dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a62cae018b8c45d6b9035dabbb8fdbce | CO.COc1nc(Cl)cc(I)c1C=O>>COCc1c(I)cc(Cl)nc1OC | FC(C(=O)O)(F)F.ClC1=CC(=C(C(=N1)OC)C=O)I.C(C)[SiH](CC)CC.CO.C(=O)(O)[O-].[Na+]>>ClC1=NC(=C(C(=C1)I)COC)OC | O[CH3:1].[O:2]=[CH:3][c:4]1[c:5]([I:6])[cH:7][c:8]([Cl:9])[n:10][c:11]1[O:12][CH3:13]>>[CH3:1][O:2][CH2:3][c:4]1[c:5]([I:6])[cH:7][c:8]([Cl:9])[n:10][c:11]1[O:12][CH3:13] | CO.COc1nc(Cl)cc(I)c1C=O | COCc1c(I)cc(Cl)nc1OC | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 1d76918cc19966c7516bfe9a97a96abd1d20ff1b6b551b7a2a7721be5b12e885 | a9e58bdb270b8602210135fa12a97050bf42474a87c9f2c3a2f396b5330373a5 | c1ccncc1 | O-[CH3;D1;+0:1].[#8:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[CH;D2;+0:7]=[O;H0;D1;+0:8]):[c:9]>>[#8:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[CH3;D1;+0:1]):[c:9] | null | [] | 25 | CELSIUS | 14 | HOUR | To a mixture of 6-chloro-4-iodo-2-methoxy-3-pyridinecarboxaldehyde (1.07 g, 3.60 mmol), triethylsilane (0.86 mL, 5.40 mmol) and methanol (0.43 mL, 10.6 mmol) at 0° C. was added trifluoroacetic acid (2.2 mL, 28.6 mmol), and the resulting solution was stirred at 25° C. for 14 h. After dilution with ether (30 mL), saturat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Methanol | Ether | null | null | c1ccncc1 | Other | CCOCC | 25 | 14 | CO.COc1nc(Cl)cc(I)c1C=O>CCOCC>COCc1c(I)cc(Cl)nc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bf42ea30b38f46aa809f3ee355b8012d | CN(C)C=O.Clc1ccc2ccccc2n1>>O=Cc1cc2ccccc2nc1Cl | CN(C=O)C.ClC1=NC2=CC=CC=C2C=C1.C(C)(C)NC(C)C.[Li]CCCC>>ClC1=NC2=CC=CC=C2C=C1C=O | CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[Cl:13]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[Cl:13] | CN(C)C=O.Clc1ccc2ccccc2n1 | O=Cc1cc2ccccc2nc1Cl | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2fb6a63f37a90389382989ea42f8436574f9d339310d3a9ddc749d75d88d7d6b | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc2ncccc2c1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Cl;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[Cl;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 92.2 | [{"value": 92.0, "product": "ClC1=NC2=CC=CC=C2C=C1C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "ClC1=NC2=CC=CC=C2C=C1C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 0.46 mL (3.30 mmol) of diisopropylamine in 8 mL of THF at 0° C. was added 1.53 mL (3.30 mmol) of n-BuLi dropwise. After 20 min the solution was cooled to -78° C. and 2-chloroquinoline (491 mg, 3.0 mmol) was added neat. The mixture was stirred at -78° C. for 30 min, then dimethylformamide (0.39 mL, 5.04... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Other | C1CCOC1 | -78 | 0.5 | CN(C)C=O.Clc1ccc2ccccc2n1>C1CCOC1>O=Cc1cc2ccccc2nc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-12269c99e5404be9b05d3835e65be89c | O=Cc1cc2ccccc2nc1I>>OCc1cc2ccccc2nc1I | IC1=NC2=CC=CC=C2C=C1C=O.[BH4-].[Na+]>>OCC=1C(=NC2=CC=CC=C2C1)I | [O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13]>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13] | O=Cc1cc2ccccc2nc1I | OCc1cc2ccccc2nc1I | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc2ncccc2c1 | [I;D1;H0:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]>>[I;D1;H0:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8] | 84.4 | [{"value": 84.0, "product": "OCC=1C(=NC2=CC=CC=C2C1)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "OCC=1C(=NC2=CC=CC=C2C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a stirred solution of 2-iodo-3-quinolinecarboxaldehyde (595 mg, 2.10 mmol) in 40 mL of CH3OH at 0° C. was added NaBH4 (86 mg, 2.31 mmol), and the mixture was stirred at 0° C. for 30 min. After concentrating the mixture to approximately one-half of its original volume, water (30 mL) was added and the mixture was allo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccc2ncccc2c1 | null | CO | 0 | 0.5 | O=Cc1cc2ccccc2nc1I>CO>OCc1cc2ccccc2nc1I |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ec43efed8217448c8a53e867f44dee4e | O=C1CCC(=O)N1Cl.OCc1cc2ccccc2nc1I>>ClCc1cc2ccccc2nc1I | C(=O)(O)[O-].[Na+].OCC=1C(=NC2=CC=CC=C2C1)I.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.ClN1C(CCC1=O)=O>>ClCC=1C(=NC2=CC=CC=C2C1)I | O=C1CCC(=O)N1[Cl:1].O[CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13]>>[Cl:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13] | O=C1CCC(=O)N1Cl.OCc1cc2ccccc2nc1I | ClCc1cc2ccccc2nc1I | null | null | CN(C)C=O | Functional Group Interconversion | Alcohol to chloride_Other | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccc2ncccc2c1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[I;D1;H0:5]):[#7;a:6]:[c:7].O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:8]>>[Cl;H0;D1;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[I;D1;H0:5]):[#7;a:6]:[c:7] | 84 | [{"value": 84.0, "product": "ClCC=1C(=NC2=CC=CC=C2C1)I", "details": "PERCENTYIELD", "is_desired": false}] | -23 | CELSIUS | 1 | HOUR | To a stirred mixture of 3-hydroxymethyl-2-iodoquinoline prepared in accordance with Example 10 above (350 mg, 1.23 mmol) and triphenylphosphine (483 mg, 1.84 mmol) in 10 mL of dry DMF at -23° C. was added N-chlorosuccinimide (246 mg, 1.84 mmol), and the mixture was stirred for 1 h at -23° C. After the addition of 40 mL... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccc2ncccc2c1 | HO- | CN(C)C=O | -23 | 1 | O=C1CCC(=O)N1Cl.OCc1cc2ccccc2nc1I>CN(C)C=O>ClCc1cc2ccccc2nc1I |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86a11031d1d743c286db830c75a75df3 | OCCCCCCCCO.[N-]=[N+]=[N-]>>[N-]=[N+]=NCCCCCCCCO | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(CCCCCCCO)O.C(C)(=O)OCC.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CCCCCCCCO | O[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12] | OCCCCCCCCO.[N-]=[N+]=[N-] | [N-]=[N+]=NCCCCCCCCO | null | null | CN(C=O)C.N1=CC=CC=C1.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | b6ef7629d0f9b9d1438b20ee6805124558e67d10777a15184211800dd3e8b973 | a446353c66aa2c48beeb0e3765234578855c107c1200bfc64cebc8b68d490616 | null | O-[CH2;D2;+0:1]-[C:2]-[C:3].