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-02ee2261663048188cf6d85d2cc96e3f | ord-1147dbdc36ea4a6199a9f7a5bb454589 | CN(C)CC(=O)Cl.Clc1ccc(C2CNc3ccccc3S2)cc1>>CN(C)CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | C(O)([O-])=O.[Na+].ClC1=CC=C(C=C1)C1SC2=C(NC1)C=CC=C2.CN(C1=CC=CC=C1)C.Cl.CN(C)CC(=O)Cl>>Cl.ClC1=CC=C(C=C1)C1SC2=C(N(C1)C(CN(C)C)=O)C=CC=C2 | Cl[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[O:6].[NH:7]1[CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[S:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[S:17][c:18]2[cH:19][cH:20][cH:21][cH:2... | CN(C)CC(=O)Cl.Clc1ccc(C2CNc3ccccc3S2)cc1 | CN(C)CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 4ce9986a2e7f31aa9eaa0925622c2cb2cd91fbaa9d58585e0420c051b9143356 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(C2CNc3ccccc3S2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[c:5]:[c:6]1:[c:7]-[#16:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#16:8]-[c:7]:[c:6]-1:[c:5] | 165.5 | [{"value": 86.0, "product": "Cl.ClC1=CC=C(C=C1)C1SC2=C(N(C1)C(CN(C)C)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 165.5, "product": "Cl.ClC1=CC=C(C=C1)C1SC2=C(N(C1)C(CN(C)C)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of 2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (0.52 g) and N,N-dimethylaniline (0.97 g) in methylene chloride (15 ml) is added dimethylaminoacetyl chloride hydrochloride (0.63 g) under ice cooling, and the mixture is stirred at the same temperature for 2.5 hours. To the reaction mixture is added ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)[NH]CCS2 | c1ccccc1.c1ccc2c(c1)[NH]CCS2 | HCl | C(Cl)Cl | null | 2.5 | CN(C)CC(=O)Cl.Clc1ccc(C2CNc3ccccc3S2)cc1>C(Cl)Cl>CN(C)CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-95b2bc44ff6d4a949fc4fdaff92f4f93 | C=CCBr.CNCC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21>>C=CCN(C)CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | C(C(=O)O)(=O)O.ClC1=CC=C(C=C1)C1SC2=C(N(C1)C(CNC)=O)C=CC=C2.C(C=C)Br.C([O-])([O-])=O.[K+].[K+]>>C(C(=O)O)(=O)O.C(C=C)N(C)CC(=O)N1CC(SC2=C1C=CC=C2)C2=CC=C(C=C2)Cl | Br[CH2:3][CH:2]=[CH2:1].[NH:4]([CH3:5])[CH2:6][C:7](=[O:8])[N:9]1[CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[S:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH2:1]=[CH:2][CH2:3][N:4]([CH3:5])[CH2:6][C:7](=[O:8])[N:9]1[CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[S:19][... | C=CCBr.CNCC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | C=CCN(C)CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | null | null | CN(C=O)C.CCOCC.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f41840cb514801a9cb1d5daa03acb2d980295bce2299a2397b84c433eee890b2 | 17be7e5233143f3f5efba3e4456f48662a03854e74790b373fce106317c9bff2 | c1ccc(C2CNc3ccccc3S2)cc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-[C;D1;H3:10])-[c:11]>>[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8]-[N;H0;D3;+0:9](-[C;D1;H3:10])-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[c:11] | null | [] | null | null | 3.5 | HOUR | A mixture of 2-(4-chlorophenyl)-4-(N-methylaminoacetyl)-3,4-dihydro-2H-1,4-benzothiazine (1.80 g), allyl bromide (0.52 ml), potassium carbonate (2.25 g) and dimethylformamide (20 ml) is stirred at room temperature for 3.5 hours. The reaction mixture is poured into water, and the mixture is extracted with ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine.Allyl | null | null | c1ccccc1.c1ccc2c(c1)[NH]CCS2 | HBr | CN(C=O)C.CCOCC.O | null | 3.5 | C=CCBr.CNCC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21>CN(C=O)C.CCOCC.O>C=CCN(C)CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a5b4bf891e840f68c2652294c346d36 | Clc1ccc(C2CNc3ccccc3S2)cc1.O=C(Cl)CCCBr>>O=C(CCCBr)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | BrCCCC(=O)Cl.ClC1=CC=C(C=C1)C1SC2=C(NC1)C=CC=C2.C(O)([O-])=O.[Na+]>>BrCCCC(=O)N1CC(SC2=C1C=CC=C2)C2=CC=C(C=C2)Cl | [NH:7]1[CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[S:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21.Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Br:6]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Br:6])[N:7]1[CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[S:17][c:18]2[cH:19][cH:20][cH:21][cH:22]... | Clc1ccc(C2CNc3ccccc3S2)cc1.O=C(Cl)CCCBr | O=C(CCCBr)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 | null | null | C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 4ce9986a2e7f31aa9eaa0925622c2cb2cd91fbaa9d58585e0420c051b9143356 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(C2CNc3ccccc3S2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]1:[c:7]-[#16:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#16:8]-[c:7]:[c:6]-1:[c:5] | 93.2 | [{"value": 93.0, "product": "BrCCCC(=O)N1CC(SC2=C1C=CC=C2)C2=CC=C(C=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "BrCCCC(=O)N1CC(SC2=C1C=CC=C2)C2=CC=C(C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 2-(4-chlorophenyl)-3,4-dihydro2H-1,4-benzothiazine (1.08 g), ethyl acetate (20 ml) and aqueous sodium hydrogen carbonate solution (20 ml) is added dropwise a solution of 4-bromobutyryl chloride (0.97 g) in ethyl acetate (5 ml) with stirring under ice cooling. The ethyl acetate layer is washed, dried and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)[NH]CCS2 | c1ccccc1.c1ccc2c(c1)[NH]CCS2 | HCl | C(C)(=O)OCC | null | null | Clc1ccc(C2CNc3ccccc3S2)cc1.O=C(Cl)CCCBr>C(C)(=O)OCC>O=C(CCCBr)N1CC(c2ccc(Cl)cc2)Sc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d1e1ce17b0b34812b37a771e23bf789c | COC(=O)C(Br)c1ccc(Cl)cc1.Nc1c(S)ccc2ccccc12>>O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1 | BrC(C(=O)OC)C1=CC=C(C=C1)Cl.NC1=C(C=CC2=CC=CC=C12)S.[BH4-].[Na+].C(C)(=O)[O-].[Na+]>>ClC1=CC=C(C=C1)C1C(NC2=C(S1)C=CC1=CC=CC=C12)=O | CO[C:2](=[O:1])[CH:15](Br)[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1.[NH2:3][c:4]1[c:5]([SH:14])[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[O:1]=[C:2]1[NH:3][c:4]2[c:5]([cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]23)[S:14][CH:15]1[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1 | COC(=O)C(Br)c1ccc(Cl)cc1.Nc1c(S)ccc2ccccc12 | O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1 | null | null | C(C)(=O)O.C(C)O | Acylation | OtherReaction | 53d82ac3f0d38fb5851aa99dbfefe9a4ff73a537ef0cc12e1d0268e0b7274d66 | 0d311a1a135375bdec380eecca73644efda9dc1d93d29933f0ae54267ce25440 | O=C1Nc2c(ccc3ccccc23)SC1c1ccccc1 | Br-[CH;D3;+0:1](-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-C)-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[SH;D1;+0:11]):[c:12]>>[O;D1;H0:3]=[C;H0;D3;+0:2]1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:12])-[S;H0;D2;+0:11]-[CH;D3;+0:1]-1-[c:4](:[c:5]):[c:6] | 86 | [{"value": 82.6, "product": "ClC1=CC=C(C=C1)C1C(NC2=C(S1)C=CC1=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "ClC1=CC=C(C=C1)C1C(NC2=C(S1)C=CC1=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 1-amino-2-naphthalenethiol (27.81 g) in ethanol (500 ml) is added sodium borohydride (11.35 g) at room temperature. The mixture is stirred for 20 minutes, and thereto is added dropwise acetic acid (200 ml) and is further added sodium acetate (24.6 g). To the mixture is further added dropwise methyl α-b... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Primary amine.Aromatic thiol | Secondary amide.Monosulfide | null | c1ccc2c3c(ccc2c1)SCCN3 | c1ccc2c3c(ccc2c1)SCCN3.c1ccccc1 | HBr | C(C)(=O)O.C(C)O | null | 0.333333 | COC(=O)C(Br)c1ccc(Cl)cc1.Nc1c(S)ccc2ccccc12>C(C)(=O)O.C(C)O>O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d364fc4681ef4cc7a031ee2d8b2fe643 | Nc1c(O)ccc2ccccc12.O=C(Cl)C(Br)c1ccc(Cl)cc1>>O=C1Nc2c(ccc3ccccc23)OC1c1ccc(Cl)cc1 | BrC(C(=O)Cl)C1=CC=C(C=C1)Cl.NC1=C(C=CC2=CC=CC=C12)O.CN(C1=CC=CC=C1)C.O1CCCC1>>ClC1=CC=C(C=C1)C1C(NC2=C(O1)C=CC1=CC=CC=C12)=O | [NH2:3][c:4]1[c:5]([OH:14])[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12.Cl[C:2](=[O:1])[CH:15](Br)[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1>>[O:1]=[C:2]1[NH:3][c:4]2[c:5]([cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]23)[O:14][CH:15]1[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1 | Nc1c(O)ccc2ccccc12.O=C(Cl)C(Br)c1ccc(Cl)cc1 | O=C1Nc2c(ccc3ccccc23)OC1c1ccc(Cl)cc1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 4275d4e72fa4cae93505c49688b37180c7ea1c3f136790e6de7cb9c829b330b6 | 968dd912eb527bc51bb564659dae4764ac7268f1407d56d6dfd83505e1fb909b | O=C1Nc2c(ccc3ccccc23)OC1c1ccccc1 | Br-[CH;D3;+0:1](-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[O;D1;H0:3]=[C;H0;D3;+0:2]1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:12])-[O;H0;D2;+0:11]-[CH;D3;+0:1]-1-[c:4](:[c:5]):[c:6] | 72.8 | [{"value": 72.8, "product": "ClC1=CC=C(C=C1)C1C(NC2=C(O1)C=CC1=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.7, "product": "ClC1=CC=C(C=C1)C1C(NC2=C(O1)C=CC1=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 1-amino-2-naphthol (9.4 g), N,N-dimethylaniline (17.87 g) and tetrahydrofuran (160 ml) is added dropwise α-bromo-4-chlorophenylacetyl chloride (18.97 g) under ice cooling, and the mixture is stirred for one hour. To the reaction mixture is added ethyl acetate, and the ethyl acetate layer is washed, drie... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Aromatic alcohol.Primary amine | Ether.Secondary amide | null | c1ccc2c3c(ccc2c1)OCCN3 | c1ccc2c3c(ccc2c1)OCCN3.c1ccccc1 | HCl.Br- | C(C)(=O)OCC | null | 1 | Nc1c(O)ccc2ccccc12.O=C(Cl)C(Br)c1ccc(Cl)cc1>C(C)(=O)OCC>O=C1Nc2c(ccc3ccccc23)OC1c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4b5c85fcaada4abfb59dac35958f1d2b | Nc1c(O)ccc2ccccc12>>O=C1COc2ccc3ccccc3c2N1 | NC1=C(C=CC2=CC=CC=C12)O.BrCC(=O)Cl>>N1C2=C(OCC1=O)C=CC1=CC=CC=C12 | [OH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[NH2:15]>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[NH:15]1 | Nc1c(O)ccc2ccccc12 | O=C1COc2ccc3ccccc3c2N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 67ea9da4c97625cabdeec5b016c0321aa5b03b650ac727c199462e36e87736ba | e85981153fdb0e665a2404e068a9f63c7c2f948afc7f5d5d2c9f013d0eb2c4a5 | O=C1COc2ccc3ccccc3c2N1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6]>>[O;D1;H0:7]=[C:8]1-[C:9]-[O;H0;D2;+0:5]-[c:4](:[c:6]):[c:2](:[c:3])-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | 1-Amino-2-naphthol and bromoacetyl chloride are reacted in the same manner as described in Example 32 to give 1H-naphtho[2,1-b][1,4]oxazin-2(3H)-one.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Ether.Secondary amide | null | c1ccc2c3c(ccc2c1)OCCN3 | c1ccc2c3c(ccc2c1)OCCN3 | Other | null | null | null | Nc1c(O)ccc2ccccc12>>O=C1COc2ccc3ccccc3c2N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ee847b13ba164bc9a59beaf98dc691e5 | O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1>>Clc1ccc(C2CNc3c(ccc4ccccc34)S2)cc1 | C([O-])([O-])=O.[K+].[K+].Cl.Cl.ClC1=CC=C(C=C1)C1C(NC2=C(S1)C=CC1=CC=CC=C12)=O.[BH4-].[Na+]>>ClC1=CC=C(C=C1)C1CNC2=C(S1)C=CC1=CC=CC=C12 | O=[C:7]1[CH:6]([c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:21][cH:20]2)[S:19][c:10]2[c:9]([c:18]3[c:13]([cH:12][cH:11]2)[cH:14][cH:15][cH:16][cH:17]3)[NH:8]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][NH:8][c:9]3[c:10]([cH:11][cH:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]34)[S:19]2)[cH:20][cH:21]1 | O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1 | Clc1ccc(C2CNc3c(ccc4ccccc34)S2)cc1 | null | null | CO.O1CCCC1 | Reduction | Reduction of secondary amides to amines | 2ea7dd52e6af34d147907152cf44b438e4018a10c611e8dc4e8602d2085edd4b | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(C2CNc3c(ccc4ccccc34)S2)cc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[c:3]:[c:4]-[#16:5]-[C:6]-1-[c:7]>>[c:7]-[C:6]1-[#16:5]-[c:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-1 | 88 | [{"value": 88.0, "product": "ClC1=CC=C(C=C1)C1CNC2=C(S1)C=CC1=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "ClC1=CC=C(C=C1)C1CNC2=C(S1)C=CC1=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (38.45 g) and sodium borohydride (22.32 g) in tetrahydrofuran (1.0 liter) is added dropwise with stirring boron trifluoride etherate complex (100 ml) at room temperature, and the mixture is refluxed for 2 hours. After cooling, to the mixture ar... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c3c(ccc2c1)SCCN3 | c1ccc2c3c(ccc2c1)SCCN3 | c1ccccc1.c1ccc2c3c(ccc2c1)SCCN3 | Other | CO.O1CCCC1 | null | null | O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1>CO.O1CCCC1>Clc1ccc(C2CNc3c(ccc4ccccc34)S2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5c1334df7ea540ff925a09322191a344 | C=CC(=O)Cl.Clc1ccc(C2CNc3c(ccc4ccccc34)S2)cc1>>C=CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 | C(C=C)(=O)Cl.ClC1=CC=C(C=C1)C1CNC2=C(S1)C=CC1=CC=CC=C12.C(O)([O-])=O.[Na+].O>>ClC1=CC=C(C=C1)C1CN(C2=C(S1)C=CC1=CC=CC=C12)C(C=C)=O | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[c:25]21>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][c:19]3[cH:20][c... | C=CC(=O)Cl.Clc1ccc(C2CNc3c(ccc4ccccc34)S2)cc1 | C=CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 13e096f01aae533e21ed92ead82f856bb03a412e2de5c75062337503f3448744 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(C2CNc3c(ccc4ccccc34)S2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[c:5]:[c:6]1:[c:7]-[#16:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H2:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#16:8]-[c:7]:[c:6]-1:[c:5] | 78 | [{"value": 78.0, "product": "ClC1=CC=C(C=C1)C1CN(C2=C(S1)C=CC1=CC=CC=C12)C(C=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "ClC1=CC=C(C=C1)C1CN(C2=C(S1)C=CC1=CC=CC=C12)C(C=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a mixture of 3-(4-chlorophenyl)-2,3-dihydro1H-naphtho[2,1-b][1,4]thiazine (1.50 g), sodium hydrogen carbonate (1.0 g), methylene chloride (30 ml) and water (15 ml) is added dropwise with stirring a solution of acryloyl chloride (0.90 g) in methylene chloride (10 ml) under ice cooling. The mixture is stirred at room ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c3c(ccc2c1)SCCN3 | c1ccc2c3c(ccc2c1)SCC[NH]3 | c1ccccc1.c1ccc2c3c(ccc2c1)SCC[NH]3 | HCl | C(Cl)Cl | null | 3 | C=CC(=O)Cl.Clc1ccc(C2CNc3c(ccc4ccccc34)S2)cc1>C(Cl)Cl>C=CC(=O)N1CC(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f9dddaae649d44ff923cca915bde63f6 | O=C1CSc2ccc3ccccc3c2N1.O=Cc1ccc(Cl)cc1>>O=C1Nc2c(ccc3ccccc23)SC1=Cc1ccc(Cl)cc1 | N1C2=C(SCC1=O)C=CC1=CC=CC=C12.ClC1=CC=C(C=O)C=C1.C[O-].[Na+].CN(C=O)C>>ClC1=CC=C(C=C2C(NC3=C(S2)C=CC2=CC=CC=C23)=O)C=C1 | [O:1]=[C:2]1[NH:3][c:4]2[c:5]([cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]23)[S:14][CH2:15]1.O=[CH:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[O:1]=[C:2]1[NH:3][c:4]2[c:5]([cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]23)[S:14][C:15]1=[CH:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1 | O=C1CSc2ccc3ccccc3c2N1.O=Cc1ccc(Cl)cc1 | O=C1Nc2c(ccc3ccccc23)SC1=Cc1ccc(Cl)cc1 | null | null | O | C-C Coupling | Aldol condensation | 66937d7b4a76007cd421456bab091c5cfeb6db5c29bd5c958d4d2ac9ac695b2d | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1Nc2c(ccc3ccccc23)SC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9]-[#16:10]-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9]-[#16:10]-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 52.8 | [{"value": 52.8, "product": "ClC1=CC=C(C=C2C(NC3=C(S2)C=CC2=CC=CC=C23)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (5.17 g), 4-chlorobenzaldehyde (5.62 g), sodium methoxide (1.73 g) and dimethylformamide (80 ml) is refluxed for 4.5 hours. After cooling, the reaction mixture is poured into water and the resulting precipitate is separated by filtration, washed and dried and then is... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | c1ccc2c3c(ccc2c1)SCCN3 | c1ccc2c3c(ccc2c1)SCCN3 | c1ccc2c3c(ccc2c1)SCCN3.c1ccccc1 | HO- | O | null | null | O=C1CSc2ccc3ccccc3c2N1.O=Cc1ccc(Cl)cc1>O>O=C1Nc2c(ccc3ccccc23)SC1=Cc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cda7d710b0294e50b3206a6efffce4f5 | Nc1c(O)ccc2ccccc12>>O=C1COc2ccc3ccccc3c2N1 | ClCC(=O)Cl.NC1=C(C=CC2=CC=CC=C12)O.CN(C1=CC=CC=C1)C.O1CCCC1>>N1C2=C(OCC1=O)C=CC1=CC=CC=C12 | [OH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[NH2:15]>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[NH:15]1 | Nc1c(O)ccc2ccccc12 | O=C1COc2ccc3ccccc3c2N1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 67ea9da4c97625cabdeec5b016c0321aa5b03b650ac727c199462e36e87736ba | e85981153fdb0e665a2404e068a9f63c7c2f948afc7f5d5d2c9f013d0eb2c4a5 | O=C1COc2ccc3ccccc3c2N1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6]>>[O;D1;H0:7]=[C:8]1-[C:9]-[O;H0;D2;+0:5]-[c:4](:[c:6]):[c:2](:[c:3])-[NH;D2;+0:1]-1 | null | [] | null | null | 1 | HOUR | To a mixture of 1-amino-2-naphthol (16.9 g), N,N-dimethylaniline (19.3 g) and tetrahydrofuran (200 ml) is added dropwise chloroacetyl chloride under ice cooling, and the mixture is stirred at the same temperature for one hour. To the reaction mixture is added ethyl acetate, and the ethyl acetate layer is washed, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Ether.Secondary amide | null | c1ccc2c3c(ccc2c1)OCCN3 | c1ccc2c3c(ccc2c1)OCCN3 | Other | C(C)(=O)OCC | null | 1 | Nc1c(O)ccc2ccccc12>C(C)(=O)OCC>O=C1COc2ccc3ccccc3c2N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b63569a6c9d54dc68412742b3466264e | ClCCCBr.O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1>>O=C1C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c2N1CCCCl | O.ClC1=CC=C(C=C1)C1C(NC2=C(S1)C=CC1=CC=CC=C12)=O.[OH-].[Na+].BrCCCCl>>ClC1=CC=C(C=C1)C1C(N(C2=C(S1)C=CC1=CC=CC=C12)CCCCl)=O | Br[CH2:23][CH2:24][CH2:25][Cl:26].[O:1]=[C:2]1[CH:3]([c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]2)[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[NH:22]1>>[O:1]=[C:2]1[CH:3]([c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]2)[S:11][c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[... | ClCCCBr.O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1 | O=C1C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c2N1CCCCl | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 4adc9480143dbc80763e1a86877be0a38ee2156c2063992a20b04359f152e8b7 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1Nc2c(ccc3ccccc23)SC1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[C:6]-[#16:7]-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:5](=[O;D1;H0:4])-[C:6]-[#16:7]-[c:8]:[c:9]-1:[c:10] | 65.1 | [{"value": 65.1, "product": "ClC1=CC=C(C=C1)C1C(N(C2=C(S1)C=CC1=CC=CC=C12)CCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one (10.0 g) and 96% sodium hydroxide (1.96 g) in dimethylsulfoxide (150 ml) is added 1-bromo-3-chloropropane (6.78 g) under ice cooling, and the mixture is stirred at room temperature overnight. The reaction mixture is poured into water, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c3c(ccc2c1)SCCN3 | c1ccc2c3c(ccc2c1)SCC[NH]3 | c1ccccc1.c1ccc2c3c(ccc2c1)SCC[NH]3 | HBr | CS(=O)C | null | 8 | ClCCCBr.O=C1Nc2c(ccc3ccccc23)SC1c1ccc(Cl)cc1>CS(=O)C>O=C1C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c2N1CCCCl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-97e988cbf7874191bfba8ed419f5f536 | CN(C)CCCCl.O=C1Nc2c(ccc3ccccc23)SC1c1cccc(C(F)(F)F)c1>>CN(C)CCCN1C(=O)C(c2cccc(C(F)(F)F)c2)Sc2ccc3ccccc3c21 | FC(C=1C=C(C=CC1)C1C(NC2=C(S1)C=CC1=CC=CC=C12)=O)(F)F.C([O-])([O-])=O.[K+].