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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-119328d4f6c144a381d29ff2f0cd48ad | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C.ClC1=CC=C(C=C1)C(C=O)=CN(C)C.C[O-].[Na+].C(#N)CC(=O)N>>C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O | CN(C)[CH:13]=[C:5]([CH:4]=O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[N:1]#[C:2][CH2:3][C:15]([NH2:14])=[O:16]>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14][c:15]1=[O:16] | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 4fb69599b2ad512416349de44ee025f314a8ccdb2c8ad729cdf94ea75cf3109a | 46cf335065eccd013987994a3f086665eb273ac87eb3153099a47e61dd329581 | O=c1ccc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[N;D1;H0:9]#[C:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:1]:[nH;D2;+0:13]:[c;H0;D3;+0... | null | [] | null | null | null | null | To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic add (50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Primary amide | null | null | c1cnccc1 | c1cnccc1.c1ccccc1 | HO- | CO.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>CO.O>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-79fe63c48e194c1993a6d88339084cf5 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)C=1C=CC(NC1)=O | N#C[c:3]1[c:2](=[O:1])[nH:14][cH:13][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:4]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | null | null | OP(=O)(O)O | Miscellaneous | OtherReaction | 145adc421652def73603eb299eace1e2e3a197522b719b6949c0145a4308d11b | 4f08c5adfb6d80fba1093598fc51ce38f180c76537f67052d397b642cb6f3b89 | O=c1ccc(-c2ccccc2)c[nH]1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | 75.6 | [{"value": 75.6, "product": "ClC1=CC=C(C=C1)C=1C=CC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-cyano-5-(4-chlorophenyl)-2-pyridinone (4.6 g) and 85% H3PO4 (60 ml) was heated at reflux for 16 hours. The resulting mixture was cooled to room temperature, poured into ice/water and filtered yielding 3.1 g of 5-(4-chlorophenyl)-2-pyridinone as a yellow solid.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | c1cnccc1 | c1cccnc1 | c1cccnc1.c1ccccc1 | Other | OP(=O)(O)O | null | null | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>OP(=O)(O)O>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c9ccf1c64cef45c9a38e8ebb2cfb10e4 | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | [Cl-].[NH4+].[H-].[Na+].N1C(C=CC=C1)=O.CCCCCC.C(C)(=O)OCC.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=CC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[CH2:9]([CH3:10])[CH2:15][CH2:14][CH2:12][CH3:11].[nH:6]1[cH:7][cH:8][cH:16][cH:17][c:18]1=[O:19].[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][cH:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-] | CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | c16e53991381708a0d74f5092b5e25b0353184189763eaae006dd565c1174ab9 | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ccc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10].[Cl-;H0;D0:11].[O;D1;H0:12]=[c:13]1:[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:6]2:[cH;D2;+0:5]:[cH;D2;+0:... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 200 mg) in dry DMF (50 ml) at 0° C. was added the preceding pyridinone and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne dropwise. The resulting mixture was kept at 0° C. during one half hour and poured into satura... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2125b916997c4e6d96420da536d3a807 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>>O=c1ccc2c(Cl)cccc2[nH]1 | ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>ClC1=C2C=CC(NC2=CC=C1)=O | c1ccc([CH:4]=[CH:3][C:2](=[O:1])[NH:12][c:11]2[cH:5][cH:8][c:6]([Cl:7])[cH:9][cH:10]2)cc1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]2[nH:12]1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | O=c1ccc2c(Cl)cccc2[nH]1 | null | null | ClC1=CC=CC=C1 | Reduction | OtherReaction | ebe7e954f82f1e726cf9b7a8863216fec31733c3d8bfbb1cc71c49312cec65ac | 10d6d5b071f1d84b20b253ce9eadaed211c373c6ee607356078792f13319351a | O=c1ccc2ccccc2[nH]1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-c2:c:c:c:c:c:2):[c:11]:[cH;D2;+0:12]:1>>[Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:12]:[c:11]:[c:5]2:[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+... | null | [] | 125 | CELSIUS | 3 | HOUR | To a mixture of N-(4-chlorophenyl)cinnamamide (8.3 g), and chlorobenzene (60 ml) was added portionwise aluminum chloride (21.4 g) trader nitrogen at room temperature and the reaction mixture was slowly warmed up to 125° C. and kept at that temperature for 3 hours. The reaction mixture was cooled down and poured over 40... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccc2ccccc2n1 | c1ccc2ccccc2n1 | Other | ClC1=CC=CC=C1 | 125 | 3 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>ClC1=CC=CC=C1>O=c1ccc2c(Cl)cccc2[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d9ff793142c547c8aee4d9d896a93b93 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>>CCC#CCn1c(=O)ccc2c(Cl)cccc21 | [Cl-].[NH4+].N1C(C=CC2=CC=CC=C12)=O.[H-].[Na+].BrCC#CCC>>ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[nH:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[cH:12][cH:14][cH:15][cH:16][c:17]12.[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-] | CCC#CCn1c(=O)ccc2c(Cl)cccc21 | null | null | CN(C)C=O.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a61336fe7a89ec0981a525297b55629e44e830f13f91df56a44bf01390d8c69d | dbda6588fa29cbbc0e3c3f601e69924b300990bdcc56b8cec0535d1258039346 | O=c1ccc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[Cl-;H0;D0:5].[O;D1;H0:6]=[c:7]1:[c:8]:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[c:15]:2:[nH;D2;+0:16]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:16]1:[c:15]2:[c:14]:[c:13]:[c:12]:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:5]):[c:10]:2:[c:9]:[c:8]:[c:7]:1=[O;D1;H0:6] | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and po... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccc2ccccc2n1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | CN(C)C=O.CCCCCC | 0 | null | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>CN(C)C=O.CCCCCC>CCC#CCn1c(=O)ccc2c(Cl)cccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ced4f53fd68e4069b40e335eb3df94b0 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | [Cl-].[NH4+].ClC1=CC=C(C=C1)C(C=O)=CN(C)C.NC(=O)N.Cl>>ClC1=CC=C(C=C1)C=1C=NC(NC1)=O | CN(C)[CH:4]=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH:13]=O.[O:1]=[C:2]([NH2:3])[NH2:14]>>[O:1]=[c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O | O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | 0e1bb7c6fc2fa2fbd0239b648ae136ef123b13ddeb9947c50b8f38d453d7d183 | 55a949c5abf218b0e7fd0015b81e86fb975fa441e5ac6bd395c3346bb38599f7 | O=c1ncc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[O;D1;H0:12]>>[O;D1;H0:12]=[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:3]:[nH;D2;+0:9]:1 | 29.7 | [{"value": 29.7, "product": "ClC1=CC=C(C=C1)C=1C=NC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Urea | null | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>C(C)O.O>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0cdfb3a6a39e4aada49cd2cfa61b5f7c | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | [Cl-].[NH4+].CCCCCC.[H-].[Na+].N1C(C=CC=C1)=O.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].C[CH2:15][CH2:14][CH2:12][CH2:11][CH3:10].[nH:6]1[cH:7][cH:8][cH:16][cH:9][c:18]1=[O:19].[Cl-:13].[NH4+:17]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][n:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+] | CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | b4467fdd65493649554b053844b88f7aedac75ecb5e83a2819a9163270cc6b1f | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ncc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].C-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH3;D1;+0:9].[Cl-;H0;D0:10].[NH4+;D0:11].[O;D1;H0:12]=[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:14]2... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and pour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a068a7407087432ba77b2eb060642cca | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1C=CC(NN1)=O.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=S | O=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:1])(S2)S3>>[S:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | e0da8be0c0e31372bc487fca4d998b8539b7ff5b84df07e1a6200efd3593e0bb | 13be3f637e1e22872d741944f46b7fcc1954fe982a3a8a0f7825545d455ab147 | S=c1ccc(-c2ccccc2)n[nH]1 | O=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:7])(-S-2)-S-3>>[S;H0;D1;+0:7]=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 187.1 | [{"value": 187.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thiocarbonyl | c1cccnn1.S1P2SP3SP1SP(S2)S3 | c1cccnn1 | c1cccnn1.c1ccccc1 | Other | N1=CC=CC=C1 | null | null | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5b77163772334a28b4e039cda3410b19 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)NN)C=C1.ClCC(=O)Cl>>ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O | [NH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl | O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | null | null | O1CCOCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9] | null | [] | null | null | null | null | To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as whit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1 | HCl | O1CCOCC1 | null | null | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>O1CCOCC1>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3b6843caea374b8d88ee79ad8d8db495 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>>O=C1NN=C(c2ccc(Cl)cc2)CS1 | BrCC(=O)C1=CC=C(C=C1)Cl.COC(=S)NN>>ClC1=CC=C(C=C1)C1=NNC(SC1)=O | C[O:1][C:2]([NH:3][NH2:4])=[S:14].O=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13]Br>>[O:1]=[C:2]1[NH:3][N:4]=[C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:13][S:14]1 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1 | O=C1NN=C(c2ccc(Cl)cc2)CS1 | null | null | C(C)#N | Acylation | OtherReaction | a0815ff887854434f061e02bb59e65917f2f792eefe3f407e6f67a241e834044 | b7ddc8c969600ae9a9b2d12841c66a24307741bcbfc0810c56e58eb7d0e4892d | O=C1NN=C(c2ccccc2)CS1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].C-[O;H0;D2;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[#7:9]-[NH2;D1;+0:10]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[#7:9]-[N;H0;D2;+0:10]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-1 | 48.4 | [{"value": 48.4, "product": "ClC1=CC=C(C=C1)C1=NNC(SC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Ketone.Ether.Thioamide | Hydrazone amide.Monosulfide | null | C1=NNCSC1 | C1=NNCSC1.c1ccccc1 | HBr | C(C)#N | null | null | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>C(C)#N>O=C1NN=C(c2ccc(Cl)cc2)CS1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1123e2cb6514274b6960618c4f635b5 | O=C(O)CCC(=O)c1cccc(Cl)c1>>O=C(O)CCCc1cccc(Cl)c1 | ClC=1C=C(C(=O)CCC(=O)O)C=CC1.[OH-].[K+].NN>>ClC=1C=C(C=CC1)CCCC(=O)O | O=[C:6]([CH2:5][CH2:4][C:2](=[O:1])[OH:3])[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | O=C(O)CCCc1cccc(Cl)c1 | null | null | C(COCCO)O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9] | 90.8 | [{"value": 90.8, "product": "ClC=1C=C(C=CC1)CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 300 ml round-bottomed flask equipped with magnetic stirrer and reflux condenser was charged 23.7 g of 87% potassium hydroxide and 150 ml of diethyleneglycol, With stirring, 23 g of 3-(3-chlorobenzoyl)-propionic acid was added followed by 24 g of 85% hydrazine. The mixture was heated to reflux for 2 hours when 50 m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | C(COCCO)O | null | null | O=C(O)CCC(=O)c1cccc(Cl)c1>C(COCCO)O>O=C(O)CCCc1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0e26495fba2b4cde9bc3510578dfcbbf | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | ClC1=CC=C(C=O)C=C1.C(CCC(=O)C)(=O)O.N1CCCCC1.C1(=CC=CC=C1)C>>ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH3:8].O=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH:8]=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1 | O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | null | null | O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 44 | [{"value": 44.0, "product": "ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>O>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-275e8400c15942e28e2a52018fda7f14 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>>COc1ccc(C(=O)O)cc1[N+](=O)[O-] | [N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C.[OH-].[K+]>>[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC | C[c:10]1[c:6]([C:7](=[O:8])[O-:9])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-] | COc1ccc(C(=O)O)cc1[N+](=O)[O-] | null | null | O1CCCC1 | Miscellaneous | OtherReaction | ec2bcf645eed3485ae21dd491bac7887e7ecc8e6727067de36c08c87eaa3e98c | d003579d88c8e6390ed4fac608b8ce68d334559ff02e2f3d9c9936750b60a874 | c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]):[c:9]>>[#7;+:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7]):[c:9] | 76.6 | [{"value": 76.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1 | null | 12 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>O1CCCC1>COc1ccc(C(=O)O)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb63de3fd8b24647933622c8df3a84d0 | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1ccccc1OCc1ccccc1>>Oc1cccc(C[C@H]2CO2)c1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=CC=C1)O.C([O-])([O-])=O.[K+].[K+].C([C@@H]1CO1)OS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-]>>C([C@H]1CO1)C=1C(=C(C=CC1)O)OCC1=CC=CC=C1 | O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:7][C@@H:8]2[CH2:9][O:10]2)c1.[OH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][C@H:8]2[CH2:9][O:10]2)[c:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1ccccc1OCc1ccccc1 | Oc1cccc(C[C@H]2CO2)c1OCc1ccccc1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | d85bd53c3531f4545f1b83e87e40f622e30342624aa88fd54162f4caae93acc5 | 5502ac73153b92df99e08d1f611cc54b4d1dc79aa8af4606001f3dd91f190740 | c1ccc(COc2ccccc2C[C@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:9]:[c:10] | null | [] | null | null | null | null | A mixture of 2-benzyloxyphenol (900 mg, 4.5 mMol) and potassium carbonate (1.87 g, 13.5 mMol) in acetone (45 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (1.0 g, 4.5 mMol) was added and the reaction mixture was heated under reflux for 23 hours. After cooling, the reaction mixture was f... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Sulfonate | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.C1CO1.c1ccccc1 | HO- | CC(=O)C | null | null | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1ccccc1OCc1ccccc1>CC(=O)C>Oc1cccc(C[C@H]2CO2)c1OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7a6d0a34d26147ccbbd1b4a703979302 | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1cccc(OCc2ccccc2)c1>>Oc1cccc(OCc2ccccc2)c1C[C@H]1CO1 | C(C1=CC=CC=C1)OC=1C=C(C=CC1)O.C([O-])([O-])=O.[K+].[K+].C([C@@H]1CO1)OS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-]>>C([C@H]1CO1)C1=C(C=CC=C1OCC1=CC=CC=C1)O | O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:16][C@@H:17]2[CH2:18][O:19]2)c1.[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]1[CH2:16][C@H:17]1[CH2:18][O:19]1 | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1cccc(OCc2ccccc2)c1 | Oc1cccc(OCc2ccccc2)c1C[C@H]1CO1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | d85bd53c3531f4545f1b83e87e40f622e30342624aa88fd54162f4caae93acc5 | 5502ac73153b92df99e08d1f611cc54b4d1dc79aa8af4606001f3dd91f190740 | c1ccc(COc2ccccc2C[C@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | null | null | A mixture of 3-benzyloxyphenol (900 mg, 4.5 mMol) and potassium carbonate (1.87 g, 13.5 mMol) in acetone (45 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (1.0 g, 4.5 mMol) was added and the reaction mixture was heated under reflux for 23 hours. After cooling the reaction mixture was fi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Sulfonate | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CO1 | HO- | CC(=O)C | null | null | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1cccc(OCc2ccccc2)c1>CC(=O)C>Oc1cccc(OCc2ccccc2)c1C[C@H]1CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f128083fd7554ead9f40eeecd8845c28 | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1ccc(OCc2ccccc2)cc1>>Oc1ccc(OCc2ccccc2)cc1C[C@H]1CO1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+].C([C@@H]1CO1)OS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-]>>C([C@H]1CO1)C1=C(C=CC(=C1)OCC1=CC=CC=C1)O | O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:16][C@@H:17]2[CH2:18][O:19]2)c1.[OH:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]1[CH2:16][C@H:17]1[CH2:18][O:19]1 | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1ccc(OCc2ccccc2)cc1 | Oc1ccc(OCc2ccccc2)cc1C[C@H]1CO1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | d85bd53c3531f4545f1b83e87e40f622e30342624aa88fd54162f4caae93acc5 | 5502ac73153b92df99e08d1f611cc54b4d1dc79aa8af4606001f3dd91f190740 | c1ccc(COc2cccc(C[C@H]3CO3)c2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[O;D1;H1:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H1:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:9]:[c:10] | null | [] | null | null | null | null | A mixture of 4-benzyloxyphenol (2.0 g, 10 mMol) and potassium carbonate (4.14 g, 30 mMol) in acetone (50 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (2.23 g, 10 mMol) was added and the reaction mixture was heated under reflux for 18 hours. After cooling, the reaction mixture was filte... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Sulfonate | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CO1 | HO- | CC(=O)C | null | null | O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1.Oc1ccc(OCc2ccccc2)cc1>CC(=O)C>Oc1ccc(OCc2ccccc2)cc1C[C@H]1CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d01bdcbca7ae4670b375df3584280165 | COC(=O)c1cc(OCc2ccccc2)ccc1O>>OCc1cc(OCc2ccccc2)ccc1O | [H-].[Al+3].[Li+].[H-].[H-].