[N-;H0;D1:4]=[#7;+:5]=[N;-;D1;H0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D2;+0:4]=[#7;+:5]=[N;-;D1;H0:6] | null | [] | 10 | CELSIUS | null | null | 14.65 g of 1,8-octanediol was dissolved in 80 g of pyridine, and cooled to 10° C. A solution of 19 g p-toluenesulfonyl chloride in 70 ml anhydrous methylene chloride was added dropwise thereto, and the mixture was heated gradually overnight for reaction. After water washing, the solvent was removed by distillation, to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Azide | null | null | null | HO- | CN(C=O)C.N1=CC=CC=C1.C(Cl)Cl | 10 | null | OCCCCCCCCO.[N-]=[N+]=[N-]>CN(C=O)C.N1=CC=CC=C1.C(Cl)Cl>[N-]=[N+]=NCCCCCCCCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dcadfe0e1eca4e47a8b88dad58fe8309 | CCCCCCCCCCCCCCCC(=O)Cl.NCCO>>CCCCCCCCCCCCCCCC(=O)NCCO | NCCO.C(CCCCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCCCCCC)(=O)NCCO | Cl[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].[NH2:18][CH2:19][CH2:20][OH:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][OH:21] | CCCCCCCCCCCCCCCC(=O)Cl.NCCO | CCCCCCCCCCCCCCCC(=O)NCCO | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | 2-Aminoethanol (13.76 g, 225.3 mmol) was dissolved in CHCl3 (750 ml). To the solution was added dropwise palmitoyl chloride (15.48 g, 56.3 mmol) with stirring under ice cooling. Thereafter, the mixture was stirred at room temperature for 19 hours.
Conditions: See reaction.notes.procedure_details.
Workup: Thereafter, th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HCl | C(Cl)(Cl)Cl | null | null | CCCCCCCCCCCCCCCC(=O)Cl.NCCO>C(Cl)(Cl)Cl>CCCCCCCCCCCCCCCC(=O)NCCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-146b31ec172a43eb9907724661a2a7f5 | O=C(O)c1c(C(=O)O)c2ccccc2[nH]c1=O>>O=C1OC(=O)c2c1c(=O)[nH]c1ccccc21 | C1=CC=C2C(=C1)C(=C(C(=O)N2)C(=O)O)C(=O)O.P(=O)(Cl)(Cl)Cl>>C1(OC(C=2C(NC=3C=CC=CC3C21)=O)=O)=O | O[C:2](=[O:1])[c:7]1[c:6]([C:4]([OH:3])=[O:5])[c:16]2[c:11]([nH:10][c:8]1=[O:9])[cH:12][cH:13][cH:14][cH:15]2>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](=[O:9])[nH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]21 | O=C(O)c1c(C(=O)O)c2ccccc2[nH]c1=O | O=C1OC(=O)c2c1c(=O)[nH]c1ccccc21 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 6d51ecee017f321f8f64e74774842c818b7e862119463d0ba723ecec3dc0defe | 22fb50577915472f1babb105381e408122dc09b3472eabb73e6e4daecfef90f6 | O=C1OC(=O)c2c1c(=O)[nH]c1ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]):[c:8](=[O;D1;H0:9]):[#7;a:10]:[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[O;H0;D2;+0:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:3]-1:[c:8](=[O;D1;H0:9]):[#7;a:10]:[c:11] | null | [] | null | null | null | null | A mixture of 2(1H)-Oxo-quinoline-3,4-dicarboxylic acid (2 g), phosphorous oxychloride (4 g) and dry chloroform (30 mL) was heated at reflux for 2 h. The solvent and excess reagents are removed in vacuo and the residue was treated with ice water to afford Furo[3,4-c]quinoline-1,3,4(5H)-trione as a yellow solid.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Anhydride | null | C1OCc2c1cnc1ccccc21 | C1OCc2c1cnc1ccccc21 | HO- | C(Cl)(Cl)Cl | null | null | O=C(O)c1c(C(=O)O)c2ccccc2[nH]c1=O>C(Cl)(Cl)Cl>O=C1OC(=O)c2c1c(=O)[nH]c1ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-72ad1c3127de403cb4e6f9720380d252 | O=C(O)c1c(C(=O)O)c2ccccc2[nH]c1=O.O=P(Cl)(Cl)Cl>>O=C1OC(=O)c2c1c(Cl)nc1ccccc21 | C1=CC=C2C(=C1)C(=C(C(=O)N2)C(=O)O)C(=O)O.P(=O)(Cl)(Cl)Cl>>ClC1=NC=2C=CC=CC2C2=C1C(OC2=O)=O | O=[c:8]1[c:7]([C:2](O)=[O:1])[c:6]([C:4]([OH:3])=[O:5])[c:16]2[c:11]([nH:10]1)[cH:12][cH:13][cH:14][cH:15]2.O=P(Cl)(Cl)[Cl:9]>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[c:6]2[c:7]1[c:8]([Cl:9])[n:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]21 | O=C(O)c1c(C(=O)O)c2ccccc2[nH]c1=O.O=P(Cl)(Cl)Cl | O=C1OC(=O)c2c1c(Cl)nc1ccccc21 | null | CN(C=O)C | null | Functional Group Interconversion | OtherReaction | 88449996f48b41a26490a7b6400ea4cd93f48a4a70a9ba60fa3fe361b57838d0 | 91508a976437801004dea57b9103e0e1dbcc60fe3226a24e002cc00e886fc498 | O=C1OC(=O)c2c1cnc1ccccc21 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5](-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:9]:[c:10](:[c:11]):[nH;D2;+0:12]:[c;H0;D3;+0:13]:1=O>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:13]1:[n;H0;D2;+0:12]:[c:10](:[c:11]):[c:9]:[c:5]2:[c:4]:1-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:8]-[C:6]-2=[O;D1;H0:7] | null | [] | null | null | 20 | MINUTE | A mixture of 2(1H)-Oxo-quinoline-3,4-dicarboxylic acid (2.0 g), phosphorous oxychloride (10 mL) and 8 drops of dimethyl formamide was refluxed with stirring for 20 min. The reaction mixture was concentrated in vacuo and the residue treated with ice water to afford 4-Chloro-furo[3,4-c]quinoline-1,3-dione as a tan solid.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Aromatic halide.Anhydride | c1cnc2ccccc2c1 | c1ccc2c3c(cnc2c1)COC3 | c1ccc2c3c(cnc2c1)COC3 | HCl | CN(C=O)C | null | 0.333333 | O=C(O)c1c(C(=O)O)c2ccccc2[nH]c1=O.O=P(Cl)(Cl)Cl>CN(C=O)C>O=C1OC(=O)c2c1c(Cl)nc1ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fdab9219ef3743deb64f5cb01f5301ba | O=C1OC(=O)c2c1c(Cl)nc1ccccc21>>O=C1OCc2c(Cl)nc3ccccc3c21.O=C1OCc2c1c(Cl)nc1ccccc21 | ClC1=NC=2C=CC=CC2C2=C1C(OC2=O)=O.[BH4-].[Na+]>>ClC1=NC=2C=CC=CC2C2=C1C(OC2)=O.ClC1=NC=2C=CC=CC2C2=C1COC2=O | [O:1]=[C:2]1[c:5]2[c:6]([Cl:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[C:19](=[O:3])[O:18]1>>[O:1]=[C:2]1[O:3][CH2:4][c:5]2[c:6]([Cl:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]21.[O:16]=[C:17]1[O:18][CH2:19][c:20]2[c:21]1[c:22]([Cl:23])[n:24][c:25]1[cH:26][cH:27][cH:28][cH:29][c:30]21 | O=C1OC(=O)c2c1c(Cl)nc1ccccc21 | O=C1OCc2c(Cl)nc3ccccc3c21.O=C1OCc2c1c(Cl)nc1ccccc21 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | a7d1bfb9ea6cea91c9519d869eed6cdf91b521b515ac8424e33152ff2a869fc9 | 5cea72f7edffe4fa1e3abc99f60e28cb4f6e73c6ce293be0fda0942048f6b571 | O=C1OCc2c1cnc1ccccc21.O=C1OCc2cnc3ccccc3c21 | [Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]2:[c;H0;D3;+0:9]:1-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[C;H0;D3;+0:13]-2=[O;H0;D1;+0:14]>>[Cl;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]2:[c;H0;D3;+0:9]:1-[C:15]-[O;H0;D2;+0:14]-[C;H0;D3;+0:10]-2=[O;D1;H0:11].[O;D... | null | [] | null | null | 2 | HOUR | To a well stirred mixture of 4-Chloro-furo[3,4-c]quinoline-1,3-dione (1.9 g) in tetrahydrofuran (10 mL) was added sodium borohydride (400 mg) at 0° C. and stirring was continued for 2 h. The reaction was then quenched with excess 6N HCl and water, and concentrated in vacuo to afford 4-Chloro-furo[3,4-c]quinolin-3(1H)-o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester | Aromatic halide.Ester.Ester | c1ccc2c3c(cnc2c1)COC3 | c1ccc2c3c(cnc2c1)COC3.c1ccc2c3c(cnc2c1)COC3 | c1ccc2c3c(cnc2c1)COC3.c1ccc2c3c(cnc2c1)COC3 | Other | O1CCCC1 | null | 2 | O=C1OC(=O)c2c1c(Cl)nc1ccccc21>O1CCCC1>O=C1OCc2c(Cl)nc3ccccc3c21.O=C1OCc2c1c(Cl)nc1ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3249a8af79024c0b8ff06a1dbe382196 | O=C1OCc2c1c(Cl)nc1ccccc21>>O=C1OCc2c1cnc1ccccc21 | ClC1=NC=2C=CC=CC2C2=C1C(OC2)=O.C(C)(=O)[O-].