[#7:3](-[C:4])-[C:5]):c:1.N-[C;H0;D3;+0:6](-N)=[S;H0;D1;+0:7]>>[C:4]-[#7:3](-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:6]-[SH;D1;+0:7])-[C:5] | 134.8 | [{"value": 65.0, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 134.8, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 7.6 g of thiourea, 22.9 g of 1-[3-(4-chlorophenyl)propyl]-4-(3-chlorophenyl)piperazine dihydrochloride, 5.8 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 10.0 g of sodium hydroxide in 50 ml of water. Work-up, as described a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Thiourea | Aliphatic thiol | c1ccccc1 | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.Clc1ccc(CCCN2CCN(c3cccc(Cl)c3)CC2)cc1.NC(N)=S>C(C)O.O>Cl.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fb6342854daa4ef9895b1e9cbc8b15ba | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1>>CCCCc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.Cl | C(CCC)C1=CC=C(C=C1)N=C=O.Cl.Cl.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCS.C(C)N(CC)CC>>Cl.Cl.C(CCC)C1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([N:9]=[C:10]=[O:11])[cH:32][cH:33]1.[ClH:34].[SH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][CH2:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[CH2:30][CH2:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10]([O... | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 | CCCCc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCCc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[O;H0;D1;+0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:5](-[OH;D1;+0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | The procedure described in Example 2 was followed, using 2.5 g of 4-n-butylphenyl isocyanate, 5.0 g of 3-{4-[3-(4-chlorophenyl)propyl]piperazin-1-yl}propanethiol dihydrochloride, 1.4 g of triethylamine and 50 ml of methylene chloride, to give 2.7 g (34% of theory) of N-(4-n-butylphenyl-S-{3-[4-[3-(4-chlorophenyl)propyl... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCCCc1ccc(N=C=O)cc1.Cl.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1>C(Cl)Cl>CCCCc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-734f4d7e69b04aab8269e26db78ea339 | ClCCCBr.Fc1ccc(CN2CCNCC2)cc1>>Cl.Cl.Fc1ccc(CN2CCN(CCCCl)CC2)cc1 | FC1=CC=C(CN2CCNCC2)C=C1.[OH-].[K+].BrCCCCl>>Cl.Cl.FC1=CC=C(CN2CCN(CC2)CCCCl)C=C1 | Br[CH2:13][CH2:14][CH2:15][Cl:1].[F:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][NH:12][CH2:17][CH2:18]2)[cH:19][cH:20]1>>[ClH:1].[ClH:2].[F:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1 | ClCCCBr.Fc1ccc(CN2CCNCC2)cc1 | Cl.Cl.Fc1ccc(CN2CCN(CCCCl)CC2)cc1 | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 8bb1dcdfb1ee6ce852f7a1c342bcd4b443f45e43cf7019fdcba041cd9c6ac04f | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 179.2 | [{"value": 61.0, "product": "Cl.Cl.FC1=CC=C(CN2CCN(CC2)CCCCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 179.2, "product": "Cl.Cl.FC1=CC=C(CN2CCN(CC2)CCCCl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(a) was followed, using 32.8 g of 1-(4-fluorobenzyl)piperazine, 30.0 g of potassium hydroxide, 100 ml of dimethyl sulfoxide and 27.0 g of 1-bromo-3-chloropropane. Work-up, as described above, gave 35.2 g (61% of theory) of 1-(4-fluorobenzyl)-4-(3-chloropropyl) piperazine dihydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | Br- | CS(=O)C | null | null | ClCCCBr.Fc1ccc(CN2CCNCC2)cc1>CS(=O)C>Cl.Cl.Fc1ccc(CN2CCN(CCCCl)CC2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fb0f4206c10d4323b2412cb842391736 | ClCCl.ClCCl.Fc1ccc(N2CCN(CCCS)CC2)cc1.O=C=Nc1ccccc1>>Cl.Cl.OC(Nc1ccccc1)=[SH]CCCN1CCN(c2ccc(F)cc2)CC1 | C(Cl)Cl.C1(=CC=CC=C1)N=C=O.FC1=CC=C(C=C1)N1CCN(CC1)CCCS.C(Cl)Cl>>Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)C1=CC=C(C=C1)F | ClC[Cl:1].ClC[Cl:2].[SH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[CH2:27][CH2:28]1.[O:3]=[C:4]=[N:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[ClH:1].[ClH:2].[OH:3][C:4]([NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[SH:12][CH2:13][CH2:14][CH2:15][N:16]... | ClCCl.ClCCl.Fc1ccc(N2CCN(CCCS)CC2)cc1.O=C=Nc1ccccc1 | Cl.Cl.OC(Nc1ccccc1)=[SH]CCCN1CCN(c2ccc(F)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 019a2e24e0358337607bf7b4ba58c5c6f3d418e1be5864dd8ac3426507a76549 | ed477d17b3772485f3bf707e50ec8b6650cdbbfeb5890403e4ee7fb6adb0740e | C(Nc1ccccc1)=[SH]CCCN1CCN(c2ccccc2)CC1 | Cl-C-[Cl;H0;D1;+0:1].Cl-C-[Cl;H0;D1;+0:2].[C:3]-[C:4]-[SH;D1;+0:5].[O;H0;D1;+0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:3]-[C:4]-[SH;D2;+0:5]=[C;H0;D3;+0:7](-[OH;D1;+0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11].[ClH;D0;+0:1].[ClH;D0;+0:2] | 33 | [{"value": 33.0, "product": "Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCCN1CCN(CC1)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.2 g of phenyl isocyanate was added to a solution of 2.5 g of 3-[4-(4-fluorophenyl)piperazin-1-yl]propanethiol in 75 ml of methylene chloride, and the mixture was refluxed for four hours. After the further addition of 100 ml of methylene chloride the solution was washed with water, dried (sodium sulfate) and concentra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary halide.Primary halide.Isocyanate.Aliphatic thiol | Secondary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | ClCCl.ClCCl.Fc1ccc(N2CCN(CCCS)CC2)cc1.O=C=Nc1ccccc1>>Cl.Cl.OC(Nc1ccccc1)=[SH]CCCN1CCN(c2ccc(F)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b5880115943c4665b571bee98c011ee9 | ClCCBr.Clc1ccc(CN2CCNCC2)cc1>>Cl.Cl.ClCCN1CCN(Cc2ccc(Cl)cc2)CC1 | ClC1=CC=C(CN2CCNCC2)C=C1.BrCCCl>>Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCl)C=C1 | Br[CH2:5][CH2:4][Cl:1].[NH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | ClCCBr.Clc1ccc(CN2CCNCC2)cc1 | Cl.Cl.ClCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | O1CCCC1 | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[Cl;D1;H0:10]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1.[ClH;D0;+0:3] | 112 | [{"value": 56.0, "product": "Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 112.0, "product": "Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 15.0 g of 1-(4-chlorobenzyl)piperazine, 14.4 g of 1-bromo-2-chloroethane and 150 ml of tetrahydrofuran was refluxed for 8 hours. The solvent was removed in vacuo, and 2N sodium hydroxide was added to the residue. The product was extracted with methylene chloride, and the extract was dried (sodium sulfate) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | O1CCCC1 | null | null | ClCCBr.Clc1ccc(CN2CCNCC2)cc1>O1CCCC1>Cl.Cl.ClCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a44d77395f1c48f3a29b906d95127ca1 | Cl.ClCCN1CCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S>>Cl.SCCN1CCN(Cc2ccc(Cl)cc2)CC1 | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCl)C=C1>>Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCS)C=C1 | [ClH:2].Cl[CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | Cl.ClCCN1CCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S | Cl.SCCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].N-C(-N)=[S;H0;D1;+0:4]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 97.8 | [{"value": 62.0, "product": "Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCS)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCS)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 6.1 g of thiourea, 13.8 g of 1-(4-chlorobenzyl)-4-(2-chloroethyl)piperazine dihydrochloride, 4.1 g of triethylamine and 150 ml of reagent ethanol. The hydrolysis was effected with 7.0 g of sodium hydroxide and 50 ml of water. Work-up, as described above, gave ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.ClCCN1CCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S>C(C)O.O>Cl.SCCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fcef17e19b204f38a565811b3b58d7ad | O=C=Nc1ccccc1.SCCN1CCN(Cc2ccc(Cl)cc2)CC1>>Cl.Cl.OC(Nc1ccccc1)=[SH]CCN1CCN(Cc2ccc(Cl)cc2)CC1 | C1(=CC=CC=C1)N=C=O.ClC1=CC=C(CN2CCN(CC2)CCS)C=C1>>Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [O:3]=[C:4]=[N:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[Cl:1][c:23]1[cH:22][cH:21][c:20]([CH2:19][N:18]2[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][SH:12])[CH2:28][CH2:27]2)[cH:26][cH:25]1>>[ClH:1].[ClH:2].[OH:3][C:4]([NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[SH:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2... | O=C=Nc1ccccc1.SCCN1CCN(Cc2ccc(Cl)cc2)CC1 | Cl.Cl.OC(Nc1ccccc1)=[SH]CCN1CCN(Cc2ccc(Cl)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 9ddf29a0add694314a86de0a39264129a9713962546a4ec140d50667e08753fd | 126df213390631efc30fe64ae8364e595ba3d5d450128f642d2c5ebbd6a2ca21 | C(Nc1ccccc1)=[SH]CCN1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2]-[SH;D1;+0:3].[Cl;H0;D1;+0:4]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[O;H0;D1;+0:10]=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[C:2]-[SH;D2;+0:3]=[C;H0;D3;+0:11](-[OH;D1;+0:10])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15].[Cl;D1;H0:16]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[ClH;D0;+0:4] | 128.2 | [{"value": 43.0, "product": "Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 128.2, "product": "Cl.Cl.C1(=CC=CC=C1)NC(O)=SCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 35 was followed, using 1.3 g of phenyl isocyanate, 3.0 g of 2-[4-(4-chlorobenzyl)piperazin-1-yl]ethanethiol and 100 ml of methylene chloride, to give 2.2 g (43% of theory) of N-phenyl-S-{2-[4-(4-chlorobenzyl)piperazin-1-yl]ethyl}thiocarbamate dihydrochloride as a white crystalline sol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Aliphatic thiol | Aromatic halide.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | O=C=Nc1ccccc1.SCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>Cl.Cl.OC(Nc1ccccc1)=[SH]CCN1CCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a34cebc025d14918a8b53e7fb7577a4a | O=C=NC1CCCCC1.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>>Cl.Cl.OC(NC1CCCCC1)=[SH]CCCN1CCN(CCc2ccc(Cl)cc2)CC1 | C1(CCCCC1)N=C=O.ClC1=CC=C(CCN2CCN(CC2)CCCS)C=C1>>Cl.Cl.C1(CCCCC1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl | [O:3]=[C:4]=[N:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1.[Cl:1][c:25]1[cH:24][cH:23][c:22]([CH2:21][CH2:20][N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][SH:12])[CH2:30][CH2:29]2)[cH:28][cH:27]1>>[ClH:1].[ClH:2].[OH:3][C:4]([NH:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[SH:12][CH2:13][CH2:14][CH2:1... | O=C=NC1CCCCC1.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1 | Cl.Cl.OC(NC1CCCCC1)=[SH]CCCN1CCN(CCc2ccc(Cl)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 9ddf29a0add694314a86de0a39264129a9713962546a4ec140d50667e08753fd | 126df213390631efc30fe64ae8364e595ba3d5d450128f642d2c5ebbd6a2ca21 | C(NC1CCCCC1)=[SH]CCCN1CCN(CCc2ccccc2)CC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;H0;D1;+0:5])-[C:6].[C:7]-[C:8]-[SH;D1;+0:9].[Cl;H0;D1;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](-[OH;D1;+0:5])=[SH;D2;+0:9]-[C:8]-[C:7])-[C:6].[Cl;D1;H0:16]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[ClH;D0;+0:10] | 170.7 | [{"value": 58.0, "product": "Cl.Cl.C1(CCCCC1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 170.7, "product": "Cl.Cl.C1(CCCCC1)NC(O)=SCCCN1CCN(CC1)CCC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 35 was followed, using 1.7 g of cyclohexyl isocyanate, 4.0 g of 3-[4-(4-chlorophenethyl)piperazin-1-yl]propanethiol and 100 ml of methylene chloride, to give 3.8 g (58% of theory) of N-cyclohexyl-S-{3-[4-(4-chlorophenethyl)piperazin-1-yl]propyl}thiocarbamate dihydrochloride as a white... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Aliphatic thiol | Aromatic halide.Secondary amine | c1ccccc1 | c1ccccc1 | C1CCCCC1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | O=C=NC1CCCCC1.SCCCN1CCN(CCc2ccc(Cl)cc2)CC1>C(Cl)Cl>Cl.Cl.OC(NC1CCCCC1)=[SH]CCCN1CCN(CCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0346a80a37094debaa473c96709fc5a5 | COc1ccc(N=C=O)cc1.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1>>COc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.COc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.Cl.Cl.Cl.Cl.O | COC1=CC=C(C=C1)N=C=O.ClC1=CC=C(C=C1)CCCN1CCN(CC1)CCCS>>O.Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=C(C=C1)Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=C(C=C1)Cl.Cl.Cl | [CH3:1][O:2][c:3]1[cH:31][cH:4][c:6]([N:7]=[C:8]=[O:9])[cH:57][cH:58]1.[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:47][N:48]([CH2:49][CH2:50][CH2:51][c:52]2[cH:27][cH:26][c:24]([Cl:25])[cH:23][cH:53]2)[CH2:59][CH2:60]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([OH:9])=[SH:10][CH2:11][CH2:12][CH2:13][N:14]... | COc1ccc(N=C=O)cc1.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1 | COc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.COc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.Cl.Cl.Cl.Cl.O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 269f1633e2ea877d9658f087c771fdd064531e4fcb63915701a286aa807c71eb | 4615a94198e052f6fbe6c3d4f017aa5c788848cac6fab2700239215f52926247 | C(Nc1ccccc1)=[SH]CCCN1CCN(CCCc2ccccc2)CC1.C(Nc1ccccc1)=[SH]CCCN1CCN(CCCc2ccccc2)CC1 | [C;D1;H3:1]-[#8:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[O;H0;D1;+0:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:1.[Cl;D1;H0:12]-[c:13]1:[c:14]:[cH;D2;+0:15]:[c;H0;D3;+0:16](-[C:17]-[C:18]-[C:19]-[#7:20]2-[C:21]-[CH2;D2;+0:22]-[N;H0;D3;+0:23](-[C:24]-[C:25]-[C:26]-[SH;D1;+0:27])-[C... | 146.1 | [{"value": 48.0, "product": "O.Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=C(C=C1)Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=C(C=C1)Cl.Cl.Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 146.1, "product": "O.Cl.Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1CCN(CC1)CCCC1=CC=C(C=C1)Cl.COC1=CC=C(C=C1)NC(O)=SCCCN1... | null | null | null | null | The procedure described in Example 35 was followed, using 2.0 g of 4-methoxyphenyl isocyanate, 4.0 g of 3-{4-[3-(4-chlorophenyl)propyl]piperazin-1-yl}propanethiol and 100 ml of methylene chlorine to give 3.4 g (48% of theory) of N-(4-methoxyphenyl)-S-{3-[4-[3-(4-chlorophenyl)propyl]piperazin-1-yl]propyl}thiocarbamate d... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Isocyanate.Tertiary amine.Aliphatic thiol | Aromatic halide.Ether.Ether.Secondary amine.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | null | null | null | COc1ccc(N=C=O)cc1.SCCCN1CCN(CCCc2ccc(Cl)cc2)CC1>>COc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.COc1ccc(NC(O)=[SH]CCCN2CCN(CCCc3ccc(Cl)cc3)CC2)cc1.Cl.Cl.Cl.Cl.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b3cce434c6ef4afc85c9dbb95a837744 | CCCCCCN=C=O.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>CCCCCCNC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl | C(CCCCC)N=C=O.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1>>Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[O:9].[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([OH:9])=[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:1... | CCCCCCN=C=O.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | CCCCCCNC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | c1ccc(CN2CCNCC2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;H0;D1;+0:5].[C:6]-[C:7]-[SH;D1;+0:8]>>[C:6]-[C:7]-[SH;D2;+0:8]=[C;H0;D3;+0:4](-[OH;D1;+0:5])-[NH;D2;+0:3]-[C:2]-[C:1] | 157.9 | [{"value": 51.0, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 157.9, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 35 was followed, using 1.4 g of n-hexyl isocyanate, 3.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol and 100 ml of methylene chloride, to give 2.7 g (51% of theory) of N-(n-hexyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}thiocarbamate dihydrochloride as a white crystalli... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCCCCCN=C=O.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CCCCCCNC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3a99d50f95d64431bf061d9f3353a09f | ClCCCBr.Clc1ccc(CCCCN2CCNCC2)cc1>>Cl.Cl.ClCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1 | ClC1=CC=C(C=C1)CCCCN1CCNCC1.BrCCCCl.[OH-].[K+]>>Cl.Cl.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCCl | Br[CH2:6][CH2:5][CH2:4][Cl:1].[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1>>[ClH:1].[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[CH2:... | ClCCCBr.Clc1ccc(CCCCN2CCNCC2)cc1 | Cl.Cl.ClCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1 | null | null | CS(=O)C | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 0403b0fd8876264587fe8aac393e426a627a9dbc8cbe88cf6818c920cd0399bd | a4ff305a4a016f4677b6596bbb229eed668b787eedc9bb50407db4321ec4925c | c1ccc(CCCCN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[Cl;D1;H0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1.