[H-].COC(C1=C(C=CC(=C1)OCC1=CC=CC=C1)O)=O>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)O)CO | CO[C:2](=[O:1])[c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[OH:17]>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[OH:17] | COC(=O)c1cc(OCc2ccccc2)ccc1O | OCc1cc(OCc2ccccc2)ccc1O | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 20 | MINUTE | Lithium aluminium hydride (0.235 g, 6.2 mMol) was suspended in tetrahydrofuran (25 ml) and cooled to 0° C. 5-Benzyloxy-2-hydroxy benzoic acid methyl ester (2 g, 7.75 mMol) in tetrahydrofuran (10 ml) was added dropwise, via cannula. The mixture was warmed to room temperature and stirred for 20 minutes. The reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | 0 | 0.333333 | COC(=O)c1cc(OCc2ccccc2)ccc1O>O1CCCC1>OCc1cc(OCc2ccccc2)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-86f5e49c8e57407dadc506848462b455 | COC(=O)COc1ccc(C[C@@H](C)N)cc1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2OCc2ccccc2)cc1>>COC(=O)COc1ccc(CC(C)NCC(O)COc2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)cc1 | C(C1=CC=CC=C1)OC=1C=C(OC[C@@H]2CO2)C=CC1OCC1=CC=CC=C1.COC(COC1=CC=C(C=C1)C[C@@H](C)N)=O>>C(C1=CC=CC=C1)OC=1C=C(OCC(CNC(CC2=CC=C(OCC(=O)OC)C=C2)C)O)C=CC1OCC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][C@@H:12]([CH3:13])[NH2:14])[cH:42][cH:43]1.[CH2:15]1[C@@H:16]([CH2:18][O:19][c:20]2[cH:21][cH:22][c:23]([O:24][CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[c:32]([O:33][CH2:34][c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[cH:41]2)[O:17]1>>[CH3... | COC(=O)COc1ccc(C[C@@H](C)N)cc1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2OCc2ccccc2)cc1 | COC(=O)COc1ccc(CC(C)NCC(O)COc2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(CCNCCCOc2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)cc1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C@@H;D3;+0:7](-[NH2;D1;+0:8])-[C:9]-[c:10]>>[#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:8]-[CH;D3;+0:7](-[C;D1;H3:6])-[C:9]-[c:10] | null | [] | null | null | null | null | The title compound was prepared from (S)-3-(3,4-dibenzyloxyphenoxy)-1,2-epoxypropane and (R)-4-(2-aminopropyl)phenoxyacetic acid methyl ester according to the method described in Procedure 13.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | COC(=O)COc1ccc(C[C@@H](C)N)cc1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2OCc2ccccc2)cc1>>COC(=O)COc1ccc(CC(C)NCC(O)COc2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a3c93df638364213adea34d2adfb06d5 | COc1ccc(C[C@@H](C)N)cc1OC>>C[C@@H](N)Cc1ccc(O)c(O)c1 | COC=1C=C(C=CC1OC)C[C@@H](C)N.Br>>Br.OC=1C=C(C=CC1O)C[C@@H](C)N | C[O:10][c:9]1[cH:8][cH:7][c:6]([CH2:5][C@@H:3]([CH3:2])[NH2:4])[cH:13][c:11]1[O:12]C>>[CH3:2][C@@H:3]([NH2:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([OH:12])[cH:13]1 | COc1ccc(C[C@@H](C)N)cc1OC | C[C@@H](N)Cc1ccc(O)c(O)c1 | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | null | null | A solution of (R)-3-(3,4-dimethoxyphenyl)-2-propylamine hydrochloride1 (500 mg, 2.15 mMol) in hydrogen bromide (48%, 5 ml) was stirred at 100° C. under an argon atmosphere for 20 hours. After cooling, the solvent was evaporated and the residue was dried giving the title compound.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | null | null | null | COc1ccc(C[C@@H](C)N)cc1OC>>C[C@@H](N)Cc1ccc(O)c(O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-15507b7830194c87ab4d8306a193e36d | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@@H](CNC(=O)OC(C)(C)C)c1ccc(O)c(O)c1>>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc2O1 | C([O-])([O-])=O.[K+].[K+].BrC(C(=O)OCC)(C(=O)OCC)Br.OC=1C=C(C=CC1O)[C@H](CNC(OC(C)(C)C)=O)C>>C(C)(C)(C)OC(=O)N[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C | Br[C:6](Br)([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11].[OH:12][c:13]1[cH:14][cH:15][c:16]([C@H:18]([CH2:17][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH3:19])[cH:28][c:29]1[OH:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9][CH2:10][CH3:11])[O:12][c:13]2[cH:14... | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@@H](CNC(=O)OC(C)(C)C)c1ccc(O)c(O)c1 | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc2O1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | de476b63dc919a8f3e80de3a61a89ffd2470b06a92be1eaaaddf4be8e0f44b66 | a86729b0879fcb1fe9a0b2a5ed2b34c3c74bcee429454486f23c56ed9ecb94bf | c1ccc2c(c1)OCO2 | Br-[C;H0;D4;+0:1](-Br)(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[C;D1;H3:10]-[C@@H;D3;+0:11](-[CH2;D2;+0:12]-[NH;D2;+0:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20])-[c;H0;D3;+0:21]1:[c:22]:[c:23]:[c:24](-[OH;D1;+0:25]):[c:26](-[OH;D1;+0:27]):[c:28]:1>>[C... | null | [] | 60 | CELSIUS | 1 | HOUR | A solution of (R)-2-(3,4-dihydroxyphenyl)propylcarbamic acid, t-butyl ester. (1.07 g, 4 mMol) in acetone (25 ml) containing potassium carbonate (3 equiv, 1.66 g, 12 mMol) was stirred at 60° C. under an argon atmosphere for 1 hour. After cooling to ambient temperature, a solution of diethyl dibromomalonate (1.27 g, 4 mM... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Carbamic ester.Ester.Ester.Aromatic alcohol.Aromatic alcohol | Carbamic ester.Ester.Ester.Ether.Ether | c1ccccc1 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HBr | CC(=O)C | 60 | 1 | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@@H](CNC(=O)OC(C)(C)C)c1ccc(O)c(O)c1>CC(=O)C>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc2O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bd1ea3526e084bb093238986ab53097a | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc2O1>>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N)cc2O1 | C(C)OC(=O)C1(OC2=C(O1)C=CC(=C2)C[C@@H](C)NC(=O)OC(C)(C)C)C(=O)OCC.C(C)OCC.Cl>>Cl.N[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C | CC(C)(C)OC(=O)[NH:20][C@@H:18]([CH2:17][c:16]1[cH:15][cH:14][c:13]2[c:22]([cH:21]1)[O:23][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([C:7](=[O:8])[O:9][CH2:10][CH3:11])[O:12]2)[CH3:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9][CH2:10][CH3:11])[O:12][c:13]2[cH:14][cH:15][c:16]([CH2:17][C@@H:18]([CH3:19])[NH... | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc2O1 | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N)cc2O1 | null | null | C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2c(c1)OCO2 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4]>>[C:3]-[C:2](-[C;D1;H3:4])-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of (R)-5-[N-(t-butyloxycarbonyl)-2-aminopropyl]-1,3-benzodioxole-2,2-dicarboxylic acid diethyl ester (3.0 g, 7 mMol) in ethyl acetate (40 ml) and hydrogen chloride solution in diethyl ether (1M, 56 ml, 56 mMol) was stirred at ambient temperature under an argon atmosphere for 48 hours. The solvent was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)OCO2 | HO- | C(C)(=O)OCC | null | null | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc2O1>C(C)(=O)OCC>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N)cc2O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5e96551488e842a0ae7a5944f04ecff0 | CCOP(=O)(COS(=O)(=O)c1ccc(Cl)cc1)OCC.O=C(O)NCCc1ccc(O)cc1>>CCOP(=O)(COc1ccc(CCNC(=O)OC(C)(C)C)cc1)OCC | C(C)OP(OCC)(=O)COS(=O)(=O)C1=CC=C(C=C1)Cl.[H-].[Na+].OC1=CC=C(C=C1)CCNC(O)=O.O>>C(C)(C)(C)OC(=O)NCCC1=CC=C(OCP(OCC)(OCC)=O)C=C1 | O=S(=O)(O[CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:24][CH2:25][CH3:26])c1c[cH:19][c:18](Cl)[cH:20][cH:21]1.[OH:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][NH:14][C:15](=[O:16])[OH:17])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][... | CCOP(=O)(COS(=O)(=O)c1ccc(Cl)cc1)OCC.O=C(O)NCCc1ccc(O)cc1 | CCOP(=O)(COc1ccc(CCNC(=O)OC(C)(C)C)cc1)OCC | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 7fbeef5523bed283442829ff1014a5b4867a48e8acae5f082f9dcee58e2d0312 | ce8f0489d71ba4094431209bdeaacc87eb9195031b5a70c3e3935924bafae50e | c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:c:c(-S(=O)(=O)-O-[CH2;D2;+0:3]-[#15:4](-[#8:5])(-[#8:6])=[O;D1;H0:7]):[cH;D2;+0:8]:[cH;D2;+0:9]:1.[C:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14].[OH;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[#8:5]-[#15:4](-[#8:6])(=[O;D1;H0:7])-[CH2;D2;+0:3]-[O;H0;D2;+0:15]-[c:16](:[c:17]):[c:18].[C:10]-[#7... | null | [] | null | null | null | null | A solution of 2-(4-hydroxyphenyl)ethylcarbamic acid, t-butyl ester1 (4.0 g, 16.9 mMol) in dry DMSO (37.5 ml) was cooled in an ice-bath and treated with sodium hydride (80% in mineral oil 0.557 g, 1.1 equiv) with stirring under argon according to the method described by Cornforth2. When effervescence ceased a solution o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic acid.Aromatic alcohol.Sulfonate | Carbamic ester.Ether.Ether.Boc | c1ccccc1 | null | c1ccccc1 | Other | CS(=O)C | null | null | CCOP(=O)(COS(=O)(=O)c1ccc(Cl)cc1)OCC.O=C(O)NCCc1ccc(O)cc1>CS(=O)C>CCOP(=O)(COc1ccc(CCNC(=O)OC(C)(C)C)cc1)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-37aef411031a48079180fe910acb60fa | CCOP(=O)(COc1ccc(CCNC(=O)OC(C)(C)C)cc1)OCC>>CCOP(=O)(COc1ccc(CCN)cc1)OCC | C(C)(C)(C)OC(=O)NCCC1=CC=C(OCP(OCC)(OCC)=O)C=C1>>NCCC1=CC=C(OCP(OCC)(OCC)=O)C=C1 | CC(C)(C)OC(=O)[NH:14][CH2:13][CH2:12][c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:17][CH2:18][CH3:19])[cH:16][cH:15]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][NH2:14])[cH:15][cH:16]1)[O:17][CH2:18][CH3:19] | CCOP(=O)(COc1ccc(CCNC(=O)OC(C)(C)C)cc1)OCC | CCOP(=O)(COc1ccc(CCN)cc1)OCC | null | null | C(Cl)Cl.FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | 4-(2-t-Butoxycarbonylaminoethyl)phenoxymethylphosphonic acid, diethyl ester (2.856 g, 9.95 mMol) in methylene chloride (300 ml) and trifluoracetic acid (16 ml) was stirred at room temperature for 5 h. The solution was concentrated under reduced pressure and product dried under in vacuo. The trifluoacetic acid salt was ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl.FC(C(=O)O)(F)F | null | null | CCOP(=O)(COc1ccc(CCNC(=O)OC(C)(C)C)cc1)OCC>C(Cl)Cl.FC(C(=O)O)(F)F>CCOP(=O)(COc1ccc(CCN)cc1)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1f90df0f79374e948d81d55edfef11d9 | COC(=O)CBr.C[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>>COC(=O)COc1ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc1 | C([O-])([O-])=O.[K+].[K+].OC1=CC=C(C=C1)C[C@@H](C)NC(OC(C)(C)C)=O.BrCC(=O)OC>>C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=C(OCC(=O)OC)C=C1)C | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][C@@H:12]([CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][C@@H:12]([CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3... | COC(=O)CBr.C[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C | COC(=O)COc1ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | Potassium carbonate (1.95 g, 14.2 mMol) was added to a solution of (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester (2.96 g, 11.8 mMol) in acetone (50 ml) at room temperature under argon. Methyl bromoacetate (1.81 g, 11.8 mMol) was added dropwise and the reaction mixture was heated at reflux for 3 hour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | COC(=O)CBr.C[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>CC(=O)C>COC(=O)COc1ccc(C[C@@H](C)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-925d657bfda44fcdaa2c7275376e5fb5 | C=CCOCc1ccccc1.O=[PH2]O>>O=[PH](O)CCCOCc1ccccc1 | C(C=C)OCC1=CC=CC=C1.[PH2](O)=O>>C(C1=CC=CC=C1)OCCCP(O)=O | [CH2:4]=[CH:5][CH2:6][O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[PH2:2][OH:3]>>[O:1]=[PH:2]([OH:3])[CH2:4][CH2:5][CH2:6][O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | C=CCOCc1ccccc1.O=[PH2]O | O=[PH](O)CCCOCc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | c1ccccc1 | [#8:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[O;D1;H0:5]=[PH2;D2;+0:6]-[O;D1;H1:7]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[PH;D3;+0:6](=[O;D1;H0:5])-[O;D1;H1:7] | null | [] | null | null | null | null | The title compound was prepared from allylbenzyl ether and 50% aqueous phosphinic acid by an analogous procedure to that described in J. Inorg. Nucl. Chem., 1965, 27, 697.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | c1ccccc1 | null | null | null | null | C=CCOCc1ccccc1.O=[PH2]O>>O=[PH](O)CCCOCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5e782fbe5d444dfdbc8456bc63b99809 | C=O.CCCCO[PH](=O)CCCOCc1ccccc1>>CCCCOP(=O)(CO)CCCOCc1ccccc1 | C(CCC)OP(=O)CCCOCC1=CC=CC=C1.C=O>>C(C1=CC=CC=C1)OCCCP(OCCCC)(=O)CO | [CH2:8]=[O:9].[CH3:1][CH2:2][CH2:3][CH2:4][O:5][PH:6](=[O:7])[CH2:10][CH2:11][CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6](=[O:7])([CH2:8][OH:9])[CH2:10][CH2:11][CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=O.CCCCO[PH](=O)CCCOCc1ccccc1 | CCCCOP(=O)(CO)CCCOCc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | ff9e019412f5fb147910daaf4ee10ff7abac3966a22d93efa93ff9552cbbbf9e | a07b6e0bbdb5ea0627df192b2885de7d34cb5e55531d8d5102717495a910d9a6 | c1ccccc1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[C:4]-[PH;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8]>>[C:3]-[C:4]-[P;H0;D4;+0:5](=[O;D1;H0:6])(-[#8:7]-[C:8])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | The title compound was prepared from 3-benzyloxypropylphosphinic acid n-butyl ester and paraformaldehyde according to the method described in Procedure 31. Purification by chromatography, eluting with dichloromethane containing 5% methanol, gave an oil.
Conditions: See reaction.notes.procedure_details.
Workup: Purifica... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | null | null | c1ccccc1 | null | null | null | null | C=O.CCCCO[PH](=O)CCCOCc1ccccc1>>CCCCOP(=O)(CO)CCCOCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7fbc646e6f24341bd3baed08edf1bc8 | CC(C)(C)OC(=O)NCCc1ccc(O)cc1.CCCCOP(=O)(CCCOCc1ccccc1)COS(=O)(=O)c1ccc(Cl)cc1>>CCCCOP(=O)(CCCOCc1ccccc1)COc1ccc(CCNC(=O)OC(C)(C)C)cc1 | C(C1=CC=CC=C1)OCCCP(OCCCC)(=O)COS(=O)(=O)C1=CC=C(C=C1)Cl.OC1=CC=C(C=C1)CCNC(OC(C)(C)C)=O>>C(C)(C)(C)OC(=O)NCCC1=CC=C(OCP(OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1 | [OH:20][c:21]1[cH:22][cH:23][c:24]([CH2:25][CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35][cH:36]1.O=S(=O)(O[CH2:19][P:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])(=[O:7])[CH2:8][CH2:9][CH2:10][O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)c1ccc(Cl)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:... | CC(C)(C)OC(=O)NCCc1ccc(O)cc1.CCCCOP(=O)(CCCOCc1ccccc1)COS(=O)(=O)c1ccc(Cl)cc1 | CCCCOP(=O)(CCCOCc1ccccc1)COc1ccc(CCNC(=O)OC(C)(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4a0fabf60c721d09151620f81fa665b80305ceb254e48798548a02ab5f5e8fbd | 950dec716ae7be3d224d7e6483bf59e5d7854c2812a5092d632124a3b7567300 | O=[PH](CCCOCc1ccccc1)COc1ccccc1 | Cl-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[#15:2](-[#8:3])(-[C:4])=[O;D1;H0:5]):c:c:1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:3]-[#15:2](-[C:4])(=[O;D1;H0:5])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | The title compound was prepared from 3-benzyloxypropyl-(4-chlorobenzenesulfonyloxymethyl)phosphinic acid, n-butyl ester and 2-(4-hydroxyphenyl)ethylcarbamic acid, t-butyl ester according to the procedure described in Procedure 24. The crude product was purified by chromatography, eluting with dichloromethane containing... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)OC(=O)NCCc1ccc(O)cc1.CCCCOP(=O)(CCCOCc1ccccc1)COS(=O)(=O)c1ccc(Cl)cc1>>CCCCOP(=O)(CCCOCc1ccccc1)COc1ccc(CCNC(=O)OC(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dc474815e92e4518a4bce138d4d23348 | CCCCOP(=O)(CCCOCc1ccccc1)COS(=O)(=O)c1ccc(Cl)cc1.C[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>>CCCCO[P@](=O)(CCCOCc1ccccc1)COc1ccc(CC(C)NC(=O)OC(C)(C)C)cc1 | C(C1=CC=CC=C1)OCCCP(OCCCC)(=O)COS(=O)(=O)C1=CC=C(C=C1)Cl.OC1=CC=C(C=C1)C[C@@H](C)NC(OC(C)(C)C)=O>>C(C)(C)(C)OC(=O)NC(CC1=CC=C(OC[P@@](OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1)C | O=S(=O)(O[CH2:19][P:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])(=[O:7])[CH2:8][CH2:9][CH2:10][O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)c1ccc(Cl)cc1.[OH:20][c:21]1[cH:22][cH:23][c:24]([CH2:25][C@@H:26]([CH3:27])[NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[cH:36][cH:37]1>>[CH3:1][CH2:2][CH2:3... | CCCCOP(=O)(CCCOCc1ccccc1)COS(=O)(=O)c1ccc(Cl)cc1.C[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C | CCCCO[P@](=O)(CCCOCc1ccccc1)COc1ccc(CC(C)NC(=O)OC(C)(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4a0fabf60c721d09151620f81fa665b80305ceb254e48798548a02ab5f5e8fbd | 950dec716ae7be3d224d7e6483bf59e5d7854c2812a5092d632124a3b7567300 | O=[PH](CCCOCc1ccccc1)COc1ccccc1 | Cl-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[P;H0;D4;+0:2](=[O;D1;H0:3])(-[#8:4]-[C:5])-[C:6]-[C:7]):c:c:1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[#8:4]-[P@;H0;D4;+0:2](=[O;D1;H0:3])(-[C:6]-[C:7])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The title compound was prepared from 3-benzyloxypropyl-(4-chlorobenzenesulfonyloxymethyl)phosphinic acid, n-butyl ester and (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester according to the method described in Procedure 24. The crude product was purified by chromatography, eluting with dichloromethane ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | CCCCOP(=O)(CCCOCc1ccccc1)COS(=O)(=O)c1ccc(Cl)cc1.C[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>>CCCCO[P@](=O)(CCCOCc1ccccc1)COc1ccc(CC(C)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7f531c27f471483498c3ba9ea0b700cd | O=[PH](O)C1CCCCC1>>CCCCO[PH](=O)C1CCCCC1 | C1(CCCCC1)P(O)=O>>C1(CCCCC1)P(OCCCC)=O | [CH2:1]1[CH2:9][CH:8]([PH:6]([OH:5])=[O:7])[CH2:13][CH2:12][CH2:11]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][PH:6](=[O:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | O=[PH](O)C1CCCCC1 | CCCCO[PH](=O)C1CCCCC1 | null | null | C(CCC)O | Miscellaneous | OtherReaction | 497ed6fa2fecc89bd99211bb234d91811e03f385203fb438fe023970267815cc | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1CCCCC1 | [O;D1;H0:1]=[#15:2](-[OH;D1;+0:3])-[C:4]1-[C:5]-[C:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-1>>[CH3;D1;+0:8]-[C:10]-[C:11]-[C:12]-[O;H0;D2;+0:3]-[#15:2](=[O;D1;H0:1])-[C:4]1-[C:5]-[C:6]-[CH2;D2;+0:7]-[C:13]-[CH2;D2;+0:9]-1 | null | [] | null | null | null | null | The title compound was prepared from cyclohexylphosphinic acid and n-butanol according the the method described in Procedure 43. The compound was used without further purification.