[Na+]>>C1OC(C=2C=NC=3C=CC=CC3C21)=O | Cl[c:7]1[c:6]2[c:5]([c:14]3[c:9]([n:8]1)[cH:10][cH:11][cH:12][cH:13]3)[CH2:4][O:3][C:2]2=[O:1]>>[O:1]=[C:2]1[O:3][CH2:4][c:5]2[c:6]1[cH:7][n:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]21 | O=C1OCc2c1c(Cl)nc1ccccc21 | O=C1OCc2c1cnc1ccccc21 | null | [Pd] | C(C)(=O)O | Functional Group Interconversion | Aromatic dehalogenation | 53dec7db27b62b5fafa395ddb5937d72a017015f1fcefa0c49887934c6f14472 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C1OCc2c1cnc1ccccc21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]1:[c:5]-[C:6]-[#8:7]-[C:8]-1=[O;D1;H0:9]>>[O;D1;H0:9]=[C:8]1-[#8:7]-[C:6]-[c:5]:[c:4]-1:[cH;D2;+0:1]:[#7;a:2]:[c:3] | null | [] | null | null | 2 | HOUR | A mixture of 4-Chloro-furo[3,4-c]quinolin-3(1H)-one (500 mg), 10% Palladium on carbon (100 mg) and sodium acetate (500 mg) in 20 mL of acetic acid was hydrogenated at atmospheric pressure for 2 h. After filtration through celite, the solvent was removed in vacuo, and the residue was taken up in methylene chloride. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c3c(cnc2c1)COC3 | c1ccc2c3c(cnc2c1)COC3 | c1ccc2c3c(cnc2c1)COC3 | Other | [Pd].C(C)(=O)O | null | 2 | O=C1OCc2c1c(Cl)nc1ccccc21>[Pd].C(C)(=O)O>O=C1OCc2c1cnc1ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-273c5eb135a04e95a9a37fa897521272 | Nc1ccccc1.O=C1OCc2c1cnc1ccccc21>>O=C1c2cnc3ccccc3c2CN1c1ccccc1 | C1OC(C=2C=NC=3C=CC=CC3C21)=O.NC1=CC=CC=C1>>C1(=CC=CC=C1)N1C(C=2C=NC=3C=CC=CC3C2C1)=O | [NH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.O1[C:2](=[O:1])[c:3]2[cH:4][n:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[c:12]2[CH2:13]1>>[O:1]=[C:2]1[c:3]2[cH:4][n:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[c:12]2[CH2:13][N:14]1[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | Nc1ccccc1.O=C1OCc2c1cnc1ccccc21 | O=C1c2cnc3ccccc3c2CN1c1ccccc1 | null | null | CCCCCC | Acylation | OtherReaction | 71180cd65f60a07d8655a227fcf71b0eeb0e4fa552b6e708f78f901daefc935e | ab33057bb8fb2c9dad5b018a4f87637d8c1c3babde576dc33e825e140481b8d2 | O=C1c2cnc3ccccc3c2CN1c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D3;+0:6]1-O-[CH2;D2;+0:7]-[c:8]2:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:2-1>>[O;D1;H0:5]=[C;H0;D3;+0:6]1-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[CH2;D2;+0:7]-[c:8]2:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:2-1 | null | [] | null | null | null | null | A mixture Furo[3,4-c]quinolin-3(1H)-one (100 mg) and aniline (2 mL) was heated at 180° C. for 5 min. After cooling to room temperature the mixture was slowly diluted with hexane and the resulting product was collected and washed with hexane to afford 2-Phenyl-pyrrolo[3,4-c]quinolin-3(1H)-one.
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Tertiary amide | c1ccc2c3c(cnc2c1)COC3 | c1ccc2c3c(cnc2c1)C[NH]C3 | c1ccc2c3c(cnc2c1)C[NH]C3.c1ccccc1 | HO- | CCCCCC | null | null | Nc1ccccc1.O=C1OCc2c1cnc1ccccc21>CCCCCC>O=C1c2cnc3ccccc3c2CN1c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-85ced26261244ccdada566c55d307030 | O=C(OO)c1cccc(Cl)c1.O=C1c2cnc3ccccc3c2CN1c1ccccc1>>O=C1c2c(c3ccccc3[nH]c2=O)CN1c1ccccc1 | C1(=CC=CC=C1)N1C(C=2C=NC=3C=CC=CC3C2C1)=O.ClC1=CC(=CC=C1)C(=O)OO>>C1(=CC=CC=C1)N1C(C=2C(NC=3C=CC=CC3C2C1)=O)=O | O=C(O[OH:13])c1cccc(Cl)c1.[O:1]=[C:2]1[c:3]2[c:4]([c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[n:11][cH:12]2)[CH2:14][N:15]1[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]1[c:3]2[c:4]([c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[nH:11][c:12]2=[O:13])[CH2:14][N:15]1[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | O=C(OO)c1cccc(Cl)c1.O=C1c2cnc3ccccc3c2CN1c1ccccc1 | O=C1c2c(c3ccccc3[nH]c2=O)CN1c1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 208fbd7481ea3db38e97849b66ab914150e3b853920943719393ba37740d2426 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | O=C1c2c(c3ccccc3[nH]c2=O)CN1c1ccccc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[O;D1;H0:2]=[C:3]1-[#7:4](-[c:5])-[C:6]-[c:7]2:[c:8]:[c:9](:[c:10]):[n;H0;D2;+0:11]:[cH;D2;+0:12]:[c:13]:2-1>>[O;D1;H0:2]=[C:3]1-[#7:4](-[c:5])-[C:6]-[c:7]2:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:[c;H0;D3;+0:12](=[O;H0;D1;+0:1]):[c:13]:2-1 | null | [] | 50 | CELSIUS | 24 | HOUR | A mixture of 2-Phenyl-pyrrolo[3,4-c]quinolin-3(1H)-one (60 mg), and m-chloroperbenzoic acid (105 mg) in 3 mL of methylene chloride was kept at room temperature for 24 h. The mixture was diluted with methylene chloride and washed with sodium carbonate solution. The organic layer was dried over magnesium sulfate and the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccccc1.c1ccc2c3c(cnc2c1)C[NH]C3 | C1NCc2c1cnc1ccccc21 | C1NCc2c1cnc1ccccc21.c1ccccc1 | HCl | C(Cl)Cl | 50 | 24 | O=C(OO)c1cccc(Cl)c1.O=C1c2cnc3ccccc3c2CN1c1ccccc1>C(Cl)Cl>O=C1c2c(c3ccccc3[nH]c2=O)CN1c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bff13585dd6045868860fbe58d6d87e2 | C=O.CC1(C)OC(=O)CC(=O)O1.c1ccncc1>>CC1(C)OC(=O)C(C[n+]2ccccc2)=C(O)O1.[OH-] | CC1(OC(=O)CC(=O)O1)C.N1=CC=CC=C1.C=O>>[OH-].OC1=C(C(OC(O1)(C)C)=O)C[N+]1=CC=CC=C1 | [CH2:8]=[O:18].[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C:15](=[O:16])[O:17]1.[n:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[C:7]([CH2:8][n+:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)=[C:15]([OH:16])[O:17]1.[OH-:18] | C=O.CC1(C)OC(=O)CC(=O)O1.c1ccncc1 | CC1(C)OC(=O)C(C[n+]2ccccc2)=C(O)O1.[OH-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 46efea35d93f5283d05aaf0b002fc1811445bc3deb29e1ea43f74a2419383191 | 2b876f2a10baccbae056058d76912619de176012ba4b118b915592ac5ebf1bc3 | O=C1OCOC=C1C[n+]1ccccc1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[C:4]1-[#8:5]-[C:6]-[#8:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[CH2;D2;+0:10]-1.[c:11]:[c:12]:[n;H0;D2;+0:13]:[c:14]:[c:15]>>[O;D1;H0:3]=[C:4]1-[#8:5]-[C:6]-[#8:7]-[C;H0;D3;+0:8](-[OH;D1;+0:9])=[C;H0;D3;+0:10]-1-[CH2;D2;+0:1]-[n+;H0;D3:13](:[c:12]:[c:11]):[c:14]:[c:15].