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-cebc848bbe99485aaab1cf4393713d41 | BrCCCCCBr.CCOCn1cnc2[nH]c(=O)[nH]c(=O)c21>>CCOCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C | C(C)OCN1C=NC=2NC(NC(C12)=O)=O.BrCCCCCBr.C([O-])([O-])=O.[K+].[K+]>>BrCCCCCN1C(=O)N(C=2N=CN(C2C1=O)COCC)C | Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18].[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:19](=[O:20])[nH:21]2>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18])[c:19](=[O:20])[n:21]2[CH3:22] | BrCCCCCBr.CCOCn1cnc2[nH]c(=O)[nH]c(=O)c21 | CCOCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[nH;D2;+0:9]:[c:10](=[O;D1;H0:11]):[nH;D2;+0:12]:[c:13](=[O;D1;H0:14]):[c:15]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:13](=[O;D1;H0:14]):[c:15]2:[#7;a:5](-[C:4]):[c:6]:[#7;a:7]:[c:8]:2:[n;H0;D3;+0:9](-[C;D1;H3:16]):[c:10]:1=[O;D1;H0:11] | null | [] | null | null | null | null | 22.4 g (0.1 mol) of 7-ethoxymethylxanthine were stirred at 70° C. for 1.5 hours with 45.9 g (0.2 mol) of 1,5-dibromopentane and 27.6 g of activated potassium carbonate. The solution was filtered and concentrated, and the oily residue which remained was chromatographed (eluent: ethyl acetate).
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | null | null | null | null | BrCCCCCBr.CCOCn1cnc2[nH]c(=O)[nH]c(=O)c21>>CCOCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aad289277c9f4d77a324e372db09a54a | CCOCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C.CCOP([O-])OCC>>CCOCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C | P(OCC)(OCC)[O-].[H-].[Na+].BrCCCCCN1C(=O)N(C=2N=CN(C2C1=O)COCC)C>>C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCCCP(OCC)(OCC)=O)=O)C | Br[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][n:12]1[c:10](=[O:11])[c:9]2[n:5]([CH2:4][O:3][CH2:2][CH3:1])[cH:6][n:7][c:8]2[n:28]([CH3:29])[c:26]1=[O:27].[P:18]([O-:19])([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15][CH2:... | CCOCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C.CCOP([O-])OCC | CCOCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#8:5]-[P;H0;D3;+0:6](-[O-;H0;D1:7])-[#8:8]-[C:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[P;H0;D4;+0:6](=[O;H0;D1;+0:7])(-[#8:5]-[C:4])-[#8:8]-[C:9] | null | [] | 20 | CELSIUS | 0.5 | HOUR | 4.8 g (0.035 mol) of diethyl phosphite were cooled to 0° C. in 100 ml of dry dimethylformamide and slowly treated with 0.8 g (0.035 mol) of sodium hydride. The solution was stirred at 20° C. for 0.5 hours to complete the deprotonation and then treated with 10 g (0.0268 mol) of 1-(5-bromopentyl)-7-ethoxymethyl-3-methylx... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ncc2[nH]cnc2n1 | Br- | CN(C=O)C | 20 | 0.5 | CCOCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C.CCOP([O-])OCC>CN(C=O)C>CCOCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a73ebc6ee1142a2b1d6a7f2d536cdea | CCCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C.CCOP([O-])OCC>>CCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C | BrCCCCCN1C(=O)N(C=2N=CN(C2C1=O)CCC)C.P(OCC)(OCC)[O-]>>CN1C(N(C(C=2N(C=NC12)CCC)=O)CCCCCP(OCC)(OCC)=O)=O | Br[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][n:11]1[c:9](=[O:10])[c:8]2[n:4]([CH2:3][CH2:2][CH3:1])[cH:5][n:6][c:7]2[n:27]([CH3:28])[c:25]1=[O:26].[P:17]([O-:18])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][... | CCCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C.CCOP([O-])OCC | CCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#8:5]-[P;H0;D3;+0:6](-[O-;H0;D1:7])-[#8:8]-[C:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[P;H0;D4;+0:6](=[O;H0;D1;+0:7])(-[#8:5]-[C:4])-[#8:8]-[C:9] | null | [] | null | null | null | null | The title substance was prepared from 1-(5-bromopentyl)-3-methyl-7-propylxanthine and diethyl phosphite analogously to Example 16.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ncc2[nH]cnc2n1 | Br- | null | null | null | CCCn1cnc2c1c(=O)n(CCCCCBr)c(=O)n2C.CCOP([O-])OCC>>CCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6aa4458a36274254b109c6155ed0e1f1 | CCOP(=O)(CCCCCO)OCC.Cc1ccc(S(=O)(=O)Cl)cc1>>CCOP(=O)(CCCCCOS(=O)(=O)c1ccc(C)cc1)OCC | OCCCCCP(OCC)(OCC)=O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C1(=CC=C(C=C1)S(=O)(=O)OCCCCCP(OCC)(OCC)=O)C | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[O:22][CH2:23][CH3:24].Cl[S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][c:18]([CH3:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][c:18]([CH3:19])[cH:... | CCOP(=O)(CCCCCO)OCC.Cc1ccc(S(=O)(=O)Cl)cc1 | CCOP(=O)(CCCCCOS(=O)(=O)c1ccc(C)cc1)OCC | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C: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 | [] | 0 | CELSIUS | null | null | 30 g (0.134 mol) of diethyl 5-hydroxypentylphosphonate (see Example 21) were dissolved in 200 ml of pyridine, and the solution was cooled to 0° C. and treated with stirring with 26.1 g (0.134 mol) of 4-toluenesulfonyl chloride. The reaction mixture was concentrated under reduced pressure, taken up in ethyl acetate, was... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | 0 | null | CCOP(=O)(CCCCCO)OCC.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>CCOP(=O)(CCCCCOS(=O)(=O)c1ccc(C)cc1)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-37e8c73db5a4451484b91a4dd3cc9bb3 | CC(=O)OCCCCCBr.CCOP(OCC)OCC>>CCOP(=O)(CCCCCOC(C)=O)OCC | C(C)(=O)OCCCCCBr.P(OCC)(OCC)OCC>>C(C)(=O)OCCCCCP(=O)(OCC)OCC | Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:13])=[O:14].CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:15][CH2:16][CH3:17]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:13])=[O:14])[O:15][CH2:16][CH3:17] | CC(=O)OCCCCCBr.CCOP(OCC)OCC | CCOP(=O)(CCCCCOC(C)=O)OCC | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C-[O;H0;D2;+0:4]-[P;H0;D3;+0:5](-[#8:6]-[C:7])-[#8:8]-[C:9]>>[C:7]-[#8:6]-[P;H0;D4;+0:5](=[O;H0;D1;+0:4])(-[#8:8]-[C:9])-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | 100.34 g (0.48 mol) of 5-bromopentyl acetate were heated at 150° C. for 8 hours with 79.8 g (0.048 mol) of triethyl phosphite while stirring and passing in nitrogen. The mixture was then fractionally distilled under reduced pressure.
Conditions: See reaction.notes.procedure_details.
Workup: The mixture was then fractio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | null | HBr | null | null | null | CC(=O)OCCCCCBr.CCOP(OCC)OCC>>CCOP(=O)(CCCCCOC(C)=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c88ff47b784b42e596807b91fc6e4cda | CCOP(=O)(CCCCCOC(C)=O)OCC>>CCOP(=O)(CCCCCO)OCC | C(C)(=O)OCCCCCP(=O)(OCC)OCC.C([O-])([O-])=O.[Na+].[Na+]>>OCCCCCP(OCC)(OCC)=O | CC(=O)[O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:12][CH2:13][CH3:14]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[O:12][CH2:13][CH3:14] | CCOP(=O)(CCCCCOC(C)=O)OCC | CCOP(=O)(CCCCCO)OCC | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | 92 g (0.345 mol) of 5-(diethylphosphono)pentyl acetate were heated at 50° C. for 10 hours with stirring with 74 g (0.7 mol) of finely powdered sodium carbonate in 500 ml of methanol. The solution was filtered, concentrated and distilled in a bulb tube.
Conditions: See reaction.notes.procedure_details.
Workup: The solut... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | HO- | CO | null | null | CCOP(=O)(CCCCCOC(C)=O)OCC>CO>CCOP(=O)(CCCCCO)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e24e4dd0b0641159e1602ba6f4a336e | C1=COCCC1.CCOP(=O)(CCCCCO)OCC>>CCOP(=O)(CCCCCOC1CCCCO1)OCC | OCCCCCP(OCC)(OCC)=O.O1CCCC=C1.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>O1C(CCCC1)OCCCCCP(OCC)(OCC)=O | [CH2:12]1[CH2:13][CH2:14][CH:15]=[CH:16][O:17]1.[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[O:18][CH2:19][CH3:20]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17]1)[O:18][CH2:19][CH3:20] | C1=COCCC1.CCOP(=O)(CCCCCO)OCC | CCOP(=O)(CCCCCOC1CCCCO1)OCC | null | null | ClCCl | Heteroatom Alkylation and Arylation | oxa-Michael addition | abdcab389770d0a73be3b825aa1d56cee234da38dbdf3510fe8104d481e7cf3f | c6a3efa2acb508a32cdf9fcedfcd9635cce0ecdcf12c094b743aa576ea01fd9a | C1CCOCC1 | [#8:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH;D3;+0:2]1-[#8:1]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:4]-[C:3]-1 | null | [] | null | null | null | null | A solution of 66.9 g (0.298 mol) of diethyl 5-hydroxypentylphosphonate, 32.6 g (0.38 mol) of 3,4-dihydropyran and 1 g (0.004 mol) of pyridinium toluene-4-sulfonate in 800 ml of dichloromethane was heated under reflux for 16 hours. The solution was washed with water and saturated sodium hydrogen carbonate solution, drie... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | ClCCl | null | null | C1=COCCC1.CCOP(=O)(CCCCCO)OCC>ClCCl>CCOP(=O)(CCCCCOC1CCCCO1)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8696035fa4f54687939bb64a88e38937 | CCOP(=O)(CCCCCOC1CCCCO1)OCC.CI>>CCOP(=O)(OCC)C(C)CCCCOC1CCCCO1 | CI.C(CCC)[Li].[Cl-].[Na+].O1C(CCCC1)OCCCCCP(OCC)(OCC)=O>>CC(CCCCOC1OCCCC1)P(OCC)(OCC)=O | [CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:21]1.I[CH3:10]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:21]1 | CCOP(=O)(CCCCCOC1CCCCO1)OCC.CI | CCOP(=O)(OCC)C(C)CCCCOC1CCCCO1 | null | null | CCCCCC.C(C)(=O)OCC.O1CCCC1 | C-C Coupling | Methylation with MeI_secondary | 0e09d968095a587418cca2841b1e4f096e8103de8fbb60e833faf1fb3df36a41 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | C1CCOCC1 | I-[CH3;D1;+0:1].[#8:2]-[#15:3](-[#8:4])(=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7]-[C:8]>>[#8:2]-[#15:3](-[#8:4])(=[O;D1;H0:5])-[CH;D3;+0:6](-[CH3;D1;+0:1])-[C:7]-[C:8] | null | [] | -70 | CELSIUS | 30 | MINUTE | 30 g (0.097 mol) of diethyl 5-(tetrahydropyran-2-yloxy)pentylphosphonate were initially introduced into 200 ml of absolute tetrahydrofuran under an argon atmosphere, cooled to -70° C. and treated with 42.8 ml (0.107 mol) of a 2.5 molar solution of butyllithium in hexane. After addition, the solution was stirred for a f... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCOCC1 | HI | CCCCCC.C(C)(=O)OCC.O1CCCC1 | -70 | 0.5 | CCOP(=O)(CCCCCOC1CCCCO1)OCC.CI>CCCCCC.C(C)(=O)OCC.O1CCCC1>CCOP(=O)(OCC)C(C)CCCCOC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73eb847fa4744d04af4bf241c54b60cc | CCOP(=O)(OCC)C(CCCC(C)C)OC1CCCCO1>>CCOP(=O)(OCC)C(C)(C)CCCCO | CC(CCCC(OC1OCCCC1)P(OCC)(OCC)=O)C.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1.C(C)O>>OCCCCC(C)(C)P(OCC)(OCC)=O | C1CO[CH:15]([O:16][CH:9]([P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:6][CH2:7][CH3:8])[CH2:12][CH2:13]CC([CH3:10])[CH3:11])[CH2:14]C1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][CH2:14][CH2:15][OH:16] | CCOP(=O)(OCC)C(CCCC(C)C)OC1CCCCO1 | CCOP(=O)(OCC)C(C)(C)CCCCO | null | null | null | Miscellaneous | OtherReaction | 4f86bf361d11e38750ab71229b64c9b2ca91117b6792dc0e9fb511af3bc93407 | c52d856c3c221e45fd9ef8f4da14d1d74747652ebf327e93e28e9cc4d7852ba1 | null | [#8:1]-[#15:2](-[#8:3])(=[O;D1;H0:4])-[CH;D3;+0:5](-[C:6]-[CH2;D2;+0:7]-C-C(-[CH3;D1;+0:8])-[CH3;D1;+0:9])-[O;H0;D2;+0:10]-[CH;D3;+0:11]1-O-C-C-C-[CH2;D2;+0:12]-1>>[#8:1]-[#15:2](-[#8:3])(=[O;D1;H0:4])-[C;H0;D4;+0:5](-[CH3;D1;+0:8])(-[CH3;D1;+0:9])-[C:6]-[CH2;D2;+0:7]-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[OH;D1;+0:10] | null | [] | null | null | null | null | 19.9 g (0.052 mol) of diethyl 1,1-dimethyl-5-(tetrahydropyran-2-yloxy)-5-pentylphosphonate were stirred at 55° C. for 8 hours with 1.5 g (0.006 mol) of pyridinium toluene-4-sulfonate in 200 ml of aqueous ethanol. The solvent was evaporated, the residue was taken up in ethyl acetate, the solution was filtered through a ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | null | HO- | null | null | null | CCOP(=O)(OCC)C(CCCC(C)C)OC1CCCCO1>>CCOP(=O)(OCC)C(C)(C)CCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7a6debe642dd4a55a17f79ac83e9ef86 | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C.ClCCCCP(OCC)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)C | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:29][CH2:30][CH3:31].