Conditions: See reaction.notes.procedure_details.
Workup: The compound was used without further purification | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | Other | C(CCC)O | null | null | O=[PH](O)C1CCCCC1>C(CCC)O>CCCCO[PH](=O)C1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8779dd64d7dd4ab6a8cba54d39669391 | C=O.CCCCO[PH](=O)C1CCCCC1>>CCCCOP(=O)(CO)C1CCCCC1 | C1(CCCCC1)P(OCCCC)=O.C=O>>C1(CCCCC1)P(OCCCC)(=O)CO | [CH2:8]=[O:9].[CH3:1][CH2:2][CH2:3][CH2:4][O:5][PH:6](=[O:7])[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6](=[O:7])([CH2:8][OH:9])[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | C=O.CCCCO[PH](=O)C1CCCCC1 | CCCCOP(=O)(CO)C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | ff9e019412f5fb147910daaf4ee10ff7abac3966a22d93efa93ff9552cbbbf9e | a07b6e0bbdb5ea0627df192b2885de7d34cb5e55531d8d5102717495a910d9a6 | C1CCCCC1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[C:4](-[PH;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8])-[C:9]>>[C:3]-[C:4](-[P;H0;D4;+0:5](=[O;D1;H0:6])(-[#8:7]-[C:8])-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:9] | null | [] | null | null | null | null | The title compound was prepared from cyclohexylphosphinic acid, n-butyl ester and paraformaldehyde according to the method described in Procedure 31. Purification by chromatography, eluting with dichloromethane containing 5% methanol, gave an oil.
Conditions: See reaction.notes.procedure_details.
Workup: Purification b... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | null | null | C1CCCCC1 | null | null | null | null | C=O.CCCCO[PH](=O)C1CCCCC1>>CCCCOP(=O)(CO)C1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d63aff1397e8480b8c2a33699be1bede | CCCCOP(=O)(COc1ccccc1)C1CCC(CCN)CC1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2)cc1>>CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(OCc3ccccc3)cc2)CC1 | NCCC1CCC(CC1)P(OCCCC)(=O)COC1=CC=CC=C1.C(C1=CC=CC=C1)OC1=CC=C(OC[C@H]2OC2)C=C1>>C(C1=CC=CC=C1)OC1=CC=C(OCC(CNCCC2CCC(CC2)[P@@](OCCCC)(=O)COC2=CC=CC=C2)O)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6](=[O:7])([CH2:8][O:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[CH:16]1[CH2:17][CH2:18][CH:19]([CH2:20][CH2:21][NH2:22])[CH2:42][CH2:43]1.[CH2:23]1[C@@H:24]([CH2:26][O:27][c:28]2[cH:29][cH:30][c:31]([O:32][CH2:33][c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[cH:40][cH:41]2)[O:25]1... | CCCCOP(=O)(COc1ccccc1)C1CCC(CCN)CC1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2)cc1 | CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(OCc3ccccc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | O=[PH](COc1ccccc1)C1CCC(CCNCCCOc2ccc(OCc3ccccc3)cc2)CC1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | null | null | The title compound was prepared from 4-(2-aminoethyl)phenoxy methylcyclohexylphosphinic acid, n-butyl ester and (S)-2-(4-benzyloxyphenoxymethyl)oxirane according to the method described in Procedure 13.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.C1CCCCC1.c1ccccc1.c1ccccc1 | null | null | null | null | CCCCOP(=O)(COc1ccccc1)C1CCC(CCN)CC1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2)cc1>>CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(OCc3ccccc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7f98044a2f33492ab975abc63fa26522 | C=CCCCC.O=[PH2]O>>CCCCCC[PH](=O)O | C=CCCCC.[PH2](O)=O>>C(CCCCC)P(O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[PH2:7](=[O:8])[OH:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][PH:7](=[O:8])[OH:9] | C=CCCCC.O=[PH2]O | CCCCCC[PH](=O)O | null | null | null | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | null | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[O;D1;H0:5]=[PH2;D2;+0:6]-[O;D1;H1:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[PH;D3;+0:6](=[O;D1;H0:5])-[O;D1;H1:7] | null | [] | null | null | null | null | The title compound was prepared from n-hexene and 50% aqueous phosphinic acid by an analogous procedure to that described in J. Inorg. Nucl. Chem., 1965, 27, 697.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | null | null | null | null | null | C=CCCCC.O=[PH2]O>>CCCCCC[PH](=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f16851ac82164be198238393b2929fcf | CCCCCC[PH](=O)O>>CCCCCC[PH](=O)OCCCC | C(CCCCC)P(O)=O>>C(CCCCC)P(OCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][PH:7](=[O:8])[OH:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][PH:7](=[O:8])[O:9][CH2:10][CH2:11][CH2:12][CH3:13] | CCCCCC[PH](=O)O | CCCCCC[PH](=O)OCCCC | null | null | C(CCC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [C:1]-[#15:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:5]-[C:6]-[O;H0;D2;+0:4]-[#15:2](-[C:1])=[O;D1;H0:3] | null | [] | null | null | null | null | The title compound was prepared from n-hexylphosphinic acid and n-butanol according the the method described in Procedure 43. The compound was used without further purification.
Conditions: See reaction.notes.procedure_details.
Workup: The compound was used without further purification | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | C(CCC)O | null | null | CCCCCC[PH](=O)O>C(CCC)O>CCCCCC[PH](=O)OCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8ac817860d9d44d4acd7988671266af2 | C=O.CCCCCC[PH](=O)OCCCC>>CCCCCCP(=O)(CO)OCCCC | C(CCCCC)P(OCCCC)=O.C=O>>C(CCCCC)P(OCCCC)(=O)CO | [CH2:9]=[O:10].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][PH:7](=[O:8])[O:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][P:7](=[O:8])([CH2:9][OH:10])[O:11][CH2:12][CH2:13][CH2:14][CH3:15] | C=O.CCCCCC[PH](=O)OCCCC | CCCCCCP(=O)(CO)OCCCC | null | null | null | Miscellaneous | OtherReaction | ff9e019412f5fb147910daaf4ee10ff7abac3966a22d93efa93ff9552cbbbf9e | a07b6e0bbdb5ea0627df192b2885de7d34cb5e55531d8d5102717495a910d9a6 | null | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[#8:4]-[PH;D3;+0:5](=[O;D1;H0:6])-[C:7]-[C:8]>>[C:3]-[#8:4]-[P;H0;D4;+0:5](=[O;D1;H0:6])(-[C:7]-[C:8])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | The title compound was prepared from n-hexylphosphinic acid, n-butyl ester and paraformaldehyde according to the method described in Procedure 31. Purification by chromatography, eluting with dichloromethane containing 5% methanol, gave an oil.
Conditions: See reaction.notes.procedure_details.
Workup: Purification by c... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | null | null | null | null | null | null | null | C=O.CCCCCC[PH](=O)OCCCC>>CCCCCCP(=O)(CO)OCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-21a512275c5740b8a6d9a02b334da1ec | NCCc1ccc(O)cc1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2)cc1>>Oc1ccc(CCNC[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1 | NCCC1=CC=C(C=C1)O.C(C1=CC=CC=C1)OC1=CC=C(OC[C@H]2OC2)C=C1>>C(C1=CC=CC=C1)OC1=CC=C(OC[C@H](CNCCC2=CC=C(C=C2)O)O)C=C1 | [OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH2:8])[cH:28][cH:29]1.[CH2:9]1[C@@H:10]([CH2:12][O:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:26][cH:27]2)[O:11]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH:8][CH2:9][C@H:10]([OH:11])[CH2:12][O:13][c:14]2[cH:15][cH:16]... | NCCc1ccc(O)cc1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2)cc1 | Oc1ccc(CCNC[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(CCNCCCOc2ccc(OCc3ccccc3)cc2)cc1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | null | null | The title compound was prepared from tyramine and (S)-2-(4-benzyloxyphenoxymethyl)oxirane according to the method described in Procedure 13.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | NCCc1ccc(O)cc1.c1ccc(COc2ccc(OC[C@@H]3CO3)cc2)cc1>>Oc1ccc(CCNC[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c88884b2244548bda021d31a20f133fd | BrCc1ccccc1.Oc1ccc(CCNC[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1>>Oc1ccc(CCN(Cc2ccccc2)C[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1 | C(C1=CC=CC=C1)OC1=CC=C(OC[C@H](CNCCC2=CC=C(C=C2)O)O)C=C1.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[Na+].[Na+]>>C(C1=CC=CC=C1)N(CCC1=CC=C(C=C1)O)C[C@@H](COC1=CC=C(C=C1)OCC1=CC=CC=C1)O | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH:8][CH2:16][C@H:17]([OH:18])[CH2:19][O:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[cH:33][cH:34]2)[cH:35][cH:36]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]([CH2:9][c... | BrCc1ccccc1.Oc1ccc(CCNC[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1 | Oc1ccc(CCN(Cc2ccccc2)C[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCN(CCCOc2ccc(OCc3ccccc3)cc2)Cc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | A solution of (S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol (1.9 g, 4.8 mMol) and benzyl bromide (0.57 ml, 4.8 mMol) in dimethylformamide (10 ml) containing sodium carbonate (770 mg, 7.2 mMol) was stirred at room temperature for 18 hours. The mixture was filtered and the residue was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 18 | BrCc1ccccc1.Oc1ccc(CCNC[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1>CN(C=O)C>Oc1ccc(CCN(Cc2ccccc2)C[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fbb7b4f2d98e40cc842d6d8dc54f1727 | C[Si](C)(C)N[Si](C)(C)C.ClCc1ccccc1.O=[PH2][O-]>>CCCCO[PH](=O)Cc1ccccc1 | [PH2]([O-])=O.[NH4+].C[Si](N[Si](C)(C)C)(C)C.C(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)P(OCCCC)=O | C[Si](N[Si](C)([CH3:1])[CH3:4])([CH3:2])[CH3:3].Cl[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O-:5][PH2:6]=[O:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][PH:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | C[Si](C)(C)N[Si](C)(C)C.ClCc1ccccc1.O=[PH2][O-] | CCCCO[PH](=O)Cc1ccccc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 896e526c4cf7b73f9e61941ba9abeea264ce8bddded81bccc6872aa9369bde62 | 21c2d6ad627e0d89816de17f4010107ca25a77225bb725f813a79c7150b158e4 | c1ccccc1 | C-[Si](-[CH3;D1;+0:1])(-[CH3;D1;+0:2])-N-[Si](-C)(-[CH3;D1;+0:3])-[CH3;D1;+0:4].Cl-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8].[O-;H0;D1:9]-[PH2;D2;+0:10]=[O;D1;H0:11]>>[CH3;D1;+0:3]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:4]-[O;H0;D2;+0:9]-[PH;D3;+0:10](=[O;D1;H0:11])-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 110 | CELSIUS | 18 | HOUR | A mixture of ammonium phosphinate (9.18 g) and hexamethyldisilazane (25 mL) was heated at 110° C. for 2 hours. The mixture was cooled in ice, dissolved in dry dichloromethane (120 mL), benzyl chloride (20 g; 14 mL) was added and the mixture allowed to warm to room temperature and stirred 18 hours. The solution was filt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Silyl protective group.Silyl protective group | null | null | null | c1ccccc1 | HCl | ClCCl | 110 | 18 | C[Si](C)(C)N[Si](C)(C)C.ClCc1ccccc1.O=[PH2][O-]>ClCCl>CCCCO[PH](=O)Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b4965ae0e45f4361b45b7c919bb59755 | C=O.CCCCO[PH](=O)Cc1ccccc1>>CCCCOP(=O)(CO)Cc1ccccc1 | C(C1=CC=CC=C1)P(OCCCC)=O.C=O>>C(C1=CC=CC=C1)P(OCCCC)(=O)CO | [CH2:8]=[O:9].[CH3:1][CH2:2][CH2:3][CH2:4][O:5][PH:6](=[O:7])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6](=[O:7])([CH2:8][OH:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C=O.CCCCO[PH](=O)Cc1ccccc1 | CCCCOP(=O)(CO)Cc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | ff9e019412f5fb147910daaf4ee10ff7abac3966a22d93efa93ff9552cbbbf9e | a07b6e0bbdb5ea0627df192b2885de7d34cb5e55531d8d5102717495a910d9a6 | c1ccccc1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[#8:4]-[PH;D3;+0:5](=[O;D1;H0:6])-[C:7]-[c:8]>>[C:3]-[#8:4]-[P;H0;D4;+0:5](=[O;D1;H0:6])(-[C:7]-[c:8])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | The title compound was prepared from benzylphosphinic acid, n-butyl ester and paraformaldehyde according to the method described in Procedure 31.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | null | null | c1ccccc1 | null | null | null | null | C=O.CCCCO[PH](=O)Cc1ccccc1>>CCCCOP(=O)(CO)Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b2ca7107578479d93f1b4ae6d8fd313 | CCCCOP(=O)(CO)Cc1ccccc1.O=S(=O)(Cl)c1ccc(Cl)cc1>>CCCCOP(=O)(COS(=O)(=O)c1ccc(Cl)cc1)Cc1ccccc1 | C(C1=CC=CC=C1)P(OCCCC)(=O)CO.ClC1=CC=C(C=C1)S(=O)(=O)Cl>>C(C1=CC=CC=C1)P(OCCCC)(=O)COS(=O)(=O)C1=CC=C(C=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6](=[O:7])([CH2:8][OH:9])[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][P:6](=[O:7])([CH2:8][O:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][c... | CCCCOP(=O)(CO)Cc1ccccc1.O=S(=O)(Cl)c1ccc(Cl)cc1 | CCCCOP(=O)(COS(=O)(=O)c1ccc(Cl)cc1)Cc1ccccc1 | null | null | null | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | O=[PH](COS(=O)(=O)c1ccccc1)Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#15:7]-[C:8]-[OH;D1;+0:9]>>[#15:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | The title compound was prepared from benzylhydroxymethylphosphinic acid, n-butyl ester and 4-chlorobenzenesulfonyl chloride according to the method described in Procedure 32. The resulting white solid (mp 87°-88° C.) was used in the next stage without further purification.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | CCCCOP(=O)(CO)Cc1ccccc1.O=S(=O)(Cl)c1ccc(Cl)cc1>>CCCCOP(=O)(COS(=O)(=O)c1ccc(Cl)cc1)Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bcd59e6d31334fa7a06760faa96f245d | COC(=O)COc1ccc(CC(C)NCC(O)COc2ccc(O)c(O)c2)cc1>>CC(Cc1ccc(OCC(=O)O)cc1)NCC(O)COc1ccc(O)c(O)c1 | Cl.OC(CNC(CC1=CC=C(OCC(=O)OC)C=C1)C)COC1=CC(=C(C=C1)O)O.Cl>>Cl.OC=1C=C(OCC(CNC(CC2=CC=C(OCC(=O)O)C=C2)C)O)C=CC1O | C[O:12][C:10]([CH2:9][O:8][c:7]1[cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:15][CH2:16][CH:17]([OH:18])[CH2:19][O:20][c:21]2[cH:22][cH:23][c:24]([OH:25])[c:26]([OH:27])[cH:28]2)[cH:14][cH:13]1)=[O:11]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][C:10](=[O:11])[OH:12])[cH:13][cH:14]1)[NH:15][CH2:16][CH:17]... | COC(=O)COc1ccc(CC(C)NCC(O)COc2ccc(O)c(O)c2)cc1 | CC(Cc1ccc(OCC(=O)O)cc1)NCC(O)COc1ccc(O)c(O)c1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CCNCCCOc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 100 | CELSIUS | null | null | A solution of (SR)-4-{2-[2-hydroxy-3-(3,4-dihydroxyphenoxy)propylamino]propyl}phenoxyacetic acid, methyl ester, hydrochloride (78 mg, 0.17 mMol) in water (2 ml) containing hydrochloric acid (1M, 0.5 ml, 0.51 mMol) was heated at 100° C. under argon for 3 hours. After cooling to room temperature the solution was freeze d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | O | 100 | null | COC(=O)COc1ccc(CC(C)NCC(O)COc2ccc(O)c(O)c2)cc1>O>CC(Cc1ccc(OCC(=O)O)cc1)NCC(O)COc1ccc(O)c(O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8e4211f4f8714a32ba4f81b5ab11c25a | CCCCO[P@@](=O)(CCCOCc1ccccc1)COc1ccc(CCNCC(O)COc2ccc(O)c(CO)c2)cc1>>O=P(O)(CCCOCc1ccccc1)COc1ccc(CCNC[C@H](O)COc2ccc(O)c(CO)c2)cc1 | OC(CNCCC1=CC=C(OC[P@](OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1)COC1=CC(=C(C=C1)O)CO.Cl>>O[C@@H](CNCCC1=CC=C(OCP(O)(=O)CCCOCC2=CC=CC=C2)C=C1)COC1=CC(=C(C=C1)O)CO | CCCC[O:3][P@@:2](=[O:1])([CH2:4][CH2:5][CH2:6][O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:15][O:16][c:17]1[cH:18][cH:19][c:20]([CH2:21][CH2:22][NH:23][CH2:24][CH:25]([OH:26])[CH2:27][O:28][c:29]2[cH:30][cH:31][c:32]([OH:33])[c:34]([CH2:35][OH:36])[cH:37]2)[cH:38][cH:39]1>>[O:1]=[P:2]([OH:3])([CH2:4][CH2... | CCCCO[P@@](=O)(CCCOCc1ccccc1)COc1ccc(CCNCC(O)COc2ccc(O)c(CO)c2)cc1 | O=P(O)(CCCOCc1ccccc1)COc1ccc(CCNC[C@H](O)COc2ccc(O)c(CO)c2)cc1 | null | null | null | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=[PH](CCCOCc1ccccc1)COc1ccc(CCNCCCOc2ccccc2)cc1 | C-C-C-C-[O;H0;D2;+0:1]-[P@;H0;D4;+0:2](=[O;D1;H0:3])(-[C:4]-[#8:5])-[C:6]-[C:7]>>[#8:5]-[C:4]-[P;H0;D4;+0:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[C:6]-[C:7] | null | [] | null | null | null | null | The title compound was prepared from (S)-4-{2-[2-hydroxy-3-(4-hydroxy-3-hydroxymethyl-phenoxy)propylamino]ethyl}phenoxymethyl-(3-benzyloxypropyl)phosphinic acid, n-butyl ester according to a modification of the procedure described in Example 5. Acidification to pH 3.5 with 1M hydrochloric acid followed by C18 reverse p... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCCCO[P@@](=O)(CCCOCc1ccccc1)COc1ccc(CCNCC(O)COc2ccc(O)c(CO)c2)cc1>>O=P(O)(CCCOCc1ccccc1)COc1ccc(CCNC[C@H](O)COc2ccc(O)c(CO)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-53f0eba6f5424c5d8afd83daf49ced93 | CCCCOP(=O)(CCCOCc1ccccc1)COc1ccc(CC(C)NCC(O)COc2ccc(O)c(CO)c2)cc1>>CC(Cc1ccc(OCP(=O)(O)CCCOCc2ccccc2)cc1)NCC(O)COc1ccc(O)c(CO)c1 | OC(CNC(CC1=CC=C(OCP(OCCCC)(=O)CCCOCC2=CC=CC=C2)C=C1)C)COC1=CC(=C(C=C1)O)CO.Cl>>Cl.OC(CNC(CC1=CC=C(OCP(O)(=O)CCCOCC2=CC=CC=C2)C=C1)C)COC1=CC(=C(C=C1)O)CO | CCCC[O:12][P:10]([CH2:9][O:8][c:7]1[cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:26][CH2:27][CH:28]([OH:29])[CH2:30][O:31][c:32]2[cH:33][cH:34][c:35]([OH:36])[c:37]([CH2:38][OH:39])[cH:40]2)[cH:25][cH:24]1)(=[O:11])[CH2:13][CH2:14][CH2:15][O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH:2]([CH2:3][c:... | CCCCOP(=O)(CCCOCc1ccccc1)COc1ccc(CC(C)NCC(O)COc2ccc(O)c(CO)c2)cc1 | CC(Cc1ccc(OCP(=O)(O)CCCOCc2ccccc2)cc1)NCC(O)COc1ccc(O)c(CO)c1 | null | null | null | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=[PH](CCCOCc1ccccc1)COc1ccc(CCNCCCOc2ccccc2)cc1 | C-C-C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(-[C:4])=[O;D1;H0:5]>>[C:3]-[#15:2](-[C:4])(=[O;D1;H0:5])-[OH;D1;+0:1] | null | [] | null | null | null | null | The title compound was prepared from (SR)-4-{2-[2-hydroxy-3-(4-hydroxy-3-hydroxymethylphenoxy)propylamino]propyl}phenoxymethyl(3-benzyloxypropyl)phosphinic acid, n-butyl ester according to a modification of the procedure described in Example 5. Acidification to pH 3.5 with 1M hydrochloric acid followed by C18 reverse p... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCCCOP(=O)(CCCOCc1ccccc1)COc1ccc(CC(C)NCC(O)COc2ccc(O)c(CO)c2)cc1>>CC(Cc1ccc(OCP(=O)(O)CCCOCc2ccccc2)cc1)NCC(O)COc1ccc(O)c(CO)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-722dbda67fac4d1c8121beafd45c9dbf | CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(OCc3ccccc3)cc2)CC1>>CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(O)cc2)CC1 | OC(CNCCC1CCC(CC1)[P@@](OCCCC)(=O)COC1=CC=CC=C1)COC1=CC=C(C=C1)OCC1=CC=CC=C1>>OC(CNCCC1CCC(CC1)[P@@](OCCCC)(=O)COC1=CC=CC=C1)COC1=CC=C(C=C1)O | c1ccc(C[O:32][c:31]2[cH:30][cH:29][c:28]([O:27][CH2:26][CH:24]([CH2:23][NH:22][CH2:21][CH2:20][CH:19]3[CH2:18][CH2:17][CH:16]([P@@:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])(=[O:7])[CH2:8][O:9][c:10]4[cH:11][cH:12][cH:13][cH:14][cH:15]4)[CH2:36][CH2:35]3)[OH:25])[cH:34][cH:33]2)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][P@:6](=... | CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(OCc3ccccc3)cc2)CC1 | CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(O)cc2)CC1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=[PH](COc1ccccc1)C1CCC(CCNCCCOc2ccccc2)CC1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 24 | HOUR | A solution of (S)-4-{2-[2-hydroxy-3-(4-benzyloxyphenoxy)propylamino]ethyl}phenoxymethylcyclohexylphosphinic acid, n-butyl ester (1.00 g, 1.64 mMol) in methanol (100 ml) containing 10% palladium on charcoal (50 mg) was hydrogenated at 40° C. and 40 p.s.i. for 24 hours. After cooling to room temperature the suspension wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.C1CCCCC1.c1ccccc1 | Other | [Pd].CO | null | 24 | CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(OCc3ccccc3)cc2)CC1>[Pd].CO>CCCCO[P@](=O)(COc1ccccc1)C1CCC(CCNCC(O)COc2ccc(O)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f306d8cee34644e195747dc14d730ec8 | CCCCO[P@@](=O)(CCCC(CC)CCNCC(O)COc1ccc(O)cc1)COc1ccccc1>>CC[C@@H](CCCP(=O)(O)COc1ccccc1)CCNCC(O)COc1ccc(O)cc1 | OC(CNCCC(CCC[P@@](OCCCC)(=O)COC1=CC=CC=C1)CC)COC1=CC=C(C=C1)O.Cl>>OC(CNCC[C@H](CCCP(O)(=O)COC1=CC=CC=C1)CC)COC1=CC=C(C=C1)O | CCCC[O:9][P@:7]([CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[CH2:18][CH2:19][NH:20][CH2:21][CH:22]([OH:23])[CH2:24][O:25][c:26]1[cH:27][cH:28][c:29]([OH:30])[cH:31][cH:32]1)(=[O:8])[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH2:2][C@@H:3]([CH2:4][CH2:5][CH2:6][P:7](=[O:8])([OH:9])[CH2:10][O:11][c... | CCCCO[P@@](=O)(CCCC(CC)CCNCC(O)COc1ccc(O)cc1)COc1ccccc1 | CC[C@@H](CCCP(=O)(O)COc1ccccc1)CCNCC(O)COc1ccc(O)cc1 | null | null | null | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=[PH](CCCCCCNCCCOc1ccccc1)COc1ccccc1 | C-C-C-C-[O;H0;D2;+0:1]-[P@;H0;D4;+0:2](=[O;D1;H0:3])(-[C:4]-[#8:5])-[C:6]-[C:7]>>[#8:5]-[C:4]-[P;H0;D4;+0:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[C:6]-[C:7] | null | [] | null | null | null | null | The title compound was prepared from (S)-4-{2-[2-hydroxy-3-(4-hydroxyphenoxy)propylamino]ethyl}phenoxymethyl-n-hexyl phosphinic acid, n-butyl ester according a modification of the procedure described in Example 25. Acidification to pH 6 with 1M hydrochloric acid followed by C18 reverse phase chromatography and freeze d... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | CCCCO[P@@](=O)(CCCC(CC)CCNCC(O)COc1ccc(O)cc1)COc1ccccc1>>CC[C@@H](CCCP(=O)(O)COc1ccccc1)CCNCC(O)COc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7dcfc77b6fae44dabea5f16d26269c62 | CCCCOP(=O)(COc1ccccc1)Cc1ccc(CC(C)NCC(O)COc2ccc(O)c(CO)c2)cc1>>CC(Cc1ccc(CP(=O)(O)COc2ccccc2)cc1)NCC(O)COc1ccc(O)c(CO)c1 | Cl.OC(CNC(CC1=CC=C(CP(OCCCC)(=O)COC2=CC=CC=C2)C=C1)C)COC1=CC(=C(C=C1)O)CO>>OC(CNC(CC1=CC=C(CP(O)(=O)COC2=CC=CC=C2)C=C1)C)COC1=CC(=C(C=C1)O)CO | CCCC[O:11][P:9]([CH2:8][c:7]1[cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:22][CH2:23][CH:24]([OH:25])[CH2:26][O:27][c:28]2[cH:29][cH:30][c:31]([OH:32])[c:33]([CH2:34][OH:35])[cH:36]2)[cH:21][cH:20]1)(=[O:10])[CH2:12][O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][P... | CCCCOP(=O)(COc1ccccc1)Cc1ccc(CC(C)NCC(O)COc2ccc(O)c(CO)c2)cc1 | CC(Cc1ccc(CP(=O)(O)COc2ccccc2)cc1)NCC(O)COc1ccc(O)c(CO)c1 | null | null | null | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=[PH](COc1ccccc1)Cc1ccc(CCNCCCOc2ccccc2)cc1 | C-C-C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(-[C:4])=[O;D1;H0:5]>>[C:3]-[#15:2](-[C:4])(=[O;D1;H0:5])-[OH;D1;+0:1] | null | [] | null | null | null | null | The title compound was prepared from (SR)-4-{2-[2-hydroxy-3-(4-hydroxy-3-hydroxymethyl-phenoxy)propylamino]propyl}phenoxymethylbenzylphosphinic acid, n-butyl ester according to the method described in Example 5 followed by acidification to pH 3.5 with 1M hydrochloric acid, as a solid (mp 180°-183° C.) following chromat... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCCCOP(=O)(COc1ccccc1)Cc1ccc(CC(C)NCC(O)COc2ccc(O)c(CO)c2)cc1>>CC(Cc1ccc(CP(=O)(O)COc2ccccc2)cc1)NCC(O)COc1ccc(O)c(CO)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32e98db4036848ce8b8264c0ec0c3131 | CCC(CC)OP(=O)(O)O.CCOC(C)=O.Cc1cn(COCOC(=O)c2ccccc2)c(=O)[nH]c1=O>>CCOP(=O)(COCOCn1cc(C)c(=O)[nH]c1=O)OCC | C(C)(=O)OCC.C(C1=CC=CC=C1)(=O)OCOCN1C(=O)NC(=O)C(C)=C1.C(C)C(OP(=O)(O)O)CC.FC(S(=O)(=O)O[Si](C)(C)C)(F)F>>C(C)OP(=O)(OCC)COCOCN1C(=O)NC(=O)C(C)=C1 | CCC(O[P:4](O)(=[O:5])[OH:20])[CH2:21][CH3:22].CC(=O)[O:3][CH2:2][CH3:1].O=[C:6](c1ccccc1)[O:7][CH2:8][O:9][CH2:10][n:11]1[cH:12][c:13]([CH3:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][O:9][CH2:10][n:11]1[cH:12][c:13]([CH3:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19])[O:20]... | CCC(CC)OP(=O)(O)O.CCOC(C)=O.Cc1cn(COCOC(=O)c2ccccc2)c(=O)[nH]c1=O | CCOP(=O)(COCOCn1cc(C)c(=O)[nH]c1=O)OCC | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 0011ab4c5e0e8d6ec22b1403e9fa2cfd5f1c5f5ed345a8324698dd0f9a332eea | 5a67587bdd06f11f80d02c1bbacae855575e59f72bbbfb0c1648772d5a52e271 | O=c1cc[nH]c(=O)[nH]1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C;D1;H3:3].C-C-C(-O-[P;H0;D4;+0:4](-O)(=[O;D1;H0:5])-[OH;D1;+0:6])-[CH2;D2;+0:7]-[C;D1;H3:8].O=[C;H0;D3;+0:9](-[#8:10]-[C:11])-c1:c:c:c:c:c:1>>[C:11]-[#8:10]-[CH2;D2;+0:9]-[P;H0;D4;+0:4](=[O;D1;H0:5])(-[O;H0;D2;+0:6]-[CH2;D2;+0:7]-[C;D1;H3:8])-[O;H0;D2;+0:1]-[C:2]-[C;D1;H3:3] | null | [] | 85 | CELSIUS | null | null | To a solution of 1-[(benzoyloxy)methoxymethyl]thymine (2.9 g, 10 mmol) and diethyl phosphonomethanol (1.85 g, 11 mmol) in benzene (180 mL) was added trimethylsilyl trifluoromethanesulfonate (0.05 mL) via a syringe under nitrogen. The solution was heated at 85° C. for 20 min. After cooling to room temperature, ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Phosphate ester | Ether | c1ccccc1 | null | c1cncnc1 | HO- | C1=CC=CC=C1 | 85 | null | CCC(CC)OP(=O)(O)O.CCOC(C)=O.Cc1cn(COCOC(=O)c2ccccc2)c(=O)[nH]c1=O>C1=CC=CC=C1>CCOP(=O)(COCOCn1cc(C)c(=O)[nH]c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77276d898fd0423db0141ad034a6f470 | CCOP(=O)(COCOCCl)OCC.Nc1nc(Cl)c2[nH]cnc2n1>>CCOP(=O)(COCOCn1cnc2c(Cl)nc(N)nc21)OCC | [H-].[Na+].ClCOCOCP(=O)(OCC)OCC.NC1=NC(=C2NC=NC2=N1)Cl>>NC1=NC(=C2N=CN(C2=N1)COCOCP(=O)(OCC)OCC)Cl | Cl[CH2:10][O:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:22][CH2:23][CH3:24].[nH:11]1[cH:12][n:13][c:14]2[n:20][c:18]([NH2:19])[n:17][c:15]([Cl:16])[c:21]12>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][O:9][CH2:10][n:11]1[cH:12][n:13][c:14]2[c:15]([Cl:16])[n:17][c:18]([NH2:19])[n:20][c:21]12)[O:2... | CCOP(=O)(COCOCCl)OCC.Nc1nc(Cl)c2[nH]cnc2n1 | CCOP(=O)(COCOCn1cnc2c(Cl)nc(N)nc21)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 216f1d1b2e599190b2de244995a4e132e5cff1104483d70bd1d02c3a4261d102 | a0a01b3cbff93f3bdd38266e6735d54f714324d4b50ebf14fee21f956ddad209 | c1ncc2nc[nH]c2n1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[Cl;D1;H0:4]-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7](-[N;D1;H2:8]):[n;H0;D2;+0:9]:[c;H0;D3;+0:10]2:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c;H0;D3;+0:14]:2:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[#7;a:11]:[c;H0;D3;+0:10]2:[c;H0;D3;+0:5](-[Cl;D1;H0:4]):[#7;a:6]:[c:7](-[N;D1;H2:8]):[n;H0;D2;+0... | null | [] | 25 | CELSIUS | 1 | HOUR | To a suspension of 60% sodium hydride in mineral oil (1.4 g, 34.5 mmol) in DMF (100 mL) was added 2-amino-6-chloropurine (5.78 g, 34.2 mmol) and the mixture was stirred for 1 hr at 25° C. To the resulting yellow solution was added dropwise a solution of above chloromethoxy(diethylphosphonomethoxy)methane in DMF (20 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Ether | Aromatic halide.Ether | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | CN(C)C=O | 25 | 1 | CCOP(=O)(COCOCCl)OCC.Nc1nc(Cl)c2[nH]cnc2n1>CN(C)C=O>CCOP(=O)(COCOCn1cnc2c(Cl)nc(N)nc21)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93d03e24b2e64b579f6821175b3c99c2 | CCOP(COCOCCl)OCC.Nc1ncnc2nc[nH]c12>>CCOP(=O)(COCOCn1cnc2c(N)ncnc21)OCC | ClCOCOCP(OCC)OCC.[H-].[Na+].C(C)OP(=O)(OCC)[O-].ClCOCOCCl.N1=CN=C2N=CNC2=C1N>>C(C)OP(=O)(OCC)COCOCN1C2=NC=NC(=C2N=C1)N | Cl[CH2:10][O:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])[O:21][CH2:22][CH3:23].[n:11]1[cH:12][nH:13][c:14]2[c:15]([NH2:16])[n:17][cH:18][n:19][c:20]12>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][O:9][CH2:10][n:11]1[cH:12][n:13][c:14]2[c:15]([NH2:16])[n:17][cH:18][n:19][c:20]12)[O:21][CH2:22][CH3:23] | CCOP(COCOCCl)OCC.Nc1ncnc2nc[nH]c12 | CCOP(=O)(COCOCn1cnc2c(N)ncnc21)OCC | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 9abd68eff6abfb54236fe246d2ef743ebf10d5f42c95aac86e158e6fcd485fec | 42c71821dc42e0c1902cec868cf7d0abd0a4511b0313126f4c5eb9aac58d5cad | c1ncc2nc[nH]c2n1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3]-[#8:4]-[C:5]-[P;H0;D3;+0:6](-[#8:7]-[C:8])-[#8:9]-[C:10].[N;D1;H2:11]-[c:12]1:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]2:[n;H0;D2;+0:17]:[c:18]:[nH;D2;+0:19]:[c:20]:1:2>>[C:8]-[#8:7]-[P;H0;D4;+0:6](=[O;D1;H0:21])(-[#8:9]-[C:10])-[C:5]-[#8:4]-[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:17]1:[c:18]:[n;H0... | null | [] | 80 | CELSIUS | 1 | HOUR | To a suspension of 60% sodium hydride in mineral oil (1.4 g, 34.5 mmol) in DMF (100 mL) was added adenine (4.7 g, 34.5 mmol) and the mixture was stirred at 80° C. for 1 hr. To the resulting yellow solution was added dropwise a solution of chloromethoxy(diethoxyphosphinomethoxy)methane [(prepared from diethylphosphate (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1ncc2nc[nH]c2n1 | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | null | CN(C)C=O | 80 | 1 | CCOP(COCOCCl)OCC.Nc1ncnc2nc[nH]c12>CN(C)C=O>CCOP(=O)(COCOCn1cnc2c(N)ncnc21)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-56bf9eb6e7e746298f149b2bbd996b66 | CCOP(=O)(COCOCCl)OCC.Nc1cc[nH]c(=O)n1>>CCOP(=O)(COCOCn1ccc(N)nc1=O)OCC | [H-].[Na+].ClCOCOCP(=O)(OCC)OCC.N1C(=O)N=C(N)C=C1>>C(C)OP(=O)(OCC)COCOCN1C(=O)N=C(N)C=C1 | Cl[CH2:10][O:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:19][CH2:20][CH3:21].[nH:11]1[cH:12][cH:13][c:14]([NH2:15])[n:16][c:17]1=[O:18]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][O:9][CH2:10][n:11]1[cH:12][cH:13][c:14]([NH2:15])[n:16][c:17]1=[O:18])[O:19][CH2:20][CH3:21] | CCOP(=O)(COCOCCl)OCC.Nc1cc[nH]c(=O)n1 | CCOP(=O)(COCOCn1ccc(N)nc1=O)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 06dfed3106c428c0f55338752b8abbb17bab6785f3cc392db7055710fc6495af | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | O=c1nccc[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[O;D1;H0:4]=[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1=[O;D1;H0:4] | null | [] | 80 | CELSIUS | 15 | HOUR | To a suspension of 60% sodium hydride in mineral oil (700 mg, 17 mmol) in DMF (50 mL) was added cytosine (1.9 g, 17 mmol) and the mixture was heated at 80° C. for 2 hr under nitrogen. To the resulting yellow solution was added dropwise a solution of chloromethoxy(diethylphosphonomethoxy)methane [prepared from diethylph... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1ccncn1 | c1cncnc1 | c1cncnc1 | HCl | CN(C)C=O | 80 | 15 | CCOP(=O)(COCOCCl)OCC.Nc1cc[nH]c(=O)n1>CN(C)C=O>CCOP(=O)(COCOCn1ccc(N)nc1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e7425b3ba2444f079944b9d7bd609176 | C=O.ClCCl.OCC[Se]c1ccccc1>>ClCOCC[Se]c1ccccc1 | C1(=CC=CC=C1)[Se]CCO.C=O.C(Cl)Cl>>C1(=CC=CC=C1)[Se]CCOCCl | O=[CH2:2].ClC[Cl:1].[OH:3][CH2:4][CH2:5][Se:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[Cl:1][CH2:2][O:3][CH2:4][CH2:5][Se:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=O.ClCCl.OCC[Se]c1ccccc1 | ClCOCC[Se]c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2f66a7b791ce8e51834c825fa4b4a8e80b5ba150d2e0f9b01c3670ab1489df68 | c22f3e3cfb808b8fb5dc9e224a4962596d53a693fe06c73a918a5d25fa10d01c | c1ccccc1 | Cl-C-[Cl;H0;D1;+0:1].O=[CH2;D1;+0:2].[C:3]-[C:4]-[OH;D1;+0:5]>>[C:3]-[C:4]-[O;H0;D2;+0:5]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | To a solution of 2-(phenylselenyl)ethanol (4.0 g, 20 mmol) [prepared according to the literature procedure: P. Rollin, V. V. Bencomo, P. Sinay, Synthesis, 13 (1984)] in CH2Cl2 (15 mL) was added paraformaldehyde (620 mg, 20 mmol). HCl gas was then bubbled into the solution at 5° C. for 2 hr. The solution was dried (MgSO... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Formaldehyde.Primary alcohol | Primary halide.Ether | null | null | c1ccccc1 | HCl | null | null | null | C=O.ClCCl.OCC[Se]c1ccccc1>>ClCOCC[Se]c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb7c577d427641d3b098b5304ce0b096 | COC1CCC(OC)O1.Cc1c[nH]c(=O)[nH]c1=O>>COC1CCC(n2cc(C)c(=O)[nH]c2=O)O1 | COC1OC(CC1)OC.