[OH-;D0:2] | 91.6 | [{"value": 91.6, "product": "[OH-].OC1=C(C(OC(O1)(C)C)=O)C[N+]1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Meldrum's acid (20 g, 0.139 mol) was dissolved in 50 ml of pyridine. The solution immediately turned yellow and was somewhat exothermic. After dissolution was complete, a 37% aqueous solution of formaldehyde (10.4 ml, 0.139 mol) was added in one portion. The reaction mixture was allowed to stir for one hour under argon... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ester.Ester | Ester.Ether.Enol | C1COCOC1.c1ccncc1 | C1=COCOC1.C1=CC=[NH+]C=C1 | C1=COCOC1.C1=CC=[NH+]C=C1 | null | null | null | 1 | C=O.CC1(C)OC(=O)CC(=O)O1.c1ccncc1>>CC1(C)OC(=O)C(C[n+]2ccccc2)=C(O)O1.[OH-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e195c176d6b849b682dd3bfd3a2e2e17 | O=[N+]([O-])c1ccc2nc(S)sc2c1>>Nc1ccc2nc(S)sc2c1 | S.[Na].[N+](=O)([O-])C1=CC2=C(N=C(S2)S)C=C1>>NC1=CC2=C(N=C(S2)S)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([SH:8])[s:9][c:10]2[cH:11]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([SH:8])[s:9][c:10]2[cH:11]1 | O=[N+]([O-])c1ccc2nc(S)sc2c1 | Nc1ccc2nc(S)sc2c1 | null | null | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2scnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | 20 | CELSIUS | 4 | HOUR | 132 Parts of sodium hydrogen sulphide was dissolved in 400 parts of water, and stirred at 20° C. 53 Parts of 6-nitro-2-mercaptobenzothiazole, prepared as described previously herein, was added over 10 minutes; the reaction mixture was then heated to 110° C., and stirred whilst boiling the mixture under reflux condition... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2scnc2c1 | Other | O | 20 | 4 | O=[N+]([O-])c1ccc2nc(S)sc2c1>O>Nc1ccc2nc(S)sc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8d7febe7112045ef956a7488caf062d7 | CCCCCC=CCC=CCCCCCCCC(=O)Cl>>CCCCCCCCC=CCCCCCCCC(=O)Cl | C(CCCCCCCC=CCC=CCCCCC)(=O)Cl.C(CCCCCCCC=CCCCCCCCC)(=O)O>>C(CCCCCCCC=CCCCCCCCC)(=O)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[Cl:20] | CCCCCC=CCC=CCCCCCCCC(=O)Cl | CCCCCCCCC=CCCCCCCCC(=O)Cl | null | null | null | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | null | [C:1]-[C:2]=[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-[C:7]-[C:8]>>[C:1]-[C:2]=[C:3]-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7]-[C:8] | 85 | [{"value": 85.0, "product": "C(CCCCCCCC=CCCCCCCCC)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Octadec-9-enoyl chloride (25.5 parts, boiling point 160°-180° C. at 0.12 Torr, 85% yield) was prepared from 28.1 parts of octadec-9-enoic acid using the procedure described in part A of Example 3 for the preparation of octadec-9,12-dienoyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | CCCCCC=CCC=CCCCCCCCC(=O)Cl>>CCCCCCCCC=CCCCCCCCC(=O)Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e42ee508cabb475f98ffdb624b16f4b6 | NS(=O)(=O)c1ccccc1.c1ccncc1.c1ccncc1>>O=S1N=C(S(=O)(=O)c2ccccc2)c2ccccc21 | C1(=CC=CC=C1)S(=O)(=O)N.N1=CC=CC=C1.N1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl.Cl>>C1(=CC=CC=C1)S(=O)(=O)C1=NS(C2=C1C=CC=C2)=O | [O:1]=[S:2]([NH2:3])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.c1c[cH:4][cH:14][cH:19]n1.c1n[cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[S:2]1[N:3]=[C:4]([S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | NS(=O)(=O)c1ccccc1.c1ccncc1.c1ccncc1 | O=S1N=C(S(=O)(=O)c2ccccc2)c2ccccc21 | null | null | C(C)(=O)O.CO | Functional Group Interconversion | OtherReaction | eda97579b08027eca375e0a357e16f3fb2bb4c16016c7597519e65665f0d76d1 | 3e2c31b10cef57bda3459f8766fa5304a52d531571e8ab0c8709da1016e8804b | O=S1N=C(S(=O)(=O)c2ccccc2)c2ccccc21 | [NH2;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[cH;D2;+0:10]1:[cH;D2;+0:11]:n:c:c:[cH;D2;+0:12]:1.[c:13]1:[c:14]:[cH;D2;+0:15]:c:n:[cH;D2;+0:16]:1>>[O;D1;H0:3]=[S;H0;D3;+0:2]1-[N;H0;D2;+0:1]=[C;H0;D3;+0:12](-[#16:17](=[O;D1;H0:18])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:5](:[... | null | [] | null | null | 45 | MINUTE | 31.44 G. (0.2 mole) of benzenesulfonamide was dissolved in 80 ml. of dry pyridine to obtain a clear, straw-colored solution, which was placed in a cold water bath. To this pyridine solution was added the carbon tetrachloride solution produced in Part B above. An exothermic reaction ensued with formation of a white slur... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfone | c1ccccc1.c1ccncc1.c1ccncc1 | c1ccccc1.c1ccc2sncc2c1 | c1ccccc1.c1ccc2sncc2c1 | Other | C(C)(=O)O.CO | null | 0.75 | NS(=O)(=O)c1ccccc1.c1ccncc1.c1ccncc1>C(C)(=O)O.CO>O=S1N=C(S(=O)(=O)c2ccccc2)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-832f1035ccee4e16b54fec29013e82eb | CCOC(=O)C1CCN(C(=O)C2CC2)CC1>>O=C(C1CC1)N1CCC(CO)CC1 | [BH4-].[Li+].C1(CC1)C(=O)N1CCC(CC1)C(=O)OCC.B(OC)(OC)OC>>C1(CC1)C(=O)N1CCC(CC1)CO | CCO[C:10]([CH:9]1[CH2:8][CH2:7][N:6]([C:2](=[O:1])[CH:3]2[CH2:4][CH2:5]2)[CH2:13][CH2:12]1)=[O:11]>>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5]1)[N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][OH:11])[CH2:12][CH2:13]1 | CCOC(=O)C1CCN(C(=O)C2CC2)CC1 | O=C(C1CC1)N1CCC(CO)CC1 | null | null | O.O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(C1CC1)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | 63.7 | [{"value": 63.7, "product": "C1(CC1)C(=O)N1CCC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A solution of 1-(cyclopropylcarbonyl)-4-carboethoxy piperidine (35 g, 156 mmol) in anhydrous tetrahydrofuran (350 mL) was stirred at ambient temperature under a nitrogen atmosphere. A solution of lithium borohydride in tetrahydrofuran (2M, 78 mL, 156 mmol) was added dropwise. Trimethyl borate (1.77 mL, 15.7 mmol) was a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC1.C1CC[NH]CC1 | HO- | O.O1CCCC1 | null | 48 | CCOC(=O)C1CCN(C(=O)C2CC2)CC1>O.O1CCCC1>O=C(C1CC1)N1CCC(CO)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4a3dc28a00854038bc8f00c5c9d2d330 | O=C(CC1CCN(CC2CC2)CC1)c1ccc(F)cc1.[Br][Mg][c]1ccccc1>>OC(CC1CCN(CC2CC2)CC1)(c1ccccc1)c1ccc(F)cc1 | [NH4+].[Cl-].C1(=CC=CC=C1)[Mg]Br.CCOCC.C1(CC1)CN1CCC(CC1)CC(=O)C1=CC=C(C=C1)F>>C1(CC1)CN1CCC(CC1)CC(O)(C1=CC=CC=C1)C1=CC=C(C=C1)F | [O:1]=[C:2]([CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][CH2:11]2)[CH2:12][CH2:13]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1.[Br][Mg][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[OH:1][C:2]([CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][CH2:11]2)[CH2:12][CH2:13]1)([c:14]1[cH:15][cH:16][c... | O=C(CC1CCN(CC2CC2)CC1)c1ccc(F)cc1.