[ClH;D0;+0:4] | 125.7 | [{"value": 82.0, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 125.7, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(a) was followed, using 10.0 g of 4-(4-chlorophenyl)butyl piperazine, 47.2 g of 1-bromo-3-chloropropane, 150 ml of dimethyl sulfoxide and 11.2 g of potassium hydroxide, to give 10.0 g (82% of theory) of 1-[4-(4-chlorophenyl)butyl]-4-(3-chloropropyl)piperazine dihydrochloride as a whi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | Primary halide.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | Br- | CS(=O)C | null | null | ClCCCBr.Clc1ccc(CCCCN2CCNCC2)cc1>CS(=O)C>Cl.Cl.ClCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bf5cd469793a4ce49e0abb6aa996f1d7 | Cl.ClCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1.NC(N)=S>>Cl.SCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1 | C(C)O.NC(=S)N.Cl.Cl.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCCl.[OH-].[Na+]>>Cl.Cl.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCS | [ClH:2].Cl[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[... | Cl.ClCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1.NC(N)=S | Cl.SCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CCCCN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 30.2 | [{"value": 16.0, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.2, "product": "Cl.Cl.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 1.0 g of thiourea, 4.0 g of 1-[4-(4-chlorophenyl)butyl]-4-(3-chloropropyl)piperazine dihydrochloride and 50 ml of reagent ethanol. The hydrolysis was effected with 4.0 g of sodium hydroxide in 50 ml of water. Work-up of the free base, as described above follow... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | O | null | null | Cl.ClCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1.NC(N)=S>O>Cl.SCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-79c508329b5d4f1d8bd9e814f1079ea1 | CCCCCCN=C=O.SCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1>>CCCCCCNC(O)=[SH]CCCN1CCN(CCCCc2ccc(Cl)cc2)CC1.Cl.Cl | C(CCCCC)N=C=O.ClC1=CC=C(C=C1)CCCCN1CCN(CC1)CCCS>>Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CCCCC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[O:9].[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][CH2:20][CH2:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([OH:9])=[SH:10][CH2:11][CH2:12][CH2:13][N:... | CCCCCCN=C=O.SCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1 | CCCCCCNC(O)=[SH]CCCN1CCN(CCCCc2ccc(Cl)cc2)CC1.Cl.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | c1ccc(CCCCN2CCNCC2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;H0;D1;+0:5].[C:6]-[C:7]-[SH;D1;+0:8]>>[C:6]-[C:7]-[SH;D2;+0:8]=[C;H0;D3;+0:4](-[OH;D1;+0:5])-[NH;D2;+0:3]-[C:2]-[C:1] | 99.8 | [{"value": 32.0, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CCCCC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CCCCC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.0 g of n-hexyl isocyanate, 2.6 g of 3-{4-[4-(4-chlorophenyl)butyl]piperazin-1-yl}propanethiol and 25 ml of methylene chloride, to give 1.4 g (32% of theory) of N-(n-hexyl)-S-{3-[4-[4-(4-chlorophenyl)butyl]piperazin-1-yl]propyl}thiocarbamate dihydrochloride as a... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCCCCCN=C=O.SCCCN1CCN(CCCCc2ccc(Cl)cc2)CC1>C(Cl)Cl>CCCCCCNC(O)=[SH]CCCN1CCN(CCCCc2ccc(Cl)cc2)CC1.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d30d8a19d77a43a283a0480973ee3168 | BrCC=Cc1ccccc1.Cl.ClCCCN1CCNCC1>>Cl.ClCCCN1CCN(CC=Cc2ccccc2)CC1 | C(C=CC1=CC=CC=C1)Br.O.Cl.Cl.ClCCCN1CCNCC1.ClCCCN1CCNCC1.Cl.Cl.C(C)N(CC)CC>>Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCCl | Br[CH2:11][CH:12]=[CH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]1>>[ClH:2].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH:12]=[CH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1 | BrCC=Cc1ccccc1.Cl.ClCCCN1CCNCC1 | Cl.ClCCCN1CCN(CC=Cc2ccccc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C(=Cc1ccccc1)CN1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]=[C:3]-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:4]-[C:3]=[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | 278.1 | [{"value": 70.0, "product": "Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 278.1, "product": "Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 6.0 g of cinnamyl bromide were added to a mixture of 7.4 g of 1-(3-chloropropyl)piperazine dihydrochloride hemihydrate, 6.1 g of triethylamine and 100 ml of reagent ethanol. The mixture was refluxed for 4 hours and then stirred overnight. After removal of the solvent in vacuo, water was added to the residue. The produc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | C(C)O | null | 8 | BrCC=Cc1ccccc1.Cl.ClCCCN1CCNCC1>C(C)O>Cl.ClCCCN1CCN(CC=Cc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c7de0e9fa1d24e82a534bc829b4771d1 | Cl.ClCCCN1CCN(CC=Cc2ccccc2)CC1.NC(N)=S>>Cl.SCCCN1CCN(CC=Cc2ccccc2)CC1 | NC(=S)N.[OH-].[Na+].C(C)N(CC)CC.Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCCl>>Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCS | [ClH:2].Cl[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH:12]=[CH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1.NC(N)=[S:3]>>[ClH:2].[SH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:11][CH:12]=[CH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1 | Cl.ClCCCN1CCN(CC=Cc2ccccc2)CC1.NC(N)=S | Cl.SCCCN1CCN(CC=Cc2ccccc2)CC1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | C(=Cc1ccccc1)CN1CCNCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 52 | [{"value": 52.0, "product": "Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 1(b) was followed, using 3.1 g of thiourea, 7.4 g of 1-cinnamyl-4-(3-chloropropyl)piperazine dihydrochloride, 4,1 g of triethylamine and 100 ml of reagent ethanol. The hydrolysis was effected with 3.0 g of sodium hydroxide in 30 ml of water. Work-up, as described above, gave 3.6 g (52... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C(C)O.O | null | null | Cl.ClCCCN1CCN(CC=Cc2ccccc2)CC1.NC(N)=S>C(C)O.O>Cl.SCCCN1CCN(CC=Cc2ccccc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ed77c6d5e9bf4296bf37b6996aa0f6d8 | CCCCCCN=C=O.Cl.SCCCN1CCN(CC=Cc2ccccc2)CC1>>CCCCCCNC(O)=[SH]CCCN1CCN(CC=Cc2ccccc2)CC1.Cl | C(CCCCC)N=C=O.Cl.Cl.C(C=CC1=CC=CC=C1)N1CCN(CC1)CCCS.C(C)N(CC)CC>>Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CC=CC1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[O:9].[ClH:30].[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([OH:9])=[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2... | CCCCCCN=C=O.Cl.SCCCN1CCN(CC=Cc2ccccc2)CC1 | CCCCCCNC(O)=[SH]CCCN1CCN(CC=Cc2ccccc2)CC1.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | C(=Cc1ccccc1)CN1CCNCC1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;H0;D1;+0:5].[C:6]-[C:7]-[SH;D1;+0:8]>>[C:6]-[C:7]-[SH;D2;+0:8]=[C;H0;D3;+0:4](-[OH;D1;+0:5])-[NH;D2;+0:3]-[C:2]-[C:1] | 64.2 | [{"value": 31.0, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CC=CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.2, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CC1)CC=CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 0.4 g of n-hexyl isocyanate, 1.0 g of 3-(4-cinnamylpiperazin-1-yl)propanethiol dihydrochloride, 0.6 g of triethylamine and 50 ml of methylene chloride, to give 0.44 g (31% of theory) of N-(n-hexyl)-S-[3-(4-cinnamylpiperazin-1-yl)propyl]thiocarbamate dihydrochlori... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CCCCCCN=C=O.Cl.SCCCN1CCN(CC=Cc2ccccc2)CC1>C(Cl)Cl>CCCCCCNC(O)=[SH]CCCN1CCN(CC=Cc2ccccc2)CC1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0956ad0caa5041f28456e5e148238e1e | ClCCCBr.Clc1ccc(CN2CCCNCC2)cc1>>ClCCCN1CCCN(Cc2ccc(Cl)cc2)CC1 | BrCCCCl.ClC1=CC=C(CN2CCNCCC2)C=C1.[OH-].[K+]>>ClC1=CC=C(CN2CCN(CCC2)CCCCl)C=C1 | Br[CH2:4][CH2:3][CH2:2][Cl:1].[NH:5]1[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | ClCCCBr.Clc1ccc(CN2CCCNCC2)cc1 | ClCCCN1CCCN(Cc2ccc(Cl)cc2)CC1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | a53bdae9df4a04e07ad93d60984a5afd70715f5d49f2f60eb64dc34064ff0da2 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[#7:4]-[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:8]-[C:9] | 42 | [{"value": 42.0, "product": "ClC1=CC=C(CN2CCN(CCC2)CCCCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.8, "product": "ClC1=CC=C(CN2CCN(CCC2)CCCCl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 15.7 g of 1-bromo-3-chloropropane were added to a cooled solution of 15.0 g of 1-(4-chlorobenzyl)homopiperazine and 12.0 g of potassium hydroxide in 50 ml of dimethyl sulfoxide. The mixture was stirred at 5°-10° C. for one hour, and then an additional 30 minutes at room temperature. After the addition of ice water, the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]C1 | C1C[NH]CC[NH]C1 | C1C[NH]CC[NH]C1.c1ccccc1 | HBr | CS(=O)C | null | 1 | ClCCCBr.Clc1ccc(CN2CCCNCC2)cc1>CS(=O)C>ClCCCN1CCCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-73e545c91cc447a8af0c692a3811aa45 | ClCCCN1CCCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S>>SCCCN1CCCN(Cc2ccc(Cl)cc2)CC1 | [OH-].[Na+].NC(=S)N.ClC1=CC=C(CN2CCN(CCC2)CCCCl)C=C1.C(C)O>>ClC1=CC=C(CN2CCN(CCC2)CCCS)C=C1 | Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1.NC(N)=[S:1]>>[SH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | ClCCCN1CCCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S | SCCCN1CCCN(Cc2ccc(Cl)cc2)CC1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccc(CN2CCCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].N-C(-N)=[S;H0;D1;+0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[SH;D1;+0:4] | 39.1 | [{"value": 39.0, "product": "ClC1=CC=C(CN2CCN(CCC2)CCCS)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.1, "product": "ClC1=CC=C(CN2CCN(CCC2)CCCS)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4.1 g of thiourea were added to a mixture of 8.0 g of 1-(4-chlorobenzyl)-4-(3-chloropropyl)homopiperazine and 100 ml of reagent ethanol. The mixture was refluxed for 6 hours and then stirred overnight at room temperature. A solution of 5.0 g of sodium hydroxide in 30 ml of water was added, and the resulting solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | C1C[NH]CC[NH]C1.c1ccccc1 | HCl | O | null | 8 | ClCCCN1CCCN(Cc2ccc(Cl)cc2)CC1.NC(N)=S>O>SCCCN1CCCN(Cc2ccc(Cl)cc2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-111c8594f1d44a3f8495a7a4086c6573 | CCCCCCN=C=O.SCCCN1CCCN(Cc2ccc(Cl)cc2)CC1>>CCCCCCNC(O)=[SH]CCCN1CCCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl | C(CCCCC)N=C=O.ClC1=CC=C(CN2CCN(CCC2)CCCS)C=C1>>Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CCC1)CC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[O:9].[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([OH:9])=[SH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2... | CCCCCCN=C=O.SCCCN1CCCN(Cc2ccc(Cl)cc2)CC1 | CCCCCCNC(O)=[SH]CCCN1CCCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d231144fa8916ec255ee403916a9da3c3f1c5088a3508df700953f4bb7ee4232 | 975aa459e325ce46eb7c0448bba281ba869acd2dcf1407dbdcac2da9a164e0c9 | c1ccc(CN2CCCNCC2)cc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;H0;D1;+0:5].[C:6]-[C:7]-[SH;D1;+0:8]>>[C:6]-[C:7]-[SH;D2;+0:8]=[C;H0;D3;+0:4](-[OH;D1;+0:5])-[NH;D2;+0:3]-[C:2]-[C:1] | 77.6 | [{"value": 33.0, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CCC1)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "Cl.Cl.C(CCCCC)NC(O)=SCCCN1CCN(CCC1)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Example 2 was followed, using 1.3 g of n-hexyl isocyanate, 3.0 g of 3-[4-(4-chlorobenzyl)homopiperazin-1-yl]propanethiol and 75 ml of methylene chloride, to give 1.3 g (33% of theory) of N-(n-hexyl)-S-{3-[4-(4-chlorobenzyl)homopiperazin-1-yl]propyl}thiocarbamate dihydrochloride as a tan powde... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aliphatic thiol | Secondary amine | null | null | C1C[NH]CC[NH]C1.c1ccccc1 | null | C(Cl)Cl | null | null | CCCCCCN=C=O.SCCCN1CCCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CCCCCCNC(O)=[SH]CCCN1CCCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5a4a048975d74124980c61747a711e76 | CC(C)(C)N=C=O.CCN(CC)CC.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>>CC(C)(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.CC(C)(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl.Cl.O.O.O | C(C)(C)(C)N=C=O.Cl.Cl.ClC1=CC=C(CN2CCN(CC2)CCCS)C=C1.C(C)N(CC)CC>>O.Cl.Cl.C(C)(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl.O.O.C(C)(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl.Cl.Cl | [CH3:1][C:2]([CH3:3])([N:5]=[C:6]=[O:7])[CH3:44].[CH3:4][CH2:36][N:15]([CH2:16][CH3:17])[CH2:34][CH3:35].[ClH:46].[SH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:39][N:40]([CH2:41][c:42]2[cH:18][cH:19][c:20]([Cl:21])[cH:47][cH:48]2)[CH2:24][CH2:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6]([OH:7])=[SH:8][CH2:9][CH2:... | CC(C)(C)N=C=O.CCN(CC)CC.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1 | CC(C)(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.CC(C)(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl.Cl.O.O.O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 170d291efa68874c42c5544601aab6c0edfcfd06ec7e7a4139e7efdccfe2cde2 | 4d3b6a868bf49165ce96d9965938fb5717fddaeab7e13b62dac1602bc9e82d12 | c1ccc(CN2CCNCC2)cc1.c1ccc(CN2CCNCC2)cc1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH3;D1;+0:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;H0;D1;+0:7].[CH3;D1;+0:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:11]-[CH3;D1;+0:12])-[CH2;D2;+0:13]-[CH3;D1;+0:14].[Cl;D1;H0:15]-[c;H0;D3;+0:16]1:[c:17]:[cH;D2;+0:18]:[c;H0;D3;+0:19](-[C:20]-[N;H0;D3;+0:21]2-[CH2;D2;+0:22]-[C:23]-[#7:2... | 140.2 | [{"value": 60.0, "product": "O.Cl.Cl.C(C)(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl.O.O.C(C)(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl.Cl.Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 140.2, "product": "O.Cl.Cl.C(C)(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C=C1)Cl.O.O.C(C)(C)(C)NC(O)=SCCCN1CCN(CC1)CC1=CC=C(C... | null | null | null | null | The procedure described in Example 2 was followed, using 0.8 g of t-butyl isocyanate, 3.0 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride, 1.6 g of triethylamine and 75 ml of methylene chloride, to give 2.2 g (60% of theory) of N-(t-butyl)-S-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}thiocarbamat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Tertiary amine.Tertiary amine.Aliphatic thiol | Aromatic halide.Aromatic halide.Secondary amine.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)(C)N=C=O.CCN(CC)CC.Cl.SCCCN1CCN(Cc2ccc(Cl)cc2)CC1>C(Cl)Cl>CC(C)(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.CC(C)(C)NC(O)=[SH]CCCN1CCN(Cc2ccc(Cl)cc2)CC1.Cl.Cl.Cl.O.O.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e5f252377ae24090a434bf5416e54651 | COc1cc(SC)ccc1C(=O)O.Nc1cn[nH]c(=O)c1N>>COc1cc(SC)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | COC1=C(C(=O)O)C=CC(=C1)SC.NC=1C(NN=CC1N)=O>>COC1=C(C=CC(=C1)SC)C=1N=C2C(=CNNC2=O)N1 | O=[C:11](O)[c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9]1.[NH2:12][c:13]1[cH:14][n:15][nH:16][c:17](=[O:18])[c:19]1[NH2:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9][c:10]1-[c:11]1[n:12][c:13]2[cH:14][nH:15][nH:16][c:17](=[O:18])[c:19]-2[n:20]1 | COc1cc(SC)ccc1C(=O)O.Nc1cn[nH]c(=O)c1N | COc1cc(SC)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 96109e218d24fb14479892243bf7b2a5f05e386416ab27902ec0f9172e3e4a04 | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | O=c1[nH][nH]cc2nc(-c3ccccc3)nc1-2 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[NH2;D1;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[n;H0;D2;+0:11]:[#7;a:12]:[c:13](=[O;D1;H0:14]):[c;H0;D3;+0:15]:1-[NH2;D1;+0:16]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9]2:[c:10]:[nH;D2;+0:11]:[#7;a:12]:[c:13](=[O;D1;H... | null | [] | 50 | CELSIUS | null | null | Two grams of 2-methoxy-4-methylmercapto-benzoic acid are suspended in 20 ml of polyphosphoric acid, and 1.2 gm of 4,5-diamino-2H-pyridazin-3-one are added thereto with stirring at 50° C. The mixture is heated for 90 minutes to 100°-110° C. and then poured onto ice water, and the product which is precipitated on stirrin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccnnc1 | c1nc2cnncc2[nH]1 | c1ccccc1.c1nc2cnncc2[nH]1 | HO- | null | 50 | null | COc1cc(SC)ccc1C(=O)O.Nc1cn[nH]c(=O)c1N>>COc1cc(SC)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-11a5b9119d9941618a2c6738f74ed215 | COc1cc(SC)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.OO>>COc1cc(S(C)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | COC1=C(C=CC(=C1)SC)C=1N=C2C(=CNNC2=O)N1.OO>>COC1=C(C=CC(=C1)S(=O)C)C=1N=C2C(=CNNC2=O)N1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][CH3:7])[cH:9][cH:10][c:11]1-[c:12]1[n:13][c:14]2[cH:15][nH:16][nH:17][c:18](=[O:19])[c:20]-2[n:21]1.O[OH:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1-[c:12]1[n:13][c:14]2[cH:15][nH:16][nH:17][c:18](=[O:19])[c:20]-2[n:21]1 | COc1cc(SC)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.OO | COc1cc(S(C)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | null | null | C(C)(=O)O | Oxidation | Sulfanyl to sulfinyl_H2O2 | 3f94fa67dce0f9d1622f25c2f6b679e0a2528e6d5c5559b15aed37456745a4b5 | 099322fb111e24ec324e6fad75d493a762ca0cd5af0df8c6f3bfd25c910b45a8 | O=c1[nH][nH]cc2nc(-c3ccccc3)nc1-2 | O-[OH;D1;+0:1].