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-16aafcac545a4847bcf7a5fd0cf05ce5 | CN1CC[C@H](O)C1.ClCCl.ClCCl.O=C(O)c1cccnc1Cl>>CN1C[C@H](CCCl)Oc2ncccc2C1=O.Cl | C(Cl)Cl.ClC1=C(C(=O)O)C=CC=N1.CN1C[C@H](CC1)O.[H-].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)(=O)O.C(Cl)Cl>>Cl.ClCC[C@@H]1OC2=C(C(N(C1)C)=O)C=CC=N2 | [CH3:1][N:2]1[CH2:3][C@@H:4]([OH:8])[CH2:5][CH2:6]1.ClC[Cl:17].ClC[Cl:7].O[C:15]([c:14]1[c:9](Cl)[n:10][cH:11][cH:12][cH:13]1)=[O:16]>>[CH3:1][N:2]1[CH2:3][C@H:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16].[ClH:17] | CN1CC[C@H](O)C1.ClCCl.ClCCl.O=C(O)c1cccnc1Cl | CN1C[C@H](CCCl)Oc2ncccc2C1=O.Cl | null | null | C(Cl)(Cl)(Cl)Cl.O1CCCC1.C(C)N(CC)CC | Acylation | OtherReaction | 76bfdfbaa3a00bac267fc4db8894135b9ecdf739c038e44eea9f6d5231d11211 | 429fdccab5d11c54310b7d1ab555bf74ea09e30d5ff456a6396b038c56ef2638 | O=C1NCCOc2ncccc21 | Cl-C-[Cl;H0;D1;+0:1].Cl-C-[Cl;H0;D1;+0:2].Cl-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[C;H0;D3;+0:7](-O)=[O;D1;H0:8]):[c:9].[C;D1;H3:10]-[N;H0;D3;+0:11]1-[C:12]-[C:13](-[OH;D1;+0:14])-[C:15]-[CH2;D2;+0:16]-1>>[C;D1;H3:10]-[N;H0;D3;+0:11]1-[C:12]-[C:13](-[C:15]-[CH2;D2;+0:16]-[Cl;H0;D1;+0:2])-[O;H0;D2;+0:14]-[c;H0;D3;+0:3... | null | [] | 25 | CELSIUS | null | null | A solution of 47.4 g (0.3 mole) of 2-chloronicotinic acid and 30 g (0.3 mole) of -(S)-1-methyl-3-pyrrolidinol in 400 ml of tetrahydrofuran was added over a period of 1 hr to a stirred suspension of 26.4 g (0.66 mole) of 60% sodium hydride)mineral oil in 500 ml of tetrahydrofuran at 50°-60° C. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary halide.Primary halide.Primary halide.Carboxylic acid.Secondary alcohol.Tertiary amine | Primary halide.Ether.Tertiary amide | C1CC[NH]C1.c1ccncc1 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | HCl | C(Cl)(Cl)(Cl)Cl.O1CCCC1.C(C)N(CC)CC | 25 | null | CN1CC[C@H](O)C1.ClCCl.ClCCl.O=C(O)c1cccnc1Cl>C(Cl)(Cl)(Cl)Cl.O1CCCC1.C(C)N(CC)CC>CN1C[C@H](CCCl)Oc2ncccc2C1=O.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a017fe39f254422c88213d2d48dce469 | CN1CC[C@@H](O)C1.ClCCl.ClCCl.O=C(O)c1cccnc1Cl>>CN1C[C@@H](CCCl)Oc2ncccc2C1=O.Cl | C(Cl)Cl.ClC1=C(C(=O)O)C=CC=N1.CN1C[C@@H](CC1)O.[H-].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CS(=O)(=O)O.C(Cl)Cl>>Cl.ClCC[C@H]1OC2=C(C(N(C1)C)=O)C=CC=N2 | [CH3:1][N:2]1[CH2:3][C@H:4]([OH:8])[CH2:5][CH2:6]1.ClC[Cl:17].ClC[Cl:7].O[C:15]([c:14]1[c:9](Cl)[n:10][cH:11][cH:12][cH:13]1)=[O:16]>>[CH3:1][N:2]1[CH2:3][C@@H:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]1=[O:16].[ClH:17] | CN1CC[C@@H](O)C1.ClCCl.ClCCl.O=C(O)c1cccnc1Cl | CN1C[C@@H](CCCl)Oc2ncccc2C1=O.Cl | null | null | C(C)N(CC)CC.O1CCCC1.C(Cl)(Cl)(Cl)Cl | Acylation | OtherReaction | 76bfdfbaa3a00bac267fc4db8894135b9ecdf739c038e44eea9f6d5231d11211 | 429fdccab5d11c54310b7d1ab555bf74ea09e30d5ff456a6396b038c56ef2638 | O=C1NCCOc2ncccc21 | Cl-C-[Cl;H0;D1;+0:1].Cl-C-[Cl;H0;D1;+0:2].Cl-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[C;H0;D3;+0:7](-O)=[O;D1;H0:8]):[c:9].[C;D1;H3:10]-[N;H0;D3;+0:11]1-[C:12]-[C:13](-[OH;D1;+0:14])-[C:15]-[CH2;D2;+0:16]-1>>[C;D1;H3:10]-[N;H0;D3;+0:11]1-[C:12]-[C:13](-[C:15]-[CH2;D2;+0:16]-[Cl;H0;D1;+0:2])-[O;H0;D2;+0:14]-[c;H0;D3;+0:3... | null | [] | 25 | CELSIUS | null | null | A solution of 47.4 g (0.3 mole) of 2-chloronicotinic acid and 30 g (0.3 mole) of (R)-1-methyl-3-pyrrolidinol in 400 ml of tetrahydrofuran was added over a period of 1 hr to a stirred suspension of 26.4 g (0.66 mole) of 60% sodium hydride/mineral oil in 500 ml of tetrahydrofuran at 55°-60° C. The mixture was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary halide.Primary halide.Primary halide.Carboxylic acid.Secondary alcohol.Tertiary amine | Primary halide.Ether.Tertiary amide | C1CC[NH]C1.c1ccncc1 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)N(CC)CC.O1CCCC1.C(Cl)(Cl)(Cl)Cl | 25 | null | CN1CC[C@@H](O)C1.ClCCl.ClCCl.O=C(O)c1cccnc1Cl>C(C)N(CC)CC.O1CCCC1.C(Cl)(Cl)(Cl)Cl>CN1C[C@@H](CCCl)Oc2ncccc2C1=O.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-726005ffdfda42c1af28a0e408d3d24e | CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=S | P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)[N+](=O)[O-].P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)[N+](=O)[O-] | O=[C:18]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:19])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]2[C:18]1=[S:19] | CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=S | null | null | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 43ac2affde81267970c96bfb182f28e85d876733ab6e6103821469d8ecc8ebf9 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | 173.5 | [{"value": 57.0, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 173.5, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 2.0 g (0.007 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-nitro-1,4-benzoxazepin-5(4H)-one in 35 ml of acetonitrile was added 1.0 g (0.0023 mole) of phosphorus pentasulfide and the mixture heated to reflux for 2 hr. Another 0.4 g (0.001 mole) of phosphorus pentasulfide was added and heating continued for 2 hr. ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | C(C)#N.C1(=CC=CC=C1)C | null | 2 | CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C(C)#N.C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-76a12ce959eb4171b4a538b09030f1f9 | CN1CC(CCCl)Oc2ccc(F)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CN1CC(CCCl)Oc2ccc(F)cc2C1=S | P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)F.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)F | O=[C:16]1[N:2]([CH3:1])[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]21.S=P12SP3(=S)SP(=S)(S1)SP(=[S:17])(S2)S3>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:7])[O:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][c:15]2[C:16]1=[S:17] | CN1CC(CCCl)Oc2ccc(F)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CN1CC(CCCl)Oc2ccc(F)cc2C1=S | null | null | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 43ac2affde81267970c96bfb182f28e85d876733ab6e6103821469d8ecc8ebf9 | 92373f703706fcd3b2fa077124e423e859506b3bebedf9bbb6de44eb68d5c891 | S=C1NCCOc2ccccc21 | O=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:9])(-S-2)-S-3>>[#8:8]-[c:7]:[c:5](:[c:6])-[C;H0;D3;+0:1](=[S;H0;D1;+0:9])-[#7:2](-[C;D1;H3:3])-[C:4] | 125.6 | [{"value": 52.0, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 125.6, "product": "ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 1.0 g (0.0039 mole) of 2-(2-chloroethyl)-2,3-dihydro-7-fluoro-4-methyl-1,4-benzoxazepin-5(4H)-one in 30 ml of acetonitrile was added 0.7 g (0.0016 mole) of phosphorus pentasulfide and the reaction mixture heated to reflux. After 2 hr, another 0.4 g (0.009 mole) of phosphorus pentasulfide was added and heating contin... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | c1ccc2c(c1)C[NH]CCO2.S1P2SP3SP1SP(S2)S3 | c1ccc2c(c1)C[NH]CCO2 | c1ccc2c(c1)C[NH]CCO2 | Other | C(C)#N.C1(=CC=CC=C1)C | null | 2 | CN1CC(CCCl)Oc2ccc(F)cc2C1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>C(C)#N.C1(=CC=CC=C1)C>CN1CC(CCCl)Oc2ccc(F)cc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-66c07ea6a9ef4116951cdf9662a6bd01 | CN1CC(CCCl)Oc2ccccc2C1=O.CNC>>CN(C)CCC1CN(C)C(=O)c2ccccc2O1.Cl | CNC.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=C2>>Cl.CN(CCC1OC2=C(C(N(C1)C)=O)C=CC=C2)C | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[O:18]1)[Cl:19].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[O:18]1.[ClH:19] | CN1CC(CCCl)Oc2ccccc2C1=O.CNC | CN(C)CCC1CN(C)C(=O)c2ccccc2O1.Cl | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCCOc2ccccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | 100 | CELSIUS | null | null | A solution of 9 g (0.2 mole) of dimethylamine in 250 ml of ethanol was added to 24 g (0.1 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)one in a steel bomb. The mixture was heated at 100° C. for 18 hrs. The solution was concentrated in vacuo and the residue partitioned between ethyl acetate and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2c(c1)C[NH]CCO2 | null | C(C)O | 100 | null | CN1CC(CCCl)Oc2ccccc2C1=O.CNC>C(C)O>CN(C)CCC1CN(C)C(=O)c2ccccc2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c7bfc234f1744f32ad7ffb0232bfef78 | CNC.O=C1c2ccccc2OC(CCCl)CN1Cc1ccccc1>>CN(C)CCC1CN(Cc2ccccc2)C(=O)c2ccccc2O1.O | C(C1=CC=CC=C1)N1CC(OC2=C(C1=O)C=CC=C2)CCCl.CNC>>O.C(C1=CC=CC=C1)N1CC(OC2=C(C1=O)C=CC=C2)CCN(C)C | [CH3:1][NH:2][CH3:3].Cl[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[O:24]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:... | CNC.O=C1c2ccccc2OC(CCCl)CN1Cc1ccccc1 | CN(C)CCC1CN(Cc2ccccc2)C(=O)c2ccccc2O1.O | null | null | null | Functional Group Interconversion | N-alkylation of secondary amines with alkyl halides | 105ac0dfe253fa64bb23e18afb1853920a6845d3c91bcb98534155cafd8aaf01 | da87afc172ebd302d462893afe878066c210a24130312f3acba00f6d41a889fd | O=C1c2ccccc2OCCN1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | null | null | null | null | Following the procedure of Example 1, 4-benzyl-2-(2-chloroethyl)-2,3-dihydro-1,4-benzoxazepin-5(4H)-one and dimethylamine were reacted and the free base of the title compound was obtained in the concentrated residue. Recrystallization from ethanol-water gave the product, m.p. 75°-77° C.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)C[NH]CCO2 | null | null | null | null | CNC.O=C1c2ccccc2OC(CCCl)CN1Cc1ccccc1>>CN(C)CCC1CN(Cc2ccccc2)C(=O)c2ccccc2O1.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b3d03018265147f9b16a7114a4128529 | CN1CC(CCCl)Oc2ncccc2C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2cccnc2O1 | C(\C=C\C(=O)O)(=O)O.CNC.C(C)O.ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2>>C(\C=C\C(=O)O)(=O)O.CN(CCC1OC2=C(C(N(C1)C)=S)C=CC=N2)C | Cl[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][cH:15][n:16][c:17]2[O:18]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][cH:15][n:16][c:17]2[O:18]1 | CN1CC(CCCl)Oc2ncccc2C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2cccnc2O1 | null | null | C(C)(C)O.CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | 100 | CELSIUS | null | null | To a solution of 113 ml (1.0 mole) of 40% aqueous dimethylamine and 326 ml of ethanol in a steel bomb was added 48.4 g (0.189 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione. The mixture was heated at 100° C. for 14 hr. The ethanol was removed in a rotary evaporator leaving some... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)(C)O.CO.C(Cl)Cl | 100 | null | CN1CC(CCCl)Oc2ncccc2C1=S.CNC>C(C)(C)O.CO.C(Cl)Cl>CN(C)CCC1CN(C)C(=S)c2cccnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7f21215b778f48b0850df62ea6fcc93a | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2ccc(Cl)cc2O1.Cl | ClC1=CC2=C(C(N(CC(O2)CCCl)C)=S)C=C1.CNC>>Cl.ClC1=CC2=C(C(N(CC(O2)CCN(C)C)C)=S)C=C1 | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[O:19]1)[Cl:20].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[O:19]1.[ClH:20] | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2ccc(Cl)cc2O1.Cl | null | null | C(C)O.Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2ccccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | A solution of 9.8 g (0.04 mole) of 8-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5 (4H)-thione in 50 ml of absolute ethanol and 10 ml of a 40% aqueous solution of dimethylamine were mixed and heated in a steel bomb at 100° C. for 16 hr. The ethanol was evaporated under reduced pressure and the resid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2c(c1)C[NH]CCO2 | null | C(C)O.Cl | null | null | CN1CC(CCCl)Oc2cc(Cl)ccc2C1=S.CNC>C(C)O.Cl>CN(C)CCC1CN(C)C(=S)c2ccc(Cl)cc2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9d16c145823b4fd287c4a6545f748c2d | CN1CC(CCCl)Oc2cnccc2C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2ccncc2O1.Cl | ClCCC1OC2=C(C(N(C1)C)=S)C=CN=C2.CNC>>Cl.CN(CCC1OC2=C(C(N(C1)C)=S)C=CN=C2)C | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][n:15][cH:16][c:17]2[O:18]1)[Cl:19].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][n:15][cH:16][c:17]2[O:18]1.[ClH:19] | CN1CC(CCCl)Oc2cnccc2C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2ccncc2O1.Cl | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2cnccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | To a solution of 0.5 g (0.002 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[4,3-f][1,4]-oxazepine-5(4H)-thione in 20 ml of ethyl alcohol was added 2 ml of 40% aqueous dimethylamine. The mixture was heated in a steel bomb to 100° C. for 14 hr. The resulting solution was filtered and concentrated. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cc2c(cn1)OCC[NH]C2 | null | C(C)O | null | null | CN1CC(CCCl)Oc2cnccc2C1=S.CNC>C(C)O>CN(C)CCC1CN(C)C(=S)c2ccncc2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-020326b1e4574d44986493bf5d683e46 | CCNCC.CN1CC(CCCl)Oc2ncccc2C1=S>>CCN(CC)CCC1CN(C)C(=S)c2cccnc2O1 | ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2.C(C)NCC>>C(C)N(CCC1OC2=C(C(N(C1)C)=S)C=CC=N2)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].Cl[CH2:6][CH2:7][CH:8]1[CH2:9][N:10]([CH3:11])[C:12](=[S:13])[c:14]2[cH:15][cH:16][cH:17][n:18][c:19]2[O:20]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH:8]1[CH2:9][N:10]([CH3:11])[C:12](=[S:13])[c:14]2[cH:15][cH:16][cH:17][n:18][c:19]2[O:20]1 | CCNCC.CN1CC(CCCl)Oc2ncccc2C1=S | CCN(CC)CCC1CN(C)C(=S)c2cccnc2O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C;D1;H3:9]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:6]-[C;D1;H3:5])-[C:8]-[C;D1;H3:9] | null | [] | null | null | null | null | 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione and diethylamine in ethanol are heated together to obtain the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)O | null | null | CCNCC.CN1CC(CCCl)Oc2ncccc2C1=S>C(C)O>CCN(CC)CCC1CN(C)C(=S)c2cccnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f2ced41ca80546fca5cc841a48e387ac | CN1CC(CCCl)Oc2ncccc2C1=O.CN1CC(CCl)Oc2ncccc2C1=O>>CN(C)CC1CN(C)C(=O)c2cccnc2O1 | ClCC1OC2=C(C(N(C1)C)=O)C=CC=N2.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2>>CN(C)CC1OC2=C(C(N(C1)C)=O)C=CC=N2 | O=C1c2cccnc2OC(CCCl)[CH2:3][N:2]1[CH3:1].Cl[CH2:4][CH:5]1[CH2:6][N:7]([CH3:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[O:17]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][N:7]([CH3:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[O:17]1 | CN1CC(CCCl)Oc2ncccc2C1=O.CN1CC(CCl)Oc2ncccc2C1=O | CN(C)CC1CN(C)C(=O)c2cccnc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cd18b0a1e34b5b148dbc523996cb1c11099777687f255297257557cddce67f0d | c3a337737fb112f6285f5fdfb311f31e44f8146f395929a52385b50ebe89346f | O=C1NCCOc2ncccc21 | Cl-C-C-C1-O-c2:n:c:c:c:c:2-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-1.Cl-[CH2;D2;+0:4]-[C:5](-[#8:6]-[c:7]:[#7;a:8])-[C:9]-[#7:10]>>[#7:10]-[C:9]-[C:5](-[CH2;D2;+0:4]-[N;H0;D3;+0:1](-[C;D1;H3:2])-[CH3;D1;+0:3])-[#8:6]-[c:7]:[#7;a:8] | null | [] | null | null | null | null | When in the procedure of Example 10, 2-chloromethyl-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one is substituted for 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one, the title compound is prepared and is isolated if desired as a pharmaceutically acceptable salt.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Tertiary amide | Tertiary amine | c1cnc2c(c1)C[NH]CCO2 | null | c1cnc2c(c1)C[NH]CCO2 | HCl | null | null | null | CN1CC(CCCl)Oc2ncccc2C1=O.CN1CC(CCl)Oc2ncccc2C1=O>>CN(C)CC1CN(C)C(=O)c2cccnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-2a5b54123d374a7f86084eaea7b0e18e | CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2ccc3ccccc3c2O1.Cl | ClCCC1OC2=C(C(N(C1)C)=S)C=CC1=CC=CC=C12.CNC>>Cl.CN(CCC1OC2=C(C(N(C1)C)=S)C=CC1=CC=CC=C12)C | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[c:21]2[O:22]1)[Cl:23].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[c:21]2[O:22]... | CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2ccc3ccccc3c2O1.Cl | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2c1ccc1ccccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | 20 | [{"value": 20.0, "product": "Cl.CN(CCC1OC2=C(C(N(C1)C)=S)C=CC1=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 15.0 g (0.05 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylnaphth[2,1-f][1,4]-oxazepine-5(4H)-thione in 50 ml of absolute ethanol was added 10 g of a 40% aqueous solution of dimethylamine. The resulting solution was heated in a steel bomb at 100° C. for 40 hr and concentrated under reduced pressure. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2c3c(ccc2c1)C[NH]CCO3 | null | C(C)O | null | null | CN1CC(CCCl)Oc2c(ccc3ccccc23)C1=S.CNC>C(C)O>CN(C)CCC1CN(C)C(=S)c2ccc3ccccc3c2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-899dfc4eb3d343fca6a7503b6a131990 | CN1CC(CCCl)Sc2ncccc2C1=O.CNC>>CN(C)CCC1CN(C)C(=O)c2cccnc2S1.Cl.Cl | CNC.ClCCC1SC2=C(C(N(C1)C)=O)C=CC=N2.CNC>>Cl.Cl.CN(CCC1SC2=C(C(N(C1)C)=O)C=CC=N2)C | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][n:16][c:17]2[S:18]1)[Cl:19].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][n:16][c:17]2[S:18]1.[ClH:19].[ClH:20] | CN1CC(CCCl)Sc2ncccc2C1=O.CNC | CN(C)CCC1CN(C)C(=O)c2cccnc2S1.Cl.Cl | null | null | null | Functional Group Addition | N-alkylation of secondary amines with alkyl halides | 6dc67fdaa84d3f88aea31bd6d36481dd1f7dd6caece2acc0ef2660765ea75733 | 44df6a34ed503be8d571d8a086699e2116e82b962d53e34ea90b7759e699f35c | O=C1NCCSc2ncccc21 | [#16:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#16:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | A solution of 1.5 g (0.0058 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one in 20 ml of dimethylamine was stirred at 25° C. in a sealed container for 72 hr. The excess dimethylamine was allowed to evaporate and the residue was partitioned between chloroform and dilute sodium hydrox... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCS2 | Other | null | null | null | CN1CC(CCCl)Sc2ncccc2C1=O.CNC>>CN(C)CCC1CN(C)C(=O)c2cccnc2S1.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-86d68c4097fe4b1490aca906d3daf585 | C1COCCN1.CN1CC(CCCl)Oc2ncccc2C1=O>>CN1CC(CCN2CCOCC2)Oc2ncccc2C1=O | C(C)(C)O.C(\C=C/C(=O)O)(=O)O.Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.N1CCOCC1.[OH-].[Na+]>>C(\C=C/C(=O)O)(=O)O.CN1CC(OC2=C(C1=O)C=CC=N2)CCN2CCOCC2 | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:20](=[O:21])[c:19]2[c:14]([n:15][cH:16][cH:17][cH:18]2)[O:13]1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[O:13][c:14]2[n:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21] | C1COCCN1.CN1CC(CCCl)Oc2ncccc2C1=O | CN1CC(CCN2CCOCC2)Oc2ncccc2C1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCC(CCN2CCOCC2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | null | [] | null | null | 8 | HOUR | 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one hydrochloride, 16 g (058 mole) was dissolved in morpholine (30 mL) and stirred overnight at room temperature. To the solution was added dilute sodium hydroxide solution (50 ml) and the resulting mixture extracted with chloroform (3×30 ml). The c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1cnc2c(c1)C[NH]CCO2 | HCl | null | null | 8 | C1COCCN1.CN1CC(CCCl)Oc2ncccc2C1=O>>CN1CC(CCN2CCOCC2)Oc2ncccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7df9808670ba4f2b81ba407bc9a2e80e | C1CCNC1.CN1CC(CCCl)Oc2ncccc2C1=O>>CN1CC(CCN2CCCC2)Oc2ncccc2C1=O | Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.N1CCCC1.