[Sn](Cl)(Cl)(Cl)Cl.S(=O)(=O)([O-])[O-].[NH4+].[NH4+].Cl[Si](C)(C)C.N1C(=O)NC(=O)C(C)=C1>>COC1CCC(O1)N1C(=O)NC(=O)C(C)=C1 | CO[CH:6]1[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:16]1.[nH:7]1[cH:8][c:9]([CH3:10])[c:11](=[O:12])[nH:13][c:14]1=[O:15]>>[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][CH:6]([n:7]2[cH:8][c:9]([CH3:10])[c:11](=[O:12])[nH:13][c:14]2=[O:15])[O:16]1 | COC1CCC(OC)O1.Cc1c[nH]c(=O)[nH]c1=O | COC1CCC(n2cc(C)c(=O)[nH]c2=O)O1 | null | null | C[Si](N[Si](C)(C)C)(C)C.C(C)(=O)OCC.ClC(C)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 9b598d3fa89a3273540ae795a39c8396c116d041fc8f58b6aa756468b2271686 | ccc058ecd89f692c39a92bd6db91fb86578428d38b5955a659e0a2343eccf0fd | O=c1ccn(C2CCCO2)c(=O)[nH]1 | C-O-[CH;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1.[O;D1;H0:6]=[c:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[O;D1;H0:6]=[c:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:1-[CH;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1 | null | [] | 145 | CELSIUS | null | null | To a suspension of thymine (2.5 g, 20 mmol) in hexamethyldisilazane (30 mL) was added ammonium sulfate (50 mg) and chlorotrimethylsilane (0.5 mL) and the mixture was heated at 145° C. for 4 hr under nitrogen. The excess hexamethyldisilazane was removed at reduced pressure, and the residual oil was dissolved in xylene a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ether | C1CCOC1.c1cncnc1 | C1CCOC1.c1cncnc1 | C1CCOC1.c1cncnc1 | HO- | C[Si](N[Si](C)(C)C)(C)C.C(C)(=O)OCC.ClC(C)Cl | 145 | null | COC1CCC(OC)O1.Cc1c[nH]c(=O)[nH]c1=O>C[Si](N[Si](C)(C)C)(C)C.C(C)(=O)OCC.ClC(C)Cl>COC1CCC(n2cc(C)c(=O)[nH]c2=O)O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-560dc193ecc34b789acc357ab3f450a5 | CC(=O)Nc1nc(C(=O)N(c2ccccc2)c2ccccc2)c2ncn(COCC[Se]c3ccccc3)c2n1>>C=COCn1cnc2c(C(=O)N(c3ccccc3)c3ccccc3)nc(NC(C)=O)nc21 | C(C)(C)N(CC)C(C)C.C(C)(=O)NC1=NC(=C2N=CN(C2=N1)COCC[Se]C1=CC=CC=C1)C(N(C1=CC=CC=C1)C1=CC=CC=C1)=O.OO.C([O-])(O)=O.[Na+]>>C(C)(=O)NC1=NC(=C2N=CN(C2=N1)COC=C)C(N(C1=CC=CC=C1)C1=CC=CC=C1)=O | c1ccc([Se][CH2:1][CH2:2][O:3][CH2:4][n:5]2[cH:6][n:7][c:8]3[c:9]([C:10](=[O:11])[N:12]([c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[n:25][c:26]([NH:27][C:28]([CH3:29])=[O:30])[n:31][c:32]23)cc1>>[CH2:1]=[CH:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([C:10](=[O:11])[N:12]([c:1... | CC(=O)Nc1nc(C(=O)N(c2ccccc2)c2ccccc2)c2ncn(COCC[Se]c3ccccc3)c2n1 | C=COCn1cnc2c(C(=O)N(c3ccccc3)c3ccccc3)nc(NC(C)=O)nc21 | null | null | O1CCOCC1 | Functional Group Interconversion | OtherReaction | f0f1a26b0ed9935583cab47eabbbc5114ef7eea7864650856d5594f762522cc3 | 258173fc649f8a796b89cbbce487cd2ae8fd8b5c210e0d7885f99df8ff5c9f48 | O=C(c1ncnc2[nH]cnc12)N(c1ccccc1)c1ccccc1 | [C:1]-[#8:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[Se]-c1:c:c:c:c:c:1>>[C:1]-[#8:2]-[CH;D2;+0:3]=[CH2;D1;+0:4] | null | [] | 60 | CELSIUS | null | null | To a solution of 2-acetamido-6-diphenylcarbamoyl-9-[2-(phenylselenyl)ethoxymethyl]purine (4.92 g, 8.16 mmol) in dioxane (80 mL) was added 30% H2O2 (4 mL, 35 mmol) and sodium bicarbonate (2.1 g, 24.5 mmol). The mixture was heated at 60° C. for 20 min. The reaction was then concentrated to about 10 mL, diluted with ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether.Vinyl | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | Se | O1CCOCC1 | 60 | null | CC(=O)Nc1nc(C(=O)N(c2ccccc2)c2ccccc2)c2ncn(COCC[Se]c3ccccc3)c2n1>O1CCOCC1>C=COCn1cnc2c(C(=O)N(c3ccccc3)c3ccccc3)nc(NC(C)=O)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a66c33e4b2254f71b2ba86198e200a69 | CC(C)(C)C(=O)Cl.Nc1ncnc2c1ncn2[C@H]1CC=CO1>>CC(C)(C)C(=O)Nc1ncnc2c1ncn2[C@H]1CC=CO1 | CO.O1[C@H](CC=C1)N1C2=NC=NC(=C2N=C1)N.CC(C(=O)Cl)(C)C.C(Cl)Cl.CO>>O1[C@H](CC=C1)N1C2=NC=NC(=C2N=C1)NC(C(C)(C)C)=O | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[n:9][cH:10][n:11][c:12]2[c:13]1[n:14][cH:15][n:16]2[C@H:17]1[CH2:18][CH:19]=[CH:20][O:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[n:9][cH:10][n:11][c:12]2[c:13]1[n:14][cH:15][n:16]2[C@H:17]1[CH2:18][CH:19]=[CH:20][O:21]1 | CC(C)(C)C(=O)Cl.Nc1ncnc2c1ncn2[C@H]1CC=CO1 | CC(C)(C)C(=O)Nc1ncnc2c1ncn2[C@H]1CC=CO1 | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1=CO[C@@H](n2cnc3cncnc32)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:2:1>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[#7;a:13]:[c:14]:[#... | 94 | [{"value": 94.0, "product": "O1[C@H](CC=C1)N1C2=NC=NC(=C2N=C1)NC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 30 | MINUTE | To a suspension of the product of Step C (196 g, 0.97 mole), 4-dimethylaminopyridine (5.9 g, 0.048 mole) in dry pyridine (970 mL) at 26° C. was added dropwise over 1 hr trimethylacetylchloride (145 mL, 142.1 g, 1.18 mole, 1.2 equiv.). A slight 3° C. exotherm was noted. The reaction mixture was then heated to 55° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ncnc2nc[nH]c12.C1=COCC1 | HCl | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | 55 | 0.5 | CC(C)(C)C(=O)Cl.Nc1ncnc2c1ncn2[C@H]1CC=CO1>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>CC(C)(C)C(=O)Nc1ncnc2c1ncn2[C@H]1CC=CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f026b66c93374e7dacf2ff70e1bdeab8 | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>>O=C1CCC(c2ccc(Cl)cc2)=NN1 | ClC1=CC=C(C(=O)CCC(=O)O)C=C1.O.NN>>ClC1=CC=C(C=C1)C=1CCC(NN1)=O | [NH2:13][NH2:14].O=[C:5]([CH2:4][CH2:3][C:2](O)=[O:1])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1 | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | null | null | C(C)O | Acylation | OtherReaction | 16e715242dd5e92f711d46176c552652cef6c6f4fed9bc9a09a311d5b0b86cea | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])=[N;H0;D2;+0:9]-[NH;D2;+0:10]-1 | 81.5 | [{"value": 80.0, "product": "ClC1=CC=C(C=C1)C=1CCC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "ClC1=CC=C(C=C1)C=1CCC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=NNCCC1 | C1=NNCCC1.c1ccccc1 | HO- | C(C)O | null | null | NN.O=C(O)CCC(=O)c1ccc(Cl)cc1>C(C)O>O=C1CCC(c2ccc(Cl)cc2)=NN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1cec5adaec74900a26ae5c2339bc4da | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN>>CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O | ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1.C(C)(=O)[O-].[Na+].Cl.C(C)(C)(C)NN>>ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O | O=[C:7]([c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[CH:15]([CH3:16])[C:17](O)=[O:18].[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][NH2:6]>>[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[N:6]=[C:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[CH2:15][CH2:16][C:17]1=[O:18] | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN | CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O | null | null | C(CCC)O | Acylation | OtherReaction | 4e477d09c29dc9649665c2a512a7ab66ed0db9837b745e511eba3c76a3cc18d7 | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[CH3;D1;+0:4])-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:13]-[NH2;D1;+0:14]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[N;H0;D3;+0:13]1-[N;H0;D2;+0:14]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[CH2;D2;+0:3]-[CH2;D2;+... | 34.4 | [{"value": 34.4, "product": "ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=N[NH]CCC1 | C1=N[NH]CCC1.c1ccccc1 | HO- | C(CCC)O | null | null | CC(C(=O)O)C(=O)c1ccc(Cl)cc1.CC(C)(C)NN>C(CCC)O>CC(C)(C)N1N=C(c2ccc(Cl)cc2)CCC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4180ca501a3f4f4d860ac5334c81ecf5 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>>O=C(O)CCC(=O)c1cccc(Cl)c1 | C(CCC(=O)OC)(=O)OC.[Na].C(C)O.ClC=1C=C(C(=O)OC)C=CC1.C(CCC(=O)OC)(=O)OC>>ClC=1C=C(C(=O)CCC(=O)O)C=CC1 | COC(=O)[CH2:5][CH2:4][C:2](=[O:1])[O:3]C.CO[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]1 | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | null | null | CCOCC | C-C Coupling | OtherReaction | 6d482de2a0c1fffe47581cf2d6dc0eefca79628574252eec326be9292f335afe | 1f69704fe402a3eb0e91a243a59f68f972592be61b4c787368515903d4c85726 | c1ccccc1 | C-O-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C.C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H0:4]=[C:3](-[OH;D1;+0:5])-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Sodium (11 g, spheres) was added to 200 ml ethanol with stirring. When the gas evolution ceased, methyl 3-chlorobenzoate (10 g, 0.057 mole) and dimethyl succinate (9.0 g, 0.615 mole) were added rapidly and the mixture was stirred for 5 minutes at room temperature. The mixture was slowly concentrated on a rotary evapora... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Carboxylic acid.Ketone | null | null | c1ccccc1 | HO- | CCOCC | null | null | COC(=O)CCC(=O)OC.COC(=O)c1cccc(Cl)c1>CCOCC>O=C(O)CCC(=O)c1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6293fd2e9db947d781cf392334ab42c8 | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | CC1=CC=C(C(=O)CCC(=O)O)C=C1.[Cl-].[Al+3].[Cl-].[Cl-].ClCl>>ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl | [CH3:1][c:2]1[cH:3][cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][cH:15]1.[Cl:4][Cl:16]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([C:7](=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[OH:13])[cH:14][c:15]1[Cl:16] | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl | Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | d2a751fe92dcfde720edd5e4971c1aa6cc149bff4a6d230cc6b5cac59ec9498c | 861258def4b3bd7367f8a87cde43fe585d40dc3669ea29055dbcb9a2de101a4d | c1ccccc1 | [C;D1;H3:1]-[c:2]1:[cH;D2;+0:3]:[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[cH;D2;+0:9]:1.[Cl;H0;D1;+0:10]-[Cl;H0;D1;+0:11]>>[C;D1;H3:1]-[c:2]1:[c;H0;D3;+0:3](-[Cl;H0;D1;+0:10]):[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:11] | 44.2 | [{"value": 44.2, "product": "ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide.Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C(Cl)Cl | null | null | Cc1ccc(C(=O)CCC(=O)O)cc1.ClCl>C(Cl)Cl>Cc1c(Cl)cc(C(=O)CCC(=O)O)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fc69e41020da42a2a18c5933d3ff4b1f | C1=COCCC1.OCC#CCO>>OCC#CCOC1CCCCO1 | C(C#CCO)O.O1CCCC=C1>>O1C(CCCC1)OCC#CCO | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[OH:1][CH2:2][C:3]#[C:4][CH2:5][OH:6]>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.OCC#CCO | OCC#CCOC1CCCCO1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | CCOCC | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]#[C:9]-[C:10]-[OH;D1;+0:11]>>[C:7]-[C:8]#[C:9]-[C:10]-[O;H0;D2;+0:11]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | 68.8 | [{"value": 68.8, "product": "O1C(CCCC1)OCC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C.CCOCC | null | null | C1=COCCC1.OCC#CCO>C1(=CC=C(C=C1)S(=O)(=O)O)C.CCOCC>OCC#CCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a87607fbb9ca412d85516fecfc51ea39 | C#CC1CCCCC1.C=O>>OCC#CC1CCCCC1 | C1(CCCCC1)C#C.C=O.C=O>>C1(CCCCC1)C#CCO | [CH:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.[O:1]=[CH2:2]>>[OH:1][CH2:2][C:3]#[C:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | C#CC1CCCCC1.C=O | OCC#CC1CCCCC1 | null | null | CCOCC | C-C Coupling | OtherReaction | b068d8bba9f864ba971dd324292d9b3526f0235b4ab7e3a9ce6aa76a39c4a1e7 | 22ebec2cc94dd24863aea8793d450cfe0691e1036be204d1a4c79c16effe90a4 | C1CCCCC1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[C:3]-[C:4]#[CH;D1;+0:5]>>[C:3]-[C:4]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | To a solution of ethyl magesium bromide (prepared from 2.5 g of magnesium turning and 11.3 g of bromoethane) in ether was added dropwise a solution of 10.2 g of cyclohexylacetylene in ether and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and anhydrous formaldehy... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Alkyne | Primary alcohol.Alkyne | null | null | C1CCCCC1 | null | CCOCC | null | null | C#CC1CCCCC1.C=O>CCOCC>OCC#CC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a01b2f9c7fd648488efd533de927a930 | O=C1CCC(c2ccc(Cl)cc2)=NN1>>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1CCC(NN1)=O.C(C)(=O)O.BrBr>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)=[N:13][NH:14]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=C1CCC(c2ccc(Cl)cc2)=NN1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 73c80fbcc9dd7a9125aaf1059d9d4eab31b342d21fc860abf5e65fd78456864b | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1ccc(-c2ccccc2)n[nH]1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])=[N;H0;D2;+0:11]-[NH;D2;+0:12]-1>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[cH;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]):[n;H0;D2;+0:11]:[nH;D2;+0:12]:1 | 93.1 | [{"value": 89.0, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | C1=NNCCC1 | c1cccnn1 | c1cccnn1.c1ccccc1 | null | O | null | null | O=C1CCC(c2ccc(Cl)cc2)=NN1>O>O=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-07f806809672440ba2c325ca90047b96 | FC1(F)CC(Cl)(Cl)C1(F)Cl>>FC1(F)C=C(Cl)C1(F)Cl | ClC1(C(C(C1)(F)F)(F)Cl)Cl.O.Cl>>ClC1(C(C=C1Cl)(F)F)F | Cl[C:5]1([Cl:6])[CH2:4][C:2]([F:1])([F:3])[C:7]1([F:8])[Cl:9]>>[F:1][C:2]1([F:3])[CH:4]=[C:5]([Cl:6])[C:7]1([F:8])[Cl:9] | FC1(F)CC(Cl)(Cl)C1(F)Cl | FC1(F)C=C(Cl)C1(F)Cl | null | null | CCOCC.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | 0ca523bc88d44f4371960ac2ff9ed0bbb8882337b7061f7fba5b4787f1e02481 | 986b135105e7920109b424799136a4a8281fb4a0f49253ce1bf5d4426ed78637 | C1=CCC1 | Cl-[C;H0;D4;+0:1]1(-[Cl;D1;H0:2])-[CH2;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1]1=[CH;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7]-1(-[Cl;D1;H0:8])-[F;D1;H0:9] | 79 | [{"value": 79.0, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "ClC1(C(C=C1Cl)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ethe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | Alkenyl halide | C1CCC1 | C1=CCC1 | C1=CCC1 | HCl | CCOCC.C(C)N(CC)CC | null | 8 | FC1(F)CC(Cl)(Cl)C1(F)Cl>CCOCC.C(C)N(CC)CC>FC1(F)C=C(Cl)C1(F)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-12d76bd288204ab9895441c0ad284664 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>>O=C(O)C(F)C(F)(F)C(=O)O | ClC(C(C(=O)O)(F)F)(C(=O)O)F>>FC(C(=O)O)(C(C(=O)O)F)F | Cl[C:6]([C:4]([C:2](=[O:1])[OH:3])([F:5])[F:7])([F:8])[C:9](=[O:10])[OH:11]>>[O:1]=[C:2]([OH:3])[CH:4]([F:5])[C:6]([F:7])([F:8])[C:9](=[O:10])[OH:11] | O=C(O)C(F)(F)C(F)(Cl)C(=O)O | O=C(O)C(F)C(F)(F)C(=O)O | null | [Zn] | O1CCOCC1 | Functional Group Addition | Dehalogenation | 7f145230bfb0115349e969b2f2fa1359cfafe8c166e52b50a867192005e1f5bc | d6722b0df465660a9eeeaca5a8f5b3dbb2d1ebccb44917f2eca97a85bf850d06 | null | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;H0;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[F;D1;H0:7]-[CH;D3;+0:6](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;H0;D1;+0:8])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 40.7 | [{"value": 32.0, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "FC(C(=O)O)(C(C(=O)O)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Tertiary halide.Tertiary halide.Secondary halide | null | null | null | Other | [Zn].O1CCOCC1 | null | 10 | O=C(O)C(F)(F)C(F)(Cl)C(=O)O>[Zn].O1CCOCC1>O=C(O)C(F)C(F)(F)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-406ab0cccf234491959e2eb53d45aa2c | O=C1CCC(=O)O1.c1ccc2ccccc2c1>>O=C(O)CCC(=O)c1cccc2ccccc12 | Cl.[Cl-].[Cl-].[Cl-].