[C;D1;H3:2]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 24 | HOUR | An amount of 0.21 gm of 2-(2-methoxy-4-methylmercapto-phenyl)-5H-imidazo[4,5-d]pyridazin-4-one is suspended in 10 ml of glacial acetic acid and mixed with 0.08 ml of 30% hydrogen peroxide. The mixture is stirred for 24 hours at ambient temperature and poured onto 20 ml of ice water. It is then stirred until a precipita... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfoxide | null | null | c1ccccc1.c1nc2cnncc2[nH]1 | HO- | C(C)(=O)O | null | 24 | COc1cc(SC)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.OO>C(C)(=O)O>COc1cc(S(C)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-033061a22a0d4381887b3730bf5da3c7 | COc1cc(S(C)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.OO>>COc1cc(S(C)(=O)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | COC1=C(C=CC(=C1)S(=O)C)C=1N=C2C(=CNNC2=O)N1.OO.OO>>COC1=C(C=CC(=C1)S(=O)(=O)C)C=1N=C2C(=CNNC2=O)N1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([S:6]([CH3:7])=[O:8])[cH:10][cH:11][c:12]1-[c:13]1[n:14][c:15]2[cH:16][nH:17][nH:18][c:19](=[O:20])[c:21]-2[n:22]1.O[OH:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6]([CH3:7])(=[O:8])=[O:9])[cH:10][cH:11][c:12]1-[c:13]1[n:14][c:15]2[cH:16][nH:17][nH:18][c:19](=[O:20])[c:21]-2[n:22]1 | COc1cc(S(C)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.OO | COc1cc(S(C)(=O)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | null | null | C(C)(=O)O | Oxidation | OtherReaction | 82eeb432cea55e49dd1e612c513601ecda8b69f66d62f31cabaae14486674ab1 | cbb05648c84536652b4eef951a389695d3f3bef8ba19ea253e8a66fff9ee4d44 | O=c1[nH][nH]cc2nc(-c3ccccc3)nc1-2 | O-[OH;D1;+0:1].[C;D1;H3:2]-[S;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;H0;D1;+0:1])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 55 | MINUTE | A quantity of 0.07 gm of 2-(2-methoxy-4-methylsulfinyl-phenyl)-5H-imidazo[4,5-d]pyridazin-4-one is dissolved in 5 ml of glacial acetic acid, mixed with 0.05 ml of 30% hydrogen peroxide, and stirred first for 55 minutes at ambient temperature then for two hours at 40°-50° C., Then, a further 0.05 ml of hydrogen peroxide... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Sulfoxide | Sulfone | null | null | c1ccccc1.c1nc2cnncc2[nH]1 | HO- | C(C)(=O)O | null | 0.916667 | COc1cc(S(C)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.OO>C(C)(=O)O>COc1cc(S(C)(=O)=O)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ed32d25e0c7c45dfb2b09ee2c01e0cd2 | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)O.COc1ccc(N)c(N)n1>>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2N(C)C)c(N)n1 | N.CN(C1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-])C.Cl.Cl.NC1=NC(=CC=C1N)OC.O>>CN(C1=C(C(=O)NC=2C(=NC(=CC2)OC)N)C=CC(=C1)[N+](=O)[O-])C | O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]1[N:19]([CH3:20])[CH3:21].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:22]([NH2:23])[n:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]2[N:19]([CH3:20])[CH3:21])... | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)O.COc1ccc(N)c(N)n1 | COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2N(C)C)c(N)n1 | null | null | P(=O)(Cl)(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccnc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[N;D1;H2:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | null | [] | null | null | null | null | An amount of 1.05 gm of 2-dimethylamino-4-nitro-benzoic acid is suspended in 35 ml of phosphorus oxychloride, and 1.05 gm of 2,3-diamino-6-methoxy-pyridine dihydrochloride are added thereto. The mixture is refluxed for 5 minutes, left to cool for 15 minutes with stirring, and finally decomposed with water. The solution... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)O.COc1ccc(N)c(N)n1>P(=O)(Cl)(Cl)Cl>COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2N(C)C)c(N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-072da412b7c74d68ae2b0cbe80cf9367 | COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2N(C)C)c(N)n1>>COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1 | CN(C1=C(C(=O)NC=2C(=NC(=CC2)OC)N)C=CC(=C1)[N+](=O)[O-])C>>CN(C1=C(C=CC(=C1)[N+](=O)[O-])C=1NC=2C(=NC(=CC2)OC)N1)C | O=[C:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:23][c:22]1[NH2:21])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]1[N:18]([CH3:19])[CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]3[N:18]([CH3:19])[CH3:20])[n:21][c:22]2[n:2... | COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2N(C)C)c(N)n1 | COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1 | null | null | P(=O)(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | e4e19e3354cf9a80f944e2a2a196231b02ba3b66651d07863abe72917fd317c6 | a079090652d9d6c0e17c70eeab94f6d7afea064f52cf5fa9036d5feedd14143a | c1ccc(-c2nc3ncccc3[nH]2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[#7;a:7]:[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[#7:13]):[c:14]>>[#7:13]-[c:12](:[c:14]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c:5](:[#7;a:7]:[c:8]):[c:3](:[c:4]):[nH;D2;+0:2]:1):[c:10]:[c:11] | null | [] | null | null | null | null | A suspension of 1.4 gm of 3-[(2-dimethylamino-4-nitro-benzoyl)-amino]-2-amino-6-methoxy-pyridine in 40 ml of phosphorus oxychloride is refluxed for three hours. The phosphorus oxychloride is evaporated off by about two-thirds, and the residue is poured into water. The solution obtained is made ammoniacal, and the produ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | null | c1ccncc1 | c1cnc2nc[nH]c2c1 | c1cnc2nc[nH]c2c1.c1ccccc1 | HO- | P(=O)(Cl)(Cl)Cl | null | null | COc1ccc(NC(=O)c2ccc([N+](=O)[O-])cc2N(C)C)c(N)n1>P(=O)(Cl)(Cl)Cl>COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2a7e3c04034f4962805f2b8605f567fe | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)O.COc1ccc(N)c(N)n1>>COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1 | CN(C1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-])C.Cl.Cl.NC1=NC(=CC=C1N)OC>>CN(C1=C(C=CC(=C1)[N+](=O)[O-])C=1NC=2C(=NC(=CC2)OC)N1)C | O=[C:8](O)[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]1[N:18]([CH3:19])[CH3:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:22]([NH2:21])[n:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]3[N:18]([CH3:19])[CH3:20])[n:21][c:22]... | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)O.COc1ccc(N)c(N)n1 | COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1 | null | null | P(=O)(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 732e0ce9e0b11ff0dfc685a4702602ca2b8a50d1240d37c421f2ec2dce5e88c1 | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc(-c2nc3ncccc3[nH]2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#7:6]):[c:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[#7:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c:9](:[#7;a:10]:[c:11]):[c:12](:[c:14]):[nH;D2;+0:13]:1):[c:3]:[c:4] | null | [] | null | null | null | null | An amount of 0.45 gm of 2-dimethylamino-4-nitro-benzoic acid is suspended in 15 ml of phosphorus oxychloride, and 0.45 gm of 2,3-diamino-6-methoxy-pyridine dihydrochloride are added. The mixture is refluxed for two hours and after cooling poured onto water. The aqueous solution is made ammoniacal with cooling, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccncc1 | c1cnc2nc[nH]c2c1 | c1cnc2nc[nH]c2c1.c1ccccc1 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)O.COc1ccc(N)c(N)n1>P(=O)(Cl)(Cl)Cl>COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-32e3d902264f4bcabd1c60500c9ad7ca | COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1>>CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=CCC(=O)NC2=N1 | CN(C1=C(C=CC(=C1)[N+](=O)[O-])C=1NC=2C(=NC(=CC2)OC)N1)C.Cl>>CN(C1=C(C=CC(=C1)[N+](=O)[O-])C1=NC=2C(NC(CC2)=O)=N1)C | C[O:19][c:18]1[cH:17][cH:16][c:15]2[nH:14][c:13](-[c:12]3[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]3)[n:22][c:21]2[n:20]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[C:13]1=[N:14][C:15]2=[CH:16][CH2:17][C:18](=[O:19])[NH:20][C:21]2=[N:22]1 | COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1 | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=CCC(=O)NC2=N1 | null | null | null | Reduction | OtherReaction | 1d9952418bd03299fc209d71ff471e1f9e7efb202810a53a913ea8369ea77e1f | 2aeb8b29862491232763337fc29cdbaeebf7c7f0fe8fc7b3a932e164064ec89c | O=C1CC=C2N=C(c3ccccc3)N=C2N1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5]2:[nH;D2;+0:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#7:12]):[c:13]):[n;H0;D2;+0:14]:[c;H0;D3;+0:15]:2:[n;H0;D2;+0:16]:1>>[#7:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[C;H0;D3;+0:7]1=[N;H0;D2;+0:6]-[C;H0;D3;+0:5]2=[CH;D2;+0:4]-[CH2;D2;... | null | [] | null | null | null | null | A quantity of 0.2 gm of 2-(2-dimethylamino-4-nitro-phenyl)-5-methoxy-imidazo[4,5-b]pyridine is heated in a bomb tube to 100° C. for three hours with 5 ml of concentrated hydrochloric acid. The reaction mixture is poured onto about 20 ml of ice, neutralized, and extracted with ethyl acetate. After washing with water and... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary amide | c1cnc2nc[nH]c2c1 | C1=NC2=CCCNC2=N1 | c1ccccc1.C1=NC2=CCCNC2=N1 | Other | null | null | null | COc1ccc2[nH]c(-c3ccc([N+](=O)[O-])cc3N(C)C)nc2n1>>CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=CCC(=O)NC2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-635cfe2f33674766827bc3eaf4c9f1ef | COc1cc(SC)ccc1C(=O)Nc1[nH]c(=O)ccc1[N+](=O)[O-]>>COc1cc(SC)ccc1C1=NC2=CCC(=O)NC2=N1 | COC1=C(C(=O)NC=2NC(C=CC2[N+](=O)[O-])=O)C=CC(=C1)SC>>COC1=C(C=CC(=C1)SC)C1=NC=2C(NC(CC2)=O)=N1 | O=[C:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9]1)[NH:12][c:13]1[nH:18][c:16](=[O:17])[cH:15][cH:14][c:19]1[N+:20](=O)[O-]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9][c:10]1[C:11]1=[N:12][C:13]2=[CH:14][CH2:15][C:16](=[O:17])[NH:18][C:19]2=[N:20]1 | COc1cc(SC)ccc1C(=O)Nc1[nH]c(=O)ccc1[N+](=O)[O-] | COc1cc(SC)ccc1C1=NC2=CCC(=O)NC2=N1 | null | [Pd] | C(C)(=O)O.[H][H] | Functional Group Interconversion | OtherReaction | 097fc0ee2c46913ac4696174b943d22ba6c02de85f4d1e046db3addb5981cdbd | 5165cb7328f1a36fd7fbe60c5a38f86cf63e94d5d06f686e3ec068783b31cb00 | O=C1CC=C2N=C(c3ccccc3)N=C2N1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c;H0;D3;+0:5](=[O;D1;H0:6]):[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9]:1-[N+;H0;D3:10](=O)-[O-])-[c:11](:[c:12]):[c:13]>>[O;D1;H0:6]=[C;H0;D3;+0:5]1-[CH2;D2;+0:7]-[CH;D2;+0:8]=[C;H0;D3;+0:3]2-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[c:11](:[c:12]):[c:13])-[N;H0;D2;+0:10... | null | [] | null | null | null | null | An amount of 6.2 gm of 2-[(2-methoxy-4-methylmercapto-benzoyl)-amino]-3-nitro-1H-pyridin-6-one is dissolved in 370 ml of glacial acetic acid and hydrogenated with hydrogen in the presence of 6 gm of 10% palladium charcoal at ambient temperature under 5 bars of pressure (duration of reaction: two hours). The catalyst is... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Secondary amide | Secondary amide | c1cnccc1 | C1=NC2=CCCNC2=N1 | c1ccccc1.C1=NC2=CCCNC2=N1 | Other | [Pd].C(C)(=O)O.[H][H] | null | null | COc1cc(SC)ccc1C(=O)Nc1[nH]c(=O)ccc1[N+](=O)[O-]>[Pd].C(C)(=O)O.[H][H]>COc1cc(SC)ccc1C1=NC2=CCC(=O)NC2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-eed20875f89042a78eaca70db7681c77 | COc1ccc(-c2nc3c(ccc[n+]3[O-])[nH]2)c(OC)c1>>COc1ccc(C2=NC3=CCC(=O)NC3=N2)c(OC)c1 | O.COC1=C(C=CC(=C1)OC)C=1NC=2C(=[N+](C=CC2)[O-])N1.Cl>>COC1=C(C=CC(=C1)OC)C1=NC=2C(NC(CC2)=O)=N1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[nH:8][c:9]3[cH:10][cH:11][cH:12][n+:14]([O-:13])[c:15]3[n:16]2)[c:17]([O:18][CH3:19])[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[N:8][C:9]3=[CH:10][CH2:11][C:12](=[O:13])[NH:14][C:15]3=[N:16]2)[c:17]([O:18][CH3:19])[cH:20]1 | COc1ccc(-c2nc3c(ccc[n+]3[O-])[nH]2)c(OC)c1 | COc1ccc(C2=NC3=CCC(=O)NC3=N2)c(OC)c1 | null | null | C(C)(=O)OC(C)=O | Reduction | OtherReaction | f2c2fc23baa26f196552837bc874de3c071e518b7de1f37d2a5ae017bb507d87 | 0bc6e593e557e498d898fea24a080f55573b56d80aeb59ee40dc96af16ebee15 | O=C1CC=C2N=C(c3ccccc3)N=C2N1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:7]2:[c;H0;D3;+0:8](:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[n+;H0;D3:12]:2-[O-;H0;D1:13]):[nH;D2;+0:14]:1):[c:15]:[c:16]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D3;+0:5]1=[N;H0;D2;+0:14]-[C;H0;D3;+0:8]2=[CH;D2;+0:9]-[CH2;D2;+0:10]-[C;... | null | [] | 120 | CELSIUS | 30 | MINUTE | Four grams of 2-(2,4-dimethoxy-phenyl)-imidazo[4,5-b]pyridin-4-oxide is suspended in 40 ml of acetic anhydride and refluxed for 2.75 hours. After cooling the mixture is poured onto 150 ml of ice, 25 ml of 6N hydrochloric acid are added, and the mixture is stirred at 120° C. for 30 minutes. It is cooled to ambient tempe... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amide | C1=C[NH+]=c2nc[nH]c2=C1 | C1=NC2=CCCNC2=N1 | c1ccccc1.C1=NC2=CCCNC2=N1 | null | C(C)(=O)OC(C)=O | 120 | 0.5 | COc1ccc(-c2nc3c(ccc[n+]3[O-])[nH]2)c(OC)c1>C(C)(=O)OC(C)=O>COc1ccc(C2=NC3=CCC(=O)NC3=N2)c(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ef123c04d995491aa3822ca7748bf055 | CC(=O)O.COc1ccc(-c2nc3ncnc(Cl)c3[nH]2)c(OC)c1>>COc1ccc(-c2nc3nc[nH]c(=O)c3[nH]2)c(OC)c1 | COC1=C(C=CC(=C1)OC)C1=NC2=NC=NC(=C2N1)Cl.C(C)(=O)O>>COC1=C(C=CC(=C1)OC)C1=NC=2N=CNC(C2N1)=O | CC(O)=[O:14].Cl[c:13]1[n:12][cH:11][n:10][c:9]2[n:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][c:17]3[O:18][CH3:19])[nH:16][c:15]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[n:10][cH:11][nH:12][c:13](=[O:14])[c:15]3[nH:16]2)[c:17]([O:18][CH3:19])[cH:20]1 | CC(=O)O.COc1ccc(-c2nc3ncnc(Cl)c3[nH]2)c(OC)c1 | COc1ccc(-c2nc3nc[nH]c(=O)c3[nH]2)c(OC)c1 | null | null | [OH-].[Na+] | Miscellaneous | OtherReaction | 9377ccc63c37898d5c04b2c0b12e6c58f02a4daaf315adef4f55845fc1e74f96 | 3fbb180061815c1a91daf750f59d95354663c01e4c6076719644d5369bdccd52 | O=c1[nH]cnc2nc(-c3ccccc3)[nH]c12 | C-C(-O)=[O;H0;D1;+0:1].Cl-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1 | null | [] | null | null | null | null | One-half gram of 8-(2,4-dimethoxy-phenyl)-6-chloro-purine is refluxed for seven hours in 30 ml of 2N sodium hydroxide solution. The mixture is acidified with glacial acetic acid, and the precipitate obtained is recrystallized from methanol.
Conditions: See reaction.notes.procedure_details.