[nH:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:17]2[CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:25]([CH3:26])[c:27]1=[O:28]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11](=[O:12])[c:13]2[c... | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:1:... | null | [] | 70 | CELSIUS | null | null | 20.4 g (0.08 mol) of 7-benzyl-3-methylxanthine were suspended in 200 ml of dimethylformamide (DMF), treated with 22 g (0.96 mol) of diethyl 4-chlorobutanephosphonate and 13.8 g (0.1 mol) of activated potassium carbonate and heated at 70° C. for 4 hours and filtered, the filtrate was concentrated under reduced pressure ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | CN(C=O)C | 70 | null | CCOP(=O)(CCCCCl)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>CN(C=O)C>CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ecb037eb61a74599a6353b1d72d5a468 | CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC>>CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC | C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)C>>CN1C(N(C(C=2NC=NC12)=O)CCCCP(OCC)(OCC)=O)=O | c1ccc(C[n:14]2[c:13]3[c:11](=[O:12])[n:10]([CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:22][CH2:23][CH3:24])[c:20](=[O:21])[n:18]([CH3:19])[c:17]3[n:16][cH:15]2)cc1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11](=[O:12])[c:13]2[nH:14][cH:15][n:16][c:17]2[n:18]([CH3:19])[... | CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC | CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC | null | [Pd] | C(C)O | Deprotection | OtherReaction | 3d9a5ab3644944bc89314c4573926012058c142eafe4129eb62ce309eab26216 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C;D1;H3:5]):[c:6]2:[#7;a:7]:[c:8]:[n;H0;D3;+0:9](-C-c3:c:c:c:c:c:3):[c:10]:2:[c:11]:1=[O;D1;H0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4](-[C;D1;H3:5]):[c:6]2:[#7;a:7]:[c:8]:[nH;D2;+0:9]:[c:10]:2:[c:11]:1=[O;D1;H0:12] | null | [] | null | null | null | null | 15.7 g (0.035 mol) of diethyl [4-(7-benzyl-3-methylxanthin-1-yl)butyl]-phosphonate were hydrogenated in 150 ml of ethanol over 1 g of palladium (10%) on active carbon at room temperature in the course of 8 hours. The catalyst was filtered off, the filtrate was concentrated under reduced pressure and the residue was cry... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | [Pd].C(C)O | null | null | CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC>[Pd].C(C)O>CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed605b1432c04b18a421b64e3ecf749d | CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC>>Cn1c(=O)n(CCCCP(=O)([O-])[O-])c(=O)c2[nH]cnc21.[NH4+].[NH4+] | CN1C(N(C(C=2NC=NC12)=O)CCCCP(OCC)(OCC)=O)=O.Cl>>CN1C(N(C(C=2NC=NC12)=O)CCCCP([O-])([O-])=O)=O.[NH4+].[NH4+] | CC[O:12][P:10]([CH2:9][CH2:8][CH2:7][CH2:6][n:5]1[c:3](=[O:4])[n:2]([CH3:1])[c:20]2[c:16]([c:14]1=[O:15])[nH:17][cH:18][n:19]2)(=[O:11])[O:13]CC>>[CH3:1][n:2]1[c:3](=[O:4])[n:5]([CH2:6][CH2:7][CH2:8][CH2:9][P:10](=[O:11])([O-:12])[O-:13])[c:14](=[O:15])[c:16]2[nH:17][cH:18][n:19][c:20]12.[NH4+:21].[NH4+:22] | CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC | Cn1c(=O)n(CCCCP(=O)([O-])[O-])c(=O)c2[nH]cnc21.[NH4+].[NH4+] | null | null | null | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C>>[C:3]-[#15:2](-[O-;H0;D1:1])(-[O-;H0;D1:5])=[O;D1;H0:4] | null | [] | null | null | null | null | 5.2 g (0.0125 mol) of diethyl [4-(3-methylxanthin-1-yl)butyl]phosphonate were heated under reflux with 30 ml of 20% strength hydrochloric acid for 4 hours. The hydrochloric acid was evaporated and the oily residue was dried over potassium hydroxide in a desiccator. The phosphonic acid formed was then treated with a met... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncc2[nH]cnc2n1 | Other | null | null | null | CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC>>Cn1c(=O)n(CCCCP(=O)([O-])[O-])c(=O)c2[nH]cnc21.[NH4+].[NH4+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84fabc66583e43db913aa7d98ea5cb07 | CCOCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCCCl)OCC>>CCOCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2C | C(C)OCN1C=NC=2N(C(NC(C12)=O)=O)C.ClCCCCP(OCC)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)C | [CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:25](=[O:26])[n:27]2[CH3:28].Cl[CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:18])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15][CH2:16][P:17]... | CCOCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCCCl)OCC | CCOCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:14](=[O;D1;H0:15]):[c:16]2:[#7;a:5](-[C:4]):[c:6]:[#7;a:7]:[c:8]:2:[#7;a:9](-[C;D1;H3:10]):[c:11]:1=[O;D1;H0:12] | null | [] | 70 | CELSIUS | null | null | 44.8 g (0.2 mol) of 7-ethoxymethyl-3-methylxanthine were suspended in 500 ml of DMF, treated with 55 g (0.24 mol) of diethyl 4-chlorobutane-phosphonate and 50 g (0.32 mol) of activated potassium carbonate and heated at 70° C. for 4 hours and filtered, the filtrate was concentrated under reduced pressure and the oily re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | CN(C)C=O | 70 | null | CCOCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCCCl)OCC>CN(C)C=O>CCOCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed0a8010fe1240b0b02babed64992c40 | CCOCn1cnc2c1c(=O)n(CCCCP(=O)([O-])OCCCc1ccccc1)c(=O)n2C.N>>CCOCn1cnc2c1c(=O)n(CCCCP(=O)([O-])[O-])c(=O)n2C.CC[NH3+].CC[NH3+] | C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCCP(OCCCC1=CC=CC=C1)([O-])=O)=O)C.N>>C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCCP([O-])([O-])=O)=O)C.C(C)[NH3+].C(C)[NH3+] | c1cc(C[CH2:28][CH2:29][O:20][P:17]([CH2:16][CH2:15][CH2:14][CH2:13][n:12]2[c:10](=[O:11])[c:9]3[n:5]([CH2:4][O:3][CH2:2][CH3:1])[cH:6][n:7][c:8]3[n:23]([CH3:24])[c:21]2=[O:22])(=[O:18])[O-:19])[cH:26][cH:25]c1.[NH3:27]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15... | CCOCn1cnc2c1c(=O)n(CCCCP(=O)([O-])OCCCc1ccccc1)c(=O)n2C.N | CCOCn1cnc2c1c(=O)n(CCCCP(=O)([O-])[O-])c(=O)n2C.CC[NH3+].CC[NH3+] | null | [Pd] | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f8f4dc1019caf79ed30f437fbd2db0fb6825cb61837ce309160d223c1aa621f4 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | [C:1]-[#15:2](-[O;-;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-C-c1:[cH;D2;+0:8]:[cH;D2;+0:9]:c:c:c:1.[NH3;D0;+0:10]>>[CH3;D1;+0:7]-[CH2;D2;+0:6]-[N;+;D1;H3:11].[CH3;D1;+0:9]-[CH2;D2;+0:8]-[NH3+;D1:10].[C:1]-[#15:2](-[O-;H0;D1:5])(-[O;-;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | 6.3 g (0.013 mol) of benzylethyl 4-(7-ethoxymethyl-3-methylxanthin-1-yl)-butylphosphonate were hydrogenated in 100 ml of ethanol over 0.5 g of palladium (10%) on active carbon at room temperature in the course of 4 hours. The catalyst was filtered off, the filtrate was concentrated under reduced pressure, the solution ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ncc2[nH]cnc2n1 | Other | [Pd].C(C)O | null | null | CCOCn1cnc2c1c(=O)n(CCCCP(=O)([O-])OCCCc1ccccc1)c(=O)n2C.N>[Pd].C(C)O>CCOCn1cnc2c1c(=O)n(CCCCP(=O)([O-])[O-])c(=O)n2C.CC[NH3+].CC[NH3+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8959e916559b4ac888f77a67d88387d1 | N>>[NH4+].[NH4+] | N.C[Si](C)(C)Br.C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCCP([O-])([O-])=O)=O)C.CO>>C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCCP([O-])([O-])=O)=O)C.[NH4+].[NH4+] | [NH3:25]>>[NH4+:25].[NH4+:26] | N | [NH4+].[NH4+] | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | [NH3;D0;+0:1]>>[NH4+;D0:1] | null | [] | 0 | CELSIUS | 2 | HOUR | 3.4 ml (0.026 mol) of trimethylsilyl bromide were slowly added dropwise at 0° C., under an argon atmosphere, to a solution of 4.16 g (0.01 mol) of [4-(7-ethoxymethyl-3-methylxanthin-1-yl)butyl]phosphonate in 5 ml of dichloromethane. The solution was stirred at 0° C. for 1 hour and at room temperature for 2 hours. The d... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | ClCCl | 0 | 2 | N>ClCCl>[NH4+].[NH4+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf99dda85e8446dfbb7ca469f46d02aa | CCOP(=O)(CCCCCl)OCC.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2C)n(C)c1=O)OCC | N1C(=O)N(C)C=2N=CN(C)C2C1=O.ClCCCCP(OCC)(=O)OCC>>CN1C(N(C(C=2N(C=NC12)C)=O)CCCCP(OCC)(OCC)=O)=O | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:23][CH2:24][CH3:25].[nH:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:17]2[CH3:18])[n:19]([CH3:20])[c:21]1=[O:22]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:17]2[CH3:18])[n:19]([C... | CCOP(=O)(CCCCCl)OCC.Cn1cnc2c1c(=O)[nH]c(=O)n2C | CCOP(=O)(CCCCn1c(=O)c2c(ncn2C)n(C)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:14](=[O;D1;H0:15]):[c:16]2:[#7;a:5](-[C;D1;H3:4]):[c:6]:[#7;a:7]:[c:8]:2:[#7;a:9](-[C;D1;H3:10]):[c:11]:1=[... | null | [] | null | null | null | null | The title substance was prepared from 0.075 mol of theobromine and 0.09 mol of diethyl 4-chlorobutanephosphonate analogously to Example 23 and crystallized from diisopropyl ether.
Conditions: See reaction.notes.procedure_details.
Workup: crystallized from diisopropyl ether | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | null | null | null | CCOP(=O)(CCCCCl)OCC.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2C)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-056956b73b9f45e9955998f708e34b9b | CCI.CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC | CN1C(N(C(C=2NC=NC12)=O)CCCCP(OCC)(OCC)=O)=O.C(C)I.C([O-])([O-])=O.[K+].[K+]>>C(C)N1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)C | I[CH2:18][CH3:19].[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][nH:17]2)[n:20]([CH3:21])[c:22]1=[O:23])[O:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:17]2[CH2:18][CH... | CCI.CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC | CCOP(=O)(CCCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[#7;a:4]1:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8]2:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:2:[c:13]:1=[O;D1;H0:14]>>[C:3]-[#7;a:4]1:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8]2:[#7;a:9]:[c:10]:[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:12]:2:[c:13]:1=[O;D1;H0:14] | null | [] | 60 | CELSIUS | null | null | 7.2 g (0.02 mol) of diethyl [4-(3-methylxanthin-1-yl)-butyl]phosphonate were suspended in 100 ml of DMF, treated with 4.7 g (0.03 mol) of ethyl iodide and 4.1 g (0.03 mol) of activated potassium carbonate and heated at 60° C. for 4 hours. The solid was filtered off, the filtrate was concentrated under reduced pressure ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HI | CN(C)C=O | 60 | null | CCI.CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC>CN(C)C=O>CCOP(=O)(CCCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ccbe3ff71f04729a89ed7db3a53f3b8 | CCOP(=O)(CCCCCl)OCC.COCCn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2CCOC)n(C)c1=O)OCC | COCCN1C=NC=2N(C(NC(C12)=O)=O)C.ClCCCCP(OCC)(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>COCCN1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)C | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:26][CH2:27][CH3:28].[nH:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:17]2[CH2:18][CH2:19][O:20][CH3:21])[n:22]([CH3:23])[c:24]1=[O:25]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:... | CCOP(=O)(CCCCCl)OCC.COCCn1cnc2c1c(=O)[nH]c(=O)n2C | CCOP(=O)(CCCCn1c(=O)c2c(ncn2CCOC)n(C)c1=O)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:1:... | null | [] | 70 | CELSIUS | null | null | 9 g (0.04 mol) of 7-methoxyethyl-3-methylxanthine were suspended in 100 ml of DMF, treated with 11 g (0.048 mol) of diethyl 4-chlorobutane-phosphonate and 10 g (0.064 mol) of activated potassium carbonate and heated at 70° C. for 4 hours. The solid was filtered off, the filtrate was concentrated under reduced pressure ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | CN(C)C=O | 70 | null | CCOP(=O)(CCCCCl)OCC.COCCn1cnc2c1c(=O)[nH]c(=O)n2C>CN(C)C=O>CCOP(=O)(CCCCn1c(=O)c2c(ncn2CCOC)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-82da64e54168413bb57aba668109b96d | CCCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCCCl)OCC>>CCCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2C | CN1C(NC(C=2N(C=NC12)CCC)=O)=O.ClCCCCP(OCC)(=O)OCC>>CN1C(N(C(C=2N(C=NC12)CCC)=O)CCCCP(OCC)(OCC)=O)=O | [CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[nH:11][c:24](=[O:25])[n:26]2[CH3:27].Cl[CH2:12][CH2:13][CH2:14][CH2:15][P:16](=[O:17])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][P:16](=[O:17])([O... | CCCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCCCl)OCC | CCCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:11](=[O;D1;H0:12]):[#7;a:9](-[C;D1;H3:10]):[c:8]2:[#7;a:7]:[c:6]:[#7;a:5](-[C:4]):[c:16]:2:[c:14]:1=[O;D1;H0:15] | null | [] | null | null | null | null | The title substance was prepared from 0.072 mol of 3-methyl-7-propyl-xanthine and 0.072 mol of diethyl 4-chlorobutanephosphonate analogously to Example 23, chromatographed on silica gel (eluent: dichloromethane/methanol 20:1) and crystallized from diisopropyl ether.