[Al+3].C1=CC=CC2=CC=CC=C12.C1(CCC(=O)O1)=O>>C1(=CC=CC2=CC=CC=C12)C(=O)CCC(=O)O | [O:1]=[C:2]1[O:3][C:6](=[O:7])[CH2:5][CH2:4]1.[cH:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | O=C1CCC(=O)O1.c1ccc2ccccc2c1 | O=C(O)CCC(=O)c1cccc2ccccc12 | null | null | [N+](=O)([O-])C1=CC=CC=C1 | C-C Coupling | OtherReaction | d1b47ca78c3ceb45955ddf79d2b2d22c1a0978cf9fa8ded4c5ee0a8331deac4e | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccc2ccccc2c1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11](:[c:12]):[c:13]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | A mixture of naphthalene (40 g) and succinic anhydride (20 g) was added to a well stirred suspension of aluminum trichloride (55 g) in nitrobenzene (140 ml). The resulting mixture was stirred overnight at room temperature. The mixture was then poured slowly onto ice-water (600 g) and acidified with 6N-hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | C1CCOC1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | [N+](=O)([O-])C1=CC=CC=C1 | null | null | O=C1CCC(=O)O1.c1ccc2ccccc2c1>[N+](=O)([O-])C1=CC=CC=C1>O=C(O)CCC(=O)c1cccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f007d2f3c0154a719f2dd1d49dbba9b3 | NN.O=C(O)CCCC(=O)c1ccccc1>>O=c1cccc(-c2ccccc2)nn1 | C(C1=CC=CC=C1)(=O)CCCC(=O)O.NN.O>>C1(=CC=CC=C1)C1=CC=CC(N=N1)=O | [NH2:13][NH2:14].O=[C:6]([CH2:5][CH2:4][CH2:3][C:2](O)=[O:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[O:1]=[c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][n:14]1 | NN.O=C(O)CCCC(=O)c1ccccc1 | O=c1cccc(-c2ccccc2)nn1 | null | null | C1(=CC=CC=C1)C.CCOCC | Aromatic Heterocycle Formation | OtherReaction | a31553d36b14882561a6dcdd04ef456bc0e14ea189c472490f94f02ebbe3ca3f | eadf9e657b4bde18ed656e299092aac7dd81eee1face1030775c3edd6ccba31c | O=c1cccc(-c2ccccc2)nn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[NH2;D1;+0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[n;H0;D2;+0... | 39 | [{"value": 39.0, "product": "C1(=CC=CC=C1)C1=CC=CC(N=N1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | null | null | c1cccc[nH]n1 | c1cccc[nH]n1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.CCOCC | null | null | NN.O=C(O)CCCC(=O)c1ccccc1>C1(=CC=CC=C1)C.CCOCC>O=c1cccc(-c2ccccc2)nn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-38cbb1529cc84ed082175760bc576022 | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>>COC(=O)C1Cc2cc(Cl)ccc2C1=O | COC(OC)=O.[H-].[Na+].ClC=1C=C2CCC(C2=CC1)=O.[H][H]>>C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[C:14]1=[O:15] | COC(=O)OC.O=C1CCc2cc(Cl)ccc21 | COC(=O)C1Cc2cc(Cl)ccc2C1=O | null | null | C(OC)COC | C-C Coupling | OtherReaction | c2c31337dfb867d8c28bc65df0ad4496f817a712a58e176523b47d7fdb6e4f91 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | O=C1CCc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | 45 | [{"value": 45.0, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(OC)COC | 60 | null | COC(=O)OC.O=C1CCc2cc(Cl)ccc21>C(OC)COC>COC(=O)C1Cc2cc(Cl)ccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-247e413f02fe4dc189d56235735a1bdb | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>>CN(C)C=C(C=O)c1ccc(Cl)cc1 | C([O-])([O-])=O.[K+].[K+].P(=O)(Cl)(Cl)Cl.CN(C)C=O.ClC1=CC=C(C=C1)CC(=O)O>>ClC1=CC=C(C=C1)C(C=O)=CN(C)C | O=[CH:4][N:2]([CH3:1])[CH3:3].O=[C:6]([CH2:5][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[OH:7]>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([CH:6]=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1 | CN(C)C=C(C=O)c1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cbf378fe57a2b8d8304e623fb5ce9ee6fb9f6e90d9c6f965226d56b103180e6d | a9c635686380f13b6b5c45d80d4aef36b30fdab0aef140b81f04c277f7ba737d | c1ccccc1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6].O=[CH;D2;+0:7]-[#7:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[#7:8](-[C;D1;H3:10])-[CH;D2;+0:7]=[C;H0;D3;+0:3](-[CH;D2;+0:1]=[O;H0;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Enamine.Aldehyde | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 8 | CN(C)C=O.O=C(O)Cc1ccc(Cl)cc1>C1(=CC=CC=C1)C>CN(C)C=C(C=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-506fcc7b31c241b1b92a78d6c6e2a5ef | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | C(C)(=O)O.ClC1=CC=C(C=C1)C(C=O)=CN(C)C.C[O-].[Na+].C(#N)CC(=O)N>>C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O | CN(C)[CH:13]=[C:5]([CH:4]=O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[N:1]#[C:2][CH2:3][C:15]([NH2:14])=[O:16]>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14][c:15]1=[O:16] | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 4fb69599b2ad512416349de44ee025f314a8ccdb2c8ad729cdf94ea75cf3109a | 46cf335065eccd013987994a3f086665eb273ac87eb3153099a47e61dd329581 | O=c1ccc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[N;D1;H0:9]#[C:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:1]:[nH;D2;+0:13]:[c;H0;D3;+0... | null | [] | null | null | null | null | To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Primary amide | null | null | c1cnccc1 | c1cnccc1.c1ccccc1 | HO- | CO.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.N#CCC(N)=O>CO.O>N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a4f37788b1a484282d9cf4c25552db7 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)C=1C=CC(NC1)=O | N#C[c:3]1[c:2](=[O:1])[nH:14][cH:13][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:4]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O | O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 | null | null | OP(=O)(O)O | Miscellaneous | OtherReaction | 145adc421652def73603eb299eace1e2e3a197522b719b6949c0145a4308d11b | 4f08c5adfb6d80fba1093598fc51ce38f180c76537f67052d397b642cb6f3b89 | O=c1ccc(-c2ccccc2)c[nH]1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1 | 75.6 | [{"value": 75.6, "product": "ClC1=CC=C(C=C1)C=1C=CC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-cyano-5-(4-chlorophenyl)-2-pyridinone (4.6 g) and 85% H3PO4 (60 ml) was heated at reflux for 16 hours. The resulting mixture was cooled to room temperature, poured into ice/water and filtered yielding 3.1 g of 5-(4-chlorophenyl)-2-pyridinone as a yellow solid.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | c1cnccc1 | c1cccnc1 | c1cccnc1.c1ccccc1 | Other | OP(=O)(O)O | null | null | N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O>OP(=O)(O)O>O=c1ccc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3aaa2f0964b0473a962a140eaa35f34c | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | [Cl-].[NH4+].[H-].[Na+].N1C(C=CC=C1)=O.CCCCCC.C(C)(=O)OCC.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=CC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[CH2:9]([CH3:10])[CH2:15][CH2:14][CH2:12][CH3:11].[nH:6]1[cH:7][cH:8][cH:16][cH:17][c:18]1=[O:19].[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][cH:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-] | CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | c16e53991381708a0d74f5092b5e25b0353184189763eaae006dd565c1174ab9 | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ccc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10].[Cl-;H0;D0:11].[O;D1;H0:12]=[c:13]1:[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:6]2:[cH;D2;+0:5]:[cH;D2;+0:... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 200 mg) in dry DMF (50 ml) at 0° C. was added the preceding pyridinone and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne dropwise. The resulting mixture was kept at 0° C. during one half hour and poured into satura... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)ccc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0ed0a908d15a48e6b829b90b094e3f19 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | C(C)(=O)OCC.ClC1=CC=C(N)C=C1.N1=CC=CC=C1.C(C=CC1=CC=CC=C1)(=O)Cl>>ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.Cl[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | null | null | C1(=CC=CC=C1)C.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(C=Cc1ccccc1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]=[C:4]-[c:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | 0 | CELSIUS | 15 | MINUTE | To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.O | 0 | 0.25 | Nc1ccc(Cl)cc1.O=C(Cl)C=Cc1ccccc1>C1(=CC=CC=C1)C.O>O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-326a0eacbf2f4832bc99567ea0fb9504 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>>O=c1ccc2c(Cl)cccc2[nH]1 | ClC1=CC=C(C=C1)NC(C=CC1=CC=CC=C1)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>ClC1=C2C=CC(NC2=CC=C1)=O | c1ccc([CH:4]=[CH:3][C:2](=[O:1])[NH:12][c:11]2[cH:5][cH:8][c:6]([Cl:7])[cH:9][cH:10]2)cc1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]2[nH:12]1 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1 | O=c1ccc2c(Cl)cccc2[nH]1 | null | null | ClC1=CC=CC=C1 | Reduction | OtherReaction | ebe7e954f82f1e726cf9b7a8863216fec31733c3d8bfbb1cc71c49312cec65ac | 10d6d5b071f1d84b20b253ce9eadaed211c373c6ee607356078792f13319351a | O=c1ccc2ccccc2[nH]1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-c2:c:c:c:c:c:2):[c:11]:[cH;D2;+0:12]:1>>[Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:12]:[c:11]:[c:5]2:[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+... | null | [] | 125 | CELSIUS | 3 | HOUR | To a mixture of N-(4-chlorophenyl)cinnamamide (8.3 g), and chlorobenzene (60 ml) was added portionwise aluminum chloride (21.4 g) under nitrogen at room temperature and the reaction mixture was slowly warmed up to 125° C. and kept at that temperature for 3 hours. The reaction mixture was cooled down and poured over 400... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccc2ccccc2n1 | c1ccc2ccccc2n1 | Other | ClC1=CC=CC=C1 | 125 | 3 | O=C(C=Cc1ccccc1)Nc1ccc(Cl)cc1>ClC1=CC=CC=C1>O=c1ccc2c(Cl)cccc2[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bb2d977cc5f147c5ab274afa7d1d2d39 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>>CCC#CCn1c(=O)ccc2c(Cl)cccc21 | [Cl-].[NH4+].N1C(C=CC2=CC=CC=C12)=O.[H-].[Na+].BrCC#CCC>>ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].[nH:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[cH:12][cH:14][cH:15][cH:16][c:17]12.[Cl-:13]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[c:7](=[O:8])[cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12 | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-] | CCC#CCn1c(=O)ccc2c(Cl)cccc21 | null | null | CN(C)C=O.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a61336fe7a89ec0981a525297b55629e44e830f13f91df56a44bf01390d8c69d | dbda6588fa29cbbc0e3c3f601e69924b300990bdcc56b8cec0535d1258039346 | O=c1ccc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[Cl-;H0;D0:5].[O;D1;H0:6]=[c:7]1:[c:8]:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[c:15]:2:[nH;D2;+0:16]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:16]1:[c:15]2:[c:14]:[c:13]:[c:12]:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:5]):[c:10]:2:[c:9]:[c:8]:[c:7]:1=[O;D1;H0:6] | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and po... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccc2ccccc2n1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | CN(C)C=O.CCCCCC | 0 | null | CCC#CCBr.O=c1ccc2ccccc2[nH]1.[Cl-]>CN(C)C=O.CCCCCC>CCC#CCn1c(=O)ccc2c(Cl)cccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50a47b176604482395560ff8f1a4f880 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | [Cl-].[NH4+].ClC1=CC=C(C=C1)C(C=O)=CN(C)C.NC(=O)N.Cl>>ClC1=CC=C(C=C1)C=1C=NC(NC1)=O | CN(C)[CH:4]=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH:13]=O.[O:1]=[C:2]([NH2:3])[NH2:14]>>[O:1]=[c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][nH:14]1 | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O | O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | 0e1bb7c6fc2fa2fbd0239b648ae136ef123b13ddeb9947c50b8f38d453d7d183 | 55a949c5abf218b0e7fd0015b81e86fb975fa441e5ac6bd395c3346bb38599f7 | O=c1ncc(-c2ccccc2)c[nH]1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[CH;D2;+0:3]=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[O;D1;H0:12]>>[O;D1;H0:12]=[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:3]:[nH;D2;+0:9]:1 | 29.7 | [{"value": 29.7, "product": "ClC1=CC=C(C=C1)C=1C=NC(NC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Urea | null | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | C(C)O.O | null | null | CN(C)C=C(C=O)c1ccc(Cl)cc1.NC(N)=O>C(C)O.O>O=c1ncc(-c2ccc(Cl)cc2)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4cc12f6af27449db870b9f2027866d61 | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | [Cl-].[NH4+].CCCCCC.[H-].[Na+].N1C(C=CC=C1)=O.BrCC#CCC>>ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O | Br[CH2:5][C:4]#[C:3][CH2:2][CH3:1].C[CH2:15][CH2:14][CH2:12][CH2:11][CH3:10].[nH:6]1[cH:7][cH:8][cH:16][cH:9][c:18]1=[O:19].[Cl-:13].[NH4+:17]>>[CH3:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[cH:16][n:17][c:18]1=[O:19] | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+] | CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | b4467fdd65493649554b053844b88f7aedac75ecb5e83a2819a9163270cc6b1f | f1e2d48aa3857a2357f3a371c35806794fc7180cbbfa20a78f207e36837e33dc | O=c1ncc(-c2ccccc2)c[nH]1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].C-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH3;D1;+0:9].[Cl-;H0;D0:10].[NH4+;D0:11].[O;D1;H0:12]=[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c:17]:[nH;D2;+0:18]:1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:18]1:[c:17]:[c;H0;D3;+0:16](-[c;H0;D3;+0:14]2... | null | [] | 0 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and pour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aromatic halide | c1ccccn1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1 | HBr | CN(C)C=O | 0 | null | CCC#CCBr.CCCCCC.O=c1cccc[nH]1.[Cl-].[NH4+]>CN(C)C=O>CCC#CCn1cc(-c2ccc(Cl)cc2)cnc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e530c7df16024f4aae4797b4613d3ced | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | ClC1=CC=C(C=C1)C=1C=CC(NN1)=O.