Workup: the precipitate obtai... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid | null | c1ncc2nc[nH]c2n1 | c1nc2cncnc2[nH]1 | c1ccccc1.c1nc2cncnc2[nH]1 | HCl | [OH-].[Na+] | null | null | CC(=O)O.COc1ccc(-c2nc3ncnc(Cl)c3[nH]2)c(OC)c1>[OH-].[Na+]>COc1ccc(-c2nc3nc[nH]c(=O)c3[nH]2)c(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1710e5d8571f49e99991ce847c7586f7 | COc1ccc(SC)cc1-c1nc2ncnc(Cl)c2[nH]1.[OH-]>>COc1ccc(SC)cc1C1=NC2=NC=NC(=O)C2=N1 | ClC1=C2NC(=NC2=NC=N1)C1=C(C=CC(=C1)SC)OC.[OH-].[K+]>>COC1=C(C=C(C=C1)SC)C1=NC2=NC=NC(C2=N1)=O | Cl[c:17]1[n:16][cH:15][n:14][c:13]2[n:12][c:11](-[c:10]3[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([S:7][CH3:8])[cH:9]3)[nH:20][c:19]21.[OH-:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7][CH3:8])[cH:9][c:10]1[C:11]1=[N:12][C:13]2=[N:14][CH:15]=[N:16][C:17](=[O:18])[C:19]2=[N:20]1 | COc1ccc(SC)cc1-c1nc2ncnc(Cl)c2[nH]1.[OH-] | COc1ccc(SC)cc1C1=NC2=NC=NC(=O)C2=N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 327533abca4f49f12126eb122dcca5190e8fa70809992fbb7584ad35f80bddab | 91d49c9e42f397efc3bc857ca7ed897b28f3c235ee6bb61b057a5ee9eee70a95 | O=C1N=CN=C2N=C(c3ccccc3)N=C12 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5]2:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#8:12]):[c:13]):[nH;D2;+0:14]:[c;H0;D3;+0:15]:2:1.[OH-;D0:16]>>[#8:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[C;H0;D3;+0:7]1=[N;H0;D2;+0:6]-[C;H0;D3;+0:5]2=[N;H0;D2;+0:4]-[CH;D2;... | null | [] | null | null | null | null | Prepared analogously to Example 16 from 6-chloro-8-(2-methoxy-5-methylmercapto-phenyl)-purine by reaction with 20% potassium hydroxide solution.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Substituted imine | c1ncc2nc[nH]c2n1 | C1=NCC2=NC=NC2=N1 | c1ccccc1.C1=NCC2=NC=NC2=N1 | HCl | null | null | null | COc1ccc(SC)cc1-c1nc2ncnc(Cl)c2[nH]1.[OH-]>>COc1ccc(SC)cc1C1=NC2=NC=NC(=O)C2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2a4c687c874b41f689e1af3834786261 | COc1cc(OC)c(-c2nc3ncnc(Cl)c3[nH]2)cc1Br.[OH-]>>COc1cc(OC)c(C2=NC3=NC=NC(=O)C3=N2)cc1Br | ClC1=C2NC(=NC2=NC=N1)C1=C(C=C(C(=C1)Br)OC)OC.[OH-].[K+]>>BrC=1C(=CC(=C(C1)C1=NC2=NC=NC(C2=N1)=O)OC)OC | Cl[c:15]1[n:14][cH:13][n:12][c:11]2[n:10][c:9](-[c:8]3[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:20]([Br:21])[cH:19]3)[nH:18][c:17]21.[OH-:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([C:9]2=[N:10][C:11]3=[N:12][CH:13]=[N:14][C:15](=[O:16])[C:17]3=[N:18]2)[cH:19][c:20]1[Br:21] | COc1cc(OC)c(-c2nc3ncnc(Cl)c3[nH]2)cc1Br.[OH-] | COc1cc(OC)c(C2=NC3=NC=NC(=O)C3=N2)cc1Br | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 327533abca4f49f12126eb122dcca5190e8fa70809992fbb7584ad35f80bddab | 91d49c9e42f397efc3bc857ca7ed897b28f3c235ee6bb61b057a5ee9eee70a95 | O=C1N=CN=C2N=C(c3ccccc3)N=C12 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5]2:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#8:12]):[c:13]):[nH;D2;+0:14]:[c;H0;D3;+0:15]:2:1.[OH-;D0:16]>>[#8:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[C;H0;D3;+0:7]1=[N;H0;D2;+0:6]-[C;H0;D3;+0:5]2=[N;H0;D2;+0:4]-[CH;D2;... | null | [] | null | null | null | null | Prepared analogously to Example 16 from 6-chloro-8-(5-bromo-2,4-dimethoxy-phenyl)-purine by reaction with 20% potassium hydroxide solution.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Substituted imine | c1ncc2nc[nH]c2n1 | C1=NCC2=NC=NC2=N1 | c1ccccc1.C1=NCC2=NC=NC2=N1 | HCl | null | null | null | COc1cc(OC)c(-c2nc3ncnc(Cl)c3[nH]2)cc1Br.[OH-]>>COc1cc(OC)c(C2=NC3=NC=NC(=O)C3=N2)cc1Br |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5e0c07233f644f10933c6296392a0863 | CNS(=O)(=O)c1cc(-c2nc(Cl)c3[nH]cnc3n2)c(OC)cc1Cl>>CNS(=O)c1cc(C2=NC3=NC=NC(=O)C3=N2)c(OC)cc1Cl | ClC1=C2NC=NC2=NC(=N1)C1=C(C=C(C(=C1)S(=O)(=O)NC)Cl)OC.[OH-].[K+]>>ClC1=CC(=C(C=C1S(=O)NC)C1=NC2=NC=NC(C2=N1)=O)OC | Cl[c:14]1[c:16]2[c:10]([n:9][c:8](-[c:7]3[cH:6][c:5]([S:3]([NH:2][CH3:1])(=[O:4])=[O:15])[c:22]([Cl:23])[cH:21][c:18]3[O:19][CH3:20])[n:17]1)[n:11][cH:12][nH:13]2>>[CH3:1][NH:2][S:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]2=[N:9][C:10]3=[N:11][CH:12]=[N:13][C:14](=[O:15])[C:16]3=[N:17]2)[c:18]([O:19][CH3:20])[cH:21][c:22]1[Cl:2... | CNS(=O)(=O)c1cc(-c2nc(Cl)c3[nH]cnc3n2)c(OC)cc1Cl | CNS(=O)c1cc(C2=NC3=NC=NC(=O)C3=N2)c(OC)cc1Cl | null | null | null | Reduction | OtherReaction | 3e4cf9df2c9f742f263371e855ee29cdf6de22aa47b48f9d571faca5570cf50b | 8cd35126ae40bb2bce2484e3c67bcf4ba838ff3c539e79634188717dbe42a6b6 | O=C1N=CN=C2N=C(c3ccccc3)N=C12 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[c:5]:[c:6](-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;H0;D1;+0:9])-[#7:10]-[C;D1;H3:11]):[c:12]:[c:13]:[c:14]:2-[#8:15]):[n;H0;D2;+0:16]:[c;H0;D3;+0:17]2:[n;H0;D2;+0:18]:[cH;D2;+0:19]:[nH;D2;+0:20]:[c;H0;D3;+0:21]:2:1>>[#8:15]-[c:14]1:[c:13]:[c:12]:[c:6](-[S;H0;... | null | [] | null | null | null | null | Prepared analogously to Example 16 from 6-chloro-(4-chloro-2-methoxy-5-methylaminosulfonyl-phenyl)-purine with 20% potassium hydroxide solution.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Substituted imine | c1ncc2nc[nH]c2n1 | C1=NCC2=NC=NC2=N1 | c1ccccc1.C1=NCC2=NC=NC2=N1 | HCl | null | null | null | CNS(=O)(=O)c1cc(-c2nc(Cl)c3[nH]cnc3n2)c(OC)cc1Cl>>CNS(=O)c1cc(C2=NC3=NC=NC(=O)C3=N2)c(OC)cc1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bb53e3adbf81433d844364e852ee7c9c | COc1cc(SC)ccc1C(=O)O.Nc1[nH]c(=O)[nH]c(=O)c1N>>COc1cc(SC)ccc1C(=O)Nc1c(N)[nH]c(=O)[nH]c1=O | O.COC1=C(C(=O)O)C=CC(=C1)SC.NC=1NC(NC(C1N)=O)=O>>NC=1NC(NC(C1NC(C1=C(C=C(C=C1)SC)OC)=O)=O)=O | O[C:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9]1)=[O:12].[NH2:13][c:14]1[c:15]([NH2:16])[nH:17][c:18](=[O:19])[nH:20][c:21]1=[O:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9][c:10]1[C:11](=[O:12])[NH:13][c:14]1[c:15]([NH2:16])[nH:17][c:18](=[O:19])[nH:20][c:21]1=[O:22] | COc1cc(SC)ccc1C(=O)O.Nc1[nH]c(=O)[nH]c(=O)c1N | COc1cc(SC)ccc1C(=O)Nc1c(N)[nH]c(=O)[nH]c1=O | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1c[nH]c(=O)[nH]c1=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11](=[O;D1;H0:12]):[c:13]:1-[NH2;D1;+0:14]>>[N;D1;H2:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11](=[O;D1;H0:12]):[c:13]:1-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | Twenty grams of 2-methoxy-4-methylmercapto-benzoic acid is dissolved in 260 ml of dimethylformamide, mixed with 13 gm of N,N'-carbonyl-diimidazole, and stirred for 30 minutes at ambient temperature. Then, 13 gm of 4,5-diamino-pyrimidin-2,6-dione are added, and the reaction mixture is refluxed for three hours with stirr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cncnc1 | HO- | CN(C=O)C | null | 0.5 | COc1cc(SC)ccc1C(=O)O.Nc1[nH]c(=O)[nH]c(=O)c1N>CN(C=O)C>COc1cc(SC)ccc1C(=O)Nc1c(N)[nH]c(=O)[nH]c1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-88ccc828c8c445c7842b8cfe8e1ea814 | COc1cc(SC)ccc1C(=O)Nc1c(N)[nH]c(=O)[nH]c1=O>>COc1cc(SC)ccc1C1=NC2=NC(=O)NC(=O)C2=N1 | NC=1NC(NC(C1NC(C1=C(C=C(C=C1)SC)OC)=O)=O)=O.[OH-].[Na+]>>COC1=C(C=CC(=C1)SC)C1=NC2=NC(NC(C2=N1)=O)=O | O=[C:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9]1)[NH:21][c:20]1[c:13]([NH2:12])[nH:14][c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6][CH3:7])[cH:8][cH:9][c:10]1[C:11]1=[N:12][C:13]2=[N:14][C:15](=[O:16])[NH:17][C:18](=[O:19])[C:20]2=[N:21]1 | COc1cc(SC)ccc1C(=O)Nc1c(N)[nH]c(=O)[nH]c1=O | COc1cc(SC)ccc1C1=NC2=NC(=O)NC(=O)C2=N1 | null | null | C(C)O | Oxidation | OtherReaction | f19b00b783c8668bdd897adbf9f0a492f75ec8ff374f905495560e889f5ad6dd | 8094e487c6679f2b9c623ceccf688ef9bd51c882e09a5e50b6df3f985c6c390b | O=C1N=C2N=C(c3ccccc3)N=C2C(=O)N1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:4](-[NH2;D1;+0:5]):[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[nH;D2;+0:9]:[c;H0;D3;+0:10]:1=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[N;H0;D2;+0:6]=[C;H0;D3;+0:4]2-[N;H0;D2;+0:5]=[C;H0;D3;+0:1](-[c:12](:[c:13]):[c:14])-[N;H0;D2;+0:2]=[C... | null | [] | null | null | 15 | MINUTE | Two grams of 4-amino-5-(2-methoxy-4-methylmercapto-benzoylamino)-pyrimidin-2,6-dione are refluxed for 21 hours with 50 ml of ethanol and 50 ml of 2N sodium hydroxide solution. After about 15 minutes, a solution is formed. After cooling, the solution is suction filtered with glacial acetic acid, washed with water, and d... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Substituted imine.Unsubstituted dicarboximide | c1cncnc1 | C1=NC2=NCNCC2=N1 | c1ccccc1.C1=NC2=NCNCC2=N1 | HO- | C(C)O | null | 0.25 | COc1cc(SC)ccc1C(=O)Nc1c(N)[nH]c(=O)[nH]c1=O>C(C)O>COc1cc(SC)ccc1C1=NC2=NC(=O)NC(=O)C2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cd16ce517d74444e9c3738b0eac46728 | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)Nc1nc[nH]c(=O)c1N>>CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=NC=NC(=O)C2=N1 | NC1=C(N=CNC1=O)NC(C1=C(C=C(C=C1)[N+](=O)[O-])N(C)C)=O>>CN(C1=C(C=CC(=C1)[N+](=O)[O-])C1=NC2=NC=NC(C2=N1)=O)C | O=[C:13]([c:12]1[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[NH:14][c:15]1[n:16][cH:17][nH:18][c:19](=[O:20])[c:21]1[NH2:22]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[C:13]1=[N:14][C:15]2=[N:16][CH:17]=[N:18][C:19](=[O:20])[C:21]2=[N:22]1 | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)Nc1nc[nH]c(=O)c1N | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=NC=NC(=O)C2=N1 | null | null | C(C)(=O)O | Oxidation | OtherReaction | d1086c143044236faf9cf27747cb243342e0b462dafd8d56bc6d7c348e0f7406 | 1a44b30fbd9836f37983c1becc2bcb0cab0f1034333aa4a97c7d041f13ef2d97 | O=C1N=CN=C2N=C(c3ccccc3)N=C12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[c;H0;D3;+0:9]:1-[NH2;D1;+0:10])-[c:11](:[c:12]):[c:13]>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[N;H0;D2;+0:6]=[CH;D2;+0:5]-[N;H0;D2;+0:4]=[C;H0;D3;+0:3]2-[N;H0;D2;+0:2]=[C;H0;D3;+0:1](-[c:11](:[c:12]):[c:13])-[N;H... | null | [] | null | null | null | null | One gram of 5-amino-4-(2-dimethylamino-4-nitro-benzoylamino)pyrimidin-6-one is refluxed for two hours in 50 ml of glacial acetic acid. The mixture is evaporated to dryness, and the residue is stirred out with ethanol in the warm.
Conditions: See reaction.notes.procedure_details.
Workup: The mixture is evaporated to dry... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Substituted imine | c1cncnc1 | C1=NCC2=NC=NC2=N1 | c1ccccc1.C1=NCC2=NC=NC2=N1 | HO- | C(C)(=O)O | null | null | CN(C)c1cc([N+](=O)[O-])ccc1C(=O)Nc1nc[nH]c(=O)c1N>C(C)(=O)O>CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=NC=NC(=O)C2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7272044c980b48afb3322c501ec35ccc | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=NC=NC(=O)C2=N1>>CN(C)c1cc(N)ccc1C1=NC2=NC=NC(=O)C2=N1 | CN(C1=C(C=CC(=C1)[N+](=O)[O-])C1=NC2=NC=NC(C2=N1)=O)C.[H][H]>>NC1=CC(=C(C=C1)C1=NC2=NC=NC(C2=N1)=O)N(C)C | O=[N+:7]([O-])[c:6]1[cH:5][c:4]([N:2]([CH3:1])[CH3:3])[c:10]([C:11]2=[N:12][C:13]3=[N:14][CH:15]=[N:16][C:17](=[O:18])[C:19]3=[N:20]2)[cH:9][cH:8]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:8][cH:9][c:10]1[C:11]1=[N:12][C:13]2=[N:14][CH:15]=[N:16][C:17](=[O:18])[C:19]2=[N:20]1 | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=NC=NC(=O)C2=N1 | CN(C)c1cc(N)ccc1C1=NC2=NC=NC(=O)C2=N1 | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1N=CN=C2N=C(c3ccccc3)N=C12 | 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 | An amount of 0.9 gm of 8-(2-dimethylamino-4-nitro-phenyl)purin-6-one is hydrogenated in 50 ml of methanol in the presence of 0.5 gm of Raney nickel at ambient temperature and under 5 bars of pressure with hydrogen for three hours until the calculated quantity has been taken up. After the catalyst has been subjected to ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1=NCC2=NC=NC2=N1 | Other | [Ni].CO | null | null | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=NC=NC(=O)C2=N1>[Ni].CO>CN(C)c1cc(N)ccc1C1=NC2=NC=NC(=O)C2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-639397261a4c4c98b76a12db25b2c876 | CC(=O)OC(C)=O.CN(C)c1cc(N)ccc1C1=NC2=NC=NC(=O)C2=N1>>CC(=O)Nc1ccc(C2=NC3=NC=NC(=O)C3=N2)c(N(C)C)c1 | NC1=CC(=C(C=C1)C1=NC2=NC=NC(C2=N1)=O)N(C)C.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC(=C(C=C1)C1=NC2=NC=NC(C2=N1)=O)N(C)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]2=[N:10][C:11]3=[N:12][CH:13]=[N:14][C:15](=[O:16])[C:17]3=[N:18]2)[c:19]([N:20]([CH3:21])[CH3:22])[cH:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([C:9]2=[N:10][C:11]3=[N:12][CH:13]=[N:14][C:15](=[O:16])[C:17]3=[N:18]2)[c:19]([N:20]([CH3:21])[C... | CC(=O)OC(C)=O.CN(C)c1cc(N)ccc1C1=NC2=NC=NC(=O)C2=N1 | CC(=O)Nc1ccc(C2=NC3=NC=NC(=O)C3=N2)c(N(C)C)c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C1N=CN=C2N=C(c3ccccc3)N=C12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A quantity of 0.6 gm of 8-(4-amino-2-dimethylamino-phenyl)purin-6-one is heated to 150° C. in 5 ml of acetic anhydride for one hour. The mixture is evaporated to dryness in vacuo and recrystallized from acetone/ether.
Conditions: See reaction.notes.procedure_details.
Workup: The mixture is evaporated to dryness in vacu... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1=NCC2=NC=NC2=N1 | HO- | null | null | null | CC(=O)OC(C)=O.CN(C)c1cc(N)ccc1C1=NC2=NC=NC(=O)C2=N1>>CC(=O)Nc1ccc(C2=NC3=NC=NC(=O)C3=N2)c(N(C)C)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7c71ace40aec4481bedb5ae26a19e76f | COc1cc(OCc2ccccc2)ccc1-c1nc2ncnc(Cl)c2[nH]1.[OH-]>>COc1cc(OCc2ccccc2)ccc1C1=NC2=NC=NC(=O)C2=N1 | C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C1=NC2=NC=NC(=C2N1)Cl)OC.[OH-].[K+]>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C1=NC2=NC=NC(C2=N1)=O)OC | Cl[c:23]1[n:22][cH:21][n:20][c:19]2[n:18][c:17](-[c:16]3[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH2:7][c:8]4[cH:9][cH:10][cH:11][cH:12][cH:13]4)[cH:14][cH:15]3)[nH:26][c:25]21.[OH-:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[C:17]1=[N:18][C:19]2=[N:20][CH:... | COc1cc(OCc2ccccc2)ccc1-c1nc2ncnc(Cl)c2[nH]1.[OH-] | COc1cc(OCc2ccccc2)ccc1C1=NC2=NC=NC(=O)C2=N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 327533abca4f49f12126eb122dcca5190e8fa70809992fbb7584ad35f80bddab | 91d49c9e42f397efc3bc857ca7ed897b28f3c235ee6bb61b057a5ee9eee70a95 | O=C1N=CN=C2N=C(c3ccc(OCc4ccccc4)cc3)N=C12 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5]2:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#8:12]):[c:13]):[nH;D2;+0:14]:[c;H0;D3;+0:15]:2:1.[OH-;D0:16]>>[#8:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[C;H0;D3;+0:7]1=[N;H0;D2;+0:6]-[C;H0;D3;+0:5]2=[N;H0;D2;+0:4]-[CH;D2;... | null | [] | null | null | null | null | Prepared analogously to Example 16 from 8-(4-benzyloxy-2-methoxy-phenyl)-6-chloro-purine by reaction with 40% potassium hydroxide solution.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Substituted imine | c1ncc2nc[nH]c2n1 | C1=NCC2=NC=NC2=N1 | c1ccccc1.c1ccccc1.C1=NCC2=NC=NC2=N1 | HCl | null | null | null | COc1cc(OCc2ccccc2)ccc1-c1nc2ncnc(Cl)c2[nH]1.[OH-]>>COc1cc(OCc2ccccc2)ccc1C1=NC2=NC=NC(=O)C2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9bb33ecc109041f0a8377bc723501737 | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=CCC(=O)NC2=N1>>CN(C)c1cc(N)ccc1C1=NC2=CCC(=O)NC2=N1 | O.CN(C1=C(C=CC(=C1)[N+](=O)[O-])C1=NC=2C(NC(CC2)=O)=N1)C.[H][H].Cl>>Cl.CN(C1=C(C=CC(=C1)N)C1=NC=2C(NC(CC2)=O)=N1)C | O=[N+:7]([O-])[c:6]1[cH:5][c:4]([N:2]([CH3:1])[CH3:3])[c:10]([C:11]2=[N:12][C:13]3=[CH:14][CH2:15][C:16](=[O:17])[NH:18][C:19]3=[N:20]2)[cH:9][cH:8]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:8][cH:9][c:10]1[C:11]1=[N:12][C:13]2=[CH:14][CH2:15][C:16](=[O:17])[NH:18][C:19]2=[N:20]1 | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=CCC(=O)NC2=N1 | CN(C)c1cc(N)ccc1C1=NC2=CCC(=O)NC2=N1 | null | [Pd] | CN(C=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1CC=C2N=C(c3ccccc3)N=C2N1 | 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 | An amount of 1.7 gm of 2-(2-dimethylamino-4-nitro-phenyl)-4H-imidazo[4,5-b]pyridin-5-one is dissolved in 20 ml of dimethylformamide and mixed with 0.2 gm of 10% palladium/charcoal. The mixture is hydrogenated for three hours with hydrogen at ambient temperature under 5 bars of pressure. The mixture is filtered off from... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1=NC2=CCCNC2=N1 | Other | [Pd].CN(C=O)C | null | null | CN(C)c1cc([N+](=O)[O-])ccc1C1=NC2=CCC(=O)NC2=N1>[Pd].CN(C=O)C>CN(C)c1cc(N)ccc1C1=NC2=CCC(=O)NC2=N1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f2c701250f51434a8eabd6294b537cef | CC(=O)OC(C)=O.CN(C)c1cc(N)ccc1C1=NC2=NC(=O)C=CC2=N1>>CC(=O)Nc1ccc(C2=NC3=CCC(=O)NC3=N2)c(N(C)C)c1 | CN(C1=C(C=CC(=C1)N)C=1N=C2C(=NC(C=C2)=O)N1)C.C(C)(=O)OC(C)=O>>CN(C1=C(C=CC(=C1)NC(=O)C)C1=NC=2C(NC(CC2)=O)=N1)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]2=[N:18][C:17]3=[N:16][C:14](=[O:15])[CH:13]=[CH:12][C:11]3=[N:10]2)[c:19]([N:20]([CH3:21])[CH3:22])[cH:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([C:9]2=[N:10][C:11]3=[CH:12][CH2:13][C:14](=[O:15])[NH:16][C:17]3=[N:18]2)[c:19]([N:20]([CH3:21]... | CC(=O)OC(C)=O.CN(C)c1cc(N)ccc1C1=NC2=NC(=O)C=CC2=N1 | CC(=O)Nc1ccc(C2=NC3=CCC(=O)NC3=N2)c(N(C)C)c1 | null | null | null | Acylation | OtherReaction | 51e2bda446ba4c8c5a1d914db33e90c108810c5753ada7e402d7668ec0fabb8f | 4268bb9edae8244adfa3b7b9a65f5aaf238c4d88c54c190675bc60f475d85d78 | O=C1CC=C2N=C(c3ccccc3)N=C2N1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[c:8](-[C;H0;D3;+0:9]2=[N;H0;D2;+0:10]-[C;H0;D3;+0:11]3=[N;H0;D2;+0:12]-[C:13](=[O;D1;H0:14])-[CH;D2;+0:15]=[CH;D2;+0:16]-[C;H0;D3;+0:17]-3=[N;H0;D2;+0:18]-2):[c:19]:[c:20]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5]1... | null | [] | null | null | null | null | A quantity of 0.6 gm of 2-(2-dimethylamino-4-amino-phenyl)imidazo[4,5-b]pyridin-5-one is refluxed with 20 ml of acetic anhydride for 30 minutes. After evaporation, 10 ml of concentrated ammnoia and then 20 ml of ice are added. The product precipitated is suction filtered and washed with water.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Substituted imine.Primary amine | Secondary amide.Secondary amide | C1=CC2=NC=NC2=NC1 | C1=NC2=CCCNC2=N1 | c1ccccc1.C1=NC2=CCCNC2=N1 | HO- | null | null | null | CC(=O)OC(C)=O.CN(C)c1cc(N)ccc1C1=NC2=NC(=O)C=CC2=N1>>CC(=O)Nc1ccc(C2=NC3=CCC(=O)NC3=N2)c(N(C)C)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1cb12684952945bc8c6d959e38d194f3 | COc1cc(OCc2ccccc2)ccc1C(=O)O.Nc1cnc(Cl)nc1N>>COc1cc(OCc2ccccc2)ccc1-c1nc2nc(Cl)ncc2[nH]1 | ClC1=NC=C(C(=N1)N)N.COC1=C(C(=O)O)C=CC(=C1)OCC1=CC=CC=C1>>COC1=C(C=CC(=C1)OCC1=CC=CC=C1)C1=NC2=NC(=NC=C2N1)Cl | O=[C:17](O)[c:16]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1.