[Br][Mg][c]1ccccc1 | OC(CC1CCN(CC2CC2)CC1)(c1ccccc1)c1ccc(F)cc1 | null | null | O1CCCC1 | C-C Coupling | Grignard from ketone to alcohol | 181fdd58eba73242b2de454099edbf422e18f2a0a3f78d67208494cf1d83905c | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | c1ccc(C(CC2CCN(CC3CC3)CC2)c2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7]-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[c:10](:[c:11]):[c:12])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 1-(Cyclopropylmethyl)-4-(2'-(4"-fluorophenyl)-2'-oxoethyl)piperidine (Example 429, 1.0 g, 3.6 mmol) was mixed with dry tetrahydrofuran (10 mL). A solution of phenyl magnesium bromide in ether (3.0M, 3 mL, 9 mmol) was added with stirring. The reaction mixture was stirred for 24 h; poured onto a saturated NH4Cl solution ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | c1ccccc1 | c1ccccc1 | C1CC[NH]CC1.C1CC1.c1ccccc1.c1ccccc1 | Br-.Mg | O1CCCC1 | null | null | O=C(CC1CCN(CC2CC2)CC1)c1ccc(F)cc1.[Br][Mg][c]1ccccc1>O1CCCC1>OC(CC1CCN(CC2CC2)CC1)(c1ccccc1)c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a1afae4c809643d59843e94bfd9a4e3d | Fc1cc[c]([Mg][Br])cc1.Fc1ccc(OCC2CCN(CC3CC3)CC2)cc1>>OC(CC1CCN(CC2CC2)CC1)(c1ccc(F)cc1)c1ccc(F)cc1 | C1(CC1)CN1CCC(CC1)COC1=CC=C(C=C1)F.FC1=CC=C(C=C1)[Mg]Br.O1CCCC1>>C1(CC1)CN1CCC(CC1)CC(O)(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F | [Br][Mg][c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[O:1]([c:2]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][CH2:11]2)[CH2:12][CH2:13]1>>[OH:1][C:2]([CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][CH2:11]2)[CH2:12][CH2:13]1)([c:14]1[cH:15][cH:16][c... | Fc1cc[c]([Mg][Br])cc1.Fc1ccc(OCC2CCN(CC3CC3)CC2)cc1 | OC(CC1CCN(CC2CC2)CC1)(c1ccc(F)cc1)c1ccc(F)cc1 | null | null | null | C-C Coupling | OtherReaction | a75c9d378418ce52c555e34277b111f09bd2b02a0be0a5d1bbdee04e0640cc07 | 25f603babd45839717eb7b0e561ce156c6a60169be5fa25d8aaf6c4c8ba84b37 | c1ccc(C(CC2CCN(CC3CC3)CC2)c2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1)-[C:16]>>[C:6]-[C:7](-[CH2;D2;+0:8]-[C;H0;D4;+0:10](-[OH;D1;+0:9])(-[c:17]1:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c... | null | [] | null | null | null | null | Following the procedure described for Example 547, the compound of Example 429 (1.0 g, 3.6 mmol) was reacted a solution of 4-fluorophenylmagnesium bromide in tetrahydrofuran (1.0M, 9 mL, 9 mmol) to give the title compound, a solid (1.1 g): mp 119°-121° C.; Anal.: Calcd for C23H27F2NO.0.5H2O: C, 72.60, H, 7.41, N, 3.68,... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ether | Tertiary alcohol | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CC[NH]CC1.C1CC1.c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | Fc1cc[c]([Mg][Br])cc1.Fc1ccc(OCC2CCN(CC3CC3)CC2)cc1>>OC(CC1CCN(CC2CC2)CC1)(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4a783f44e5724f2c918ab22504b47e95 | CCOC(=O)c1ccc(Br)cc1.Fc1ccc(Br)cc1>>CCOC(=O)c1ccc(-c2ccc(F)cc2)cc1 | BrC1=CC=C(C=C1)F.BrC1=CC=C(C(=O)OCC)C=C1>>C(C)OC(C1=CC=C(C=C1)C1=CC=C(C=C1)F)=O | Br[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:18][cH:17]1.Br[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | CCOC(=O)c1ccc(Br)cc1.Fc1ccc(Br)cc1 | CCOC(=O)c1ccc(-c2ccc(F)cc2)cc1 | null | null | null | C-C Coupling | Negishi | c762f793fad28f910ecef7baabecb58fd3905901ac0af2c73542eba7e0faa33e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | null | [] | null | null | null | null | Using the procedure described for Example 551, 4-bromofluorobenzene (1.75 g, 10 mmol) was metallated and coupled with ethyl 4-bromobenzoate (2.28 g, 10 mmol) to give the title compound after chromatography (ethyl acetate-hexanes (1:9) (0.7 g)): 1H-NMR (CDCl3, 300 MHz): 8.1 (d, 2H, J=8), 7.65-7.5 (m, 4H), 7.15 (t, 2H, J... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | null | null | null | CCOC(=O)c1ccc(Br)cc1.Fc1ccc(Br)cc1>>CCOC(=O)c1ccc(-c2ccc(F)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-29553a4becdf4d34adb98b5354444849 | CC(C)(C)[C@@]1(O)CCN2C[C@@H]3c4ccccc4CCc4cccc(c43)[C@H]2C1.NC(CO)(CO)CO.O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1>>NCCc1ccc(O)c(O)c1 | C1CN(CCC12C(=O)NCN2C3=CC=CC=C3)CCCC(=O)C4=CC=C(C=C4)F.CC(C)(C)[C@]1(CCN2C[C@@H]3C=4C=CC=CC4CCC5=C3C(=CC=C5)[C@H]2C1)O.C(C(CO)(CO)N)O.Cl.[Na+].[Cl-].[Mg+2].[Cl-].[Cl-]>>NCCC1=CC(O)=C(O)C=C1 | CC(C)(C)[C@@]1([OH:8])CCN2C[C@@H]3c4ccccc4CCc4cccc(c43)[C@H]2C1.OCC(CO)(C[OH:10])[NH2:1].O=C1NCN(c2ccccc2)C12CCN(C[CH2:2]C[C:3](=O)[c:4]1[cH:5][cH:6][c:7](F)[cH:9][cH:11]1)CC2>>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([OH:10])[cH:11]1 | CC(C)(C)[C@@]1(O)CCN2C[C@@H]3c4ccccc4CCc4cccc(c43)[C@H]2C1.NC(CO)(CO)CO.O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1 | NCCc1ccc(O)c(O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 955cea429a112d006f45729daa4c51fb4b3bbd7e792f3382a8f0f119928ce8dd | 509e1d9aee36ecf6808e5844cd4b578cf1f67efac6379dd129f5b1e3ddd51fb2 | c1ccccc1 | C-C(-C)(-C)-[C@@]1(-[OH;D1;+0:1])-C-C-N2-C-[C@H]3-c4:c:c:c:c:c:4-C-C-c4:c:c:c:c(:c:4-3)-[C@@H]-2-C-1.F-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5](-[C;H0;D3;+0:6](=O)-C-[CH2;D2;+0:7]-C-N2-C-C-C3(-C-C-2)-C(=O)-N-C-N-3-c2:c:c:c:c:c:2):[c:8]:[cH;D2;+0:9]:1.O-C-C(-[NH2;D1;+0:10])(-C-O)-C-[OH;D1;+0:11]>>[NH2;D1;+0:10]-[CH2;D2;+0:7]-[... | null | [] | null | null | 15 | MINUTE | 0.5 mL aliquots of the membrane preparation were incubated with unlabeled drugs, and 0.15 nM [3H]spiperone in a final volume of 1 mL containing 50 mM Tris HCl, 120 mM NaCl and 1 mM MgCl2 (pH 7.7). Nonspecific binding was measured in the presence of 100 nM (+)-butaclamol. After 15 minutes of incubation at 37° C., sample... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Secondary amide.Primary alcohol.Primary alcohol.Primary alcohol.Tertiary alcohol.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine | Aromatic alcohol.Aromatic alcohol.Primary amine | c1ccc2c(c1)CCc1cccc3c1[C@@H]2CN1CCCC[C@H]31.c1ccccc1.C1CC2(CCN1)CNCN2.c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | null | null | 0.25 | CC(C)(C)[C@@]1(O)CCN2C[C@@H]3c4ccccc4CCc4cccc(c43)[C@H]2C1.NC(CO)(CO)CO.O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1>>NCCc1ccc(O)c(O)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9334216d98874a0aa0f332578a5d0309 | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)O)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O.