Conditions: See reaction.notes.procedure_details.
Wor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CCCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCCCl)OCC>>CCCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-38aa921c2f824a8a8df4283d74a543c9 | CCOP(=O)(CCCBr)OCC.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOP(=O)(CCCn1c(=O)c2c(ncn2C)n(C)c1=O)OCC | N1C(=O)N(C)C=2N=CN(C)C2C1=O.BrCCCP(OCC)(=O)OCC>>CN1C(N(C(C=2N(C=NC12)C)=O)CCCP(OCC)(OCC)=O)=O | Br[CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:22][CH2:23][CH3:24].[nH:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:16]2[CH3:17])[n:18]([CH3:19])[c:20]1=[O:21]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:16]2[CH3:17])[n:18]([CH3:19])[c:20]1=[... | CCOP(=O)(CCCBr)OCC.Cn1cnc2c1c(=O)[nH]c(=O)n2C | CCOP(=O)(CCCn1c(=O)c2c(ncn2C)n(C)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:14](=[O;D1;H0:15]):[c:16]2:[#7;a:5](-[C;D1;H3:4]):[c:6]:[#7;a:7]:[c:8]:2:[#7;a:9](-[C;D1;H3:10]):[c:11]:1=[... | null | [] | null | null | null | null | The title substance was prepared from 0.067 mol of theobromine and 0.08 mol of diethyl 3-bromopropanephosphonate analogously to Example 32.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HBr | null | null | null | CCOP(=O)(CCCBr)OCC.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOP(=O)(CCCn1c(=O)c2c(ncn2C)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b873039c08354be38bd2be8966ce1a89 | CCOP(=O)(CCCBr)OCC.CCn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOP(=O)(CCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC | C(C)N1C=NC=2N(C(NC(C12)=O)=O)C.BrCCCP(OCC)(=O)OCC>>C(C)N1C=NC=2N(C(N(C(C12)=O)CCCP(OCC)(OCC)=O)=O)C | Br[CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:23][CH2:24][CH3:25].[nH:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:16]2[CH2:17][CH3:18])[n:19]([CH3:20])[c:21]1=[O:22]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:16]2[CH2:17][CH3:18])[n:19]([C... | CCOP(=O)(CCCBr)OCC.CCn1cnc2c1c(=O)[nH]c(=O)n2C | CCOP(=O)(CCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:1:... | null | [] | null | null | null | null | The title substance was prepared from 0.041 mol of 7-ethyl-3-methyl-xanthine and 0.049 mol of diethyl 3-bromopropanephosphonate analogously to Example 32.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HBr | null | null | null | CCOP(=O)(CCCBr)OCC.CCn1cnc2c1c(=O)[nH]c(=O)n2C>>CCOP(=O)(CCCn1c(=O)c2c(ncn2CC)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-26849af8cbc844578b2946656b10208a | CCOCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCBr)OCC>>CCOCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2C | C(C)OCN1C=NC=2N(C(NC(C12)=O)=O)C.BrCCCP(OCC)(=O)OCC>>C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCP(OCC)(OCC)=O)=O)C | [CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:24](=[O:25])[n:26]2[CH3:27].Br[CH2:13][CH2:14][CH2:15][P:16](=[O:17])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15][P:16](=[O:17])([O:18]... | CCOCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCBr)OCC | CCOCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:14](=[O;D1;H0:15]):[c:16]2:[#7;a:5](-[C:4]):[c:6]:[#7;a:7]:[c:8]:2:[#7;a:9](-[C;D1;H3:10]):[c:11]:1=[O;D1;H0:12] | null | [] | null | null | null | null | The title substance was prepared from 0.048 mol of 7-ethoxymethyl-3-methylxanthine and 0.058 mol of diethyl 3-bromopropanephosphonate analogously to Example 32 and chromatographed on silica gel (eluent: ethyl acetate/methanol 10:1).
Conditions: See reaction.notes.procedure_details.
Workup: chromatographed on silica gel... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | null | null | null | CCOCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCBr)OCC>>CCOCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61cce6857443438ba8ad80c482010310 | BrCc1ccccc1.CCn1c(=O)[nH]c(=O)c2[nH]cnc21>>CCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | C(C)N1C(NC(C=2NC=NC12)=O)=O.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)CC | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[nH:6][c:7](=[O:8])[c:9]2[c:10]1[n:11][cH:12][nH:13]2>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[nH:6][c:7](=[O:8])[c:9]2[c:10]1[n:11][cH:12][n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | BrCc1ccccc1.CCn1c(=O)[nH]c(=O)c2[nH]cnc21 | CCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[c:15]:1:[#7;a:14]:[c:13]:[n;H0;D3;+0:12]:2-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 18 g (0.1 mol) of 3-ethylxanthine were stirred at 60° C. for 2 hours with 19.2 g (0.11 mol) of benzyl bromide and 15.2 g (0.11 mol) of potassium carbonate. The reaction solution was transferred to an Edenmeyer flask and treated with 1000 ml of water. The precipitate was filtered off with suction, washed several times w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | O | null | null | BrCc1ccccc1.CCn1c(=O)[nH]c(=O)c2[nH]cnc21>O>CCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f4e76ea00e564ed586febf57d57779fb | CCOP(=O)(CCCCCl)OCC.CCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(CC)c1=O)OCC | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)CC.ClCCCCP(OCC)(=O)OCC>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)CC | Cl[CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:30][CH2:31][CH3:32].[nH:10]1[c:11](=[O:12])[c:13]2[c:14]([n:15][cH:16][n:17]2[CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:25]([CH2:26][CH3:27])[c:28]1=[O:29]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[c:11](=[O:12])[... | CCOP(=O)(CCCCCl)OCC.CCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(CC)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:1:2 | null | [] | null | null | null | null | The title substance was prepared from 0.04 mol of 7-benzyl-3-ethyl-xanthine and 0.048 mol of diethyl 4-chlorobutanephosphonate analogously to Example 23.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | null | null | null | CCOP(=O)(CCCCCl)OCC.CCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOP(=O)(CCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(CC)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f7760bc41454f178cfc2b916e1815a1 | CCCBr.CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(CC)c1=O)OCC>>CCCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2CC | C(C)N1C(N(C(C=2NC=NC12)=O)CCCCP(OCC)(OCC)=O)=O.BrCCC>>C(C)N1C(N(C(C=2N(C=NC12)CCC)=O)CCCCP(OCC)(OCC)=O)=O | Br[CH2:3][CH2:2][CH3:1].[nH:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][P:16](=[O:17])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23])[c:24](=[O:25])[n:26]2[CH2:27][CH3:28]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][P:16](=... | CCCBr.CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(CC)c1=O)OCC | CCCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2CC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C:8]):[c:9]2:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:[c:14]:1=[O;D1;H0:15]>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C:8]):[c:9]2:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3]):[c:13]:2:[c:14]:1=[O;D1;H0:15] | null | [] | null | null | null | null | The title substance was prepared from 8.2 mmol of diethyl [4-(3-ethyl-xanthin-1-yl)butyl]phosphonate and 9.8 mmol of bromopropane analogously to Example 30 and chromatographed on silica gel (eluent: dichloromethane/methanol 20:1).
Conditions: See reaction.notes.procedure_details.
Workup: chromatographed on silica gel (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | null | null | null | CCCBr.CCOP(=O)(CCCCn1c(=O)c2[nH]cnc2n(CC)c1=O)OCC>>CCCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8e167d88150f459d95e6145c9ec1c182 | CCCBr.O=c1[nH]c(=O)n(C2CC2)c2nc[nH]c12>>CCCn1cnc2c1c(=O)[nH]c(=O)n2C1CC1 | BrCCC.C1(CC1)N1C(NC(C=2NC=NC12)=O)=O.[H-].[Na+].[H][H]>>C1(CC1)N1C(NC(C=2N(C=NC12)CCC)=O)=O | Br[CH2:3][CH2:2][CH3:1].[nH:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[nH:11][c:12](=[O:13])[n:14]2[CH:15]1[CH2:16][CH2:17]1>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[nH:11][c:12](=[O:13])[n:14]2[CH:15]1[CH2:16][CH2:17]1 | CCCBr.O=c1[nH]c(=O)n(C2CC2)c2nc[nH]c12 | CCCn1cnc2c1c(=O)[nH]c(=O)n2C1CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)n(C2CC2)c2nc[nH]c12 | Br-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[nH;D2;+0:11]:[c:12]:[#7;a:13]:[c:14]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[c:14]:1:[#7;a:13]:[c:12]:[n;H0;D3;+0:11]:2-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3] | null | [] | 60 | CELSIUS | 3 | HOUR | 9.6 g (0.05 mol) of 3-cyclopropylxanthine were suspended in 150 ml of dimethylformamide and slowly deprotonated using 1.45 g (0.06 mol) of sodium hydride. When evolution of hydrogen was at an end, the solution was heated to 60° C. and treated dropwise with 6.77 g (0.055 mol) of bromopropane. After stirring at 70° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CC1 | HBr | CN(C=O)C | 60 | 3 | CCCBr.O=c1[nH]c(=O)n(C2CC2)c2nc[nH]c12>CN(C=O)C>CCCn1cnc2c1c(=O)[nH]c(=O)n2C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-850bc9b85c9e4146b22bb952817275a6 | CCCCn1cnc2c1c(=O)[nH]c(=O)n2CCCC.CCOP(=O)(CCCBr)OCC>>CCCCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2CCCC | C(CCC)N1C(NC(C=2N(C=NC12)CCCC)=O)=O.BrCCCP(OCC)(=O)OCC>>C(CCC)N1C(N(C(C=2N(C=NC12)CCCC)=O)CCCP(OCC)(OCC)=O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:24](=[O:25])[n:26]2[CH2:27][CH2:28][CH2:29][CH3:30].Br[CH2:13][CH2:14][CH2:15][P:16](=[O:17])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][C... | CCCCn1cnc2c1c(=O)[nH]c(=O)n2CCCC.CCOP(=O)(CCCBr)OCC | CCCCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2CCCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6](=[O;D1;H0:7]):[nH;D2;+0:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[#7;a:12](-[C:13]):[c:14]:[#7;a:15]:[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:9](=[O;D1;H0:10]):[c:11]2:[#7;a:12](-[C:13]):[c:14]:[#7;a:15]:[c:16]:2:[#7;a:5](-[C:4]):[c:6]:1=[O;D1;H0:7] | null | [] | null | null | null | null | The title substance was prepared from 0.02 mol of 3,7-dibutylxanthine and 0.022 mol of diethyl 3-bromopropanephosphonate analogously to Example 23 and chromatographed on silica gel (eluent: dichloromethane/methanol 20:1).
Conditions: See reaction.notes.procedure_details.
Workup: chromatographed on silica gel (eluent: d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | null | null | null | CCCCn1cnc2c1c(=O)[nH]c(=O)n2CCCC.CCOP(=O)(CCCBr)OCC>>CCCCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2CCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-53dbbec3515e46f1bf52497ce7ab8115 | CC(C)CCBr.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>CC(C)CCn1cnc2c1c(=O)[nH]c(=O)n2C | BrCCC(C)C.[H-].[Na+].CN1C(NC(C=2NC=NC12)=O)=O.[H][H]>>CC(CCN1C=NC=2N(C(NC(C12)=O)=O)C)C | Br[CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3].[nH:6]1[cH:7][n:8][c:9]2[c:10]1[c:11](=[O:12])[nH:13][c:14](=[O:15])[n:16]2[CH3:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[c:11](=[O:12])[nH:13][c:14](=[O:15])[n:16]2[CH3:17] | CC(C)CCBr.Cn1c(=O)[nH]c(=O)c2[nH]cnc21 | CC(C)CCn1cnc2c1c(=O)[nH]c(=O)n2C | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[nH;D2;+0:11]:[c:12]:[#7;a:13]:[c:14]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:12]:[#7;a:13]:[c:14]2:[#7;a:5](-[C;D1;H3:4]):[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]:2:1 | null | [] | 60 | CELSIUS | 12 | HOUR | 100 g (0.602 mol) of 3-methylxanthine, dissolved in 1200 ml of DMF, were slowly treated with 16 g (0.66 mol) of sodium hydride. The solution was heated to 60° C. and, when the evolution of hydrogen was at an end, treated with 109 g (0.66 mol) of 1-bromo-3-methylbutane. The reaction mixture was stirred at 100° C. for 12... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | CN(C)C=O.O | 60 | 12 | CC(C)CCBr.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>CN(C)C=O.O>CC(C)CCn1cnc2c1c(=O)[nH]c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8db1122947c440319b376bdd83c6820e | CCOP(=O)(CCCBr)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOP(=O)(CCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C.BrCCCP(OCC)(=O)OCC>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)CCCP(OCC)(OCC)=O)=O)C | Br[CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:28][CH2:29][CH3:30].[nH:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:16]2[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]([CH3:25])[c:26]1=[O:27]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:1... | CCOP(=O)(CCCBr)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | CCOP(=O)(CCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:1:... | null | [] | null | null | null | null | The title substance was prepared from 7-benzyl-3-methylxanthine, (0.04 mol) and diethyl 3-bromopropanphosphonate (0.046 mol) analogously to Example 23.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | null | null | null | CCOP(=O)(CCCBr)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOP(=O)(CCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dbd5f59d9f5c45dc83584e93fb652d29 | CCOP(=O)(CCCCCBr)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOP(=O)(CCCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C.BrCCCCCP(OCC)(=O)OCC>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)CCCCCP(OCC)(OCC)=O)=O)C | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:30][CH2:31][CH3:32].[nH:11]1[c:12](=[O:13])[c:14]2[c:15]([n:16][cH:17][n:18]2[CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[n:26]([CH3:27])[c:28]1=[O:29]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n:11]1[c:12](=... | CCOP(=O)(CCCCCBr)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | CCOP(=O)(CCCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2Cc2ccccc2)[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:14](=[O;D1;H0:15]):[c:16]:1:... | null | [] | null | null | null | null | The title compound was prepared from 7-benzyl-3-methylxanthine (0.059 mol) and diethyl 5-bromopentanephosphonate (0.07 mol) analogously to Example 23.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | null | null | null | CCOP(=O)(CCCCCBr)OCC.Cn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CCOP(=O)(CCCCCn1c(=O)c2c(ncn2Cc2ccccc2)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-465ca427a226420c828105b026a9c1d8 | CCOP(=O)(CCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC.ClCC1CC1>>CCOP(=O)(CCCn1c(=O)c2c(ncn2CC2CC2)n(C)c1=O)OCC | CN1C(N(C(C=2NC=NC12)=O)CCCP(OCC)(OCC)=O)=O.ClCC1CC1>>C1(CC1)CN1C=NC=2N(C(N(C(C12)=O)CCCP(OCC)(OCC)=O)=O)C | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][nH:16]2)[n:21]([CH3:22])[c:23]1=[O:24])[O:25][CH2:26][CH3:27].Cl[CH2:17][CH:18]1[CH2:19][CH2:20]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][n:9]1[c:10](=[O:11])[c:12]2[c:13]([n:14][cH:15][n:16]2[CH2:17][... | CCOP(=O)(CCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC.ClCC1CC1 | CCOP(=O)(CCCn1c(=O)c2c(ncn2CC2CC2)n(C)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2CC2CC2)[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]2:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c:14]:2:[c:15]:1=[O;D1;H0:16]>>[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]2:[#7;a:11]:[c:12]:[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]3-[C:3]-[C:4]-3):[c:14]:2:[c:15]:1=[O;D1;H0:16] | null | [] | null | null | null | null | The title substance was prepared from 0.015 mol of diethyl [3-(3-methyl-xanthin-1-yl)propyl]phosphonate (Example 42), and 0.017 mol of chloromethylcyclopropane analogously to Example 30 and chromatographed on silica gel (eluent: dichloromethane/methanol 20:1).