[K+].Cl.CN(CCCCl)C.CC(=O)C>>CN(CCCN1C2=C(SC(C1=O)C1=CC(=CC=C1)C(F)(F)F)C=CC1=CC=CC=C12)C | Cl[CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[NH:7]1[C:8](=[O:9])[CH:10]([c:11]2[cH:12][cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]2)[S:21][c:22]2[cH:23][cH:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]3[c:31]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][N:7]1[C:8](=[O:9])[CH:10]([c:11]2[cH:12][cH:13][cH:1... | CN(C)CCCCl.O=C1Nc2c(ccc3ccccc23)SC1c1cccc(C(F)(F)F)c1 | CN(C)CCCN1C(=O)C(c2cccc(C(F)(F)F)c2)Sc2ccc3ccccc3c21 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 4adc9480143dbc80763e1a86877be0a38ee2156c2063992a20b04359f152e8b7 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1Nc2c(ccc3ccccc23)SC1c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[C:6]-[#16:7]-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:5](=[O;D1;H0:4])-[C:6]-[#16:7]-[c:8]:[c:9]-1:[c:10] | null | [] | null | null | null | null | A mixture of 3-(3-trifluoromethylphenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (18.0 g), potassium carbonate (24.2 g), 3-(dimethylamino)propyl chloride hydrochloride (9.5 g), acetone (400 ml) and water (4 ml) is refluxed for 48 hours. The insoluble materials are filtered off and acetone is distilled off, and to the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c3c(ccc2c1)SCCN3 | c1ccc2c3c(ccc2c1)SCC[NH]3 | c1ccccc1.c1ccc2c3c(ccc2c1)SCC[NH]3 | HCl | O | null | null | CN(C)CCCCl.O=C1Nc2c(ccc3ccccc23)SC1c1cccc(C(F)(F)F)c1>O>CN(C)CCCN1C(=O)C(c2cccc(C(F)(F)F)c2)Sc2ccc3ccccc3c21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0dc1f01a584844b9b9fa0afdb4cd92ab | C=CCBr.CNCCCN1C(=O)C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21>>C=CCN(C)CCCN1C(=O)C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 | ClC1=CC=C(C=C1)C1C(N(C2=C(S1)C=CC1=CC=CC=C12)CCCNC)=O.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)N(C)CCCN1C2=C(SC(C1=O)C1=CC=C(C=C1)Cl)C=CC1=CC=CC=C12 | Br[CH2:3][CH:2]=[CH2:1].[NH:4]([CH3:5])[CH2:6][CH2:7][CH2:8][N:9]1[C:10](=[O:11])[CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[S:20][c:21]2[cH:22][cH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]3[c:30]21>>[CH2:1]=[CH:2][CH2:3][N:4]([CH3:5])[CH2:6][CH2:7][CH2:8][N:9]1[C:10](=[O:11])[CH:12]([c:13]2[cH:14][... | C=CCBr.CNCCCN1C(=O)C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 | C=CCN(C)CCCN1C(=O)C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f41840cb514801a9cb1d5daa03acb2d980295bce2299a2397b84c433eee890b2 | 17be7e5233143f3f5efba3e4456f48662a03854e74790b373fce106317c9bff2 | O=C1Nc2c(ccc3ccccc23)SC1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3] | null | [] | null | null | 8 | HOUR | To a mixture of 3-(4-chlorophenyl)-1-[3-(methylamino)propyl]-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (1.79 g), potassium carbonate (2.18 g) and acetone (50 ml) is added allyl bromide (0.65 g) under ice cooling, and the mixture is stirred at room temperature overnight. The insoluble materials are filtered off and aceton... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine.Allyl | null | null | c1ccccc1.c1ccc2c3c(ccc2c1)SCC[NH]3 | HBr | CC(=O)C | null | 8 | C=CCBr.CNCCCN1C(=O)C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21>CC(=O)C>C=CCN(C)CCCN1C(=O)C(c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3eb7ef4cd26f4320b6742ccfe2056cf7 | Clc1ccc(C2CNc3ccccc3S2)cc1.O=C(Cl)[C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1>>O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 | C(C)(=O)OCC.ClC1=CC=C(C=C1)C1SC2=C(NC1)C=CC=C2.C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N1[C@H](C(=O)Cl)CCC1>>ClC1=CC=C(C=C1)[C@H]1SC2=C(N(C1)C([C@H]1N(CCC1)S(=O)(=O)C1=CC3=CC=CC=C3C=C1)=O)C=CC=C2 | [NH:21]1[CH2:22][CH:23]([c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[S:31][c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21.Cl[C:2](=[O:1])[C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]1[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[cH:20]1>>[O:1]=[C:2]([C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]1... | Clc1ccc(C2CNc3ccccc3S2)cc1.O=C(Cl)[C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1 | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 | null | null | N1=CC=CC=C1 | Acylation | N-alkylation of secondary amines with alkyl halides | 4ce9986a2e7f31aa9eaa0925622c2cb2cd91fbaa9d58585e0420c051b9143356 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccccc2)Sc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[#16:6])-[C:7].[c:8]:[c:9]1:[c:10]-[#16:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#16:6]-[#7:5](-[C:7])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#16:11]-[c:10]:[c:9]-1:[c:8])-[C:4] | 51.5 | [{"value": 51.0, "product": "ClC1=CC=C(C=C1)[C@H]1SC2=C(N(C1)C([C@H]1N(CCC1)S(=O)(=O)C1=CC3=CC=CC=C3C=C1)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "ClC1=CC=C(C=C1)[C@H]1SC2=C(N(C1)C([C@H]1N(CCC1)S(=O)(=O)C1=CC3=CC=CC=C3C=C1)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD",... | null | null | 4 | HOUR | To a solution of (±)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (10.01 g, 0.038 mole) in pyridine (150 ml) is added (S)-N-(2-naphthalenesulfonyl)prolyl chloride (18.57 g, 0.057 mole), and the mixture is stirred at room temperature for 4 hours. To the reaction mixture is added ethyl acetate, and the mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)[NH]CCS2 | C1CC[NH]C1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2c(c1)[NH]CCS2 | HCl | N1=CC=CC=C1 | null | 4 | Clc1ccc(C2CNc3ccccc3S2)cc1.O=C(Cl)[C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1>N1=CC=CC=C1>O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-29f1c7d529084af1a2d53d160d01362e | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21>>Clc1ccc([C@@H]2CNc3ccccc3S2)cc1 | ClC1=CC=C(C=C1)[C@H]1SC2=C(N(C1)C([C@H]1N(CCC1)S(=O)(=O)C1=CC3=CC=CC=C3C=C1)=O)C=CC=C2.[OH-].[K+]>>ClC1=CC=C(C=C1)[C@H]1SC2=C(NC1)C=CC=C2 | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)[N:8]1[CH2:7][C@@H:6]([c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:17][cH:16]2)[S:15][c:14]2[c:9]1[cH:10][cH:11][cH:12][cH:13]2>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([C@@H:6]2[CH2:7][NH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[S:15]2)[cH:16][cH:17]1 | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 | Clc1ccc([C@@H]2CNc3ccccc3S2)cc1 | null | null | C(C)O.O | Reduction | Hydrogenolysis of tertiary amines | 27b97135537972bad0f39b33de27ca8c4def1d2ad25cb5b57fa6fd364a2b414f | 91c6782913bcf0652998fb08f2deeda6aa4f26f9c615d77e83ba2aee19bdb9b7 | c1ccc([C@@H]2CNc3ccccc3S2)cc1 | O=C(-[C@H]1-C-C-C-N-1-S(=O)(=O)-c1:c:c:c2:c:c:c:c:c:2:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#16:4]-[c:5]:[c:6]-1:[c:7]>>[c:7]:[c:6]1:[c:5]-[#16:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 58.7 | [{"value": 58.0, "product": "ClC1=CC=C(C=C1)[C@H]1SC2=C(NC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.7, "product": "ClC1=CC=C(C=C1)[C@H]1SC2=C(NC1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (R)-2-(4-Chlorophenyl)-4-[(S)-N-(2-naphthalenesulfonyl)prolyl]-3,4-dihydro-2H-1,4-benzothiazine (9.40 g, 0.017 mole) is suspended in ethanol-water (10:1, 188 ml), and thereto is added 86 % potassium hydroxide (11.2 g, 0.172 mole), and the mixture is refluxed for 30 minutes. The reaction mixture is poured into ice water... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amine | Secondary amine | C1CCNC1.c1ccc2ccccc2c1.c1ccc2c(c1)[NH]CCS2 | c1ccc2c(c1)NCCS2 | c1ccccc1.c1ccc2c(c1)NCCS2 | HO- | C(C)O.O | null | null | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21>C(C)O.O>Clc1ccc([C@@H]2CNc3ccccc3S2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d606b4fe377c4554b35432c5e54a1380 | Clc1ccc([C@@H]2CNc3ccccc3S2)cc1.O=C(Cl)CCl>>O=C(CCl)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 | ClCC(=O)Cl.ClC1=CC=C(C=C1)[C@H]1SC2=C(NC1)C=CC=C2.C(C)N(CC)CC>>ClCC(=O)N1C[C@H](SC2=C1C=CC=C2)C2=CC=C(C=C2)Cl | [NH:5]1[CH2:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[N:5]1[CH2:6][C@@H:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[S:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | Clc1ccc([C@@H]2CNc3ccccc3S2)cc1.O=C(Cl)CCl | O=C(CCl)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 4ce9986a2e7f31aa9eaa0925622c2cb2cd91fbaa9d58585e0420c051b9143356 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc([C@@H]2CNc3ccccc3S2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[c:5]:[c:6]1:[c:7]-[#16:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#16:8]-[c:7]:[c:6]-1:[c:5] | 108.8 | [{"value": 108.8, "product": "ClCC(=O)N1C[C@H](SC2=C1C=CC=C2)C2=CC=C(C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a suspension of (R)-(+)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (1.30 g, 0.005 mole) and triethylamine (1.66 ml, 0.012 mole) in dichloromethane (16 ml) is added dropwise a solution of chloroacetyl chloride (0.79 ml, 0.01 mole) in dichloromethane (4 ml) under ice cooling, and the mixture is stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)[NH]CCS2 | c1ccccc1.c1ccc2c(c1)[NH]CCS2 | HCl | ClCCl | null | 0.75 | Clc1ccc([C@@H]2CNc3ccccc3S2)cc1.O=C(Cl)CCl>ClCCl>O=C(CCl)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b83e9eb589e24776b7e8c40b1d8b288f | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccc3ccccc3c21>>Clc1ccc([C@@H]2CNc3c(ccc4ccccc34)S2)cc1 | ClC1=CC=C(C=C1)[C@@H]1CN(C2=C(S1)C=CC1=CC=CC=C12)C([C@H]1N(CCC1)S(=O)(=O)C1=CC2=CC=CC=C2C=C1)=O.[OH-].[K+]>>ClC1=CC=C(C=C1)[C@@H]1CNC2=C(S1)C=CC1=CC=CC=C12 | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)[N:8]1[CH2:7][C@@H:6]([c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:21][cH:20]2)[S:19][c:10]2[c:9]1[c:18]1[c:13]([cH:12][cH:11]2)[cH:14][cH:15][cH:16][cH:17]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([C@@H:6]2[CH2:7][NH:8][c:9]3[c:10]([cH:11][cH:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]34)[S:19]2)... | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccc3ccccc3c21 | Clc1ccc([C@@H]2CNc3c(ccc4ccccc34)S2)cc1 | null | null | C(C)O.O | Reduction | Hydrogenolysis of tertiary amines | b514bffa71b9beb3bb902be4236a98a774b9fdcf519e6fb38bec6b9a30856b76 | 91c6782913bcf0652998fb08f2deeda6aa4f26f9c615d77e83ba2aee19bdb9b7 | c1ccc([C@@H]2CNc3c(ccc4ccccc34)S2)cc1 | O=C(-[C@H]1-C-C-C-N-1-S(=O)(=O)-c1:c:c:c2:c:c:c:c:c:2:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#16:4]-[c:5]:[c:6]-1:[c:7]>>[c:7]:[c:6]1:[c:5]-[#16:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 63.1 | [{"value": 63.0, "product": "ClC1=CC=C(C=C1)[C@@H]1CNC2=C(S1)C=CC1=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "ClC1=CC=C(C=C1)[C@@H]1CNC2=C(S1)C=CC1=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (R)-3-(4-chlorophenyl)-1-[(S)-N-(2-naphthalenesulfonyl)prolyl]-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (11.50 g, 0.019 mole), 86 % potassium hydroxide (15.0 g, 0.227 mole) and ethanol-water (10:1, 230 ml) is refluxed under argon for one hour. The reaction mixture is poured into ice water and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amine | Secondary amine | C1CCNC1.c1ccc2ccccc2c1.c1ccc2c3c(ccc2c1)SCC[NH]3 | c1ccc2c3c(ccc2c1)SCCN3 | c1ccccc1.c1ccc2c3c(ccc2c1)SCCN3 | HO- | C(C)O.O | null | null | O=C([C@@H]1CCCN1S(=O)(=O)c1ccc2ccccc2c1)N1C[C@@H](c2ccc(Cl)cc2)Sc2ccc3ccccc3c21>C(C)O.O>Clc1ccc([C@@H]2CNc3c(ccc4ccccc34)S2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c9f7e092e3be4773aba7a95c56f0342d | COC(=O)C(Br)c1ccc(F)cc1.Nc1ccccc1S>>O=C1Nc2ccccc2SC1c1ccc(F)cc1 | NC1=C(C=CC=C1)S.C(C)(=O)[O-].[Na+].BrC(C(=O)OC)C1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C1SC2=C(NC1=O)C=CC=C2 | CO[C:2](=[O:1])[CH:11](Br)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.[NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[SH:10]>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][CH:11]1[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | COC(=O)C(Br)c1ccc(F)cc1.Nc1ccccc1S | O=C1Nc2ccccc2SC1c1ccc(F)cc1 | null | null | C(C)O | Acylation | OtherReaction | ef04caa15007f4e105feafaf3f6b6625bf2b39041c50ed5e834ec312da7add5b | 0d311a1a135375bdec380eecca73644efda9dc1d93d29933f0ae54267ce25440 | O=C1Nc2ccccc2SC1c1ccccc1 | Br-[CH;D3;+0:1](-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-C)-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[SH;D1;+0:11]):[c:12]>>[O;D1;H0:3]=[C;H0;D3;+0:2]1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:12])-[S;H0;D2;+0:11]-[CH;D3;+0:1]-1-[c:4](:[c:5]):[c:6] | 87.6 | [{"value": 87.6, "product": "FC1=CC=C(C=C1)C1SC2=C(NC1=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 2-aminothiophenol (12.6 g) and sodium acetate (23.6 g) in ethanol (150 ml) is added methyl α-bromo-4-fluorophenylacetate (23.6 g), and the mixture is stirred at room temperature overnight. After the solvent is distilled off, water is added to the residue. The resulting precipitate is separated by fil... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Primary amine.Aromatic thiol | Secondary amide.Monosulfide | null | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)NCCS2.c1ccccc1 | HBr | C(C)O | null | 8 | COC(=O)C(Br)c1ccc(F)cc1.Nc1ccccc1S>C(C)O>O=C1Nc2ccccc2SC1c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-82405db35af04c76bc822593939f548f | CCO.Nc1ccc(Cl)cc1S>>O=C1Nc2ccc(Cl)cc2SC1c1ccc(Cl)cc1 | NC1=C(C=C(C=C1)Cl)S.[OH-].[K+].C(C)O>>ClC1=CC2=C(NC(C(S2)C2=CC=C(C=C2)Cl)=O)C=C1 | [OH:1][CH2:2][CH3:13].[NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]1[SH:11]>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[S:11][CH:12]1[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1 | CCO.Nc1ccc(Cl)cc1S | O=C1Nc2ccc(Cl)cc2SC1c1ccc(Cl)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8b26c5c8012c07d94fee764de08eb10a6a67b506d3b4b1d07683c6d3fa48e2d8 | 8c90e99e40217915a4051c7308057672015b15912f4e38a865719bfa778d636f | O=C1Nc2ccccc2SC1c1ccccc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[OH;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[SH;D1;+0:8]):[c:9]>>[O;H0;D1;+0:3]=[C;H0;D3;+0:2]1-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:9])-[S;H0;D2;+0:8]-[C:10]-1-[c;H0;D3;+0:1](:[c:11]:[c:12]):[c:13]:[c:14] | null | [] | null | null | null | null | To a solution of 2-amino-5-chlorothiophenol (4.49 g) in ethanol (30 ml) is added 96 % potassium hydroxide (1.63 g), and the mixture is distilled to remove ethanol. The resulting solid material is suspended in toluene (70 ml) and thereto is added methyl ° -bromo-4-chlorophenylacetate (7.38 g), and the mixture is refluxe... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine.Aromatic thiol | Aromatic halide.Secondary amide.Monosulfide | null | c1ccc2c(c1)NCCS2.c1ccccc1 | c1ccc2c(c1)NCCS2.c1ccccc1 | Other | null | null | null | CCO.Nc1ccc(Cl)cc1S>>O=C1Nc2ccc(Cl)cc2SC1c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9f13dedfca454f268811c8281667b82c | O=C1Nc2ccccc2SC1Cl.c1ccsc1>>O=C1Nc2ccccc2SC1c1cccs1 | ClC1SC2=C(NC1=O)C=CC=C2.S1C=CC=C1>>O=C1C(SC2=C(N1)C=CC=C2)C=2SC=CC2 | Cl[CH:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10]1.[cH:12]1[cH:13][cH:14][cH:15][s:16]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[S:10][CH:11]1[c:12]1[cH:13][cH:14][cH:15][s:16]1 | O=C1Nc2ccccc2SC1Cl.c1ccsc1 | O=C1Nc2ccccc2SC1c1cccs1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | e09baf973037580f30ee32c3c704f929e3c2ec770c8c9be6b0c240617ac22ed2 | d95f847e86e1cc3f2cf41afa59b10431a16bb750a300256ba48481198c61f22d | O=C1Nc2ccccc2SC1c1cccs1 | Cl-[CH;D3;+0:1]1-[#16:2]-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[#16;a:8]1:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[#16:2]-[CH;D3;+0:1]-1-[c;H0;D3;+0:12]1:[#16;a:8]:[c:9]:[c:10]:[c:11]:1 | 70.3 | [{"value": 70.3, "product": "O=C1C(SC2=C(N1)C=CC=C2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of 2-chloro-3-oxo-3,4-dihydro-2H-1,4-benzothiazine (9.38 g) and thiophene (7.91 g) in methylene chloride (250 ml) is added in portions stannic chloride (12. 2 g) at 0° to 5° C. After stirring at the same temperature for 45 minutes, the mixture is poured into ice water, and the organic layer is separated. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Monosulfide | Monosulfide | c1ccc2c(c1)NCCS2.c1ccsc1 | c1ccc2c(c1)NCCS2.c1ccsc1 | c1ccc2c(c1)NCCS2.c1ccsc1 | HCl | C(Cl)Cl | null | 0.75 | O=C1Nc2ccccc2SC1Cl.c1ccsc1>C(Cl)Cl>O=C1Nc2ccccc2SC1c1cccs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ffca69bda88f4569b98eca5bd5ca7c45 | Nc1ccccc1O.O=C(Cl)Cc1ccc(Cl)cc1Br>>O=C1Nc2ccccc2OC1c1ccc(Cl)cc1 | NC1=C(C=CC=C1)O.C(O)([O-])=O.[Na+].BrC1=C(C=CC(=C1)Cl)CC(=O)Cl>>ClC1=CC=C(C=C1)C1OC2=C(NC1=O)C=CC=C2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:10].Cl[C:2](=[O:1])[CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]1Br>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[O:10][CH:11]1[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | Nc1ccccc1O.O=C(Cl)Cc1ccc(Cl)cc1Br | O=C1Nc2ccccc2OC1c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C.O.C(C)(=O)OCC | Acylation | OtherReaction | b3b78455d1541494347c438dea59929d6b932540589b76e29a890849e6616cf3 | a50a5a7621887766aee8dfd49ef6ba1d93494cd0850afc2078fb283e97eaa7c4 | O=C1Nc2ccccc2OC1c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[CH2;D2;+0:5]-[C;H0;D3;+0:6](-Cl)=[O;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[O;D1;H0:7]=[C;H0;D3;+0:6]1-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12](:[c:14])-[O;H0;D2;+0:13]-[CH;D3;+0:5]-1-[c:4](:[c:8]):[cH;D2;+0:1]:[c:2]:[c:3] | 76.9 | [{"value": 76.9, "product": "ClC1=CC=C(C=C1)C1OC2=C(NC1=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-aminophenol (13.5 g) in ethyl acetate (150 ml) is added a solution of sodium hydrogen carbonate (15 g) in water (300 ml), and to the mixture is added dropwise a solution of o-bromo-4-chlorophenylacetyl chloride (32.2 g) in toluene with vigorous stirring under ice cooling. After the mixture is stirred... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Aromatic alcohol.Primary amine | Ether.Secondary amide | c1ccccc1 | c1ccc2c(c1)NCCO2.c1ccccc1 | c1ccc2c(c1)NCCO2.c1ccccc1 | HCl.Br- | C1(=CC=CC=C1)C.O.C(C)(=O)OCC | null | null | Nc1ccccc1O.O=C(Cl)Cc1ccc(Cl)cc1Br>C1(=CC=CC=C1)C.O.C(C)(=O)OCC>O=C1Nc2ccccc2OC1c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c66e87f2688c4345b675a14629eb0241 | COc1cc(N)cc(OC)c1OC.O=C(Cl)Cl>>COc1cc(N=C=O)cc(OC)c1OC | COC=1C=C(N)C=C(C1OC)OC.C(=O)(Cl)Cl>>COC=1C=C(C=C(C1OC)OC)N=C=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:9][c:10]([O:11][CH3:12])[c:13]1[O:14][CH3:15].Cl[C:7](Cl)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[C:7]=[O:8])[cH:9][c:10]([O:11][CH3:12])[c:13]1[O:14][CH3:15] | COc1cc(N)cc(OC)c1OC.O=C(Cl)Cl | COc1cc(N=C=O)cc(OC)c1OC | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A mixture of 3,4,5-trimethoxyaniline (365 mg; 2.0 mmol) in toluene (20 ml) and phosgene (6 ml 20% in toluene; 12 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4,5-trimethoxyphenylisocyanate. The crude product was added 3-[4-(4-chloro-phenyl)-1-piperazinyl]propanol (800 mg; 3... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | COc1cc(N)cc(OC)c1OC.O=C(Cl)Cl>C1(=CC=CC=C1)C>COc1cc(N=C=O)cc(OC)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dca1c35f5eed401ebd1117828fd2510f | COc1cc(N=C=O)cc(OC)c1OC.OCCCN1CCN(c2ccccc2Cl)CC1>>COc1cc(NC(=O)OCCCN2CCN(c3ccccc3Cl)CC2)cc(OC)c1OC.Cl | COC=1C=C(C=C(C1OC)OC)N=C=O.ClC1=C(C=CC=C1)N1CCN(CC1)CCCO>>Cl.ClC1=C(C=CC=C1)N1CCN(CC1)CCCOC(NC1=CC(=C(C(=C1)OC)OC)OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[C:7]=[O:8])[cH:26][c:27]([O:28][CH3:29])[c:30]1[O:31][CH3:32].[OH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[Cl:23])[CH2:24][CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14... | COc1cc(N=C=O)cc(OC)c1OC.OCCCN1CCN(c2ccccc2Cl)CC1 | COc1cc(NC(=O)OCCCN2CCN(c3ccccc3Cl)CC2)cc(OC)c1OC.Cl | null | null | C1(=CC=CC=C1)C | Functional Group Addition | OtherReaction | 34d9ad98d9a519aaecd6e015a244150bbfa3600dd09e6201754e52ac29fbfc08 | 749ae4443961a38d2a0225bbc57a43774fc1f268e60fddcfd625ac303c5d593c | O=C(Nc1ccccc1)OCCCN1CCN(c2ccccc2)CC1 | [C:1]-[C:2]-[OH;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 40 | [{"value": 40.0, "product": "Cl.ClC1=C(C=CC=C1)N1CCN(CC1)CCCOC(NC1=CC(=C(C(=C1)OC)OC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,4,5-trimethoxyphenylisocyanate (420 mg; 2.0 mmol) (produced as in Example 1) and 3-[4-(2-chloro-phenyl) -1-piperazinyl]propanol (500 mg; 20 mmol) in toluene (25 ml) was refluxed for 16 h. The solvent was evaporated and the residue taken up in ethanol, which was treated with hydrogen chloride in ether. Re... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary alcohol | Carbamic ester.Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | COc1cc(N=C=O)cc(OC)c1OC.OCCCN1CCN(c2ccccc2Cl)CC1>C1(=CC=CC=C1)C>COc1cc(NC(=O)OCCCN2CCN(c3ccccc3Cl)CC2)cc(OC)c1OC.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e06146ed2854458e91b224a994c85528 | Nc1ccc2c(c1)OCCO2.S=C(Cl)Cl>>S=C=Nc1ccc2c(c1)OCCO2 | C(=S)(Cl)Cl.O1CCOC2=C1C=CC(=C2)N.C(C)N(CC)CC>>C1OC=2C=C(C=CC2OC1)N=C=S | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2.Cl[C:2](Cl)=[S:1]>>[S:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2 | Nc1ccc2c(c1)OCCO2.S=C(Cl)Cl | S=C=Nc1ccc2c(c1)OCCO2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | c1ccc2c(c1)OCCO2 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[S;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 37.3 | [{"value": 37.3, "product": "C1OC=2C=C(C=CC2OC1)N=C=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 30 | MINUTE | To a mixture of 1,4-benzodioxan-6-amine (15.1 g; 100 mmol) and triethylamine (20.2 g, 200 ml) in toluene (350 ml) was added dropwise over 10 min. thiophosgene (11.5 g, 100 mmol) in toluene (50 ml). The mixture was stirred at 80° C. for 30 min., cooled to room temperature and filtered. The filtrate was evaporated. The p... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | c1ccc2c(c1)OCCO2 | HCl | C1(=CC=CC=C1)C | 80 | 0.5 | Nc1ccc2c(c1)OCCO2.S=C(Cl)Cl>C1(=CC=CC=C1)C>S=C=Nc1ccc2c(c1)OCCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ec421ddd018040c2b602d046cea0785d | Nc1ccc2c(c1)OCO2.O=C(Cl)Cl>>O=C=Nc1ccc2c(c1)OCO2 | C1OC=2C=C(N)C=CC2O1.C(=O)(Cl)Cl>>C1OC=2C=C(C=CC2O1)N=C=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][O:12]2.Cl[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][O:12]2 | Nc1ccc2c(c1)OCO2.O=C(Cl)Cl | O=C=Nc1ccc2c(c1)OCO2 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccc2c(c1)OCO2 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A mixture of 3,4-methylenedioxyaniline (275 mg; 2.0 mmol) in toluene (15 ml) and phosgene (4.75 ml; 20% in toluene; 9 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4-methylenedioxyphenylisocyanate. The crude product was added to 3-[4-(2-chlorophenyl) -1-piperazinyl]propanol ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccc2c(c1)OCO2 | HCl | C1(=CC=CC=C1)C | null | null | Nc1ccc2c(c1)OCO2.O=C(Cl)Cl>C1(=CC=CC=C1)C>O=C=Nc1ccc2c(c1)OCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b553bc63e457446caa9f52fa9caba4ba | O=C=Nc1ccc2c(c1)OCO2.OCCCN1CCN(c2cccc(Cl)c2)CC1>>Cl.O=C(Nc1ccc2c(c1)OCO2)OCCCN1CCN(c2cccc(Cl)c2)CC1 | C1OC=2C=C(C=CC2O1)N=C=O.ClC=1C=C(C=CC1)N1CCN(CC1)CCCO>>Cl.ClC=1C=C(C=CC1)N1CCN(CC1)CCCOC(NC1=CC2=C(C=C1)OCO2)=O | [O:2]=[C:3]=[N:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2.[Cl:1][c:26]1[cH:25][cH:24][cH:23][c:22]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][CH2:15][OH:14])[CH2:30][CH2:29]2)[cH:28]1>>[ClH:1].[O:2]=[C:3]([NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2)[O:14][CH2:15][CH2:16][C... | O=C=Nc1ccc2c(c1)OCO2.OCCCN1CCN(c2cccc(Cl)c2)CC1 | Cl.O=C(Nc1ccc2c(c1)OCO2)OCCCN1CCN(c2cccc(Cl)c2)CC1 | null | null | C1(=CC=CC=C1)C | Functional Group Addition | OtherReaction | 03272b0c5aa652494ac2f116e11a111ca0a8f4a154a2c5aa7f923f1b9462e4fa | ef2b96a1cd95bf992d35bdeceef9b4d2e52432f8cfdccbdcdd90004727b90133 | O=C(Nc1ccc2c(c1)OCO2)OCCCN1CCN(c2ccccc2)CC1 | [C:1]-[C:2]-[OH;D1;+0:3].[Cl;H0;D1;+0:4]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[O;D1;H0:10]=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15].[Cl;D1;H0:16]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[ClH;D0;+0:4] | 187.1 | [{"value": 187.1, "product": "Cl.ClC=1C=C(C=CC1)N1CCN(CC1)CCCOC(NC1=CC2=C(C=C1)OCO2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,4-methylenedioxyphenylisocyanate (330 mg; 2.0 mmol) (produced as in Example 13) and 3-[4-(3-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (30 ml) was refluxed for 16 h. The reaction mixture was then concentrated and submitted to flash chromatography on silica gel 60 eluting with tol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Primary alcohol | Aromatic halide.Carbamic ester.Ether | c1ccccc1 | c1ccccc1 | c1ccc2c(c1)OCO2.C1C[NH]CC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | O=C=Nc1ccc2c(c1)OCO2.OCCCN1CCN(c2cccc(Cl)c2)CC1>C1(=CC=CC=C1)C>Cl.O=C(Nc1ccc2c(c1)OCO2)OCCCN1CCN(c2cccc(Cl)c2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-14741824b5af4f6e81afacd2442b897f | Nc1ccc2c(c1)OCCO2.O=C(Cl)Cl>>O=C=Nc1ccc2c(c1)OCCO2 | O1CCOC2=C1C=CC(=C2)N.C(=O)(Cl)Cl>>C1OC=2C=C(C=CC2OC1)N=C=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2.Cl[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2 | Nc1ccc2c(c1)OCCO2.O=C(Cl)Cl | O=C=Nc1ccc2c(c1)OCCO2 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccc2c(c1)OCCO2 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A mixture of 1,4-benzodioxan-6-amine (300 mg; 2.0 mmol) in toluene (20 ml) and phosgene (10 ml 20% in toluene; 19 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4-ethylenedioxyphenylisocyanate. The crude product was added 3-[4-(4-chlorophenyl)-1-piperazinyl]propanol (500 mg; ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccc2c(c1)OCCO2 | HCl | C1(=CC=CC=C1)C | null | null | Nc1ccc2c(c1)OCCO2.O=C(Cl)Cl>C1(=CC=CC=C1)C>O=C=Nc1ccc2c(c1)OCCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a42846c208cf4c61a676ead8d617e1cf | O=C=Nc1ccc2c(c1)OCCO2.OCCCN1CCN(c2ccccc2Cl)CC1>>Cl.O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2ccccc2Cl)CC1 | C1OC=2C=C(C=CC2OC1)N=C=O.ClC1=C(C=CC=C1)N1CCN(CC1)CCCO>>Cl.ClC1=C(C=CC=C1)N1CCN(CC1)CCCOC(NC1=CC2=C(C=C1)OCCO2)=O | [O:2]=[C:3]=[N:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][CH2:13][O:14]2.[Cl:1][c:28]1[c:23]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][OH:15])[CH2:31][CH2:30]2)[cH:24][cH:25][cH:26][cH:27]1>>[ClH:1].[O:2]=[C:3]([NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][CH2:13][O:14]2)[O:15][C... | O=C=Nc1ccc2c(c1)OCCO2.OCCCN1CCN(c2ccccc2Cl)CC1 | Cl.O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2ccccc2Cl)CC1 | null | null | C1(=CC=CC=C1)C | Functional Group Addition | OtherReaction | 03272b0c5aa652494ac2f116e11a111ca0a8f4a154a2c5aa7f923f1b9462e4fa | ef2b96a1cd95bf992d35bdeceef9b4d2e52432f8cfdccbdcdd90004727b90133 | O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2ccccc2)CC1 | [#7:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[Cl;H0;D1;+0:5]):[c:6]:[c:7].[C:8]-[C:9]-[OH;D1;+0:10].[O;D1;H0:11]=[C;H0;D2;+0:12]=[N;H0;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[#7:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[Cl;D1;H0:17]):[c:6]:[c:7].[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:12](=[O;D1;H0:11])-[NH;D2;+0:13]-[c:14](:[c:15]):[c:16]... | 70.5 | [{"value": 70.5, "product": "Cl.ClC1=C(C=CC=C1)N1CCN(CC1)CCCOC(NC1=CC2=C(C=C1)OCCO2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,4-ethylenedioxyphenylisocyanate (2.0 mmol) (produced as in Example 16) and 3-[4-(2-chlorophenyl)-1piperazinyl]propanol (500 mg; 2.0 mmol) in toluene (10 ml) was refluxed for 16 h. The reaction mixture was then concentrated and submitted to flash chromatography on silica gel 60 eluting with toluene gradua... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Primary alcohol | Aromatic halide.Carbamic ester.Ether | c1ccccc1 | c1ccccc1 | c1ccc2c(c1)OCCO2.C1C[NH]CC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | O=C=Nc1ccc2c(c1)OCCO2.OCCCN1CCN(c2ccccc2Cl)CC1>C1(=CC=CC=C1)C>Cl.O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2ccccc2Cl)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3d190deb557247cdb727663a5f9389e8 | Nc1ccc2ncsc2c1.O=C(Cl)Cl>>O=C=Nc1ccc2ncsc2c1 | NC1=CC2=C(N=CS2)C=C1.C(=O)(Cl)Cl>>S1C=NC2=C1C=C(C=C2)N=C=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][s:10][c:11]2[cH:12]1.Cl[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][s:10][c:11]2[cH:12]1 | Nc1ccc2ncsc2c1.O=C(Cl)Cl | O=C=Nc1ccc2ncsc2c1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccc2scnc2c1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[#16;a:3]:[c:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8]>>[#16;a:3]:[c:4]:[c:5]:[c:6](-[N;H0;D2;+0:7]=[C;H0;D2;+0:1]=[O;D1;H0:2]):[c:8] | null | [] | null | null | null | null | A mixture of 6-aminobenzothiazole (600 mg; 4 mmol) in toluene (40 ml) and phosgene (20 ml 20% in toluene; 40 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 6-benzothiazolylisocyanate. To the crude product was added 3-[4-(4-chlorophenyl)-1-piperazinyl]propanol (500 mg; 2.0 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccc2scnc2c1 | HCl | C1(=CC=CC=C1)C | null | null | Nc1ccc2ncsc2c1.O=C(Cl)Cl>C1(=CC=CC=C1)C>O=C=Nc1ccc2ncsc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b58f39396da84e4494e3cd059717395f | Nc1cc(Cl)c(Cl)c(Cl)c1.O=C(Cl)Cl>>O=C=Nc1cc(Cl)c(Cl)c(Cl)c1 | ClC=1C=C(N)C=C(C1Cl)Cl.C(=O)(Cl)Cl>>ClC=1C=C(C=C(C1Cl)Cl)N=C=O | [NH2:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1.Cl[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1 | Nc1cc(Cl)c(Cl)c(Cl)c1.O=C(Cl)Cl | O=C=Nc1cc(Cl)c(Cl)c(Cl)c1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 7d3fae5ca5d4875eff5b8b9cc12bb45e992207dcc8962ac035cf5aaf63f27286 | 5e78fe62a292da2c55590df217f7e190c26df27095ff0827e6cc86b7659890bd | c1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A mixture of 3,4,5-trichloroaniline (400 mg; 2 mmol) in toluene (15 ml) and phosgene (6 ml 20% in toluene; 12 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4,5-trichlorophenylisocyanate. To the crude product was added 3-[4-(4-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Isocyanate | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | Nc1cc(Cl)c(Cl)c(Cl)c1.O=C(Cl)Cl>C1(=CC=CC=C1)C>O=C=Nc1cc(Cl)c(Cl)c(Cl)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-670859b83ec7444589c35a833a5ac749 | O=C=Nc1ccc2c(c1)OCCO2.OCCCN1CCN(c2ccc(Cl)cc2)CC1.OCCCN1CCN(c2cccc(C(F)(F)F)c2)CC1>>Cl.O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2cccc(C(F)(F)F)c2)CC1 | C1OC=2C=C(C=CC2OC1)N=C=O.FC(C=1C=C(C=CC1)N1CCN(CC1)CCCO)(F)F.ClC1=CC=C(C=C1)N1CCN(CC1)CCCO>>Cl.FC(C=1C=C(C=CC1)N1CCN(CC1)CCCOC(NC1=CC2=C(C=C1)OCCO2)=O)(F)F | [O:2]=[C:3]=[N:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][CH2:13][O:14]2.OCCCN1CCN(c2ccc([Cl:1])cc2)CC1.[OH:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([c:23]2[cH:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]2)[CH2:33][CH2:34]1>>[ClH:1].[O:2]=[C:3]([NH:4][c:5]1[cH:6][cH:7][c:8]2... | O=C=Nc1ccc2c(c1)OCCO2.OCCCN1CCN(c2ccc(Cl)cc2)CC1.OCCCN1CCN(c2cccc(C(F)(F)F)c2)CC1 | Cl.O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2cccc(C(F)(F)F)c2)CC1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 14e40dbdcc7f3e405d561bcd4b390447f33d4a6df07ad339178aa3ae453a15a7 | dc3986f665575f2e95903203ed4620c2854cf424dd52fda83b9b7c25e8dcb409 | O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2ccccc2)CC1 | O-C-C-C-N1-C-C-N(-c2:c:c:c(-[Cl;H0;D1;+0:1]):c:c:2)-C-C-1.[C:2]-[C:3]-[OH;D1;+0:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:2]-[C:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:6](=[O;D1;H0:5])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10].[ClH;D0;+0:1] | 68.7 | [{"value": 68.7, "product": "Cl.FC(C=1C=C(C=CC1)N1CCN(CC1)CCCOC(NC1=CC2=C(C=C1)OCCO2)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,4-ethylenedioxyphenylisocyanate (2.0 mmol) (produced as in Example 16) and 3-[4-(3-trifluoromethyl-phenyl) -1-piperazinyl]propanol (580 mg; 2.0 mmol) in toluene (30 ml) was refluxed for 16 h. To the crude product was added 3-[4-(4-chlorophenyl)-1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (30 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Isocyanate.Primary alcohol.Primary alcohol.Tertiary amine.Tertiary amine | Carbamic ester.Ether | C1CNCCN1.c1ccccc1 | null | c1ccc2c(c1)OCCO2.C1C[NH]CC[NH]1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | O=C=Nc1ccc2c(c1)OCCO2.OCCCN1CCN(c2ccc(Cl)cc2)CC1.OCCCN1CCN(c2cccc(C(F)(F)F)c2)CC1>C1(=CC=CC=C1)C>Cl.O=C(Nc1ccc2c(c1)OCCO2)OCCCN1CCN(c2cccc(C(F)(F)F)c2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-586d8f67d54a4ce2aae6db63cc9c2cee | COc1cc(N)cc(OC)c1OC.S=C(Cl)Cl>>COc1cc(N=C=S)cc(OC)c1OC | COC=1C=C(N)C=C(C1OC)OC.C(=S)(Cl)Cl.C(C)N(CC)CC>>COC=1C=C(C=C(C1OC)OC)N=C=S | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:9][c:10]([O:11][CH3:12])[c:13]1[O:14][CH3:15].Cl[C:7](Cl)=[S:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[C:7]=[S:8])[cH:9][c:10]([O:11][CH3:12])[c:13]1[O:14][CH3:15] | COc1cc(N)cc(OC)c1OC.S=C(Cl)Cl | COc1cc(N=C=S)cc(OC)c1OC | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[S;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A mixture of 3,4,5-trimethoxyaniline (440 mg; 2.4 mmol) in toluene (20 ml), thiophosgene (300 mg; 2.5 mmol) and triethylamine (500 mg; 5 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4,5-trimethoxyphenylisothiocyanate. To the crude product was added 3-[4-(4-chlorophenyl)-1-p... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | COc1cc(N)cc(OC)c1OC.S=C(Cl)Cl>C1(=CC=CC=C1)C>COc1cc(N=C=S)cc(OC)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-32f0e1a47d884b0fa22a2aeb54b8e2e5 | COc1cc(N=C=S)cc(OC)c1OC.OCCCN1CCN(c2cccc(Cl)c2)CC1>>COc1cc(NC(=S)OCCCN2CCN(c3cccc(Cl)c3)CC2)cc(OC)c1OC.Cl | COC=1C=C(C=C(C1OC)OC)N=C=S.ClC=1C=C(C=CC1)N1CCN(CC1)CCCO>>Cl.ClC=1C=C(C=CC1)N1CCN(CC1)CCCOC(NC1=CC(=C(C(=C1)OC)OC)OC)=S | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[C:7]=[S:8])[cH:26][c:27]([O:28][CH3:29])[c:30]1[O:31][CH3:32].[OH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[S:8])[O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:... | COc1cc(N=C=S)cc(OC)c1OC.OCCCN1CCN(c2cccc(Cl)c2)CC1 | COc1cc(NC(=S)OCCCN2CCN(c3cccc(Cl)c3)CC2)cc(OC)c1OC.Cl | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 9e3a8c0d56f92f6e18e85ce13463720e919a83cf12ea77e6edf57350a47349d7 | bbceef05bdacab86c2602bf4842762dab38cbf1667695a1e36921fb8a2501dd1 | S=C(Nc1ccccc1)OCCCN1CCN(c2ccccc2)CC1 | [C:1]-[C:2]-[OH;D1;+0:3].[S;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:5](=[S;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 38.7 | [{"value": 38.7, "product": "Cl.ClC=1C=C(C=CC1)N1CCN(CC1)CCCOC(NC1=CC(=C(C(=C1)OC)OC)OC)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,4,5-trimethoxyphenylisothiocyanate (2.0 mmol) (produced as in Example 22) and 3-[4-(3-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (40 ml) was refluxed for 16 h. The solvent was evaporated and the residue resuspended in ethyl acetate, filtered and evaporated to dryness. The residue... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Isothiocyanate | Ether.Thioamide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | COc1cc(N=C=S)cc(OC)c1OC.OCCCN1CCN(c2cccc(Cl)c2)CC1>C1(=CC=CC=C1)C>COc1cc(NC(=S)OCCCN2CCN(c3cccc(Cl)c3)CC2)cc(OC)c1OC.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7dae953e4f5249e8b8c29ff501f4aac0 | COc1cc(N=C=S)cc(OC)c1OC.OCCCN1CCN(c2ccccc2Cl)CC1>>COc1cc(NC(=S)OCCCN2CCN(c3ccccc3Cl)CC2)cc(OC)c1OC.Cl | COC=1C=C(C=C(C1OC)OC)N=C=S.ClC1=C(C=CC=C1)N1CCN(CC1)CCCO>>Cl.ClC1=C(C=CC=C1)N1CCN(CC1)CCCOC(NC1=CC(=C(C(=C1)OC)OC)OC)=S | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[C:7]=[S:8])[cH:26][c:27]([O:28][CH3:29])[c:30]1[O:31][CH3:32].[OH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[Cl:23])[CH2:24][CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[S:8])[O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14... | COc1cc(N=C=S)cc(OC)c1OC.OCCCN1CCN(c2ccccc2Cl)CC1 | COc1cc(NC(=S)OCCCN2CCN(c3ccccc3Cl)CC2)cc(OC)c1OC.Cl | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 9e3a8c0d56f92f6e18e85ce13463720e919a83cf12ea77e6edf57350a47349d7 | bbceef05bdacab86c2602bf4842762dab38cbf1667695a1e36921fb8a2501dd1 | S=C(Nc1ccccc1)OCCCN1CCN(c2ccccc2)CC1 | [C:1]-[C:2]-[OH;D1;+0:3].[S;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:5](=[S;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 42.6 | [{"value": 42.6, "product": "Cl.ClC1=C(C=CC=C1)N1CCN(CC1)CCCOC(NC1=CC(=C(C(=C1)OC)OC)OC)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,4,5-trimethoxyphenylisothiocyanate (2.0 mmol) (produced as in Example 22) and 3-[4-(2-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (40 ml) was refluxed for 16 h. The solvent was evaporated and the residue resuspended in ethyl acetate filtered and evaporated to dryness. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Isothiocyanate | Ether.Thioamide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | COc1cc(N=C=S)cc(OC)c1OC.OCCCN1CCN(c2ccccc2Cl)CC1>C1(=CC=CC=C1)C>COc1cc(NC(=S)OCCCN2CCN(c3ccccc3Cl)CC2)cc(OC)c1OC.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a2ccd79bcb014e29be695973b6182ff8 | Nc1cccc2c1CCCC2.O=C(Cl)Cl.OCCCN1CCN(c2cccc3ccccc23)CC1>>Cl.O=C(Nc1cccc2c1CCCC2)OCCCN1CCN(c2cccc3ccccc23)CC1 | C1(=CC=CC2=CC=CC=C12)N1CCN(CC1)CCCO.NC1=C2CCCCC2=CC=C1.C(=O)(Cl)Cl>>Cl.C1(=CC=CC2=CC=CC=C12)N1CCN(CC1)CCCOC(NC1=C2CCCCC2=CC=C1)=O | [NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:11][CH2:12][CH2:13][CH2:14]2.Cl[C:3]([Cl:1])=[O:2].[OH:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([c:23]2[cH:24][cH:25][cH:26][c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]23)[CH2:33][CH2:34]1>>[ClH:1].[O:2]=[C:3]([NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:... | Nc1cccc2c1CCCC2.O=C(Cl)Cl.OCCCN1CCN(c2cccc3ccccc23)CC1 | Cl.O=C(Nc1cccc2c1CCCC2)OCCCN1CCN(c2cccc3ccccc23)CC1 | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | b783741d830260fad8364d3094e4427c043c7a8c214759fe599aa3fdd16b13d3 | 9b7fceec1df32b8b20bdc842e740f77a3b0aef029c8756c8e5525720be8f722b | O=C(Nc1cccc2c1CCCC2)OCCCN1CCN(c2cccc3ccccc23)CC1 | Cl-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10].[ClH;D0;+0:2] | null | [] | null | null | null | null | A mixture of 5-amino-1,2,3,4-tetrahydronaphthalene (300 mg; 2.0 mmol) in toluene (10 ml) and phosgene (10 ml 20% in toluene) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 1,2,3,4-tetrahydronaphthyl -5-isocyanate. To the crude product was added 3-[4-(1-naphthyl)-1-piperazinyl]propano... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol.Primary amine | Carbamic ester.Ether | null | null | c1ccc2c(c1)CCCC2.C1C[NH]CC[NH]1.c1ccc2ccccc2c1 | HCl | C1(=CC=CC=C1)C | null | null | Nc1cccc2c1CCCC2.O=C(Cl)Cl.OCCCN1CCN(c2cccc3ccccc23)CC1>C1(=CC=CC=C1)C>Cl.O=C(Nc1cccc2c1CCCC2)OCCCN1CCN(c2cccc3ccccc23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b2cfaed8d84f496bad77a7ddcfae135c | S=C(NCCCN1CCN(c2ccccc2Cl)CC1)Nc1ccc2c(c1)OCCO2>>Clc1ccccc1N1CCN(CCCN=C=Nc2ccc3c(c2)OCCO3)CC1 | ClC1=C(C=CC=C1)N1CCN(CC1)CCCNC(=S)NC1=CC2=C(C=C1)OCCO2.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl.C(C)N(CC)CC>>ClC1=C(C=CC=C1)N1CCN(CC1)CCCN=C=NC1=CC2=C(C=C1)OCCO2 | S=[C:16]([NH:15][CH2:14][CH2:13][CH2:12][N:11]1[CH2:10][CH2:9][N:8]([c:7]2[c:2]([Cl:1])[cH:3][cH:4][cH:5][cH:6]2)[CH2:29][CH2:28]1)[NH:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][CH2:26][O:27]2>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][N:15]=[C:16]... | S=C(NCCCN1CCN(c2ccccc2Cl)CC1)Nc1ccc2c(c1)OCCO2 | Clc1ccccc1N1CCN(CCCN=C=Nc2ccc3c(c2)OCCO3)CC1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | a4a91ec0ddb252da701e1af18c11b69e2510ba110b4bfd3cbc7723dcd2543523 | 719172d7dce74dc79753aff677cdd65fea1bb26c8838af9ac8c4ee76a6ad639f | C(=NCCCN1CCN(c2ccccc2)CC1)=Nc1ccc2c(c1)OCCO2 | S=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[C:3]-[C:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[N;H0;D2;+0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 56.5 | [{"value": 56.5, "product": "ClC1=C(C=CC=C1)N1CCN(CC1)CCCN=C=NC1=CC2=C(C=C1)OCCO2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 400 | CELSIUS | null | null | A mixture of N-3-[4-(2-chlorophenyl)piperazin-1-yl]propyl-N '-(3,4-ethylenedioxyphenyl)thiourea of Example 11 (1.35 g; 3 mmol), triphenylphosphin (1.02 g; 3.9 mmol), carbon tetrachloride (0.56 ml), triethylamine (0.3 g; 3 mmol) and methylene chloride (15 ml) Was stirred at reflux for 3 h and at 400° C. for 16 h. The re... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | Other | C(Cl)Cl | 400 | null | S=C(NCCCN1CCN(c2ccccc2Cl)CC1)Nc1ccc2c(c1)OCCO2>C(Cl)Cl>Clc1ccccc1N1CCN(CCCN=C=Nc2ccc3c(c2)OCCO3)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-588df9429c01452987b98d1b2b5b1d86 | COC(=O)c1ccccc1C1=CCC(=CBr)C=C1.O=C1NC(=O)c2ccccc21>>COC(=O)c1ccccc1-c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | BrC=C1CC=C(C=C1)C1=C(C(=O)OC)C=CC=C1.C1(C=2C(C(N1)=O)=CC=CC2)=O.C([O-])([O-])=O.[K+].[K+]>>C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN2C(C=3C(C2=O)=CC=CC3)=O)C=C1 | Br[CH:15]=[C:14]1[CH2:13][CH:12]=[C:11]([c:10]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]2)[CH:28]=[CH:27]1.[NH:16]1[C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]1=[O:26]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([CH2:15][N:16]2[C:17](=[O:... | COC(=O)c1ccccc1C1=CCC(=CBr)C=C1.O=C1NC(=O)c2ccccc21 | COC(=O)c1ccccc1-c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 609c65585011bba8edeeb4bb600f1addeb9ff9e80e3dcf5c6b163713b3cd87c7 | 586b1fb4602ab2e0591901c5daa3d36e8641b4ff493f6c7458460ac161a45718 | O=C1c2ccccc2C(=O)N1Cc1ccc(-c2ccccc2)cc1 | Br-[CH;D2;+0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH;D2;+0:4]=[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13]):[c:14])-[CH;D2;+0:15]=[CH;D2;+0:16]-1.[O;D1;H0:17]=[C:18]1-[NH;D2;+0:19]-[C:20](=[O;D1;H0:21])-[c:22]:[c:23]-1>>[C;D1;H3:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[c:9](:[c:... | 71 | [{"value": 71.0, "product": "C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN2C(C=3C(C2=O)=CC=CC3)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 7.4, "product": "C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN2C(C=3C(C2=O)=CC=CC3)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 2-[4-(bromomethylene)phenyl]benzoate (1.22 g, 0.04 mole), phthalimide (0.59 g, 0.04 mole), and potassium carbonate (0.55 g, 0.04 mole) are combined in 120 mL acetonitrile. The mixture is heated at reflux for 24 hours. At that time the mixture is filtered through celite and rotovapped to a residue. The residue is... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide | Substituted dicarboximide | C1=CCCC=C1.c1ccc2c(c1)CNC2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HBr | C(C)#N | null | null | COC(=O)c1ccccc1C1=CCC(=CBr)C=C1.O=C1NC(=O)c2ccccc21>C(C)#N>COC(=O)c1ccccc1-c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-baca5479f4474cdbbe8a3aa3b0b1e8f4 | COC(=O)c1ccccc1-c1ccc(CN2C(=O)c3ccccc3C2=O)cc1>>COC(=O)c1ccccc1-c1ccc(CN)cc1 | C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN2C(C=3C(C2=O)=CC=CC3)=O)C=C1.O.NN>>C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN)C=C1 | O=C1c2ccccc2C(=O)[N:16]1[CH2:15][c:14]1[cH:13][cH:12][c:11](-[c:10]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]2)[cH:18][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([CH2:15][NH2:16])[cH:17][cH:18]1 | COC(=O)c1ccccc1-c1ccc(CN2C(=O)c3ccccc3C2=O)cc1 | COC(=O)c1ccccc1-c1ccc(CN)cc1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccc(-c2ccccc2)cc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[c:3])-C(=O)-c2:c:c:c:c:c:2-1>>[NH2;D1;+0:1]-[C:2]-[c:3] | 66.3 | [{"value": 66.0, "product": "C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound (f) of Example 6 (3.85 g, 0.01 mole) is dissolved in 100 mL of absolute ethanol with warming. Hydrazine hydrate (7.5 mL) is added at once. The solution is heated to reflux for 10 minutes and the reaction mixture sets up. The mixture is cooled to room temperature and filtered. The precipitate is washed with exc... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | COC(=O)c1ccccc1-c1ccc(CN2C(=O)c3ccccc3C2=O)cc1>C(C)O>COC(=O)c1ccccc1-c1ccc(CN)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ca5895282f2f46f58e9c9d3bbfc13aa0 | CCOC(=O)/C=C1\CC(C)(C)CC(=O)O1.COC(=O)c1ccccc1-c1ccc(CN)cc1>>CCOC(=O)C=C1CC(C)(C)CC(=O)N1Cc1ccc(-c2ccccc2C(=O)OC)cc1 | C(=O)(OC)C1=C(C=CC=C1)C1=CC=C(CN)C=C1.C(=O)(OCC)\C=C\1/CC(CC(=O)O1)(C)C>>C(=O)(OCC)C=C1CC(CC(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C(=O)OC)=O)(C)C | O1/[C:7](=[CH:6]/[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8][C:9]([CH3:10])([CH3:11])[CH2:12][C:13]1=[O:14].[NH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[C:27](=[O:28])[O:29][CH3:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[CH2:8][C:9]([CH3:10])([CH3:11])[CH2... | CCOC(=O)/C=C1\CC(C)(C)CC(=O)O1.COC(=O)c1ccccc1-c1ccc(CN)cc1 | CCOC(=O)C=C1CC(C)(C)CC(=O)N1Cc1ccc(-c2ccccc2C(=O)OC)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 70408d5fde858028c994ed2ff80728474f38bf697e4474de632b86f29f1f4567 | e0ec867931bf96e41aac6c444216606387f6ec05ea14f545a573ebf8fbfca418 | [CH]=C1CCCC(=O)N1Cc1ccc(-c2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[C:5]=[C;H0;D3;+0:6]1/O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[C:10]-[C:11]-1.[NH2;D1;+0:12]-[C:13]-[c:14]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]=[C;H0;D3;+0:6]1-[C:11]-[C:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[N;H0;D3;+0:12]-1-[C:13]-[c:14] | 52 | [{"value": 52.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound (i) of Example 9 (1.2 g, 0.005 mole) and compound (b) of Example 2 (1.1 g, 0.005 mole) are combined in toluene (50 mL) and refluxed for 5 hours. The toluene is removed in vacuo and the residue is chromatographed on silica gel using hexane/ethyl acetate as the mobile phase. The title compound is isolated as a c... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Enamine.Tertiary amide | C1CCOCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)/C=C1\CC(C)(C)CC(=O)O1.COC(=O)c1ccccc1-c1ccc(CN)cc1>C1(=CC=CC=C1)C>CCOC(=O)C=C1CC(C)(C)CC(=O)N1Cc1ccc(-c2ccccc2C(=O)OC)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8e2b8999ef46448dbc47fb9f17a42212 | COC(=O)c1ccccc1Cc1ccc(CN)cc1>>NCc1ccc(Cc2ccccc2C(=O)O)cc1 | NCC1=CC=C(CC2=C(C(=O)OC)C=CC=C2)C=C1.[OH-].[K+]>>NCC1=CC=C(CC2=C(C(=O)O)C=CC=C2)C=C1 | C[O:16][C:14]([c:13]1[c:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([CH2:2][NH2:1])[cH:18][cH:17]2)[cH:9][cH:10][cH:11][cH:12]1)=[O:15]>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[OH:16])[cH:17][cH:18]1 | COC(=O)c1ccccc1Cc1ccc(CN)cc1 | NCc1ccc(Cc2ccccc2C(=O)O)cc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 57 | [{"value": 57.0, "product": "NCC1=CC=C(CC2=C(C(=O)O)C=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.9, "product": "NCC1=CC=C(CC2=C(C(=O)O)C=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 2-(4-aminomethylbenzyl)benzoate (2.41 g, 0.01 moles) is dissolved in 50 mL methanol and 10 mL of 50% KOH is added. The mixture is heated at reflux for 6 hours, concentrated in vacuo and then acidified to yield 1.3 g (57%) of title compound as a precipitate. Mass Spec (DCI) m/z 228. Further purification is achiev... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | COC(=O)c1ccccc1Cc1ccc(CN)cc1>CO>NCc1ccc(Cc2ccccc2C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4434c0d771104b01912a94f6390283bd | CC1(C)OCC(CCn2cnc3c(Cl)nc(N)nc32)CO1>>Nc1ncc2ncn(CCC(CO)CO)c2n1 | NC1=NC(=C2N=CN(C2=N1)CCC1COC(OC1)(C)C)Cl>>NC1=NC=C2N=CN(C2=N1)CCC(CO)CO | CC1(C)[O:13][CH2:12][CH:11]([CH2:10][CH2:9][n:8]2[cH:7][n:6][c:5]3[c:4](Cl)[n:3][c:2]([NH2:1])[n:17][c:16]32)[CH2:14][O:15]1>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[n:6][cH:7][n:8]([CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:14][OH:15])[c:16]2[n:17]1 | CC1(C)OCC(CCn2cnc3c(Cl)nc(N)nc32)CO1 | Nc1ncc2ncn(CCC(CO)CO)c2n1 | null | [Pd] | C(C)O.C1=CCCCC1 | Deprotection | OtherReaction | 980d6aad4d67c4abf1215d73a95474a51dde5b93ebcfcc503c26fe868096b62b | 1a3bb0546a22efecbae8fec347b09f937434c77e5bca6020ba4a77234fd4719c | c1ncc2nc[nH]c2n1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]-[O;H0;D2;+0:5]-1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C:12]):[c:13]:[#7;a:14]:[c:15]:2:1>>[C:12]-[#7;a:11]1:[c:13]:[#7;a:14]:[c:15]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1:2.[OH;D1;+0:1]-[C:2]-[C:3]-[C:4]-[OH;D1;+0:5] | 36.1 | [{"value": 36.0, "product": "NC1=NC=C2N=CN(C2=N1)CCC(CO)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.1, "product": "NC1=NC=C2N=CN(C2=N1)CCC(CO)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.54 g, 1.75 mmol) in ethanol (10 ml) and cyclohexene (20 ml) was added 10% palladium-on-charcoal (400 mg) and the solution was refluxed for 7 hours. A further quantity of catalyst (200 mg) was added and the solution was refluxed overnig... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Primary alcohol.Primary alcohol | C1COCOC1.c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | [Pd].C(C)O.C1=CCCCC1 | null | 0.5 | CC1(C)OCC(CCn2cnc3c(Cl)nc(N)nc32)CO1>[Pd].C(C)O.C1=CCCCC1>Nc1ncc2ncn(CCC(CO)CO)c2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4433a99e49994b5fbc65a69fbcc99e86 | CC(=O)OCC(CCn1cnc2c(Cl)nc(N)nc21)COC(C)=O>>CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O | C(C)(=O)OCC(CCN1C2=NC(=NC(=C2N=C1)Cl)N)COC(C)=O.C(=O)[O-].[NH4+]>>C(C)(=O)OCC(CCN1C2=NC(=NC=C2N=C1)N)COC(C)=O | Cl[c:13]1[c:12]2[n:11][cH:10][n:9]([CH2:8][CH2:7][CH:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[CH2:19][O:20][C:21]([CH3:22])=[O:23])[c:18]2[n:17][c:15]([NH2:16])[n:14]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH:6]([CH2:7][CH2:8][n:9]1[cH:10][n:11][c:12]2[cH:13][n:14][c:15]([NH2:16])[n:17][c:18]12)[CH2:19][O:20][C:21]([CH3:22])=[... | CC(=O)OCC(CCn1cnc2c(Cl)nc(N)nc21)COC(C)=O | CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O | null | [Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | b8840c48c27b46eba2492ff13644ff7b692d81a67866146e2462bf32af623c46 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ncc2nc[nH]c2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6]2:[#7;a:7](-[C:8]):[c:9]:[#7;a:10]:[c:11]:2:1>>[C:8]-[#7;a:7]1:[c:9]:[#7;a:10]:[c:11]2:[cH;D2;+0:1]:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6]:1:2 | 90.2 | [{"value": 90.0, "product": "C(C)(=O)OCC(CCN1C2=NC(=NC=C2N=C1)N)COC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.2, "product": "C(C)(=O)OCC(CCN1C2=NC(=NC=C2N=C1)N)COC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (0.36 g, 1.0 mmol) and 10% palladium-on-charcoal (30 mg) in methanol containing ammonium formate (400 mM, 10 ml) was heated under reflux for 30 minutes. The mixture was allowed to cool, filtered and the solvent removed. The residue was taken u... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | Other | [Pd].CO | null | null | CC(=O)OCC(CCn1cnc2c(Cl)nc(N)nc21)COC(C)=O>[Pd].CO>CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9a26110b23a143e0bf216102d09220cd | CC(=O)OCC(CCn1cnc2c(Cl)nc(N)nc21)COC(C)=O>>Nc1ncc2ncn(CCC(CO)CO)c2n1 | C(C)(=O)OCC(CCN1C2=NC(=NC(=C2N=C1)Cl)N)COC(C)=O.C(=O)[O-].[NH4+]>>NC1=NC=C2N=CN(C2=N1)CCC(CO)CO | CC(=O)[O:13][CH2:12][CH:11]([CH2:10][CH2:9][n:8]1[cH:7][n:6][c:5]2[c:4](Cl)[n:3][c:2]([NH2:1])[n:17][c:16]21)[CH2:14][O:15]C(C)=O>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[n:6][cH:7][n:8]([CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:14][OH:15])[c:16]2[n:17]1 | CC(=O)OCC(CCn1cnc2c(Cl)nc(N)nc21)COC(C)=O | Nc1ncc2ncn(CCC(CO)CO)c2n1 | null | [Pd] | CO | Reduction | OtherReaction | 5676e2d2632a840028dd38efd72ba0f0c7e46f4be94c627e3b5e290aac466267 | 52ebef627106101206c69ca515c0ac99081a3c425ce4b96289419a6c0097d649 | c1ncc2nc[nH]c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]-[O;H0;D2;+0:5]-C(-C)=O.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C:12]):[c:13]:[#7;a:14]:[c:15]:2:1>>[C:12]-[#7;a:11]1:[c:13]:[#7;a:14]:[c:15]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1:2.[OH;D1;+0:1]-[C:2]-[C:3]-[C:4]-[OH;D1;+0:5] | null | [] | null | null | 20 | HOUR | To a suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (4.86 g, 13.7 mmol) in methanol (140 ml) containing ammonium formate (400 mM) was added 10% palladium-on-charcoal (0.4 g) and the mixture was heated under reflux for 40 minutes. After cooling the solution was filtered and the solvent remove... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Primary alcohol.Primary alcohol | c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | [Pd].CO | null | 20 | CC(=O)OCC(CCn1cnc2c(Cl)nc(N)nc21)COC(C)=O>[Pd].CO>Nc1ncc2ncn(CCC(CO)CO)c2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-46661896143e47e7a8d7bd3da3304edb | CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O>>CC(=O)OCC(CO)CCn1cnc2cnc(N)nc21 | C(C)(=O)OCC(CCN1C2=NC(=NC=C2N=C1)N)COC(C)=O.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)OCC(CCN1C2=NC(=NC=C2N=C1)N)CO | CC(=O)[O:8][CH2:7][CH:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[CH2:9][CH2:10][n:11]1[cH:12][n:13][c:14]2[cH:15][n:16][c:17]([NH2:18])[n:19][c:20]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH:6]([CH2:7][OH:8])[CH2:9][CH2:10][n:11]1[cH:12][n:13][c:14]2[cH:15][n:16][c:17]([NH2:18])[n:19][c:20]12 | CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O | CC(=O)OCC(CO)CCn1cnc2cnc(N)nc21 | null | C(C)(=O)O | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ncc2nc[nH]c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 30 | [{"value": 30.0, "product": "C(C)(=O)OCC(CCN1C2=NC(=NC=C2N=C1)N)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.6, "product": "C(C)(=O)OCC(CCN1C2=NC(=NC=C2N=C1)N)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine (0.48 g, 1.5 mmol) in methanol (9 ml) was added anhydrous potassium carbonate (14 mg, 0.1 mmol) and the solution was stirred for 20 minutes. Two drops of glacial acetic acid were added, the solution was filtered and the solvent was removed. The residu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ncc2nc[nH]c2n1 | HO- | C(C)(=O)O.CO | null | 0.333333 | CC(=O)OCC(CCn1cnc2cnc(N)nc21)COC(C)=O>C(C)(=O)O.CO>CC(=O)OCC(CO)CCn1cnc2cnc(N)nc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d85e608d23ee4bf4b2252ac1137409a6 | COC(C)(C)OC.Nc1ncc2ncn(CCC(CO)CO)c2n1>>CC1(C)OCC(CCn2cnc3cnc(N)nc32)CO1 | C([O-])([O-])=O.[K+].[K+].NC1=NC=C2N=CN(C2=N1)CCC(CO)CO.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.COC(C)(C)OC>>NC1=NC=C2N=CN(C2=N1)CCC1COC(OC1)(C)C | CO[C:2](OC)([CH3:1])[CH3:3].[OH:4][CH2:5][CH:6]([CH2:7][CH2:8][n:9]1[cH:10][n:11][c:12]2[cH:13][n:14][c:15]([NH2:16])[n:17][c:18]12)[CH2:19][OH:20]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][CH2:8][n:9]2[cH:10][n:11][c:12]3[cH:13][n:14][c:15]([NH2:16])[n:17][c:18]23)[CH2:19][O:20]1 | COC(C)(C)OC.Nc1ncc2ncn(CCC(CO)CO)c2n1 | CC1(C)OCC(CCn2cnc3cnc(N)nc32)CO1 | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 62ddc1c8876dc9a7cbb60a878850947e7724fb977f7222fd3b0f0d31de1c7e3e | 6b6226fd4badcea670aa5820a1aae85cfc6d5c23434c7397ad80cf7d3cd2d289 | c1ncc2ncn(CCC3COCOC3)c2n1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[OH;D1;+0:4]-[C:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[O;H0;D2;+0:4]-[C:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-1 | 94.5 | [{"value": 94.0, "product": "NC1=NC=C2N=CN(C2=N1)CCC1COC(OC1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "NC1=NC=C2N=CN(C2=N1)CCC1COC(OC1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (240 mg, 1.0 mmol) in N,N-dimethylformamide (3 ml) were added p-toluenesulphonic acid monohydrate (210 mg, 1.1 mmol) and 2,2-dimethoxypropane (0.62 ml, 5.0 mmol) and the solution was stirred for 30 minutes. Potassium carbonate (110 mg, 0.8 mmol) was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C=O)C.O | null | 0.5 | COC(C)(C)OC.Nc1ncc2ncn(CCC(CO)CO)c2n1>CN(C=O)C.O>CC1(C)OCC(CCn2cnc3cnc(N)nc32)CO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4d1fd178952846efa63a1421db1f7aea | CCCC(=O)OC(=O)CCC.COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)C(OC)OC(c3ccccc3)(c3ccccc3)c3ccccc3)c2n1>>CCCC(=O)OCC(CO)CCn1cnc2cnc(N)nc21 | OCC(CCN1C2=NC(=NC=C2N=C1NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)OC)C(OC)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)(=O)OC(CCC)=O.CN(C=O)C.CO>>NC1=NC=C2N=CN(C2=N1)CCC(COC(CCC)=O)CO | CCCC(=O)O[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].CO[CH:7]([O:6]C(c1ccccc1)(c1ccccc1)c1ccccc1)[CH:8]([CH2:9][OH:10])[CH2:11][CH2:12][n:13]1[c:14]([NH:20]C(c2ccccc2)(c2ccccc2)c2ccccc2)[n:15][c:16]2[cH:17][n:18][c:19](OC)[n:21][c:22]12>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:11][CH2:12][n:13]1... | CCCC(=O)OC(=O)CCC.COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)C(OC)OC(c3ccccc3)(c3ccccc3)c3ccccc3)c2n1 | CCCC(=O)OCC(CO)CCn1cnc2cnc(N)nc21 | null | CN(C1=CC=NC=C1)C | null | Protection | OtherReaction | 2ecc0cde4b84fb06820bcee91b1754c851e926249b6e7a58653fcaf3e8c3fad6 | 6c221013a3e7c85979be7de8e3ec254df274bb2409d0502462c409e9b0625ea3 | c1ncc2nc[nH]c2n1 | C-C-C-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].C-O-[CH;D3;+0:5](-[O;H0;D2;+0:6]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[C:7](-[C:8])-[C:9]-[C:10]-[#7;a:11]1:[c:12]2:[#7;a:13]:[c;H0;D3;+0:14](-O-C):[#7;a:15]:[c:16]:[c:17]:2:[#7;a:18]:[c;H0;D3;+0:19]:1-[NH;D2;+0:20]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1... | null | [] | null | null | 15 | MINUTE | To a solution of 9-(3-hydroxymethyl-4-monomethoxytrityloxybut-1-yl)-2-monomethoxytritylaminopurine (0.70 g, 0.9 mmol) and 4-dimethylaminopyridine (10 mg) in N,N-dimethylformamide (5 ml) was added butyric anhydride (0.29 ml, 1.8 mmol) and the solution was stirred for 15 minutes. Methanol (1 ml) was added and the solvent... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ether.Ether.Ether.Secondary amine | Ester.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HO- | CN(C1=CC=NC=C1)C | null | 0.25 | CCCC(=O)OC(=O)CCC.COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)C(OC)OC(c3ccccc3)(c3ccccc3)c3ccccc3)c2n1>CN(C1=CC=NC=C1)C>CCCC(=O)OCC(CO)CCn1cnc2cnc(N)nc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-764528aa38624dcfa5184438e1f2dcaa | COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)C(OC)OC(c3ccccc3)(c3ccccc3)c3ccccc3)c2n1.O=C(OC(=O)c1ccccc1)c1ccccc1>>Nc1ncc2ncn(CCC(CO)COC(=O)c3ccccc3)c2n1 | OCC(CCN1C2=NC(=NC=C2N=C1NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)OC)C(OC)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)=O.CN(C=O)C.CO>>NC1=NC=C2N=CN(C2=N1)CCC(COC(C1=CC=CC=C1)=O)CO | CO[c:2]1[n:3][cH:4][c:5]2[n:6][c:7]([NH:1]C(c3ccccc3)(c3ccccc3)c3ccccc3)[n:8]([CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH:14](OC)[O:15]C(c3ccccc3)(c3ccccc3)c3ccccc3)[c:24]2[n:25]1.O=C(O[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)c1ccccc1>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[n:6][cH:7][n:8]([CH2:9][CH2:10][CH:1... | COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)C(OC)OC(c3ccccc3)(c3ccccc3)c3ccccc3)c2n1.O=C(OC(=O)c1ccccc1)c1ccccc1 | Nc1ncc2ncn(CCC(CO)COC(=O)c3ccccc3)c2n1 | null | CN(C1=CC=NC=C1)C | null | Acylation | OtherReaction | 8dc71da2f3278c3a546ebef2f355759ace221476522cab6df184d42554ad3b2e | 2bcd672628837bb5ff05fc91f5aa797feff7881881652e9547a1a941e377f0cb | O=C(OCCCCn1cnc2cncnc21)c1ccccc1 | C-O-[CH;D3;+0:1](-[O;H0;D2;+0:2]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[C:3](-[C:4])-[C:5]-[C:6]-[#7;a:7]1:[c:8]2:[#7;a:9]:[c;H0;D3;+0:10](-O-C):[#7;a:11]:[c:12]:[c:13]:2:[#7;a:14]:[c;H0;D3;+0:15]:1-[NH;D2;+0:16]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=C(-O-[C;H0;D3;+0:17](=[O;D1;H0:18])-[c:1... | null | [] | null | null | 1 | HOUR | To a solution of 9-(3-hydroxymethyl-4-monomethoxytrityloxybut-1-yl)-2-monomethoxytritylaminopurine (0.70 g, 0.9 mmol) and 4-dimethylaminopyridine (10 mg) in N,N-dimethylformamide (5 ml) was added benzoic anhydride (0.61 g, 2.7 mmol) and the solution was stirred for 1 hour. Methanol (1 ml) was added and the solvent was ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Ether.Ether.Ether.Secondary amine | Ester.Primary amine | c1ncc2[nH]cnc2n1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C | null | 1 | COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)C(OC)OC(c3ccccc3)(c3ccccc3)c3ccccc3)c2n1.O=C(OC(=O)c1ccccc1)c1ccccc1>CN(C1=CC=NC=C1)C>Nc1ncc2ncn(CCC(CO)COC(=O)c3ccccc3)c2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1f2cecd09ef940538b1511536d172b39 | COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)CO)c2n1>>Nc1ncc2ncn(CCC(CO)CO)c2n1 | C([O-])(O)=O.