[NH2:18][c:19]1[n:20][c:21]([Cl:22])[n:23][cH:24][c:25]1[NH2:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1-[c:17]1[n:18][c:19]2[n:20][c:... | COc1cc(OCc2ccccc2)ccc1C(=O)O.Nc1cnc(Cl)nc1N | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(Cl)ncc2[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e7e72999864bfebc9719cc1ba22dd1cfcb4276023277f918059872106fb5d875 | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc(COc2ccc(-c3nc4ncncc4[nH]3)cc2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[NH2;D1;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1-[NH2;D1;+0:15]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c:9]2:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:2:[nH;D2;+0:15]:1):[c:3]:[c:4] | null | [] | null | null | null | null | Prepared analogously to Example 5 from 2-chloro-4,5-diaminopyrimidine and 2-methoxy-4-benzyloxy benzoic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1cncnc1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | null | null | null | COc1cc(OCc2ccccc2)ccc1C(=O)O.Nc1cnc(Cl)nc1N>>COc1cc(OCc2ccccc2)ccc1-c1nc2nc(Cl)ncc2[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-18a6059416844248a8ba411c923fd244 | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(Cl)ncc2[nH]1.[OH-]>>COc1cc(OCc2ccccc2)ccc1-c1nc2nc(OCc3ccccc3)ncc2[nH]1 | [OH-].[K+].COC1=C(C=CC(=C1)OCC1=CC=CC=C1)C1=NC2=NC(=NC=C2N1)Cl>>COC1=C(C=CC(=C1)OCC1=CC=CC=C1)C1=NC2=NC(=NC=C2N1)OCC1=CC=CC=C1 | Cl[c:21]1[n:20][c:19]2[n:18][c:17](-[c:16]3[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH2:7][c:8]4[cH:9][cH:10][cH:11][cH:12][cH:13]4)[cH:14][cH:15]3)[nH:33][c:32]2[cH:31][n:30]1.[OH-:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1-[c:17]1[n:18][c:19]2[n:20][c:21... | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(Cl)ncc2[nH]1.[OH-] | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(OCc3ccccc3)ncc2[nH]1 | null | null | C(C1=CC=CC=C1)O | Aromatic Heterocycle Formation | OtherReaction | 03a5998335ffb596af27d8aab0922ef9f1874f8bb28364cc91b165295431030a | a4840aa8bdfd6f728c7dfa6c00c462c0316cfea6c6529f068981467c19c289cb | c1ccc(COc2ccc(-c3nc4nc(OCc5ccccc5)ncc4[nH]3)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[#7;a:6]):[c:7]:[#7;a:8]:1.[OH-;D0:9]>>[#7;a:4]:[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[C:10]-[c:11]):[#7;a:8]:[c:7]:[c:5]:1:[#7;a:6] | null | [] | 150 | CELSIUS | null | null | An amount of 4.5 gm of powdered potassium hydroxide is dissolved in 70 ml of benzyl alcohol, and then 7.2 gm of 8-(2-methoxy-4-benzyloxy-phenyl)-2-chloro-purine are added. The mixture is heated to 150° C. for three hours, cooled, and filtered, the filtrate is mixed with ether, and the precipitate obtained is purified b... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1 | null | C(C1=CC=CC=C1)O | 150 | null | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(Cl)ncc2[nH]1.[OH-]>C(C1=CC=CC=C1)O>COc1cc(OCc2ccccc2)ccc1-c1nc2nc(OCc3ccccc3)ncc2[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-31404deb6e244db4997f5de822a83ec7 | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(OCc3ccccc3)ncc2[nH]1>>COc1cc(O)ccc1-c1nc2[nH]c(=O)ncc2[nH]1 | O.[OH-].[Na+].COC1=C(C=CC(=C1)OCC1=CC=CC=C1)C1=NC2=NC(=NC=C2N1)OCC1=CC=CC=C1.[H][H]>>COC1=C(C=CC(=C1)O)C1=NC=2NC(N=CC2N1)=O | c1ccc(C[O:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:9](-[c:10]3[n:11][c:12]4[n:13][c:14]([O:15]Cc5ccccc5)[n:16][cH:17][c:18]4[nH:19]3)[cH:8][cH:7]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[cH:7][cH:8][c:9]1-[c:10]1[n:11][c:12]2[nH:13][c:14](=[O:15])[n:16][cH:17][c:18]2[nH:19]1 | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(OCc3ccccc3)ncc2[nH]1 | COc1cc(O)ccc1-c1nc2[nH]c(=O)ncc2[nH]1 | null | [Pd] | C(C)O | Miscellaneous | OtherReaction | 1f81964fd141b4682692af25f8f498cdff8427eef37d8c7223b62fbb154873cd | 97b700253a515732e056bebfec7d29d55492867916f45a12199b66c78e6a3460 | O=c1ncc2[nH]c(-c3ccccc3)nc2[nH]1 | C(-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[n;H0;D2;+0:10]:1)-c1:c:c:c:c:c:1.[c:11]:[c:12](-[O;H0;D2;+0:13]-C-c1:c:c:c:c:c:1):[c:14]>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[nH;D2;+0:10]:1.[OH;D1;+0:13]-[c:12](:[c:11]):[c:14] | null | [] | null | null | null | null | Three grams of 8-(2-methoxy-4-benzyloxy-phenyl)-2-benzyloxypurine are dissolved in 100 ml of ethanol and hydrogenated in the presence of 1 gm of 20% palladium/charcoal for two hours at 50° C. with hydrogen at 5 bar. The catalyst is filtered off and washed with hot ethanol. The filtrates are evaporated, and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | Other | [Pd].C(C)O | null | null | COc1cc(OCc2ccccc2)ccc1-c1nc2nc(OCc3ccccc3)ncc2[nH]1>[Pd].C(C)O>COc1cc(O)ccc1-c1nc2[nH]c(=O)ncc2[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f3d5d152d9a34241b654d7e6361c94bd | COc1ccc2[nH]c(-c3cc([N+](=O)[O-])c(N4C(=O)c5cc([N+](=O)[O-])ccc5C(C)(C)C4=O)cc3OC)nc2n1>>COc1ccc2[nH]c(-c3cc([N+](=O)[O-])c(N)cc3OC)nc2n1 | COC1=C(C=C(C(=C1)N1C(C2=CC(=CC=C2C(C1=O)(C)C)[N+](=O)[O-])=O)[N+](=O)[O-])C=1NC=2C(=NC(=CC2)OC)N1.O.NN>>COC1=C(C=C(C(=C1)N)[N+](=O)[O-])C=1NC=2C(=NC(=CC2)OC)N1 | CC1(C)C(=O)[N:16]([c:15]2[c:11]([N+:12](=[O:13])[O-:14])[cH:10][c:9](-[c:8]3[nH:7][c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[n:23][c:22]4[n:21]3)[c:18]([O:19][CH3:20])[cH:17]2)C(=O)c2cc([N+](=O)[O-])ccc21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](-[c:9]3[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([NH2:16])[cH:17][c:... | COc1ccc2[nH]c(-c3cc([N+](=O)[O-])c(N4C(=O)c5cc([N+](=O)[O-])ccc5C(C)(C)C4=O)cc3OC)nc2n1 | COc1ccc2[nH]c(-c3cc([N+](=O)[O-])c(N)cc3OC)nc2n1 | null | null | C(C)(C)O | Reduction | OtherReaction | be2562881ed0428f65a7738b6bdfc3bb79b65abb4fb65b1370a2b2057af1cfc1 | b30a79a18555d000c53b56d2dc755cec2380a4d4f2c61e07cb571d58c9e343b2 | c1ccc(-c2nc3ncccc3[nH]2)cc1 | C-C1(-C)-C(=O)-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-C(=O)-c2:c:c(-[N+](=O)-[O-]):c:c:c:2-1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | One half gram of 2-[2-methoxy-5-nitro-4-(4,4-dimethyl-7-nitro-2H,4H-isoquinolin-1,3-dione-2-yl)-phenyl]-5-methoxy-imidazo[4,5-b]pyridine is suspended in 10 ml of isopropanol, mixed with 0.5 ml of 80% hydrazine hydrate, and refluxed for 1.75 hours with stirring. The reaction mixture is concentrated by evaporation, the r... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide.Nitro group | Primary amine | c1ccc2c(c1)CC[NH]C2 | null | c1cnc2nc[nH]c2c1.c1ccccc1 | HO- | C(C)(C)O | null | null | COc1ccc2[nH]c(-c3cc([N+](=O)[O-])c(N4C(=O)c5cc([N+](=O)[O-])ccc5C(C)(C)C4=O)cc3OC)nc2n1>C(C)(C)O>COc1ccc2[nH]c(-c3cc([N+](=O)[O-])c(N)cc3OC)nc2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ac149cd0f9424d489ae8f7b30a738b68 | COc1cc(N)ccc1C(=O)O.Nc1cn[nH]c(=O)c1N>>COc1cc(N)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | NC=1C(NN=CC1N)=O.COC1=C(C(=O)O)C=CC(=C1)N>>COC1=C(C=CC(=C1)N)C=1N=C2C(=CNNC2=O)N1 | O=[C:10](O)[c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([NH2:6])[cH:7][cH:8]1.[NH2:11][c:12]1[cH:13][n:14][nH:15][c:16](=[O:17])[c:18]1[NH2:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:7][cH:8][c:9]1-[c:10]1[n:11][c:12]2[cH:13][nH:14][nH:15][c:16](=[O:17])[c:18]-2[n:19]1 | COc1cc(N)ccc1C(=O)O.Nc1cn[nH]c(=O)c1N | COc1cc(N)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 96109e218d24fb14479892243bf7b2a5f05e386416ab27902ec0f9172e3e4a04 | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | O=c1[nH][nH]cc2nc(-c3ccccc3)nc1-2 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[NH2;D1;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[n;H0;D2;+0:11]:[#7;a:12]:[c:13](=[O;D1;H0:14]):[c;H0;D3;+0:15]:1-[NH2;D1;+0:16]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9]2:[c:10]:[nH;D2;+0:11]:[#7;a:12]:[c:13](=[O;D1;H... | null | [] | null | null | null | null | Prepared analogously to Example 1 from 4,5-diamino-2H-pyridazin-3-one and 2-methoxy-4-amino-benzoic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccnnc1 | c1nc2cnncc2[nH]1 | c1ccccc1.c1nc2cnncc2[nH]1 | HO- | null | null | null | COc1cc(N)ccc1C(=O)O.Nc1cn[nH]c(=O)c1N>>COc1cc(N)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-42289bdb3bd249a6a417937c8b9e169e | CCCOc1cc(SC)ccc1C(=O)O.COc1ccc(N)c(N)n1>>CCCOc1cc(SC)ccc1-c1nc2nc(OC)ccc2[nH]1 | Cl.Cl.NC1=NC(=CC=C1N)OC.C(CC)OC1=C(C(=O)O)C=CC(=C1)SC>>Cl.C(CC)OC1=C(C=CC(=C1)SC)C=1NC=2C(=NC(=CC2)OC)N1 | O=[C:13](O)[c:12]1[c:5]([O:4][CH2:3][CH2:2][CH3:1])[cH:6][c:7]([S:8][CH3:9])[cH:10][cH:11]1.[NH2:14][c:15]1[n:16][c:17]([O:18][CH3:19])[cH:20][cH:21][c:22]1[NH2:23]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7]([S:8][CH3:9])[cH:10][cH:11][c:12]1-[c:13]1[n:14][c:15]2[n:16][c:17]([O:18][CH3:19])[cH:20][cH:21][c:22]2[nH:23... | CCCOc1cc(SC)ccc1C(=O)O.COc1ccc(N)c(N)n1 | CCCOc1cc(SC)ccc1-c1nc2nc(OC)ccc2[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | a9a94f4ec3c76aeed619fd0cb32af4fac024911d5bce22bc3a860e6b5d9190bc | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc(-c2nc3ncccc3[nH]2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c:9](:[#7;a:10]:[c:11]):[c:12](:[c:14]):[nH;D2;+0:13]:1):[c:3]:[c:4] | null | [] | null | null | null | null | Prepared analogously to Example 5 from 2,3-diamino-6-methoxypyridine dihydrochloride and 2-propoxy-4-methylmercapto-benzoic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccncc1 | c1cnc2[nH]cnc2c1 | c1ccccc1.c1cnc2[nH]cnc2c1 | HO- | null | null | null | CCCOc1cc(SC)ccc1C(=O)O.COc1ccc(N)c(N)n1>>CCCOc1cc(SC)ccc1-c1nc2nc(OC)ccc2[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8c990ec368674a9a9a4163d3dd8c972f | COc1cc(N)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.Cl>>COc1cc(Cl)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | COC1=C(C=CC(=C1)N)C=1N=C2C(=CNNC2=O)N1.N(=O)[O-].[Na+].Cl>>COC1=C(C=CC(=C1)Cl)C=1N=C2C(=CNNC2=O)N1 | N[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:9](-[c:10]2[n:11][c:12]3[cH:13][nH:14][nH:15][c:16](=[O:17])[c:18]-3[n:19]2)[cH:8][cH:7]1.[ClH:6]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1-[c:10]1[n:11][c:12]2[cH:13][nH:14][nH:15][c:16](=[O:17])[c:18]-2[n:19]1 | COc1cc(N)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.Cl | COc1cc(Cl)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | null | null | O | Miscellaneous | OtherReaction | 976fb3f0996203ccf639edc3dd63ebf792dabe502fe07eb66206f5ee630d746b | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | O=c1[nH][nH]cc2nc(-c3ccccc3)nc1-2 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 40 | MINUTE | An amount of 1.05 gm of 2-(2-methoxy-4-amino-phenyl)-5H-imidazo[4,5-d]pyridazin-4-one is suspended in 20 ml of 6N hydrochloric acid. The suspension is cooled to 0° to -3° C., and 0.28 gm of sodium nitrite, dissolved in 2 ml of water, are added dropwise thereto. The mixture is stirred for a further 40 minutes and then h... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1nc2cnncc2[nH]1 | Other | O | null | 0.666667 | COc1cc(N)ccc1-c1nc2c[nH][nH]c(=O)c-2n1.Cl>O>COc1cc(Cl)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c7a439da589547019f39681016779e11 | COc1cc(C#N)ccc1-c1nc2[nH]c(=O)ncc2[nH]1.O=S(=O)(O)O>>COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)ncc2[nH]1 | COC1=C(C=CC(=C1)C#N)C1=NC=2NC(N=CC2N1)=O.S(O)(O)(=O)=O>>COC1=C(C=CC(=C1)C(=O)N)C1=NC=2NC(N=CC2N1)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:9][cH:10][c:11]1-[c:12]1[n:13][c:14]2[nH:15][c:16](=[O:17])[n:18][cH:19][c:20]2[nH:21]1.O=S(=O)(O)[OH:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([NH2:7])=[O:8])[cH:9][cH:10][c:11]1-[c:12]1[n:13][c:14]2[nH:15][c:16](=[O:17])[n:18][cH:19][c:20]2[nH:21]1 | COc1cc(C#N)ccc1-c1nc2[nH]c(=O)ncc2[nH]1.O=S(=O)(O)O | COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)ncc2[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | O=c1ncc2[nH]c(-c3ccccc3)nc2[nH]1 | O-S(=O)(=O)-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Prepared by partial saponification of 8-(2-methoxy-4-cyanophenyl)-3H-purin-2-one with concentrated sulfuric acid at ambient temperature.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccccc1.c1ncc2nc[nH]c2n1 | Other | null | null | null | COc1cc(C#N)ccc1-c1nc2[nH]c(=O)ncc2[nH]1.O=S(=O)(O)O>>COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)ncc2[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6a823073ab7c4f51901f88aec89eb947 | COc1cc(C(=O)O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1.N>>COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1 | C(C)(=O)O.COC1=C(C=CC(=C1)C(=O)O)C1=NC=2NC(NC(C2N1)=O)=O.N.O>>COC1=C(C=CC(=C1)C(=O)N)C1=NC=2NC(NC(C2N1)=O)=O | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11](-[c:12]2[n:13][c:14]3[nH:15][c:16](=[O:17])[nH:18][c:19](=[O:20])[c:21]3[nH:22]2)[cH:10][cH:9]1)=[O:8].[NH3:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([NH2:7])=[O:8])[cH:9][cH:10][c:11]1-[c:12]1[n:13][c:14]2[nH:15][c:16](=[O:17])[nH:18][c:19](=[O:20])[c:21]2[nH:22]1 | COc1cc(C(=O)O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1.N | COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1 | null | CN(C=O)C | CN(C=O)C.S(=O)(Cl)Cl | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=c1[nH]c(=O)c2[nH]c(-c3ccccc3)nc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A quantity of 2.3 gm of 8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione are refluxed for one hour in 50 ml of thionyl chloride with the addition of 1 drop of dimethylformamide. The excess thionyl chloride is drawn off, and the residue is stirred for 16 hours at ambient temperature with a solution of ammonia in di... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | CN(C=O)C.CN(C=O)C.S(=O)(Cl)Cl | null | null | COc1cc(C(=O)O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1.N>CN(C=O)C.CN(C=O)C.S(=O)(Cl)Cl>COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-659dfef79a1345f9a27aa0d9cf9068c9 | COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1>>COc1cc(C#N)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1 | COC1=C(C=CC(=C1)C(=O)N)C1=NC=2NC(NC(C2N1)=O)=O>>COC1=C(C=CC(=C1)C#N)C1=NC=2NC(NC(C2N1)=O)=O | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10](-[c:11]2[n:12][c:13]3[nH:14][c:15](=[O:16])[nH:17][c:18](=[O:19])[c:20]3[nH:21]2)[cH:9][cH:8]1)[NH2:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][c:10]1-[c:11]1[n:12][c:13]2[nH:14][c:15](=[O:16])[nH:17][c:18](=[O:19])[c:20]2[nH:21]1 | COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1 | COc1cc(C#N)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1 | null | null | P(=O)(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=c1[nH]c(=O)c2[nH]c(-c3ccccc3)nc2[nH]1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Prepared by boiling 0.7 gm of 8-(2-methoxy-4-aminocarbonylphenyl)-1H,3H-purin-2,6-dione in 10 ml of phosphorus oxychloride for 24 hours. The compound crystallizes as the hemihydrate.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared; for 24 hours; The compound crystallizes as the hemihydrate | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | P(=O)(Cl)(Cl)Cl | null | null | COc1cc(C(N)=O)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1>P(=O)(Cl)(Cl)Cl>COc1cc(C#N)ccc1-c1nc2[nH]c(=O)[nH]c(=O)c2[nH]1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-07ba6e5f908b4ae49ca949e471af2338 | CN.COc1ncc2[nH]c(-c3cc(S(=O)(=O)Cl)c(Cl)cc3OC)nc2n1>>CNS(=O)(=O)c1cc(-c2nc3nc(OC)ncc3[nH]2)c(OC)cc1Cl | COC1=NC=C2NC(=NC2=N1)C1=C(C=C(C(=C1)S(=O)(=O)Cl)Cl)OC.CN>>COC1=NC=C2NC(=NC2=N1)C1=C(C=C(C(=C1)S(=O)(=O)NC)Cl)OC | [CH3:1][NH2:2].Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[n:10][c:11]3[n:12][c:13]([O:14][CH3:15])[n:16][cH:17][c:18]3[nH:19]2)[c:20]([O:21][CH3:22])[cH:23][c:24]1[Cl:25]>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[n:10][c:11]3[n:12][c:13]([O:14][CH3:15])[n:16][cH:17][c:18]3[nH:19]2)[c:20]([O:21]... | CN.COc1ncc2[nH]c(-c3cc(S(=O)(=O)Cl)c(Cl)cc3OC)nc2n1 | CNS(=O)(=O)c1cc(-c2nc3nc(OC)ncc3[nH]2)c(OC)cc1Cl | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(-c2nc3ncncc3[nH]2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Prepared analogously to Example 11 from 2-methoxy-8-(2-methoxy-4-chloro-5-chlorosulfonyl-phenyl)-purine and aqueous methylamine solution.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | CN.COc1ncc2[nH]c(-c3cc(S(=O)(=O)Cl)c(Cl)cc3OC)nc2n1>>CNS(=O)(=O)c1cc(-c2nc3nc(OC)ncc3[nH]2)c(OC)cc1Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-75a79419a651472b8e61ac37752ac50b | CNC.COc1cc(S(=O)(=O)Cl)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C>>COc1cc(S(=O)(=O)N(C)C)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C | CN1C(N(C=2N=C(NC2C1=O)C1=C(C=C(C=C1)S(=O)(=O)Cl)OC)C)=O.CNC>>CN1C(N(C=2N=C(NC2C1=O)C1=C(C=C(C=C1)S(=O)(=O)N(C)C)OC)C)=O | [NH:9]([CH3:10])[CH3:11].Cl[S:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:14](-[c:15]2[n:16][c:17]3[c:18]([nH:19]2)[c:20](=[O:21])[n:22]([CH3:23])[c:24](=[O:25])[n:26]3[CH3:27])[cH:13][cH:12]1)(=[O:7])=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6](=[O:7])(=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1-[c:15]1[n:16][c:17]2[... | CNC.COc1cc(S(=O)(=O)Cl)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C | COc1cc(S(=O)(=O)N(C)C)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=c1[nH]c(=O)c2[nH]c(-c3ccccc3)nc2[nH]1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Prepared analogously to Example 11 from 1,3-dimethyl-8-(2-methoxy-4-chlorosulfonyl-phenyl)-1H,3H-purin-2,6-dione and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | CNC.COc1cc(S(=O)(=O)Cl)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C>>COc1cc(S(=O)(=O)N(C)C)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-66ffec08e9f549e2bbc01b436836183e | COc1cc(OCc2ccccc2)ccc1C(=O)O.Cn1c(N)c(N)c(=O)n(C)c1=O>>COc1cc(OCc2ccccc2)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C | CN1C(N(C(=C(C1=O)N)N)C)=O.COC1=C(C(=O)O)C=CC(=C1)OCC1=CC=CC=C1>>CN1C(N(C=2N=C(NC2C1=O)C1=C(C=C(C=C1)OCC1=CC=CC=C1)OC)C)=O | O=[C:17](O)[c:16]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1.