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClC1=CC=C(C=C1)C=1C=CC(NN1)=S | O=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:1])(S2)S3>>[S:1]=[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[n:13][nH:14]1 | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | e0da8be0c0e31372bc487fca4d998b8539b7ff5b84df07e1a6200efd3593e0bb | 13be3f637e1e22872d741944f46b7fcc1954fe982a3a8a0f7825545d455ab147 | S=c1ccc(-c2ccccc2)n[nH]1 | O=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:7])(-S-2)-S-3>>[S;H0;D1;+0:7]=[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 187.1 | [{"value": 187.1, "product": "ClC1=CC=C(C=C1)C=1C=CC(NN1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3×100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thiocarbonyl | c1cccnn1.S1P2SP3SP1SP(S2)S3 | c1cccnn1 | c1cccnn1.c1ccccc1 | Other | N1=CC=CC=C1 | null | null | O=c1ccc(-c2ccc(Cl)cc2)n[nH]1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>S=c1ccc(-c2ccc(Cl)cc2)n[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d8de4f9f5ac412ebeca703ef49f3390 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)NN)C=C1.ClCC(=O)Cl>>ClCC(=O)NNC(C1=CC=C(C=C1)Cl)=O | [NH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl | O=C(CCl)NNC(=O)c1ccc(Cl)cc1 | null | null | O1CCOCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9] | null | [] | null | null | null | null | To a solution of p-chlorobenzoic hydrazide (11.2 g) in dioxane (100 ml) was added chloroacetyl chloride (6 ml). The resulting mixture was refluxed for three hours, cooled to room temperature and filtered. The resulting solid was washed with ethyl ether and dried to yield N'-chloroacetyl-4-chlorobenzoic hydrazide as whi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1 | HCl | O1CCOCC1 | null | null | NNC(=O)c1ccc(Cl)cc1.O=C(Cl)CCl>O1CCOCC1>O=C(CCl)NNC(=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-10c1b8c1d0dd44818ead6ca91a1dbfb1 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>>O=C1NN=C(c2ccc(Cl)cc2)CS1 | BrCC(=O)C1=CC=C(C=C1)Cl.COC(=S)NN>>ClC1=CC=C(C=C1)C1=NNC(SC1)=O | C[O:1][C:2]([NH:3][NH2:4])=[S:14].O=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:13]Br>>[O:1]=[C:2]1[NH:3][N:4]=[C:5]([c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:13][S:14]1 | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1 | O=C1NN=C(c2ccc(Cl)cc2)CS1 | null | null | C(C)#N | Acylation | OtherReaction | a0815ff887854434f061e02bb59e65917f2f792eefe3f407e6f67a241e834044 | b7ddc8c969600ae9a9b2d12841c66a24307741bcbfc0810c56e58eb7d0e4892d | O=C1NN=C(c2ccccc2)CS1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].C-[O;H0;D2;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[#7:9]-[NH2;D1;+0:10]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[#7:9]-[N;H0;D2;+0:10]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-1 | 48.4 | [{"value": 48.4, "product": "ClC1=CC=C(C=C1)C1=NNC(SC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Ketone.Ether.Thioamide | Hydrazone amide.Monosulfide | null | C1=NNCSC1 | C1=NNCSC1.c1ccccc1 | HBr | C(C)#N | null | null | COC(=S)NN.O=C(CBr)c1ccc(Cl)cc1>C(C)#N>O=C1NN=C(c2ccc(Cl)cc2)CS1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93c4153772314fe5b6357b0fc7b230aa | O=C(O)CCC(=O)c1cccc(Cl)c1>>O=C(O)CCCc1cccc(Cl)c1 | ClC=1C=C(C(=O)CCC(=O)O)C=CC1.[OH-].[K+].NN>>ClC=1C=C(C=CC1)CCCC(=O)O | O=[C:6]([CH2:5][CH2:4][C:2](=[O:1])[OH:3])[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1 | O=C(O)CCC(=O)c1cccc(Cl)c1 | O=C(O)CCCc1cccc(Cl)c1 | null | null | C(COCCO)O | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9] | 90.8 | [{"value": 90.8, "product": "ClC=1C=C(C=CC1)CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 300 ml round-bottomed flask equipped with magnetic stirrer and reflux condenser was charged 23.7 g of 87% potassium hydroxide and 150 ml of diethyleneglycol, With stirring, 23 g of 3-(3-chlorobenzoyl)propionic acid was added followed by 24 g of 85% hydrazine. The mixture was heated to reflux for 2 hours when 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1 | Other | C(COCCO)O | null | null | O=C(O)CCC(=O)c1cccc(Cl)c1>C(COCCO)O>O=C(O)CCCc1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b13d649eb0e543419a54c9aec5175c91 | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1>>CN1N=C(c2ccc(Cl)cc2)CCC1=O | ClC1=CC=C(C(=O)CCC(=O)O)C=C1.CNN>>ClC1=CC=C(C=C1)C=1CCC(N(N1)C)=O | [CH3:1][NH:2][NH2:3].O=[C:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH2:12][CH2:13][C:14](O)=[O:15]>>[CH3:1][N:2]1[N:3]=[C:4]([c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[CH2:12][CH2:13][C:14]1=[O:15] | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1 | CN1N=C(c2ccc(Cl)cc2)CCC1=O | null | null | C(C)O | Acylation | OtherReaction | 4e477d09c29dc9649665c2a512a7ab66ed0db9837b745e511eba3c76a3cc18d7 | 30de68c4dde17a0553a43eee47b1b865b8390bb08557512a59e6e71e0ed0ad51 | O=C1CCC(c2ccccc2)=NN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](=O)-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH;D2;+0:10]-[NH2;D1;+0:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10]1-[N;H0;D2;+0:11]=[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-[C:4]-[C:3]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | To a 250 ml flask equipped with magnetic stirrer and reflux condenser was charged 10 g of 3-(4-chlorobenzoyl)-propionic acid, 250 ml. of absolute ethanol, and 2.5 ml of methyl hydrazine. The reaction was refluxed for 3 hours and cooled to yield a solid which was collected by vacuum filtration, washed with 50 ml of hexa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Ketone | Hydrazone amide | null | C1=N[NH]CCC1 | C1=N[NH]CCC1.c1ccccc1 | HO- | C(C)O | null | null | CNN.O=C(O)CCC(=O)c1ccc(Cl)cc1>C(C)O>CN1N=C(c2ccc(Cl)cc2)CCC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71f9c60234da4ab48aa5084c5a174dbb | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | ClC1=CC=C(C=O)C=C1.C(CCC(=O)C)(=O)O.N1CCCCC1.C1(=CC=CC=C1)C>>ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH3:8].O=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[CH:8]=[CH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1 | O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 | null | null | O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 44 | [{"value": 44.0, "product": "ClC1=CC=C(C=CC(=O)CCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)CCC(=O)O.O=Cc1ccc(Cl)cc1>O>O=C(O)CCC(=O)C=Cc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7eeb6357d2624e32bcc06f1bb1a4e975 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>>COc1ccc(C(=O)O)cc1[N+](=O)[O-] | [N+](=O)([O-])C=1C(=C(C(=O)[O-])C=CC1OC)C.[OH-].[K+]>>[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC | C[c:10]1[c:6]([C:7](=[O:8])[O-:9])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-] | COc1ccc(C(=O)O)cc1[N+](=O)[O-] | null | null | O1CCCC1 | Miscellaneous | OtherReaction | ec2bcf645eed3485ae21dd491bac7887e7ecc8e6727067de36c08c87eaa3e98c | d003579d88c8e6390ed4fac608b8ce68d334559ff02e2f3d9c9936750b60a874 | c1ccccc1 | C-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]):[c:9]>>[#7;+:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7]):[c:9] | 76.6 | [{"value": 76.6, "product": "[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a 500 ml erlenmeyer flask with magnetic stirrer was charged 10.3 g of 3-nitro-4-methoxy-methylbenzoate, 400 ml tetrahydrofuran, and 3.2 g of 86% potassium hydroxide. The reaction was stirred for 12 hours at ambient temperature, after which the resulting solid was collected by vacuum filtration and washed with 2×100 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCCC1 | null | 12 | COc1ccc(C(=O)[O-])c(C)c1[N+](=O)[O-]>O1CCCC1>COc1ccc(C(=O)O)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eff2bc0de6514ad8b023fb68fc66d9c2 | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1>>N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 | FC(C(=O)O)(F)F.N([C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)OC>>N[C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1.FC(F)(F)C(=O)O | CC(C)(C)OC(=O)[NH:1][C@H:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][C@H:16]1[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[NH2:1][C@H:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][C@H:16]1[C:... | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 | N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(OCc1ccccc1)[C@@H]1CCCN1C(=O)CCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11]>>[#8:10]-[C:9](=[O;D1;H0:11])-[C:8]-[#7:6](-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1])-[C:7] | 85 | [{"value": 85.0, "product": "N[C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1.FC(F)(F)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirring solution of Boc-D-Phe-Pro-OBn (68 g, 150 mmol) in dichloromethane (50 mL) at 0° C., was added anisole (20 mL) followed by trifluoroacetic acid (400 mL). After stirring for 3 hours, the solvents were evaporated in vacuo and the thick oily residue was dissolved in diethyl ether (1.5 L) and refrigerated (72 ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | ClCCl | null | 3 | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1>ClCCl>N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-75f289d130c7444bbf7348c68b3481f5 | O=C(O)[C@@H]1CCCN1.O=C(O)[C@H]1CCCCN1C(=O)OCc1ccccc1>>O=C(O)[C@@H]1CCCN1C(=O)[C@H]1CCCCN1C(=O)OCc1ccccc1 | N1([C@@H](C(=O)O)CCCC1)C(=O)OCC1=CC=CC=C1.ClC1=C(C=C(C(=C1)Cl)Cl)O.N1[C@H](C(=O)O)CCC1.C(C)N(CC)CC.C1(CCCCC1)N=C=NC1CCCCC1>>N1([C@@H](C(=O)N2[C@H](C(=O)O)CCC2)CCCC1)C(=O)OCC1=CC=CC=C1 | [O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8]1.O[C:9](=[O:10])[C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:10])[C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:17](=[... | O=C(O)[C@@H]1CCCN1.O=C(O)[C@H]1CCCCN1C(=O)OCc1ccccc1 | O=C(O)[C@@H]1CCCN1C(=O)[C@H]1CCCCN1C(=O)OCc1ccccc1 | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C([C@H]1CCCCN1C(=O)OCc1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9].[O;D1;H0:10]=[C:11](-[O;D1;H1:12])-[C:13]1-[C:14]-[C:15]-[C:16]-[NH;D2;+0:17]-1>>[#8:7]-[C:6](=[O;D1;H0:8])-[#7:5](-[C:9])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:17]1-[C:16]-[C:15]-[C:14]-[C:13]-1-[C:11](=[O;D1;H0:10])-[O;D1... | null | [] | 0 | CELSIUS | 1 | HOUR | Cbz-D-hPro-OH (9.5 g, 36 mmol) was dissolved in ethyl acetate (100 mL) and the solution cooled to 0° C. Added to the solution was 2,4,5-trichlorophenol (7.1 g, 36 mmol) and 1,3-dicyclohexylcarbodiimide (7.4 g, 36 mmol). The reaction was stirred for 1 hour at 0° C. and 1 hour at room temperature. The precipitate was fil... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.C1CC[NH]CC1.c1ccccc1 | HO- | C(C)(=O)OCC | 0 | 1 | O=C(O)[C@@H]1CCCN1.O=C(O)[C@H]1CCCCN1C(=O)OCc1ccccc1>C(C)(=O)OCC>O=C(O)[C@@H]1CCCN1C(=O)[C@H]1CCCCN1C(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e27f2076ea2944b58cddfe057fe8345b | O=C(O)c1nccc2ccccc12>>O=C(O)C1NCCC2CCCCC21 | C1(=NC=CC2=CC=CC=C12)C(=O)O.[H][H]>>C1(NCCC2CCCCC12)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[n:5][cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[O:1]=[C:2]([OH:3])[CH:4]1[NH:5][CH2:6][CH2:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]12 | O=C(O)c1nccc2ccccc12 | O=C(O)C1NCCC2CCCCC21 | null | [Rh] | Cl.CCO | Reduction | OtherReaction | 9d4ceb2330349e47c2f1e6d3fa94e6f87fe5387baf3dc326c222e39cbecb1d6e | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCC2CNCCC2C1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]2:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1:2>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4]1-[NH;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH;D3;+0:8]2-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+... | 56.8 | [{"value": 48.0, "product": "C1(NCCC2CCCCC12)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "C1(NCCC2CCCCC12)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-isoquinolinecarboxylic acid (50 g, 0.288 mol) in EtOH (150 mL) and 60 mL of 5N HCl was reduced over 5% Rh/Al2O3 (14 g) at 52 bar (750 psi) of hydrogen in a high pressure apparatus at 50° C. for 17 hours. The reaction mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentr... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2cnccc2c1 | C1CCC2CNCCC2C1 | C1CCC2CNCCC2C1 | null | [Rh].Cl.CCO | null | null | O=C(O)c1nccc2ccccc12>[Rh].Cl.CCO>O=C(O)C1NCCC2CCCCC21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d52eb0d907f4438189c898a207603691 | CCO.O=C(O)[C@@H]1Cc2ccccc2N1>>CCOC(=O)[C@@H]1Cc2ccccc2N1 | Cl.N1[C@@H](CC2=CC=CC=C12)C(=O)O.C(C)O>>C(C)OC(=O)[C@H]1NC2=CC=CC=C2C1 | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[C@@H:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[NH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[NH:14]1 | CCO.O=C(O)[C@@H]1Cc2ccccc2N1 | CCOC(=O)[C@@H]1Cc2ccccc2N1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccc2c(c1)CCN2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[c:6].[C;D1;H3:7]-[C:8]-[OH;D1;+0:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C;D1;H3:7])-[#7:5]-[c:6] | null | [] | null | null | 16 | HOUR | HCl gas was bubbled through a stirring suspension of (S)-indoline-2-carboxylic acid (20 g, 110 mmol) in ethanol (500 mL). When the acid was completely dissolved, the solution was brought to reflux. After 16 hours, the solution was cooled and the solvent removed in vacuo. The residue was triturated with diethyl ether an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccc2c(c1)CCN2 | HO- | null | null | 16 | CCO.O=C(O)[C@@H]1Cc2ccccc2N1>>CCOC(=O)[C@@H]1Cc2ccccc2N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6423112fc5f740f1b81f8bc3b9883d73 | COC(=O)/C=C/c1ccc(C#N)cc1>>COC(=O)CCc1ccc(C#N)cc1 | C(#N)C1=CC=C(/C=C/C(=O)OC)C=C1>>C(#N)C1=CC=C(CCC(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:6]/[c:7]1[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]1 | COC(=O)/C=C/c1ccc(C#N)cc1 | COC(=O)CCc1ccc(C#N)cc1 | null | [Pd].[O-]S(=O)(=O)[O-].[Ba+2] | C1(=CC=CC=C1)C | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[CH;D2;+0:5]=[CH;D2;+0:6]/[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9] | 77 | [{"value": 77.0, "product": "C(#N)C1=CC=C(CCC(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "C(#N)C1=CC=C(CCC(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 9 | HOUR | To a solution of methyl p-cyano-trans-cinnamate (13.6 g, 73 mmol) in toluene (485 mL) was added 5% Pd/BaSO4 (2.7 g). After 9 hours under hydrogen gas at 4 bar (60 psi), the solution was filtered, concentrated in vacuo and chromatographed over silica gel, eluting with a step gradient of hexanes through 30% ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1 | null | [Pd].[O-]S(=O)(=O)[O-].[Ba+2].C1(=CC=CC=C1)C | null | 9 | COC(=O)/C=C/c1ccc(C#N)cc1>[Pd].[O-]S(=O)(=O)[O-].[Ba+2].C1(=CC=CC=C1)C>COC(=O)CCc1ccc(C#N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83a8bb81a8d64ea092985f3237412bba | CC(C)(C)OC(=O)NCc1ccc([N+](=O)[O-])cc1>>CC(C)(C)OC(=O)NCc1ccc(N)cc1 | [BH4-].[Na+].C(=O)(OC(C)(C)C)NCC1=CC=C(C=C1)[N+](=O)[O-].[BH4-].[Na+]>>C(=O)(OC(C)(C)C)NCC1=CC=C(C=C1)N | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:16][cH:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]1 | CC(C)(C)OC(=O)NCc1ccc([N+](=O)[O-])cc1 | CC(C)(C)OC(=O)NCc1ccc(N)cc1 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97 | [{"value": 97.0, "product": "C(=O)(OC(C)(C)C)NCC1=CC=C(C=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "C(=O)(OC(C)(C)C)NCC1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirring solution of p-BocNHCH2C6H4NO2 (7.5 g, 29.7 mmol) and NiCl2.6H2O (17.7 g, 74.3 mmol) in methanol (150 mL) at 0° C. was added NaBH4 (5.6 g, 149 mmol) in small portions over 30 min. After complete addition of NaBH4 and 15 min, the solvent was evaporated in vacuo and the residue was dissolved in conc. ammoniu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CO | null | null | CC(C)(C)OC(=O)NCc1ccc([N+](=O)[O-])cc1>CO>CC(C)(C)OC(=O)NCc1ccc(N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbd17ea5df144cd0a50c633bd92af129 | COC(=O)Cl.NCCc1ccccc1>>COC(=O)NCCc1ccccc1 | Cl.C(CC1=CC=CC=C1)N.C(C)N(CC)CC.ClC(=O)OC>>COC(=O)NCCC1=CC=CC=C1 | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | COC(=O)Cl.NCCc1ccccc1 | COC(=O)NCCc1ccccc1 | null | null | C1CCOC1.C(C)OCC | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 95 | [{"value": 95.0, "product": "COC(=O)NCCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "COC(=O)NCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of phenethylamine (75.2 mL, 0.6 mol) and triethylamine (83 mL, 0.6 mol) in THF (500 mL) was added slowly methyl chloroformate 46.2 mL, 0.6 mol) dissolved in THF (50 mL). After the reaction was stirred for an additional 1 h at room temperature, diethyl ether (2 L) and 1N HCl (800 mL) were added. Th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | C1CCOC1.C(C)OCC | null | 1 | COC(=O)Cl.NCCc1ccccc1>C1CCOC1.C(C)OCC>COC(=O)NCCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-270d72865aa54cd2959c3b0657ef5d22 | CC[O-].COC(=O)N1CCC2CCCCC2C1C(=O)OC(C)(C)C>>CCOC(=O)C1C2CCCCC2CCN1C(=O)OC | C(C)(C)(C)OC(=O)C1N(CCC2CCCCC12)C(=O)OC.