[Na+].OCC(CCN1C2=NC(=NC=C2N=C1NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)OC)CO.N1=CC=CC=C1.P(=O)(Cl)(Cl)Cl.N1=CC=CC=C1>>NC1=NC=C2N=CN(C2=N1)CCC(CO)CO | CO[c:2]1[n:3][cH:4][c:5]2[n:6][c:7]([NH:1]C(c3ccccc3)(c3ccccc3)c3ccccc3)[n:8]([CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:14][OH:15])[c:16]2[n:17]1>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[n:6][cH:7][n:8]([CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:14][OH:15])[c:16]2[n:17]1 | COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)CO)c2n1 | Nc1ncc2ncn(CCC(CO)CO)c2n1 | null | null | O | Miscellaneous | OtherReaction | e5babd6690e501689ab5ad2cd9858825b0107d13f0939f17e2eb47ce28671be1 | 5f7e3a2751f78ce426af726cda9b4389caf68c3da002c8cfc8dba6321522961e | c1ncc2nc[nH]c2n1 | C-O-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c;H0;D3;+0:6](-[NH;D2;+0:7]-C(-c3:c:c:c:c:c:3)(-c3:c:c:c:c:c:3)-c3:c:c:c:c:c:3):[#7;a:8]:[c:9]:2:[c:10]:[#7;a:11]:1>>[C:5]-[#7;a:4]1:[cH;D2;+0:6]:[#7;a:8]:[c:9]2:[c:10]:[#7;a:11]:[c;H0;D3;+0:1](-[NH2;D1;+0:7]):[#7;a:2]:[c:3]:1:2 | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To an ice-cooled solution of phosphorus oxychloride (93 μl, 1.0 mmol) in pyridine (2 ml) was added dropwise over 45 minutes a solution of 9-(4-hydroxy-3-hydroxymethylbut-1-yl)-2-monomethoxytritylaminopurine (0.46 g, 0.9 mmol) in pyridine (4 ml). The solution was stirred for a further 20 minutes at room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary amine | c1ncc2[nH]cnc2n1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | O | null | 0.333333 | COc1ncc2nc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n(CCC(CO)CO)c2n1>O>Nc1ncc2ncn(CCC(CO)CO)c2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6a23c604727f4daa90504cc1726ca6c2 | CC(O)C1CCCCN1C.Cc1cccc2[nH]nc(C(=O)Cl)c12>>CC(OC(=O)c1nn(C)c2ccccc12)C1CCCCN1C | CC1=C2C(=NNC2=CC=C1)C(=O)Cl.CCCCCC.[Li]CCCC.CN1C(CCCC1)C(C)O>>CN1N=C(C2=CC=CC=C12)C(=O)OC(C)C1N(CCCC1)C | [CH3:1][CH:2]([OH:3])[CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH3:22].Cl[C:4](=[O:5])[c:6]1[n:7][nH:8][c:10]2[cH:11][cH:12][cH:13][c:14]([CH3:9])[c:15]12>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[c:6]1[n:7][n:8]([CH3:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12)[CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH3:22] | CC(O)C1CCCCN1C.Cc1cccc2[nH]nc(C(=O)Cl)c12 | CC(OC(=O)c1nn(C)c2ccccc12)C1CCCCN1C | null | null | CN1C(N(CC1)C)=O.C1CCOC1 | Acylation | OtherReaction | 44977f9d0cad426aa0f0b3ae03f1de0acef5bec73ce72bd6b1995a657e74e715 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(OCC1CCCCN1)c1n[nH]c2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[nH;D2;+0:5]:[c:6]2:[c:7]:[c:8]:[c:9]:[c;H0;D3;+0:10](-[CH3;D1;+0:11]):[c:12]:2:1.[#7:13]-[C:14]-[C:15](-[C;D1;H3:16])-[OH;D1;+0:17]>>[#7:13]-[C:14]-[C:15](-[C;D1;H3:16])-[O;H0;D2;+0:17]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[n;H0;D3;+0:5](-[CH3;D1;+0:11]):[c:6]2:[... | null | [] | null | null | 20 | MINUTE | (1-Methyl-2-piperidyl)-1-ethanol (4.5 g, 31 mmol) was dissolved in dry THF (70 ml) and 1,3-dimethyl-2-imidazolidinone (20 ml) was added. The solution was ice-cooled and a hexane solution of n-BuLi (1.6M, 20 ml) was added dropwise. The reaction solution was stirred at room temperature for 20 minutes, to which was added ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | c1ccc2n[nH]cc2c1 | c1[nH]nc2ccccc12 | c1[nH]nc2ccccc12.C1CC[NH]CC1 | HCl | CN1C(N(CC1)C)=O.C1CCOC1 | null | 0.333333 | CC(O)C1CCCCN1C.Cc1cccc2[nH]nc(C(=O)Cl)c12>CN1C(N(CC1)C)=O.C1CCOC1>CC(OC(=O)c1nn(C)c2ccccc12)C1CCCCN1C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e45f94245eb45bca513a2ee7f3e24bf | CO.O=C(O)c1cc(Cl)ccc1O>>COC(=O)c1cc(Cl)ccc1O | S(=O)(Cl)Cl.ClC1=CC=C(C(C(=O)O)=C1)O.CO>>ClC1=CC=C(C(C(=O)OC)=C1)O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[OH:12] | CO.O=C(O)c1cc(Cl)ccc1O | COC(=O)c1cc(Cl)ccc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a cold solution of 100 ml methanol is slowly added 100 ml thionyl chloride followed by 30 g of 5-chlorosalicylic acid. This is then refluxed overnight, the solvent removed and the residue dissolved in ether. The ether is washed with a sodium bicarbonate solution, water, dried over magnesium sulfate and evaporated to... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)c1cc(Cl)ccc1O>>COC(=O)c1cc(Cl)ccc1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e0690a28b3d54980b51fc455d392fbaf | BrC1C=CCCC1.COC(=O)c1cc(Cl)ccc1O>>COC(=O)c1cc(Cl)ccc1OC1C=CCCC1 | O.ClC1=CC=C(C(C(=O)OC)=C1)O.C(=O)([O-])[O-].[K+].[K+].BrC1C=CCCC1>>C1=CC(CCC1)OC1=C(C(=O)OC)C=C(C=C1)Cl | Br[CH:13]1[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[O:12][CH:13]1[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18]1 | BrC1C=CCCC1.COC(=O)c1cc(Cl)ccc1O | COC(=O)c1cc(Cl)ccc1OC1C=CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e1c2ba5bf315aa3a75d052772391f024f194eaaea55bd1eb939cbe307ec8316d | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | C1=CC(Oc2ccccc2)CCC1 | Br-[CH;D3;+0:1]1-[C:2]=[C:3]-[C:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]=[C:3]-[C:4]-[C:5]-[C:6]-1):[c:13] | null | [] | 90 | CELSIUS | 8 | HOUR | A mixture of 18.6 g of methyl 5-chlorosalicylate, 28 g of K2CO3 and 20 g of 3-bromocyclohexene in 200 ml of DMF is stirred at 90° C. overnight. The mixture is then Poured into water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate and evaporated to dryness to obtain crude product. This is ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1=CCCCC1 | C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | HBr | CN(C)C=O | 90 | 8 | BrC1C=CCCC1.COC(=O)c1cc(Cl)ccc1O>CN(C)C=O>COC(=O)c1cc(Cl)ccc1OC1C=CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4563d094e20d4ff7b79cc94364998fa9 | COC(=O)c1cc(Cl)cc2c1OC1CCCCC21>>O=C(O)c1cc(Cl)cc2c1OC1CCCCC21 | ClC1=CC2=C(OC3C2CCCC3)C(=C1)C(=O)OC>>ClC1=CC2=C(OC3C2CCCC3)C(=C1)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]21>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]21 | COC(=O)c1cc(Cl)cc2c1OC1CCCCC21 | O=C(O)c1cc(Cl)cc2c1OC1CCCCC21 | null | null | [OH-].[Na+].CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)OC1CCCCC21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 50 | CELSIUS | 6 | HOUR | A mixture of 1.6 g of methyl 2-chloro-5a,6,7, 8,9,9a-hexahydrodibenzofuran-4-carboxylate in 10 ml of methanol and 20 ml of 1N sodium hydroxide is stirred at 50° C. for 6 hours. This is cooled, the methanol is removed under vacuo, diluted with 30 ml water and filtered. The aqueous solution is acidified with acetic acid,... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)OC1CCCCC21 | Other | [OH-].[Na+].CO | 50 | 6 | COC(=O)c1cc(Cl)cc2c1OC1CCCCC21>[OH-].[Na+].CO>O=C(O)c1cc(Cl)cc2c1OC1CCCCC21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1eb26c95049e45f5a0d34f4298931c2b | CO.COc1cc(N)c(Cl)cc1C(=O)O>>COC(=O)c1cc(Cl)c(N)cc1OC | COC1=C(C(=O)O)C=C(C(=C1)N)Cl.Cl.CO>>COC1=C(C(=O)OC)C=C(C(=C1)N)Cl | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH2:10])[cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH2:10])[cH:11][c:12]1[O:13][CH3:14] | CO.COc1cc(N)c(Cl)cc1C(=O)O | COC(=O)c1cc(Cl)c(N)cc1OC | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | To a solution of 50g of 2-methoxy-4-amino-5-chlorobenzoic acid in 500 ml of methanol is added HCl gas until all the material dissolves. Stirring is continued overnight, the solvent removed, ether added, filtered, dried over magnesium sulfate and evaporated to dryness to obtain methyl 2-methoxy-4-amino-5-chlorobenzoate ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | 8 | CO.COc1cc(N)c(Cl)cc1C(=O)O>>COC(=O)c1cc(Cl)c(N)cc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-43ac3093e75347328275d77d7718f91d | CC(=O)O.COC(=O)c1cc(Cl)c(N)cc1OC>>COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC | COC1=C(C(=O)OC)C=C(C(=C1)N)Cl.C(C)(=O)O>>COC1=C(C(=O)OC)C=C(C(=C1)NC(C)=O)Cl | O[C:11]([CH3:12])=[O:13].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH2:10])[cH:14][c:15]1[O:16][CH3:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]1[O:16][CH3:17] | CC(=O)O.COC(=O)c1cc(Cl)c(N)cc1OC | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC | null | null | C(C)(=O)OC(C)=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of 21 g of methyl 2-methoxy-4-amino-5-chlorobenzoate is stirred in 12 ml acetic anhydride and 100 ml acetic acid at 100° C. for 24 hours. The reaction mixture is filtered, diluted with water, filtered and evaporated to dryness to obtain methyl 2-methoxy-4-acetylamino-5-chlorobenzoate which is used directly in... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(C)(=O)OC(C)=O | null | null | CC(=O)O.COC(=O)c1cc(Cl)c(N)cc1OC>C(C)(=O)OC(C)=O>COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-75cffe8369b94e409740b23e60a89348 | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC>>CC(=O)Nc1cc(O)c(C(=O)O)cc1Cl | COC1=C(C(=O)OC)C=C(C(=C1)NC(C)=O)Cl.B(Br)(Br)Br.[OH-].[Na+]>>C(C)(=O)NC=1C=C(C(C(=O)O)=CC1Cl)O | C[O:8][c:7]1[cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[c:14]([Cl:15])[cH:13][c:9]1[C:10](=[O:11])[O:12]C>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([OH:8])[c:9]([C:10](=[O:11])[OH:12])[cH:13][c:14]1[Cl:15] | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC | CC(=O)Nc1cc(O)c(C(=O)O)cc1Cl | null | null | C(Cl)Cl | Deprotection | OtherReaction | 4cea9c1cf4071f9c3a5e0d042ee7e87c9888ee05636b0c5b9dfd162b490d7fb6 | 707aece9d1d6de1fa508344f68d9f46b61d18785c603f5e19232e661c94aa284 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[O;H0;D2;+0:6]-C):[c:7]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7] | null | [] | null | null | 24 | HOUR | To a mixture of 16 g of methyl 2-methoxy-4-acetylamino-5-chlorobenzoate in 130 ml of methylene chloride is slowly added 100 ml of a methylene chloride solution of borontribromide (250 g BBr3 per liter) and stirring continued for 24 hours. 1N sodium hydroxide solution is then added until all material is dissolved. The t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 24 | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC>C(Cl)Cl>CC(=O)Nc1cc(O)c(C(=O)O)cc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a899c80f18084f9c9768df737127ddcc | BrC1C=CCCC1.COC(=O)c1cc(Cl)c(NC(C)=O)cc1O>>COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC1C=CCCC1 | C(C)(=O)NC=1C=C(C(C(=O)OC)=CC1Cl)O.BrC1C=CCCC1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>C1=CC(CCC1)OC1=C(C(=O)OC)C=C(C(=C1)NC(C)=O)Cl | Br[CH:17]1[CH:18]=[CH:19][CH2:20][CH2:21][CH2:22]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]1[OH:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]1[O:16][CH:17]1[CH:18]=[CH:19][CH2:20][CH2:21][CH2:22]1 | BrC1C=CCCC1.COC(=O)c1cc(Cl)c(NC(C)=O)cc1O | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC1C=CCCC1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e1c2ba5bf315aa3a75d052772391f024f194eaaea55bd1eb939cbe307ec8316d | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | C1=CC(Oc2ccccc2)CCC1 | Br-[CH;D3;+0:1]1-[C:2]=[C:3]-[C:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]=[C:3]-[C:4]-[C:5]-[C:6]-1):[c:13] | null | [] | 110 | CELSIUS | null | null | A mixture of 2.5 g methyl 4-acetylamino-5chlorosalicylate, 2 g of 3-bromocyclohexene, 2 g K2CO3 and 30 ml DMF are combined and heated at 110° C. overnight. The reaction mixture is then poured into water, filtered, dried and then extracted into ether. The ether solution is treated with charcoal, filtered and evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1=CCCCC1 | C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | HBr | O | 110 | null | BrC1C=CCCC1.COC(=O)c1cc(Cl)c(NC(C)=O)cc1O>O>COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC1C=CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-30b84fcc575343ca86cb76a38a32799d | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC1C=CCCC1>>COC(=O)c1cc(Cl)c(NC(C)=O)c(C2CC=CCC2)c1O | C1=CC(CCC1)OC1=C(C(=O)OC)C=C(C(=C1)NC(C)=O)Cl>>C1(CC=CCC1)C1=C(C(C(=O)OC)=CC(=C1NC(C)=O)Cl)O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:21]1[O:22][CH:15]1[CH:16]=[CH:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[c:14]([CH:15]2[CH2:16][CH:17]=[CH:18][CH2:19][CH2:20]2)[c:21]1[OH:22] | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC1C=CCCC1 | COC(=O)c1cc(Cl)c(NC(C)=O)c(C2CC=CCC2)c1O | null | null | C(C)(=O)OCC.CCCCCC | Miscellaneous | OtherReaction | 569cf2a9dcbf11611f60cb57595ce0c0c8aedca08621cdccd9f2fd36a07bc678 | 0bab01685da92cdead9c84b3a9c513c0e9bd4114585991beae2460d8c47b3623 | C1=CCC(c2ccccc2)CC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[O;H0;D2;+0:6]-[CH;D3;+0:7]1-[C:8]-[C:9]-[CH2;D2;+0:10]-[CH;D2;+0:11]=[CH;D2;+0:12]-1):[cH;D2;+0:13]:[c:14](-[#7:15]-[C:16](-[C;D1;H3:17])=[O;D1;H0:18]):[c:19]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c;H0;D3;+0:13](-[CH;D3;+0:7]1-[C:8]-[C:9]-[CH;D2;+0:10]=[CH;D2;+... | null | [] | 220 | CELSIUS | null | null | A mixture of 0.6 g of methyl 2-(cyclohexen-3-yloxy)-4-acetylamino-5-chlorobenzoate and 0.5 ml diethylamiline is placed under house vacuum and heated to 220° C. for 2 hours. This reaction mixture is then diluted with 40% ethyl acetate/hexane and purified by dry column chromatography using the same solvent system as elue... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1.C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | null | C(C)(=O)OCC.CCCCCC | 220 | null | COC(=O)c1cc(Cl)c(NC(C)=O)cc1OC1C=CCCC1>C(C)(=O)OCC.CCCCCC>COC(=O)c1cc(Cl)c(NC(C)=O)c(C2CC=CCC2)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-59cc86bc4e3c4b42bb0e0e6a3f0c01e9 | COC(=O)c1cc(Cl)c(NC(C)=O)c(C2CC=CCC2)c1O>>COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21 | C1(CC=CCC1)C1=C(C(C(=O)OC)=CC(=C1NC(C)=O)Cl)O.FC(C(=O)O)(F)F>>C(C)(=O)NC1=C(C=C(C=2OC3C(C21)CCCC3)C(=O)OC)Cl | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[c:14]([CH:22]2[CH2:17][CH2:18][CH:19]=[CH:20][CH2:21]2)[c:15]1[OH:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[c:14]2[c:15]1[O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]21 | COC(=O)c1cc(Cl)c(NC(C)=O)c(C2CC=CCC2)c1O | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 61bc038a69935a3033d9b25e0f4bd84cd94027a65f856cf1bf937f2614142f4b | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc2c(c1)OC1CCCCC21 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]-[C:8]1-[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-[C:12]-[CH2;D2;+0:13]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:7]-[C:8]2-[C:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C:12]-[CH;D3;+0:13]-2-[O;H0;D2;+0:6]-1 | null | [] | null | null | 8 | HOUR | A mixture of 1.2 g of methyl 3-(3-cyclohexenyl)-4-acetylamino-5-chlorosalicylate and 5 ml trifluoroacetic acid are stirred at room temperature overnight. The acid is removed under vacuum and the residue diluted with ether, washed with sodium bicarbonate, then water, dried and evaporated to dryness to give crude methyl ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | C1=CCCCC1 | c1ccc2c(c1)OC1CCCCC21 | c1ccc2c(c1)OC1CCCCC21 | null | null | null | 8 | COC(=O)c1cc(Cl)c(NC(C)=O)c(C2CC=CCC2)c1O>>COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1b8a2b34a645485ea55d1706e0d72126 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21>>Nc1c(Cl)cc(C(=O)O)c2c1C1CCCCC1O2 | [Na].C(C)(=O)NC1=C(C=C(C=2OC3C(C21)CCCC3)C(=O)OC)Cl>>NC1=C(C=C(C=2OC3C(C21)CCCC3)C(=O)O)Cl | CC(=O)[NH:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[O:9]C)[c:10]2[c:11]1[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:18]2>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[c:11]1[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:18]2 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21 | Nc1c(Cl)cc(C(=O)O)c2c1C1CCCCC1O2 | null | null | [OH-].[Na+].CO | Reduction | OtherReaction | 452a6d5c131a88ae20736ca8e7c212113584fd8119891c3dedd356fb46573207 | 01841db25d7c9417dbf2fcab7fb91f3616b53926525501ef73813a86303e5c4c | c1ccc2c(c1)OC1CCCCC21 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | null | [] | null | null | 2 | DAY | To a solution of 0.3 g of sodium in 15 ml methanol is added 0.6 g of methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate. Stirring is continued at 60° C. for two days. This is then diluted with 5 ml 1N sodium hydroxide and stirring continued at 60° C. overnight. The methanol is removed in va... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Carboxylic acid.Primary amine | null | null | c1ccc2c(c1)OC1CCCCC21 | HO- | [OH-].[Na+].CO | null | 48 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21>[OH-].[Na+].CO>Nc1c(Cl)cc(C(=O)O)c2c1C1CCCCC1O2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-16679a0222a54903abc287b1b5d2fb96 | Nc1c(Cl)cc(C(=O)O)c2c1C1CCCCC1O2>>Nc1c(Cl)ccc2c1C1CCCCC1O2 | C(C)OC(=O)Cl.Cl.Cl.NC1CN2CCC1CC2.NC1=C(C=C(C=2OC3C(C21)CCCC3)C(=O)O)Cl.C(C)N(CC)CC>>NC1=C(C=CC=2OC3C(C21)CCCC3)Cl | O=C(O)[c:6]1[cH:5][c:3]([Cl:4])[c:2]([NH2:1])[c:8]2[c:7]1[O:15][CH:14]1[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]1>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]2[c:8]1[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[O:15]2 | Nc1c(Cl)cc(C(=O)O)c2c1C1CCCCC1O2 | Nc1c(Cl)ccc2c1C1CCCCC1O2 | null | null | C(Cl)(Cl)Cl.O | Reduction | Decarboxylation | 6fa5311cbc78c933ad127742b88dbadb60cd974f3674206f65164231bc617ca5 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccc2c(c1)OC1CCCCC21 | O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[#8:6]-[C:7]>>[C:7]-[#8:6]-[c:4](:[c:5]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | 2 | HOUR | To a cold solution of 0.3 g 1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid in 40 ml chloroform is added 0.3 g of triethylamine and then 0.2 g ethylchloroformate in 10 ml chloroform. Stirring is continued for 2 hours. This is then added to a cold mixture of 3 g 3-aminoquinuclidine dihydrochloride... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccc2c(c1)OC1CCCCC21 | c1ccc2c(c1)OC1CCCCC21 | c1ccc2c(c1)OC1CCCCC21 | Other | C(Cl)(Cl)Cl.O | null | 2 | Nc1c(Cl)cc(C(=O)O)c2c1C1CCCCC1O2>C(Cl)(Cl)Cl.O>Nc1c(Cl)ccc2c1C1CCCCC1O2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1db8617e4e21499da3b698e0cfae349c | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21>>COC(=O)c1cc(Cl)c(NC(C)=O)c2c3c(oc12)CCCC3 | C(C)(=O)NC1=C(C=C(C=2OC3C(C21)CCCC3)C(=O)OC)Cl>>C(C)(=O)NC1=C(C=C(C=2OC3=C(C21)CCCC3)C(=O)OC)Cl | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[c:14]2[c:18]1[O:17][CH:16]1[CH:15]2[CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[c:14]2[c:15]3[c:16]([o:17][c:18]12)[CH2:19][CH2:20][CH2:21][CH2:22]3 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c3c(oc12)CCCC3 | null | null | C1=CC=CC=C1 | Oxidation | OtherReaction | 1c6602e9d7db682b5d78f44b6d35dfd006f9182a6a1955ef038b20ccef5114fc | fff4eccc0dedd8750ef9b8f7b1941b2ebb1ccaccd2575a07f597270a222f1bc8 | c1ccc2c3c(oc2c1)CCCC3 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:6](:[c:7])-[CH;D3;+0:8]2-[C:9]-[C:10]-[C:11]-[C:12]-[CH;D3;+0:13]-2-[O;H0;D2;+0:14]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[o;H0;D2;+0:14]:[c;H0;D3;+0:13]2:[c;H0;D3;+0:8](:[c:6]:1:[c:7])-[C:9]-[C:10]-[C:11]-[C:12]-2 | null | [] | 80 | CELSIUS | null | null | A mixture of 1 g methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate and 1 g of dichlorodicyanoquinone in 15 ml of benzene is stirred and heated at 80° C in a sealed tube for 8 hours. The cooled reaction mixture is then diluted with benzene, filtered and evaporated to dryness. Purification b... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccc2c(c1)OC1CCCCC21 | c1ccc2c3c(oc2c1)CCCC3 | c1ccc2c3c(oc2c1)CCCC3 | null | C1=CC=CC=C1 | 80 | null | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1OC1CCCCC21>C1=CC=CC=C1>COC(=O)c1cc(Cl)c(NC(C)=O)c2c3c(oc12)CCCC3 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b5e23945398f4f32a18631a3e67f1b9a | COC(=O)c1cc(Cl)c(NC(C)=O)c2c3c(oc12)CCCC3>>COC(=O)c1cc(Cl)c(NC(C)=O)c2c1oc1ccccc12 | C(C)(=O)NC1=C(C=C(C=2OC3=C(C21)CCCC3)C(=O)OC)Cl>>C(C)(=O)NC1=C(C=C(C=2OC3=C(C21)C=CC=C3)C(=O)OC)Cl | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[c:14]2[c:15]1[o:16][c:17]1[c:22]2[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[c:14]2[c:15]1[o:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]21 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c3c(oc12)CCCC3 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1oc1ccccc12 | null | [Pd] | null | Oxidation | OtherReaction | a25f65982ad22080009ca3896895bd738d0266b1aaee51bc0edc19edef8019fc | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | c1ccc2c(c1)oc1ccccc12 | [#8;a:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-2>>[#8;a:1]1:[c:2]:[c:3]:[c:4]2:[cH;D2;+0:9]:[cH;D2;+0:8]:[cH;D2;+0:7]:[cH;D2;+0:6]:[c:5]:1:2 | null | [] | 230 | CELSIUS | null | null | A mixture of 1 g methyl 1-acetylamino-2-chloro6,7,8,9-tetrahydrodibenzofuran-4-carboxylate and 0.5 g of 5% palladium-charcoal is heated under nitrogen at 230° C. for 5 hours. The cooled residue is extracted with toluene and the solvent evaporated to dryness. The residue is crystallized from ethyl acetate/hexane to give... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c(oc2c1)CCCC3 | c1ccc2c(c1)oc1ccccc12 | c1ccc2c(c1)oc1ccccc12 | null | [Pd] | 230 | null | COC(=O)c1cc(Cl)c(NC(C)=O)c2c3c(oc12)CCCC3>[Pd]>COC(=O)c1cc(Cl)c(NC(C)=O)c2c1oc1ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-be42cc45ee0b43deb2da56f808879d43 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1oc1ccccc12>>Nc1c(Cl)cc(C(=O)O)c2oc3ccccc3c12 | C(C)(=O)NC1=C(C=C(C=2OC3C(C21)CCCC3)C(=O)OC)Cl.C(C)(=O)NC1=C(C=C(C=2OC3=C(C21)CCCC3)C(=O)OC)Cl.C(C)(=O)NC1=C(C=C(C=2OC3=C(C21)C=CC=C3)C(=O)OC)Cl>>NC1=C(C=C(C=2OC3=C(C21)C=CC=C3)C(=O)O)Cl | CC(=O)[NH:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[O:9]C)[c:10]2[o:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[o:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]12 | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1oc1ccccc12 | Nc1c(Cl)cc(C(=O)O)c2oc3ccccc3c12 | null | null | null | Reduction | OtherReaction | 452a6d5c131a88ae20736ca8e7c212113584fd8119891c3dedd356fb46573207 | 01841db25d7c9417dbf2fcab7fb91f3616b53926525501ef73813a86303e5c4c | c1ccc2c(c1)oc1ccccc12 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](:[#8;a:6]):[c:7]:[c:8](-[NH;D2;+0:9]-C(-C)=O):[c:10]>>[#8;a:6]:[c:5](:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]):[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | When the procedure of Example 15 is followed however methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate is replaced by methyl 1-acetylamino-2-chloro-6,7,8,9-tetrahydrodibenzofuran-4-carboxylate or methyl 1-acetylamino-2-chlorodibenzofuran-4-carboxylate then the captioned products are prepar... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Carboxylic acid.Primary amine | null | null | c1ccc2c(c1)oc1ccccc12 | HO- | null | null | null | COC(=O)c1cc(Cl)c(NC(C)=O)c2c1oc1ccccc12>>Nc1c(Cl)cc(C(=O)O)c2oc3ccccc3c12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-74c9a7248a1c4d0fb42cc6b25cb3a847 | Nc1c(Cl)cc(C(=O)O)c2oc3ccccc3c12>>Nc1c(Cl)ccc2oc3ccccc3c12 | NC1=C(C=C(C=2OC3C(C21)CCCC3)C(=O)O)Cl.NC1=C(C=C(C=2OC3=C(C21)CCCC3)C(=O)O)Cl.NC1=C(C=C(C=2OC3=C(C21)C=CC=C3)C(=O)O)Cl>>NC1=C(C=CC=2OC3=C(C21)C=CC=C3)Cl | O=C(O)[c:6]1[cH:5][c:3]([Cl:4])[c:2]([NH2:1])[c:15]2[c:7]1[o:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]12>>[NH2:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]2[o:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]12 | Nc1c(Cl)cc(C(=O)O)c2oc3ccccc3c12 | Nc1c(Cl)ccc2oc3ccccc3c12 | null | null | null | Reduction | Decarboxylation | ec4c0a9844bdb85361894237d5fa844b562f56aba90371ef2389734899f86754 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccc2c(c1)oc1ccccc12 | O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7]>>[c:5]:[c:4](:[#8;a:6]:[c:7]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | When the procedure of Example 16 is followed however, 1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran -4-carboxylic acid is replaced by 1-amino2-chloro-6,7,8,9-tetrahydrodibenzofuran-4-carboxylic acid or 1-amino-2-chlorodibenzofuran-4-carboxylic acid then the captioned products are prepared.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccc2c(c1)oc1ccccc12 | c1ccc2c(c1)oc1ccccc12 | c1ccc2c(c1)oc1ccccc12 | Other | null | null | null | Nc1c(Cl)cc(C(=O)O)c2oc3ccccc3c12>>Nc1c(Cl)ccc2oc3ccccc3c12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-624b3fc71b5241e7a87be65e3b8537a0 | COC(=O)c1cc(Cl)cc(C2CC=CCC2)c1O>>COC(=O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@@H]21 | C1(CC=CCC1)C1=C(C(C(=O)OC)=CC(=C1)Cl)O>>ClC1=CC2=C(O[C@H]3[C@H]2CCCC3)C(=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]([CH:18]2[CH2:13][CH2:14][CH:15]=[CH:16][CH2:17]2)[c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]2[c:11]1[O:12][C@@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]21 | COC(=O)c1cc(Cl)cc(C2CC=CCC2)c1O | COC(=O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@@H]21 | null | null | FC(C(=O)O)(F)F | Heteroatom Alkylation and Arylation | OtherReaction | 5aba3028cc0dd063a4dc7378323642e9ebc8c42f4b1eb741f5dacc7a315b2251 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc2c(c1)O[C@@H]1CCCC[C@@H]21 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7](-[CH;D3;+0:8]1-[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-[C:12]-[CH2;D2;+0:13]-1):[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:7](:[c:14])-[C@@H;D3;+0:8]2-[C:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C:12]-[C@H;D3;+0:13]-2-[O;H0;D2;+0:6]-1 | null | [] | 70 | CELSIUS | null | null | A mixture of 9 g of methyl 3-(3-cyclohexenyl)-5chlorosalicylate and 20 ml trifluoroacetic acid is heated at 70° C. overnight. The cooled reaction mixture is diluted with hexanes, washed three times with water, dried and evaporated to dryness. The residue is purified with flash chromatography using 10% ethyl acetate/hex... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | C1=CCCCC1 | c1ccc2c(c1)O[C@@H]1CCCC[C@@H]21 | c1ccc2c(c1)O[C@@H]1CCCC[C@@H]21 | null | FC(C(=O)O)(F)F | 70 | null | COC(=O)c1cc(Cl)cc(C2CC=CCC2)c1O>FC(C(=O)O)(F)F>COC(=O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@@H]21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fe043d08703d4db0a5c9306f4b9bfdfd | COC(=O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@H]21>>O=C(O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@H]21 | ClC1=CC2=C(O[C@H]3[C@@H]2CCCC3)C(=C1)C(=O)OC>>ClC1=CC2=C(O[C@H]3[C@@H]2CCCC3)C(=C1)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[O:11][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]21>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[O:11][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]21 | COC(=O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@H]21 | O=C(O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@H]21 | null | null | [OH-].[Na+].O.O1CCOCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)O[C@@H]1CCCC[C@H]21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 60 | CELSIUS | 5 | HOUR | A mixture of 2 g methyl 2-chloro-cis-5a,6,7,8, 9,9a-hexahydrodibenzofuran-4-carboxylate in 30 ml 1N sodium hydroxide and 5 ml dioxane is stirred at 60° C. for 5 hours. This is then diluted with water, filtered, acidified with acetic acid, extracted with ethyl acetate, dried over magnesium sulfate and evaporated to dryn... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)O[C@@H]1CCCC[C@H]21 | Other | [OH-].[Na+].O.O1CCOCC1 | 60 | 5 | COC(=O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@H]21>[OH-].[Na+].O.O1CCOCC1>O=C(O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@H]21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5f7c51d628ad4fcda89d3d4a2d4eafae | Clc1ccncc1.Cn1ccc2cc(N)ccc21>>Cn1ccc2cc(Nc3ccncc3)ccc21 | O.Cl.ClC1=CC=NC=C1.NC=1C=C2C=CN(C2=CC1)C.C([O-])([O-])=O.[Na+].[Na+].Cl.ClC1=CC=NC=C1>>CN1C=CC2=CC(=CC=C12)NC1=CC=NC=C1 | Cl[c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1.[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH2:8])[cH:15][cH:16][c:17]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[cH:10][cH:11][n:12][cH:13][cH:14]3)[cH:15][cH:16][c:17]12 | Clc1ccncc1.Cn1ccc2cc(N)ccc21 | Cn1ccc2cc(Nc3ccncc3)ccc21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3[nH]ccc3c2)ccn1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | 53.3 | [{"value": 53.3, "product": "CN1C=CC2=CC(=CC=C12)NC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloropyridine hydrochloride (8 g) was added to a solution of 5-amino-1-methylindole (7 g) in 75 ml 1-methyl-2-pyrrolidinone preheated to 100° C. The addition of 4-chloropyridine hydrochloride (4 g) after one hour caused no further reaction as determined by TLC. After two hours the reaction mixture was cooled, stirre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2[nH]ccc2c1.c1ccncc1 | HCl | CN1C(CCC1)=O | null | null | Clc1ccncc1.Cn1ccc2cc(N)ccc21>CN1C(CCC1)=O>Cn1ccc2cc(Nc3ccncc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-299b2716a8194ac09bde2f6df2151eb9 | COC(=O)Cl.Cn1ccc2cc(Nc3ccncc3)ccc21>>COC(=O)N(c1ccncc1)c1ccc2c(ccn2C)c1 | ClC(=O)OC.CN1C=CC2=CC(=CC=C12)NC1=CC=NC=C1>>COC(N(C1=CC=NC=C1)C=1C=C2C=CN(C2=CC1)C)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH:5]([c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17][cH:18][n:19]2[CH3:20])[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17][cH:18][n:19]2[CH3:20])[cH:21]1 | COC(=O)Cl.Cn1ccc2cc(Nc3ccncc3)ccc21 | COC(=O)N(c1ccncc1)c1ccc2c(ccn2C)c1 | null | null | C(Cl)Cl.C(C)N(CC)CC | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | c1cc(Nc2ccc3[nH]ccc3c2)ccn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[c:5]:[c:6](-[NH;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1):[c:14]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[c:6](:[c:5]):[c:14])-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1 | 98.4 | [{"value": 98.4, "product": "COC(N(C1=CC=NC=C1)C=1C=C2C=CN(C2=CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of methyl chloroformate (1.3 g) in 5 ml DCM was added to a solution of 1-methyl-5-(4-pyridinylamino)-1H-indole (2.5 g) in 120 ml DCM and 6 ml triethylamine (4.4 g). After stirring one hour at ambient temperature the reaction mixture was washed with water and saturated sodium chloride, dried (anhydrous magnes... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1ccncc1.c1ccc2[nH]ccc2c1 | HCl | C(Cl)Cl.C(C)N(CC)CC | null | 1 | COC(=O)Cl.Cn1ccc2cc(Nc3ccncc3)ccc21>C(Cl)Cl.C(C)N(CC)CC>COC(=O)N(c1ccncc1)c1ccc2c(ccn2C)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-298bebeb19ee46cc914e96bb394464b0 | CS(=O)(=O)Nc1ccc(C(=O)CCC(=O)O)cc1.On1nnc2ccccc21>>Cc1cccc(CCN)n1 | ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1.CS(=O)(=O)NC1=CC=C(C=C1)C(CCC(=O)O)=O>>CC1=CC=CC(=N1)CCN | O=C(O)CC[C:7](=O)[c:6]1ccc([NH:9]S(=O)(=O)[CH3:8])cc1.O[n:10]1nn[c:1]2c[cH:5][cH:4][cH:3][c:2]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][CH2:8][NH2:9])[n:10]1 | CS(=O)(=O)Nc1ccc(C(=O)CCC(=O)O)cc1.On1nnc2ccccc21 | Cc1cccc(CCN)n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 6cd6b7546105713c5b20431fc54a0ee11e82cdaa7f54bb0be62fbc71bebf86a0 | 07c711d9e7d09b38ec62312a068b81e13e459dbfde16b689bede4a00b10310ae | c1ccncc1 | O-C(=O)-C-C-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:c:c:c(-[NH;D2;+0:3]-S(=O)(=O)-[CH3;D1;+0:4]):c:c:1.O-[n;H0;D3;+0:5]1:n:n:[c;H0;D3;+0:6]2:c:[cH;D2;+0:7]:[c:8]:[c:9]:[c:10]:2:1>>[CH3;D1;+0:6]-[c:10]1:[c:9]:[c:8]:[cH;D2;+0:7]:[c;H0;D3;+0:2](-[CH2;D2;+0:1]-[CH2;D2;+0:4]-[NH2;D1;+0:3]):[n;H0;D2;+0:5]:1 | 100 | [{"value": 100.0, "product": "CC1=CC=CC(=N1)CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4.76 g (35.3 mmol) of 1-hydroxybenzotriazole and 7.27 g (35.3 mmol) of dicyclohexylcarbodiimide were added to a solution of 7.02 g (29.4 mmol) of 4-(4-methylsulfonylaminophenyl)-4-oxobutyric acid in 60 ml of dimethylformamide at 0° C. and the mixture was stirred at that temperature for 1 h. 4.80 g (35.3 mmol) of 2-(6-m... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid.Ketone | Primary amine | c1ccccc1.c1ccc2[nH]nnc2c1 | c1ccncc1 | c1ccncc1 | HO- | CN(C=O)C | null | 1 | CS(=O)(=O)Nc1ccc(C(=O)CCC(=O)O)cc1.On1nnc2ccccc21>CN(C=O)C>Cc1cccc(CCN)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0b20c9191db0436d9a89e14bbc14aaef | BrCc1ccccc1.COc1cccc(C=O)c1O>>COc1cccc(C=O)c1OCc1ccccc1 | O=CC1=C(O)C(OC)=CC=C1.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>COC=1C(=C(C=O)C=CC1)OCC1=CC=CC=C1 | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | BrCc1ccccc1.COc1cccc(C=O)c1O | COc1cccc(C=O)c1OCc1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:10] | 93 | [{"value": 84.0, "product": "COC=1C(=C(C=O)C=CC1)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "COC=1C(=C(C=O)C=CC1)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 196.0 g (1.30 mole) of o-vanillin (Aldrich), 200 g of benzyl bromide (Aldrich), 500 g of anhydrous potassium carbonate and 1,500 mL of absolute ethanol is heated, with stirring, at reflux for 6 hours. After cooling, the supernatant is decanted and the remainder is filtered. The combined filtrate and supern... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)O | null | null | BrCc1ccccc1.COc1cccc(C=O)c1O>C(C)O>COc1cccc(C=O)c1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a122cc9a717e46b8bd8eec79a39f674d | COc1cccc(C=O)c1O.O=[N+]([O-])c1ccc(F)cc1>>COc1cccc(C=O)c1Oc1ccc([N+](=O)[O-])cc1 | FC1=CC=C(C=C1)[N+](=O)[O-].O=CC1=C(O)C(OC)=CC=C1.C([O-])([O-])=O.[K+].[K+]>>COC=1C(=C(C=O)C=CC1)OC1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[OH:11].F[c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[O:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1 | COc1cccc(C=O)c1O.O=[N+]([O-])c1ccc(F)cc1 | COc1cccc(C=O)c1Oc1ccc([N+](=O)[O-])cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11] | 71 | [{"value": 71.0, "product": "COC=1C(=C(C=O)C=CC1)OC1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 14.10 g (0.10 mole) of 4-fluoronitrobenzene, 16.40 g (0.10 mole) of o-vanillin, 30 g of powdered potassium carbonate, and 40 mL of DMF is heated with stirring to the boiling point. After 10 minutes the mixture is cooled to 100° C. and 300 mL of ice water is added. Petroleum ether (200 mL) is added and the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CN(C)C=O | 100 | null | COc1cccc(C=O)c1O.O=[N+]([O-])c1ccc(F)cc1>CN(C)C=O>COc1cccc(C=O)c1Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3df598706a6341029bbe0e51dc330ad2 | COc1cccc(C=O)c1OCc1ccccc1.O=C1CNC(=O)N1>>COc1cccc(C=C2NC(=O)NC2=O)c1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=O)C=CC=C1OC.N1C(=O)NC(=O)C1.NCCC(=O)O.C(C)(=O)O>>COC=1C(=C(C=CC1)C=C1C(NC(N1)=O)=O)OCC1=CC=CC=C1 | O=[CH:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[CH2:9]1[NH:10][C:11](=[O:12])[NH:13][C:14]1=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[C:9]2[NH:10][C:11](=[O:12])[NH:13][C:14]2=[O:15])[c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH... | COc1cccc(C=O)c1OCc1ccccc1.O=C1CNC(=O)N1 | COc1cccc(C=C2NC(=O)NC2=O)c1OCc1ccccc1 | null | null | O | C-C Coupling | Aldol condensation | b678f4401483db5ade2dc92377cdc2cf9bd928d137bf3f94f3d048a1d4972563 | 36fae40c616209f3c4ff3e32e7faa1d5252a5a368f7252b830c0334be626d00c | O=C1NC(=O)C(=Cc2ccccc2OCc2ccccc2)N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#7:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#7:11]-1 | 84 | [{"value": 84.0, "product": "COC=1C(=C(C=CC1)C=C1C(NC(N1)=O)=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 96.90 g (0.40 mole) of 2-benzyloxy-3-methoxybenzaldehyde, 48.04 g (0.48 mole) of hydantoin, 8.02 g (0.09 mole) of β-alanine, and 200 mL of glacial acetic acid is stirred at reflux for 6 hours. Water (500 mL) is added and the separated solid is filtered, washed well with water, methanol, and then ether; wt... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Enamine | C1CNCN1 | C1CNCN1 | c1ccccc1.C1CNCN1.c1ccccc1 | HO- | O | null | null | COc1cccc(C=O)c1OCc1ccccc1.O=C1CNC(=O)N1>O>COc1cccc(C=C2NC(=O)NC2=O)c1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3b6e898593fa40f990872efa8f46e0d5 | COc1cccc(C=C2NC(=O)NC2=O)c1OCc1ccccc1>>COc1cccc(CC2NC(=O)NC2=O)c1OCc1ccccc1 | Cl.Cl.COC=1C(=C(C=CC1)C=C1C(NC(N1)=O)=O)OCC1=CC=CC=C1.C(C1=CC=CC=C1)=C1C(NC(N1)=O)=O>>COC=1C(=C(C=CC1)CC1C(NC(N1)=O)=O)OCC1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[C:9]2[NH:10][C:11](=[O:12])[NH:13][C:14]2=[O:15])[c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH:9]2[NH:10][C:11](=[O:12])[NH:13][C:14]2=[O:15])[c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23... | COc1cccc(C=C2NC(=O)NC2=O)c1OCc1ccccc1 | COc1cccc(CC2NC(=O)NC2=O)c1OCc1ccccc1 | null | [Zn] | CO | Reduction | Hydrogenation (double to single) | 14bc0a666658340302033de53c382b0620c1a3a22c106d02729f4ccfaf9893bb | 6e6bc99be91066164ab9bf04e83a0e2c8a589cd3042e04e2a8cea8a9cb7243a6 | O=C1NC(=O)C(Cc2ccccc2OCc2ccccc2)N1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C;H0;D3;+0:4](=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#7:11]-1>>[O;D1;H0:1]=[C:2]1-[#7:3]-[CH;D3;+0:4](-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#7:11]-1 | 47.1 | [{"value": 47.1, "product": "COC=1C(=C(C=CC1)CC1C(NC(N1)=O)=O)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | Zinc powder (40.00 g; 0.61 mole) is added to a stirred suspension of 48.00 g (0.16 mole) of the benzylidine hydantoin from Example 3 in 1,200 mL of methanol under nitrogen. Concentrated hydrochloric acid (30 mL) is added and the mixture is heated on the steam bath for 20 minutes (after 10 minutes the starting benzylide... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | null | C1CNCN1 | C1CNCN1 | c1ccccc1.C1CNCN1.c1ccccc1 | null | [Zn].CO | 50 | null | COc1cccc(C=C2NC(=O)NC2=O)c1OCc1ccccc1>[Zn].CO>COc1cccc(CC2NC(=O)NC2=O)c1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eefe78a39ad249cdbf4dd0afd48c7156 | COc1ccc(CC2NC(=O)NC2=O)cc1OCc1ccccc1.O=C1c2ccccc2C(=O)C1(O)O>>COc1ccc(CC(N)C(=O)O)cc1OCc1ccccc1 | COC1=C(C=C(C=C1)CC1C(NC(N1)=O)=O)OCC1=CC=CC=C1.C1=CC=C2C(=C1)C(=O)C(C2=O)(O)O>>COC1=C(C=C(CC(N)C(=O)O)C=C1)OCC1=CC=CC=C1 | O=C1N[C:10](=[O:11])[CH:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:13]2)[NH:9]1.O=C1c2ccccc2C(=O)C1(O)[OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH:8]([NH2:9])[C:10](=[O:11])[OH:12])[cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20... | COc1ccc(CC2NC(=O)NC2=O)cc1OCc1ccccc1.O=C1c2ccccc2C(=O)C1(O)O | COc1ccc(CC(N)C(=O)O)cc1OCc1ccccc1 | null | null | C(C)(=O)O.CO.C(Cl)(Cl)Cl | Acylation | OtherReaction | 57a7de76b7782c33004219388a8ab47d399fc30d836a70fa18b6090e7136cf6f | c4fddf69babcd7d9707fbeedcd140680e52dbf3f4640fa30659bd4f78e8f35f1 | c1ccc(COc2ccccc2)cc1 | O-C1(-[OH;D1;+0:1])-C(=O)-c2:c:c:c:c:c:2-C-1=O.O=C1-N-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[NH;D2;+0:6]-1>>[C:5]-[C:4](-[NH2;D1;+0:6])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | This compound is prepared from the corresponding hydantoin derivative (Example 7) by a procedure similar to that in Example 9; tlc (1:5:20 acetic acid-methanol-chloroform system); Rf 0.4 (ninhydrin).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Urea.Unsubstituted dicarboximide.Tertiary alcohol.Tertiary alcohol | Carboxylic acid.Primary amine | C1CNCN1.c1ccc2c(c1)CCC2 | null | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.CO.C(Cl)(Cl)Cl | null | null | COc1ccc(CC2NC(=O)NC2=O)cc1OCc1ccccc1.O=C1c2ccccc2C(=O)C1(O)O>C(C)(=O)O.CO.C(Cl)(Cl)Cl>COc1ccc(CC(N)C(=O)O)cc1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7bee3f2deba042d7930137633227fc6b | CCOC(=O)C1Cc2c(ccc(OC)c2OCc2ccc(C(=O)OC)cc2)CN1C(=O)C(c1ccccc1)c1ccccc1>>COc1ccc2c(c1OCc1ccc(C(=O)O)cc1)CC(C(=O)O)N(C(=O)C(c1ccccc1)c1ccccc1)C2 | C(=O)(OC)C1=CC=C(C=C1)COC1=C2CC(N(CC2=CC=C1OC)C(C(C1=CC=CC=C1)C1=CC=CC=C1)=O)C(=O)OCC>>C(=O)(O)C1=CC=C(C=C1)COC1=C2CC(N(CC2=CC=C1OC)C(C(C1=CC=CC=C1)C1=CC=CC=C1)=O)C(=O)O | CC[O:24][C:22]([CH:21]1[CH2:20][c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]2[O:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17]C)[cH:18][cH:19]2)[CH2:41][N:25]1[C:26](=[O:27])[CH:28]([c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1)[c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1)=[O:23]>>[CH3:1][O:2][c:3]1[cH:4][... | CCOC(=O)C1Cc2c(ccc(OC)c2OCc2ccc(C(=O)OC)cc2)CN1C(=O)C(c1ccccc1)c1ccccc1 | COc1ccc2c(c1OCc1ccc(C(=O)O)cc1)CC(C(=O)O)N(C(=O)C(c1ccccc1)c1ccccc1)C2 | null | null | [OH-].[Na+].CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | O=C(C(c1ccccc1)c1ccccc1)N1CCc2c(cccc2OCc2ccccc2)C1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5].C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[c:9] | null | [] | null | null | null | null | A solution of 1.10 g (0.0019 mole) of the diester from Example 32 in 100 mL of methanol and 15 mL of 2N sodium hydroxide is heated to the boiling point, allowing the methanol to distill off. After 1 hour (pot temperature =90° C.), 1N hydrochloric acid (35 mL) is added to precipitate a gum. On addition of 10 mL of ether... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]C2.c1ccccc1.c1ccccc1 | Other | [OH-].[Na+].CO | null | null | CCOC(=O)C1Cc2c(ccc(OC)c2OCc2ccc(C(=O)OC)cc2)CN1C(=O)C(c1ccccc1)c1ccccc1>[OH-].[Na+].CO>COc1ccc2c(c1OCc1ccc(C(=O)O)cc1)CC(C(=O)O)N(C(=O)C(c1ccccc1)c1ccccc1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5863e731e9c84c6190da1db07ffc1880 | CCOC(=O)C1Cc2c(ccc(OC)c2O)CN1C(=O)C(c1ccccc1)c1ccccc1.COc1ccc(CCl)cc1C>>CCOC(=O)C1Cc2c(ccc(OC)c2OCc2ccc(OC)c(C)c2)CN1C(=O)C(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C(C(=O)N1CC2=CC=C(C(=C2CC1C(=O)OCC)O)OC)C1=CC=CC=C1.COC1=C(C=C(CCl)C=C1)C>>C1(=CC=CC=C1)C(C(=O)N1CC2=CC=C(C(=C2CC1C(=O)OCC)OCC1=CC(=C(C=C1)OC)C)OC)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[c:9]([cH:10][cH:11][c:12]([O:13][CH3:14])[c:15]2[OH:16])[CH2:27][N:28]1[C:29](=[O:30])[CH:31]([c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[c:38]1[cH:39][cH:40][cH:41][cH:42][cH:43]1.Cl[CH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH3:23])[c:24]([CH3:25])[cH:26]1>>[CH3:1... | CCOC(=O)C1Cc2c(ccc(OC)c2O)CN1C(=O)C(c1ccccc1)c1ccccc1.COc1ccc(CCl)cc1C | CCOC(=O)C1Cc2c(ccc(OC)c2OCc2ccc(OC)c(C)c2)CN1C(=O)C(c1ccccc1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(C(c1ccccc1)c1ccccc1)N1CCc2c(cccc2OCc2ccccc2)C1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | This compound is prepared from the phenol derivative of Example 31 and 4-methoxy-3-methyl benzyl chloride by a procedure similar to that in Example 32. The product is purified by silica gel chromatography; tlc (1:1 ethyl-acetate/hexane), one spot, Rf 0.7.