[OH-].[Na+].C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.CN1CC(OC2=C(C1=O)C=CC=N2)CCN2CCCC2 | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:19](=[O:20])[c:18]2[c:13]([n:14][cH:15][cH:16][cH:17]2)[O:12]1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[O:12][c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[O:20] | C1CCNC1.CN1CC(CCCl)Oc2ncccc2C1=O | CN1CC(CCN2CCCC2)Oc2ncccc2C1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCC(CCN2CCCC2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[C:9]-[C:8]-1 | null | [] | 80 | CELSIUS | null | null | A sample of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one hydrochloride, 16 g (0.058 mole), was dissolved in 65 ml of pyrrolidine. The stirred solution was heated to 80° C. for 3 hr. The solution was cooled to room temperature and dilute sodium hydroxide solution (50 ml) was added. The re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1cnc2c(c1)C[NH]CCO2 | HCl | null | 80 | null | C1CCNC1.CN1CC(CCCl)Oc2ncccc2C1=O>>CN1CC(CCN2CCCC2)Oc2ncccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-78147b45cdc7467d8d67941c2d646da8 | CN1CC(CCCl)Oc2ncccc2C1=O.CNc1ccccc1>>CN1CC(CCN(C)c2ccccc2)Oc2ncccc2C1=O | Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.CNC1=CC=CC=C1>>CN1CC(OC2=C(C1=O)C=CC=N2)CCN(C2=CC=CC=C2)C | Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:22](=[O:23])[c:21]2[c:16]([n:17][cH:18][cH:19][cH:20]2)[O:15]1.[NH:7]([CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]([CH3:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[O:15][c:16]2[n:17][cH:18][cH:19][cH:20][c:21]2[C:22]... | CN1CC(CCCl)Oc2ncccc2C1=O.CNc1ccccc1 | CN1CC(CCN(C)c2ccccc2)Oc2ncccc2C1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCC(CCNc2ccccc2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:5])-[c:7](:[c:8]):[c:9] | 31 | [{"value": 31.0, "product": "CN1CC(OC2=C(C1=O)C=CC=N2)CCN(C2=CC=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 2 | DAY | 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one hydrochloride, 4.00 g (0.015 mole) was dissolved in N-methylaniline (30 ml) and heated to 95° C. with stirring for 2 days. Excess N-methylaniline was removed by rotary evaporation (95° C., vacuum pump). The residue was taken up in chloroform (80... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | HCl | null | 95 | 48 | CN1CC(CCCl)Oc2ncccc2C1=O.CNc1ccccc1>>CN1CC(CCN(C)c2ccccc2)Oc2ncccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d39ddbbc138844068577c6b89ab48ac7 | CC1CCCN1.CN1CC(CCCl)Oc2ncccc2C1=O>>CC1CCCN1CCC1CN(C)C(=O)c2cccnc2O1 | ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.CC1NCCC1>>CN1CC(OC2=C(C1=O)C=CC=N2)CCN2C(CCC2)C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6]1.Cl[CH2:7][CH2:8][CH:9]1[CH2:10][N:11]([CH3:12])[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][n:19][c:20]2[O:21]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH:9]1[CH2:10][N:11]([CH3:12])[C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][n:19][c:20]2[O:21]1 | CC1CCCN1.CN1CC(CCCl)Oc2ncccc2C1=O | CC1CCCN1CCC1CN(C)C(=O)c2cccnc2O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCC(CCN2CCCC2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:7]-[C:6]-1-[C;D1;H3:5] | 36.7 | [{"value": 36.7, "product": "CN1CC(OC2=C(C1=O)C=CC=N2)CCN2C(CCC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.7, "product": "CN1CC(OC2=C(C1=O)C=CC=N2)CCN2C(CCC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3.5 g (0.0145 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in ethanol (15 ml) was added 2-methyl pyrrolidine (5.0 g, 0.063 mole). The solution was heated to reflux for 3 hours with stirring. The ethanol was removed by rotary evaporation (water aspirator, 80° C.).... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)O | null | null | CC1CCCN1.CN1CC(CCCl)Oc2ncccc2C1=O>C(C)O>CC1CCCN1CCC1CN(C)C(=O)c2cccnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f51221a6b41343b3ae0995547573df97 | CN1CC(CCCl)Oc2ncccc2C1=O.c1cn[nH]c1>>CN1CC(CCn2cccn2)Oc2ncccc2C1=O | N1N=CC=C1.[H-].[Na+].N1N=CC=C1.N1N=CC=C1.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.[H-].[Na+]>>CN1CC(OC2=C(C1=O)C=CC=N2)CCN2N=CC=C2 | Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:19](=[O:20])[c:18]2[c:13]([n:14][cH:15][cH:16][cH:17]2)[O:12]1.[nH:7]1[cH:8][cH:9][cH:10][n:11]1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][n:7]2[cH:8][cH:9][cH:10][n:11]2)[O:12][c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[O:20] | CN1CC(CCCl)Oc2ncccc2C1=O.c1cn[nH]c1 | CN1CC(CCn2cccn2)Oc2ncccc2C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C1NCC(CCn2cccn2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[#7;a:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:1 | null | [] | null | null | 8 | HOUR | To a suspension of sodium hydride (1.2 g active, 0.05 mole) in dimethylformamide (15 ml) was added dropwise a solution of pyrazole (3.10 g, 0.045 mole) in dimethylformamide (15 ml). The resulting solution was then added to a solution of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one (9.12 g... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1cnc2c(c1)C[NH]CCO2 | HCl | CN(C=O)C | null | 8 | CN1CC(CCCl)Oc2ncccc2C1=O.c1cn[nH]c1>CN(C=O)C>CN1CC(CCn2cccn2)Oc2ncccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-db521c60394943f7aa9b07de7bbb410c | C1COCCN1.CN1CC(CCCl)Oc2ncccc2C1=S>>CN1CC(CCN2CCOCC2)Oc2ncccc2C1=S | ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2.N1CCOCC1>>CN1CC(OC2=C(C1=S)C=CC=N2)CCN2CCOCC2 | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:20](=[S:21])[c:19]2[c:14]([n:15][cH:16][cH:17][cH:18]2)[O:13]1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[O:13][c:14]2[n:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[S:21] | C1COCCN1.CN1CC(CCCl)Oc2ncccc2C1=S | CN1CC(CCN2CCOCC2)Oc2ncccc2C1=S | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCC(CCN2CCOCC2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | null | [] | null | null | 6 | HOUR | 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione, 4.5 g (0.018 mole) was dissolved in morpholine (30 ml). The solution was heated with stirring to 50°-60° C. for 6 hr. The morpholine was then removed by rotary evaporation (90° C., vacuum pump). The residue was taken up in chloroform (100 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1cnc2c(c1)C[NH]CCO2 | HCl | null | null | 6 | C1COCCN1.CN1CC(CCCl)Oc2ncccc2C1=S>>CN1CC(CCN2CCOCC2)Oc2ncccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-872233572f814beb868d5accde50c333 | CCN1CC(CCCl)Oc2ncccc2C1=S.CNC>>CCN1CC(CCN(C)C)Oc2ncccc2C1=S | Cl.ClCCC1OC2=C(C(N(C1)CC)=S)C=CC=N2.CNC.CNC>>CN(CCC1OC2=C(C(N(C1)CC)=S)C=CC=N2)C | Cl[CH2:7][CH2:6][CH:5]1[CH2:4][N:3]([CH2:2][CH3:1])[C:18](=[S:19])[c:17]2[c:12]([n:13][cH:14][cH:15][cH:16]2)[O:11]1.[NH:8]([CH3:9])[CH3:10]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH:5]([CH2:6][CH2:7][N:8]([CH3:9])[CH3:10])[O:11][c:12]2[n:13][cH:14][cH:15][cH:16][c:17]2[C:18]1=[S:19] | CCN1CC(CCCl)Oc2ncccc2C1=S.CNC | CCN1CC(CCN(C)C)Oc2ncccc2C1=S | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | null | null | 6 | DAY | 2-(2-Chloroethyl)-4-ethyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5(4H)-thione hydrochloride, 5.00 g (0.016 mole) was added to 20 ml of anhydrous dimethylamine. The reaction flask was sealed tightly and stirred at room temperature for 6 days. The flask was opened after cooling to 0° C. and dimethylamine allowed to evapor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | HCl | null | null | 144 | CCN1CC(CCCl)Oc2ncccc2C1=S.CNC>>CCN1CC(CCN(C)C)Oc2ncccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-9d782d8069744710b9a22aaa91c12169 | CNC.O=C1c2cccnc2OC(CCl)CN1C1CCCCC1>>CN(C)CC1CN(C2CCCCC2)C(=O)c2cccnc2O1 | ClCC1OC2=C(C(N(C1)C1CCCCC1)=O)C=CC=N2.ClCC1OC2=C(C(N(C1)C1CCCCC1)=O)C=CC=N2.CNC.C(C(=O)O)(=O)O>>C(C(=O)O)(=O)O.C1(CCCCC1)N1CC(OC2=C(C1=O)C=CC=N2)CN(C)C | [CH3:1][NH:2][CH3:3].Cl[CH2:4][CH:5]1[CH2:6][N:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]2[O:22]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][N:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]2[O:22... | CNC.O=C1c2cccnc2OC(CCl)CN1C1CCCCC1 | CN(C)CC1CN(C2CCCCC2)C(=O)c2cccnc2O1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2cccnc2OCCN1C1CCCCC1 | Cl-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4]:[#7;a:5])-[C:6]-[#7:7].[C;D1;H3:8]-[NH;D2;+0:9]-[C;D1;H3:10]>>[#7:7]-[C:6]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C;D1;H3:10])-[#8:3]-[c:4]:[#7;a:5] | null | [] | null | null | null | null | Utilizing the procedure of Example 10, 2-(chloromethyl-4-cyclohexyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5(4H)-one (Intermediate 35) is reacted with 40% aqueous dimethylamine and reacted with oxalic acid in isopropyl alcohol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | C1CCCCC1.c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)(C)O | null | null | CNC.O=C1c2cccnc2OC(CCl)CN1C1CCCCC1>C(C)(C)O>CN(C)CC1CN(C2CCCCC2)C(=O)c2cccnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-7051746fd05449e68d2d9950a4f789a1 | CN(C)CCC1CN(Cc2ccccc2)C(=O)c2cccnc2O1>>CN(C)CCC1CNC(=O)c2cccnc2O1 | [OH-].[Na+].C(C(=O)O)(=O)O.CN(C)CCC1OC2=C(C(N(C1)CC1=CC=CC=C1)=O)C=CC=N2.CN(C=O)C>>CN(CCC1OC2=C(C(NC1)=O)C=CC=N2)C | c1ccc(C[N:8]2[CH2:7][CH:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[O:17][c:16]3[c:11]([cH:12][cH:13][cH:14][n:15]3)[C:9]2=[O:10])cc1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[O:17]1 | CN(C)CCC1CN(Cc2ccccc2)C(=O)c2cccnc2O1 | CN(C)CCC1CNC(=O)c2cccnc2O1 | null | null | O | Deprotection | Hydrogenolysis of tertiary amines | b28a135fe3de6ff0ffbbf778b3863f5bc10e3bf8c4ba3b0b8ff8009777b68df1 | 34b1225b879c7cd6f415e82440353a2915ca55dd325d399a53ba925060397178 | O=C1NCCOc2ncccc21 | [#7;a:1]:[c:2]1:[c:3]-[C:4](=[O;D1;H0:5])-[N;H0;D3;+0:6](-C-c2:c:c:c:c:c:2)-[C:7]-[C:8]-[#8:9]-1>>[#7;a:1]:[c:2]1:[c:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7]-[C:8]-[#8:9]-1 | null | [] | null | null | 20 | MINUTE | A solution of 3.0 g (0.006 mole) of 2-[2-(dimethylamino ethyl]-2,3-dihydro-4-phenylmethylpyrido[3,2-f][1,4]oxazepin-5(4H)-one oxalate [1:1.5]-hemihydrate in about 50 ml of water was made basic with dilute aqueous sodium hydroxide solution and then extracted with three 50 ml portions of benzene. The combined benzene ext... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amide | c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)CNCCO2 | c1cnc2c(c1)CNCCO2 | Other | O | null | 0.333333 | CN(C)CCC1CN(Cc2ccccc2)C(=O)c2cccnc2O1>O>CN(C)CCC1CNC(=O)c2cccnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-689206cad7fa430599e0f8db786a2e2d | CN1CC(CCCl)Oc2ncccc2C1=O.Fc1ccc(C(c2ccc(F)cc2)C2CCNCC2)cc1.[OH-]>>CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=O.CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=O.Cl.Cl.Cl.O | Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.[OH-].[Na+].FC1=CC=C(C=C1)C(C1CCNCC1)C1=CC=C(C=C1)F>>O.Cl.Cl.FC1=CC=C(C=C1)C(C1CCN(CC1)CCC1OC2=C(C(N(C1)C)=O)C=CC=N2)C2=CC=C(C=C2)F.FC2=CC=C(C=C2)C(C2=CC=C(C=C2)F)C2CCN(CC2)CCC2OC1=C(C(N(C2)C)=O)C=CC=N1.Cl.Cl | [CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][Cl:73])[O:28][c:29]2[n:30][cH:31][cH:32][cH:33][c:34]2[C:35]1=[O:36].[NH:7]1[CH2:8][CH2:9][CH:10]([CH:11]([c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[c:41]2[cH:25][cH:24][c:22]([F:23])[cH:19][cH:40]2)[CH2:26][CH2:27]1.[OH-:64]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][... | CN1CC(CCCl)Oc2ncccc2C1=O.Fc1ccc(C(c2ccc(F)cc2)C2CCNCC2)cc1.[OH-] | CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=O.CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=O.Cl.Cl.Cl.O | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 5a09a210a0153885747da70f67cf1f581cd83591f7c50fe484bcc919fa5fb333 | f5c8bd4770c356b6e13d1a5ab63d3018ff9bf17614b67b80bcd2fa80c3297832 | O=C1NCC(CCN2CCC(C(c3ccccc3)c3ccccc3)CC2)Oc2ncccc21.O=C1NCC(CCN2CCC(C(c3ccccc3)c3ccccc3)CC2)Oc2ncccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[F;D1;H0:6]-[c;H0;D3;+0:7]1:[c:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10](-[CH;D3;+0:11](-[C:12]2-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-2)-[c:18](:[c:19]):[c:20]):[cH;D2;+0:21]:[cH;D2;+0:22]:1.[OH-;D0:23]>>[#7:24]-[C:25]-[CH;D3;+0:21](-[CH2;D2;+0:10]-[C:26]-[#7:27])-[O;H0;D2;+0... | null | [] | null | null | null | null | Ten grams (0.036 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepin-5-(4H)-one hydrochloride were partitioned between dilute sodium hydroxide and chloroform. The chloroform was dried over sodium sulfate and concentrated on the rotary evaporator. The residue was dissolved in 50 ml of ethanol and 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Secondary amine | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Tertiary amide.Tertiary amine.Tertiary amine | C1CCNCC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | null | C(Cl)(Cl)Cl | null | null | CN1CC(CCCl)Oc2ncccc2C1=O.Fc1ccc(C(c2ccc(F)cc2)C2CCNCC2)cc1.[OH-]>C(Cl)(Cl)Cl>CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=O.CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=O.Cl.Cl.Cl.O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-527d0d80a4d0427eaa7b5dca19829348 | CN1CC(CCCl)Oc2ncccc2C1=S.CNc1ccccc1>>CN1CC(CCN(C)c2ccccc2)Oc2ncccc2C1=S | ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2.CNC1=CC=CC=C1.CNC1=CC=CC=C1>>CN1CC(OC2=C(C1=S)C=CC=N2)CCN(C2=CC=CC=C2)C | Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:22](=[S:23])[c:21]2[c:16]([n:17][cH:18][cH:19][cH:20]2)[O:15]1.[NH:7]([CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]([CH3:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[O:15][c:16]2[n:17][cH:18][cH:19][cH:20][c:21]2[C:22]... | CN1CC(CCCl)Oc2ncccc2C1=S.CNc1ccccc1 | CN1CC(CCN(C)c2ccccc2)Oc2ncccc2C1=S | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCC(CCNc2ccccc2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:5])-[c:7](:[c:8]):[c:9] | null | [] | null | null | 2 | DAY | To a suspension of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione in 100 ml of toluene was added 11.49 g (0.11 mole) N-methylaniline and the mixture heated to reflux with stirring for 2 days (after approx. 6 hr, 23.0 g (0.22 mole) additional N-methylaniline was added). Toluene was remove... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | HCl | C1(=CC=CC=C1)C | null | 48 | CN1CC(CCCl)Oc2ncccc2C1=S.CNc1ccccc1>C1(=CC=CC=C1)C>CN1CC(CCN(C)c2ccccc2)Oc2ncccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ec03ce1100954ca0bec6d9b29d1c7ce8 | CCO.CN1CC(CCCl)Oc2ncccc2C1=S.Fc1ccc(C(c2ccc(F)cc2)C2CCNCC2)cc1.O=C([O-])[O-]>>CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=S.O.O=C(O)C(=O)O | ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2.FC1=CC=C(C=C1)C(C1CCNCC1)C1=CC=C(C=C1)F.C(C)O.C(=O)([O-])[O-].[K+].[K+]>>O.C(C(=O)O)(=O)O.FC1=CC=C(C=C1)C(C1CCN(CC1)CCC1OC2=C(C(N(C1)C)=S)C=CC=N2)C2=CC=C(C=C2)F | C([CH3:41])[OH:42].Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:35](=[S:36])[c:34]2[c:29]([n:30][cH:31][cH:32][cH:33]2)[O:28]1.[NH:7]1[CH2:8][CH2:9][CH:10]([CH:11]([c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1.[O-:37][C:39](=[O:38])[O-:40]>>[CH... | CCO.CN1CC(CCCl)Oc2ncccc2C1=S.Fc1ccc(C(c2ccc(F)cc2)C2CCNCC2)cc1.O=C([O-])[O-] | CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=S.O.O=C(O)C(=O)O | null | null | null | Acylation | OtherReaction | 2002116e767ae1e26b92e45d2c1e2d70fd1b71f5fd55b011d52b4f2b624197f7 | 1657da22b930a2f8cb24a0cf8f110142ca1524ba96790fa23a24272ddc03aeda | S=C1NCC(CCN2CCC(C(c3ccccc3)c3ccccc3)CC2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[CH3;D1;+0:5]-C-[OH;D1;+0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11].[O-;H0;D1:12]-[C;H0;D3;+0:13](-[O-;H0;D1:14])=[O;D1;H0:15]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11].[O;D1;H0:15]=[C;H0;D3;+0:13](-[OH;D1;+0:14])-[C;H0;D3;+0:5](-[O;D1;H1:16])=[O;H0... | null | [] | null | null | null | null | A solution of 4 g (0.016 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione and 4.5 g (0.016 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine in 100 ml of ethanol was refluxed for 48 hr. One gram of K2CO3 was added and this mixture stirred at reflux for 144 hr. The mixture was conc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | HCl | null | null | null | CCO.CN1CC(CCCl)Oc2ncccc2C1=S.Fc1ccc(C(c2ccc(F)cc2)C2CCNCC2)cc1.O=C([O-])[O-]>>CN1CC(CCN2CCC(C(c3ccc(F)cc3)c3ccc(F)cc3)CC2)Oc2ncccc2C1=S.O.O=C(O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-6d86f383aca44f438845b19594bf30af | CN1CC(CCCl)Oc2ncccc2C1=S.c1cn[nH]c1>>CN1CC(CCn2cccn2)Oc2ncccc2C1=S | ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2.[H-].[Na+].N1N=CC=C1.[H][H]>>CN1CC(OC2=C(C1=S)C=CC=N2)CCN2N=CC=C2 | Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:19](=[S:20])[c:18]2[c:13]([n:14][cH:15][cH:16][cH:17]2)[O:12]1.[nH:7]1[cH:8][cH:9][cH:10][n:11]1>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][n:7]2[cH:8][cH:9][cH:10][n:11]2)[O:12][c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[S:20] | CN1CC(CCCl)Oc2ncccc2C1=S.c1cn[nH]c1 | CN1CC(CCn2cccn2)Oc2ncccc2C1=S | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | S=C1NCC(CCn2cccn2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[#7;a:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:1 | null | [] | null | null | 8 | HOUR | To a suspension of 2.16 g (0.054 mole) of sodium hydride in 20 ml of dimethylformamide was added dropwise a solution of 2.92 g (0.043 mole) of pyrazole in 10 ml of dimethylformamide. There was a slight exotherm at this point with some evolution of hydrogen gas. The resulting solution was then added dropwise to a soluti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1cnc2c(c1)C[NH]CCO2 | HCl | CN(C=O)C | null | 8 | CN1CC(CCCl)Oc2ncccc2C1=S.c1cn[nH]c1>CN(C=O)C>CN1CC(CCn2cccn2)Oc2ncccc2C1=S |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a175c2df01544d719c07426ac8bda4f5 | CN1CC(C)(CCCl)Oc2ncccc2C1=O.CNC>>CN(C)CCC1(C)CN(C)C(=O)c2cccnc2O1.Cl | Cl.ClCCC1(OC2=C(C(N(C1)C)=O)C=CC=N2)C.CNC>>Cl.Cl.CN(CCC1(OC2=C(C(N(C1)C)=O)C=CC=N2)C)C | [CH2:4]([CH2:5][C:6]1([CH3:7])[CH2:8][N:9]([CH3:10])[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][n:17][c:18]2[O:19]1)[Cl:21].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][C:6]1([CH3:7])[CH2:8][N:9]([CH3:10])[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][n:17][c:18]2[O:19]1.[ClH:21] | CN1CC(C)(CCCl)Oc2ncccc2C1=O.CNC | CN(C)CCC1(C)CN(C)C(=O)c2cccnc2O1.Cl | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCCOc2ncccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | 67 | [{"value": 67.0, "product": "Cl.Cl.CN(CCC1(OC2=C(C(N(C1)C)=O)C=CC=N2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | DAY | To 4.5 g (0.015 mole) of 2-(2-chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one hydrochloride in 15 ml of methanol was added 40 ml of dimethylamine. The flask was sealed tightly and left standing at room temperature for 8 days. The methanol and dimethylamine were removed by rotary evaporation (7... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | null | CO | null | 192 | CN1CC(C)(CCCl)Oc2ncccc2C1=O.CNC>CO>CN(C)CCC1(C)CN(C)C(=O)c2cccnc2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-08923e8e29984bf08578bf990ca8b9ae | CN1CC(C)(CCCl)Oc2ncccc2C1=S.CNC>>CN(C)CCC1(C)CN(C)C(=S)c2cccnc2O1.Cl | ClCCC1(OC2=C(C(N(C1)C)=S)C=CC=N2)C.CNC>>Cl.CN(CCC1(OC2=C(C(N(C1)C)=S)C=CC=N2)C)C | [CH2:4]([CH2:5][C:6]1([CH3:7])[CH2:8][N:9]([CH3:10])[C:11](=[S:12])[c:13]2[cH:14][cH:15][cH:16][n:17][c:18]2[O:19]1)[Cl:20].