[NH2:18][c:19]1[c:20]([NH2:21])[c:22](=[O:23])[n:24]([CH3:25])[c:26](=[O:27])[n:28]1[CH3:29]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1-[... | COc1cc(OCc2ccccc2)ccc1C(=O)O.Cn1c(N)c(N)c(=O)n(C)c1=O | COc1cc(OCc2ccccc2)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e7e72999864bfebc9719cc1ba22dd1cfcb4276023277f918059872106fb5d875 | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | O=c1[nH]c(=O)c2[nH]c(-c3ccc(OCc4ccccc4)cc3)nc2[nH]1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[C;D1;H3:8]-[#7;a:9]1:[c:10]:[#7;a:11](-[C;D1;H3:12]):[c:13](-[NH2;D1;+0:14]):[c:15](-[NH2;D1;+0:16]):[c:17]:1=[O;D1;H0:18]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c:13]2:[#7;a:11](-[C;D1;H3:12]):[c:10]:[#7;a:9](-[C;D1... | null | [] | null | null | null | null | Prepared analogously to Example 14 from 1,3-dimethyl-4,5-diamino-1H,3H-pyrimidin-2,6-dione and 2-methoxy-4-benzyloxybenzoic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1cncnc1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | null | null | null | COc1cc(OCc2ccccc2)ccc1C(=O)O.Cn1c(N)c(N)c(=O)n(C)c1=O>>COc1cc(OCc2ccccc2)ccc1-c1nc2c([nH]1)c(=O)n(C)c(=O)n2C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-812dd49b20de4a6eb087670e6fda7435 | COc1cc(OC)c(C(=O)O)cc1Br.Nc1ncnc(Cl)c1N>>COc1cc(OC)c(-c2nc3ncnc(Cl)c3[nH]2)cc1Br | NC1=NC=NC(=C1N)Cl.COC1=C(C(=O)O)C=C(C(=C1)OC)Br>>ClC1=C2NC(=NC2=NC=N1)C1=C(C=C(C(=C1)Br)OC)OC | O=[C:9](O)[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:20]([Br:21])[cH:19]1.[NH2:10][c:11]1[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]1[NH2:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][c:11]3[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]3[nH:18]2)[cH:19][c:20]1[Br:21] | COc1cc(OC)c(C(=O)O)cc1Br.Nc1ncnc(Cl)c1N | COc1cc(OC)c(-c2nc3ncnc(Cl)c3[nH]2)cc1Br | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e7e72999864bfebc9719cc1ba22dd1cfcb4276023277f918059872106fb5d875 | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc(-c2nc3ncncc3[nH]2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7].[Cl;D1;H0:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13](-[NH2;D1;+0:14]):[c:15]:1-[NH2;D1;+0:16]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c:13]2:[#7;a:12]:[c:11]:[#7;a:10]:[c:9](-[Cl;D1;H0:8]):[c:15]:2:[nH;D2;+0:16]:1):[c... | null | [] | null | null | null | null | Prepared analogously to Example 14 from 4,5-diamino-6-chloropyrimidine and 2,4-dimethoxy-5-bromo-benzoic acid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1cncnc1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | null | null | null | COc1cc(OC)c(C(=O)O)cc1Br.Nc1ncnc(Cl)c1N>>COc1cc(OC)c(-c2nc3ncnc(Cl)c3[nH]2)cc1Br |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1bcc2a3d16bb4766b58a295e2fc2fc6b | CC(Cl)Cl.COc1cc(C#N)ccc1C(=O)O.COc1nccc(N)c1N>>COC(=O)c1ccc(C2=NC3=CCNC(=O)C3=N2)c(OC)c1.Cl | COC1=NC=CC(=C1N)N.COC1=C(C(=O)O)C=CC(=C1)C#N.ClC(C)Cl.C(C)O>>Cl.COC1=C(C=CC(=C1)C(=O)OC)C1=NC=2C(C(NCC2)=O)=N1 | CC(Cl)[Cl:23].N#[C:3][c:5]1[cH:6][cH:7][c:8]([C:9]([OH:2])=[O:4])[c:19]([O:20][CH3:21])[cH:22]1.[CH3:1][O:16][c:15]1[n:14][cH:13][cH:12][c:11]([NH2:10])[c:17]1[NH2:18]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]2=[N:10][C:11]3=[CH:12][CH2:13][NH:14][C:15](=[O:16])[C:17]3=[N:18]2)[c:19]([O:20][CH3:21])[cH:22... | CC(Cl)Cl.COc1cc(C#N)ccc1C(=O)O.COc1nccc(N)c1N | COC(=O)c1ccc(C2=NC3=CCNC(=O)C3=N2)c(OC)c1.Cl | null | null | null | Acylation | OtherReaction | 59e74931176ca11a8b3b012f0820490ff7c59ac2f16614b65abe297b7bd42286 | 4e50644f8d1e19addfaa3e366597a746b1101627eaa0a56d85c5e91fb60a0ee9 | O=C1NCC=C2N=C(c3ccccc3)N=C12 | C-C(-Cl)-[Cl;H0;D1;+0:1].N#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[OH;D1;+0:9]):[c:10]:[c:11]:1.[CH3;D1;+0:12]-[O;H0;D2;+0:13]-[c;H0;D3;+0:14]1:[n;H0;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18](-[NH2;D1;+0:19]):[c;H0;D3;+0:20]:1-[NH2;D1;+0:21]>>[CH3;D1;+0:12]-[O;H0;D2;+0:9]-[... | null | [] | null | null | null | null | Prepared analogously to Example 1 from 2-methoxy-3,4-diaminopyridine and 2-methoxy-4-cyano-benzoic acid. The product mixture obtained is digested with dichloroethane/ethanol (3:1). The undissolved material is filtered off, and the solution is evaporated and boiled with methanolic hydrochloric acid. On cooling, the prod... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Carboxylic acid.Ether.Nitrile.Primary amine.Primary amine | Ester.Substituted imine.Secondary amide | c1ccncc1 | C1=NC2=CCNCC2=N1 | c1ccccc1.C1=NC2=CCNCC2=N1 | HCl | null | null | null | CC(Cl)Cl.COc1cc(C#N)ccc1C(=O)O.COc1nccc(N)c1N>>COC(=O)c1ccc(C2=NC3=CCNC(=O)C3=N2)c(OC)c1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-e60e9f255ff64e7190309e64e3d68715 | CN.COc1cc(S(=O)(=O)Cl)ccc1-c1nc2c[nH][nH]c(=O)c-2n1>>CNS(=O)(=O)c1ccc(-c2nc3c[nH][nH]c(=O)c-3n2)c(OC)c1 | COC1=C(C=CC(=C1)S(=O)(=O)Cl)C=1N=C2C(=CNNC2=O)N1.CN>>COC1=C(C=CC(=C1)S(=O)(=O)NC)C=1N=C2C(=CNNC2=O)N1 | [CH3:1][NH2:2].Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][c:12]3[cH:13][nH:14][nH:15][c:16](=[O:17])[c:18]-3[n:19]2)[c:20]([O:21][CH3:22])[cH:23]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][c:12]3[cH:13][nH:14][nH:15][c:16](=[O:17])[c:18]-3[n:19]2)[c:20]([O:21][CH3:22])... | CN.COc1cc(S(=O)(=O)Cl)ccc1-c1nc2c[nH][nH]c(=O)c-2n1 | CNS(=O)(=O)c1ccc(-c2nc3c[nH][nH]c(=O)c-3n2)c(OC)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1[nH][nH]cc2nc(-c3ccccc3)nc1-2 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Prepared analogously to Example 11 from 2-(2-methoxy-4-chlorosulfonyl-phenyl)-5-H-imidazo[4,5-d]pyridazin-4-one and aqueous methylamine solution
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1nc2cnncc2[nH]1 | HCl | null | null | null | CN.COc1cc(S(=O)(=O)Cl)ccc1-c1nc2c[nH][nH]c(=O)c-2n1>>CNS(=O)(=O)c1ccc(-c2nc3c[nH][nH]c(=O)c-3n2)c(OC)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b9ccee3c2bf64ab8b2bb177fb8f8050b | BrCc1ccc2ccccc2c1.O=C(NC(=O)c1ccccc1)NC1CCNCC1>>O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | O.C(C1=CC=CC=C1)(=O)NC(NC1CCNCC1)=O.BrCC1=CC2=CC=CC=C2C=C1.C(C)N(CC)CC>>C(C1=CC=CC=C1)(=O)NC(=O)NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1 | Br[CH2:17][c:18]1[cH:19][cH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[cH:27]1.[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH:13]1[CH2:14][CH2:15][NH:16][CH2:28][CH2:29]1>>[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH:13]1[CH2:14][CH2:15][N:16]([... | BrCc1ccc2ccccc2c1.O=C(NC(=O)c1ccccc1)NC1CCNCC1 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | null | null | null | null | 4-Benzoylureidopiperidine (1.28 g, 0.005 m), 2-(bromomethyl)naphthalene (1.1 g, 0.005 m) and triethylamine (0.6 g, 0.006 m) in dimethylformamide (25 cm3) were stirred at room temperature for 23 hours. Water was added and the precipitated solid filtered off and washed well with water. The solid was suspended in warm eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2ccccc2c1 | HBr | CN(C=O)C | null | null | BrCc1ccc2ccccc2c1.O=C(NC(=O)c1ccccc1)NC1CCNCC1>CN(C=O)C>O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6c695e0fc6704fb0ad8fd2c49b74c803 | ClCc1cccc2ccccc12.O=C(NC(=O)c1ccccc1)NC1CCNCC1>>O=C(NC(=O)c1ccccc1)NC1CCN(Cc2cccc3ccccc23)CC1 | O.ClCC1=CC=CC2=CC=CC=C12.C(C1=CC=CC=C1)(=O)NC(NC1CCNCC1)=O.C(C)N(CC)CC>>C(C1=CC=CC=C1)(=O)NC(=O)NC1CCN(CC1)CC1=CC=CC2=CC=CC=C12 | Cl[CH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12.[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH:13]1[CH2:14][CH2:15][NH:16][CH2:28][CH2:29]1>>[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH:13]1[CH2:14][CH2:15][N:16]([... | ClCc1cccc2ccccc12.O=C(NC(=O)c1ccccc1)NC1CCNCC1 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2cccc3ccccc23)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2cccc3ccccc23)CC1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | null | null | null | null | 1-Chloromethylnaphthalene (0.88 g, 0.005 m), 4-benzoylureidopiperidine (1.28 g, 0.005 m) and triethylamine (0.6 g) in dimethylformamide (25 cm3) were stirred at room temperature for 24 hours. Water was added and the precipitated solid filtered off. The solid was suspended in isopropylalcohol and acidified with ethanoli... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2ccccc2c1 | HCl | CN(C=O)C | null | null | ClCc1cccc2ccccc12.O=C(NC(=O)c1ccccc1)NC1CCNCC1>CN(C=O)C>O=C(NC(=O)c1ccccc1)NC1CCN(Cc2cccc3ccccc23)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-35a5faba84b5422a9a52f12017701c29 | CC(C)c1ccc(CCl)cc1.O=C(NC(=O)c1ccccc1)NC1CCNCC1>>CC(C)c1ccc(CN2CCC(NC(=O)NC(=O)c3ccccc3)CC2)cc1 | O.C(C)(C)C1=CC=C(CCl)C=C1.C(C1=CC=CC=C1)(=O)NC(NC1CCNCC1)=O.C(C)N(CC)CC>>C(C1=CC=CC=C1)(=O)NC(=O)NC1CCN(CC1)CC1=CC=C(C=C1)C(C)C | Cl[CH2:8][c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:28][cH:27]1.[NH:9]1[CH2:10][CH2:11][CH:12]([NH:13][C:14](=[O:15])[NH:16][C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([NH:13][C:14](=[O:15])[NH:1... | CC(C)c1ccc(CCl)cc1.O=C(NC(=O)c1ccccc1)NC1CCNCC1 | CC(C)c1ccc(CN2CCC(NC(=O)NC(=O)c3ccccc3)CC2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccccc2)CC1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | null | null | null | null | 4-Isopropylbenzyl chloride (0.84 g, 0.005 m), 4-benzoylureidopiperidine (1.28 g, 0.005 m) and triethylamine (0.6 g) in dimethylformamide (25 cm3) were stirred at room temperature for 24 hours. Water was added and the precipitated solid filtered off. The solid was suspended in isopropylalcohol and acidified with ethanol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HCl | CN(C=O)C | null | null | CC(C)c1ccc(CCl)cc1.O=C(NC(=O)c1ccccc1)NC1CCNCC1>CN(C=O)C>CC(C)c1ccc(CN2CCC(NC(=O)NC(=O)c3ccccc3)CC2)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-229294ec89824edba85133b93bb6a360 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2cccc([N+](=O)[O-])c2)CC1>>Nc1cccc(CN2CCC(NC(=O)NC(=O)c3ccccc3)CC2)c1 | C(C1=CC=CC=C1)(=O)NC(=O)NC1CCN(CC1)CC1=CC(=CC=C1)[N+](=O)[O-].[H][H]>>C(C1=CC=CC=C1)(=O)NC(=O)NC1CCN(CC1)CC1=CC(=CC=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([NH:12][C:13](=[O:14])[NH:15][C:16](=[O:17])[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:24][CH2:25]2)[cH:26]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([NH:12][C:13](=[O:14])[NH:15][C:16](=[O:17])[c:18]3... | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2cccc([N+](=O)[O-])c2)CC1 | Nc1cccc(CN2CCC(NC(=O)NC(=O)c3ccccc3)CC2)c1 | null | [Pd] | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccccc2)CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46.1 | [{"value": 46.1, "product": "C(C1=CC=CC=C1)(=O)NC(=O)NC1CCN(CC1)CC1=CC(=CC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzoyl-3-[1-(3-nitrobenzyl)piperid-4-yl]urea 4.47 g (from Example 13) was hydrogenated with 5% Pd/C (0.5 g) at atmospheric pressure and room temperature until no more hydrogen was taken up. The catalyst was filtered and the filtrate evaporated. The residue was dissolved in water and basified with 0.880 ammonia. The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | [Pd] | null | null | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2cccc([N+](=O)[O-])c2)CC1>[Pd]>Nc1cccc(CN2CCC(NC(=O)NC(=O)c3ccccc3)CC2)c1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-abd517df60204610939cf68a6c24b096 | NC1CCN(Cc2ccc3ccccc3c2)CC1.O=C(N=C=S)c1ccccc1>>O=C(NC(=S)NC1CCN(Cc2ccc3ccccc3c2)CC1)c1ccccc1 | NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(=S)NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1 | [NH2:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[cH:21]2)[CH2:22][CH2:23]1.[O:1]=[C:2]([N:3]=[C:4]=[S:5])[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[O:1]=[C:2]([NH:3][C:4](=[S:5])[NH:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:... | NC1CCN(Cc2ccc3ccccc3c2)CC1.O=C(N=C=S)c1ccccc1 | O=C(NC(=S)NC1CCN(Cc2ccc3ccccc3c2)CC1)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=C(NC(=S)NC1CCN(Cc2ccc3ccccc3c2)CC1)c1ccccc1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[C:4].[O;D1;H0:5]=[C:6](-[c:7])-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10]>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[NH;D2;+0:8]-[C:6](=[O;D1;H0:5])-[c:7])-[C:4] | null | [] | null | null | null | null | 4-Amino-1-(naphth-2-ylmethyl)piperidine (1.0 g, 0.0042 m) and benzoylisothiocyanate (0.69 g, 0.0042 m) in toluene (120 cm3) was stirred at room temperature for 6 hours. The solvent was evaporated and the gum dissolved in isopropyl alcohol and acidified with ethanolic HCl. The solvent was evaporated and the residue diss... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | C1CC[NH]CC1.c1ccc2ccccc2c1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | NC1CCN(Cc2ccc3ccccc3c2)CC1.O=C(N=C=S)c1ccccc1>C1(=CC=CC=C1)C>O=C(NC(=S)NC1CCN(Cc2ccc3ccccc3c2)CC1)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b9261355c50f45a3ac126c2d60770352 | NC(=O)NC(=O)c1cccs1.NC1CCN(Cc2ccc3ccccc3c2)CC1>>O=C(NC(=O)c1cccs1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1.C(=O)(C1=CC=CS1)NC(=O)N>>C1=C(C=CC2=CC=CC=C12)CN1CCC(CC1)NC(=O)NC(=O)C1=CC=CS1 | N[C:2](=[O:1])[NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][s:10]1.[NH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[cH:26]2)[CH2:27][CH2:28]1>>[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][s:10]1)[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[... | NC(=O)NC(=O)c1cccs1.NC1CCN(Cc2ccc3ccccc3c2)CC1 | O=C(NC(=O)c1cccs1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | ee88c85dd0298c7570ff891f0a63d5ba74c10c53d8b511286ccf5ed6d0220803 | 85c12bcb6a376caef505909a73a2892ca05bfb0340f2644fc218cdee9c5187ab | O=C(NC(=O)c1cccs1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4](=[O;D1;H0:5])-[c:6]:[#16;a:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[#16;a:7]:[c:6]-[C:4](=[O;D1;H0:5])-[#7:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9](-[C:8])-[C:11] | null | [] | null | null | null | null | 4-Amino-1-(naphth-2-ylmethyl)piperidine (1.0 g, 0.0047 m) and 1-(then-2-oyl)urea (0.65 g, 0.0042 m) in pyridine (5 cm3) was refluxed for 9.5 hours. The solvent was evaporated, water added, and the precipitated title compound filtered and washed well with water. This was recrystallised from ethanol, converted to the hyd... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Unsubstituted dicarboximide.Primary amine | Urea | null | null | c1ccsc1.C1CC[NH]CC1.c1ccc2ccccc2c1 | Other | N1=CC=CC=C1 | null | null | NC(=O)NC(=O)c1cccs1.NC1CCN(Cc2ccc3ccccc3c2)CC1>N1=CC=CC=C1>O=C(NC(=O)c1cccs1)NC1CCN(Cc2ccc3ccccc3c2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f835042249204abe88c806390379a6a4 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1>>NC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1 | C(C1=CC=CC=C1)(=O)NC(=O)NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1>>C1=C(C=CC2=CC=CC=C12)CN1CCC(CC1)NC(=O)N | O=C(c1ccccc1)[NH:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[cH:19]2)[CH2:20][CH2:21]1>>[NH2:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[cH:19]2)[CH2:20][CH2:21]1 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | NC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1 | null | null | [OH-].[Na+] | Reduction | Hydrogenolysis of amides/imides/carbamates | cef6d282debf67869b4ff7117425f8a9682536ad0cfda16621a004d70e3c594b | bd99c049ef764d527dcd2e7b23a61d65d845df2ddd7efd5a187ffda1670906e4 | c1ccc2cc(CN3CCCCC3)ccc2c1 | O=C(-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5])-c1:c:c:c:c:c:1>>[C:5]-[#7:4]-[C:2](-[NH2;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | 1-Benzoyl-3-[1-(naphth-2-ylmethyl)piperid-4-yl]urea (prepared acccording to Example 1) is hydrolysed by refluxing in 2N sodium hydroxide to give [1-(naphth-2-ylmethyl)piperid-4-yl]urea(m.p. 183°-5° C.). The product is acylated by reaction with 4-methoxybenzoyl chloride to give the title compound, m.p. of HCL, quarterhy... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Unsubstituted dicarboximide | Urea | c1ccccc1 | null | C1CC[NH]CC1.c1ccc2ccccc2c1 | HO- | [OH-].[Na+] | null | null | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1>[OH-].