Conditions: See reaction.notes.procedure_details.
Workup: c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1CC1 | HCl | null | null | null | CCOP(=O)(CCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC.ClCC1CC1>>CCOP(=O)(CCCn1c(=O)c2c(ncn2CC2CC2)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e9220e2450c24e59bc6ac895e81aca07 | CCCCBr.CCOP(=O)(CCCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC>>CCCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C | CN1C(N(C(C=2NC=NC12)=O)CCCCCP(OCC)(OCC)=O)=O.BrCCCC>>C(CCC)N1C=NC=2N(C(N(C(C12)=O)CCCCCP(OCC)(OCC)=O)=O)C | Br[CH2:4][CH2:3][CH2:2][CH3:1].[nH:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][P:18](=[O:19])([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])[c:26](=[O:27])[n:28]2[CH3:29]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15]... | CCCCBr.CCOP(=O)(CCCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC | CCCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:[c:14]:1=[O;D1;H0:15]>>[C:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]2:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:13]:2:[c:14]:1=[O;D1;H0:15] | null | [] | null | null | null | null | The title substance was prepared from 0.008 mol of diethyl [5-(3-methyl-xanthin-1-yl)pentyl]phosphonate and 0.01 mol of 1-bromobutane analogously to Example 46.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | null | null | null | CCCCBr.CCOP(=O)(CCCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC>>CCCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c4f2236d92e42d3ad896c3d86de7aab | CCOP(=O)(CCCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC.ClCC1CC1>>CCOP(=O)(CCCCCn1c(=O)c2c(ncn2CC2CC2)n(C)c1=O)OCC | CN1C(N(C(C=2NC=NC12)=O)CCCCCP(OCC)(OCC)=O)=O.ClCC1CC1>>C1(CC1)CN1C=NC=2N(C(N(C(C12)=O)CCCCCP(OCC)(OCC)=O)=O)C | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n:11]1[c:12](=[O:13])[c:14]2[c:15]([n:16][cH:17][nH:18]2)[n:23]([CH3:24])[c:25]1=[O:26])[O:27][CH2:28][CH3:29].Cl[CH2:19][CH:20]1[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][n:11]1[c:12](=[O:13])[c:14]2[c:1... | CCOP(=O)(CCCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC.ClCC1CC1 | CCOP(=O)(CCCCCn1c(=O)c2c(ncn2CC2CC2)n(C)c1=O)OCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2c(ncn2CC2CC2)[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]2:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c:14]:2:[c:15]:1=[O;D1;H0:16]>>[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]2:[#7;a:11]:[c:12]:[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]3-[C:3]-[C:4]-3):[c:14]:2:[c:15]:1=[O;D1;H0:16] | null | [] | null | null | null | null | The title substance was prepared from 0.011 mol of diethyl [5-(3-methyl-xanthin-1-yl)pentyl]phosphonate and 0.013 mol of chloromethylcyclo-propane analogously to Example 46.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1CC1 | HCl | null | null | null | CCOP(=O)(CCCCCn1c(=O)c2[nH]cnc2n(C)c1=O)OCC.ClCC1CC1>>CCOP(=O)(CCCCCn1c(=O)c2c(ncn2CC2CC2)n(C)c1=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-97646f4f01d04c408248a374735fff7f | CCOCn1cnc2c1c(=O)[nH]c(=O)n2CC.CCOP(=O)(CCCCCl)OCC>>CCOCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2CC | C(C)OCN1C=NC=2N(C(NC(C12)=O)=O)CC.ClCCCCP(OCC)(=O)OCC>>C(C)OCN1C=NC=2N(C(N(C(C12)=O)CCCCP(OCC)(OCC)=O)=O)CC | [CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:25](=[O:26])[n:27]2[CH2:28][CH3:29].Cl[CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:18])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][O:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][CH2:14][CH2:15][CH2:1... | CCOCn1cnc2c1c(=O)[nH]c(=O)n2CC.CCOP(=O)(CCCCCl)OCC | CCOCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2CC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6](=[O;D1;H0:7]):[nH;D2;+0:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[#7;a:12](-[C:13]):[c:14]:[#7;a:15]:[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:9](=[O;D1;H0:10]):[c:11]2:[#7;a:12](-[C:13]):[c:14]:[#7;a:15]:[c:16]:2:[#7;a:5](-[C:4]):[c:6]:1=[O;D1;H0:7] | null | [] | null | null | null | null | The title substance was prepared from 0.01 5 mol of 7-ethoxymethyl-3-ethylxanthine and 0.017 mol of diethyl 4-chlorobutanephosphonate analogously to 53.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CCOCn1cnc2c1c(=O)[nH]c(=O)n2CC.CCOP(=O)(CCCCCl)OCC>>CCOCn1cnc2c1c(=O)n(CCCCP(=O)(OCC)OCC)c(=O)n2CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7aefd98413d44b3fac3a2bd4ea211f8d | CCCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCBr)OCC>>CCCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2C | CN1C(NC(C=2N(C=NC12)CCC)=O)=O.BrCCCP(OCC)(=O)OCC>>CN1C(N(C(C=2N(C=NC12)CCC)=O)CCCP(OCC)(OCC)=O)=O | [CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[nH:11][c:23](=[O:24])[n:25]2[CH3:26].Br[CH2:12][CH2:13][CH2:14][P:15](=[O:16])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][P:15](=[O:16])([O:17][CH2:18][CH3... | CCCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCBr)OCC | CCCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:11](=[O;D1;H0:12]):[#7;a:9](-[C;D1;H3:10]):[c:8]2:[#7;a:7]:[c:6]:[#7;a:5](-[C:4]):[c:16]:2:[c:14]:1=[O;D1;H0:15] | null | [] | null | null | null | null | The title substance was prepared from 0.048 mol of 3-methyl-7-propyl-xanthine and 0.058 mol of diethyl 3-bromopropanephosphonate analogously to Example 23.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | null | null | null | CCCn1cnc2c1c(=O)[nH]c(=O)n2C.CCOP(=O)(CCCBr)OCC>>CCCn1cnc2c1c(=O)n(CCCP(=O)(OCC)OCC)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b448fa8f2cf14a97b043ce62959c7c5a | CCCn1cnc2c1c(=O)[nH]c(=O)n2CC.CCOP(=O)(CCCCCBr)OCC>>CCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2CC | C(C)N1C(NC(C=2N(C=NC12)CCC)=O)=O.BrCCCCCP(OCC)(=O)OCC>>C(C)N1C(N(C(C=2N(C=NC12)CCC)=O)CCCCCP(OCC)(OCC)=O)=O | [CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[nH:11][c:25](=[O:26])[n:27]2[CH2:28][CH3:29].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:18])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[c:9](=[O:10])[n:11]([CH2:12][CH2:13][CH2:14][CH2:15][C... | CCCn1cnc2c1c(=O)[nH]c(=O)n2CC.CCOP(=O)(CCCCCBr)OCC | CCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2CC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#7;a:5]1:[c:6](=[O;D1;H0:7]):[nH;D2;+0:8]:[c:9](=[O;D1;H0:10]):[c:11]2:[#7;a:12](-[C:13]):[c:14]:[#7;a:15]:[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:6](=[O;D1;H0:7]):[#7;a:5](-[C:4]):[c:16]2:[#7;a:15]:[c:14]:[#7;a:12](-[C:13]):[c:11]:2:[c:9]:1=[O;D1;H0:10] | null | [] | null | null | null | null | The title substance was prepared from 0.0225 mol of 3-ethyl-7-propyl-xanthine and 0.027 mol of diethyl 5-bromopentanephosphonate analogously to Example 46.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HBr | null | null | null | CCCn1cnc2c1c(=O)[nH]c(=O)n2CC.CCOP(=O)(CCCCCBr)OCC>>CCCn1cnc2c1c(=O)n(CCCCCP(=O)(OCC)OCC)c(=O)n2CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3604df54e33345c3b923bde3a99dbbb6 | CP(C)(=O)CCl.Cn1c(=O)c2[nH]cnc2n(C)c1=O>>Cn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | [Na].N1(C)C(=O)N(C)C=2N=CNC2C1=O.ClCP(C)(C)=O.CN(C)C=O>>CN1C(N(C(C=2N(C=NC12)C)=O)CP(C)(C)=O)=O | Cl[CH2:10][P:11]([CH3:12])([CH3:13])=[O:14].[CH3:1][n:9]1[c:7](=[O:8])[c:6]2[nH:2][cH:3][n:4][c:5]2[n:17]([CH3:18])[c:15]1=[O:16]>>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7](=[O:8])[n:9]([CH2:10][P:11]([CH3:12])([CH3:13])=[O:14])[c:15](=[O:16])[n:17]2[CH3:18] | CP(C)(=O)CCl.Cn1c(=O)c2[nH]cnc2n(C)c1=O | Cn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C;D1;H3:6]-[#7;a:7]1:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10](-[CH3;D1;+0:11]):[c:12](=[O;D1;H0:13]):[c:14]2:[nH;D2;+0:15]:[c:16]:[#7;a:17]:[c:18]:1:2>>[C;D1;H3:3]-[#15:2](-[C;D1;H3:4])(=[O;D1;H0:5])-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:8](=[O;D1;H0:9]):[#7;a:7]... | null | [] | null | null | null | null | A solution of 20.2 g (0.1 mol) of theophylline sodium salt in 400 ml of DMF was heated at 130° C. for 3 hours with 12.7 g of chloromethyldimethyl-phosphine oxide. The solution was filtered, the solvent was evaporated and the residue was taken up in methanol. The precipitate was filtered off and dried to constant weight... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CP(C)(=O)CCl.Cn1c(=O)c2[nH]cnc2n(C)c1=O>>Cn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c44c4a79058347d5a7012c9e47dfad0e | CP(C)(=O)CCl.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>Cn1c(=O)n(CP(C)(C)=O)c(=O)c2c1ncn2P(C)(C)=O | [Na].[Na].CN1C(NC(C=2NC=NC12)=O)=O.ClCP(C)(C)=O>>CP(=O)(N1C=NC=2N(C(N(C(C12)=O)CP(C)(C)=O)=O)C)C | Cl[CH2:6][P:7]([CH3:8])([CH3:9])=[O:10].[CH3:1][n:2]1[c:3](=[O:4])[nH:5][c:11](=[O:12])[c:13]2[c:14]1[n:15][cH:16][nH:17]2>>[CH3:1][n:2]1[c:3](=[O:4])[n:5]([CH2:6][P:7]([CH3:8])([CH3:9])=[O:10])[c:11](=[O:12])[c:13]2[c:14]1[n:15][cH:16][n:17]2[P:18]([CH3:19])([CH3:20])=[O:21] | CP(C)(=O)CCl.Cn1c(=O)[nH]c(=O)c2[nH]cnc21 | Cn1c(=O)n(CP(C)(C)=O)c(=O)c2c1ncn2P(C)(C)=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C;D1;H3:6]-[#7;a:7]1:[c:8]2:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16]:1=[O;D1;H0:17]>>[C;D1;H3:18]-[#15:19](-[C;D1;H3:20])(=[O;D1;H0:21])-[n;H0;D3;+0:11]1:[c:10]:[#7;a:9]:[c:8]2:[#7;a:7](-[C;D1;H3:6]):[c:16](=[O;D1... | null | [] | null | null | null | null | The title substance was prepared from 22 g (0.1 mol) of 3-methylxanthine disodium salt and chloromethyldimethylphosphine oxide analogously to Example 59 and crystallized from methanol.
Conditions: See reaction.notes.procedure_details.