Conditions: See reaction.notes.procedure_details.
Workup: The pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CC[NH]C2.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)C1Cc2c(ccc(OC)c2O)CN1C(=O)C(c1ccccc1)c1ccccc1.COc1ccc(CCl)cc1C>>CCOC(=O)C1Cc2c(ccc(OC)c2OCc2ccc(OC)c(C)c2)CN1C(=O)C(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-27c222d747194cee97fae27c69eb7117 | COc1cccc(C=O)c1OCc1ccccc1>>COc1cccc(CO)c1OCc1ccccc1 | [BH4-].[Na+].C(C1=CC=CC=C1)OC1=C(C=O)C=CC=C1OC.CC(=O)C>>C(C1=CC=CC=C1)OC1=C(CO)C=CC=C1OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][OH:9])[c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | COc1cccc(C=O)c1OCc1ccccc1 | COc1cccc(CO)c1OCc1ccccc1 | null | null | C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(COc2ccccc2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)OC1=C(CO)C=CC=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.7, "product": "C(C1=CC=CC=C1)OC1=C(CO)C=CC=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 43.00 g (0.18 mole) of 2-benzyloxy-3-methoxy-benzaldehyde of Example 1 in 300 mL of absolute ethanol is treated, with stirring, with 7.56 g (0.20 mole) of sodium borohydride. The temperature rises to 50° C. After one-half hour 10 mL of acetone is added, keeping the temperature at less than 60° C. with coo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | null | C(C)O | null | 0.25 | COc1cccc(C=O)c1OCc1ccccc1>C(C)O>COc1cccc(CO)c1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f93f0562c268458cb7f1687b9cb17055 | CCOC(=O)C(NC(C)=O)C(=O)OCC.COc1cccc(CCl)c1OCc1ccccc1>>CCOC(=O)C(Cc1cccc(OC)c1OCc1ccccc1)(NC(C)=O)C(=O)OCC | O.[O-]CC.[Na+].C(C)(=O)NC(C(=O)OCC)C(=O)OCC.ClCC=1C(=C(C=CC1)OC)OCC1=CC=CC=C1>>C(C)(=O)NC(C(=O)OCC)(C(=O)OCC)CC1=C(C(=CC=C1)OC)OCC1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:24][C:25]([CH3:26])=[O:27])[C:28](=[O:29])[O:30][CH2:31][CH3:32].Cl[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][CH3:14])[c:15]1[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][CH3:... | CCOC(=O)C(NC(C)=O)C(=O)OCC.COc1cccc(CCl)c1OCc1ccccc1 | CCOC(=O)C(Cc1cccc(OC)c1OCc1ccccc1)(NC(C)=O)C(=O)OCC | null | null | C(C)(=O)O.C(C)O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[#7:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[#7:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14](=[O;D1;H0:15])-[#8... | 66.4 | [{"value": 66.4, "product": "C(C)(=O)NC(C(=O)OCC)(C(=O)OCC)CC1=C(C(=CC=C1)OC)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A quantity of 136.20 g (0.42 mole) of 21 wt.% sodium ethoxide in ethanol is added to a stirred solution of 90.14 g (0.415 mole) of diethyl acetamidomalonate (Aldrich) in 800 mL of absolute ethanol. A solution of the benzyl chloride derivative of Example 38 in 500 mL of absolute ethanol is added and the mixture is heate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccccc1.c1ccccc1 | HCl | C(C)(=O)O.C(C)O | null | null | CCOC(=O)C(NC(C)=O)C(=O)OCC.COc1cccc(CCl)c1OCc1ccccc1>C(C)(=O)O.C(C)O>CCOC(=O)C(Cc1cccc(OC)c1OCc1ccccc1)(NC(C)=O)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bd3436a3a9104be29be12b6fb5ed6ff9 | NCCc1ccc(O)c(O)c1.O=C(Cl)OCc1ccccc1>>O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)Cl.Cl.B([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.NCCC1=CC(O)=C(O)C=C1.[OH-].[Na+].[OH-].[Na+]>>C(=O)(OCC1=CC=CC=C1)NCCC1=CC(O)=C(O)C=C1 | [NH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([OH:12])[cH:13]1.Cl[C:2](=[O:1])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([OH:12])[cH:13]1)[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | NCCc1ccc(O)c(O)c1.O=C(Cl)OCc1ccccc1 | O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1 | null | null | O | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(NCCc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 96.5 | [{"value": 96.5, "product": "C(=O)(OCC1=CC=CC=C1)NCCC1=CC(O)=C(O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 4 | HOUR | 38.2 g (100 mmol) of sodium borate and 18.9 g (100 mmol) of dopamine hydrochloride were dissolved in 250 ml of water. To the solution thus obtained, was added a 2 N sodium hydroxide solution under a nitrogen gas stream to adjust the pH value to 9. Then 17.1 g (100 mmol) of benzyloxycarbonyl chloride was added dropwise ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1 | HCl | O | 15 | 4 | NCCc1ccc(O)c(O)c1.O=C(Cl)OCc1ccccc1>O>O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6fe171cac3394eb48c1880f35356692c | CC(C)(C)C(=O)Cl.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1>>CC(C)(C)C(=O)Oc1ccc(CCNC(=O)OCc2ccccc2)cc1OC(=O)C(C)(C)C | C(C(C)(C)C)(=O)Cl.C(=O)(OCC1=CC=CC=C1)NCCC1=CC(O)=C(O)C=C1.C([O-])([O-])=O.[Na+].[Na+]>>C(C(C)(C)C)(=O)OC=1C=C(CCNC(=O)OCC2=CC=CC=C2)C=CC1OC(C(C)(C)C)=O | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:30])=[O:6].[OH:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][c:26]1[OH:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][CH2... | CC(C)(C)C(=O)Cl.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1 | CC(C)(C)C(=O)Oc1ccc(CCNC(=O)OCc2ccccc2)cc1OC(=O)C(C)(C)C | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 869b7d861b25bbd1963039cad45ba89ae5a8fd3fd5329e65fc235ed4db0f1bff | 36cfc0dfc6e686e373362e52b721129071e57c9e5877be2f6c032a4715795b10 | O=C(NCCc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH3;D1;+0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[C;D1;H3:4]-[C;H0;D4;+0:3](-[C;D1;H3:5])(-[C;D1;H3:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:11]-[c:10](:[c:12]):[c:8](-[O;H0;D2;+0:7]-[C:14](=[O;D1;H0:15])-[C;H0;D4;+0:... | 80.1 | [{"value": 80.1, "product": "C(C(C)(C)C)(=O)OC=1C=C(CCNC(=O)OCC2=CC=CC=C2)C=CC1OC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 150 ml of a pyridine solution containing 23.0 g (98 mmol) of N-carbobenzoxydopamine obtained in Synthetic Example 1-(1), was added 24.1 g (200 mmol) of pivaloyl chloride dropwise at 5° to 10° C. After stirring at room temperature for 12 hours, the mixture was allowed to react at 35° to 40° C. for 3 hours. Further, t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol.Aromatic alcohol | Ester.Ester | null | null | c1ccccc1.c1ccccc1 | null | N1=CC=CC=C1 | null | 12 | CC(C)(C)C(=O)Cl.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1>N1=CC=CC=C1>CC(C)(C)C(=O)Oc1ccc(CCNC(=O)OCc2ccccc2)cc1OC(=O)C(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8bde2442c4a143c2beb25e6049687eb8 | CC(C)C(=O)Cl.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1.c1ccncc1>>CC(C)C(=O)Oc1ccc(CCNC(=O)OCc2ccccc2)cc1OC(=O)C(C)C | C(C(C)C)(=O)Cl.C(=O)(OCC1=CC=CC=C1)NCCC1=CC(O)=C(O)C=C1.N1=CC=CC=C1.C([O-])([O-])=O.[Na+].[Na+]>>C(C(C)C)(=O)OC=1C=C(CCNC(=O)OCC2=CC=CC=C2)C=CC1OC(C(C)C)=O | Cl[C:4]([CH:2]([CH3:3])[CH3:31])=[O:5].[OH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][c:25]1[OH:26].c1c[cH:1][cH:29][cH:30]n1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][C:14](=[O:15])[O... | CC(C)C(=O)Cl.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1.c1ccncc1 | CC(C)C(=O)Oc1ccc(CCNC(=O)OCc2ccccc2)cc1OC(=O)C(C)C | null | null | null | Acylation | OtherReaction | a2a4c9ad4808da12a426245fd0c49ddf48620079d85aab729fb046caba453cab | 36cfc0dfc6e686e373362e52b721129071e57c9e5877be2f6c032a4715795b10 | O=C(NCCc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[CH3;D1;+0:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11].[cH;D2;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:n:c:c:1>>[C;D1;H3:4]-[CH;D3;+0:3](-[CH3;D1;+0:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:7](-[O;H0;D2;+0:6]-[C:15](=[O;D1;H... | 74.7 | [{"value": 74.7, "product": "C(C(C)C)(=O)OC=1C=C(CCNC(=O)OCC2=CC=CC=C2)C=CC1OC(C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 80 ml of a pyridine solution containing 10.7 g (37 mmol) of N-carbobenzoxydopamine obtained in Synthetic Example 1-(1) was added dropwise 9.9 g (93 mmol) of isobutyryl chloride at 5° to 10° C. After stirring at room temperature for 12 hours, the mixture was allowed to react at 35° to 40° C. for 3 hours. Then, the re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol.Aromatic alcohol | Ester.Ester | c1ccncc1 | null | c1ccccc1.c1ccccc1 | Other | null | null | 12 | CC(C)C(=O)Cl.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1.c1ccncc1>>CC(C)C(=O)Oc1ccc(CCNC(=O)OCc2ccccc2)cc1OC(=O)C(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-904e0eff30db466b8a5980cfec8f75e8 | O=C(Cl)c1cccnc1.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1>>O=C(NCCc1ccc(OC(=O)c2cccnc2)c(OC(=O)c2cccnc2)c1)OCc1ccccc1 | Cl.C(C1=CN=CC=C1)(=O)Cl.C(=O)(OCC1=CC=CC=C1)NCCC1=CC(O)=C(O)C=C1>>C(C1=CN=CC=C1)(=O)OC=1C=C(CCNC(=O)OCC2=CC=CC=C2)C=CC1OC(C1=CN=CC=C1)=O | Cl[C:21](=[O:22])[c:23]1[cH:18][n:17][cH:16][cH:25][cH:24]1.[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:19]([OH:12])[cH:29]1)[O:30][CH2:31][c:32]1[cH:33][cH:11][cH:35][cH:36][cH:37]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][n:17][c... | O=C(Cl)c1cccnc1.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1 | O=C(NCCc1ccc(OC(=O)c2cccnc2)c(OC(=O)c2cccnc2)c1)OCc1ccccc1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 62d64a8ee25ebf3028c7e6603e542a3d7e1f4c3abbe9aba2aecba9d2495a6d4e | 3d3f38e9779da9f3406107ede4049637c799b79fb6820e32bd706f6fc6603fe5 | O=C(NCCc1ccc(OC(=O)c2cccnc2)c(OC(=O)c2cccnc2)c1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[#7;a:7]:[cH;D2;+0:8]:1.[C:9]-[c:10]1:[c:11]:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:1.[OH;D1;+0:16]-[c:17](:[c:18]):[c;H0;D3;+0:19](-[OH;D1;+0:20]):[c:21]:[c:22]>>[C:9]-[c:10]1:[c:11]:[c:12]:[cH;D2;+0:13]:[c:23]:[cH;D2;+0:15]:1.[O... | 71.6 | [{"value": 71.6, "product": "C(C1=CN=CC=C1)(=O)OC=1C=C(CCNC(=O)OCC2=CC=CC=C2)C=CC1OC(C1=CN=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 19.0 g (66 mmol) of N-carbobenzoxydopamine obtained in Synthetic Example 1-(1) and 37.2 g (209 mmol) of hydrochloride of nicotinoyl chloride were added to 200 ml of pyridine. After stirring at room temperature for 12 hours, the mixture was allowed to react at 35°-40° C. for 2 hours. Then, the reaction mixture was poure... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol.Aromatic alcohol | Ester.Ester | c1ccncc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccncc1.c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1.c1ccncc1.c1ccccc1 | null | N1=CC=CC=C1 | null | 12 | O=C(Cl)c1cccnc1.O=C(NCCc1ccc(O)c(O)c1)OCc1ccccc1>N1=CC=CC=C1>O=C(NCCc1ccc(OC(=O)c2cccnc2)c(OC(=O)c2cccnc2)c1)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b569c1ae7f254c1eafd9b59845937ce8 | O=Cc1cccnc1.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CCCC2)cc1>>C(=C1CCCC1)c1cccnc1 | [Br-].C1(CCCC1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)([O-])C.[K+].N1=CC(=CC=C1)C=O>>C1(CCCC1)=CC=1C=NC=CC1 | O=[CH:1][c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6]2)cc1>>[CH:1](=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6]1)[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1 | O=Cc1cccnc1.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CCCC2)cc1 | C(=C1CCCC1)c1cccnc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | f1a9e9142e2fdc18994c8f2e1e4448d16b444db565878e90356478ddba8fbf7d | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C1CCCC1)c1cccnc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[CH;D3;+0:11]-1-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:6]:[#7;a:5]:[c:4]:[c:2](-[CH;D2;+0:1]=[C;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[c:3] | 61.8 | [{"value": 61.8, "product": "C1(CCCC1)=CC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 80 | MINUTE | A suspension of cyclopentyltriphenylphosphonium bromide (226 g, 0.55 mol) in anhydrous tetrahydrofuran (1000 ml) at 2° C. was treated with vigorous stirring under an atmosphere of argon, with potassium t-butoxide (61.7 g, 0.55 mol). The dark red mixture was stirred at 5° C. for 80 minutes and then treated with pyridine... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCC1 | C1CCCC1 | C1CCCC1.c1ccncc1 | HO- | O1CCCC1 | 5 | 1.333333 | O=Cc1cccnc1.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CCCC2)cc1>O1CCCC1>C(=C1CCCC1)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-003f3d8c8e754ca59574daaeedf6427a | Brc1cccnc1.COC1CCCCC1=O>>COC1CCCCC1(O)c1cccnc1 | BrC=1C=NC=CC1.C(CCC)[Li].CCCCCC.COC1C(CCCC1)=O>>COC1C(CCCC1)(O)C=1C=NC=CC1 | Br[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1.[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1=[O:9]>>[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([OH:9])[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1 | Brc1cccnc1.COC1CCCCC1=O | COC1CCCCC1(O)c1cccnc1 | null | null | CCOCC.C(C)OCC | C-C Coupling | Grignard_alcohol | 0889ed3726a3f17ee016b975d243e66e3cb5e858ed11350afcad7f91216c358a | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cncc(C2CCCCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#8:7]-[C:8](-[C:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12]-[C:13]>>[#8:7]-[C:8](-[C:9])-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1)-[C:12]-[C:13] | 80 | [{"value": 80.0, "product": "COC1C(CCCC1)(O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2 | HOUR | To a solution of 2.5M n-butyllithium in hexane (13.2 ml, 33 mmol) at -78° C. was added diethyl ether (15 ml) followed by a solution of 3-bromopyridine (4.7 g, 30 mmol) in ether (90 ml) over a period of 10 minutes. After 1 hour at -78° C. a solution of (±)-2-methoxycyclohexanone (3.84 g, 30 mmol) in ether (20 ml) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccncc1.C1CCCCC1 | C1CCCCC1.c1ccncc1 | C1CCCCC1.c1ccncc1 | Br- | CCOCC.C(C)OCC | 20 | 2 | Brc1cccnc1.COC1CCCCC1=O>CCOCC.C(C)OCC>COC1CCCCC1(O)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-437552d324044abea55731a4552ead93 | CN=C=S.O=C1CCCCC1c1cnc2ccccc2c1>>CNC(=S)C1(c2cnc3ccccc3c2)CCCCC1=O | CN=C=S.N1=CC(=CC2=CC=CC=C12)C1C(CCCC1)=O.CC(C)([O-])C.[K+]>>CNC(=S)C1(C(CCCC1)=O)C=1C=NC2=CC=CC=C2C1 | [CH3:1][N:2]=[C:3]=[S:4].[CH:5]1([c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[cH:15]2)[CH2:16][CH2:17][CH2:18][CH2:19][C:20]1=[O:21]>>[CH3:1][NH:2][C:3](=[S:4])[C:5]1([c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[cH:15]2)[CH2:16][CH2:17][CH2:18][CH2:19][C:20]1=[O:21] | CN=C=S.O=C1CCCCC1c1cnc2ccccc2c1 | CNC(=S)C1(c2cnc3ccccc3c2)CCCCC1=O | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 4e2bdcd4221da36ce9b5bb2b2cd2da621e0e7858bf9e7c1d7b0ed409b1ea1fa8 | 8826cf9a6a81066b78559d2259ab4614fdd58a2624e223be913b158f21297e2c | O=C1CCCCC1c1cnc2ccccc2c1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[S;D1;H0:4].[C:5]-[C:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12])-[C:13](=[O;D1;H0:14])-[C:15]>>[C:5]-[C:6]-[C;H0;D4;+0:7](-[C;H0;D3;+0:3](=[S;D1;H0:4])-[NH;D2;+0:2]-[C;D1;H3:1])(-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12])-[C:13](=[O;D1;H0:14])-[C:15] | 9.4 | [{"value": 9.4, "product": "CNC(=S)C1(C(CCCC1)=O)C=1C=NC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (±)-2-(quinolin-3-yl)cyclohexanone (0.78 g, 3.5 mmol) in tetrahydrofuran (10 ml) at -5° C. was treated with potassium t-butoxide (0.43 g, 3.9 mmol) in one portion. After 25 minutes at -5° C. the deep red mixture was treated dropwise during 1 minute with a solution of methyl isothiocyanate (0.28 g, 3.9 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Isothiocyanate | Ketone.Thioamide | C1CCCCC1 | C1CCCCC1 | c1ccc2ncccc2c1.C1CCCCC1 | null | O1CCCC1 | null | null | CN=C=S.O=C1CCCCC1c1cnc2ccccc2c1>O1CCCC1>CNC(=S)C1(c2cnc3ccccc3c2)CCCCC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f209a340a88445cc9ebe2dd704042b53 | Clc1nc2ccccc2cc1C=C1CCCC1>>C(=C1CCCC1)c1cnc2ccccc2c1 | ClC1=NC2=CC=CC=C2C=C1C=C1CCCC1.[OH-].[Na+]>>C1(CCCC1)=CC=1C=NC2=CC=CC=C2C1 | Cl[c:8]1[c:7]([CH:1]=[C:2]2[CH2:3][CH2:4][CH2:5][CH2:6]2)[cH:16][c:15]2[c:10]([n:9]1)[cH:11][cH:12][cH:13][cH:14]2>>[CH:1](=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6]1)[c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1 | Clc1nc2ccccc2cc1C=C1CCCC1 | C(=C1CCCC1)c1cnc2ccccc2c1 | null | [Zn] | C(C)(=O)O | Functional Group Interconversion | Aromatic dehalogenation | 9d8b09641537c9b7067a6060cf65ecd110c7af466a7b229ce3601533f966554e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | C(=C1CCCC1)c1cnc2ccccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5]=[C:6](-[C:7])-[C:8]):[c:9]>>[C:7]-[C:6](=[C:5]-[c:4](:[c:9]):[cH;D2;+0:1]:[#7;a:2]:[c:3])-[C:8] | 99 | [{"value": 99.0, "product": "C1(CCCC1)=CC=1C=NC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | A solution of 2-chloro-3-cyclopentylidenemethylquinoline (7.6 g, 31.3 mmol) in glacial acetic acid (80 ml) at 60° C. was treated with zinc powder (4.0 g, 62.6 mmol). After stirring at 60° C. for 3 hours, the reaction mixture was cooled and then treated dropwise with aqueous sodium hydroxide solution (2M, 330 ml); the t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CCCC1.c1ccc2ncccc2c1 | Other | [Zn].C(C)(=O)O | 60 | 3 | Clc1nc2ccccc2cc1C=C1CCCC1>[Zn].C(C)(=O)O>C(=C1CCCC1)c1cnc2ccccc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-451cf868ebf34c44bf70d7d52db70570 | COC[C@@H]1CCCN1N.O=C1CCCCC1c1cccnc1>>COC[C@@H]1CCCN1N=C1CCCCC1c1cccnc1 | N1=CC(=CC=C1)C1C(CCCC1)=O.NN1[C@@H](CCC1)COC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>COC[C@H]1N(CCC1)N=C1C(CCCC1)C=1C=NC=CC1 | [CH3:1][O:2][CH2:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:8]1[NH2:9].O=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:8]1[N:9]=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1 | COC[C@@H]1CCCN1N.O=C1CCCCC1c1cccnc1 | COC[C@@H]1CCCN1N=C1CCCCC1c1cccnc1 | null | null | C1(=CC=CC=C1)C.