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][C:6]1([CH3:7])[CH2:8][N:9]([CH3:10])[C:11](=[S:12])[c:13]2[cH:14][cH:15][cH:16][n:17][c:18]2[O:19]1.[ClH:20] | CN1CC(C)(CCCl)Oc2ncccc2C1=S.CNC | CN(C)CCC1(C)CN(C)C(=S)c2cccnc2O1.Cl | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2ncccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | 76 | [{"value": 76.0, "product": "Cl.CN(CCC1(OC2=C(C(N(C1)C)=S)C=CC=N2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | DAY | To a suspension of 4.5 g (0.017 mole) of 2-(2-chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 20 ml of methanol, cooled in an ice bath, was added 40 ml of dimethylamine. The flask was sealed tightly and left standing at room temperature for 10 days. The dimethylamine and methanol were r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | null | CO | null | 240 | CN1CC(C)(CCCl)Oc2ncccc2C1=S.CNC>CO>CN(C)CCC1(C)CN(C)C(=S)c2cccnc2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-d72b57dfc95c4cd685ec1dc1014cf8f3 | CC(Cl)CC1CN(C)C(=O)c2cccnc2O1.CNC>>CC(CC1CN(C)C(=O)c2cccnc2O1)N(C)C.Cl.Cl | CNC.[I-].[Na+].ClC(CC1OC2=C(C(N(C1)C)=O)C=CC=N2)C>>Cl.Cl.CN(C(CC1OC2=C(C(N(C1)C)=O)C=CC=N2)C)C | [CH3:1][CH:2]([CH2:3][CH:4]1[CH2:5][N:6]([CH3:7])[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][c:15]2[O:16]1)[Cl:20].[NH:17]([CH3:18])[CH3:19]>>[CH3:1][CH:2]([CH2:3][CH:4]1[CH2:5][N:6]([CH3:7])[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][c:15]2[O:16]1)[N:17]([CH3:18])[CH3:19].[ClH:20].[ClH:21] | CC(Cl)CC1CN(C)C(=O)c2cccnc2O1.CNC | CC(CC1CN(C)C(=O)c2cccnc2O1)N(C)C.Cl.Cl | null | null | null | Functional Group Addition | N-alkylation of secondary amines with alkyl halides | 6354b1816e35679ba45812db9d6cf0e2801e934ad90352b72a8e10c741b582a5 | de9d9c3ab30a40b38f20c962f47fd1d829290070ee492aec7c48aef2c08786f2 | O=C1NCCOc2ncccc21 | [#8:1]-[C:2]-[C:3]-[CH;D3;+0:4](-[C;D1;H3:5])-[Cl;H0;D1;+0:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[#8:1]-[C:2]-[C:3]-[CH;D3;+0:4](-[C;D1;H3:5])-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C;D1;H3:9].[ClH;D0;+0:6] | null | [] | null | null | 7 | DAY | Into a stainless steel bomb was placed 1.0 g sodium iodide, 5.0 g (0.017 mole) of 2-(2-chloropropyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one and 40 ml of dimethylamine. The bomb was sealed tightly, placed in the oven at 60° C. and rolled continuously for 7 days. The bomb was allowed to stand at room te... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | Other | null | null | 168 | CC(Cl)CC1CN(C)C(=O)c2cccnc2O1.CNC>>CC(CC1CN(C)C(=O)c2cccnc2O1)N(C)C.Cl.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f80487ff4d8a47d2b5d758272f0f2d59 | CC1CCCN1.CN1CC(CCCl)Oc2ncccc2C1=S>>CC(C)O.CC1CCCN1CCC1CN(C)C(=S)c2cccnc2O1 | C(\C=C\C(=O)O)(=O)O.CC1NCCC1.ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2.C([O-])([O-])=O.[K+].[K+]>>CC(C)O.C(\C=C\C(=O)O)(=O)O.CN1CC(OC2=C(C1=S)C=CC=N2)CCN2C(CCC2)C | [CH3:5][CH:6]1[CH2:7][CH2:8][CH2:9][NH:10]1.Cl[CH2:11][CH2:12][CH:13]1[CH2:14][N:15]([CH3:16])[C:17](=[S:18])[c:19]2[cH:20][cH:21][cH:22][n:23][c:24]2[O:25]1>>[CH3:1][CH:2]([CH3:3])[OH:4].[CH3:5][CH:6]1[CH2:7][CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH:13]1[CH2:14][N:15]([CH3:16])[C:17](=[S:18])[c:19]2[cH:20][cH:21][cH:22... | CC1CCCN1.CN1CC(CCCl)Oc2ncccc2C1=S | CC(C)O.CC1CCCN1CCC1CN(C)C(=S)c2cccnc2O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | da1dbf66ee826e6a6dceaca1e2898a33db23975104e256522dd31d3cfd809487 | 02e69e7344fdc40630a38a963004019f41856704aa70b506ccd14ac03983aa03 | S=C1NCC(CCN2CCCC2)Oc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:7]-[C:6]-1-[C;D1;H3:5] | 32.8 | [{"value": 16.4, "product": "CC(C)O.C(\\C=C\\C(=O)O)(=O)O.CN1CC(OC2=C(C1=S)C=CC=N2)CCN2C(CCC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "CC(C)O.C(\\C=C\\C(=O)O)(=O)O.CN1CC(OC2=C(C1=S)C=CC=N2)CCN2C(CCC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 5.0 g (0.019 mole) of 2-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 25 ml of absolute ethanol was added 3.5 g (0.04 mole) of 2-methylpyrrolidine. The mixture was heated to reflux for 6.5 hr and left standing at room temperature overnight. Mass spec and TLC showed pre... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1cnc2c(c1)C[NH]CCO2 | null | C(C)O | null | 8 | CC1CCCN1.CN1CC(CCCl)Oc2ncccc2C1=S>C(C)O>CC(C)O.CC1CCCN1CCC1CN(C)C(=S)c2cccnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-89054f1c59674f65a50d35bff9d091ac | C1COCCN1.CCN1CC(CCCl)N(C)c2ccccc2C1=O>>CCN1CC(CCN2CCOCC2)N(C)c2ccccc2C1=O | ClCCC1N(C2=C(C(N(C1)CC)=O)C=CC=C2)C.N1CCOCC1>>C(C)N1CC(N(C2=C(C1=O)C=CC=C2)C)CCN2CCOCC2 | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Cl[CH2:7][CH2:6][CH:5]1[CH2:4][N:3]([CH2:2][CH3:1])[C:22](=[O:23])[c:21]2[c:16]([cH:17][cH:18][cH:19][cH:20]2)[N:14]1[CH3:15]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[N:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:... | C1COCCN1.CCN1CC(CCCl)N(C)c2ccccc2C1=O | CCN1CC(CCN2CCOCC2)N(C)c2ccccc2C1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCC(CCN2CCOCC2)Nc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#7:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#7:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#8:5]-[C:6]-[C:7]-1 | 61 | [{"value": 61.0, "product": "C(C)N1CC(N(C2=C(C1=O)C=CC=C2)C)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 30 g (0.112 mole) of 2-(2-chloroethyl)-4-ethyl-1-methyl-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one in 70 ml of morpholine was refluxed for 3 hrs, concentrated on the rotary evaporator and the residue partitioned between chloroform and dilute sodium hydroxide. The chloroform was dried over anhydrous sod... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccc2c(c1)C[NH]CC[NH]2 | HCl | null | null | null | C1COCCN1.CCN1CC(CCCl)N(C)c2ccccc2C1=O>>CCN1CC(CCN2CCOCC2)N(C)c2ccccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-a24b688b91924da2b3f0df85caa2c0e1 | CC(C)N1CC(CCl)N(C)c2ccccc2C1=O.CNC>>CC(C)N1CC(CN(C)C)N(C)c2ccccc2C1=O | ClCC1N(C2=C(C(N(C1)C(C)C)=O)C=CC=C2)C.CNC>>CN1C(CN(C(C2=C1C=CC=C2)=O)C(C)C)CN(C)C | Cl[CH2:7][CH:6]1[CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:19](=[O:20])[c:18]2[c:13]([cH:14][cH:15][cH:16][cH:17]2)[N:11]1[CH3:12].[NH:8]([CH3:9])[CH3:10]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH:6]([CH2:7][N:8]([CH3:9])[CH3:10])[N:11]([CH3:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[O:20] | CC(C)N1CC(CCl)N(C)c2ccccc2C1=O.CNC | CC(C)N1CC(CN(C)C)N(C)c2ccccc2C1=O | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCCNc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3]-[#7:4])-[#7:5](-[C;D1;H3:6])-[c:7].[C;D1;H3:8]-[NH;D2;+0:9]-[C;D1;H3:10]>>[#7:4]-[C:3]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C;D1;H3:10])-[#7:5](-[C;D1;H3:6])-[c:7] | null | [] | 100 | CELSIUS | 15 | HOUR | A mixture of 5.0 g (0.02 mole) of 2-chloromethyl-1,2,3,4-tetrahydro-1-methyl-4-(1-methylethyl)-5H-1,4-benzodiazepin-5-one, and 15.0 g (0.45 mole) of dimethylamine, and 200 ml of methanol were placed in a steel bomb and heated and stirred at 100° C. for 15 hr. After concentrating in vacuo, the residue partitioned betwee... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2c(c1)C[NH]CC[NH]2 | HCl | CO | 100 | 15 | CC(C)N1CC(CCl)N(C)c2ccccc2C1=O.CNC>CO>CC(C)N1CC(CN(C)C)N(C)c2ccccc2C1=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-3f6dd8deeda549f8aafb1ee422df00da | CN.CNC.ClCC1CO1>>CNCC(O)CN(C)C.Cl | CNC.C(Cl)C1CO1.CN>>Cl.CN(CC(CNC)O)C | [CH3:1][NH2:2].[NH:7]([CH3:8])[CH3:9].[CH2:3]([CH:4]1[O:5][CH2:6]1)[Cl:10]>>[CH3:1][NH:2][CH2:3][CH:4]([OH:5])[CH2:6][N:7]([CH3:8])[CH3:9].[ClH:10] | CN.CNC.ClCC1CO1 | CNCC(O)CN(C)C.Cl | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | d22195cf4e7b9d5acfa6177d95cd3d6abea14a34c18d0a0dcafc33355b257996 | a7cbd855026b2ff6bc2fa326904381ca9eec04c82500bb354c2a8f9ee9c38c46 | null | [C;D1;H3:1]-[NH2;D1;+0:2].[C;D1;H3:3]-[NH;D2;+0:4]-[C;D1;H3:5].[Cl;H0;D1;+0:6]-[CH2;D2;+0:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C;D1;H3:1]-[NH;D2;+0:2]-[CH2;D2;+0:7]-[C:8](-[OH;D1;+0:10])-[CH2;D2;+0:9]-[N;H0;D3;+0:4](-[C;D1;H3:3])-[C;D1;H3:5].[ClH;D0;+0:6] | 84 | [{"value": 84.0, "product": "Cl.CN(CC(CNC)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Dimethylamine 22.6 g, 40% solution (0.2 mole) was added dropwise to a solution of 16 ml of epichlorohydrin (0.2 mole) in 100 ml of methanol at 5° C. stirring in an ice bath. After two hours at 5° C. a chilled solution of 86 ml methylamine of 40% solution (1 mole) was poured into the reaction mixture. Stirring was conti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine.Secondary amine | Secondary alcohol.Secondary amine.Tertiary amine | C1CO1 | null | null | null | CO | null | 1.5 | CN.CNC.ClCC1CO1>CO>CNCC(O)CN(C)C.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-5bc77dfd9e3c45db8eebc1805fbfa2fb | CN1CC(CCCl)Oc2c(ccc3cnccc23)C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2ccc3cnccc3c2O1.Cl | ClCCC1OC2=C3C=CN=CC3=CC=C2C(N(C1)C)=S.CNC>>Cl.CN(CCC1OC2=C3C=CN=CC3=CC=C2C(N(C1)C)=S)C | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]3[c:21]2[O:22]1)[Cl:23].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]3[c:21]2[O:22]1.... | CN1CC(CCCl)Oc2c(ccc3cnccc23)C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2ccc3cnccc3c2O1.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2c1ccc1cnccc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[7,6-f]isoquinoline-5(4H)-thione is reacted with dimethylamine to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cc2c3c(ccc2cn1)C[NH]CCO3 | null | null | null | null | CN1CC(CCCl)Oc2c(ccc3cnccc23)C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2ccc3cnccc3c2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-efef61e1c72e49098ec79ee2158eaa42 | CNC.Cc1cc2c(c3ncccc13)OC(CCCl)CN(C)C2=S>>Cc1cc2c(c3ncccc13)OC(CCN(C)C)CN(C)C2=S.Cl | ClCCC1OC2=C(C=C(C=3C=CC=NC23)C)C(N(C1)C)=S.CNC>>Cl.CN(CCC1OC2=C(C=C(C=3C=CC=NC23)C)C(N(C1)C)=S)C | [NH:16]([CH3:17])[CH3:18].[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]3[n:7][cH:8][cH:9][cH:10][c:11]13)[O:12][CH:13]([CH2:14][CH2:15][Cl:24])[CH2:19][N:20]([CH3:21])[C:22]2=[S:23]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]3[n:7][cH:8][cH:9][cH:10][c:11]13)[O:12][CH:13]([CH2:14][CH2:15][N:16]([CH3:17])[CH3:18])[CH2:19][N:20]([CH3:2... | CNC.Cc1cc2c(c3ncccc13)OC(CCCl)CN(C)C2=S | Cc1cc2c(c3ncccc13)OC(CCN(C)C)CN(C)C2=S.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2c1ccc1cccnc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4,7-dimethyl-1,4-oxazepino[6,7-h]quinoline-5(4H)-thione is reacted with dimethylamine to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c3c(ccc2c1)C[NH]CCO3 | null | null | null | null | CNC.Cc1cc2c(c3ncccc13)OC(CCCl)CN(C)C2=S>>Cc1cc2c(c3ncccc13)OC(CCN(C)C)CN(C)C2=S.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-b5c30907b10f4115832fbf4e0039c599 | CNC.Cc1ccc2ccc3c(c2n1)OC(CCCl)CN(C)C3=S>>Cc1ccc2ccc3c(c2n1)OC(CCN(C)C)CN(C)C3=S.Cl | ClCCC1OC2=C(C=CC=3C=CC(=NC23)C)C(N(C1)C)=S.CNC>>Cl.CN(CCC1OC2=C(C=CC=3C=CC(=NC23)C)C(N(C1)C)=S)C | [NH:16]([CH3:17])[CH3:18].[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]3[c:9]([c:10]2[n:11]1)[O:12][CH:13]([CH2:14][CH2:15][Cl:24])[CH2:19][N:20]([CH3:21])[C:22]3=[S:23]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]3[c:9]([c:10]2[n:11]1)[O:12][CH:13]([CH2:14][CH2:15][N:16]([CH3:17])[CH3:18])[CH2:19][N:20]([CH3:2... | CNC.Cc1ccc2ccc3c(c2n1)OC(CCCl)CN(C)C3=S | Cc1ccc2ccc3c(c2n1)OC(CCN(C)C)CN(C)C3=S.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2c1ccc1cccnc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4,10-dimethyl-1,4-oxazepino[6,7-h)quinoline-5(4H)-thione is reacted with dimethylamine to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c3c(ccc2c1)C[NH]CCO3 | null | null | null | null | CNC.Cc1ccc2ccc3c(c2n1)OC(CCCl)CN(C)C3=S>>Cc1ccc2ccc3c(c2n1)OC(CCN(C)C)CN(C)C3=S.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-1e3095902341438cbca43e09b1024cfd | CN1CC(CCCl)Oc2ccc3ncccc3c2C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2c(ccc3ncccc23)O1.Cl | ClCCC1OC=2C(=C3C=CC=NC3=CC2)C(N(C1)C)=S.CNC>>Cl.CN(CCC1OC=2C(=C3C=CC=NC3=CC2)C(N(C1)C)=S)C | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[c:13]([cH:14][cH:15][c:16]3[n:17][cH:18][cH:19][cH:20][c:21]23)[O:22]1)[Cl:23].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[c:13]([cH:14][cH:15][c:16]3[n:17][cH:18][cH:19][cH:20][c:21]23)[O:2... | CN1CC(CCCl)Oc2ccc3ncccc3c2C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2c(ccc3ncccc23)O1.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2ccc3ncccc3c21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | Following the procedure of Example 31, 4-(2-chloroethyl)-3,4-dihydro-2-methyl-[1,4]-oxazepino[6,7-f]quinoline-1(2H )-thione is reacted with dimethylamine to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2ccc3c(c2c1)C[NH]CCO3 | null | null | null | null | CN1CC(CCCl)Oc2ccc3ncccc3c2C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2c(ccc3ncccc23)O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c507885de2b74b8cbebd94b7d36d5089 | CN1CC(CCCl)Oc2c(ccc3cccnc23)C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2ccc3cccnc3c2O1.Cl | ClCCC1OC2=C(C=CC=3C=CC=NC23)C(N(C1)C)=S.CNC>>Cl.CN(CCC1OC2=C(C=CC=3C=CC=NC23)C(N(C1)C)=S)C | [CH2:4]([CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][n:19][c:20]3[c:21]2[O:22]1)[Cl:23].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][n:19][c:20]3[c:21]2[O:22]1.... | CN1CC(CCCl)Oc2c(ccc3cccnc23)C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2ccc3cccnc3c2O1.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2c1ccc1cccnc21 | [#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[Cl;H0;D1;+0:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8].[ClH;D0;+0:5] | null | [] | null | null | null | null | Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-h]quinoline-5(4H)-thione is reacted with dimethylamine to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c3c(ccc2c1)C[NH]CCO3 | null | null | null | null | CN1CC(CCCl)Oc2c(ccc3cccnc23)C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2ccc3cccnc3c2O1.Cl |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f1088ee455db457fb16d426fb9f3ae0f | C1CNC1.CN1CC(CCCl)Oc2ncccc2C1=O.CS(C)=O.O=C([O-])[O-]>>CN1CC(CCN2CCC2)Oc2ncccc2C1=O.O.O=C(O)C(=O)O | N1CCC1.N1CCC1.C([O-])([O-])=O.[K+].[K+].N1CCC1.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2.CS(=O)C>>O.C(C(=O)O)(=O)O.N1(CCC1)CCC1OC2=C(C(N(C1)C)=O)C=CC=N2 | [NH:7]1[CH2:8][CH2:9][CH2:10]1.Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:18](=[O:19])[c:17]2[c:12]([n:13][cH:14][cH:15][cH:16]2)[O:11]1.CS([CH3:24])=[O:25].[O-:20][C:22](=[O:21])[O-:23]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10]2)[O:11][c:12]2[n:13][cH:14][cH:15][cH:16][c:17]2[C:18]1=[O... | C1CNC1.CN1CC(CCCl)Oc2ncccc2C1=O.CS(C)=O.O=C([O-])[O-] | CN1CC(CCN2CCC2)Oc2ncccc2C1=O.O.O=C(O)C(=O)O | null | null | null | Acylation | OtherReaction | 77dbd28e1d288692e8933194a5fd7d4e881a291f523fe1b9f24a40a476a01050 | f282cae9af8040819d24c5fbca643165e020d58516afba86aaf6fb6ad76c90bd | O=C1NCC(CCN2CCC2)Oc2ncccc21 | C-S(-[CH3;D1;+0:1])=[O;H0;D1;+0:2].Cl-[CH2;D2;+0:3]-[C:4]-[C:5]-[#8:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1.[O-;H0;D1:11]-[C;H0;D3;+0:12](-[O-;H0;D1:13])=[O;D1;H0:14]>>[#8:6]-[C:5]-[C:4]-[CH2;D2;+0:3]-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1.[O;D1;H0:14]=[C;H0;D3;+0:12](-[OH;D1;+0:13])-[C;H0;D3;+0:1](-[O;D1;H1:15])=[O;H0;D1;... | null | [] | null | null | 4 | DAY | To a solution of 5.0 g (0.021 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one dissolved in 40 ml of dimethylsulfoxide was added 8.7 g (0.063 mole) of potassium carbonate followed by 1.40 g (0.025 mole) of azetidine. The mixture was stirred for 4 days at room temperature*. Another 0.5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Sulfoxide | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1cnc2c(c1)C[NH]CCO2 | HCl | null | null | 96 | C1CNC1.CN1CC(CCCl)Oc2ncccc2C1=O.CS(C)=O.O=C([O-])[O-]>>CN1CC(CCN2CCC2)Oc2ncccc2C1=O.O.O=C(O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-cad802f8607b497e826f6484b8b5dd8e | C1CNC1.C1CNC1.CN1CC(CCCl)Oc2ncccc2C1=S.CS(C)=O.O=C([O-])[O-]>>CN1CC(CCN2CCC2)Oc2ncccc2C1=S.O=C(O)/C=C/C(=O)O | N1CCC1.C([O-])([O-])=O.[K+].[K+].N1CCC1.ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2.CS(=O)C.N1CCC1>>C(\C=C\C(=O)O)(=O)O.N1(CCC1)CCC1OC2=C(C(N(C1)C)=S)C=CC=N2 | [NH:7]1[CH2:8][CH2:9][CH2:10]1.C1NC[CH2:24]1.Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:18](=[S:19])[c:17]2[c:12]([n:13][cH:14][cH:15][cH:16]2)[O:11]1.S(=[O:20])([CH3:21])[CH3:23].[O-:22][C:25](=[O:26])[O-:27]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10]2)[O:11][c:12]2[n:13][cH:14][cH:15][... | C1CNC1.C1CNC1.CN1CC(CCCl)Oc2ncccc2C1=S.CS(C)=O.O=C([O-])[O-] | CN1CC(CCN2CCC2)Oc2ncccc2C1=S.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | e6d9413339adaed3fb86a9b94839ebff98c94748362bf95d66420eca04c8c043 | 6716722ac7a12289371f78fe0a6508251281db471213d1dc2f1737480cf9e159 | S=C1NCC(CCN2CCC2)Oc2ncccc21 | C1-N-C-[CH2;D2;+0:1]-1.Cl-[CH2;D2;+0:2]-[C:3]-[C:4]-[#8:5].[CH3;D1;+0:6]-S(-[CH3;D1;+0:7])=[O;H0;D1;+0:8].[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-1.[O-;H0;D1:13]-[C;H0;D3;+0:14](-[O-;H0;D1:15])=[O;D1;H0:16]>>[#8:5]-[C:4]-[C:3]-[CH2;D2;+0:2]-[N;H0;D3;+0:12]1-[C:9]-[C:10]-[C:11]-1.[O;D1;H0:16]=[C;H0;D3;+0:14](-[OH;D1;+0:15])/... | 31 | [{"value": 31.0, "product": "C(\\C=C\\C(=O)O)(=O)O.N1(CCC1)CCC1OC2=C(C(N(C1)C)=S)C=CC=N2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To 5.0 g (0.0914 mole) of 2-(2-chloroethyl)-2,5-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione dissolved in 50 ml of dimethylsulfoxide was added 8.04 g (0.058 mole) of potassium carbonate and 1.21 g (0.021 mole) of azetidine. The reaction mixture was stirred at room temperature for 8 hr after which was added ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Secondary amine.Sulfoxide | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CNC1.C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1cnc2c(c1)C[NH]CCO2 | HCl | null | null | 8 | C1CNC1.C1CNC1.CN1CC(CCCl)Oc2ncccc2C1=S.CS(C)=O.O=C([O-])[O-]>>CN1CC(CCN2CCC2)Oc2ncccc2C1=S.O=C(O)/C=C/C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f16fdd29c044474da886cbfb04a2815b | CCNCC.CCOC(C)=O.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.CO.[OH-]>>CCN(CC)CCC1CN(C)C(=O)c2cc(Cl)cnc2O1.O=C(O)C(=O)O | C(C)OC(C)=O.CO.C(C)NCC.C(C)NCC.C(C)NCC.[OH-].[NH4+].ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O>>C(C(=O)O)(=O)O.ClC1=CC=2C(N(CC(OC2N=C1)CCN(CC)CC)C)=O | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].CC[O:27][C:25]([CH3:23])=[O:26].Cl[CH2:6][CH2:7][CH:8]1[CH2:9][N:10]([CH3:11])[C:12](=[O:13])[c:14]2[cH:15][c:16]([Cl:17])[cH:18][n:19][c:20]2[O:21]1.C[OH:22].[OH-:24]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH:8]1[CH2:9][N:10]([CH3:11])[C:12](=[O:13])[c:14]2[cH:15][c:16]([... | CCNCC.CCOC(C)=O.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.CO.