[O-]CC.[Na+]>>C(C)OC(=O)C1N(CCC2CCCCC12)C(=O)OC | [CH3:1][CH2:2][O-:3].CC(C)(C)O[C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[O:18][CH3:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[O:18][CH3:19] | CC[O-].COC(=O)N1CCC2CCCCC2C1C(=O)OC(C)(C)C | CCOC(=O)C1C2CCCCC2CCN1C(=O)OC | null | null | CCO | Acylation | OtherReaction | 3cc7d733b384e9ba94618e0e6dfcbd720d0785c06391bc57e0b5b74973c7cb95 | 42b1bb1596c614df074e57dead0e958643c9c7a196d5946ef0b85c6ac72e94d6 | C1CCC2CNCCC2C1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9].[C;D1;H3:10]-[C:11]-[O-;H0;D1:12]>>[#8:7]-[C:6](=[O;D1;H0:8])-[#7:5](-[C:9])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:12]-[C:11]-[C;D1;H3:10])-[C:4] | 95.2 | [{"value": 0.95, "product": "C(C)OC(=O)C1N(CCC2CCCCC12)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "C(C)OC(=O)C1N(CCC2CCCCC12)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester (81.2 g, 273 mmol) in EtOH (500 mL) was added sodium ethoxide (21% in ethanol) (88.4 mL, 273 mmol) and the reaction mixture was refluxed (24 h). The organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Ester | null | null | C1CCC2C[NH]CCC2C1 | HO- | CCO | null | null | CC[O-].COC(=O)N1CCC2CCCCC2C1C(=O)OC(C)(C)C>CCO>CCOC(=O)C1C2CCCCC2CCN1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-38e1d602a0364020bf23b6b6c882b7cf | N#Cc1cccs1.O=C=O>>N#Cc1ccc(C=O)s1 | CN(C=O)C.C(CCC)[Li].C(CC(O)(C(=O)O)CC(=O)O)(=O)O.S1C(=CC=C1)C#N.C(=O)=O.CC(=O)C.C(C)(C)NC(C)C>>C(#N)C=1SC(=CC1)C=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][s:9]1.O=[C:7]=[O:8]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[s:9]1 | N#Cc1cccs1.O=C=O | N#Cc1ccc(C=O)s1 | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | 05aa40df6ec4f7da1e5627875219c10c948fc22ad67059603c674615270a006e | 3c6b0d8e5d1da1ba2dcb896a8f9334c1841604d7035e307445ba5ecf475b5051 | c1ccsc1 | O=[C;H0;D2;+0:1]=[O;D1;H0:2].[#16;a:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:7]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1 | 84 | [{"value": 84.0, "product": "C(#N)C=1SC(=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a flame-dried 3 neck 1 L round bottom flask was added diisopropylamine (9 mL, 66 mmol) and THF (150 mL) under a nitrogen atmosphere. The flask was cooled to an internal temperature of -78° C. (dry ice/acetone). To this stirring solution was added n-butyllithium (1.6M in hexanes, 41.3 mL, 66.1 mmol) via syringe and t... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Aldehyde | c1ccsc1 | c1ccsc1 | c1ccsc1 | Other | C1CCOC1.O | null | 0.083333 | N#Cc1cccs1.O=C=O>C1CCOC1.O>N#Cc1ccc(C=O)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1b67cc5004d4967b21c8097f4c0e66d | N#Cc1ccc(C=O)s1>>N#Cc1ccc(CO)s1 | C(#N)C=1SC(=CC1)C=O.[BH4-].[Na+]>>C(#N)C=1SC(=CC1)CO | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[s:9]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[s:9]1 | N#Cc1ccc(C=O)s1 | N#Cc1ccc(CO)s1 | null | null | CCO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccsc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6] | 88 | [{"value": 88.0, "product": "C(#N)C=1SC(=CC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "C(#N)C=1SC(=CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 2-cyano-5-formyl-thiophene (6.9 g, 50 mmol) in EtOH (100 mL) was added sodium borohydride (1.9 g, 50 mmol) in portions. After 5 min of stirring, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and brine. The layers were separated and the organic phase was washed o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccsc1 | null | CCO | null | 0.083333 | N#Cc1ccc(C=O)s1>CCO>N#Cc1ccc(CO)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69104add2a2849aba17decff43b8a344 | BrC(Br)(Br)Br.N#Cc1ccc(CO)s1>>N#Cc1ccc(CBr)s1 | C(#N)C=1SC(=CC1)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br>>C(#N)C=1SC(=CC1)CBr | BrC(Br)(Br)[Br:8].O[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[s:9]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Br:8])[s:9]1 | BrC(Br)(Br)Br.N#Cc1ccc(CO)s1 | N#Cc1ccc(CBr)s1 | null | null | C1CCOC1 | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccsc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6] | 75 | [{"value": 75.0, "product": "C(#N)C=1SC(=CC1)CBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.8, "product": "C(#N)C=1SC(=CC1)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-cyano-5-(hydroxymethyl)thiophene (6.0 g, 43 mmol) in THF (50 mL) was added triphenylphosphine (15.7 g, 47 mmol) and carbon tetrabromide (12.3 g, 47 mmol). After stirring overnight under nitrogen atmosphere at room temperature, the solvent was removed in vacuo and the residue was dissolved in chlorofo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccsc1 | HBr | C1CCOC1 | null | 8 | BrC(Br)(Br)Br.N#Cc1ccc(CO)s1>C1CCOC1>N#Cc1ccc(CBr)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-47a44d0423b048a0ba771f9e6b7956a7 | CC#CCO.O=C(O)C1CN=CNC1>>CC#CCOC(=O)C1CN=CNC1 | Cl.N1C=NCC(C1)C(=O)O.C(C(=O)Cl)(=O)Cl.C(C#CC)O>>C(C#CC)OC(=O)C1CN=CNC1 | [CH3:1][C:2]#[C:3][CH2:4][OH:5].O[C:6](=[O:7])[CH:8]1[CH2:9][N:10]=[CH:11][NH:12][CH2:13]1>>[CH3:1][C:2]#[C:3][CH2:4][O:5][C:6](=[O:7])[CH:8]1[CH2:9][N:10]=[CH:11][NH:12][CH2:13]1 | CC#CCO.O=C(O)C1CN=CNC1 | CC#CCOC(=O)C1CN=CNC1 | null | null | C1=CC=CC=C1.O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | C1=NCCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[#7:5])-[C:6]-[#7:7].[C;D1;H3:8]-[C:9]#[C:10]-[C:11]-[OH;D1;+0:12]>>[#7:7]-[C:6]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:12]-[C:11]-[C:10]#[C:9]-[C;D1;H3:8])-[C:4]-[#7:5] | 61 | [{"value": 61.0, "product": "C(C#CC)OC(=O)C1CN=CNC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,4,5,6-tetrahydropyrimidine-5-carboxylic acid hydrochloride (1 g, 6 mmol) was suspended in a solution of oxalyl chloride (1.5 mL, 17 mmol) in benzene (10 mL), heated with stirring under reflux for 2.5 h, and then evaporated to dryness in vacuo after cooling, to give an orange-yellow residue. A mixture of the acid chlo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1=NCCCN1 | HO- | C1=CC=CC=C1.O | null | null | CC#CCO.O=C(O)C1CN=CNC1>C1=CC=CC=C1.O>CC#CCOC(=O)C1CN=CNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8b34ec462304b808abfb14a00d8380b | N#Cc1ccc(CBr)cc1.O=C1NCCN1>>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | O.BrCC1=CC=C(C#N)C=C1.[H-].[Na+].N1C(NCC1)=O>>O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23]1.[NH:8]1[CH2:9][CH2:15][NH:11][C:21]1=[O:22]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]3)[C:21]2=[O:22])[cH:23][cH:24]1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1 | N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 39571f641692bae0ab2e4fb7e56baf0a046bbe68e5d15065d8f936b61702d85c | 04064b000c1f037cb6379c4a9b891971302bcd094d2302ea56061b3b37327222 | O=C1N(Cc2ccccc2)CCN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1>>[C:11]-[c:12](:[c:13]):[cH;D2;+0:8]:[c:14]:[c:15]-[C:16]-[N;H0;D3;+0:7]1-[C:17]-[CH2;D2;+0:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:6]-1=[O;D1;H0:5] | null | [] | null | null | 1 | HOUR | To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea.Nitrile | C1CNCN1 | C1C[NH]C[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | Br- | CN(C=O)C | null | 1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>CN(C=O)C>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e3fd8b3d0bbc4562bc1152c1b8ade224 | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.BrCC=1C=C(C#N)C=CC1.[H-].[Na+]>>C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:27]1.[nH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[nH:24][c:25]1=[O:26]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:1... | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, 2 mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C=O)C | null | null | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C=O)C>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72c771861dac4179880db9f695399653 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | Cl.C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.[H-].[Na+].BrCC=1C=C(C(=O)OC)C=CC1>>COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:29]1.[nH:11]1[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[nH:26][c:27]1=[O:28]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][n:11]2[c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:... | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 25 | [{"value": 25.0, "product": "COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DM... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C)C=O | 50 | 0.5 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C)C=O>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d584948385474449aadf00017badca74 | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O.BrCC1=CC=C2C=CC(=CC2=C1)C#N>>C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O | Br[CH2:25][c:26]1[cH:27][cH:28][c:29]2[cH:30][cH:31][c:32]([C:33]#[N:34])[cH:35][c:36]2[cH:37]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[nH:24][c:38]2=[O:39])[cH:40]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6... | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1n(Cc2ccccc2)c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:1=[O;D1;H0:13] | null | [] | null | null | null | null | In a manner similar to Preparation 2 above, 3-[(2,3-dihydro4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)-naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3)8.05 (s,1), 7.9... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.c1c[nH]cn1 | HBr | null | null | null | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d0f3e38e8aab4374bc8286880e180242 | CCOC(=O)c1cn(C2Cc3ccccc3C2=O)c(C(=O)OCC)n1.[NH4+]>>CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3 | C(C)(=O)[O-].[NH4+].O=C1C(CC2=CC=CC=C12)N1C(=NC(=C1)C(=O)OCC)C(=O)OCC>>O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3)C=C(N2)C(=O)OCC | CCO[C:12](=[O:13])[c:14]1[n:8]([CH:9]2[C:10](=O)[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[CH2:22]2)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:15]1.[NH4+:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]2[c:9]3[c:10]([nH:11][c:12](=[O:13])[c:14]2[n:15]1)-[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[CH2:22]3 | CCOC(=O)c1cn(C2Cc3ccccc3C2=O)c(C(=O)OCC)n1.[NH4+] | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 81592ab7f3ddbb1f56ea7a979fdc4c2449d437c2d54c1a03e34c3c798f871052 | 90d91da8fe4a4df48cab6f211982834fddab85bdecacddc95412489737467fb5 | O=c1[nH]c2c(n3ccnc13)Cc1ccccc1-2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9]:[#7;a:10]:1-[CH;D3;+0:11]1-[C:12]-[c:13](:[c:14]):[c;H0;D3;+0:15](:[c:16]:[c:17])-[C;H0;D3;+0:18]-1=O.[NH4+;D0:19]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[#7;a:4]:[c:3]2:[#7;a:10](:[c:9]:1):[c;H0;D3;+0:11]1:[c;H0;D3;+0:18](:[nH;D2;+... | 37.7 | [{"value": 37.7, "product": "O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3)C=C(N2)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 51.2 g of ammonium acetate are added in small portions to a solution of 2 g of diethyl 1-(1-oxoindan-2-yl)imidazole-2,4-dicarboxylate in 80 ml of acetic acid and the mixture is heated to reflux for 2 hours. After cooling to a temperature close to 20° C. the precipitate formed is filtered off and rinsed with distilled w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | null | c1c[nH]cn1.c1ccc2c(c1)CCC2 | c1cn2c3c(ncc2n1)c1ccccc1C3 | c1cn2c3c(ncc2n1)c1ccccc1C3 | HO- | C(C)(=O)O | null | null | CCOC(=O)c1cn(C2Cc3ccccc3C2=O)c(C(=O)OCC)n1.[NH4+]>C(C)(=O)O>CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-285176e937a841c4943a04d3364e6c62 | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccc(N)cc1C3.CN=C=O>>CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccc(NC(=O)NC)cc1C3 | CN=C=O.NC1=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)OCC)=O)C2C=C1>>CNC(NC1=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)OCC)=O)C2C=C1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]2[c:9]3[c:10]([nH:11][c:12](=[O:13])[c:14]2[n:15]1)-[c:16]1[cH:17][cH:18][c:19]([NH2:20])[cH:25][c:26]1[CH2:27]3.[C:21](=[O:22])=[N:23][CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]2[c:9]3[c:10]([nH:11][c:12](=[O:13])[c:14]2[n:15]1)-[c:16]1[cH:17][cH:18][c:1... | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccc(N)cc1C3.CN=C=O | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccc(NC(=O)NC)cc1C3 | null | null | CN(C=O)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=c1[nH]c2c(n3ccnc13)Cc1ccccc1-2 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 12 | HOUR | 0.44 ml of methyl isocyanate is added dropwise with stirring to a suspension of 580 mg of ethyl 8-amino-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in 10 ml of dimethylformamide and stirring is continued for 12 hours at a temperature close to 20° C. The reaction mixture is then filtered, rin... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)Cc1c2ncc2nccn12 | null | CN(C=O)C | null | 12 | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccc(N)cc1C3.CN=C=O>CN(C=O)C>CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccc(NC(=O)NC)cc1C3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e4f280544c164e7781c5e91559bf59d4 | CCOC(=O)c1cn(C2Cc3ccc(Cl)cc3C2=O)c(C(=O)OCC)n1.[NH4+]>>CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1cc(Cl)ccc1C3 | ClC1=CC=C2CC(C(C2=C1)=O)N1C(=NC(=C1)C(=O)OCC)C(=O)OCC.C(C)(=O)[O-].[NH4+].C(C)(=O)O>>ClC=1C=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)OCC)=O)C2C1 | CCO[C:12](=[O:13])[c:14]1[n:8]([CH:9]2[C:10](=O)[c:16]3[cH:17][c:18]([Cl:19])[cH:20][cH:21][c:22]3[CH2:23]2)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:15]1.[NH4+:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]2[c:9]3[c:10]([nH:11][c:12](=[O:13])[c:14]2[n:15]1)-[c:16]1[cH:17][c:18]([Cl:19])[cH:20][cH:21][c:2... | CCOC(=O)c1cn(C2Cc3ccc(Cl)cc3C2=O)c(C(=O)OCC)n1.[NH4+] | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1cc(Cl)ccc1C3 | null | null | C(C)#N.CO.CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 61c7ec55b0cda76461d1bc06479dacee3533b147a8fd30112bef8bce93ad32d8 | 90d91da8fe4a4df48cab6f211982834fddab85bdecacddc95412489737467fb5 | O=c1[nH]c2c(n3ccnc13)Cc1ccccc1-2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9]:[#7;a:10]:1-[CH;D3;+0:11]1-[C:12]-[c:13](:[c:14]):[c;H0;D3;+0:15](:[c:16]:[c:17])-[C;H0;D3;+0:18]-1=O.[NH4+;D0:19]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[#7;a:4]:[c:3]2:[#7;a:10](:[c:9]:1):[c;H0;D3;+0:11]1:[c;H0;D3;+0:18](:[nH;D2;+... | 61.7 | [{"value": 61.7, "product": "ClC=1C=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)OCC)=O)C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is as in Example 1 but starting from 5 g of diethyl 1-(6-chloro-1-oxoindan-2-yl)imidazole-2,4-dicarboxylate, 118 g of ammonium acetate and 190 ml of acetic acid. After washing the precipitate with water and then with methyl ethyl ketone, the solid obtained is first of all ground in acetonitrile and then i... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | null | c1c[nH]cn1.c1ccc2c(c1)CCC2 | c1ccc2c(c1)c1ncc3nccn3c1C2 | c1ccc2c(c1)c1ncc3nccn3c1C2 | HO- | C(C)#N.CO.CC(=O)C | null | null | CCOC(=O)c1cn(C2Cc3ccc(Cl)cc3C2=O)c(C(=O)OCC)n1.[NH4+]>C(C)#N.CO.CC(=O)C>CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1cc(Cl)ccc1C3 |
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