Workup: crystallized from methanol | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | null | null | null | null | CP(C)(=O)CCl.Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>Cn1c(=O)n(CP(C)(C)=O)c(=O)c2c1ncn2P(C)(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ef1db8c6e55e47b682289c4e57d4ed22 | CCCCCCn1c(=O)c2[nH]cnc2n(C)c1=O.CP(C)(=O)CCl>>CCCCCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(C)c1=O | [Na].C(CCCCC)N1C(=O)N(C=2N=CNC2C1=O)C.ClCP(C)(C)=O>>C(CCCCC)N1C(=O)N(C=2N=CN(C2C1=O)CP(C)(C)=O)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][n:7]1[c:8](=[O:9])[c:10]2[c:11]([n:12][cH:13][nH:14]2)[n:20]([CH3:21])[c:22]1=[O:23].Cl[CH2:15][P:16]([CH3:17])([CH3:18])=[O:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][n:7]1[c:8](=[O:9])[c:10]2[c:11]([n:12][cH:13][n:14]2[CH2:15][P:16]([CH3:17])([CH3:18])=[O:19])[n:20]([CH... | CCCCCCn1c(=O)c2[nH]cnc2n(C)c1=O.CP(C)(=O)CCl | CCCCCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]2:[#7;a:12]:[c:13]:[nH;D2;+0:14]:[c:15]:2:[c:16]:1=[O;D1;H0:17]>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C;D1;H3:10]):[c:11]2:[#7;a:12]:[c:13]:[n;H0;D3;+0:14](-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=... | null | [] | null | null | null | null | The title substance was prepared from 26 g (0.1 mol) of 1-hexyl-3-methylxanthine sodium salt and chloromethyldimethylphosphine oxide analogously to Example 59 and crystallized from hexane.
Conditions: See reaction.notes.procedure_details.
Workup: crystallized from hexane | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | null | null | null | CCCCCCn1c(=O)c2[nH]cnc2n(C)c1=O.CP(C)(=O)CCl>>CCCCCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce9a106c829041ce87d64ebe4577218f | CP(C)(=O)CCl.Cn1c(Br)nc2c1c(=O)[nH]c(=O)n2C>>Cn1c(Br)nc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | [Na].BrC1=NC=2N(C(NC(C2N1C)=O)=O)C.ClCP(C)(C)=O>>BrC1=NC=2N(C(N(C(C2N1C)=O)CP(C)(C)=O)=O)C | Cl[CH2:11][P:12]([CH3:13])([CH3:14])=[O:15].[CH3:1][n:2]1[c:3]([Br:4])[n:5][c:6]2[c:7]1[c:8](=[O:9])[nH:10][c:16](=[O:17])[n:18]2[CH3:19]>>[CH3:1][n:2]1[c:3]([Br:4])[n:5][c:6]2[c:7]1[c:8](=[O:9])[n:10]([CH2:11][P:12]([CH3:13])([CH3:14])=[O:15])[c:16](=[O:17])[n:18]2[CH3:19] | CP(C)(=O)CCl.Cn1c(Br)nc2c1c(=O)[nH]c(=O)n2C | Cn1c(Br)nc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C;D1;H3:6]-[#7;a:7]1:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]:[c:11](=[O;D1;H0:12]):[c:13]2:[#7;a:14](-[C;D1;H3:15]):[c:16]:[#7;a:17]:[c:18]:1:2>>[C;D1;H3:3]-[#15:2](-[C;D1;H3:4])(=[O;D1;H0:5])-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:8](=[O;D1;H0:9]):[#7;a:7](-[C;D1;... | null | [] | null | null | null | null | The title substance was prepared from 28 g (0.1 mol) of 8-bromo-3,7-dimethylxanthine sodium salt and chloromethyldimethylphosphine oxide analogously to Example 59 and chromatographed on silica gel.
Conditions: See reaction.notes.procedure_details.
Workup: chromatographed on silica gel | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CP(C)(=O)CCl.Cn1c(Br)nc2c1c(=O)[nH]c(=O)n2C>>Cn1c(Br)nc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7999045b166a4c6fb3a5b43a4772dfa0 | CP(C)(=O)CCCCCl.Cn1c(=O)c2[nH]cnc2n(C)c1=O>>Cn1c(=O)c2c(ncn2CCCCP(C)(C)=O)n(C)c1=O | [Na].CN1C(=O)N(C=2N=CNC2C1=O)C.ClCCCCP(C)(C)=O>>CN1C(=O)N(C=2N=CN(C2C1=O)CCCCP(C)(C)=O)C | Cl[CH2:10][CH2:11][CH2:12][CH2:13][P:14]([CH3:15])([CH3:16])=[O:17].[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][cH:8][nH:9]2)[n:18]([CH3:19])[c:20]1=[O:21]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([n:7][cH:8][n:9]2[CH2:10][CH2:11][CH2:12][CH2:13][P:14]([CH3:15])([CH3:16])=[O:17])[n:18]([CH3:19])[c:20]1=[O:21] | CP(C)(=O)CCCCCl.Cn1c(=O)c2[nH]cnc2n(C)c1=O | Cn1c(=O)c2c(ncn2CCCCP(C)(C)=O)n(C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9](=[O;D1;H0:10]):[c:11]2:[nH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]2:[#7;a:5](-[C;D1;H3:4]):[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9](=[O;D1;H0:10]):[c:11]:2:1 | null | [] | null | null | null | null | The title substance was prepared from 10.1 g (0.05 mol) of 1,3-dimethyl-xanthine sodium salt and 4-chlorobutyldimethylphosphine oxide analogously to Example 63.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | null | null | null | CP(C)(=O)CCCCCl.Cn1c(=O)c2[nH]cnc2n(C)c1=O>>Cn1c(=O)c2c(ncn2CCCCP(C)(C)=O)n(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b2bec745c38d43d2b05dd736598c1284 | CP(C)(=O)CCCCCl.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>Cn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | [Na].CN1C(NC(C=2N(C=NC12)C)=O)=O.ClCCCCP(C)(C)=O>>CN1C(N(C(C=2N(C=NC12)C)=O)CP(C)(C)=O)=O | ClCCC[CH2:10][P:11]([CH3:12])([CH3:13])=[O:14].[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7](=[O:8])[nH:9][c:15](=[O:16])[n:17]2[CH3:18]>>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7](=[O:8])[n:9]([CH2:10][P:11]([CH3:12])([CH3:13])=[O:14])[c:15](=[O:16])[n:17]2[CH3:18] | CP(C)(=O)CCCCCl.Cn1cnc2c1c(=O)[nH]c(=O)n2C | Cn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-C-C-C-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C;D1;H3:6]-[#7;a:7]1:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]:[c:11](=[O;D1;H0:12]):[c:13]2:[#7;a:14](-[C;D1;H3:15]):[c:16]:[#7;a:17]:[c:18]:1:2>>[C;D1;H3:3]-[#15:2](-[C;D1;H3:4])(=[O;D1;H0:5])-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:8](=[O;D1;H0:9]):[#7;a:7](-... | null | [] | null | null | null | null | The title substance was prepared from 10.1 g (0.05 mol) of 3,7-dimethylxanthine sodium salt and 4-chlorobutyldimethylphosphine oxide analogously to Example 63.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CP(C)(=O)CCCCCl.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>Cn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8bac5cbac8e5458191432b2c76a6fd1b | CP(C)(=O)CCCCl.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>Cn1cnc2c1c(=O)n(CCCP(C)(C)=O)c(=O)n2C | [Na].CN1C(NC(C=2N(C=NC12)C)=O)=O.ClCCCP(C)(C)=O>>CN1C(N(C(C=2N(C=NC12)C)=O)CCCP(C)(C)=O)=O | Cl[CH2:10][CH2:11][CH2:12][P:13]([CH3:14])([CH3:15])=[O:16].[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7](=[O:8])[nH:9][c:17](=[O:18])[n:19]2[CH3:20]>>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7](=[O:8])[n:9]([CH2:10][CH2:11][CH2:12][P:13]([CH3:14])([CH3:15])=[O:16])[c:17](=[O:18])[n:19]2[CH3:20] | CP(C)(=O)CCCCl.Cn1cnc2c1c(=O)[nH]c(=O)n2C | Cn1cnc2c1c(=O)n(CCCP(C)(C)=O)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[#7;a:9](-[C;D1;H3:10]):[c:11](=[O;D1;H0:12]):[nH;D2;+0:13]:[c:14](=[O;D1;H0:15]):[c:16]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:11](=[O;D1;H0:12]):[#7;a:9](-[C;D1;H3:10]):[c:8]2:[#7;a:7]:[c:6]:[#7;a:5](-[C;D1;H3:4]):[c:16]:2:[c:14]:1=[... | null | [] | null | null | null | null | The title substance was prepared from 10.1 g (0.05 mol) of 3,7-di-methylxanthine sodium salt and 3-chloropropyldimethylphosphine oxide analogously to Example 59 and crystallized from ethyl acetate.
Conditions: See reaction.notes.procedure_details.
Workup: crystallized from ethyl acetate | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CP(C)(=O)CCCCl.Cn1cnc2c1c(=O)[nH]c(=O)n2C>>Cn1cnc2c1c(=O)n(CCCP(C)(C)=O)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20ece88fc4e64225b2c8a9f117afb490 | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CP(C)(=O)CCl>>CCCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(CCCC)c1=O | C(CCC)N1C(=O)N(C=2N=CNC2C1=O)CCCC.ClCP(C)(C)=O.C([O-])([O-])=O.[K+].[K+]>>C(CCC)N1C(=O)N(C=2N=CN(C2C1=O)CP(C)(C)=O)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][nH:12]2)[n:18]([CH2:19][CH2:20][CH2:21][CH3:22])[c:23]1=[O:24].Cl[CH2:13][P:14]([CH3:15])([CH3:16])=[O:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8]2[c:9]([n:10][cH:11][n:12]2[CH2:13][P:14]([CH3:15])([CH3:16])=[O:17])[n:18]([CH2:19][CH... | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CP(C)(=O)CCl | CCCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(CCCC)c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C:10]):[c:11](=[O;D1;H0:12]):[c:13]2:[nH;D2;+0:14]:[c:15]:[#7;a:16]:[c:17]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C:10]):[c:11](=[O;D1;H0:12]):[c:13]2:[c:17]:1:[#7;a:16]:[c:15]:[n;H0;D3;+0:14]:2-[CH2;D2;+0:1]-[#15:2](-[C;D1... | null | [] | null | null | null | null | 5 g (0.01 9 mol) of 1,3-dibutylxanthine were stirred at 80° C. for 6 hours with 2.88 g (0.0228 mol) of chloromethyldimethylphosphine oxide and 3.2 g (0.0228 mol) of potassium carbonate in 80 ml of DMF. The solution was cooled to room temperature and filtered, and the filtrate was concentrated under reduced pressure. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | CN(C)C=O | null | null | CCCCn1c(=O)c2[nH]cnc2n(CCCC)c1=O.CP(C)(=O)CCl>CN(C)C=O>CCCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(CCCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-41fd0f779fc34e78b70a876533ec983f | CCCn1c(=O)c2[nH]cnc2n(CCC)c1=O.CP(C)(=O)CCl>>CCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(CCC)c1=O | C(CC)N1C(=O)N(C=2N=CNC2C1=O)CCC.ClCP(C)(C)=O>>C(CC)N1C(=O)N(C=2N=CN(C2C1=O)CP(C)(C)=O)CCC | [CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[c:8]([n:9][cH:10][nH:11]2)[n:17]([CH2:18][CH2:19][CH3:20])[c:21]1=[O:22].Cl[CH2:12][P:13]([CH3:14])([CH3:15])=[O:16]>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[c:8]([n:9][cH:10][n:11]2[CH2:12][P:13]([CH3:14])([CH3:15])=[O:16])[n:17]([CH2:18][CH2:19][CH3:20])[c:21]1=[O... | CCCn1c(=O)c2[nH]cnc2n(CCC)c1=O.CP(C)(=O)CCl | CCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(CCC)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C:10]):[c:11](=[O;D1;H0:12]):[c:13]2:[nH;D2;+0:14]:[c:15]:[#7;a:16]:[c:17]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9](-[C:10]):[c:11](=[O;D1;H0:12]):[c:13]2:[c:17]:1:[#7;a:16]:[c:15]:[n;H0;D3;+0:14]:2-[CH2;D2;+0:1]-[#15:2](-[C;D1... | null | [] | null | null | null | null | The title substance was prepared from 5 g (0.0186 mol) of 1,3-dipropyl-xanthine and 2.8 g (0.0224 mol) of chloromethyldimethylphosphine oxide analogously to Example 67.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | null | null | null | CCCn1c(=O)c2[nH]cnc2n(CCC)c1=O.CP(C)(=O)CCl>>CCCn1c(=O)c2c(ncn2CP(C)(C)=O)n(CCC)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5fefdaf5b899469aa937eb0977a556aa | BrCc1ccccc1.O=c1[nH]c(=O)n(-c2ccccc2)c2nc[nH]c12>>O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12 | [H-].[Na+].C1(=CC=CC=C1)N1C(NC(C=2NC=NC12)=O)=O.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C1=CC=CC=C1 | Br[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[n:14][cH:15][nH:16][c:24]12>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[n:14][cH:15][n:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][... | BrCc1ccccc1.O=c1[nH]c(=O)n(-c2ccccc2)c2nc[nH]c12 | O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[c:11]2:[#7;a:12]:[c:13]:[nH;D2;+0:14]:[c:15]:2:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[c:10]):[c:11]2:[#7;a:12]:[c:13]:[n;H0;D3;+0:14](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:15]:2:1 | null | [] | 25 | CELSIUS | 30 | MINUTE | 3.2 g (0.1315 mol) of sodium hydride were added in portions to a suspension of 30 g (0.1315 mol) of 3-phenylxanthine in 600 ml of DMF, the mixture was stirred at 25° C. for 30 minutes and then heated to 80° C. 27 g (0.1578 mol) of benzyl bromide were then added and the solution was left at 80° C. for 6 hours. After coo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1 | HBr | CN(C)C=O | 25 | 0.5 | BrCc1ccccc1.O=c1[nH]c(=O)n(-c2ccccc2)c2nc[nH]c12>CN(C)C=O>O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bdd1e9efc45840ebb2811f3be6d3fe5f | CP(C)(=O)CCl.O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12>>CP(C)(=O)Cn1c(=O)c2c(ncn2Cc2ccccc2)n(-c2ccccc2)c1=O | C(C1=CC=CC=C1)N1C=NC=2N(C(NC(C12)=O)=O)C1=CC=CC=C1.ClCP(C)(C)=O>>C(C1=CC=CC=C1)N1C=NC=2N(C(N(C(C12)=O)CP(C)(C)=O)=O)C1=CC=CC=C1 | Cl[CH2:5][P:2]([CH3:1])([CH3:3])=[O:4].[nH:6]1[c:7](=[O:8])[c:9]2[c:10]([n:11][cH:12][n:13]2[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:28]1=[O:29]>>[CH3:1][P:2]([CH3:3])(=[O:4])[CH2:5][n:6]1[c:7](=[O:8])[c:9]2[c:10]([n:11][cH:12][n:13]2[CH2:14][c:15]2[cH:1... | CP(C)(=O)CCl.O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12 | CP(C)(=O)Cn1c(=O)c2c(ncn2Cc2ccccc2)n(-c2ccccc2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[c:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[c:12]):[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15](-[CH2;D2;+0:1]-[#15:2](-[C;D1;H... | null | [] | null | null | null | null | The title substance was prepared from 6.5 g (0.02 mol) of 7-benzyl-3-phenylxanthine and 3.1 g (0.0245 mol) of chloromethyldimethylphosphine oxide analogously to Example 67.