[OH-] | CCN(CC)CCC1CN(C)C(=O)c2cc(Cl)cnc2O1.O=C(O)C(=O)O | null | null | C(C)O | Acylation | OtherReaction | 348c2faf84980bee9a4ac0d2546d922eeb25e7f323783ef33bbdb080267b5569 | 8c7a5897958746e817096e691bd5a0eaed0fcdfc28d5444735c68f8fbc5b17f6 | O=C1NCCOc2ncccc21 | C-C-[O;H0;D2;+0:1]-[C:2](-[CH3;D1;+0:3])=[O;D1;H0:4].C-[OH;D1;+0:5].Cl-[CH2;D2;+0:6]-[C:7]-[C:8]-[#8:9].[C;D1;H3:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C;D1;H3:14].[OH-;D0:15]>>[#8:9]-[C:8]-[C:7]-[CH2;D2;+0:6]-[N;H0;D3;+0:12](-[C:11]-[C;D1;H3:10])-[C:13]-[C;D1;H3:14].[O;D1;H0:4]=[C:2](-[OH;D1;+0:1])-[C;H0;D3;+0:3](=[O;H0;D1;... | 76 | [{"value": 76.0, "product": "C(C(=O)O)(=O)O.ClC1=CC=2C(N(CC(OC2N=C1)CCN(CC)CC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 2.26 ml (0.022 mole) of diethylamine and the mixture heated to reflux. (Complete dissolution occurred). After 1 hr, another 2.26 ml (0.022 mole) of diethylamine was added follow... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine.Methanol | Carboxylic acid.Carboxylic acid.Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)O | null | 1 | CCNCC.CCOC(C)=O.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.CO.[OH-]>C(C)O>CCN(CC)CCC1CN(C)C(=O)c2cc(Cl)cnc2O1.O=C(O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c8d4455c6b164a84bffaf46314b5819e | C1CNC1.C1CNC1.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.O=C([O-])[O-].[OH-]>>CN1CC(CCN2CCC2)Oc2ncc(Cl)cc2C1=O.O=C(O)C(=O)O | N1CCC1.[OH-].[NH4+].N1CCC1.ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O.C([O-])([O-])=O.[K+].[K+].N1CCC1>>C(C(=O)O)(=O)O.N1(CCC1)CCC1OC2=C(C(N(C1)C)=O)C=C(C=N2)Cl | [NH:7]1[CH2:8][CH2:9][CH2:10]1.C1NC[CH2:22]1.Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:19](=[O:20])[c:18]2[c:12]([n:13][cH:14][c:15]([Cl:16])[cH:17]2)[O:11]1.[O-:21][C:24](=[O:25])[O-:26].[OH-:23]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10]2)[O:11][c:12]2[n:13][cH:14][c:15]([Cl:16])[cH:1... | C1CNC1.C1CNC1.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.O=C([O-])[O-].[OH-] | CN1CC(CCN2CCC2)Oc2ncc(Cl)cc2C1=O.O=C(O)C(=O)O | null | null | CS(=O)C.CO.O.C(C)(=O)OCC | Acylation | OtherReaction | d65171afcf06fb0b281bb4e97894cbaf6fd8db7060487fd5c137c059ce31ba9c | c1d2c5ce311472318c38226bdf9a6dc42cc459acce751b23151f36da42111bd5 | O=C1NCC(CCN2CCC2)Oc2ncccc21 | C1-N-C-[CH2;D2;+0:1]-1.Cl-[CH2;D2;+0:2]-[C:3]-[C:4]-[#8:5].[C:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-1.[O-;H0;D1:10]-[C;H0;D3;+0:11](-[O-;H0;D1:12])=[O;D1;H0:13].[OH-;D0:14]>>[#8:5]-[C:4]-[C:3]-[CH2;D2;+0:2]-[N;H0;D3;+0:9]1-[C:6]-[C:7]-[C:8]-1.[O;D1;H0:13]=[C;H0;D3;+0:11](-[OH;D1;+0:12])-[C;H0;D3;+0:1](=[O;H0;D1;+0:10])-[OH;D1;+... | null | [] | null | null | 24 | HOUR | To a solution of 6 g (0.022 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one in 40 ml of dimethyl sulfoxide was added 8.0 g of crushed potassium carbonate and 1.5 g (0.026 mole) of azetidine. The reaction was stirred at room temperature for 24 hr. After checking ty TLC [7:2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CNC1.C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1cnc2c(c1)C[NH]CCO2 | HCl | CS(=O)C.CO.O.C(C)(=O)OCC | null | 24 | C1CNC1.C1CNC1.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.O=C([O-])[O-].[OH-]>CS(=O)C.CO.O.C(C)(=O)OCC>CN1CC(CCN2CCC2)Oc2ncc(Cl)cc2C1=O.O=C(O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-c3bc64bc129e484f957dfe469d616691 | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.NCCc1ccccc1.NCCc1ccccc1>>Cc1ccccc1CNC1CN(C)C(=O)c2cc(Cl)cnc2O1 | C(C1=CC=CC=C1)CN.C(C(=O)O)(=O)O.ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O.C(C1=CC=CC=C1)CN>>C(C(=O)O)(=O)O.ClC1=CC=2C(N(CC(OC2N=C1)NCC1=C(C=CC=C1)C)C)=O | ClCC[CH:10]1[CH2:11][N:12]([CH3:13])[C:14](=[O:15])[c:16]2[cH:17][c:18]([Cl:19])[cH:20][n:21][c:22]2[O:23]1.NC[CH2:8][c:7]1[cH:2][cH:3][cH:4][cH:5][cH:6]1.c1ccc([CH2:1]C[NH2:9])cc1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][NH:9][CH:10]1[CH2:11][N:12]([CH3:13])[C:14](=[O:15])[c:16]2[cH:17][c:18]([Cl:19])[cH:20... | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.NCCc1ccccc1.NCCc1ccccc1 | Cc1ccccc1CNC1CN(C)C(=O)c2cc(Cl)cnc2O1 | null | null | C(C)O.C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f4b44215ead1d0438d2bf11d21ce9c6f45fc759030e2e06357806e7c7da491fc | 0ee453ae46d68daf31d23066ef30b155c941f69bce1acdf87c9465ca7ffc7607 | O=C1NCC(NCc2ccccc2)Oc2ncccc21 | Cl-C-C-[CH;D3;+0:1](-[#8:2]-[c:3]:[#7;a:4])-[C:5]-[#7:6](-[C;D1;H3:7])-[C:8]=[O;D1;H0:9].N-C-[CH2;D2;+0:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15].[NH2;D1;+0:16]-C-[CH2;D2;+0:17]-c1:c:c:c:c:c:1>>[#7;a:4]:[c:3]-[#8:2]-[CH;D3;+0:1](-[NH;D2;+0:16]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](-[CH3;D1;+0:17]):[c:14]... | 47.9 | [{"value": 47.9, "product": "C(C(=O)O)(=O)O.ClC1=CC=2C(N(CC(OC2N=C1)NCC1=C(C=CC=C1)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6.0 g (0.022 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 5.3 g (0.044 mole) of benzylmethylamine and the mixture heated to reflux for three days. The solvent was removed by rotary evaporation, and the residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine.Primary amine | Ether.Secondary amine | c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1ccccc1 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)O.C(C)(C)O | null | null | CN1CC(CCCl)Oc2ncc(Cl)cc2C1=O.NCCc1ccccc1.NCCc1ccccc1>C(C)O.C(C)(C)O>Cc1ccccc1CNC1CN(C)C(=O)c2cc(Cl)cnc2O1 |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-708edbb82c3846ab9c16f701e9c84890 | C1CNC1.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=S.CS(C)=O.O=C([O-])[O-]>>CN1CC(CCN2CCC2)Oc2ncc(Cl)cc2C1=S.O=C(O)C(=O)O | N1CCC1.N1CCC1.ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=S.C([O-])([O-])=O.[K+].[K+].N1CCC1.CS(=O)C>>C(C(=O)O)(=O)O.N1(CCC1)CCC1OC2=C(C(N(C1)C)=S)C=C(C=N2)Cl | [NH:7]1[CH2:8][CH2:9][CH2:10]1.Cl[CH2:6][CH2:5][CH:4]1[CH2:3][N:2]([CH3:1])[C:19](=[S:20])[c:18]2[c:12]([n:13][cH:14][c:15]([Cl:16])[cH:17]2)[O:11]1.CS([CH3:24])=[O:25].[O:21]=[C:22]([O-:23])[O-:26]>>[CH3:1][N:2]1[CH2:3][CH:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10]2)[O:11][c:12]2[n:13][cH:14][c:15]([Cl:16])[cH:17][... | C1CNC1.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=S.CS(C)=O.O=C([O-])[O-] | CN1CC(CCN2CCC2)Oc2ncc(Cl)cc2C1=S.O=C(O)C(=O)O | null | null | O | Acylation | OtherReaction | 77dbd28e1d288692e8933194a5fd7d4e881a291f523fe1b9f24a40a476a01050 | f282cae9af8040819d24c5fbca643165e020d58516afba86aaf6fb6ad76c90bd | S=C1NCC(CCN2CCC2)Oc2ncccc21 | C-S(-[CH3;D1;+0:1])=[O;H0;D1;+0:2].Cl-[CH2;D2;+0:3]-[C:4]-[C:5]-[#8:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1.[O-;H0;D1:11]-[C;H0;D3;+0:12](-[O-;H0;D1:13])=[O;D1;H0:14]>>[#8:6]-[C:5]-[C:4]-[CH2;D2;+0:3]-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1.[O;D1;H0:14]=[C;H0;D3;+0:12](-[OH;D1;+0:11])-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[OH;D1;... | 82 | [{"value": 82.0, "product": "C(C(=O)O)(=O)O.N1(CCC1)CCC1OC2=C(C(N(C1)C)=S)C=C(C=N2)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 4.75 g (0.0164 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 40 ml of dimethyl sulfoxide was added 8.0 g of crushed potassium carbonate and 1.4 g (0.0246 mole) of azetidine. The flask was sealed and stirred at room temperature for 24 hr after which ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Sulfoxide | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1cnc2c(c1)C[NH]CCO2 | HCl | O | null | 24 | C1CNC1.CN1CC(CCCl)Oc2ncc(Cl)cc2C1=S.CS(C)=O.O=C([O-])[O-]>O>CN1CC(CCN2CCC2)Oc2ncc(Cl)cc2C1=S.O=C(O)C(=O)O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-ba780da7ad95459898e6dbacd6e9e38a | CNC.Cc1ccc2c(n1)OC(CCCl)CN(C)C2=O>>Cc1ccc2c(n1)OC(CCN(C)C)CN(C)C2=O | CNC.O.ClCCC1OC2=C(C(N(C1)C)=O)C=CC(=N2)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.CN(CCC1OC2=C(C(N(C1)C)=O)C=CC(=N2)C)C | [NH:12]([CH3:13])[CH3:14].Cl[CH2:11][CH2:10][CH:9]1[O:8][c:6]2[c:5]([cH:4][cH:3][c:2]([CH3:1])[n:7]2)[C:18](=[O:19])[N:16]([CH3:17])[CH2:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([n:7]1)[O:8][CH:9]([CH2:10][CH2:11][N:12]([CH3:13])[CH3:14])[CH2:15][N:16]([CH3:17])[C:18]2=[O:19] | CNC.Cc1ccc2c(n1)OC(CCCl)CN(C)C2=O | Cc1ccc2c(n1)OC(CCN(C)C)CN(C)C2=O | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCCOc2ncccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | null | null | 3 | DAY | To 50 ml of freshly collected dimethylamine was added 5.0 g (0.020 mole) of 2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one hydrate [1:1]. The reaction flask was sealed tightly and left standing at room temperature for 3 days. The dimethylamine was evaporated in a stream of air. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1cnc2c(c1)C[NH]CCO2 | HCl | C(C)(C)O | null | 72 | CNC.Cc1ccc2c(n1)OC(CCCl)CN(C)C2=O>C(C)(C)O>Cc1ccc2c(n1)OC(CCN(C)C)CN(C)C2=O |
ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | ord-f1df6ffd3002451e8e3a249fd7ae56eb | CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2cc([N+](=O)[O-])ccc2O1 | CNC.ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)[N+](=O)[O-]>>CN(CCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)[N+](=O)[O-])C | Cl[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20]2[O:21]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([CH3:9])[C:10](=[S:11])[c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20]2[O:21]1 | CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=S.CNC | CN(C)CCC1CN(C)C(=S)c2cc([N+](=O)[O-])ccc2O1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | S=C1NCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | null | null | 6 | DAY | To 50 ml of freshly collected dimethylamine was added 4.25 g (0.014 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-nitro-1,4-benzoxazepine-5(4H)-thione. The reaction flask was sealed tightly and allowed to stand at room temperature for 6 days. The dimethylamine was evaporated at room temperature. The solid residue w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2c(c1)C[NH]CCO2 | HCl | null | null | 144 | CN1CC(CCCl)Oc2ccc([N+](=O)[O-])cc2C1=S.CNC>>CN(C)CCC1CN(C)C(=S)c2cc([N+](=O)[O-])ccc2O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e7162987fc5047f0bed022391e7a5186 | O=S(=O)=O>>O=S(=O)=O | S(=O)(=O)=O.S(O)(O)(=O)=O>>OS(=O)(=O)O.O=S(=O)=O | [O:6]=[S:7](=[O:8])=[O:9]>>[O:6]=[S:7](=[O:8])=[O:9] | O=S(=O)=O | O=S(=O)=O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | FIG. 7 depicts a subunit for sulfuric acid. Liquid sulfur dioxide is supplied by a cylinder 121 to a fractionating column 122 and then to a membrane filter 123. The purified sulfur dioxide gas is then fed to a catalytic oxidizer 124 where it is combined with purified air 125 over a platinum or other suitable catalyst t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | O=S(=O)=O>>O=S(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-be3efbcf3dc141dc81dfa55a22b25b70 | O=C([O-])C1=NN(c2ccc(S(=O)(=O)[O-])cc2)C(=O)C1N=Nc1ccc(S(=O)(=O)[O-])cc1>>O=C1CCCN1C1CCCCC1 | C1=CC(=CC=C1N=NC2C(=NN(C2=O)C3=CC=C(C=C3)S(=O)(=O)[O-])C(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+]>>C1(CCCCC1)N1C(CCC1)=O | O=S(=O)([O-])c1ccc(N=N[CH:3]2[C:2](=[O:1])[N:6]([c:7]3[cH:8][cH:9][c:10](S(=O)(=O)[O-])[cH:11][cH:12]3)N=[C:4]2[C:5](=O)[O-])cc1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1 | O=C([O-])C1=NN(c2ccc(S(=O)(=O)[O-])cc2)C(=O)C1N=Nc1ccc(S(=O)(=O)[O-])cc1 | O=C1CCCN1C1CCCCC1 | null | null | O | Miscellaneous | OtherReaction | 48fd1a31d28002a4a8a1da1390fdad3f28d5625ad662f2c858b26fe70ce4c78e | 0b540714ee81d30a708af2c8e77ca9cf57ebbc61ca67680c6d13b9905ab53e84 | O=C1CCCN1C1CCCCC1 | O=[C;H0;D3;+0:1](-[O-])-[C;H0;D3;+0:2]1=N-[N;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-S(=O)(=O)-[O-]):[cH;D2;+0:8]:[cH;D2;+0:9]:2)-[C:10](=[O;D1;H0:11])-[CH;D3;+0:12]-1-N=N-c1:c:c:c(-S(=O)(=O)-[O-]):c:c:1>>[O;D1;H0:11]=[C:10]1-[CH2;D2;+0:12]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:3]-1-[CH... | null | [] | null | null | null | null | An ink composition comprising 2.5 percent by weight of Tartrazine FD&C Yellow #5, a yellow dye obtained from Buffalo Color, West Patterson, N.Y., 15 percent by weight of cyclohexyl pyrrolidone (obtained from GAF Corporation, Wayne, N.J.), and 82.5 percent by weight of deionized water was prepared by mixing together the... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Diazene.Sulfonic acid.Sulfonic acid | Tertiary amide | c1ccccc1.C1=N[NH]CC1.c1ccccc1 | C1CC[NH]C1.C1CCCCC1 | C1CC[NH]C1.C1CCCCC1 | Other | O | null | null | O=C([O-])C1=NN(c2ccc(S(=O)(=O)[O-])cc2)C(=O)C1N=Nc1ccc(S(=O)(=O)[O-])cc1>O>O=C1CCCN1C1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b1f4a5001bb04225b37898725e06c20d | CC(C)CC(C)O.Cc1ccccc1.OB(O)O>>CC(C)CC(C)OB(OC(C)CC(C)C)OC(C)CC(C)C | CC(CC(C)O)C.C1(=CC=CC=C1)C.B(O)(O)O>>B(OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C | [CH3:12][CH:13]([CH3:15])[CH2:19][CH:17]([OH:16])[CH3:18].[cH:1]1[cH:6][cH:5][cH:4][cH:2][c:10]1[CH3:11].O[B:8]([OH:7])[OH:9]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([CH3:6])[O:7][B:8]([O:9][CH:10]([CH3:11])[CH2:12][CH:13]([CH3:14])[CH3:15])[O:16][CH:17]([CH3:18])[CH2:19][CH:20]([CH3:21])[CH3:22] | CC(C)CC(C)O.Cc1ccccc1.OB(O)O | CC(C)CC(C)OB(OC(C)CC(C)C)OC(C)CC(C)C | null | null | O | C-C Coupling | OtherReaction | b0a8c44e3cf48ea1069e1a9c1beb6ed937cd51bf99523fdf580607d9cbf59326 | 7ccf8a4ec454d6cc03ce1e3efafa301b3c51d9e9635279e99312f4bc816939b8 | null | O-[B;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:3].[C;D1;H3:4]-[CH;D3;+0:5](-[CH3;D1;+0:6])-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])-[OH;D1;+0:10].[C;D1;H3:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[C;D1;H3:11]-[CH;D3;+0:12](-[CH2;D2;+0:6]-[CH;D3;+0:5](-[C;D1;H3:18])-[C;D1;H3:4])-... | null | [] | null | null | null | null | Approximately 306 grams of 4-methyl-2-pentanol, 100 grams of toluene, and 62 grams of boric acid were charged to a 2-liter glass reactor having an inert nitrogen atmosphere and equipped with heater, agitator, and Dean-Stark tube with condenser. The reactants were heated up to about 155° C. for a period of about 5 hours... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccccc1 | null | null | null | O | null | null | CC(C)CC(C)O.Cc1ccccc1.OB(O)O>O>CC(C)CC(C)OB(OC(C)CC(C)C)OC(C)CC(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c1c07a48db7345b6a7f46b1de4eb0229 | CCCCCCC(O)CCCCCCCCCCC(=O)O>>CCCCCCCCCCCCCCCCC(O)C(=O)[O-] | OC(CCCCCCCCCCC(=O)O)CCCCCC.[P].[S].[OH-].[Li+]>>OC(C(=O)[O-])CCCCCCCCCCCCCCCC.[Li+] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:19](=[O:20])[OH:21])[OH:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])[C:19](=[O:20])[O-:21] | CCCCCCC(O)CCCCCCCCCCC(=O)O | CCCCCCCCCCCCCCCCC(O)C(=O)[O-] | null | null | null | Functional Group Interconversion | OtherReaction | 9902cbf33697a1170a2502a73f5637431b7f1ab9f5d17966da97f339e3fc8c0d | 54cb95a546ba1fa58e84d50759a385f2264699bea86ea1ae67a3fdfe781ce107 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6].[C:7]-[C:8]-[CH;D3;+0:9](-[OH;D1;+0:10])-[C:11]-[C:12]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[C:11]-[C:12].[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:10])-[C:4](-[O-;H0;D1:6])=[O;D1;H0:5] | null | [] | null | null | null | null | A lithium hydroxystearate grease thickener was prepared by saponification of a mixture containing 12-hydroxystearic acid (50%) and the tri-glyceride thereof (25%) and 25% of C22 fatty acids containing no OH groups with lithium hydroxide in a mineral oil vehicle (ISO 150 viscosity grade of a 70/30 mixture of naphthenic ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Secondary alcohol | null | null | null | null | null | null | null | CCCCCCC(O)CCCCCCCCCCC(=O)O>>CCCCCCCCCCCCCCCCC(O)C(=O)[O-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c11e140ba9cd45de8bbf75d1cbd64d0a | C#Cc1ccc(OCC)cc1.Fc1ccc(I)cc1F>>CCOc1ccc(C#Cc2ccc(F)c(F)c2)cc1 | C(C)OC1=CC=C(C=C1)C#C.FC=1C=C(C=CC1F)I.C(C)N(CC)CC>>FC=1C=C(C=CC1F)C#CC1=CC=C(C=C1)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[CH:9])[cH:18][cH:19]1.I[c:10]1[cH:11][cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[C:9][c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]2)[cH:18][cH:19]1 | C#Cc1ccc(OCC)cc1.Fc1ccc(I)cc1F | CCOc1ccc(C#Cc2ccc(F)c(F)c2)cc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)(C)(C)OC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccc1)c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8]):[c:4]:[c:5] | null | [] | null | null | 2 | HOUR | 0.4 mmol of bis(triphenylphosphine)palladium(II) chloride and 0.2 mmol of CuI are added at room temperature to a mixture of 0.02 m of 4-ethoxyphenylacetylene, 0.02 m of 3,4-difluoroiodobenzene and 50 ml of triethylamine. The reaction mixture is stirred at room temperature for 2 hours, diluted with 100 ml of methyl tert... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(C)(C)OC | null | 2 | C#Cc1ccc(OCC)cc1.Fc1ccc(I)cc1F>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(C)(C)OC>CCOc1ccc(C#Cc2ccc(F)c(F)c2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f7a7c59d4cda43ec8f4e943cd1b919d7 | C#Cc1ccc(OCCCC)cc1.Fc1cc(Br)cc(F)c1F>>CCCCOc1ccc(C#Cc2cc(F)c(F)c(F)c2)cc1 | C(CCC)OC1=CC=C(C=C1)C#C.FC=1C=C(C=C(C1F)F)Br.C(C)N(CC)CC>>FC=1C=C(C=C(C1F)F)C#CC1=CC=C(C=C1)OCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[CH:11])[cH:21][cH:22]1.Br[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[cH:20]2)[cH:21][cH:22]1 | C#Cc1ccc(OCCCC)cc1.Fc1cc(Br)cc(F)c1F | CCCCOc1ccc(C#Cc2cc(F)c(F)c(F)c2)cc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)(C)(C)OC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8]):[c:4]:[c:5] | null | [] | null | null | 2 | HOUR | 0.4 mmol of bis(triphenylphosphine)palladium(II) chloride and 0.2 mmol of CuI are added at room temperature to a mixture of 0.02 m of 4-butoxyphenylacetylene, 0.02 m of 3,4,5-trifluorobromobenzene and 50 ml of triethylamine. The reaction mixture is stirred at room temperature for 2 hours, diluted with methyl tert.-buty... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(C)(C)OC | null | 2 | C#Cc1ccc(OCCCC)cc1.Fc1cc(Br)cc(F)c1F>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(C)(C)OC>CCCCOc1ccc(C#Cc2cc(F)c(F)c(F)c2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f5389a0b5ac54c3387a6aa94190a6c9c | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.N#Cc1ccc(C=O)cc1>>COC=Cc1ccc(C#N)cc1 | C(#N)C1=CC=C(C=O)C=C1.[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>COC=CC1=CC=C(C#N)C=C1 | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][O:2][CH3:1])cc1.O=[CH:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1>>[CH3:1][O:2][CH:3]=[CH:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1 | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.N#Cc1ccc(C=O)cc1 | COC=Cc1ccc(C#N)cc1 | null | null | COC(C)(C)C | C-C Coupling | Wittig with Phosphonium | 1b762435fe6b580b808a6e9f0dae00ddd254c0b88d607d21a223e11776d2e3a4 | bf4569804906d66c98adaac7df334e96eee508d45c26c621eb5069c3e4f1df77 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#8:6]-[CH2;D2;+0:7]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:5]-[#8:6]-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | A suspension of 37.2 g of methoxymethyl-triphenylphosphonium chloride in 250 ml of t-butyl methyl ether is treated at room temperature while gassing with argon with 13.4 g of potassium t-butylate and stirred for 1 hour. Subsequently, the reaction mixture is treated at about 20° C. with a mixture of 9.49 g of 4-cyanoben... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Ether | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | COC(C)(C)C | null | 1 | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.N#Cc1ccc(C=O)cc1>COC(C)(C)C>COC=Cc1ccc(C#N)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cad7b00ba5724d598c933c5d285d2c46 | COC=C(C=O)c1ccc(C#N)cc1.N=C(N)c1ccc(C(N)=O)cc1>>N#Cc1ccc(-c2cnc(-c3ccc(C(N)=O)cc3)nc2)cc1 | Cl.C(N)(=N)C1=CC=C(C(=O)N)C=C1.[Na].C(#N)C1=CC=C(C=C1)C(C=O)=COC>>C(#N)C1=CC=C(C=C1)C=1C=NC(=NC1)C1=CC=C(C(=O)N)C=C1 | CO[CH:21]=[C:7]([c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:23][cH:22]1)[CH:8]=O.[NH2:9][C:10]([c:11]1[cH:12][cH:13][c:14]([C:15]([NH2:16])=[O:17])[cH:18][cH:19]1)=[NH:20]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([NH2:16])=[O:17])[cH:18][cH:19]3)[n:20][cH:21]2)[cH:22]... | COC=C(C=O)c1ccc(C#N)cc1.N=C(N)c1ccc(C(N)=O)cc1 | N#Cc1ccc(-c2cnc(-c3ccc(C(N)=O)cc3)nc2)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 7ff619bc6b8105d6a50f08652202021c7036772b44111654e9ca09f6e0092ca4 | 5e1c8e4021bf83ca9a2cb1d1e6032536755277517375e5fd4bee10b9e4aead67 | c1ccc(-c2cnc(-c3ccccc3)nc2)cc1 | C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[C;H0;D3;+0:10](=[NH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[c:14]:[c:13]:[c;H0;D3;+0:12](-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[c... | null | [] | null | null | 2 | HOUR | 247 mg of sodium are treated at room temperature with 10 ml of methanol. After 15 minutes the solution obtained is treated at room temperature with 1.58 g of 4-amidinobenzamide hydrochloride. A white suspension forms and this is treated dropwise at room temperature within 10 minutes with a solution of 1.42 g of 2-(4-cy... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine | null | null | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | CO | null | 2 | COC=C(C=O)c1ccc(C#N)cc1.N=C(N)c1ccc(C(N)=O)cc1>CO>N#Cc1ccc(-c2cnc(-c3ccc(C(N)=O)cc3)nc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-66dbc3d515fb4644a721ff89c761de7f | [Ag+]>>[Ag] | [N+](=O)([O-])[O-].[Ag+].N.N1N=NC2=C1C=CC=C2>>N1N=NC2=C1C=CC=C2.[Ag] | [Ag+:1]>>[Ag:1] | [Ag+] | [Ag] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Ag+;H0;D0:1]>>[Ag;H0;D0;+0:1] | null | [] | null | null | null | null | Prepared by mixing simultaneously an ammoniacal silver nitrate aqueous solution and bendotriazole (containing 0.2 mol % of aqueous ammonia per mol benzotriazole) into a 10%-aqueous solution of phenylcarbamoyl gelatin of 50° C. After completing the addition, the pH was reduced and then flocculation and desalting were ca... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | [Ag+]>>[Ag] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1552f7df163c4dd28c6db945c2a62da2 | CCC(C)(C)c1ccc(OCC(CNC(=O)c2cc(C(=O)NCC(COc3ccc(C(C)(C)CC)cc3)C(C)(C)CC)cc(S(=O)(=O)Cl)c2)C(C)(C)CC)cc1>>CCC(C)(C)c1ccc(OCC(CNC(=O)c2cc(C(=O)NCC(COc3ccc(C(C)(C)CC)cc3)C(C)(C)CC)cc(S(=O)[O-])c2)C(C)(C)CC)cc1 | C(C)(C)(CC)C(CNC(=O)C=1C=C(C=C(C1)C(NCC(COC1=CC=C(C=C1)C(C)(C)CC)C(C)(C)CC)=O)S(=O)(=O)Cl)COC1=CC=C(C=C1)C(C)(C)CC.S(=O)([O-])[O-].[Na+].[Na+].C(O)([O-])=O.[Na+].O>>C(C)(C)(CC)C(CNC(=O)C=1C=C(C=C(C1)C(NCC(COC1=CC=C(C=C1)C(C)(C)CC)C(C)(C)CC)=O)S(=O)[O-])COC1=CC=C(C=C1)C(C)(C)CC.[Na+] | Cl[S:45]([c:44]1[cH:43][c:19]([C:20](=[O:21])[NH:22][CH2:23][CH:24]([CH2:25][O:26][c:27]2[cH:28][cH:29][c:30]([C:31]([CH3:32])([CH3:33])[CH2:34][CH3:35])[cH:36][cH:37]2)[C:38]([CH3:39])([CH3:40])[CH2:41][CH3:42])[cH:18][c:17]([C:15]([NH:14][CH2:13][CH:12]([CH2:11][O:10][c:9]2[cH:8][cH:7][c:6]([C:3]([CH2:2][CH3:1])([CH3... | CCC(C)(C)c1ccc(OCC(CNC(=O)c2cc(C(=O)NCC(COc3ccc(C(C)(C)CC)cc3)C(C)(C)CC)cc(S(=O)(=O)Cl)c2)C(C)(C)CC)cc1 | CCC(C)(C)c1ccc(OCC(CNC(=O)c2cc(C(=O)NCC(COc3ccc(C(C)(C)CC)cc3)C(C)(C)CC)cc(S(=O)[O-])c2)C(C)(C)CC)cc1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 65bd520d46095381b97cf2b1c808b198594dded087e2637f2dbe5add6a47838a | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=C(NCCCOc1ccccc1)c1cccc(C(=O)NCCCOc2ccccc2)c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[O-;H0;D1:3]-[S;H0;D3;+0:1](=[O;D1;H0:2])-[c:4](:[c:5]):[c:6] | 82.8 | [{"value": 82.8, "product": "C(C)(C)(CC)C(CNC(=O)C=1C=C(C=C(C1)C(NCC(COC1=CC=C(C=C1)C(C)(C)CC)C(C)(C)CC)=O)S(=O)[O-])COC1=CC=C(C=C1)C(C)(C)CC.[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "C(C)(C)(CC)C(CNC(=O)C=1C=C(C=C(C1)C(NCC(COC1=CC=C(C=C1)C(C)(C)CC)C(C)(C)CC)=O)S(=O)[O-])COC1=... | 30 | CELSIUS | null | null | To 2 g (0.016 mol) of sodium sulfite and 2.4 g (0.029 mol) of sodium hydrogen carbonate were added 100 ml of water and 20 ml of acetonitrile and the mixture was stirred at 30° C. To the mixture was added dropwise a solution of 10.5 g (0.013 mol) of 3,5-di-(2,4-di-tert-amylphenoxypropylcarbamoyl)benzenesulfonyl chloride... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)#N | 30 | null | CCC(C)(C)c1ccc(OCC(CNC(=O)c2cc(C(=O)NCC(COc3ccc(C(C)(C)CC)cc3)C(C)(C)CC)cc(S(=O)(=O)Cl)c2)C(C)(C)CC)cc1>C(C)#N>CCC(C)(C)c1ccc(OCC(CNC(=O)c2cc(C(=O)NCC(COc3ccc(C(C)(C)CC)cc3)C(C)(C)CC)cc(S(=O)[O-])c2)C(C)(C)CC)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1d5819da44804bb79114f5102ded9ad5 | CCCCCCCCCCCCCCCCOC(=O)c1cc(C(=O)OCCCCCCCCCCCCCCCC)cc(S(=O)(=O)Cl)c1.O>>CCCCCCCCCCCCCCCCOC(=O)c1cc(C(=O)OCCCCCCCCCCCCCCCC)cc(S(=O)(=O)O)c1 | C(CCCCCCCCCCCCCCC)OC(=O)C=1C=C(C=C(C1)C(=O)OCCCCCCCCCCCCCCCC)S(=O)(=O)Cl.O.Cl>>C(CCCCCCCCCCCCCCC)OC(=O)C=1C=C(C=C(C1)C(=O)OCCCCCCCCCCCCCCCC)S(=O)(=O)O | Cl[S:44]([c:43]1[cH:42][c:22]([C:23](=[O:24])[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[cH:21][c:20]([C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][... | CCCCCCCCCCCCCCCCOC(=O)c1cc(C(=O)OCCCCCCCCCCCCCCCC)cc(S(=O)(=O)Cl)c1.O | CCCCCCCCCCCCCCCCOC(=O)c1cc(C(=O)OCCCCCCCCCCCCCCCC)cc(S(=O)(=O)O)c1 | null | [Zn] | C(Cl)(Cl)Cl | Acylation | OtherReaction | 1eafc1aae6c14d9972cab5f3920901c9514a0be256331ee344fa90a3f3cbb637 | 0a58714a63276a8fe8849940eeb9a2ea532cac0a306d322fd1d3946a4729fe01 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[OH2;D0;+0:7]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[OH;D1;+0:7])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | MINUTE | 87 ml of water and 18.2 ml (0.218 mol) of 12N-HCl were added to the solution of 87 ml of chloroform and 8.65 g (0.0121 mol) of the white solid containing 3,5-dihexadecyloxycarbonylbenzenesulfonyl chloride, and then 7.93 g of zinc was added thereto at 5° C. followed by stirring for 4 hours and 30 minutes. After the inso... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonic acid | null | null | c1ccccc1 | HCl | [Zn].C(Cl)(Cl)Cl | null | 0.5 | CCCCCCCCCCCCCCCCOC(=O)c1cc(C(=O)OCCCCCCCCCCCCCCCC)cc(S(=O)(=O)Cl)c1.O>[Zn].C(Cl)(Cl)Cl>CCCCCCCCCCCCCCCCOC(=O)c1cc(C(=O)OCCCCCCCCCCCCCCCC)cc(S(=O)(=O)O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0efa13a49ba14cf48bbde9a169b7b718 | CCCCCCCCCCCCc1ccc(O)cc1O.O=Nc1ccc(O)cc1O>>CCCCCCCCCCCCc1cc2nc3ccc(O)cc3oc-2cc1=O | C(CCCCCCCCCCC)C1=C(C=C(O)C=C1)O.N(=O)C1=C(C=C(O)C=C1)O>>C(CCCCCCCCCCC)C1=CC2=NC3=CC=C(C=C3OC2=CC1=O)O | O[c:25]1[cH:15][cH:14][c:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:27]([OH:28])[cH:26]1.O=[N:16][c:17]1[cH:18][cH:19][c:20]([OH:21])[cH:22][c:23]1[OH:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][c:15]2[n:1... | CCCCCCCCCCCCc1ccc(O)cc1O.O=Nc1ccc(O)cc1O | CCCCCCCCCCCCc1cc2nc3ccc(O)cc3oc-2cc1=O | null | null | S(O)(O)(=O)=O | Aromatic Heterocycle Formation | OtherReaction | feeaff925a6fe0f956d6a39e6fb8aff7991b05d71d2117702fc196a2ef8c74c6 | 5f9d020af144bb530e68224e7a66d6a00fa1eddb8435fb4807edcffd80f1584a | O=c1ccc2nc3ccccc3oc-2c1 | O-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-[OH;D1;+0:4]):[c:5](-[C:6]):[c:7]:[cH;D2;+0:8]:1.O=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[C:6]-[c:5]1:[c:7]:[c;H0;D3;+0:8]2:[n;H0;D2;+0:9]:[c:10](:[c:11]):[c:12](:[c:14]):[o;H0;D2;+0:13]:[c;H0;D3;+0:1]-2:[c:2]:[c;H0;D3;+0:3]:1=[O;H0;D1;+0:4] | 47.9 | [{"value": 47.9, "product": "C(CCCCCCCCCCC)C1=CC2=NC3=CC=C(C=C3OC2=CC1=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A solution of 4-dodecylresorcinol (8.5 g, 30.53 mmole) (Aldrich Chemical Company) and 4-nitrosoresorcinol (5.0 g, 35.9 mmole) (Aldrich) in concentrated sulfuric acid (100 mL) is heated to 67° C. with stirring for 5 hours. The reaction mixture is allowed to cool to room temperature, poured into ice-water (1800 mL) and f... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | null | c1ccccc1.c1ccccc1 | c1ccc2oc3ccccc3nc2c1 | c1ccc2oc3ccccc3nc2c1 | HO- | S(O)(O)(=O)=O | null | 5 | CCCCCCCCCCCCc1ccc(O)cc1O.O=Nc1ccc(O)cc1O>S(O)(O)(=O)=O>CCCCCCCCCCCCc1cc2nc3ccc(O)cc3oc-2cc1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-524d531152204c2e8e6ceed8643f94a1 | CC(=O)OCC1O[C@H](Br)C(OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O.CCCCCCCCCCCCCCCCCCc1cc2nc3ccc(O)cc3oc-2cc1=O>>CCCCCCCCCCCCCCCCCCc1cc2nc3ccc(O[C@@H]4O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]4OC(C)=O)cc3oc-2cc1=O | OC=1C=C2OC3=CC(C(=CC3=NC2=CC1)CCCCCCCCCCCCCCCCCC)=O.CC1=CC(=NC(=C1)C)C.CC(=O)OCC1[C@@H]([C@@H](C([C@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C>>C(CCCCCCCCCCCCCCCCC)C1=CC2=NC3=CC=C(C=C3OC2=CC1=O)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](O1)COC(C)=O | Br[C@H:28]1[O:29][CH:30]([CH2:31][O:32][C:33]([CH3:34])=[O:35])[C@H:36]([O:37][C:38]([CH3:39])=[O:40])[C@H:41]([O:42][C:43]([CH3:44])=[O:45])[CH:46]1[O:47][C:48]([CH3:49])=[O:50].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][c:19]... | CC(=O)OCC1O[C@H](Br)C(OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O.CCCCCCCCCCCCCCCCCCc1cc2nc3ccc(O)cc3oc-2cc1=O | CCCCCCCCCCCCCCCCCCc1cc2nc3ccc(O[C@@H]4O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]4OC(C)=O)cc3oc-2cc1=O | null | C([O-])([O-])=O.[Ag+2] | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 10bc97c5591dffc70f58b8342cb03eebbb174e9f252bf00557248c38c5c8d459 | 55080db572a904fc27b88d797c7a6e2b661ffe3650c92412a40a3b49e5a4d963 | O=c1ccc2nc3ccc(O[C@H]4CCCCO4)cc3oc-2c1 | Br-[C@H;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5](-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[CH;D3;+0:10]-1-[#8:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14].[#8;a:15]:[c:16]:[c:17]:[c:18](-[OH;D1;+0:19]):[c:20]>>[#8;a:15]:[c:16]:[c:17]:[c:18](-[O;H0;D2;+0:19]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5](-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1... | null | [] | null | null | 1 | HOUR | A mixture of 7-hydroxy-2-octadecyl-3H-phenoxazine-3-one ("octadecylresorufin) (220 mg, 0.47 mmole), powdered, activated 4Å molecular sieves (0.5 g), sym-collidine (125 μL, 0.95 mmole), and silver carbonate (155 mg, 0.56 mmole) in dry dichloromethane (20 mL) is allowed to stir at room temperature, under an atmosphere of... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether.Aromatic alcohol | Ether.Ether | C1CCOCC1 | C1CCOCC1 | c1ccc2oc3ccccc3nc2c1.C1CCOCC1 | HBr | C([O-])([O-])=O.[Ag+2].ClCCl | null | 1 | CC(=O)OCC1O[C@H](Br)C(OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O.CCCCCCCCCCCCCCCCCCc1cc2nc3ccc(O)cc3oc-2cc1=O>C([O-])([O-])=O.[Ag+2].ClCCl>CCCCCCCCCCCCCCCCCCc1cc2nc3ccc(O[C@@H]4O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]4OC(C)=O)cc3oc-2cc1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-24c840048e664bd5a56761d42d4b423b | O=C1CCC(=O)O1.Oc1cccc(O)c1>>O=C(O)CC=C1c2ccc(O)cc2Oc2cc(O)ccc21 | C1(O)=CC(O)=CC=C1.C1(CCC(=O)O1)=O>>C(=O)(O)CC=C1C2=CC=C(C=C2OC=2C=C(C=CC12)O)O | [O:1]=[C:2]1[O:3][C:10](=[O:11])[CH2:9][CH2:4]1.[cH:7]1[c:13]([OH:14])[cH:12][c:17]([OH:18])[cH:19][cH:20]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]=[C:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[O:14][c:15]2[cH:16][c:17]([OH:18])[cH:19][cH:20][c:21]21 | O=C1CCC(=O)O1.Oc1cccc(O)c1 | O=C(O)CC=C1c2ccc(O)cc2Oc2cc(O)ccc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 4925f2a5eef4e9804a3612d2dae70eada4948017ed12fefbe63397580ba4f239 | 4c5e42ba40f03a268dd3324423389cf0e89fa2dfb6bd8dd2bc3e76b5039fdcf7 | [CH]=C1c2ccccc2Oc2ccccc21 | [O;D1;H0:1]=[C:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[O;H0;D2;+0:7]-1.[O;D1;H1:8]-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13](-[OH;D1;+0:14]):[cH;D2;+0:15]:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[CH2;D2;+0:3]-[C:16]=[C:17]1-[c:18]2:[cH;D2;+0:11]:[c:10]:[c;H0;D3;+0:9](-[O;D1;H1:8]):[... | 88.4 | [{"value": 88.0, "product": "C(=O)(O)CC=C1C2=CC=C(C=C2OC=2C=C(C=CC12)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "C(=O)(O)CC=C1C2=CC=C(C=C2OC=2C=C(C=CC12)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 2 | HOUR | Resorcinol (33.0 g, 0.300 mol) and succinic anhydride (30.0 g, 0.300 mol) were placed in a round bottomed flask and purged with nitrogen. Methanesulfonic acid (150 mL) was added and the solution was stirred at 65° C. for 2 hours under an atmosphere of nitrogen. The reaction mixture was added dropwise to rapidly stirred... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol.Aromatic alcohol | Carboxylic acid.Ether.Aromatic alcohol.Aromatic alcohol | C1CCOC1.c1ccccc1 | c1ccc2c(c1)Cc1ccccc1O2 | c1ccc2c(c1)Cc1ccccc1O2 | Other | null | 65 | 2 | O=C1CCC(=O)O1.Oc1cccc(O)c1>>O=C(O)CC=C1c2ccc(O)cc2Oc2cc(O)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-237c45c77bf1482fa8552c921abf2dea | O=Cc1ccc(O)cc1O>>Cc1ccc(O)cc1O | [H][H].P(O)(O)(O)=O.OC1=C(C=O)C=CC(=C1)O.[H][H]>>CC1=C(C=C(O)C=C1)O | O=[CH:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[OH:9]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[OH:9] | O=Cc1ccc(O)cc1O | Cc1ccc(O)cc1O | null | [Pd] | CC(C)O | Reduction | OtherReaction | 80164d08698e723aff741c2b428f9ebe7e14faf51ad55ff412ac682536758b9f | 9b627af1c37cea795d25b24c8b755865edc79a56af73aa7fa1348903b24aee3f | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98.1 | [{"value": 98.0, "product": "CC1=C(C=C(O)C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "CC1=C(C=C(O)C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4-Dihyroxybenzaldehyde (33.97 gm, 0.246 mol) (recrystallized from toluene) was dissolved in spectroscopic grade 2-propanol (3 L) in a round bottom flask fitted with a gas inlet and a bubbler outlet. 10% Palladium on carbon (1.35 gm) was added followed by phosphoric acid (3mL) and the mixture was sparaged with nitroge... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1 | Other | [Pd].CC(C)O | null | null | O=Cc1ccc(O)cc1O>[Pd].CC(C)O>Cc1ccc(O)cc1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-97f438e7ffbd4764b1ee7bf05860487d | Cc1ccc(O)cc1O.O=C1CCC(=O)O1>>Cc1cc2c(cc1O)Oc1cc(O)c(C)cc1C2=CCC(=O)O | CC1=C(C=C(O)C=C1)O.C1(CCC(=O)O1)=O>>C(=O)(O)CC=C1C2=CC(=C(C=C2OC=2C=C(C(=CC12)C)O)O)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:9])[cH:6][c:7]1[OH:8].[CH2:10]1[C:12](=[O:13])[O:23][C:21](=[O:22])[CH2:20]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[OH:8])[O:9][c:10]1[cH:11][c:12]([OH:13])[c:14]([CH3:15])[cH:16][c:17]1[C:18]2=[CH:19][CH2:20][C:21](=[O:22])[OH:23] | Cc1ccc(O)cc1O.O=C1CCC(=O)O1 | Cc1cc2c(cc1O)Oc1cc(O)c(C)cc1C2=CCC(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8e7ce8e5ab260605c6335916ab57b07e358f90acd2e31915711746a6f7c02794 | 2af0d7052e250fcc0027d675556884856e46081e4d1bd17dfc6a2818e78b4b0b | [CH]=C1c2ccccc2Oc2ccccc21 | [O;D1;H0:1]=[C:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[O;H0;D2;+0:7]-1.[OH;D1;+0:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[C;D1;H3:14]-[c:15]1:[c:16]:[c:17]2:[c;H0;D3;+0:4](:[c:18]:[c;H0;D3;+0:5]:1-[OH;D1;+0:6])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](:[c:12]:[c:13])-[C:19]-2=[C:20]... | 74.2 | [{"value": 74.0, "product": "C(=O)(O)CC=C1C2=CC(=C(C=C2OC=2C=C(C(=CC12)C)O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.2, "product": "C(=O)(O)CC=C1C2=CC(=C(C=C2OC=2C=C(C(=CC12)C)O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | 4-Methylresorcinol (25.8 g, 0.208 mol) and succinic anhydride (20.8 g, 0.208 g) were placed in a round bottom flask and the flask was purged with nitrogen. Methanesulfonic acid (150 mL) was added and the solution heated under nitrogen to 65° C. for 2 hours. The solution was added dropwise to 1 L of rapidly stirred, ice... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Carboxylic acid.Ether.Aromatic alcohol | c1ccccc1.C1CCOC1 | c1ccc2c(c1)Cc1ccccc1O2 | c1ccc2c(c1)Cc1ccccc1O2 | Other | null | 65 | null | Cc1ccc(O)cc1O.O=C1CCC(=O)O1>>Cc1cc2c(cc1O)Oc1cc(O)c(C)cc1C2=CCC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-69d326a15330467090d94484b9ed6312 | CN(C=O)c1ccccc1.Cc1c(O)cccc1O>>Cc1c(O)ccc(C=O)c1O | P(=O)(Cl)(Cl)Cl.CN(C1=CC=CC=C1)C=O.CC1=C(O)C=CC=C1O>>OC1=C(C=O)C=CC(=C1C)O | CN(c1ccccc1)[CH:8]=[O:9].[CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:10]1[OH:11]>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[OH:11] | CN(C=O)c1ccccc1.Cc1c(O)cccc1O | Cc1c(O)ccc(C=O)c1O | null | null | CCOCC | C-C Coupling | OtherReaction | 285803636db9e45ff0b980aa9c160ed6302cad8a21b5d872b908f4e4658d903e | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-[CH;D2;+0:1]=[O;D1;H0:2])-c1:c:c:c:c:c:1.[O;D1;H1:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](-[O;D1;H1:3]):[c:5] | 57 | [{"value": 57.0, "product": "OC1=C(C=O)C=CC(=C1C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "OC1=C(C=O)C=CC(=C1C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Phosphorus oxychloride (80 mL, 0.86 mol) was added to a stirred mixture of N-methylformanilide (102 mL, 0.82 mol) in ether (250 mL). The mixture was stirred for 1 hour at room temperature and then cooled in ice. 2-Methyl resorcinol (Aldrich, 100 g, 0.81 mol) was added and the mixture was allowed to warm to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CCOCC | null | 1 | CN(C=O)c1ccccc1.Cc1c(O)cccc1O>CCOCC>Cc1c(O)ccc(C=O)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-acac41327ddf4baf83b59f70db7ade15 | Cc1c(O)ccc(C=O)c1O>>Cc1ccc(O)c(C)c1O | OC1=C(C=O)C=CC(=C1C)O.P(O)(O)(O)=O>>CC1=C(O)C=CC(=C1O)C | O=[CH:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([CH3:8])[c:9]1[OH:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([CH3:8])[c:9]1[OH:10] | Cc1c(O)ccc(C=O)c1O | Cc1ccc(O)c(C)c1O | null | [Pd] | C(C)(C)O | Reduction | OtherReaction | 80164d08698e723aff741c2b428f9ebe7e14faf51ad55ff412ac682536758b9f | 9b627af1c37cea795d25b24c8b755865edc79a56af73aa7fa1348903b24aee3f | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4] | 72 | [{"value": 72.0, "product": "CC1=C(O)C=CC(=C1O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "CC1=C(O)C=CC(=C1O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,4-dihydroxy-3-methylbenzaldehyde (30.0 g, 197 mmol) with isopropanol (3 L) was ice-cooled in a 5 L 3-neck flask fitted with a magnetic stirrer. Phosphoric acid (4 mL) and d10% palladium on carbon were added and the solution was sparged with nitrogen, then hydrogen. When uptake was judged to be complete ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1 | Other | [Pd].C(C)(C)O | null | null | Cc1c(O)ccc(C=O)c1O>[Pd].C(C)(C)O>Cc1ccc(O)c(C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-88e1e4ec780f4191be8409df6b2f61b1 | II.Nc1ccn([C@H]2CC[C@@H](CO)O2)c(=O)n1>>Nc1nc(=O)n([C@H]2CC[C@@H](CO)O2)cc1I | [C@@H]1(CC[C@@H](CO)O1)N1C(=O)N=C(N)C=C1.II>>IC=1C(=NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)N | I[I:16].