[Na+]>NC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-eded3f07bc674eab884909ce377e9ea4 | CNC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1.O=C(Cl)c1ccccc1>>CN(C(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1)C(=O)c1ccccc1 | CNC(=O)NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1.C(C1=CC=CC=C1)(=O)Cl.N1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)N(C(=O)NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1)C | [CH3:1][NH:2][C:3](=[O:4])[NH:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[cH:20]2)[CH2:21][CH2:22]1.Cl[C:23](=[O:24])[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][N:2]([C:3](=[O:4])[NH:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][c:14]3[cH:15... | CNC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1.O=C(Cl)c1ccccc1 | CN(C(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1)C(=O)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Acylation | N-alkylation of secondary amines with alkyl halides | 996e0ddf2d6b57ad6b8e08b45c57ed86da0355f61815643564e670f244fe345b | ed2e2a2113014ef864b0a3bd063f004647b373e1f6820e0fdd5587d12a0e8460 | O=C(NC(=O)c1ccccc1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[C;D1;H3:11]>>[C:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 1-Methyl-3-[1-(naphth-2-ylmethyl)piperid-4-yl]urea (1.4 g.) (prepared by reacting 4-amino-1-(naphth-2-ylmethyl)piperidine with methyl isocyanate) in toluene (30 cm3) was acylated using benzoyl chloride (0.92 g) in presence of pyridine (0.6 g) to give the title compound: m.p. of HCl, hemihydrate salt =164°-166° C.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Urea | Urea.Substituted dicarboximide | null | null | C1CC[NH]CC1.c1ccc2ccccc2c1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | CNC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1.O=C(Cl)c1ccccc1>C1(=CC=CC=C1)C>CN(C(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1)C(=O)c1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-fab15c502e684fbfa88cc582949b25fa | NC(=O)NC(=O)c1ccco1.NC1CCN(Cc2ccc3ccccc3c2)CC1>>NC(=O)c1occc1C(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1 | NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1.O1C(=CC=C1)C(=O)NC(=O)N.N1=CC=CC=C1.O>>C1=C(C=CC2=CC=CC=C12)CN1CCC(CC1)NC(=O)C1=C(OC=C1)C(=O)N | N[C:9]([NH:1][C:2](=[O:3])[c:4]1[o:5][cH:6][cH:7][cH:8]1)=[O:10].[NH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[cH:26]2)[CH2:27][CH2:28]1>>[NH2:1][C:2](=[O:3])[c:4]1[o:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[... | NC(=O)NC(=O)c1ccco1.NC1CCN(Cc2ccc3ccccc3c2)CC1 | NC(=O)c1occc1C(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1 | null | null | null | Acylation | OtherReaction | d0db0d4804d1c375f5ead5a4a1a61bcf24028b76ee97b6a753b32886cc0ef1ab | 5417ebfa0c4325e1c6fd3a05ca94f7d3810bb9ccad2a0aceda9b79146542a78b | O=C(NC1CCN(Cc2ccc3ccccc3c2)CC1)c1ccoc1 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[#8;a:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1.[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]>>[C:11]-[C:12](-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:10]1:[c:9]:[c:8]:[#8;a:7]:[c:6]:1-[C:4](-[NH2;D1;+0:3])=[O;D1;H0:5])-[C:14] | null | [] | null | null | null | null | 4-Amino-1-(naphth-2-ylmethyl)piperidine (1.2 g, 0.005 m) and 2-furoylurea (0.7 g) in pyridine (5 ml) was refluxed for 6 hours, then cooled. Water was added and the precipitate collected by filtration. The solid was dissolved in chloroform with a little methanol and filtered. The solvent was removed under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Unsubstituted dicarboximide.Primary amine | Primary amide.Secondary amide | c1ccoc1 | c1ccoc1 | c1ccoc1.C1CC[NH]CC1.c1ccc2ccccc2c1 | Other | null | null | null | NC(=O)NC(=O)c1ccco1.NC1CCN(Cc2ccc3ccccc3c2)CC1>>NC(=O)c1occc1C(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5a710b5c50314be3848a9b1928e8c6b3 | CCOC(=O)c1ccccn1.NC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1>>O=C(NC(=O)c1ccccn1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | N.N.N1=C(C=CC=C1)C(=O)OCC.[Na].N.C1=C(C=CC2=CC=CC=C12)CN1CCC(CC1)NC(=O)N>>N1=C(C=CC=C1)C(=O)NC(=O)NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1 | CCO[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1.[O:1]=[C:2]([NH2:3])[NH:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[cH:27]2)[CH2:28][CH2:29]1>>[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1)[NH:12][CH:13]1[CH2:14][CH2:15][N:16](... | CCOC(=O)c1ccccn1.NC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1 | O=C(NC(=O)c1ccccn1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | null | null | null | Acylation | Aminolysis of esters | 0330f4993bddb0991bb489c6979d77406cc1a28c3b8a210251333bf0843c59df | 3e0cd27ef7f0f0adedddcc27920abb1de1e606dd69fa301eb6865b7fac89ec4a | O=C(NC(=O)c1ccccn1)NC1CCN(Cc2ccc3ccccc3c2)CC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[#7:8]-[C:9](-[NH2;D1;+0:10])=[O;D1;H0:11]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:11])-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 32.5 | [{"value": 32.5, "product": "N1=C(C=CC=C1)C(=O)NC(=O)NC1CCN(CC1)CC1=CC2=CC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Sodium (0.1 g, 4.35 mmol) in liquid ammonia (100-150 cm3) was stirred until the blue colour was discharged. A bomb was charged with [1-(Naphth-2-yl-methyl)piperid-4-yl]urea (0.83 g, 2.93 mmol) and the liquid ammonia solution was added. The mixture was stirred at room temperature for 2 days then the bomb was cooled to -... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Urea | Urea.Unsubstituted dicarboximide | null | null | c1ccncc1.C1CC[NH]CC1.c1ccc2ccccc2c1 | HO- | null | null | 48 | CCOC(=O)c1ccccn1.NC(=O)NC1CCN(Cc2ccc3ccccc3c2)CC1>>O=C(NC(=O)c1ccccn1)NC1CCN(Cc2ccc3ccccc3c2)CC1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-0255eb3447734ab3a76de421c8683068 | Br>>[Br-] | CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C.Br.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 | [BrH:1]>>[Br-:1] | Br | [Br-] | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [BrH;D0;+0:1]>>[Br-;H0;D0:1] | null | [] | 60 | CELSIUS | 2 | HOUR | Retinol (2 g, 7 mmol) is dissolved in 50 ml of toluene and 2.4 g (7 mmol) of triphenylphosphonium hydrobromide is added. The mixture is stirred for 18 hours at room temperature and 2 hours at 60° C., then cooled and the toluene separated. The viscous sediment is digested four times with 25 ml of dry toluene. The final ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C1(=CC=CC=C1)C | 60 | 2 | Br>C1(=CC=CC=C1)C>[Br-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-76f548fb96d24dc298bc9940f96eeedc | CCOC(=O)C(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C>>CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO | C(C)OC(C(=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C)C)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC(CO)=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C | CCO[C:23]([C:21](=[CH:20][CH:19]=[C:17]([CH:16]=[CH:15][CH:14]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]1=[C:6]([CH3:7])[CH2:8][CH2:9][CH2:10][C:11]1([CH3:12])[CH3:13])[CH3:18])[CH3:22])=[O:24]>>[CH3:1][C:2]([CH:3]=[CH:4][C:5]1=[C:6]([CH3:7])[CH2:8][CH2:9][CH2:10][C:11]1([CH3:12])[CH3:13])=[CH:14][CH:15]=[CH:16][C:17]([CH3:18])... | CCOC(=O)C(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1=CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;D1;H3:4])=[C:5]-[C:6]=[C:7]>>[C:7]=[C:6]-[C:5]=[C:3](-[C;D1;H3:4])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 4 | HOUR | A solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenoic acid ethyl ester (1.85 g, 5 mmol) in 25 ml of anhydrous THF is cooled to -10° C. and 0.19 g (5 mmol) of LAH is added in portions. The resulting mixture is stirred for 4 hours and quenched carefully with 0.4 ml of water. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1=CCCCC1 | HO- | C1CCOC1 | null | 4 | CCOC(=O)C(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C>C1CCOC1>CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-16b2bb9cea4a43ed8b1c6f70818936f9 | CC(=O)Cl.CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO>>CC(=O)OCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C | C(C)(=O)Cl.CC(CO)=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C.N1=CC=CC=C1>>C(C)(=O)OCC(=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C)C | Cl[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][C:6]([CH3:7])=[CH:8][CH:9]=[C:10]([CH3:11])[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[CH:17]=[CH:18][C:19]1=[C:20]([CH3:21])[CH2:22][CH2:23][CH2:24][C:25]1([CH3:26])[CH3:27]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6]([CH3:7])=[CH:8][CH:9]=[C:10]([CH3:11])[CH:12]=[CH:13][CH:14]=[C:15]([CH3:... | CC(=O)Cl.CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO | CC(=O)OCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C | null | null | CCOCC.C(Cl)Cl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | C1=CCCCC1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]=[C:5]-[C:6]=[C:7](-[C;D1;H3:8])-[C:9]-[OH;D1;+0:10]>>[C:4]=[C:5]-[C:6]=[C:7](-[C;D1;H3:8])-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | 0 | CELSIUS | 2 | HOUR | A solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol (1.6 g, 5 mmol) and pyridine (9.6 ml, 7.3 mmol) in 15 ml of anhydrous methylene chloride is stirred in an ice bath and a solution of acetyl chloride (0.37 ml, 5.25 mmol) in 5 ml of anhydrous methylene chloride is added d... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1=CCCCC1 | HCl | CCOCC.C(Cl)Cl | 0 | 2 | CC(=O)Cl.CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO>CCOCC.C(Cl)Cl>CC(=O)OCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-32560364bc2c4583929e9619527c24ce | CC(=O)OCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C.[S-]c1ccccc1>>CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CSc1ccccc1 | C(C)(=O)OCC(=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C)C.[S-]C1=CC=CC=C1.[Na+]>>C1(=CC=CC=C1)SCC(=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C)C | CC(=O)O[CH2:23][C:21](=[CH:20][CH:19]=[C:17]([CH:16]=[CH:15][CH:14]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]1=[C:6]([CH3:7])[CH2:8][CH2:9][CH2:10][C:11]1([CH3:12])[CH3:13])[CH3:18])[CH3:22].[S-:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][C:2]([CH:3]=[CH:4][C:5]1=[C:6]([CH3:7])[CH2:8][CH2:9][CH2:10][C:11]1([CH3:12])... | CC(=O)OCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C.[S-]c1ccccc1 | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CSc1ccccc1 | null | null | C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 5733dbf3fa3c89f36c04baccc93170809e2644bb7f231de1b5858a1113f0eb5f | d5aadbfeb774ee97265b01254dc5b32931df6322312658654ed230582a36a6e5 | C(=CC=CC=CC1=CCCCC1)C=CC=CCSc1ccccc1 | C-C(=O)-O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[C:4]-[C:5]=[C:6].[S-;H0;D1:7]-[c:8](:[c:9]):[c:10]>>[C:6]=[C:5]-[C:4]=[C:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 18 | HOUR | To a solution of 1.85 g (5 mmol) of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl acetate in 25 ml of anhydrous THF and 8 ml of HMPA is added in portions 0.68 g (5.2 mmol) of sodium thiophenoxide. The resulting mixture is stirred at room temperature for 18 hours and then taken up in ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Monosulfide | null | null | C1=CCCCC1.c1ccccc1 | HO- | C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C.C(C)OCC | null | 18 | CC(=O)OCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C.[S-]c1ccccc1>C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C.C(C)OCC>CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CSc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c01cb519f753417099bc0730fcf1a233 | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO>>CNCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C | CC(CO)=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrN1C(CCC1=O)=O>>CNCC(=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C)C | O[CH2:3][C:4]([CH3:5])=[CH:6][CH:7]=[C:8]([CH3:9])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[CH:15]=[CH:16][C:17]1=[C:18]([CH3:19])[CH2:20][CH2:21][CH2:22][C:23]1([CH3:24])[CH3:25]>>[CH3:1][NH:2][CH2:3][C:4]([CH3:5])=[CH:6][CH:7]=[C:8]([CH3:9])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[CH:15]=[CH:16][C:17]1=[C:18]([CH3:19])[... | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO | CNCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 48dad0f5b231c0d740a50fd8810c796a0b51f24cdb89b976c9df81724489b664 | 1da3d050763f9c56998cc752e2b3f224578fac5a94a0c6233507a69672a2b533 | C1=CCCCC1 | O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[C:4]-[C:5]=[C:6]>>[C:6]=[C:5]-[C:4]=[C:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[#7:7]-[C;D1;H3:8] | null | [] | null | null | 18 | HOUR | A solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol (3.2 g, 10 mmol) and triphenylphosphine (2.88 g, 11 mmol) in 20 ml of THF is stirred in an ice bath and 1.78 g (10 mmol) of N-bromosuccinimide is added in small portions over a period of one hour. After addition, the coo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Secondary amine | null | null | C1=CCCCC1 | null | C1CCOC1 | null | 18 | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO>C1CCOC1>CNCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-881c5b03087e4b6fa8b661db36b63481 | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO.CO>>COCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C | C(=O)(O)[O-].[Na+].CC(CO)=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C.C(OC)(OC)OC.CO.FC(C(=O)O)(F)F>>COCC(=CC=C(C=CC=C(C=CC1=C(CCCC1(C)C)C)C)C)C | [OH:2][CH2:3][C:4]([CH3:5])=[CH:6][CH:7]=[C:8]([CH3:9])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[CH:15]=[CH:16][C:17]1=[C:18]([CH3:19])[CH2:20][CH2:21][CH2:22][C:23]1([CH3:24])[CH3:25].O[CH3:1]>>[CH3:1][O:2][CH2:3][C:4]([CH3:5])=[CH:6][CH:7]=[C:8]([CH3:9])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[CH:15]=[CH:16][C:17]1=[C:1... | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO.CO | COCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Alcohol to ether | c873da657d50d2833a5f2666591cb755f50dd7890d803ad948097f1a9004ed92 | 6598fea024a5fbd71aab93259b9b6cb0238901bd1731856222fcfdfc0bdff95d | C1=CCCCC1 | O-[CH3;D1;+0:1].[C:2]=[C:3]-[C:4]=[C:5](-[C;D1;H3:6])-[C:7]-[OH;D1;+0:8]>>[C:2]=[C:3]-[C:4]=[C:5](-[C;D1;H3:6])-[C:7]-[O;H0;D2;+0:8]-[CH3;D1;+0:1] | null | [] | null | null | 8 | HOUR | To a solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol (1.6 g, 5 mmol), 106 g (10 mmol) of trimethyl orthoformate and 160 mg (5 mmol) of dry methanol in 5 ml of dry THF is added dropwise a solution of 40 μL of trifluoroacetic acid in 1 ml of dry THF over a 1 minute period... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Methanol | Ether | null | null | C1=CCCCC1 | HO- | C1CCOC1 | null | 8 | CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC=C(C)CO.CO>C1CCOC1>COCC(C)=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-8f678bfe64a843f0a9a23754ecb07be3 | c1ccc([Se][Se]c2ccccc2)cc1>>[Se]=[SeH-] | O1CCCC1.[PH2](=O)O.C1(=CC=CC=C1)C(C[Se]CC(C1=CC=CC=C1)N)N.C1(=CC=CC=C1)[Se][Se]C1=CC=CC=C1.O1CCCC1>>C1(=CC=CC=C1)C(C[Se]CC(C1=CC=CC=C1)N)N.[SeH-]=[Se] | c1ccc([Se:20][Se:21]c2ccccc2)cc1>>[Se:20]=[SeH-:21] | c1ccc([Se][Se]c2ccccc2)cc1 | [Se]=[SeH-] | null | null | CCOCC | Miscellaneous | OtherReaction | c7270c048ee5b92f11aec509cd1fcec9f72e573bd2e78bc92bb00ad72ceb64c9 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Se;H0;D2;+0:1](-[Se;H0;D2;+0:2]-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[Se;H0;D1;+0:1]=[SeH-;D1:2] | null | [] | null | null | null | null | A preferred compound is phenyl-2-aminoethyl selenide and salts thereof. Phenyl-2-aminoethyl selenide (PAESe) was synthesized by employing the following procedure. Diphenyl diselenide, 24.707 g (79.16 mmol) was dissolved into 100 ml of tetrahydrofuran (THF) with steam heating. To the intensely dark red THF solution was ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1 | null | null | Other | CCOCC | null | null | c1ccc([Se][Se]c2ccccc2)cc1>CCOCC>[Se]=[SeH-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-582897d5e0ee4beea88f45c69a6bdd13 | ClCc1cccc2c1CC2.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21.[Cl-] | ClCC1=C2C(CC2)=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OCC>>[Cl-].C1(=CC=CC=C1)[P+](CC1=CC2=C(C=C2)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH2:1]1[CH2:2][c:3]2[c:4]1[c:5]([CH2:6][Cl:29])[cH:26][cH:27][cH:28]2.[P:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH:1]1=[CH:2][c:3]2[cH:4][c:5]([CH2:6][P+:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)([c:14]3[cH:15][cH:16][... | ClCc1cccc2c1CC2.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21.[Cl-] | null | null | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 127f8013fd832f07dba9c227580ae1d03fe917a64b25bf9f7f4f72f6647c370e | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21 | [Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]2:[c;H0;D3;+0:8]:1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-2.