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CP(C)(=O)CCl.O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(Cc3ccccc3)c12>>CP(C)(=O)Cn1c(=O)c2c(ncn2Cc2ccccc2)n(-c2ccccc2)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81b4f491699b43439864ee808917472d | CP(C)(=O)Cn1c(=O)c2[nH]cnc2n(-c2ccccc2)c1=O.ClCC1CC1>>CP(C)(=O)Cn1c(=O)c2c(ncn2CC2CC2)n(-c2ccccc2)c1=O | C1(=CC=CC=C1)N1C(N(C(C=2NC=NC12)=O)CP(C)(C)=O)=O.ClCC1CC1.C([O-])([O-])=O.[K+].[K+]>>C1(CC1)CN1C=NC=2N(C(N(C(C12)=O)CP(C)(C)=O)=O)C1=CC=CC=C1 | [CH3:1][P:2]([CH3:3])(=[O:4])[CH2:5][n:6]1[c:7](=[O:8])[c:9]2[c:10]([n:11][cH:12][nH:13]2)[n:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:25]1=[O:26].Cl[CH2:14][CH:15]1[CH2:16][CH2:17]1>>[CH3:1][P:2]([CH3:3])(=[O:4])[CH2:5][n:6]1[c:7](=[O:8])[c:9]2[c:10]([n:11][cH:12][n:13]2[CH2:14][CH:15]2[CH2:16][CH2:17]2)[n:1... | CP(C)(=O)Cn1c(=O)c2[nH]cnc2n(-c2ccccc2)c1=O.ClCC1CC1 | CP(C)(=O)Cn1c(=O)c2c(ncn2CC2CC2)n(-c2ccccc2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)n(-c2ccccc2)c2ncn(CC3CC3)c12 | Cl-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[c:9]):[c:10]2:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c:14]:2:[c:15]:1=[O;D1;H0:16]>>[C:5]-[#7;a:6]1:[c:7]:[#7;a:8](-[c:9]):[c:10]2:[#7;a:11]:[c:12]:[n;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]3-[C:3]-[C:4]-3):[c:14]:2:[c:15]:1=[O;D1;H0:16] | null | [] | null | null | null | null | 3.9 g (0.0123 mol) of [1-(3-phenylxanthin-1-yl)methyl]dimethylphosphine oxide (Example 70) were stirred at 70° C. for 6 hours with 1.33 g (0.0147 mol) of chloromethylcyclopropane and 2 g of potassium carbonate. The solution was filtered and concentrated, and the residue which remained was chromatographed on silica gel ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.C1CC1.c1ccccc1 | HCl | null | null | null | CP(C)(=O)Cn1c(=O)c2[nH]cnc2n(-c2ccccc2)c1=O.ClCC1CC1>>CP(C)(=O)Cn1c(=O)c2c(ncn2CC2CC2)n(-c2ccccc2)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-42707e6a793c47a1b88ab3c47a28095a | CCCCn1cnc2c1c(=O)[nH]c(=O)n2CCCC.CP(C)(=O)CCl>>CCCCn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2CCCC | C(CCC)N1C(NC(C=2N(C=NC12)CCCC)=O)=O.ClCP(C)(C)=O>>C(CCC)N1C(N(C(C=2N(C=NC12)CCCC)=O)CP(C)(C)=O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[nH:12][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][CH2:23][CH3:24].Cl[CH2:13][P:14]([CH3:15])([CH3:16])=[O:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]1[c:10](=[O:11])[n:12]([CH2:13][P:14]([CH3:15])([CH3:16])=[O:17])[c:18](=[O:19])[n:20... | CCCCn1cnc2c1c(=O)[nH]c(=O)n2CCCC.CP(C)(=O)CCl | CCCCn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2CCCC | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]:[c:11](=[O;D1;H0:12]):[c:13]2:[#7;a:14](-[C:15]):[c:16]:[#7;a:17]:[c:18]:1:2>>[C:6]-[#7;a:7]1:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10](-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5]):[c:11](=[O;... | null | [] | null | null | null | null | The title substance was prepared from 5 g (0.0189 mol) of 3,7-dibutyl-xanthine and 2.9 g (0.0227 mol) of chloromethyldimethylphosphine oxide analogously to Example 67.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CCCCn1cnc2c1c(=O)[nH]c(=O)n2CCCC.CP(C)(=O)CCl>>CCCCn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2CCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-02b576534acf4dda8bd059063a4bc1e5 | CCn1cnc2c1c(=O)[nH]c(=O)n2C.CP(C)(=O)CCl>>CCn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | C(C)N1C=NC=2N(C(NC(C12)=O)=O)C.ClCP(C)(C)=O>>C(C)N1C=NC=2N(C(N(C(C12)=O)CP(C)(C)=O)=O)C | [CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[c:8](=[O:9])[nH:10][c:16](=[O:17])[n:18]2[CH3:19].Cl[CH2:11][P:12]([CH3:13])([CH3:14])=[O:15]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[c:8](=[O:9])[n:10]([CH2:11][P:12]([CH3:13])([CH3:14])=[O:15])[c:16](=[O:17])[n:18]2[CH3:19] | CCn1cnc2c1c(=O)[nH]c(=O)n2C.CP(C)(=O)CCl | CCn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0a7aa46051d8e94ebdb6aa279b8d844c1e6c7142c7648fe909b83533b33d80d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(=O)c2[nH]cnc2[nH]1 | Cl-[CH2;D2;+0:1]-[#15:2](-[C;D1;H3:3])(-[C;D1;H3:4])=[O;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:[c:16](=[O;D1;H0:17]):[c:18]:1:2>>[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C;D1;H3:12]):[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15](-[CH2;D2;+0:1]-[#15... | null | [] | null | null | null | null | The title substance was prepared from 5 g (0.0258 mol) of 7-ethyl-3-methylxanthine and 3.91 g (0.031 mol) of chloromethyl-dimethylphosphine oxide analogously to Example 67.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HCl | null | null | null | CCn1cnc2c1c(=O)[nH]c(=O)n2C.CP(C)(=O)CCl>>CCn1cnc2c1c(=O)n(CP(C)(C)=O)c(=O)n2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dda6f0d331b14af09fea8960240ce219 | C#CCOC1CCCCO1.[Li][CH2]CCC>>C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]1CC[C@@H]2O | C(C#C)OC1OCCCC1.C(CCC)[Li]>>C[C@@]12[C@H](CC[C@H]1[C@@H]1CCC3=CCCC[C@@H]3[C@H]1CC2)O | O([CH:6]1[CH2:15][CH2:16][CH2:17][CH2:18][O:19]1)[CH2:8][C:7]#[CH:1].[Li][CH2:12][CH2:13][CH2:14][CH3:5]>>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:7][CH2:8][C:9]4=[CH:10][CH2:11][CH2:12][CH2:13][C@H:14]34)[C@@H:15]1[CH2:16][CH2:17][C@@H:18]2[OH:19] | C#CCOC1CCCCO1.[Li][CH2]CCC | C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]1CC[C@@H]2O | null | null | CCCCCC.O1CCCC1 | C-C Coupling | OtherReaction | f0fe487d25c0d28f5ecf80713862dee3686e855314bf9b2a91ccdca8c63e5a59 | acdb5904ddc55c210135b41e065213b89f99c11736ddac9c741b3986ff999bbd | C1=C2CC[C@@H]3[C@H](CCC4CCC[C@H]43)[C@H]2CCC1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[CH2;D2;+0:4]-[Li].[CH;D1;+0:5]#[C;H0;D2;+0:6]-[CH2;D2;+0:7]-O-[CH;D3;+0:8]1-[CH2;D2;+0:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-[O;H0;D2;+0:13]-1>>[CH3;D1;+0:5]-[C:14]12-[C:15]-[C:16]-[C@@H;D3;+0:1]3-[C@H;D3;+0:2]4-[C:3]-[CH2;D2;+0:4]-[C:17]-[C:18]=[C:19]-4-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[C@H;D3;... | null | [] | null | null | null | null | As described under 3D, 460 mg of 7G is produced from 442 mg of 7F with 1.30 ml of 2-(2-propinyloxy)tetrahydro-2H-pyrane and 5.36 ml of a 15% solution of butyllithium in hexane in 70 ml of tetrahydrofuran.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Alkyne.Alkyl lithium | Secondary alcohol | C1CCOCC1 | C1=C2CC[C@H]3[C@@H]4CCC[C@@H]4CC[C@@H]3[C@H]2CCC1 | C1=C2CC[C@H]3[C@@H]4CCC[C@@H]4CC[C@@H]3[C@H]2CCC1 | Li | CCCCCC.O1CCCC1 | null | null | C#CCOC1CCCCO1.[Li][CH2]CCC>CCCCCC.O1CCCC1>C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]1CC[C@@H]2O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5b0feb349090451da9847168db764b49 | C[Si](C)(C)C#CC(CO)c1ccccc1>>C#CC(CO)c1ccccc1 | C1(=CC=CC=C1)C(CO)C#C[Si](C)(C)C.C#C>>C1(=CC=CC=C1)C(CO)C#C | C[Si](C)(C)[C:1]#[C:2][CH:3]([CH2:4][OH:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH:1]#[C:2][CH:3]([CH2:4][OH:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | C[Si](C)(C)C#CC(CO)c1ccccc1 | C#CC(CO)c1ccccc1 | null | [N+](=O)([O-])[O-].[Ag+] | C(C)O.O | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccccc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[C:3]>>[C:3]-[C:2]#[CH;D1;+0:1] | 95.8 | [{"value": 95.8, "product": "C1(=CC=CC=C1)C(CO)C#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 30 | MINUTE | 2-Phenyl-4-trimethylsilyl-but-3-yn-1-ol (Chem. Ber. (1988), 121, 1315-1320) (7.8 g) was dissolved in ethanol and the solution was cooled to -5° C. A solution of silver nitrate (8.9 g) in ethanol (60 ml) and water (21 ml) was added dropwise to the acetylene solution such that the temperature remained below 5° C. This pr... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1 | Other | [N+](=O)([O-])[O-].[Ag+].C(C)O.O | -5 | 0.5 | C[Si](C)(C)C#CC(CO)c1ccccc1>[N+](=O)([O-])[O-].[Ag+].C(C)O.O>C#CC(CO)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-df8b8caa74ee4e36b45ccc97b1be26b5 | C#CC(O)c1ccccc1.CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F>>CC(C)(C)[Si](C)(C)OCC#Cc1ccccc1 | C1(=CC=CC=C1)C(C#C)O.N1=C(C=CC=C1C)C.FC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)(F)F>>[Si](C)(C)(C(C)(C)C)OCC#CC1=CC=CC=C1 | [OH:8][CH:9]([C:10]#[CH:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.O=S(=O)(O[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])C(F)(F)F>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C:10]#[C:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C#CC(O)c1ccccc1.CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F | CC(C)(C)[Si](C)(C)OCC#Cc1ccccc1 | null | null | ClCCl | C-C Coupling | OtherReaction | 0a1a8ad872378321be89f7881dcd5d439f2f5452bc7a33fd34bacb1e47433951 | a6306d444fe93bca12cefd9b42630698965c6c5684a3e69ef152d942ec2fb46d | c1ccccc1 | F-C(-F)(-F)-S(=O)(=O)-O-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[CH;D1;+0:8]#[C:9]-[CH;D3;+0:10](-[OH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:11]-[CH2... | null | [] | null | null | 8 | HOUR | 1-Phenyl-2-propyn-1-ol (7 g) was dissolved in dichloromethane at 0° C. under nitrogen. 2,6-Lutidine (6.17 ml) was added to the solution followed by dropwise addition of tert-butyldimethylsilyl trifluoromethane sulfonate (12.16 ml); the resulting solution was stirred overnight at room temperature. The dichloromethane wa... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Secondary alcohol.Alkyne.TMS ether protective group | Alkyne.TMS ether protective group | c1ccccc1 | c1ccccc1 | c1ccccc1 | TfOH.HO- | ClCCl | null | 8 | C#CC(O)c1ccccc1.CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F>ClCCl>CC(C)(C)[Si](C)(C)OCC#Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0555bb5260f4483b896c18c9208ce891 | C=C[CH2][Mg][Cl].O=C1OCCN(Cc2ccccc2)[C@H]1c1ccc(F)cc1>>C=CC[C@@]1(O)OCCN(Cc2ccccc2)[C@H]1c1ccc(F)cc1 | C(C=C)[Mg]Cl.C(C1=CC=CC=C1)N1[C@H](C(OCC1)=O)C1=CC=C(C=C1)F>>C(C1=CC=CC=C1)N1[C@H]([C@](OCC1)(CC=C)O)C1=CC=C(C=C1)F | [Cl][Mg][CH2:3][CH:2]=[CH2:1].[C:4]1(=[O:5])[O:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C@H:17]1[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1>>[CH2:1]=[CH:2][CH2:3][C@@:4]1([OH:5])[O:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C@H:17]1[c:18]1[cH:19][... | C=C[CH2][Mg][Cl].O=C1OCCN(Cc2ccccc2)[C@H]1c1ccc(F)cc1 | C=CC[C@@]1(O)OCCN(Cc2ccccc2)[C@H]1c1ccc(F)cc1 | null | null | O1CCCC1 | C-C Coupling | Grignard from ketone to alcohol | 340c5b4861acd7077eb5e51e91a5397e9347614eafe0dce4caa5d6637efc6385 | 7b7dd1194ead8e0fe9c1abc1df4ed2591aeaeb845d1e1188a7c017e4365e9b92 | c1ccc(CN2CCOC[C@@H]2c2ccccc2)cc1 | [C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[Mg]-[Cl].[C:4]-[#7:5]1-[C:6]-[C:7]-[#8:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]-1-[c:12]>>[C:4]-[#7:5]1-[C:6]-[C:7]-[#8:8]-[C@;H0;D4;+0:9](-[OH;D1;+0:10])(-[CH2;D2;+0:3]-[C:2]=[C;D1;H2:1])-[C:11]-1-[c:12] | null | [] | null | null | 30 | MINUTE | (3S)-4-Benzyl-3-(4-fluorophenyl)-2-morpholinone (13.6 g, 47.6 mmol) was dissolved in anhydrous tetrahydrofuran (200 ml) and cooled to below -70° C. under an inert atmosphere. Allyl magnesium chloride (26.2 ml of a 2.0M solution in tetrahydrofuran; 52.4 mmol) was added dropwise over 15 minutes, maintaining the temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Allyl | Ether.Tertiary alcohol.Allyl | C1COCC[NH]1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccccc1.c1ccccc1 | Mg | O1CCCC1 | null | 0.5 | C=C[CH2][Mg][Cl].O=C1OCCN(Cc2ccccc2)[C@H]1c1ccc(F)cc1>O1CCCC1>C=CC[C@@]1(O)OCCN(Cc2ccccc2)[C@H]1c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2a3e93aba57f445fa9497b301fde8efd | COc1ccccc1Br>>COc1ccccc1B(O)O | B(OC)(OC)OC.C(CCC)[Li].BrC1=C(C=CC=C1)OC.Cl>>COC1=C(C=CC=C1)B(O)O | Br[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[B:9]([OH:10])[OH:11] | COc1ccccc1Br | COc1ccccc1B(O)O | null | null | O1CCCC1 | Functional Group Interconversion | Preparation of boronic acids without boronic ether | ea18136a2a812ba75d88f0154de74a11e900f53593099ed5cfbdc7bb208ca0bd | 3c67ef5cce82b121a680ae296eb1f6d78abe8f9494b62ca3b872477b7553bcfd | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[#5:7](-[O;D1;H1:8])-[O;D1;H1:9]):[c:2]:[c:3] | 100.4 | [{"value": 97.0, "product": "COC1=C(C=CC=C1)B(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.4, "product": "COC1=C(C=CC=C1)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | n-Butyl lithium (13.0 ml of a 1.6M solution in hexanes, 19.8 mmol) was added dropwise to a solution of 2-bromoanisole (3.74 g, 19.0 mmol) in anhydrous tetrahydrofuran (15 ml) cooled to below -70° C., maintaining the temperature during the addition below -60° C. The solution was stirred for 20 minutes before the additio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | O1CCCC1 | null | null | COc1ccccc1Br>O1CCCC1>COc1ccccc1B(O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-622fcecd2a0b4607a07fac649d6051df | O=Cc1ccccc1C(F)(F)F>>FC(F)(F)c1ccccc1C1CO1 | FC(C=1C(=CC=CC1)C=O)(F)F.ICCl.C[Li]>>FC(C1=C(C=CC=C1)C1OC1)(F)F | [F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[O:13]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]1[CH2:12][O:13]1 | O=Cc1ccccc1C(F)(F)F | FC(F)(F)c1ccccc1C1CO1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 2d8c350316fb727aeda6536184083b71a9b20f0ee07455d6d3abcb377b9f555a | e21ccb4bcf9a71eccf327a93a1fa5572944710ed52ebac44dc7df03f0c63c123 | c1ccc(C2CO2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[c:4]:[c:3](-[CH;D3;+0:2]1-[C:6]-[O;H0;D2;+0:1]-1):[c:5] | null | [] | -78 | CELSIUS | null | null | α,α,α-trifluoro-o-tolualdehyde (3 g) was dissolved in anhydrous tetrahydrofuran and cooled to -78° C., iodochloromethane (1.38 ml) was then added, followed by methyllithium (1.5M complexed with lithium bromide) (12 ml) added over 5 minutes. The reaction was left to warm up to room temperature overnight. The reaction wa... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Ether | null | C1CO1 | c1ccccc1.C1CO1 | Other | O1CCCC1 | -78 | null | O=Cc1ccccc1C(F)(F)F>O1CCCC1>FC(F)(F)c1ccccc1C1CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a8bce93f6c044b885e4e50a87273179 | Cc1ccc(S(=O)(=O)Cl)cc1.OCc1c[nH]cn1>>Cc1ccc(S(=O)(=O)n2cnc(CO)c2)cc1 | Cl.OCC=1N=CNC1.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)N(CC)CC>>OCC=1N=CN(C1)S(=O)(=O)C1=CC=C(C=C1)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1)(=[O:7])=[O:8].[nH:9]1[cH:10][n:11][c:12]([CH2:13][OH:14])[cH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][n:11][c:12]([CH2:13][OH:14])[cH:15]2)[cH:16][cH:17]1 | Cc1ccc(S(=O)(=O)Cl)cc1.OCc1c[nH]cn1 | Cc1ccc(S(=O)(=O)n2cnc(CO)c2)cc1 | null | null | ClCCl | Acylation | OtherReaction | 38070f7d9f34add00574825d6ccf49150840a76858769a46bd35f61e9d7862ae | b7cf703ff8ec1befb0c6e5230d29d7904f3e22c3606b15633c7e7a7fc4abca48 | O=S(=O)(c1ccccc1)n1ccnc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[c:8]1:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1>>[C:7]-[c:8]1:[#7;a:9]:[c:10]:[n;H0;D3;+0:11](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):[c:12]:1 | 80 | [{"value": 80.0, "product": "OCC=1N=CN(C1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "OCC=1N=CN(C1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-Hydroxymethylimidazole hydrochloride (10 g) was suspended in dichloromethane (200 ml). ρ-Toluenesulfonyl chloride (15.58 g) was added and triethylamine (25.8 ml) was added dropwise to the stirred reaction mixture which was allowed to stir at room temperature overnight. The mixture was washed with water (2×100 ml) and... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HCl | ClCCl | null | 8 | Cc1ccc(S(=O)(=O)Cl)cc1.OCc1c[nH]cn1>ClCCl>Cc1ccc(S(=O)(=O)n2cnc(CO)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81fec9f4834b4c55afc33fdf0315e395 | 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-fa7780e37be9447bbaf8e57cbcbe5c93 | 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-4458b736f18f41ab812293845f07a670 | 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-d16063bc2b004a4189a712a254c9912b | 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-b5f509f406ce44cc9d59d96a369153b8 | 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-l,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-d99b336bab874ba9a769f33bfde68ea1 | C#CC1CCCCC1.C=O>>OCC#CC1CCCCC1 | C(C)[Mg]Br.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 magnesium 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 formaldeh... | 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-5f7f1d1943894178b387870f0ce435aa | 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-08d5189834b7446baa12a49af6278da7 | 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-2c3cde5cb45a452d9dc003d173196948 | 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-3230ec97664440b59969f4a912460e21 | 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-e87aace35dd246b89ebaa26756e4c33e | 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-9c164006b8de489282c7ebec5d3e8a36 | 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-1b205afa162546af9bd7761e748d6661 | 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-a1221841f9ed4c668ce3cbb810a9131e | 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-b5bbc1a7d84f4bde9e1c12389dbc8bce | 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-659db74553d64bf48014a84d116f5718 | 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-06bfd03f154d4600bce4486454c4cfc1 | 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-a8f8ef59267442b7ad02cb6e759c0c32 | 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-e72b10113d3543aebcfaa094ed2a781a | 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-2f3265d28f2a442e9260aa23c827a764 | 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-98ad3a1cf50b4a51a88db33c7e3d6103 | 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-8d71e329d3a24e58bfc766321a0c2a83 | 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-20add643e25f4ff484bb9c80dc811185 | 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 chIoroacetyl 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-be3327987e254f7c83d2e21521f5ed8d | 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-7cb3a69bcc7d401383fe8305bf483874 | 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-86a6b338addf413b9e8f29662d8d58d4 | 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 hexan... | 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-a02c0eb3e0774586ad570d8875582725 | 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-46f9ee0ab4934b5985b42b8009b8134d | 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-3f4808599fe74e18a7bf471d2d4e9057 | CCOC(=O)N1CCN(c2ccc(-n3cnn(C(CC)C(=O)c4ccc(Cl)cc4)c3=O)cn2)CC1>>CCC(C(=O)c1ccc(Cl)cc1)n1ncn(-c2ccc(N3CCNCC3)nc2)c1=O.Cl | ClC1=CC=C(C(=O)C(CC)N2N=CN(C2=O)C=2C=CC(=NC2)N2CCN(CC2)C(=O)OCC)C=C1>>Cl.ClC1=CC=C(C(=O)C(CC)N2N=CN(C2=O)C=2C=NC(=CC2)N2CCNCC2)C=C1 | CCOC(=O)[N:24]1[CH2:23][CH2:22][N:21]([c:20]2[cH:19][cH:18][c:17](-[n:16]3[cH:15][n:14][n:13]([CH:3]([CH2:2][CH3:1])[C:4](=[O:5])[c:6]4[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]4)[c:29]3=[O:30])[cH:28][n:27]2)[CH2:26][CH2:25]1>>[CH3:1][CH2:2][CH:3]([C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[n:13]1[n:14... | CCOC(=O)N1CCN(c2ccc(-n3cnn(C(CC)C(=O)c4ccc(Cl)cc4)c3=O)cn2)CC1 | CCC(C(=O)c1ccc(Cl)cc1)n1ncn(-c2ccc(N3CCNCC3)nc2)c1=O.Cl | null | null | Br.O | Miscellaneous | Hydrogenolysis of tertiary amines | 5e65a693282cf0da3cddb6131d73a578944c81ca51b95c5494565f35e3163260 | ce1d20ece0ee3db84a8954171912e0cc035fe478f2082f416fe209b2e3984b26 | O=C(Cn1ncn(-c2ccc(N3CCNCC3)nc2)c1=O)c1ccccc1 | C-C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 39.4 | [{"value": 39.4, "product": "Cl.ClC1=CC=C(C(=O)C(CC)N2N=CN(C2=O)C=2C=NC(=CC2)N2CCNCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "Cl.ClC1=CC=C(C(=O)C(CC)N2N=CN(C2=O)C=2C=NC(=CC2)N2CCNCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (±)-ethyl 4-[5-[2-[1-(4-chlorobenzoyl)propyl]-2,3-dihydro-3-oxo-4H-1,2,4-triazol-4-yl]-2-pyridinyl]-1-piperazinecarboxylate (24 g) in hydrobromic acid, 48% solution in water (250 ml) was stirred and refluxed overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2, neutralized with NH4... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ncn[nH]1.c1ccncc1.C1C[NH]CCN1 | HO- | Br.O | null | null | CCOC(=O)N1CCN(c2ccc(-n3cnn(C(CC)C(=O)c4ccc(Cl)cc4)c3=O)cn2)CC1>Br.O>CCC(C(=O)c1ccc(Cl)cc1)n1ncn(-c2ccc(N3CCNCC3)nc2)c1=O.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a998f07f4214c4e80efb60ca50f068e | CS(=O)(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1.NN>>CS(=O)(=O)Cc1ccc(C(=NN)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C)C=C1.O.NN.C(C)O>>ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NN)C=C1 | O=[C:10]([c:9]1[cH:8][cH:7][c:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:21][cH:20]1)[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1.[NH2:11][NH2:12]>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[N:11][NH2:12])[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | CS(=O)(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1.NN | CS(=O)(=O)Cc1ccc(C(=NN)c2ccc(Cl)cc2)cc1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 83882590079d324612170330ec542715e8ce71411b1b2946e5f0d75ea75ad4dd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | N=C(c1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[N;D1;H2:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7] | 97 | [{"value": 97.0, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NN)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NN)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | 4-chloro-4'-methylsulfonylmethylbenzophenone (10.0 g) and hydrazine monohydrate (4.9 g) were added to ethanol (200 ml) and acetic acid (10 ml), and the mixture was stirred for 6 hours under reflux. The reaction mixture was concentrated, and the residue was extracted with ethyl acetate. The ethyl acetate layer was washe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O | null | 6 | CS(=O)(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1.NN>C(C)(=O)O>CS(=O)(=O)Cc1ccc(C(=NN)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71fa5a93fb9c483491defb7a5b1de773 | CS(=O)(=O)Cc1ccc(C(=NN)c2ccc(Cl)cc2)cc1.O=C=NS(=O)(=O)Cl>>CS(=O)(=O)Cc1ccc(C(=NNC(N)=O)c2ccc(Cl)cc2)cc1 | O.ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NN)C=C1.ClS(=O)(=O)N=C=O.C(C)(=O)OCC>>ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NNC(=O)N)C=C1 | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[N:11][NH2:12])[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[cH:23][cH:24]1.O=S(=O)(Cl)[N:14]=[C:13]=[O:15]>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[N:11][NH:12][C:13]([NH2:14])=[O:15])[c:16]2[cH:17][cH:18][c:19]([Cl:2... | CS(=O)(=O)Cc1ccc(C(=NN)c2ccc(Cl)cc2)cc1.O=C=NS(=O)(=O)Cl | CS(=O)(=O)Cc1ccc(C(=NNC(N)=O)c2ccc(Cl)cc2)cc1 | null | null | CCCCCC | Acylation | OtherReaction | 57a190aa2d46f01df5cba31494a42077addc24d6d4df478867374ee8486ae181 | f56bae9e96d767a807f344bd96cd64e42032f959b18aae195ae8c6f23ca68ca8 | N=C(c1ccccc1)c1ccccc1 | Cl-S(=O)(=O)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=[O;D1;H0:3].[NH2;D1;+0:4]-[#7:5]=[C:6](-[c:7])-[c:8]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[NH;D2;+0:4]-[#7:5]=[C:6](-[c:7])-[c:8] | 81.5 | [{"value": 80.0, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NNC(=O)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C)=NNC(=O)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-chloro-4'-methylsulfonylmethylbenzophenone-hydrazone (1.3 g) and chlorosulfonyl isocyanate (0.63 g) were added to ethyl acetate (100 ml), and the mixture was stirred for one hour at room temperature. Then, water (100 ml) was added, and the mixture was further stirred for 16 hours at room temperature. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Hydrazone amide.Urea | null | null | c1ccccc1.c1ccccc1 | Other | CCCCCC | null | 1 | CS(=O)(=O)Cc1ccc(C(=NN)c2ccc(Cl)cc2)cc1.O=C=NS(=O)(=O)Cl>CCCCCC>CS(=O)(=O)Cc1ccc(C(=NNC(N)=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3e56139cc6e34a43b00746088801690f | Cl>>Cl | ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)NNC(=O)OC)C=C1.Cl>>Cl.ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)NNC(=O)OC)C=C1 | [ClH:29]>>[ClH:29] | Cl | Cl | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 91.5 | [{"value": 91.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-(4-chloro-4'-trifluoromethylsulfonylmethylbenzhydryl) -N'-methoxycarbonylhydrazine (1.6 g) was added to methanol (80 ml), and hydrochloric acid (3 ml) was added thereto with stirring at room temperature. The mixture was gradually heated to the reflux temperature and stirred for 2 hours under reflux, and then it was l... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | Cl>CO>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ade4f0eddda041248b4ac3c87079d5f2 | CS(=O)[O-].O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1>>CS(=O)(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | BrCC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1.CS(=O)[O-].