[NH2:1][c:2]1[n:3][c:4](=[O:5])[n:6]([C@H:7]2[CH2:8][CH2:9][C@@H:10]([CH2:11][OH:12])[O:13]2)[cH:14][cH:15]1>>[NH2:1][c:2]1[n:3][c:4](=[O:5])[n:6]([C@H:7]2[CH2:8][CH2:9][C@@H:10]([CH2:11][OH:12])[O:13]2)[cH:14][c:15]1[I:16] | II.Nc1ccn([C@H]2CC[C@@H](CO)O2)c(=O)n1 | Nc1nc(=O)n([C@H]2CC[C@@H](CO)O2)cc1I | null | null | ClCCl.CO | Functional Group Interconversion | OtherReaction | b0bb6940bdaa4f483f95617a9ee5e6563c160ea710db3fde10ee056459a3fce1 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1ncccn1[C@H]1CCCO1 | I-[I;H0;D1;+0:1].[#8:2]-[C:3]-[#7;a:4]1:[c:5]:[cH;D2;+0:6]:[c:7](-[N;D1;H2:8]):[#7;a:9]:[c:10]:1>>[#8:2]-[C:3]-[#7;a:4]1:[c:5]:[c;H0;D3;+0:6](-[I;H0;D1;+0:1]):[c:7](-[N;D1;H2:8]):[#7;a:9]:[c:10]:1 | 83 | [{"value": 83.0, "product": "IC=1C(=NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "IC=1C(=NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 2', 3'-dideoxycytidine (2.11 g, 10 mmol, Raylo) and mercuric acetate (3.35 g, 10.5 mmol, Fisher) in 50 mL of methanol was refluxed for 19 hours. The resulting white suspension was diluted with methanol (50 mL) and dichloromethane (100 mL). Iodine (3.05 g, 12 mmol) was added and the suspension was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CCOC1 | HI | ClCCl.CO | null | 4 | II.Nc1ccn([C@H]2CC[C@@H](CO)O2)c(=O)n1>ClCCl.CO>Nc1nc(=O)n([C@H]2CC[C@@H](CO)O2)cc1I |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dae2fd2549ce4bb2a6b66fb56721b9fb | CCCCN(CCCC)CCCC.O=P([O-])([O-])OP(=O)([O-])[O-].c1ccncc1>>CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC.O=P([O-])([O-])OP(=O)([O-])O | N1=CC=CC=C1.O.O.O.O.O.O.O.O.O.O.[O-]P([O-])(=O)OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+].C(CCC)N(CCCC)CCCC>>[O-]P([O-])(=O)OP(=O)([O-])O.C(CCC)[NH+](CCCC)CCCC.C(CCC)[NH+](CCCC)CCCC.C(CCC)[NH+](CCCC)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][N:18]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:36][CH2:37][CH2:38][CH3:39].[O:40]=[P:41]([O-:42])([O-:43])[O:44][P:45](=[O:46])([O-:47])[O-:48].[n:5]1[cH:6][cH:7][cH:8][cH:20][cH:10]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH+:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13].[CH3:14][CH... | CCCCN(CCCC)CCCC.O=P([O-])([O-])OP(=O)([O-])[O-].c1ccncc1 | CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC.O=P([O-])([O-])OP(=O)([O-])O | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 7b212c0c068f7c0a0dcdcb2565ee613e3020cb41766d4f4424178d3ecf789f7e | 7c33147a6170e63e1fbe1110c4ce069481be57a96b70c4a5a6d7e8253f321bd2 | null | [#8:1]-[#15:2](-[O-;H0;D1:3])(-[O;-;D1;H0:4])=[O;D1;H0:5].[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:9]-[C:10]-[C:11])-[CH2;D2;+0:12]-[C:13]-[C:14].[cH;D2;+0:15]1:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:[n;H0;D2;+0:20]:1>>[#8:1]-[#15:2](-[O;-;D1;H0:4])(=[O;D1;H0:5])-[OH;D1;+0:3].[C:21]-[#7;+:22](-[C:23])-[C... | null | [] | null | null | null | null | Tetrasodium pyrophosphate decahydrate (4.46 g, 10 mmol) was dissolved in the minimum amount of water (about 50 mL) and passed through a column of AG50W X8 (100-200 mesh, 4×10 cm bed) poured in water. The column was eluted with water and the eluent was collected in an ice-cooled flask until pH of the eluent approached n... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccncc1 | null | null | null | CN(C=O)C.O | null | null | CCCCN(CCCC)CCCC.O=P([O-])([O-])OP(=O)([O-])[O-].c1ccncc1>CN(C=O)C.O>CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC.O=P([O-])([O-])OP(=O)([O-])O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2754db0450694fd5addb217d80c7651c | ClI.O=c1ccn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]1>>O=c1[nH]c(=O)n([C@H]2CC[C@@H](CO)O2)cc1I | [C@@H]1(CC[C@@H](CO)O1)N1C(=O)NC(=O)C=C1.ICl>>IC=1C(NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)=O | Cl[I:16].[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([C@H:7]2[CH2:8][CH2:9][C@@H:10]([CH2:11][OH:12])[O:13]2)[cH:14][cH:15]1>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([C@H:7]2[CH2:8][CH2:9][C@@H:10]([CH2:11][OH:12])[O:13]2)[cH:14][c:15]1[I:16] | ClI.O=c1ccn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]1 | O=c1[nH]c(=O)n([C@H]2CC[C@@H](CO)O2)cc1I | null | null | CO | Functional Group Interconversion | OtherReaction | ab990d4cf4e29f4bfc1eed19f85a157586116cba28cf7e047e67e704b97886a0 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | Cl-[I;H0;D1;+0:1].[#8:2]-[C:3]-[#7;a:4]1:[c:5]:[cH;D2;+0:6]:[c:7](=[O;D1;H0:8]):[#7;a:9]:[c:10]:1>>[#8:2]-[C:3]-[#7;a:4]1:[c:5]:[c;H0;D3;+0:6](-[I;H0;D1;+0:1]):[c:7](=[O;D1;H0:8]):[#7;a:9]:[c:10]:1 | 66 | [{"value": 66.0, "product": "IC=1C(NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "IC=1C(NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 165 | MINUTE | Dideoxyuridine (2.122 g, 10.0 mmol) was dissolved in 30 mL of warm methanol and, after cooling to 25°, iodine monochloride (4.06 g, 25 mmol, 2.5 eq, Fisher) in methanol (20 mL) was added over 5 minutes. The dark purple reaction mixture was heated in a 50° bath under nitrogen for 20 minutes and then immediately cooled i... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncn1 | c1cncnc1 | c1cncnc1.C1CCOC1 | HCl | CO | null | 2.75 | ClI.O=c1ccn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]1>CO>O=c1[nH]c(=O)n([C@H]2CC[C@@H](CO)O2)cc1I |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f862215dba7846cf8cae5bec600dc198 | C#CCNC(=O)C(F)(F)F.O=c1ccn([C@]2(I)O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F | I[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1.C(C#C)NC(C(F)(F)F)=O.CO>>FC(C(=O)NCC#CC=1C(NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)=O)(F)F | [O:1]=[C:2]([NH:3][CH2:4][C:5]#[CH:6])[C:22]([F:23])([F:24])[F:25].O[C@H:11]1[C@:10](I)([n:9]2[cH:8][cH:7][c:20](=[O:21])[nH:19][c:17]2=[O:18])[O:16][C@H:13]([CH2:14][OH:15])[C@H:12]1O>>[O:1]=[C:2]([NH:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][n:9]([C@H:10]2[CH2:11][CH2:12][C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19... | C#CCNC(=O)C(F)(F)F.O=c1ccn([C@]2(I)O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 | O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F | null | null | ClCCl | C-C Coupling | OtherReaction | 79020e65c8a73c14d651f6b591a1daf884e17a3b0d82391b8a8ea303aeeec2d7 | feec4c80e84523492497dfe04bfed80862cb3ade02d554790cab7099c3d3dac5 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | I-[C@@;H0;D4;+0:1]1(-[#7;a:2]2:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[cH;D2;+0:7]:[c:8]:2)-[#8:9]-[C:10](-[C:11])-[C@@H;D3;+0:12](-O)-[C@H;D3;+0:13]-1-O.[C:14]-[C:15]#[CH;D1;+0:16]>>[C:11]-[C:10]1-[#8:9]-[C@@H;D3;+0:1](-[#7;a:2]2:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[c;H0;D3;+0:7](-[C;H0;D2;+0:16]#[C:15]-[C:14]):[c:8]:2)-[C... | null | [] | null | null | null | null | Iodouridine 21 was coupled for 3 hours to N-propargyltrifluoroacetamide following the general method given in Example 5C. Chromatography with a 0-5% methanol in dichloromethane gradient afforded material which was homogeneous by TLC, but which was difficult to dry. After co-evaporating the chromatographed product sever... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ether.Secondary alcohol.Secondary alcohol.Alkyne | Ether.Alkyne | C1CCOC1.c1ccncn1 | c1cncnc1.C1CCOC1 | c1cncnc1.C1CCOC1 | HI | ClCCl | null | null | C#CCNC(=O)C(F)(F)F.O=c1ccn([C@]2(I)O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1>ClCCl>O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f62f81003c6c41a6ac6db8897b3efe07 | O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F.O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-]>>NCC#Cc1cn([C@H]2CC[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O | FC(C(=O)NCC#CC=1C(NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)=O)(F)F.[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-]>>P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1CC[C@@H](O1)N1C(=O)NC(=O)C(=C1)C#CCN | O=C(C(F)(F)F)[NH:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][n:7]([C@H:8]2[CH2:9][CH2:10][C@@H:11]([CH2:12][OH:13])[O:26]2)[c:27](=[O:28])[nH:29][c:30]1=[O:31].[O-][P:14](=[O:15])([O-:16])[O:17][P:18](=[O:19])([O-:20])[O:21][P:22](=[O:23])([O-:24])[O-:25]>>[NH2:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][n:7]([C@H:8]2[CH2:9][CH2:10][C@@H:11... | O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F.O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-] | NCC#Cc1cn([C@H]2CC[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O | null | null | null | Miscellaneous | OtherReaction | 202bfe9d4cc39183f8a334ff356e45e02f54d921ebf09363277273dabb646529 | 46156dbef801c93696b95c5685005862403542a82af6e01a304bedb700f59b74 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]#[C:4]-[c:5](:[c:6]:[#7;a:7]):[c:8]:[#7;a:9].[#8:10]-[C:11]-[C:12]-[OH;D1;+0:13].[O-;H0;D1:14]-[P;H0;D4;+0:15](-[O-])(=[O;D1;H0:16])-[#8:17]-[#15:18](-[O-;H0;D1:19])(=[O;D1;H0:20])-[#8:21]-[#15:22](-[O-;H0;D1:23])(-[O-;H0;D1:24])=[O;D1;H0:25]>>[#7;a:7]:[c:6]:[c:5](-[C:4]#[C:3]-... | null | [] | null | null | 210 | MINUTE | Alkynylamino nucleoside 22 (0.30 mmol) was converted to the corresponding triphosphate and its trifluoroacetyl group was removed following the general procedure given in Example 5E. After addition of the second aliquot of phosphorus oxychloride, phosphorylation was allowed to proceed for 210 minutes. Assuming an absorp... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide.Primary alcohol | Primary amine.Phosphate ester | null | null | c1cncnc1.C1CCOC1 | Other | null | null | 3.5 | O=C(NCC#Cc1cn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]c1=O)C(F)(F)F.O=P([O-])([O-])OP(=O)([O-])OP(=O)([O-])[O-]>>NCC#Cc1cn([C@H]2CC[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4087f7af24ab478188b0f20324748df5 | CN.Cc1ccc(S(=O)(=O)OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)cc1>>CNC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O | [K+].[Br-].C1(=CC=C(C=C1)S(=O)(=O)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O)C.CN.CN>>CNC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O | [CH3:1][NH2:2].Cc1ccc(S(=O)(=O)O[CH2:3][C@H:4]2[O:5][C@@H:6]([n:7]3[cH:8][c:9]([CH3:10])[c:11](=[O:12])[nH:13][c:14]3=[O:15])[CH2:16][C@@H:17]2[OH:18])cc1>>[CH3:1][NH:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][c:9]([CH3:10])[c:11](=[O:12])[nH:13][c:14]2=[O:15])[CH2:16][C@@H:17]1[OH:18] | CN.Cc1ccc(S(=O)(=O)OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)cc1 | CNC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 638d8ac0818bc5201610866a65ae9dacec8e97cdcf8f64754391fee0b8c67d26 | 5fc01bd280a9fcb20b84d795bd8ba6fa3b8702870fcffd0b390748ae9cc9cc09 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5]):c:c:1.[C;D1;H3:6]-[NH2;D1;+0:7]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[NH;D2;+0:7]-[C;D1;H3:6])-[#8:4]-[C:5] | null | [] | null | null | 3 | DAY | 5'-O-(p-toluenesulfonyl)thymidine (19.8 g, 50 mmol) was placed in a pressure vessel into which monomethylamine (250 g) was condensed. The vessel was sealed and allowed to stand at room temperature for 3 days. The vessel was cooled, opened, and the monomethylamine allowed to evaporate. The remaining contents of the vess... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary amine | Secondary amine | c1ccccc1 | null | C1CCOC1.c1cncnc1 | TsOH.HO- | O | null | 72 | CN.Cc1ccc(S(=O)(=O)OC[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)C[C@@H]2O)cc1>O>CNC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fef06120f7244b028a882a59eab365e0 | Cn1c(=O)c2[nH]c(CCCN)nc2n(C)c1=O>>Cn1c(=O)c2[nH]cnc2n(C)c1=O | NCCCC1=NC=2N(C(N(C)C(C2N1)=O)=O)C>>N1(C)C(=O)N(C)C=2N=CNC2C1=O | NCCC[c:7]1[nH:6][c:5]2[c:3](=[O:4])[n:2]([CH3:1])[c:12](=[O:13])[n:10]([CH3:11])[c:9]2[n:8]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[nH:6][cH:7][n:8][c:9]2[n:10]([CH3:11])[c:12]1=[O:13] | Cn1c(=O)c2[nH]c(CCCN)nc2n(C)c1=O | Cn1c(=O)c2[nH]cnc2n(C)c1=O | null | null | C([O-])([O-])=O | Deprotection | OtherReaction | 999929fb35c459640fe6677f54719c0eee39b2af4c6b530442e3859eabba5dc8 | 5a39875410f78de0778907c5ec963354b592c2b209b9049b152e5c90fc9aa424 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | N-C-C-C-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[#7;a:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]:2:[#7;a:10]:1>>[C;D1;H3:8]-[#7;a:7]1:[c:6]:[#7;a:5]:[c:4]:[c:3]2:[#7;a:2]:[cH;D2;+0:1]:[#7;a:10]:[c:9]:1:2 | null | [] | null | null | null | null | A solution of 5 mM 8-(3-aminopropyl)-theophylline (R.C. Boguslaski et al., 1980) in 0.1 M carbonate buffer, pH 8.0, was incubated with an N-hydroxysuccinimide ester activated dextran surface (according to Example I.3.2) overnight at 25° C., whereupon the surface was washed with water.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | C([O-])([O-])=O | null | null | Cn1c(=O)c2[nH]c(CCCN)nc2n(C)c1=O>C([O-])([O-])=O>Cn1c(=O)c2[nH]cnc2n(C)c1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3e5a74dd499d489bad82923a415203e2 | C=CC(Cl)c1ccccc1.C=CC(Cl)c1ccccc1.CC(=O)/C=C(/C)[O-]>>C=Cc1cccc(CC(C(C)=O)C(C)=O)c1 | C(=C)C(C1=CC=CC=C1)Cl.C/C(=C/C(=O)C)/[O-].[Na+].[I-].[Na+].C(=C)C(C1=CC=CC=C1)Cl.CC(=O)C.CC(=O)C>>C(=C)C=1C=C(CC(C(C)=O)C(C)=O)C=CC1 | C=C[CH:8](Cl)[c:7]1cccc[cH:16]1.C=[CH:1][CH:2](Cl)[c:3]1cc[cH:6][cH:5][cH:4]1.[CH:9](\[C:10]([CH3:11])=[O:12])=[C:13](/[CH3:14])[O-:15]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH:9]([C:10]([CH3:11])=[O:12])[C:13]([CH3:14])=[O:15])[cH:16]1 | C=CC(Cl)c1ccccc1.C=CC(Cl)c1ccccc1.CC(=O)/C=C(/C)[O-] | C=Cc1cccc(CC(C(C)=O)C(C)=O)c1 | null | null | null | Acylation | OtherReaction | 31127f4c33519efa8cacb9513f536f97f4a15745b0e64b22f5c4a87d89e6e123 | 75acb20a8c8c10d0c404e241869ac0c4b23d8748eee1f1cc1d2051ea4e5952da | c1ccccc1 | C=C-[CH;D3;+0:1](-Cl)-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:c:c:c:c:1.C=[CH;D2;+0:4]-[CH;D3;+0:5](-Cl)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:c:c:1.[C;D1;H3:10]-[C:11](=[O;D1;H0:12])/[CH;D2;+0:13]=[C;H0;D3;+0:14](/[C;D1;H3:15])-[O-;H0;D1:16]>>[C;D1;H3:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;... | null | [] | null | null | null | null | To 308 g of sodium acetylacetonate and 30 g of sodium iodide in 100 mL acetone (dried over 3A molecular sieves) was added dropwise 282 ml vinylbenzyl chloride (70% Meta, 30% Para), in 600 ml acetone. An ice bath was used to keep the pot temperature below 50° during the addition. The solution was maintained at 45°-50° C... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ketone.Vinyl.Vinyl | Ketone.Ketone.Vinyl | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | null | C=CC(Cl)c1ccccc1.C=CC(Cl)c1ccccc1.CC(=O)/C=C(/C)[O-]>>C=Cc1cccc(CC(C(C)=O)C(C)=O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-404ac2a782b04285b1b2dc05ed2a47c8 | C=C(C)C(=O)OC.c1ccc2c(c1)Nc1ccccc1S2>>C=C(C)C(=O)OCCCC | C(C(=C)C)(=O)OC.C1=CC=CC=2SC3=CC=CC=C3NC12>>C(C(=C)C)(=O)OCCCC | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH3:7].c1ccc2c(c1)Nc1c[cH:10][cH:8][cH:9]c1S2>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][CH2:9][CH3:10] | C=C(C)C(=O)OC.c1ccc2c(c1)Nc1ccccc1S2 | C=C(C)C(=O)OCCCC | null | null | C(CCC)O | C-C Coupling | OtherReaction | b29de4aae1a731855e0dbf3b55e482ef9401c13e3f76bf07e7b3578e1662373e | eaa3d0330089f8b63f71d1899090b3847cce744f5ae028d6d671f21ac4689a5e | null | N1-c2:c:[cH;D2;+0:1]:[cH;D2;+0:2]:[cH;D2;+0:3]:c:2-S-c2:c:c:c:c:c:2-1.[C;D1;H2:4]=[C:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[CH3;D1;+0:9]>>[C;D1;H2:4]=[C:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[CH2;D2;+0:9]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH3;D1;+0:1] | null | [] | null | null | 6 | HOUR | Two hundred six grams of a reaction mix containing a 5:1 mole ratio of methyl methacrylate, 1-butanol, and 100 ppm phenothiazine as inhibitor were added to a 500 ml flask equipped with an agitatior, thermocouple, and a 10-tray Oldershaw fractional distillation column. Thirty grams of the heterogeneous zirconium vinylbe... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Monosulfide | Ester | c1ccc2c(c1)Nc1ccccc1S2 | null | null | Other | C(CCC)O | null | 6 | C=C(C)C(=O)OC.c1ccc2c(c1)Nc1ccccc1S2>C(CCC)O>C=C(C)C(=O)OCCCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bff539d21f0449efa90cb66fd5b38883 | C=C(C)C(=O)OC.CCCCCCCCCCCCO>>C=C(C)C(=O)OCCCCCCCCCCCC | C(C(=C)C)(=O)OC.C(CCCCCCCCCCC)O.C1=CC=CC=2SC3=CC=CC=C3NC12>>C(C(=C)C)(=O)OCCCCCCCCCCCC | CO[C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18] | C=C(C)C(=O)OC.CCCCCCCCCCCCO | C=C(C)C(=O)OCCCCCCCCCCCC | null | null | null | Protection | Transesterification | 1adccd25c595429871da3756142c075aac7032d22473ca1588e41d51e1a19040 | a6c84db4df003bced50681f216baba6e759c1d4451f21f814c7bb7ee782a7375 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5] | null | [] | null | null | 6 | HOUR | Two hundred six grams of a reaction mix containing a 5:1 mole ratio of methyl methacrylate, 1-dodecanol, and 100 ppm phenothiazine as inhibitor were added to a 500 ml flask equipped with an agitatior, thermocouple, and a 10-tray Oldershaw fractional distillation column. Thirty grams of the heterogeneous zirconium vinyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | null | HO- | null | null | 6 | C=C(C)C(=O)OC.CCCCCCCCCCCCO>>C=C(C)C(=O)OCCCCCCCCCCCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-78085214e0d5496ab614bdad6a715709 | C=CCc1noc(CCl)n1.Oc1ccc(F)cc1Cl>>C=CCc1noc(COc2ccc(F)cc2Cl)n1 | ClC1=C(C=CC(=C1)F)O.C(C=C)C1=NOC(=N1)CCl.C([O-])([O-])=O.[K+].[K+]>>C(C=C)C1=NOC(=N1)COC1=C(C=C(C=C1)F)Cl | Cl[CH2:8][c:7]1[o:6][n:5][c:4]([CH2:3][CH:2]=[CH2:1])[n:18]1.[OH:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]1[Cl:17]>>[CH2:1]=[CH:2][CH2:3][c:4]1[n:5][o:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[Cl:17])[n:18]1 | C=CCc1noc(CCl)n1.Oc1ccc(F)cc1Cl | C=CCc1noc(COc2ccc(F)cc2Cl)n1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ncno2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[#8;a:6]:1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[#8;a:6]:1):[c:10] | 80.8 | [{"value": 80.8, "product": "C(C=C)C1=NOC(=N1)COC1=C(C=C(C=C1)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "C(C=C)C1=NOC(=N1)COC1=C(C=C(C=C1)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.71 g of 2-chloro-4-fluorophenol, 0.77 g of 3-allyl-5-chloromethyl-1,2,4-oxadiazole and 0.83 of potassium carbonate were added to 20 ml of acetone. After completion of the reaction, the resulting precipitates were filtered out from the mixture and then acetone was removed by distillation, and the residue was purified ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ncon1.c1ccccc1 | HCl | CC(=O)C | null | null | C=CCc1noc(CCl)n1.Oc1ccc(F)cc1Cl>CC(=O)C>C=CCc1noc(COc2ccc(F)cc2Cl)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e5bfa70b33c24bb5b62e1dfb336704c5 | CCOC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1>>CCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1 | C(C)OC(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl.C(C)[Mg]Br.Cl>>C(C)C(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl | CCO[C:3](=[O:4])[c:5]1[n:6][o:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[n:19]1>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[n:6][o:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[n:19]1 | CCOC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1 | CCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 600d91131af1bb1ee8c20c567e56234839eb0602aa06d3adc0666216769f9a6a | ebe855e3c62a5d82c9c1d005e3b3e8a9e3b63aca37bc8a601a136cf86007489d | c1ccc(OCc2ncno2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#8;a:6]:[#7;a:7]:1>>[C;D1;H3:8]-[C:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#8;a:6]:[#7;a:7]:1 | 83 | [{"value": 83.0, "product": "C(C)C(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | 0.95 g of 3-ethoxycarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole was added to 30 ml of tetrahydrofuran. The mixture was cooled to -78° C., and then 3 ml of ethylmagnesium bromide (2M solution) was added dropwise. After the mixture was stirred at -78° C. for 1 hour, it was poured into cold aqueous 5% HCl solu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ncon1.c1ccccc1 | Other | O1CCCC1 | -78 | 1 | CCOC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1>O1CCCC1>CCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ee847813e8e14c88ba9cb5b8597ec847 | CCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1.NO>>CCC(=NO)c1noc(COc2ccc(Cl)cc2Cl)n1 | C(C)C(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl.Cl.ON>>ON=C(CC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl | O=[C:3]([CH2:2][CH3:1])[c:6]1[n:7][o:8][c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[Cl:19])[n:20]1.