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 8fd42c3afb34fc209a626759948c4bd78aa782c38787b900b74e01ff0893a4bd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | c1cncc(C2CCCCC2=NN2CCCC2)c1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[c:5]:[c:6]:[#7;a:7])-[C:8].[C:9]-[#7:10](-[NH2;D1;+0:11])-[C:12]>>[#7;a:7]:[c:6]:[c:5]-[C:4](-[C:8])-[C;H0;D3;+0:1](=[N;H0;D2;+0:11]-[#7:10](-[C:9])-[C:12])-[C:2]-[C:3] | null | [] | null | null | null | null | A mixture of 2-(pyrid-3-yl)cyclohexanone (20.6 g, 117.6 mmol), [S]-(-)-1-amino-2-(methoxymethyl)pyrrolidine (`SAMP`) (15.4 g, 118 mmol) and p-toluenesulphonic acid (316 mg) was refluxed in toluene (475 ml) for 4 hours. The toluene was removed in vacuo to afford an oil which was dissolved in diethyl ether (340ml) and wa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | C1CCCCC1 | C1CCCCC1 | C1CC[NH]C1.C1CCCCC1.c1ccncc1 | HO- | C1(=CC=CC=C1)C.C(C)OCC | null | null | COC[C@@H]1CCCN1N.O=C1CCCCC1c1cccnc1>C1(=CC=CC=C1)C.C(C)OCC>COC[C@@H]1CCCN1N=C1CCCCC1c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-56f6f1a3df2341c1b4970df530132daa | N#CCOC1CCCCO1.O=C=O.[OH-]>>O=C([O-])COC1CCCCO1 | C(=O)=O.O1C(CCCC1)OCC#N.[OH-].[Na+]>>O1C(CCCC1)OCC(=O)[O-].[Na+] | N#[C:2][CH2:4][O:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][O:11]1.O=C=[O:1].[OH-:3]>>[O:1]=[C:2]([O-:3])[CH2:4][O:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][O:11]1 | N#CCOC1CCCCO1.O=C=O.[OH-] | O=C([O-])COC1CCCCO1 | null | null | C(C)#N.C(C)O | Acylation | OtherReaction | 873a0d78cd9aa5e465d9166ee985e9cb0cf94efa7b5d7be3e2fc98661889cd82 | baebea42b20ea003d124ea699f1f7074b20a77b28c6dbbb9b9796b3b8084375f | C1CCOCC1 | N#[C;H0;D2;+0:1]-[C:2]-[#8:3].O=C=[O;H0;D1;+0:4].[OH-;D0:5]>>[#8:3]-[C:2]-[C;H0;D3;+0:1](-[O-;H0;D1:5])=[O;H0;D1;+0:4] | null | [] | null | null | null | null | To a solution of tetrahydropyran-2-yloxyethanonitrile (6.0 g, 42.49 mmol) in ethanol (15 ml) was added aqueous sodium hydroxide solution (10M, 15 ml). Following the initial exothermic reaction the solution was heated under reflux for 1.5 hours, diluted with ethanol (30 ml) and the pH adjusted to 8 by the addition of ca... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Carbon dioxide | null | null | null | C1CCOCC1 | HO- | C(C)#N.C(C)O | null | null | N#CCOC1CCCCO1.O=C=O.[OH-]>C(C)#N.C(C)O>O=C([O-])COC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-22b7b4af1b9c4b7eba64bdf1c4500578 | CI.O=[Se]1C=Nc2ccccc21>>CN1C[Se](=O)c2ccccc21 | [Se]1(C=NC2=C1C=CC=C2)=O.[Na].CI>>CN1C[Se](C2=C1C=CC=C2)=O | I[CH3:1].[N:2]1=[CH:3][Se:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]21>>[CH3:1][N:2]1[CH2:3][Se:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]21 | CI.O=[Se]1C=Nc2ccccc21 | CN1C[Se](=O)c2ccccc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b227d6210914256cc8ac4a8b605f8e5e7d80ca3e9b075d9f89de6b6f1a107928 | 3b98b4c346cf7ba644e54d3f842b2d58099c5d03aada26bdda3002492023c497 | O=[Se]1CNc2ccccc21 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[#34:3]1-[CH;D2;+0:4]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:5]1-[CH2;D2;+0:4]-[#34:3](=[O;D1;H0:2])-[c:8]:[c:6]-1:[c:7] | null | [] | null | null | 12 | HOUR | 0.01 mol of benzoselenazolinone is introduced into a ground-necked round-bottomed flask containing 0.35 gram (0.015 gram-atom) of sodium dissolved in 50 l cm3 of absolute alcohol. 3.1 cm3 (0.05 mol) of methyl iodide are added dropwise and with stirring. After 12 hours, the solvent is evaporated off. The solid obtained ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[se]cnc2c1 | c1ccc2c(c1)[NH]C[Se]2 | c1ccc2c(c1)[NH]C[Se]2 | I- | O | null | 12 | CI.O=[Se]1C=Nc2ccccc21>O>CN1C[Se](=O)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cac88bd35cc64efb905597bc14f2064b | O=C(O)c1ccccc1.O=[Se]1C=Nc2ccccc21>>O=C(c1ccccc1)c1ccc2c(c1)[Se](=O)C=N2 | [Se]1(C=NC2=C1C=CC=C2)=O.C(C1=CC=CC=C1)(=O)O>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N=C[Se]2=O)C=C1 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[cH:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[Se:15](=[O:16])[CH:17]=[N:18]2>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[Se:15](=[O:16])[CH:17]=[N:18]2 | O=C(O)c1ccccc1.O=[Se]1C=Nc2ccccc21 | O=C(c1ccccc1)c1ccc2c(c1)[Se](=O)C=N2 | null | null | O | C-C Coupling | Friedel-Crafts acylation | 45caf0f3fb674b9f6ab9ad65a07b1d95e5c38969edf207a276d66cc4083af1eb | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(c1ccccc1)c1ccc2c(c1)[Se](=O)C=N2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#34:6]-[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]>>[#34:6]-[c:7]:[c:8]:[c;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:10]:[c:11] | null | [] | 130 | CELSIUS | null | null | 1.98 g (0.01 mol) of benzoselenazolinone, 50 to 60 g of polyphosphoric acid and 1.35 g (0.011 mol) of benzoic acid are introduced into a 100-cm3 round-bottomed flask. The mixture is heated on an oil bath to a temperature of 130° C. for a time T of 3 hours, with stirring. The reaction mixture is then hydrolyzed in 300 c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccc2[se]cnc2c1 | c1ccc2[se]cnc2c1 | c1ccccc1.c1ccc2[se]cnc2c1 | HO- | O | 130 | null | O=C(O)c1ccccc1.O=[Se]1C=Nc2ccccc21>O>O=C(c1ccccc1)c1ccc2c(c1)[Se](=O)C=N2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1d3413e2368040c69f7c5420a1d9dcb4 | CC(=O)Cl.O=[Se]1C=Nc2ccccc21>>CC(=O)c1ccc2c(c1)[Se](=O)C=N2 | C(C)(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-].CN(C=O)C.[Se]1(C=NC2=C1C=CC=C2)=O>>C(C)(=O)C1=CC2=C(N=C[Se]2=O)C=C1 | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[Se:10](=[O:11])[CH:12]=[N:13]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[Se:10](=[O:11])[CH:12]=[N:13]2 | CC(=O)Cl.O=[Se]1C=Nc2ccccc21 | CC(=O)c1ccc2c(c1)[Se](=O)C=N2 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 4785389acd7f91e3bc9199d1a15a404b2c2ab84bcab8df3d52a718cb5229b130 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=[Se]1C=Nc2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#34:4]-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[#34:4]-[c:5]:[c:6]:[c;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | null | null | 12 grams (0.09 mol) of aluminum chloride are introduced into a ground-necked flask. 3.1 cm3 (0.04 mol) of dimethylformamide are added dropwise with stirring. After cooling, two grams (0.01 mol) of benzoselenazolinone are added and the mixture is homogenized. It is heated to 70°-80° C. on an oil bath with stirring, and ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2[se]cnc2c1 | c1ccc2[se]cnc2c1 | c1ccc2[se]cnc2c1 | HCl | null | null | null | CC(=O)Cl.O=[Se]1C=Nc2ccccc21>>CC(=O)c1ccc2c(c1)[Se](=O)C=N2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e84ede7fe7a54153a4005eb838402408 | O=C(Cl)c1cccnc1.O=[Se]1C=Nc2ccccc21>>O=C(c1cccnc1)c1ccc2c(c1)[Se](=O)C=N2 | CN(C=O)C.[Cl-].[Al+3].[Cl-].[Cl-].[Se]1(C=NC2=C1C=CC=C2)=O.Cl.C(C1=CN=CC=C1)(=O)Cl>>C(C1=CN=CC=C1)(=O)C1=CC2=C(N=C[Se]2=O)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1.[cH:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[Se:15](=[O:16])[CH:17]=[N:18]2>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[Se:15](=[O:16])[CH:17]=[N:18]2 | O=C(Cl)c1cccnc1.O=[Se]1C=Nc2ccccc21 | O=C(c1cccnc1)c1ccc2c(c1)[Se](=O)C=N2 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 4785389acd7f91e3bc9199d1a15a404b2c2ab84bcab8df3d52a718cb5229b130 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1cccnc1)c1ccc2c(c1)[Se](=O)C=N2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[#34:8]-[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13]>>[#34:8]-[c:9]:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]):[c:12]:[c:13] | null | [] | 45 | CELSIUS | null | null | 9.9 ml (0.13 mol) of dimethylformamide are introduced dropwise and with stirring into a 250-ml flask containing 61.3 g (0.46 mol) of aluminum chloride, and the flask is fitted with a reflux condenser and heated in an oil bath to a temperature in the region of 45° C. 7.9 g (0.04 mol) of benzoselenazolinone and 10.6 g (0... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2[se]cnc2c1 | c1ccc2[se]cnc2c1 | c1ccncc1.c1ccc2[se]cnc2c1 | HCl | null | 45 | null | O=C(Cl)c1cccnc1.O=[Se]1C=Nc2ccccc21>>O=C(c1cccnc1)c1ccc2c(c1)[Se](=O)C=N2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f45c559759264321ac72a2b37dcee8d3 | ClCCBr.O=[Se]1C=Nc2ccccc21>>O=[Se]1CN(CCCl)c2ccccc21 | C([O-])([O-])=O.[K+].[K+].BrCCCl.[Se]1(C=NC2=C1C=CC=C2)=O>>ClCCN1C[Se](C2=C1C=CC=C2)=O | Br[CH2:5][CH2:6][Cl:7].[O:1]=[Se:2]1[CH:3]=[N:4][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21>>[O:1]=[Se:2]1[CH2:3][N:4]([CH2:5][CH2:6][Cl:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | ClCCBr.O=[Se]1C=Nc2ccccc21 | O=[Se]1CN(CCCl)c2ccccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4ec270cde48ef7f4b95c07219687197c079145130914f0d7f707ba8bc2720964 | 0c6d948e7fba69d7b44cc4c1a32996a54bc4084cd2a810750b998cd8acea70cf | O=[Se]1CNc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3].[O;D1;H0:4]=[#34:5]1-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-1>>[Cl;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[CH2;D2;+0:6]-[#34:5](=[O;D1;H0:4])-[c:10]:[c:8]-1:[c:9] | null | [] | 50 | CELSIUS | 6 | HOUR | 0.06 mol of potassium carbonate and then 0.015 mol of 1-bromo-2-chloroethane are added to a solution of 0.015 mol of benzoselenazolinone in 30 cm3 of dimethylformamide. The mixture is heated to 50° C. with stirring for six hours. The inorganic precipitate is drained and then washed with dimethyl formamide. The DMF is e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Tertiary amine | c1ccc2[se]cnc2c1 | c1ccc2c(c1)[NH]C[Se]2 | c1ccc2c(c1)[NH]C[Se]2 | Br- | CN(C=O)C | 50 | 6 | ClCCBr.O=[Se]1C=Nc2ccccc21>CN(C=O)C>O=[Se]1CN(CCCl)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5d28e8e0676841e598914b8d0977a4cb | C=O.CO.c1ccc2[se]cnc2c1>>O=[Se]1CN(CO)c2ccccc21 | [Se]1C=NC2=C1C=CC=C2.C=O.CO>>OCN1C[Se](C2=C1C=CC=C2)=O | [CH2:5]=[O:6].C[OH:1].[se:2]1[cH:3][n:4][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12>>[O:1]=[Se:2]1[CH2:3][N:4]([CH2:5][OH:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | C=O.CO.c1ccc2[se]cnc2c1 | O=[Se]1CN(CO)c2ccccc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 19d4cc38f6f9402ebc4146fbb9fba0ee156eee3bd5db4da5c3b14d9ca8ec403d | db8042b6982c03215657ad7b146b5c045bd78f1f46dbcbe89b3feae36ec49f93 | O=[Se]1CNc2ccccc21 | C-[OH;D1;+0:1].[CH2;D1;+0:2]=[O;H0;D1;+0:3].[c:4]:[c:5]1:[se;H0;D2;+0:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:[c:9]:1:[c:10]>>[O;H0;D1;+0:1]=[Se;H0;D3;+0:6]1-[CH2;D2;+0:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:2]-[OH;D1;+0:3])-[c:9](:[c:10]):[c:5]-1:[c:4] | null | [] | 40 | CELSIUS | null | null | 2 grams (0.01 mol) of benzoselenazoline, 2 cm3 (0.02 mol) of aqueous formaldehyde solution and 2 cm3 of methanol are introduced into a ground-necked flask. The mixture is brought to reflux two hours. After cooling to 40° C. 20 cm3 of water are added. The mixture is allowed to cool and the product is drained, washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Methanol | Primary alcohol.Tertiary amine | c1ccc2[se]cnc2c1 | c1ccc2c(c1)[NH]C[Se]2 | c1ccc2c(c1)[NH]C[Se]2 | Other | O | 40 | null | C=O.CO.c1ccc2[se]cnc2c1>O>O=[Se]1CN(CO)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7bbf869560ef405cb4745a650ec1ed60 | O=S(Cl)Cl.O=[Se]1CN(CO)c2ccccc21>>O=[Se]1CN(CCl)c2ccccc21 | S(=O)(Cl)Cl.OCN1C[Se](C2=C1C=CC=C2)=O>>ClCN1C[Se](C2=C1C=CC=C2)=O | O=S(Cl)[Cl:6].O[CH2:5][N:4]1[CH2:3][Se:2](=[O:1])[c:12]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2>>[O:1]=[Se:2]1[CH2:3][N:4]([CH2:5][Cl:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | O=S(Cl)Cl.O=[Se]1CN(CO)c2ccccc21 | O=[Se]1CN(CCl)c2ccccc21 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=[Se]1CNc2ccccc21 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[#7:3](-[c:4])-[C:5]-[#34:6]>>[#34:6]-[C:5]-[#7:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 0.55 cm3 of thionyl chloride (0.02 mol) is added dropwise and with stirring into a round-bottom flask containing 0.01 mol of 3-(hydroxymethyl)benzoselenazolinone dissolved in 100 cm3 of chloroform. The mixture is brought to reflux for 2 hours and the chloroform is then evaporated off under reduced pressure. The product... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2c(c1)[NH]C[Se]2 | HCl | C(Cl)(Cl)Cl | null | null | O=S(Cl)Cl.O=[Se]1CN(CO)c2ccccc21>C(Cl)(Cl)Cl>O=[Se]1CN(CCl)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-20f53bdf122d4c0eb79fea6119fe9f55 | O=C(c1ccccc1)c1ccc2c(c1)[Se](=O)C=N2>>Nc1ccc(C(=O)c2ccccc2)cc1[Se][Se]c1cc(C(=O)c2ccccc2)ccc1N | C(C1=CC=CC=C1)(=O)C1=CC2=C(N=C[Se]2=O)C=C1>>NC1=C(C=C(C=C1)C(C1=CC=CC=C1)=O)[Se][Se]C1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)N | [N:1]1=[CH:18][Se:16](=[O:22])[c:15]2[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[cH:14]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]1[Se:16][Se:17][c:18]1[cH:19][c:20]([C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)... | O=C(c1ccccc1)c1ccc2c(c1)[Se](=O)C=N2 | Nc1ccc(C(=O)c2ccccc2)cc1[Se][Se]c1cc(C(=O)c2ccccc2)ccc1N | null | null | [OH-].[Na+] | Aromatic Heterocycle Formation | OtherReaction | db6d1938b530dc0a14294f5599f1eeb1f186a1edffecfed39dac81e65b04a7d3 | dad89fa06c57d60e1d98ab40b1e6a6811fa02d2cbbc5d3090951f54b2de83596 | O=C(c1ccccc1)c1cccc([Se][Se]c2cccc(C(=O)c3ccccc3)c2)c1 | [O;H0;D1;+0:1]=[Se;H0;D3;+0:2]1-[CH;D2;+0:3]=[N;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]-1:[c:8]>>[N;D1;H2:9]-[c:10](:[c:11]):[c;H0;D3;+0:3](-[#34:12]-[Se;H0;D2;+0:2]-[c:7](:[c:8]):[c:5](-[NH2;D1;+0:4]):[c:6]):[c:13]:[c:14]-[C:15](=[O;H0;D1;+0:1])-[c:16] | null | [] | null | null | 2 | HOUR | 1.5 g (0.005 mol) of 6-benzoylbenzoselenazolinone are introduced together with 20 cm3 of 10% sodium hydroxide into a ground-necked flask. The mixture is heated to reflux with stirring for two hours. After cooling, the reaction medium is neutralized. The precipitate is drained, washed with water and dried and the produc... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Primary amine.Primary amine | c1ccc2[se]cnc2c1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | [OH-].[Na+] | null | 2 | O=C(c1ccccc1)c1ccc2c(c1)[Se](=O)C=N2>[OH-].[Na+]>Nc1ccc(C(=O)c2ccccc2)cc1[Se][Se]c1cc(C(=O)c2ccccc2)ccc1N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bcabc6c7750a4ed98f74bdfc2926b4a1 | CC(=O)c1ccc2c(c1)[Se](=O)C=N2>>CC(O)c1ccc2c(c1)[Se](=O)C=N2 | Cl.C(C)(=O)C1=CC2=C(N=C[Se]2=O)C=C1.[OH-].[Na+].[BH4-].[Na+]>>OC(C)C1=CC2=C(N=C[Se]2=O)C=C1 | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[Se:10](=[O:11])[CH:12]=[N:13]2>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[Se:10](=[O:11])[CH:12]=[N:13]2 | CC(=O)c1ccc2c(c1)[Se](=O)C=N2 | CC(O)c1ccc2c(c1)[Se](=O)C=N2 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=[Se]1C=Nc2ccccc21 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 1.2 g (0.005 mol) of 6-acetylbenzoselenazolinone are introduced together with 7.5 cm3 of 3% sodium hydroxide into a ground-necked round-bottom flask cooled in an ice bath. 0.38 g (0.001 mol) of sodium borohydride is then added slowly and with stirring. The solution is stirred at room temperature for 15 hours an the aci... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccc2[se]cnc2c1 | null | null | null | null | CC(=O)c1ccc2c(c1)[Se](=O)C=N2>>CC(O)c1ccc2c(c1)[Se](=O)C=N2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aa19fcdbcf8344d2ba90a7cd4595be1b | CC1(C)CCCC1=O.O=Cc1ccc(Cl)cc1>>CC1(C)CCC(=Cc2ccc(Cl)cc2)C1=O | [OH-].[Na+].CC1(C(CCC1)=O)C.ClC1=CC=C(C=O)C=C1>>CC1(C(C(CC1)=CC1=CC=C(C=C1)Cl)=O)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][C:15]1=[O:16].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[CH:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[C:15]1=[O:16] | CC1(C)CCCC1=O.O=Cc1ccc(Cl)cc1 | CC1(C)CCC(=Cc2ccc(Cl)cc2)C1=O | null | null | C(C)O | C-C Coupling | Aldol condensation | b57e203499046e3d3a056245b7f7f1438c7b88113257c8f40be758e4b3ca4e53 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1CCCC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 59.7 | [{"value": 59.7, "product": "CC1(C(C(CC1)=CC1=CC=C(C=C1)Cl)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 100 ml of a 10% aqueous solution of sodium hydroxide were added to a mixture of 10 g of 2,2-dimethylcyclopentanone and 13.8 g of 4-chlorobenzaldehyde in 100 ml of ethanol at 0° C. After 30 minutes, a thick slurry was filtered off and the solid was washed and then dried. 12.5 g of 2,2-dimethyl-5-(4-chlorobenzylidene)-1-... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | C1CCCC1 | C1CCCC1 | C1CCCC1.c1ccccc1 | HO- | C(C)O | null | 0.5 | CC1(C)CCCC1=O.O=Cc1ccc(Cl)cc1>C(C)O>CC1(C)CCC(=Cc2ccc(Cl)cc2)C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-91ea50635080455580c7511d82a79a21 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc(CBr)cc1>>COC(=O)c1ccc(CBr)cc1 | BrCC1=CC=C(C(=O)O)C=C1.CCCCCC.C[Si](C)(C)C=[N+]=[N-].N#N.C[Si](C)(C)C=[N+]=[N-]>>BrCC1=CC=C(C(=O)OC)C=C1 | C[Si](C)(C)[CH:1]=[N+]=[N-].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[cH:11][cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[cH:11][cH:12]1 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc(CBr)cc1 | COC(=O)c1ccc(CBr)cc1 | null | null | C1(=CC=CC=C1)C.CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | null | [] | null | null | null | null | To a solution of 1.0 eq of 4-(bromomethyl)benzoic acid in 20 ml of methanol and 50 ml of toluene; was added dropwise 2.05 eq of trimethylsilyldiazomethane while stirring at room temperature. The reaction was titrated until a persistant pale yellow color existed from the addition of excess trimethylsilyldiazo- methane. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccccc1 | Other | C1(=CC=CC=C1)C.CO.C(C)(=O)OCC | null | null | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc(CBr)cc1>C1(=CC=CC=C1)C.CO.C(C)(=O)OCC>COC(=O)c1ccc(CBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7a7c4c7f1f2e40e19f403a27972819ca | N[C@H](Cc1ccccc1)C(=O)O.O=Cc1ccccc1>>COC(=O)[C@@H](Cc1ccccc1)N=Cc1ccccc1 | [O-]S(=O)(=O)[O-].[Mg+2].Cl.C(C)N(CC)CC.Cl.N[C@H](CC1=CC=CC=C1)C(=O)O.C(C)N(CC)CC.C(C1=CC=CC=C1)=O.N[C@H](CC1=CC=CC=C1)C(=O)O>>COC([C@H](N=CC1=CC=CC=C1)CC1=CC=CC=C1)=O | [OH:2][C:3](=[O:4])[C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[NH2:13].O=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[N:13]=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | N[C@H](Cc1ccccc1)C(=O)O.O=Cc1ccccc1 | COC(=O)[C@@H](Cc1ccccc1)N=Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc11a6ddbc1e2f5d9e9ceeb667c4fea8c78ad99a0c01ce4328b50c871b1c39b5 | aa63ec4a9e7deeb045e0eda016c44deb889b5d10a9a5bfbc503eeab645a2f45c | C(=NCCc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[C:5]-[C:6](-[N;H0;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[C;D1;H3:11] | null | [] | null | null | 8 | HOUR | To a suspension of 1.0 eq D-phenylalanine HCl (1.6 g, 7.4 mmol) was added 1.0 eq triethylamine to dissolve the D-phenylalanine. To this solution was added 1 equiv. of MgSO4 followed by the addition of 1.0 eq benzaldehyde, the reaction was stirred overnight at room temperature under N2 atmosphere. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Primary amine | Ester.Substituted imine | null | null | c1ccccc1.c1ccccc1 | null | null | null | 8 | N[C@H](Cc1ccccc1)C(=O)O.O=Cc1ccccc1>>COC(=O)[C@@H](Cc1ccccc1)N=Cc1ccccc1 |
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