[Na+].CN(C=O)C>>ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C)C=C1 | [CH3:1][S:2](=[O:3])[O-:4].Br[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[cH:19][cH:20]1>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[cH:19][cH:20]1 | CS(=O)[O-].O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1 | CS(=O)(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | null | null | O | Oxidation | OtherReaction | 4e368b59131379295489552aefe4cb307196d5ed5086c1fceb04499cafc83fc9 | dc22ffd0e03e7a0cb48e41cac2adc2520131875b015e35bfc34589909b4ea449 | O=C(c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[S;H0;D3;+0:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C;D1;H3:5]-[S;H0;D4;+0:6](=[O;D1;H0:8])(=[O;H0;D1;+0:7])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 90.6 | [{"value": 90.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 4-bromomethyl-4'-chlorobenzophenone (3.1 g) and sodium methanesulfinate (1.5 g) were added to N,N-dimethylformamide (50 ml), and the mixture was stirred for 16 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Sulfone | null | null | c1ccccc1.c1ccccc1 | Br- | O | null | 16 | CS(=O)[O-].O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1>O>CS(=O)(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-854622046616431a8dec648c46bb4905 | CCBr.O=C(c1ccc(Cl)cc1)c1ccc(CS)cc1>>CCSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS)C=C1.C(C)Br.[OH-].[K+]>>ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSCC)C=C1 | Br[CH2:2][CH3:1].[SH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1>>[CH3:1][CH2:2][S:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | CCBr.O=C(c1ccc(Cl)cc1)c1ccc(CS)cc1 | CCSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | O=C(c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C;D1;H3:2].[SH;D1;+0:3]-[C:4]-[c:5]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:3]-[C:4]-[c:5] | 79.1 | [{"value": 79.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-chloro-4'-mercaptomethylbenzophenone (16.0 g), ethyl bromide (7.4 g) and potassium hydroxide (4.3 g) were added to methanol (250 ml), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was cooled to room temperature and then concentrated. Water was added to the residue, and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1 | HBr | CO | null | 0.5 | CCBr.O=C(c1ccc(Cl)cc1)c1ccc(CS)cc1>CO>CCSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54662bdd64d74fb6bcb38cb65a7a5fc0 | FC(F)Cl.O=C(c1ccc(Cl)cc1)c1ccc(CS)cc1>>O=C(c1ccc(Cl)cc1)c1ccc(CSC(F)F)cc1 | FC(F)Cl.ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS)C=C1.[OH-].[K+].O1CCOCC1.ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS)C=C1>>ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC(F)F)C=C1 | Cl[CH:16]([F:17])[F:18].[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([CH2:14][SH:15])[cH:19][cH:20]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([CH2:14][S:15][CH:16]([F:17])[F:18])[cH:19][cH:20]1 | FC(F)Cl.O=C(c1ccc(Cl)cc1)c1ccc(CS)cc1 | O=C(c1ccc(Cl)cc1)c1ccc(CSC(F)F)cc1 | null | null | O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | c11e7b334ae63e4740643fbd6c74ad7fdeadc14d9c02081f02986baac1833658 | 20b145837f0eb6ec08b59738f160c59836d7f6fb307d6ce14718c9edce0ba5a3 | O=C(c1ccccc1)c1ccccc1 | Cl-[CH;D3;+0:1](-[F;D1;H0:2])-[F;D1;H0:3].[SH;D1;+0:4]-[C:5]-[c:6]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[S;H0;D2;+0:4]-[C:5]-[c:6] | 36 | [{"value": 36.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-chloro-4'-mercaptomethylbenzophenone (14.7 g) and potassium hydroxide (15 g) was added to a solvent comprising dioxane (100 ml) and water (100 ml). Difluoromethyl chloride was blown into this solution at 60° C. until the starting material 4-chloro-4'-mercaptomethylbenzophenone disappeared. The reaction product was co... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Aliphatic thiol | Secondary halide.Secondary halide.Monosulfide | null | null | c1ccccc1.c1ccccc1 | HCl | O | null | null | FC(F)Cl.O=C(c1ccc(Cl)cc1)c1ccc(CS)cc1>O>O=C(c1ccc(Cl)cc1)c1ccc(CSC(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f13ed1df908340769124c76cde4ad555 | CS.O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1>>CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | BrCC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1.CS.[Na]>>ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC)C=C1 | [CH3:1][SH:2].Br[CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[cH:17][cH:18]1>>[CH3:1][S:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | CS.O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1 | CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | O=C(c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[SH;D1;+0:6]>>[C;D1;H3:5]-[S;H0;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 83 | [{"value": 83.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-bromomethyl-4'-chlorobenzophenone (3.1 g) and 15% methylmercaptan-sodium aqueous solution (5.6 g) were added to methanol (150 ml), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dri... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1 | HBr | CO | null | 0.5 | CS.O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1>CO>CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-27d91eecd20e450da1b8e17f791b0eaa | CO.CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1>>CS(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC)C=C1.CO.I(=O)(=O)(=O)[O-].[Na+]>>ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)C)C=C1 | C[OH:3].[CH3:1][S:2][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1>>[CH3:1][S:2](=[O:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | CO.CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | CS(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | null | null | O | Oxidation | Sulfanyl to sulfinyl_MeOH | 4a704b0639e45d740e643f16a773bf4572c6aab8d132b11af488cbe19ddcc846 | 15e07f01a9f59e25d78fc6b29acfa668d39c54811075ff79fa2a74cea51f03d7 | O=C(c1ccccc1)c1ccccc1 | C-[OH;D1;+0:1].[C;D1;H3:2]-[S;H0;D2;+0:3]-[C:4]-[c:5]>>[C;D1;H3:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:1])-[C:4]-[c:5] | 93 | [{"value": 93.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 4-chloro-4'-methylthiomethylbenzophenone (4.2 g) was added to methanol (150 ml). Sodium periodate (3.6 g) dissolved in water (20 ml), was added to this solution, and the mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated, and water was added thereto. The mixture was extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Methanol | Sulfoxide | null | null | c1ccccc1.c1ccccc1 | Other | O | null | 16 | CO.CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1>O>CS(=O)Cc1ccc(C(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8621c7ae01154702b393326bf088b608 | O=C(c1ccc(Cl)cc1)c1ccc(CS(=O)(=O)CCCBr)cc1>>O=C(c1ccc(Cl)cc1)c1ccc(C2CCCS2(=O)=O)cc1 | BrCCCS(=O)(=O)CC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1.[H-].[Na+].CN(C(C)=O)C>>ClC1=CC=C(C(=O)C2=CC=C(C=C2)C2S(CCC2)(=O)=O)C=C1 | Br[CH2:15][CH2:16][CH2:17][S:18]([CH2:14][c:13]1[cH:12][cH:11][c:10]([C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]2)[cH:22][cH:21]1)(=[O:19])=[O:20]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([CH:14]2[CH2:15][CH2:16][CH2:17][S:18]2(=[O:19])=[O:20])[cH:21][cH:22]1 | O=C(c1ccc(Cl)cc1)c1ccc(CS(=O)(=O)CCCBr)cc1 | O=C(c1ccc(Cl)cc1)c1ccc(C2CCCS2(=O)=O)cc1 | null | null | O | Functional Group Interconversion | OtherReaction | 029b3c84eb5cf933dfc883c7e414060b45b72ca4f91c1236e0a3eb3f70aa0c16 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | O=C(c1ccccc1)c1ccc(C2CCCS2(=O)=O)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[#16:4]1(=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:7]-1-[c:8](:[c:9]):[c:10] | 50 | [{"value": 50.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)C2S(CCC2)(=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 4-(3-bromopropyl)sulfonylmethyl-4'-chlorobenzophenone (2.5 g) and 60% sodium hydride (0.3 g) were added to N,N-dimethylacetamide (70 ml), and the mixture was stirred for 16 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | C1CCSC1 | c1ccccc1.c1ccccc1.C1CCSC1 | HBr | O | null | 16 | O=C(c1ccc(Cl)cc1)c1ccc(CS(=O)(=O)CCCBr)cc1>O>O=C(c1ccc(Cl)cc1)c1ccc(C2CCCS2(=O)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39af67312f5442e6ae004f66e6de33ad | N#C[S-].O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1>>N#CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | BrCC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1.[S-]C#N.[Na+].C(C)O>>ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC#N)C=C1 | [N:1]#[C:2][S-:3].Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1>>[N:1]#[C:2][S:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | N#C[S-].O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1 | N#CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4f905981579db6f2866cc0ae1b975a1e274bbb1d618959665eb6b8e4dd6684b9 | e26f642c2dc9d150597dcc73347fb476ddd5d717501944aafd09c0558413a369 | O=C(c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H0:5]#[C:6]-[S-;H0;D1:7]>>[N;D1;H0:5]#[C:6]-[S;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 42 | [{"value": 42.0, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.5, "product": "ClC1=CC=C(C(=O)C2=CC=C(C=C2)CSC#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | 4-bromomethyl-4'-chlorobenzophenone (5.7 g) and sodium thiocyanate (5.5 g) were added to ethanol (50 ml), and the mixture was stirred for one hour at 60° C. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Monosulfide | null | null | c1ccccc1.c1ccccc1 | Br- | C(C)(=O)OCC | 60 | 1 | N#C[S-].O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1>C(C)(=O)OCC>N#CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d7170f4c2ba43dc88cc7ef00696f625 | O=C(c1ccc(Cl)cc1)c1ccc(CS(=O)(=O)C(F)(F)F)cc1>>O=S(=O)(Cc1ccc(C(O)c2ccc(Cl)cc2)cc1)C(F)(F)F | ClC1=CC=C(C(=O)C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)C=C1.[BH4-].[Na+]>>ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)O)C=C1 | [O:1]=[S:2](=[O:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1)[C:20]([F:21])([F:22])[F:23]>>[O:1]=[S:2](=[O:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:18][cH:19]1)[C:20]([F:21])([F:22])[... | O=C(c1ccc(Cl)cc1)c1ccc(CS(=O)(=O)C(F)(F)F)cc1 | O=S(=O)(Cc1ccc(C(O)c2ccc(Cl)cc2)cc1)C(F)(F)F | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2ccccc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | 77 | [{"value": 77.0, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)C(F)(F)F)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-chloro-4'-trifluoromethylsulfonylmethylbenzophenone (5.5 g) was dispersed in methanol (200 ml). Sodium borohydride was gradually added thereto at room temperature with stirring, and the mixture was further stirred overnight at room temperature. After completion of the reaction, methanol was distilled off under reduce... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | null | CO | null | null | O=C(c1ccc(Cl)cc1)c1ccc(CS(=O)(=O)C(F)(F)F)cc1>CO>O=S(=O)(Cc1ccc(C(O)c2ccc(Cl)cc2)cc1)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9900c0905406446f8afdb6d500c86aee | CCS(=O)(=O)Cc1ccc(C(O)c2ccc(Cl)cc2)cc1.O=S(Cl)Cl>>CCS(=O)(=O)Cc1ccc(C(Cl)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)CC)O)C=C1.S(=O)(Cl)Cl.C1(=CC=CC=C1)C>>ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)CC)Cl)C=C1 | O[CH:11]([c:10]1[cH:9][cH:8][c:7]([CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:21][cH:20]1)[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1.O=S(Cl)[Cl:12]>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([Cl:12])[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | CCS(=O)(=O)Cc1ccc(C(O)c2ccc(Cl)cc2)cc1.O=S(Cl)Cl | CCS(=O)(=O)Cc1ccc(C(Cl)c2ccc(Cl)cc2)cc1 | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1ccc(Cc2ccccc2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[Cl;H0;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | 75 | [{"value": 75.0, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)CS(=O)(=O)CC)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-chloro-4'-ethane sulfonylmethylbenzhydrol (6.0 g), thionyl chloride (5.4 g), toluene (200 ml) and a catalytic amount of N,N-dimethylformamide were mixed and gradually heated with stirring to a refluxing temperature. The mixture was stirred for 4 hours under reflux and then left to cool. Then, the solvent was distille... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | null | CCS(=O)(=O)Cc1ccc(C(O)c2ccc(Cl)cc2)cc1.O=S(Cl)Cl>CN(C=O)C>CCS(=O)(=O)Cc1ccc(C(Cl)c2ccc(Cl)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3fcddcded91a4fbd88eca5020df9e5da | 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-01437a3fcaad437da9c411fa39cdbc01 | 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 |
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