[NH2:4][OH:5]>>[CH3:1][CH2:2][C:3](=[N:4][OH:5])[c:6]1[n:7][o:8][c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[Cl:19])[n:20]1 | CCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1.NO | CCC(=NO)c1noc(COc2ccc(Cl)cc2Cl)n1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc(OCc2ncno2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C;D1;H3:3])-[c:4]1:[#7;a:5]:[c:6]:[#8;a:7]:[#7;a:8]:1.[NH2;D1;+0:9]-[O;D1;H1:10]>>[C;D1;H3:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:9]-[O;D1;H1:10])-[c:4]1:[#7;a:5]:[c:6]:[#8;a:7]:[#7;a:8]:1 | 85 | [{"value": 85.0, "product": "ON=C(CC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.7, "product": "ON=C(CC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.9 g of 3-ethylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole and 0.21 g of hydroxyamine hydrochloride were added to 10 ml of methanol. The mixture was heated to reflux for 4 hours. After evaporation of methanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After eva... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ncon1.c1ccccc1 | HO- | CO | null | null | CCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1.NO>CO>CCC(=NO)c1noc(COc2ccc(Cl)cc2Cl)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-71d372ee817748b9b806f8449f71356b | CCCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1>>CCCC(O)c1noc(COc2ccc(Cl)cc2Cl)n1 | C(CC)C(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl.CC([O-])C.[Al+3].CC([O-])C.CC([O-])C>>OC(CCC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl | [CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[n:7][o:8][c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[Cl:19])[n:20]1>>[CH3:1][CH2:2][CH2:3][CH:4]([OH:5])[c:6]1[n:7][o:8][c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[Cl:19])[n:20]1 | CCCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1 | CCCC(O)c1noc(COc2ccc(Cl)cc2Cl)n1 | null | null | C(C)(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(OCc2ncno2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7]:[#8;a:8]:[#7;a:9]:1>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5]1:[#7;a:6]:[c:7]:[#8;a:8]:[#7;a:9]:1 | 54 | [{"value": 54.0, "product": "OC(CCC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.5, "product": "OC(CCC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.316 g of 3-propylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole and 0.20 g of aluminum isopropoxide were added to 10 ml of isopropanol. The mixture was heated to reflux for 48 hours. After evaporation of isopropanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ncon1.c1ccccc1 | null | C(C)(C)O | null | null | CCCC(=O)c1noc(COc2ccc(Cl)cc2Cl)n1>C(C)(C)O>CCCC(O)c1noc(COc2ccc(Cl)cc2Cl)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f7f78b9b17294d74a78dab97f5765fd7 | CO.Clc1ccc(OCc2nc(C(Cl)(Cl)Cl)no2)c(Cl)c1.N>>N=COCc1noc(COc2ccc(Cl)cc2Cl)n1 | ClC(C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl)(Cl)Cl.CO.N>>N=COCC1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl | [CH3:2][OH:3].Cl[C:4](Cl)(Cl)[c:5]1[n:6][o:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[n:19]1.[NH3:1]>>[NH:1]=[CH:2][O:3][CH2:4][c:5]1[n:6][o:7][c:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[n:19]1 | CO.Clc1ccc(OCc2nc(C(Cl)(Cl)Cl)no2)c(Cl)c1.N | N=COCc1noc(COc2ccc(Cl)cc2Cl)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3165328e1df447a7b4dd544a286cfa722eec7f2e0dcc6edb1d8edee130bac9d1 | d4b362c6db8558ccca20b721b79cf14321d12ee6b3f0a59f0c6ad4b2ff912dd6 | c1ccc(OCc2ncno2)cc1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[#7;a:6]:1.[CH3;D1;+0:7]-[OH;D1;+0:8].[NH3;D0;+0:9]>>[NH;D1;+0:9]=[CH;D2;+0:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[#7;a:6]:1 | 50.9 | [{"value": 50.9, "product": "N=COCC1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 2.17 g of 3-(trichloromethyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole was added to 50 ml of methanol. An excess of ammonia gas was added with formation of bubble at 0° C. and then the mixture was stirred at room temperature for 4 hours. After evaporation of methanol, water was added to the residue. The aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Methanol | Ether | null | null | c1ncon1.c1ccccc1 | HCl | null | null | 4 | CO.Clc1ccc(OCc2nc(C(Cl)(Cl)Cl)no2)c(Cl)c1.N>>N=COCc1noc(COc2ccc(Cl)cc2Cl)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0486b163d93d4c4098549fecca2a4eab | CC1=C(C)C(=O)OC1=O.Nc1ccc(Cl)c(S(N)(=O)=O)c1>>CC1=C(C)C(=O)N(c2ccc(Cl)c(S(N)(=O)=O)c2)C1=O | NC=1C=CC(=C(C1)S(=O)(=O)N)Cl.C/C=1/C(=O)OC(\C1\C)=O>>ClC1=C(C=C(C=C1)N1C(C(=C(C1=O)C)C)=O)S(=O)(=O)N | O1[C:5](=[O:6])[C:3]([CH3:4])=[C:2]([CH3:1])[C:19]1=[O:20].[NH2:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[c:13]([S:14]([NH2:15])(=[O:16])=[O:17])[cH:18]1>>[CH3:1][C:2]1=[C:3]([CH3:4])[C:5](=[O:6])[N:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[c:13]([S:14]([NH2:15])(=[O:16])=[O:17])[cH:18]2)[C:19]1=[O:20] | CC1=C(C)C(=O)OC1=O.Nc1ccc(Cl)c(S(N)(=O)=O)c1 | CC1=C(C)C(=O)N(c2ccc(Cl)c(S(N)(=O)=O)c2)C1=O | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=CC(=O)N1c1ccccc1 | [C;D1;H3:1]-[C:2]1=[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:1]-[C:2]1=[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 93 | [{"value": 93.0, "product": "ClC1=C(C=C(C=C1)N1C(C(=C(C1=O)C)C)=O)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | In 3 ml of pyridine, 1 mmol of 5-amino-2-chlorobenzenesulfonamide and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 90-100° C. for 9 hours. Pyridine was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water and 0.1 ml of 35% hydrochloric acid to the solid residue. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | 0.333333 | CC1=C(C)C(=O)OC1=O.Nc1ccc(Cl)c(S(N)(=O)=O)c1>N1=CC=CC=C1>CC1=C(C)C(=O)N(c2ccc(Cl)c(S(N)(=O)=O)c2)C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b9ac6e1cabe64925a2abe6ef104073ff | CC1=C(C)C(=O)OC1=O.COC(=O)c1ccc(N)cc1S(N)(=O)=O>>COC(=O)c1ccc(N2C(=O)C(C)=C(C)C2=O)cc1S(N)(=O)=O | NC1=CC(=C(C(=O)OC)C=C1)S(=O)(=O)N.C/C=1/C(=O)OC(\C1\C)=O>>NS(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)N1C(C(=C(C1=O)C)C)=O | O1[C:10](=[O:11])[C:12]([CH3:13])=[C:14]([CH3:15])[C:16]1=[O:17].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:18][c:19]1[S:20]([NH2:21])(=[O:22])=[O:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[C:10](=[O:11])[C:12]([CH3:13])=[C:14]([CH3:15])[C:16]2=[O:17])[cH:18][c:19]1[S:20]([NH2:21])(=... | CC1=C(C)C(=O)OC1=O.COC(=O)c1ccc(N)cc1S(N)(=O)=O | COC(=O)c1ccc(N2C(=O)C(C)=C(C)C2=O)cc1S(N)(=O)=O | null | null | C(C)(=O)O | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=CC(=O)N1c1ccccc1 | [C;D1;H3:1]-[C:2]1=[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:1]-[C:2]1=[C:3](-[C;D1;H3:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 43 | [{"value": 43.0, "product": "NS(=O)(=O)C1=C(C(=O)OC)C=CC(=C1)N1C(C(=C(C1=O)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | In 3 ml of acetic acid, 1 mmol of methyl 4-amino-2-(aminosulfonyl)benzoate and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 80° C. for 40 hours. Acetic acid was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water to the oily residue. After the mixture thus formed wa... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | c1ccccc1.C1=CC[NH]C1 | HO- | C(C)(=O)O | null | 2 | CC1=C(C)C(=O)OC1=O.COC(=O)c1ccc(N)cc1S(N)(=O)=O>C(C)(=O)O>COC(=O)c1ccc(N2C(=O)C(C)=C(C)C2=O)cc1S(N)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a7a4e504e0e84b019b4a1e1fa710be55 | COC(=O)c1c(Sc2nc(OC)cc(OC)n2)cccc1C(C)=O.CON>>CON=C(C)c1cccc(Sc2nc(OC)cc(OC)n2)c1C(=O)OC | C([O-])([O-])=O.[K+].[K+].COC1=NC(=NC(=C1)OC)SC1=C(C(=O)OC)C(=CC=C1)C(C)=O.Cl.CON.O>>COC1=NC(=NC(=C1)OC)SC1=C(C(=O)OC)C(=CC=C1)C(C)=NOC | O=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([S:11][c:12]2[n:13][c:14]([O:15][CH3:16])[cH:17][c:18]([O:19][CH3:20])[n:21]2)[c:22]1[C:23](=[O:24])[O:25][CH3:26].[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][N:3]=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([S:11][c:12]2[n:13][c:14]([O:15][CH3:16])[cH:17][c:18]([O:19][CH3:20])[n:2... | COC(=O)c1c(Sc2nc(OC)cc(OC)n2)cccc1C(C)=O.CON | CON=C(C)c1cccc(Sc2nc(OC)cc(OC)n2)c1C(=O)OC | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | c1ccc(Sc2ncccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H3:9]-[#8:10]-[NH2;D1;+0:11]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:3](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;H0;D2;+0:11]-[#8:10]-[C;D1;H3:9]):[c:4] | 60 | [{"value": 59.0, "product": "COC1=NC(=NC(=C1)OC)SC1=C(C(=O)OC)C(=CC=C1)C(C)=NOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "COC1=NC(=NC(=C1)OC)SC1=C(C(=O)OC)C(=CC=C1)C(C)=NOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoate and 0.5 g of methoxyamine hydrochloride were dissolved in 6 ml of methanol, and the resultant solution was refluxed for 15 minutes. After cooling the mixed liquor to room temperature, 0.8 g of potassium carbonate was added to this liquor and the res... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1cncnc1 | HO- | CO | null | null | COC(=O)c1c(Sc2nc(OC)cc(OC)n2)cccc1C(C)=O.CON>CO>CON=C(C)c1cccc(Sc2nc(OC)cc(OC)n2)c1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bef430985b434ffd803e950af8b3d2e0 | COC(=O)c1c(O)cccc1C=O.COc1cc(OC)nc(S(C)(=O)=O)n1>>COC(=O)c1c(C=O)cccc1Oc1nc(OC)cc(OC)n1 | C(=O)C1=C(C(=O)OC)C(=CC=C1)O.COC1=NC(=NC(=C1)OC)S(=O)(=O)C.C([O-])([O-])=O.[K+].[K+]>>COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH:7]=[O:8])[cH:9][cH:10][cH:11][c:12]1[OH:13].CS(=O)(=O)[c:14]1[n:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[n:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH:7]=[O:8])[cH:9][cH:10][cH:11][c:12]1[O:13][c:14]1[n:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[n:23... | COC(=O)c1c(O)cccc1C=O.COc1cc(OC)nc(S(C)(=O)=O)n1 | COC(=O)c1c(C=O)cccc1Oc1nc(OC)cc(OC)n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 1c345af4a3df0f977c6c030350153f590996fc7a2b6ceaf9fe6cff27648ed228 | 5df75ac15caf6173d8206dd70d45a57321a6ccb2169690bfa04f02c58252d4f1 | c1ccc(Oc2ncccn2)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[O;H0;D2;+0:11]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:12] | 56.1 | [{"value": 52.0, "product": "COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.1, "product": "COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 13.8 g of potassium carbonate and 50 ml of DMF were placed in a 200 ml eggplant type flask, and 11.1 g of methyl 2-formyl-6-hydroxybenzoate and 14.6 g of 4,6-dimethoxy-2-methanesulfonylpyrimidine were added thereto with stirring. The mixture was stirred at 80° C. for 1 hour, and the resultant liquor was poured into an ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfone | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | CN(C)C=O | null | null | COC(=O)c1c(O)cccc1C=O.COc1cc(OC)nc(S(C)(=O)=O)n1>CN(C)C=O>COC(=O)c1c(C=O)cccc1Oc1nc(OC)cc(OC)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e77e497ab65949148fe18d9b14c87ef9 | COC(=O)c1c(C=O)cccc1Oc1nc(OC)cc(OC)n1.NO>>COC(=O)c1c(C=NO)cccc1Oc1nc(OC)cc(OC)n1 | COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=O.Cl.ON.C(C)(=O)[O-].[K+]>>COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NO | O=[CH:7][c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:13]([O:14][c:15]2[n:16][c:17]([O:18][CH3:19])[cH:20][c:21]([O:22][CH3:23])[n:24]2)[cH:12][cH:11][cH:10]1.[NH2:8][OH:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH:7]=[N:8][OH:9])[cH:10][cH:11][cH:12][c:13]1[O:14][c:15]1[n:16][c:17]([O:18][CH3:19])[cH:20][c:21]([O:22][CH3:2... | COC(=O)c1c(C=O)cccc1Oc1nc(OC)cc(OC)n1.NO | COC(=O)c1c(C=NO)cccc1Oc1nc(OC)cc(OC)n1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | c1ccc(Oc2ncccn2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH;D2;+0:1]=[N;H0;D2;+0:8]-[O;D1;H1:9]):[c:3] | 72 | [{"value": 72.0, "product": "COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate, 0.8 g of hydroxyamine hydrochloride, 1.1 g of potassium acetate and 10 ml of methanol were placed in a 50 ml eggplant type flask, and were stirred for 10 minutes at room temperature. Methanol was distilled off under reduced pressure, and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1ccccc1.c1cncnc1 | HO- | CO | null | 0.166667 | COC(=O)c1c(C=O)cccc1Oc1nc(OC)cc(OC)n1.NO>CO>COC(=O)c1c(C=NO)cccc1Oc1nc(OC)cc(OC)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-58d146d694ce48609c737e896ac57533 | CCOC(=O)C(C)Br.COC(=O)c1c(C=NO)cccc1Oc1nc(OC)cc(OC)n1>>CCOC(=O)C(C)ON=Cc1cccc(Oc2nc(OC)cc(OC)n2)c1C(=O)OC | COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NO.BrC(C(=O)OCC)C>>COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NOC(C)C(=O)OCC | Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[OH:8][N:9]=[CH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][c:17]2[n:18][c:19]([O:20][CH3:21])[cH:22][c:23]([O:24][CH3:25])[n:26]2)[c:27]1[C:28](=[O:29])[O:30][CH3:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[O:8][N:9]=[CH:10][c:11]1[cH:12][cH:13][cH:14][c:15](... | CCOC(=O)C(C)Br.COC(=O)c1c(C=NO)cccc1Oc1nc(OC)cc(OC)n1 | CCOC(=O)C(C)ON=Cc1cccc(Oc2nc(OC)cc(OC)n2)c1C(=O)OC | null | [Ag]=O | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 5b3220c592c1ff8e56030890b9220853f42f069aeea0537edf1f26ba44e3a466 | eaa3d712fa7ce293731d22b792157600787d0e3bec44c5b4827bc124713fbe82 | c1ccc(Oc2ncccn2)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[OH;D1;+0:7]-[#7:8]=[C:9]-[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:7]-[#7:8]=[C:9]-[c:10] | 27 | [{"value": 27.0, "product": "COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NOC(C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-hydroxyiminomethylbenzoate, 3 ml of ethyl 2-bromopropionate and 0.9 g of silver oxide (I) were place in a 50 ml eggplant type flask, and were allowed to stand for one night at room temperature. 10 ml of acetone and 10 g of silica gel were added to the resultant rea... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Oxime | Ester | null | null | c1ccccc1.c1cncnc1 | HBr | [Ag]=O.CC(=O)C | null | null | CCOC(=O)C(C)Br.COC(=O)c1c(C=NO)cccc1Oc1nc(OC)cc(OC)n1>[Ag]=O.CC(=O)C>CCOC(=O)C(C)ON=Cc1cccc(Oc2nc(OC)cc(OC)n2)c1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d4e0e0fd7a664fc7b02425517796a68b | COC(=O)c1c(O)cccc1C(C)=O.COC1=CC(OC)=NN(Cl)N1>>COC(=O)c1c(ON2N=C(OC)C=C(OC)N2)cccc1C(C)=O | C(C)(=O)C=1C=CC=C(C1C(=O)OC)O.[H-].[Na+].C1=CC=CC=C1.ClN1NC(=CC(=N1)OC)OC>>C(C)(=O)C1=C(C(=O)OC)C(=CC=C1)ON1NC(=CC(=N1)OC)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:18][cH:19][cH:20][c:21]1[C:22]([CH3:23])=[O:24].Cl[N:8]1[N:9]=[C:10]([O:11][CH3:12])[CH:13]=[C:14]([O:15][CH3:16])[NH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][N:8]2[N:9]=[C:10]([O:11][CH3:12])[CH:13]=[C:14]([O:15][CH3:16])[NH:17]2)[cH:18][cH:19][cH:20][c:21]1[C:22... | COC(=O)c1c(O)cccc1C(C)=O.COC1=CC(OC)=NN(Cl)N1 | COC(=O)c1c(ON2N=C(OC)C=C(OC)N2)cccc1C(C)=O | null | null | O | Miscellaneous | OtherReaction | 59ca52d02f18f6f1cf694bf6135fe35f5ebb54812490bc5f05c6acbea73cb85f | 353e49c7be80af9aebc634afb2cd1a6a6f10d92d32a4386b7fb0f5327d26735f | C1=CNN(Oc2ccccc2)N=C1 | Cl-[N;H0;D3;+0:1]1-[#7:2]-[C:3](-[#8:4])=[C:5]-[C:6](-[#8:7])=[#7:8]-1.[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13](-[OH;D1;+0:14]):[c:15]>>[#8:7]-[C:6]1=[#7:8]-[N;H0;D3;+0:1](-[O;H0;D2;+0:14]-[c:13](:[c:15]):[c:12]-[C:10](-[#8:9])=[O;D1;H0:11])-[#7:2]-[C:3](-[#8:4])=[C:5]-1 | 67 | [{"value": 67.0, "product": "C(C)(=O)C1=C(C(=O)OC)C(=CC=C1)ON1NC(=CC(=N1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "C(C)(=O)C1=C(C(=O)OC)C(=CC=C1)ON1NC(=CC(=N1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | 1.0 g of methyl 6-acetylsalicylate was added to a suspension solution of 0.23 g of sodium hydride and 30 ml of benzene, and the resultant mixture was stirred for 10 minutes at room temperature. 0.95 g of 2-chloro-4,6-dimethoxytriazine was added to the resultant mixture, and the mixture was stirred for one day and one n... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Hydrazone.Aromatic alcohol | Hydrazine.Hydrazone | C1=CN[NH]N=C1 | C1=CN[NH]N=C1 | c1ccccc1.C1=CN[NH]N=C1 | HCl | O | null | 24 | COC(=O)c1c(O)cccc1C(C)=O.COC1=CC(OC)=NN(Cl)N1>O>COC(=O)c1c(ON2N=C(OC)C=C(OC)N2)cccc1C(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9caf7f2af9b04e69903afed00c9e43d0 | COC(=O)c1c(ON2N=C(OC)C=C(OC)N2)cccc1C(C)=O.CON>>CON=C(C)c1cccc(ON2N=C(OC)C=C(OC)N2)c1C(=O)OC | C(C)(=O)C1=C(C(=O)OC)C(=CC=C1)ON1NC(=CC(=N1)OC)OC.Cl.CON.C(C)(=O)[O-].[K+].CO>>COC1=NN(NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C(C)=NOC | O=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][N:12]2[N:13]=[C:14]([O:15][CH3:16])[CH:17]=[C:18]([O:19][CH3:20])[NH:21]2)[c:22]1[C:23](=[O:24])[O:25][CH3:26].[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][N:3]=[C:4]([CH3:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][N:12]2[N:13]=[C:14]([O:15][CH3:16])[CH:17]=[C:18]([O:19][CH3:20]... | COC(=O)c1c(ON2N=C(OC)C=C(OC)N2)cccc1C(C)=O.CON | CON=C(C)c1cccc(ON2N=C(OC)C=C(OC)N2)c1C(=O)OC | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | C1=CNN(Oc2ccccc2)N=C1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H3:9]-[#8:10]-[NH2;D1;+0:11]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:3](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;H0;D2;+0:11]-[#8:10]-[C;D1;H3:9]):[c:4] | 48 | [{"value": 48.0, "product": "COC1=NN(NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C(C)=NOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.9 of methyl 2-acetyl-6-[(4,6-dimethoxytriazin-2-yl)oxy]benzoate, 0.68 g of methoxyamine hydrochloride and 0.80 g of potassium acetate were added to 30 ml of methanol, and the resultant mixture was stirred for one day and one night at room temperature. The resultant reaction liquor was poured into water, and was extra... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.C1=CN[NH]N=C1 | HO- | O | null | null | COC(=O)c1c(ON2N=C(OC)C=C(OC)N2)cccc1C(C)=O.CON>O>CON=C(C)c1cccc(ON2N=C(OC)C=C(OC)N2)c1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f731ed3622dd4070b9453e090fd140d9 | C=CCON.COC(=O)c1c(Oc2nc(OC)cc(OC)n2)cccc1C(C)=O>>C=CCON=C(C)c1cccc(Oc2nc(OC)cc(OC)n2)c1C(=O)OC | C(C)(=O)C1=C(C(=O)OC)C(=CC=C1)OC1=NC(=CC(=N1)OC)OC.Cl.C(C=C)ON.C(C)(=O)[O-].[K+].CO>>C(C=C)ON=C(C)C1=C(C(=O)OC)C(=CC=C1)OC1=NC(=CC(=N1)OC)OC | [CH2:1]=[CH:2][CH2:3][O:4][NH2:5].O=[C:6]([CH3:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][c:14]2[n:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[n:23]2)[c:24]1[C:25](=[O:26])[O:27][CH3:28]>>[CH2:1]=[CH:2][CH2:3][O:4][N:5]=[C:6]([CH3:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][c:14]2[n:15][c:16]([O:17][CH3:18])[... | C=CCON.COC(=O)c1c(Oc2nc(OC)cc(OC)n2)cccc1C(C)=O | C=CCON=C(C)c1cccc(Oc2nc(OC)cc(OC)n2)c1C(=O)OC | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | c1ccc(Oc2ncccn2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[C;D1;H2:9]=[C:10]-[C:11]-[#8:12]-[NH2;D1;+0:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:3](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;H0;D2;+0:13]-[#8:12]-[C:11]-[C:10]=[C;D1;H2:9]):[c:4] | 46.3 | [{"value": 46.0, "product": "C(C=C)ON=C(C)C1=C(C(=O)OC)C(=CC=C1)OC1=NC(=CC(=N1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.3, "product": "C(C=C)ON=C(C)C1=C(C(=O)OC)C(=CC=C1)OC1=NC(=CC(=N1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 1.0 g of methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, 1.0 g of allyloxyamine hydrochloride and 0.9 g of potassium acetate were added to 30 ml of methanol, and were refluxed with stirring for 5 hours. The reaction mixture was then poured into a cold water, and was extracted with ethyl acetate. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1cncnc1 | HO- | O | null | 5 | C=CCON.COC(=O)c1c(Oc2nc(OC)cc(OC)n2)cccc1C(C)=O>O>C=CCON=C(C)c1cccc(Oc2nc(OC)cc(OC)n2)c1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5f68bfe24502413aa07932d4095cc464 | BrCc1cccc(Br)c1.CCOP(OCC)OCC>>CCOP(=O)(Cc1cccc(Br)c1)OCC | BrC=1C=C(CBr)C=CC1.P(OCC)(OCC)OCC.C(C)Br>>BrC=1C=C(CP(OCC)(OCC)=O)C=CC1 | Br[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[cH:13]1.CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:14][CH2:15][CH3:16]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Br:12])[cH:13]1)[O:14][CH2:15][CH3:16] | BrCc1cccc(Br)c1.CCOP(OCC)OCC | CCOP(=O)(Cc1cccc(Br)c1)OCC | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C-[O;H0;D2;+0:5]-[P;H0;D3;+0:6](-[#8:7]-[C:8])-[#8:9]-[C:10]>>[C:8]-[#8:7]-[P;H0;D4;+0:6](=[O;H0;D1;+0:5])(-[#8:9]-[C:10])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 50 g (0.2 mol) of 3-bromobenzyl bromide and 33.2 g (0.2 mol) of triethyl phosphite were heated at 140° C. for 2 hours, during which ethyl bromide was distilled off. The product was distilled over a 30 cm Vigreux column.