[c:11]:[c:12](-[P;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c:17](:[c:18]):[c:19]):[c:20]>>[Cl-;H0;D0:1].[c:11]:[c:12](-[P+;H0;D4:13](-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6]2:[c:7](:[cH;D2;+0:8]:1)... | null | [] | null | null | null | null | A solution of 4-chloromethylbenzocyclobutene (24.4 g, 160 mmol) and triphenylphosphine (41.9 g, 160 mmol) in 120 ml of chloroform was heated at reflux for 24 h. Addition of diethyl ether followed by filtration gave tripheny(4-benzocyclobutenyl)methyl phosphonium chloride as a white powder: 1H NMR (CDCl3) δ3.03 (m, 4H),... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)CC2 | C1=Cc2ccccc21 | C1=Cc2ccccc21.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(Cl)(Cl)Cl | null | null | ClCc1cccc2c1CC2.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(Cl)(Cl)Cl>C1=Cc2cc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)ccc21.[Cl-] |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c8ad3021517e47849a4ef0618fa4b5f1 | CC(C)=O.C[Si](C)(C)Cl.FC(F)(F)C(c1ccc(Br)cc1)(c1ccc(Br)cc1)C(F)(F)F>>C[Si](C)(C)c1ccc(C(c2ccc([Si](C)(C)C)cc2)(C(F)(F)F)C(F)(F)F)cc1 | C(=O)=O.CC(=O)C.BrC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C=C1)Br.C(CCC)[Li].Cl[Si](C)(C)C>>C[Si](C1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C=C1)[Si](C)(C)C)(C)C | O=C([CH3:15])[CH3:16].Cl[Si:2]([CH3:1])([CH3:3])[CH3:4].Br[c:5]1[cH:6][cH:7][c:8]([C:9]([c:10]2[cH:11][cH:12][c:13](Br)[cH:18][cH:19]2)([C:20]([F:21])([F:22])[F:23])[C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([c:10]2[cH:11][cH:12][c:13]([Si:14]([CH3:15])([C... | CC(C)=O.C[Si](C)(C)Cl.FC(F)(F)C(c1ccc(Br)cc1)(c1ccc(Br)cc1)C(F)(F)F | C[Si](C)(C)c1ccc(C(c2ccc([Si](C)(C)C)cc2)(C(F)(F)F)C(F)(F)F)cc1 | null | null | CCCCCC.O1CCCC1 | Miscellaneous | OtherReaction | d9c0813edfd655437e0619c276031b87485ac244e3a31e4a6d0b649d0faaaaba | 400c69d416533a42d629d44e8f6638def1c96e24296888dc3d74d06a33e92041 | c1ccc(Cc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].Cl-[Si;H0;D4;+0:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14].O=C(-[CH3;D1;+0:15])-[CH3;D1;+0:16]>>[C;D1;H3:17]-[#14:18](-[CH3;D1;+0:15])(-[CH3;D1;+0:16])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:12]-[Si;H0;D4;+0:11](-[C;... | null | [] | -78 | CELSIUS | 16 | HOUR | To a solution of 4.62 g (0.1 mole) 2,2-bis(4-bromophenyl)hexafluoropropane in 75 ml of anhydrous tetrahydrofuran was added dropwise 28 ml (0.4 moles) of a 1.4 molar solution of n-butyllithium in hexane while the reaction mixture was cooled in a dry ice-acetone slush. The reaction mixture was stirred for one half hour a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ketone.Silyl protective group | Silyl protective group.Silyl protective group | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | CCCCCC.O1CCCC1 | -78 | 16 | CC(C)=O.C[Si](C)(C)Cl.FC(F)(F)C(c1ccc(Br)cc1)(c1ccc(Br)cc1)C(F)(F)F>CCCCCC.O1CCCC1>C[Si](C)(C)c1ccc(C(c2ccc([Si](C)(C)C)cc2)(C(F)(F)F)C(F)(F)F)cc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1df2989375bc46478b5ee78beb16d265 | CCCCCl.c1ccccc1>>CCCCc1ccccc1 | ClCCCC.NC(=O)N.S(O)(O)(=O)=O.C1=CC=CC=C1.NC(=O)N.S(O)(O)(=O)=O.NC(=O)N.S(O)(O)(=O)=O>>C(CCC)C1=CC=CC=C1 | Cl[CH2:4][CH2:3][CH2:2][CH3:1].[cH:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | CCCCCl.c1ccccc1 | CCCCc1ccccc1 | null | null | null | C-C Coupling | Friedel-Crafts alkylation with halide | abd82b32c15853d5913cc8f5d51923ff8cee2c9e5cfc2628ece51b84576c3f2d | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | null | [] | null | null | 10 | MINUTE | Normal-butylbenzene is prepared by heating equal molar amounts of 1-chlorobutane and benzene in a molten urea-sulfuric acid component containing 42.6 weight percent urea and 75.4 weight percent sulfuric acid having a urea/sulfuric acid molar ratio of 1.2 at a temperature of 140° F. and a pressure of 100 psig. for a per... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | 0.166667 | CCCCCl.c1ccccc1>>CCCCc1ccccc1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cb342278cc67421d861b38254858d7ca | N=C(N)N.O=C1CC(Cl)(CCl)O1>>Nc1nc(O)cc(CCl)n1 | ClC1(CC(O1)=O)CCl.Cl.NC(=N)N.Cl>>NC1=NC(=CC(=N1)CCl)O | [NH2:1][C:2]([NH2:3])=[NH:10].Cl[C:7]1([CH2:8][Cl:9])O[C:4](=[O:5])[CH2:6]1>>[NH2:1][c:2]1[n:3][c:4]([OH:5])[cH:6][c:7]([CH2:8][Cl:9])[n:10]1 | N=C(N)N.O=C1CC(Cl)(CCl)O1 | Nc1nc(O)cc(CCl)n1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 0696bdbf97c9bf9861014eae451ad11c18128202bdc40d43b11a076939b2d145 | 129990a0b56fe349b93ca8731b8ff9a7cfaf015afb641b0852728d0f92224b5a | c1cncnc1 | Cl-[C;H0;D4;+0:1]1(-[C:2]-[Cl;D1;H0:3])-O-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[CH2;D2;+0:6]-1.[N;D1;H2:7]-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[NH;D1;+0:10]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:6]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[n;H0;D2;+0:9]:[c;H0;D3;+0:8](-[N;D1;H2:7]):[n;H0;D2;+0:10]:1 | null | [] | 120 | CELSIUS | null | null | 620 parts of 4-chloro-4-chloromethyloxetan-2-one and 440 parts of guanidine hydrochloride were charged to a reaction flask and the mixture was stirred and heated under nitrogen purge as the bath temperature was gradually raised to 120° C. When the bath temperature approached 100° C., reaction commenced accompanied by e... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Primary amine | Aromatic alcohol | C1COC1 | c1cncnc1 | c1cncnc1 | HCl | O | 120 | null | N=C(N)N.O=C1CC(Cl)(CCl)O1>O>Nc1nc(O)cc(CCl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-bd220c185fdc4f29a50c93efa6db59de | N=C(N)N.O=C1CC(Cl)(CC(Cl)(Cl)Cl)O1>>Nc1nc(O)cc(C=C(Cl)Cl)n1 | ClC1(CC(O1)=O)CC(Cl)(Cl)Cl.Cl.NC(=N)N.Cl>>NC1=NC(=CC(=N1)C=C(Cl)Cl)O | [NH2:1][C:2]([NH2:3])=[NH:12].O=[C:4]1[O:5][C:7](Cl)([CH2:8][C:9](Cl)([Cl:10])[Cl:11])[CH2:6]1>>[NH2:1][c:2]1[n:3][c:4]([OH:5])[cH:6][c:7]([CH:8]=[C:9]([Cl:10])[Cl:11])[n:12]1 | N=C(N)N.O=C1CC(Cl)(CC(Cl)(Cl)Cl)O1 | Nc1nc(O)cc(C=C(Cl)Cl)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f6e8b6c016c264d65a00ac2c1b3c0e2e7c0f17cf4fe88b866e901fc8f9bbef9f | 7b2bd2e2424b24297e7c6fcfa0019ee4773825ace42c090d742953d12c1e6bbf | c1cncnc1 | Cl-[C;H0;D4;+0:1]1(-[CH2;D2;+0:2]-[C;H0;D4;+0:3](-Cl)(-[Cl;D1;H0:4])-[Cl;D1;H0:5])-[CH2;D2;+0:6]-[C;H0;D3;+0:7](=O)-[O;H0;D2;+0:8]-1.[N;D1;H2:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[NH;D1;+0:12]>>[Cl;D1;H0:4]-[C;H0;D3;+0:3](-[Cl;D1;H0:5])=[CH;D2;+0:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[OH;D1;+0:8]):[n;H0;D2;+0:... | null | [] | 140 | CELSIUS | 45 | MINUTE | 119 Parts of 4-chloro-4-(2,2,2-trichloroethyl)-oxetan-2-one and 95.5 parts of guanidine hydrochloride were charged to a reaction flask and heated in an oil bath at 140° C. for 15 minutes. The solid dissolved and HCl gas was evolved. The oil bath temperature was raised to 160° C. and heating was continued for a further ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Tertiary halide.Ester.Primary amine | Alkenyl halide.Alkenyl halide.Aromatic alcohol | C1COC1 | c1cncnc1 | c1cncnc1 | HCl | null | 140 | 0.75 | N=C(N)N.O=C1CC(Cl)(CC(Cl)(Cl)Cl)O1>>Nc1nc(O)cc(C=C(Cl)Cl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c5ccdb6526a343d180e97ac51b4a58da | Nc1nc(O)cc(CCl)n1.O=P(Cl)(Cl)Cl>>Nc1nc(Cl)cc(CCl)n1 | NC1=NC(=CC(=N1)CCl)O.P(=O)(Cl)(Cl)Cl>>NC1=NC(=CC(=N1)Cl)CCl | O[c:4]1[n:3][c:2]([NH2:1])[n:10][c:7]([CH2:8][Cl:9])[cH:6]1.O=P(Cl)(Cl)[Cl:5]>>[NH2:1][c:2]1[n:3][c:4]([Cl:5])[cH:6][c:7]([CH2:8][Cl:9])[n:10]1 | Nc1nc(O)cc(CCl)n1.O=P(Cl)(Cl)Cl | Nc1nc(Cl)cc(CCl)n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c34cc3a735ba90a6ebc3a31af86c6a0085713d9dcab569055caa3b8d444bb07d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cncnc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[C:7]):[c:8]:1>>[C:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:8]:1 | null | [] | null | null | 10 | MINUTE | 47.9 Parts of 2-amino-4-chloromethyl-6-hydroxypyrimidine was added portionwise to 410 parts of phosphorus oxychloride with stirring. The mixture was placed in an oil bath at 130° C. and stirred until all the solid had dissolved and then for a further 10 minutes. The solution was cooled and the excess of phosphorus oxyc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | 0.166667 | Nc1nc(O)cc(CCl)n1.O=P(Cl)(Cl)Cl>>Nc1nc(Cl)cc(CCl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2d0c936e376d46a4a7dfb16b647c8164 | Nc1nc(O)cc(C=C(Cl)Cl)n1.O=P(Cl)(Cl)Cl>>Nc1nc(Cl)cc(C=C(Cl)Cl)n1 | NC1=NC(=CC(=N1)C=C(Cl)Cl)O.P(=O)(Cl)(Cl)Cl>>NC1=NC(=CC(=N1)Cl)C=C(Cl)Cl | O[c:4]1[n:3][c:2]([NH2:1])[n:12][c:7]([CH:8]=[C:9]([Cl:10])[Cl:11])[cH:6]1.O=P(Cl)(Cl)[Cl:5]>>[NH2:1][c:2]1[n:3][c:4]([Cl:5])[cH:6][c:7]([CH:8]=[C:9]([Cl:10])[Cl:11])[n:12]1 | Nc1nc(O)cc(C=C(Cl)Cl)n1.O=P(Cl)(Cl)Cl | Nc1nc(Cl)cc(C=C(Cl)Cl)n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c34cc3a735ba90a6ebc3a31af86c6a0085713d9dcab569055caa3b8d444bb07d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cncnc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[C:7]=[C:8]):[c:9]:1>>[C:8]=[C:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:9]:1 | null | [] | null | null | null | null | 10 Parts of 2-amino-4-(2,2-dichlorovinyl)-6-hydroxypyrimidine and 66 parts of phosphorus oxychloride were heated together under reflux for 1 hour with stirring. The solution was cooled and excess phosphorus oxychloride was removed in vacuo on a rotary evaporator. The residual viscous oil was poured onto ice, with stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | null | Nc1nc(O)cc(C=C(Cl)Cl)n1.O=P(Cl)(Cl)Cl>>Nc1nc(Cl)cc(C=C(Cl)Cl)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c486bd8087ef4bc39cbd7955c7ea7c4c | C[O-].Nc1nc(Cl)cc(C=C(Cl)Cl)n1>>COc1cc(C=C(Cl)Cl)nc(N)n1 | [Na].NC1=NC(=CC(=N1)Cl)C=C(Cl)Cl.C[O-].[Na+]>>NC1=NC(=CC(=N1)C=C(Cl)Cl)OC | [CH3:1][O-:2].Cl[c:3]1[cH:4][c:5]([CH:6]=[C:7]([Cl:8])[Cl:9])[n:10][c:11]([NH2:12])[n:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[C:7]([Cl:8])[Cl:9])[n:10][c:11]([NH2:12])[n:13]1 | C[O-].Nc1nc(Cl)cc(C=C(Cl)Cl)n1 | COc1cc(C=C(Cl)Cl)nc(N)n1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | f4c4542ecb881e89239e5ab87f858188051f8469235d618ac5a349648125ce56 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C:7]=[C:8]):[c:9]:1.[C;D1;H3:10]-[O-;H0;D1:11]>>[C:8]=[C:7]-[c:6]1:[#7;a:5]:[c:3](-[N;D1;H2:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[C;D1;H3:10]):[c:9]:1 | null | [] | null | null | 4 | HOUR | 22.0 Parts of 2-amino-4-chloro-6-(2,2-dichlorovinyl)pyrimidine was dissolved in 500 parts of dry methanol and stirred whilst a solution of sodium methoxide, prepared by dissolving 4.6 parts of sodium in 200 parts of dry methanol, was added dropwise, over 30 minutes at ambient temperature. The resulting solution was sti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | CO | null | 4 | C[O-].Nc1nc(Cl)cc(C=C(Cl)Cl)n1>CO>COc1cc(C=C(Cl)Cl)nc(N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-49bd71cf48ae45fcbb90a9526cdec8dd | CNC.Nc1nc(Cl)cc(CCl)n1>>CN(C)c1cc(CCl)nc(N)n1 | Cl.CNC.[Na].NC1=NC(=CC(=N1)Cl)CCl>>NC1=NC(=CC(=N1)CCl)N(C)C | [CH3:1][NH:2][CH3:3].Cl[c:4]1[cH:5][c:6]([CH2:7][Cl:8])[n:9][c:10]([NH2:11])[n:12]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]([CH2:7][Cl:8])[n:9][c:10]([NH2:11])[n:12]1 | CNC.Nc1nc(Cl)cc(CCl)n1 | CN(C)c1cc(CCl)nc(N)n1 | null | null | CO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1.[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C:7]-[c:6]1:[#7;a:5]:[c:3](-[N;D1;H2:4]):[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10](-[C;D1;H3:9])-[C;D1;H3:11]):[c:8]:1 | null | [] | null | null | null | null | 8.1 Parts of dimethylamine hydrochloride was added to a solution of 2.3 parts of sodium in 20 parts of methanol. The resulting mixture was added dropwise with stirring over about 10 minutes to a solution of 9.9 parts of 2-amino-4-chloro-6-chloromethylpyrimidine in 50 parts of methanol. The reaction was monitored by TLC... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | CO | null | null | CNC.Nc1nc(Cl)cc(CCl)n1>CO>CN(C)c1cc(CCl)nc(N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-57c87955e9ed4a11aa4e6f98c7716c2b | COc1cc(CCl)nc(N)n1.[F-]>>COc1cc(CF)nc(N)n1 | NC1=NC(=CC(=N1)CCl)OC.[F-].[Cs+]>>NC1=NC(=CC(=N1)CF)OC | Cl[CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[n:11][c:9]([NH2:10])[n:8]1.[F-:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][F:7])[n:8][c:9]([NH2:10])[n:11]1 | COc1cc(CCl)nc(N)n1.[F-] | COc1cc(CF)nc(N)n1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1cncnc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[F-;H0;D0:8]>>[F;H0;D1;+0:8]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | null | null | A mixture of 17.0 parts of 2-amino-4-chloromethyl-6-methoxypyrimidine, 59.5 parts of caesium fluoride and 130 parts of dry dimethylformamide was stirred under reflux for 2 hours. The mixture was cooled and evaporated in vacuo. The residue was taken up in ethyl acetate and the solution was washed four times with water. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1cncnc1 | Other | CN(C=O)C | null | null | COc1cc(CCl)nc(N)n1.[F-]>CN(C=O)C>COc1cc(CF)nc(N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2890b78e01af42029f6cf55bc787a012 | CS.Nc1nc(F)cc(CF)n1>>CSc1cc(CF)nc(N)n1 | NC1=NC(=CC(=N1)F)CF.CS.O1CCCC1.[Na]>>NC1=NC(=CC(=N1)CF)SC | [CH3:1][SH:2].F[c:3]1[cH:4][c:5]([CH2:6][F:7])[n:8][c:9]([NH2:10])[n:11]1>>[CH3:1][S:2][c:3]1[cH:4][c:5]([CH2:6][F:7])[n:8][c:9]([NH2:10])[n:11]1 | CS.Nc1nc(F)cc(CF)n1 | CSc1cc(CF)nc(N)n1 | null | null | CO | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 270d69d232cba6e3d197f50ba299db6b74c94a769bfdb5d3c28eabf0ce3253f9 | b7fe376f7aad2517725eef26ab981e4baa6c31c5f38fdf89e7c52a4a2c6cc1d2 | c1cncnc1 | F-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1.[C;D1;H3:9]-[SH;D1;+0:10]>>[C:7]-[c:6]1:[#7;a:5]:[c:3](-[N;D1;H2:4]):[#7;a:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:10]-[C;D1;H3:9]):[c:8]:1 | null | [] | null | null | 1 | HOUR | A mixture of 1.0 part of 2-amino-4-fluoro-6-fluoromethylpyrimidine, 3.0 parts of methanethiol and 50 parts of dry tetrahydrofuran was stirred at 5° C. whilst a solution of 0.16 parts of sodium in 20 parts of dry methanol was added dropwise. The temperature was kept below 10° C. with ice-bath cooling. When the addition ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aliphatic thiol | Monosulfide | c1cncnc1 | c1cncnc1 | c1cncnc1 | HF | CO | null | 1 | CS.Nc1nc(F)cc(CF)n1>CO>CSc1cc(CF)nc(N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c5c4f3d95a07449791cf3a5bbb4138ec | CCCCO.Nc1nc(Cl)cc(CCl)n1>>CCCCOc1cc(CCl)nc(N)n1 | NC1=NC(=CC(=N1)Cl)CCl.CC(C)([O-])C.[K+].C(CCC)O>>NC1=NC(=CC(=N1)OCCCC)CCl | [CH3:1][CH2:2][CH2:3][CH2:4][OH:5].Cl[c:6]1[cH:7][c:8]([CH2:9][Cl:10])[n:11][c:12]([NH2:13])[n:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([CH2:9][Cl:10])[n:11][c:12]([NH2:13])[n:14]1 | CCCCO.Nc1nc(Cl)cc(CCl)n1 | CCCCOc1cc(CCl)nc(N)n1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1.[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1 | null | [] | 50 | CELSIUS | null | null | 3,56 Parts of 2-amino-4-chloro-6-chloromethylpyrimidine and 2.24 parts of potassium t-butoxide were dissolved in 60 parts of n-butanol at room temperature then the solution was heated at 50° C. for 2 hours, with stirring. After this time, the solution was cooled and evaporated in vacuo. The residue was partitioned betw... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | 50 | null | CCCCO.Nc1nc(Cl)cc(CCl)n1>>CCCCOc1cc(CCl)nc(N)n1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f606e875095f482a95b954389719a17c | C=CCNCC=C.Nc1nc(Cl)cc(CCl)n1>>C=CCN(CC=C)c1cc(CCl)nc(N)n1 | NC1=NC(=CC(=N1)Cl)CCl.C(C=C)NCC=C>>NC1=NC(=CC(=N1)CCl)N(CC=C)CC=C | [CH2:1]=[CH:2][CH2:3][NH:4][CH2:5][CH:6]=[CH2:7].Cl[c:8]1[cH:9][c:10]([CH2:11][Cl:12])[n:13][c:14]([NH2:15])[n:16]1>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[c:8]1[cH:9][c:10]([CH2:11][Cl:12])[n:13][c:14]([NH2:15])[n:16]1 | C=CCNCC=C.Nc1nc(Cl)cc(CCl)n1 | C=CCN(CC=C)c1cc(CCl)nc(N)n1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1.[C;D1;H2:9]=[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]=[C;D1;H2:15]>>[C:7]-[c:6]1:[#7;a:5]:[c:3](-[N;D1;H2:4]):[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12](-[C:11]-[C:10]=[C;D1;H2:9])-[C:13]-[C:14]=[C;D1;H2:15]):[c:8]:1 | null | [] | null | null | null | null | 3.56 Parts of 2-amino-4-chloro-6-chloromethylpyrimidine and 3.9 parts of diallylamine were reacted together according to the method of Example 15 to give 2-amino-4-chloromethyl-6-diallylaminopyrimidine m.p. 53°-55° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | null | C=CCNCC=C.Nc1nc(Cl)cc(CCl)n1>>C=CCN(CC=C)c1cc(CCl)nc(N)n1 |
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