Conditions: See reaction.notes.procedure_details.
Workup: was distilled off; The product was distill... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HBr | null | null | null | BrCc1cccc(Br)c1.CCOP(OCC)OCC>>CCOP(=O)(Cc1cccc(Br)c1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9bbd528effc4400bb7abc75186c3da13 | CC(C)OP(OC(C)C)OC(C)C.Cc1ccccc1CBr>>Cc1ccccc1CP(=O)(OC(C)C)OC(C)C | CC1=C(CBr)C=CC=C1.P(OC(C)C)(OC(C)C)OC(C)C>>CC1=C(CP(OC(C)C)(OC(C)C)=O)C=CC=C1 | CC(C)[O:10][P:9]([O:11][CH:12]([CH3:13])[CH3:14])[O:15][CH:16]([CH3:17])[CH3:18].Br[CH2:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][P:9](=[O:10])([O:11][CH:12]([CH3:13])[CH3:14])[O:15][CH:16]([CH3:17])[CH3:18] | CC(C)OP(OC(C)C)OC(C)C.Cc1ccccc1CBr | Cc1ccccc1CP(=O)(OC(C)C)OC(C)C | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C(-C)-[O;H0;D2;+0:5]-[P;H0;D3;+0:6](-[#8:7]-[C:8])-[#8:9]-[C:10]>>[C:8]-[#8:7]-[P;H0;D4;+0:6](=[O;H0;D1;+0:5])(-[#8:9]-[C:10])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 34.5 g (0.19 mol) of 2-methylbenzyl bromide and 39 g (0.19 mol) of triisopropyl phosphite were heated at 150° C. for 2 hours. During this procedure, i-propyl bromide distilled off. The product was distilled through a 30 cm Vigreux column.
Conditions: See reaction.notes.procedure_details.
Workup: During this procedure, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HBr | null | null | null | CC(C)OP(OC(C)C)OC(C)C.Cc1ccccc1CBr>>Cc1ccccc1CP(=O)(OC(C)C)OC(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-72cd4b260c0043e8aa2503a92dce1f5e | COC(=O)c1cccc(C)c1.O=C1CCC(=O)N1Br>>COC(=O)c1cccc(CBr)c1 | C1(=CC(=CC=C1)C(=O)OC)C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N>>BrCC=1C=C(C(=O)OC)C=CC1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[cH:12]1.O=C1CCC(=O)N1[Br:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][Br:11])[cH:12]1 | COC(=O)c1cccc(C)c1.O=C1CCC(=O)N1Br | COC(=O)c1cccc(CBr)c1 | null | null | null | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Methyl m-toluate was brominated with NBS and AIBN as described in Example 21 to give methyl m-bromomethylbenzoate, and this was further reacted with triethyl phosphite as described in Example 2 without further purification.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | null | null | null | COC(=O)c1cccc(C)c1.O=C1CCC(=O)N1Br>>COC(=O)c1cccc(CBr)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-67807ba4f6aa49a6bfa5666d55bc49c7 | Cc1ccccc1CC(=O)O.O=C1CCC(=O)N1Br>>CCOC(=O)Cc1ccccc1CBr | C1(=C(C=CC=C1)CC(=O)O)C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N>>BrCC1=C(C=CC=C1)CC(=O)OCC | [OH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH3:13].O=C1C[CH2:1][C:2](=O)N1[Br:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH2:13][Br:14] | Cc1ccccc1CC(=O)O.O=C1CCC(=O)N1Br | CCOC(=O)Cc1ccccc1CBr | null | null | null | Functional Group Interconversion | OtherReaction | 1362608f413d4bb6c464b165a96e5b3a887bb1d9ae8ab376765975b118a4d0c6 | 5765430870c89e3aab339fb3a79e6267a09f7a7000a9527aaa43f7b6538477a8 | c1ccccc1 | O=C1-C-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-N-1-[Br;H0;D1;+0:3].[CH3;D1;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[Br;H0;D1;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | o-Tolylacetic acid was brominated with NBS and AIBN as described in Example 21 to give ethyl o-bromomethylphenylacetate, and this was reacted with triethyl phosphite as described in Example 2.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Tertiary amide | Primary halide.Ester | C1CCNC1 | null | c1ccccc1 | HO- | null | null | null | Cc1ccccc1CC(=O)O.O=C1CCC(=O)N1Br>>CCOC(=O)Cc1ccccc1CBr |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1599d97756fc4192b03e40c6513b40d3 | CCOP(OCC)OCC.COc1ccc(CCl)cc1>>CCOP(=O)(Cc1ccc(OC)cc1)OCC | COC1=CC=C(CCl)C=C1.P(OCC)(OCC)OCC>>COC1=CC=C(CP(OCC)(OCC)=O)C=C1 | CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:15][CH2:16][CH3:17].Cl[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1)[O:15][CH2:16][CH3:17] | CCOP(OCC)OCC.COc1ccc(CCl)cc1 | CCOP(=O)(Cc1ccc(OC)cc1)OCC | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[P;H0;D3;+0:2](-[#8:3]-[C:4])-[#8:5]-[C:6].Cl-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[#8:3]-[P;H0;D4;+0:2](=[O;H0;D1;+0:1])(-[#8:5]-[C:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | p-Methoxybenzyl chloride was reacted with triethyl phosphite as described in Example 2.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HCl | null | null | null | CCOP(OCC)OCC.COc1ccc(CCl)cc1>>CCOP(=O)(Cc1ccc(OC)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d600937ba404454f851cb18c5c96b0b1 | BrBr.CCOP(=O)(Cc1ccccc1C)OCC>>CCOP(=O)(Cc1ccc(Br)cc1C)OCC | CC1=C(CP(OCC)(OCC)=O)C=CC=C1.BrBr>>CC1=C(CP(OCC)(OCC)=O)C=CC(=C1)Br | Br[Br:11].[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:12][c:13]1[CH3:14])[O:15][CH2:16][CH3:17]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]1[CH3:14])[O:15][CH2:16][CH3:17] | BrBr.CCOP(=O)(Cc1ccccc1C)OCC | CCOP(=O)(Cc1ccc(Br)cc1C)OCC | null | null | P(=O)(OC)(OC)OC.O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | null | [] | null | null | null | null | 10 g (42 mmol) of diethyl 2-methylbenzylphosphonate were dissolved in 60 ml of trimethyl phosphate and the solution was introduced into a flask protected from light and moisture. 16 g (0.05 mol) of Br2 were added dropwise, while stirring. The mixture was stirred at 90° C. for 15 hours and, after cooling, was diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | P(=O)(OC)(OC)OC.O | null | null | BrBr.CCOP(=O)(Cc1ccccc1C)OCC>P(=O)(OC)(OC)OC.O>CCOP(=O)(Cc1ccc(Br)cc1C)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3b1908a01a5143ef967011e4244289b7 | CCOP(=O)(Cc1ccccc1C)OCC.[O]=[Mn](=[O])(=[O])[O-]>>CCOP(=O)(Cc1ccccc1C(=O)O)OCC | OS(=O)(=O)O.CC1=C(CP(OCC)(OCC)=O)C=CC=C1.[O-][Mn](=O)(=O)=O.[K+].C(=O)([O-])[O-].[Na+].[Na+]>>C(=O)(O)C1=C(CP(OCC)(OCC)=O)C=CC=C1 | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH3:13])[O:16][CH2:17][CH3:18].[O]=[Mn](=[O])(=[O])[O-:15]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13](=[O:14])[OH:15])[O:16][CH2:17][CH3:18] | CCOP(=O)(Cc1ccccc1C)OCC.[O]=[Mn](=[O])(=[O])[O-] | CCOP(=O)(Cc1ccccc1C(=O)O)OCC | null | null | O | Acylation | OtherReaction | 7769a4cd09a67e270ac2d1d32df6b7a59b468ff590f9c59723b72ba3c8deb342 | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[c:4].[O-;H0;D1:5]-[Mn](=[O])(=[O])=[O]>>[O;D1;H0:6]=[C;H0;D3;+0:1](-[OH;D1;+0:5])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 4 g of diethyl 2-methylbenzylphosphonate were added to a solution of 12 g of KMnO4 and 4 g of Na2CO3 in 300 ml of water and the mixture was boiled under reflux for 24 hours. It was acidified with 15 ml of concentrated H2SO4 and extracted five times with 300 ml of ether each time. The organic phase was dried over MgSO4,... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1 | HO- | O | null | null | CCOP(=O)(Cc1ccccc1C)OCC.[O]=[Mn](=[O])(=[O])[O-]>O>CCOP(=O)(Cc1ccccc1C(=O)O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-88cb2fb8067f482b8c767b3656f1557f | CC12CCC(C(=O)OC1=O)C2(C)C.NCCCCN1CCN(c2ncccn2)CC1>>CC12CCC(C(=O)N(CCCCN3CCN(c4ncccn4)CC3)C1=O)C2(C)C | NCCCCN1CCN(CC1)C1=NC=CC=N1.CC1(C2CCC1(C(=O)OC2=O)C)C>>N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2(CCC(C1=O)C2(C)C)C)=O | O1[C:6](=[O:7])[CH:5]2[CH2:4][CH2:3][C:2]([CH3:1])([C:25]1=[O:26])[C:27]2([CH3:28])[CH3:29].[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[n:18][cH:19][cH:20][cH:21][n:22]2)[CH2:23][CH2:24]1>>[CH3:1][C:2]12[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[CH2:14... | CC12CCC(C(=O)OC1=O)C2(C)C.NCCCCN1CCN(c2ncccn2)CC1 | CC12CCC(C(=O)N(CCCCN3CCN(c4ncccn4)CC3)C1=O)C2(C)C | null | null | null | Acylation | OtherReaction | b2dab778bbababe3728f59be0984a9052d84b3f07c1a6627953660a5bd6e03d0 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2CCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | [C;D1;H3:1]-[C:2]12-[C:3]-[C:4](-[C:5]-[C:6]-1)-[C;H0;D3;+0:7](=[O;D1;H0:8])-O-[C;H0;D3;+0:9]-2=[O;D1;H0:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[N;H0;D3;+0:13]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:2]2(-[C;D1;H3:1])-[C:3]-[C:4](-[C:5]-[C:6]-2)-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 17 | [{"value": 17.0, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2(CCC(C1=O)C2(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 2.47 g (10.4 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine and 1.89 g (10.3 mmol) of dl-camphoric anhydride, substantially according to the procedure of Example 1. This afforded 0.7 g of product, mp 94°-97° C. (17% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC2COCC1C2 | C1CC2C[NH]CC1C2 | C1CC2C[NH]CC1C2.C1C[NH]CC[NH]1.c1cncnc1 | HO- | null | null | null | CC12CCC(C(=O)OC1=O)C2(C)C.NCCCCN1CCN(c2ncccn2)CC1>>CC12CCC(C(=O)N(CCCCN3CCN(c4ncccn4)CC3)C1=O)C2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ff612c52e1a04b8e97b7f6d47d01eb91 | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCC1C2>>O=C1C2CCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | NCCCCN1CCN(CC1)C1=NC=CC=N1.C12C(OC(C(CC1)C2)=O)=O>>N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)C2)=O | [NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([c:19]2[n:20][cH:21][cH:22][cH:23][n:24]2)[CH2:25][CH2:26]1.O1[C:2](=[O:1])[CH:3]2[CH2:4][CH2:5][CH:6]([CH2:7]2)[C:8]1=[O:9]>>[O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][CH:6]([CH2:7]2)[C:8](=[O:9])[N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17]... | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCC1C2 | O=C1C2CCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | null | null | null | Acylation | OtherReaction | b2dab778bbababe3728f59be0984a9052d84b3f07c1a6627953660a5bd6e03d0 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2CCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]2-[C:9]-[C:10]-[C:11]-1-[C:12]-2>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[C:11]2-[C:10]-[C:9]-[C:8](-[C:12]-2)-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 34 | [{"value": 34.0, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 1.92 g (8.2 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine and 1.14 g (8.14 mmol) of 3-oxabicyclo[3.2.1]octan-2,4-dione, substantially following the procedure of Example 1. Yield: 1.0 g (34% yield).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC2COCC1C2 | C1CC2C[NH]CC1C2 | C1CC2C[NH]CC1C2.C1C[NH]CC[NH]1.c1cncnc1 | HO- | null | null | null | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCC1C2>>O=C1C2CCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-443f179a2fda400bab688522515184dd | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCCC1C2>>O=C1C2CCCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | NCCCCN1CCN(CC1)C1=NC=CC=N1.C12C(OC(C(CCC1)C2)=O)=O>>N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCCC(C1=O)C2)=O | [NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([c:20]2[n:21][cH:22][cH:23][cH:24][n:25]2)[CH2:26][CH2:27]1.O1[C:2](=[O:1])[CH:3]2[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8]2)[C:9]1=[O:10]>>[O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8]2)[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1... | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCCC1C2 | O=C1C2CCCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | null | null | null | Acylation | OtherReaction | 6db7e0bce5132044bb5be71dd65c16d70e74c9d48d6d82239559f39783148260 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2CCCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[C:6]-[C:7](-[C:8])-[C;H0;D3;+0:9](=[O;D1;H0:10])-O-[C;H0;D3;+0:11]-1=[O;D1;H0:12]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:11](=[O;D1;H0:12])-[C:5](-[C:4])-[C:6]-[C:7](-[C:8])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | 47 | [{"value": 47.0, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCCC(C1=O)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.5, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCCC(C1=O)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following substantially the procedure of Example 1, 2.78 g (11.8 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine was reacted with 1.88 g (12.2 mmol) of 3-oxabicyclo[3.3.1]nonan-2,4-dione. The product was chromatographed on silica gel, eluting with dichloromethane/methanol (90:10), to give 2.04 g (47% yield) of t... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC2COCC(C1)C2 | C1CC2C[NH]CC(C1)C2 | C1CC2C[NH]CC(C1)C2.C1C[NH]CC[NH]1.c1cncnc1 | HO- | null | null | null | NCCCCN1CCN(c2ncccn2)CC1.O=C1OC(=O)C2CCCC1C2>>O=C1C2CCCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1790a349503649588a9f0cb35a4defe4 | CC1(C)C2CCC1C(=O)OC2=O.NCCCCN1CCN(c2ncccn2)CC1>>CC1(C)C2CCC1C(=O)N(CCCCN1CCN(c3ncccn3)CC1)C2=O | NCCCCN1CCN(CC1)C1=NC=CC=N1.CC1(C2C(OC(C1CC2)=O)=O)C>>N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)C2(C)C)=O | O1[C:8](=[O:9])[CH:7]2[C:2]([CH3:1])([CH3:3])[CH:4]([CH2:5][CH2:6]2)[C:27]1=[O:28].[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([c:19]2[n:20][cH:21][cH:22][cH:23][n:24]2)[CH2:25][CH2:26]1>>[CH3:1][C:2]1([CH3:3])[CH:4]2[CH2:5][CH2:6][CH:7]1[C:8](=[O:9])[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][N:1... | CC1(C)C2CCC1C(=O)OC2=O.NCCCCN1CCN(c2ncccn2)CC1 | CC1(C)C2CCC1C(=O)N(CCCCN1CCN(c3ncccn3)CC1)C2=O | null | null | null | Acylation | OtherReaction | b2dab778bbababe3728f59be0984a9052d84b3f07c1a6627953660a5bd6e03d0 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2CCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]2-[C:9]-[C:10]-1-[C:11]-[C:12]-2>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[C:10]2-[C:9]-[C:8](-[C:12]-[C:11]-2)-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 32 | [{"value": 32.0, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)C2(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.3, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)C2(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following substantially the procedure of Example 1, 0.54 g (2.34 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine was reacted with 0.36 g (2.14 mmol) of 8,8-dimethyl-3-oxabicyclo[3.2.1]octan-2,4-dione. The product was chromatographed on silica gel, eluting with dichloromethane/methanol (96:4), to give 0.25 g (32%... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC2COCC1C2 | C1CC2C[NH]CC1C2 | C1CC2C[NH]CC1C2.C1C[NH]CC[NH]1.c1cncnc1 | HO- | null | null | null | CC1(C)C2CCC1C(=O)OC2=O.NCCCCN1CCN(c2ncccn2)CC1>>CC1(C)C2CCC1C(=O)N(CCCCN1CCN(c3ncccn3)CC1)C2=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e56e486a103f4058a11eaf6d3e707e63 | CC12CCC(C)(C1)C(=O)OC2=O.NCCCCN1CCN(c2ncccn2)CC1>>CC12CCC(C)(C1)C(=O)N(CCCCN1CCN(c3ncccn3)CC1)C2=O | NCCCCN1CCN(CC1)C1=NC=CC=N1.CC12C(OC(C(CC1)(C2)C)=O)=O>>N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2(CCC(C1=O)(C2)C)C)=O | O1[C:8](=[O:9])[C:5]2([CH3:6])[CH2:4][CH2:3][C:2]([CH3:1])([CH2:7]2)[C:27]1=[O:28].[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([c:19]2[n:20][cH:21][cH:22][cH:23][n:24]2)[CH2:25][CH2:26]1>>[CH3:1][C:2]12[CH2:3][CH2:4][C:5]([CH3:6])([CH2:7]1)[C:8](=[O:9])[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][N... | CC12CCC(C)(C1)C(=O)OC2=O.NCCCCN1CCN(c2ncccn2)CC1 | CC12CCC(C)(C1)C(=O)N(CCCCN1CCN(c3ncccn3)CC1)C2=O | null | null | null | Acylation | OtherReaction | b2dab778bbababe3728f59be0984a9052d84b3f07c1a6627953660a5bd6e03d0 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C2CCC(C2)C(=O)N1CCCCN1CCN(c2ncccn2)CC1 | [C;D1;H3:1]-[C:2]12-[C:3]-[C:4]-[C:5](-[C;D1;H3:6])(-[C:7]-1)-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-[C;H0;D3;+0:10]-2=[O;D1;H0:11].[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[N;H0;D3;+0:14]1-[C;H0;D3;+0:10](=[O;D1;H0:11])-[C:2]2(-[C;D1;H3:1])-[C:3]-[C:4]-[C:5](-[C;D1;H3:6])(-[C:7]-2)-[C;H0;D3;+0:8]-1=[O;D1;H0:9] | 21 | [{"value": 21.0, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2(CCC(C1=O)(C2)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.4, "product": "N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2(CCC(C1=O)(C2)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following substantially the procedure of Example 1, 4.2 g (17.8 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine was reacted with 2.99 g (17.8 mmol) of 1,5-dimethyl-3-oxabicyclo[3.2.1]octan-2,4-dione. The product was chromatographed on silica gel, eluting with dichloromethane/methanol (96:4), to give 1.4 g (21% y... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC2COCC1C2 | C1CC2C[NH]CC1C2 | C1CC2C[NH]CC1C2.C1C[NH]CC[NH]1.c1cncnc1 | HO- | null | null | null | CC12CCC(C)(C1)C(=O)OC2=O.NCCCCN1CCN(c2ncccn2)CC1>>CC12CCC(C)(C1)C(=O)N(CCCCN1CCN(c3ncccn3)CC1)C2=O |
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