[N-]=[N+]=C(c1ccccc1)c1ccccc1>>CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O | C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1.NC1=C(N=CN1[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O)C(=O)O>>C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1N)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O | [CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]([C:13](=[O:14])[OH:15])[c:29]2[NH2:30])[C@H:31]([O:32][C:33]([CH3:34])=[O:35])[C@@H:36]1[O:37][C:38]([CH3:39])=[O:40].[N-]=[N+]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][C:2](=[O... | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)O)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O.[N-]=[N+]=C(c1ccccc1)c1ccccc1 | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 8531b6eb3abfd6846ce0cb8d79abac610072134e0cc0be40cc269196cd4eea5b | d6eab3abd961fdb019332f17e55277b8a7c7f7a1f79c71be7a6248f0a0e6a15e | O=C(OC(c1ccccc1)c1ccccc1)c1cn([C@H]2CCCO2)cn1 | [#7;a:1]:[c:2](-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]):[c:6]:[#7;a:7].[N-]=[N+]=[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]>>[#7;a:1]:[c:2](-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:6]:[#7;a:7] | 88 | [{"value": 88.0, "product": "C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1N)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Diphenyldiazomethane (2.0 g, 10.3 mmol) was added to the suspension of 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid (3.86 g, 10 mmol) in CH2Cl2 (50 mL). The mixture was stirred at room temperature for 16 h, by which time all the reactants had dissolved. The reaction mixture was poure... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo | Ester | null | null | C1CCOC1.c1c[nH]cn1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 16 | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)O)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O.[N-]=[N+]=C(c1ccccc1)c1ccccc1>C(Cl)Cl>CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-36b73a24973348ec866f55e0fe8d820d | O=C(Nc1nc2c(c(=O)o1)NCN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)OCc1ccccc1>>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)o1 | C1(=CC=CC=C1)COC(=O)NC=1OC(C2=C(N1)N(CN2)[C@H]2[C@H](O)[C@H](O)[C@H](O2)CO)=O>>C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(OC2=O)N | O=C(OCc1ccccc1)[NH:1][c:2]1[n:3][c:4]2[c:5]([c:18](=[O:19])[o:20]1)[NH:6][CH2:7][N:8]2[C@@H:9]1[O:10][C@H:11]([CH2:12][OH:13])[C@@H:14]([OH:15])[C@H:16]1[OH:17]>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@@H:9]2[O:10][C@H:11]([CH2:12][OH:13])[C@@H:14]([OH:15])[C@H:16]2[OH:17])[c:18](=[O:19])[o:20]1 | O=C(Nc1nc2c(c(=O)o1)NCN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)OCc1ccccc1 | Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)o1 | null | [Pd] | CN(C)C=O | Functional Group Interconversion | OtherReaction | fc2498df57d0b68601c8b0128483aec1185030e8f2a21873dd28fb10e9c48464 | 2035eb5d20d0a6c1999bd2ad7c2c4c43934ccc29852a60019e95d400e45d9192 | O=c1ocnc2c1ncn2[C@H]1CCCO1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]2:[c:5](:[c:6](=[O;D1;H0:7]):[#8;a:8]:1)-[NH;D2;+0:9]-[CH2;D2;+0:10]-[N;H0;D3;+0:11]-2-[C:12](-[C:13])-[#8:14]-[C:15]>>[C:15]-[#8:14]-[C:12](-[n;H0;D3;+0:11]1:[cH;D2;+0:10]:[n;H0;D2;+0:9]:[c:5]2:[c:6](=[O;D1;H0:7]):[#8;a:8]:[c:2](-[NH2;D1;+0:1]):[#7;a:3]:[c:4]:... | null | [] | null | null | 4 | HOUR | 10% Palladium on charcoal (172 mg) was added to a solution of 5-[[(phenylmethoxy)carbonyl]amino]-3-(β-D-ribofuranosyl)imidazo[4,5-d][1,3]oxazin-7(1H)-one (172 mg, 0.41 mmol) in DMF (7 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 4 h. The mixture was filtered through prewashed Celi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amine.Tertiary amine | Primary amine | c1ccccc1.c1nc2c(co1)NCN2 | c1nc2cocnc2n1 | c1nc2cocnc2n1.C1CCOC1 | HO- | [Pd].CN(C)C=O | null | 4 | O=C(Nc1nc2c(c(=O)o1)NCN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)OCc1ccccc1>[Pd].CN(C)C=O>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)o1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ff74fda1878941da9ad64d6ce412d08d | O=C(NC(=O)OCc1ccccc1)Nc1c(C(=O)OC(c2ccccc2)c2ccccc2)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>NC(=O)Nc1c(C(=O)O)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1NC(=O)NC(=O)OCC1=CC=CC=C1)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO>>NC(=O)NC1=C(N=CN1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C(=O)O | O=C(OCc1ccccc1)[NH:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([C:7](=[O:8])[O:9]C(c2ccccc2)c2ccccc2)[n:10][cH:11][n:12]1[C@@H:13]1[O:14][C@H:15]([CH2:16][OH:17])[C@@H:18]([OH:19])[C@H:20]1[OH:21]>>[NH2:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([C:7](=[O:8])[OH:9])[n:10][cH:11][n:12]1[C@@H:13]1[O:14][C@H:15]([CH2:16][OH:17])[C@@H:18]([OH:... | O=C(NC(=O)OCc1ccccc1)Nc1c(C(=O)OC(c2ccccc2)c2ccccc2)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | NC(=O)Nc1c(C(=O)O)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | null | [Pd] | CN(C)C=O.C1CCOC1.C(C)O | Reduction | OtherReaction | 6e1486eafbcea8442192eba866515d318abd7924f55a61ba62dacae9c5b4ae62 | ff61d05c19231ae2eed2fc2d917cf58f7517ebb4b75f8fcb793d18e13a839cdf | c1cn([C@H]2CCCO2)cn1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5](:[#7;a:6]):[c:7](-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[#7;a:11]>>[#7;a:11]:[c:7](-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]):[c:5](-[#7:4]-[C:2](-[NH2;D1;+0:1])=[O;D1;H0:3]):[#7;a:6] | null | [] | null | null | 2 | HOUR | 5-[[[[(phenylmethoxy)carbonyl]amino]carbonyl]amino]-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester (1.76 g, 2.9 mmol) was dissolved in the mixture of DMF (50 mL), THF (20 mL) and ethanol (30 mL) and mixed with 10% palladium on charcoal. The mixture was hydrogenated at 50 psig pressure for 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Urea | Carboxylic acid.Urea | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1c[nH]cn1.C1CCOC1 | HO- | [Pd].CN(C)C=O.C1CCOC1.C(C)O | null | 2 | O=C(NC(=O)OCc1ccccc1)Nc1c(C(=O)OC(c2ccccc2)c2ccccc2)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>[Pd].CN(C)C=O.C1CCOC1.C(C)O>NC(=O)Nc1c(C(=O)O)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b09968f7a78948329b0580e276d90a67 | NC(=O)Nc1nc(C(=O)O)cn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)o1 | Cl.CN(CCCN=C=NCC)C.NC(=O)NC=1N(C=C(N1)C(=O)O)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO>>C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(OC2=O)N | O[C:18]([c:5]1[cH:4][n:8]([C@@H:9]2[O:10][C@H:11]([CH2:12][OH:13])[C@@H:14]([OH:15])[C@H:16]2[OH:17])[c:7]([NH:3][C:2]([NH2:1])=[O:20])[n:6]1)=[O:19]>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@@H:9]2[O:10][C@H:11]([CH2:12][OH:13])[C@@H:14]([OH:15])[C@H:16]2[OH:17])[c:18](=[O:19])[o:20]1 | NC(=O)Nc1nc(C(=O)O)cn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)o1 | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | cd6bc30d58c0b8a63a359140a705be31656f97d3a88e5b712198a607b7f4cb74 | fadb2580f49ac438d8998fc783c5f4fbb063a52cd630276446cea9d6cf60b2de | O=c1ocnc2c1ncn2[C@H]1CCCO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c;H0;D3;+0:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](-[N;D1;H2:8])=[O;H0;D1;+0:9]):[#7;a:10](-[C:11]-[#8:12]):[cH;D2;+0:13]:1>>[#8:12]-[C:11]-[#7;a:10]1:[cH;D2;+0:5]:[#7;a:4]:[c:3]2:[c;H0;D3;+0:1](=[O;D1;H0:2]):[o;H0;D2;+0:9]:[c;H0;D3;+0:7](-[N;D1;H2:8]):[n;H0;D2;+0:6]:[c;H0;D3;+0:... | null | [] | null | null | 8 | HOUR | 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg, 0.41 mmol) was added to a solution of 5-[[(amino)carbonyl]amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid (19 mg, 0.063 mmol) in water (2 mL) and CH3OH (5 mL) and the mixture was stirred at room temperature overnight. The reaction was quench... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Urea | null | c1c[nH]cn1 | c1nc2cocnc2n1 | c1nc2cocnc2n1.C1CCOC1 | HO- | CO.O | null | 8 | NC(=O)Nc1nc(C(=O)O)cn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>CO.O>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)o1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-099b2ab360d147c7b305025fdc1c5d3f | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O.O=C(N=C=S)OCc1ccccc1>>CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2NC(=S)NC(=O)OCc2ccccc2)[C@H](OC(C)=O)[C@@H]1OC(C)=O | C(C1=CC=CC=C1)OC(=O)N=C=S.C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1N)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.C(C1=CC=CC=C1)OC(=O)N=C=S>>C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1NC(=S)NC(=O)OCC1=CC=CC=C1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O | [CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]([C:13](=[O:14])[O:15][CH:16]([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:29]2[NH2:30])[C@H:44]([O:45][C:46]([CH3:47])=[O:48])[C@@H:49]1[O:50][C:51]([CH3:52])=[O:53].[C:31](=[S:32])=[N:33][C:34]... | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O.O=C(N=C=S)OCc1ccccc1 | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2NC(=S)NC(=O)OCc2ccccc2)[C@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | d196f428325df478b289a71c7a1a97a24db09ae9600571f1068a75b9c1a64923 | d5d2ed8b9b1ac1023c3c8e0c0be1b8fb1cb57874c436f1471dd4bc0b489dd07a | O=C(NC(=S)Nc1c(C(=O)OC(c2ccccc2)c2ccccc2)ncn1[C@H]1CCCO1)OCc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]-[#8:9]):[c:10]:1-[NH2;D1;+0:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[N;H0;D2;+0:16]=[C;H0;D2;+0:17]=[S;D1;H0:18]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]-[#8:9]):[c:10]:1-[NH;D2;+0:11]-[C;H0;D3;+0:17](=[S;D1;H0:18])-[NH;D2;+0:16]... | 98 | [{"value": 98.0, "product": "C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1NC(=S)NC(=O)OCC1=CC=CC=C1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 46 | HOUR | Four portions of benzyloxycarbonyl isothiocyanate (Caution: stench, handle in a well ventilated hood only, crude, 2.0 g each, total 41 mmol) were added to a solution of 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester (1.1 g, 2 mmol) in CH2Cl2 (10 mL) at 0 h, 6 h, 22... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Carbamic ester.Thiourea | null | null | C1CCOC1.c1c[nH]cn1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 46 | CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2N)[C@H](OC(C)=O)[C@@H]1OC(C)=O.O=C(N=C=S)OCc1ccccc1>C(Cl)Cl>CC(=O)OC[C@H]1O[C@@H](n2cnc(C(=O)OC(c3ccccc3)c3ccccc3)c2NC(=S)NC(=O)OCc2ccccc2)[C@H](OC(C)=O)[C@@H]1OC(C)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55af28a305474a509ca9db96966a0640 | O=C(Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)s1)OCc1ccccc1>>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)s1 | C1(=CC=CC=C1)COC(NC=1SC(C2=C(N1)N(C=N2)[C@H]2[C@H](O)[C@H](O)[C@H](O2)CO)=O)=O>>[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(=O)SC(N)=NC12 | O=C(OCc1ccccc1)[NH:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@@H:9]2[O:10][C@H:11]([CH2:12][OH:13])[C@@H:14]([OH:15])[C@H:16]2[OH:17])[c:18](=[O:19])[s:20]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@@H:9]2[O:10][C@H:11]([CH2:12][OH:13])[C@@H:14]([OH:15])[C@H:16]2[OH:17])[c:18](=[O:19])[s:20]1 | O=C(Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)s1)OCc1ccccc1 | Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)s1 | null | [Pd] | CN(C)C=O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=c1scnc2c1ncn2[C@H]1CCCO1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[#7;a:9]:1>>[#7;a:6]:[c:5]1:[c:4]:[#16;a:3]:[c:2](-[NH2;D1;+0:1]):[#7;a:9]:[c:7]:1:[#7;a:8] | null | [] | null | null | 6 | HOUR | A solution of [3,7-dihydro-7-oxo-3-(β-D-ribofuranosyl)imidazo[4,5-d][1,3]thiazin-5-yl]carbamic acid phenylmethyl ester (170 mg, 0.39 mmol) in dry DMF (10 mL) was hydrogenated in the presence of 10% palladium on charcoal (200 mg) at room temperature and 50 psig for 6 h. Additional catalyst (200 mg) was added and hydroge... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1nc2cscnc2n1.C1CCOC1 | HO- | [Pd].CN(C)C=O | null | 6 | O=C(Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)s1)OCc1ccccc1>[Pd].CN(C)C=O>Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1c5d6f3e9f13411cab9d4d7d0306d9c2 | CN(C=O)c1ccccc1.Nc1nccs1>>CN(C=Nc1nccs1)c1ccccc1 | P(=O)(Cl)(Cl)Cl.NC=1SC=CN1.CN(C1=CC=CC=C1)C=O>>S1C(=NC=C1)N=CN(C1=CC=CC=C1)C | O=[CH:3][N:2]([CH3:1])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH2:4][c:5]1[n:6][cH:7][cH:8][s:9]1>>[CH3:1][N:2]([CH:3]=[N:4][c:5]1[n:6][cH:7][cH:8][s:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CN(C=O)c1ccccc1.Nc1nccs1 | CN(C=Nc1nccs1)c1ccccc1 | null | NC=1SC=CN1 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | d548d780574a6e8bf4728bd7c36e74e2f78572af917149e7c38580ae970e40c3 | b9d219f0674c4c56492b0e55f3afda0e6dc263a5614af120d7a27809c687708b | C(=Nc1nccs1)Nc1ccccc1 | O=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[c:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[C;D1;H3:3]-[#7:2](-[c:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 94.2 | [{"value": 94.2, "product": "S1C(=NC=C1)N=CN(C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a stirred suspension of N-methylformanilide (67.6 g; 0.50 mole), toluene (25 g) and 2-aminothiazole (2.0 g; 0.02 mole) was added phosphorus oxychloride (45.8 mL; 0.50 mole) over 15 minutes. The temperature was maintained below 45° C. during this addition. Stirring was continued for 10 minutes, after which time a hot... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | null | null | null | c1cscn1.c1ccccc1 | HO- | NC=1SC=CN1.C1(=CC=CC=C1)C | null | 0.166667 | CN(C=O)c1ccccc1.Nc1nccs1>NC=1SC=CN1.C1(=CC=CC=C1)C>CN(C=Nc1nccs1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-94e0b41df81646abb6a98f85deb9681f | CN(C=O)c1ccccc1.Nc1ccccn1>>CN(C=Nc1ccccn1)c1ccccc1 | CN(C1=CC=CC=C1)C=O.NC1=NC=CC=C1>>N1=C(C=CC=C1)N=CN(C1=CC=CC=C1)C | O=[CH:3][N:2]([CH3:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1>>[CH3:1][N:2]([CH:3]=[N:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CN(C=O)c1ccccc1.Nc1ccccn1 | CN(C=Nc1ccccn1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d548d780574a6e8bf4728bd7c36e74e2f78572af917149e7c38580ae970e40c3 | b9d219f0674c4c56492b0e55f3afda0e6dc263a5614af120d7a27809c687708b | C(=Nc1ccccn1)Nc1ccccc1 | O=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C;D1;H3:3]-[#7:2](-[c:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | Prepared following the procedure of Example 1 from N-methylformanilide and 2-aminopyridine. Vacuum distillation of the crude product gave pure 3 as a pale yellow oil: bp 164°-165° C. @ 0.5 mm Hg. 1H-NMR (CDCl3) 8.94 (S, 1H), 8.30 (d, 1H, J=5 Hz), 7.6-6.9 (m,8H), 3.52 (S, 3H); IR(neat) 3045, 1620, 1580, 1555, 1500, 1460... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | null | null | null | c1ccncc1.c1ccccc1 | HO- | null | null | null | CN(C=O)c1ccccc1.Nc1ccccn1>>CN(C=Nc1ccccn1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-21c43fd9d87e46ca92b874799634794d | CCN(C=O)c1ccccc1.Nc1ccccn1>>CCN(C=Nc1ccccn1)c1ccccc1 | C(C)N(C1=CC=CC=C1)C=O.NC1=NC=CC=C1>>N1=C(C=CC=C1)N=CN(C1=CC=CC=C1)CC | O=[CH:4][N:3]([CH2:2][CH3:1])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1>>[CH3:1][CH2:2][N:3]([CH:4]=[N:5][c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CCN(C=O)c1ccccc1.Nc1ccccn1 | CCN(C=Nc1ccccn1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d548d780574a6e8bf4728bd7c36e74e2f78572af917149e7c38580ae970e40c3 | b9d219f0674c4c56492b0e55f3afda0e6dc263a5614af120d7a27809c687708b | C(=Nc1ccccn1)Nc1ccccc1 | O=[CH;D2;+0:1]-[#7:2](-[C:3])-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C:3]-[#7:2](-[c:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | Prepared following the procedure of Example 1 from N-ethylformanilide and 2-aminopyridine. Vacuum distillation of the crude product gave pure 4 as a pale yellow oil: bp 164° C. @ 0.5 mm Hg. 1H-NMR (CDCl3) 8.83 (S, 1H), 8.30 (m,1H), 7.5-6.9 (m, 8H), 4.09 (q, 2H, J=7 Hz) 1.26 (t, 3H, J=7 Hz); IR(neat) 2990, 1620, 1570, 1... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | null | null | null | c1ccncc1.c1ccccc1 | HO- | null | null | null | CCN(C=O)c1ccccc1.Nc1ccccn1>>CCN(C=Nc1ccccn1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ef6d53c2edb44bcfb521c55fd592d6aa | OC(CCl)C(O)CCl>>ClCC1OCOC1CCl | S(O)(O)(=O)=O.ClCC(C(CCl)O)O.O1OOCCC1.ClCC(C(CCl)O)O>>ClCC1OCOC1CCl | O[CH:7]([CH:3]([CH2:2][Cl:1])[OH:4])[CH2:8][Cl:9]>>[Cl:1][CH2:2][CH:3]1[O:4][CH2:5][O:6][CH:7]1[CH2:8][Cl:9] | OC(CCl)C(O)CCl | ClCC1OCOC1CCl | null | null | ClCCCl | Heteroatom Alkylation and Arylation | Diol acetalization | dffe56556f707e5f943e2e6a5abded5aa25faea622ba5aaefbcc99107066ab83 | 4c2b5746d777df4b3850be8bb940817bfc292176b756747eedaf24277a4ed5e4 | C1COCO1 | O-[CH;D3;+0:1](-[C:2]-[Cl;D1;H0:3])-[C:4](-[C:5])-[OH;D1;+0:6]>>[C:5]-[C:4]1-[O;H0;D2;+0:6]-[C:7]-[#8:8]-[CH;D3;+0:1]-1-[C:2]-[Cl;D1;H0:3] | 89.5 | [{"value": 89.5, "product": "ClCC1OCOC1CCl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A three-neck 500-mL flask equipped with a thermometer, a mechanical stirrer, an addition funnel, a condenser, and a positive nitrogen atmosphere was charged with 1,4-dichloro-2,3-butanediol (50.0 g, 0.314 mole), trioxane (9.43 g, 0.314 mole), and 1,2-dichloroethane (EDC) (300 mL). The 1,4-dichloro-2,3-butanediol was no... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1COCO1 | C1COCO1 | null | ClCCCl | null | 8 | OC(CCl)C(O)CCl>ClCCCl>ClCC1OCOC1CCl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-235b5db98cd94164b1a080341731bb8b | CCOC(=O)NC(CO)C(O)c1ccc(SC)cc1>>CSc1ccc(C2OC(=O)NC2CO)cc1 | OC(C(CO)NC(=O)OCC)C1=CC=C(C=C1)SC>>CSC1=CC=C(C=C1)C1C(NC(O1)=O)CO | CCO[C:9](=[O:10])[NH:11][CH:12]([CH:7]([c:6]1[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:16][cH:15]1)[OH:8])[CH2:13][OH:14]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[O:8][C:9](=[O:10])[NH:11][CH:12]2[CH2:13][OH:14])[cH:15][cH:16]1 | CCOC(=O)NC(CO)C(O)c1ccc(SC)cc1 | CSc1ccc(C2OC(=O)NC2CO)cc1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | Intramolecular transesterification/Lactone formation | 63623eac8f0b8aa138cf2addcfba157dc0d2343ba1e0308780e210c976c64df4 | 9e80c4ff7ba95f533a858930199d9a906feab625690374862e4109792e682b92 | O=C1NCC(c2ccccc2)O1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5](-[OH;D1;+0:6])-[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[#7:3]-[C:4]-[C:5](-[c:7])-[O;H0;D2;+0:6]-1 | null | [] | null | null | null | null | Compound (H) (5 g; 17.5 mmols) has been dissolved in warm toluene (25 ml). To this solution, an equimolar amount of potassium tert. butylate has been added and the reaction mixture has been refluxed for 3 hours. Afterwards, almost all of the solvent has been evaporated; water and ice have been added to the residue and ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary alcohol | Carbamic ester | null | C1COCN1 | c1ccccc1.C1COCN1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)NC(CO)C(O)c1ccc(SC)cc1>C1(=CC=CC=C1)C>CSc1ccc(C2OC(=O)NC2CO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d496dfe999fb47a1b259625feaebd9e5 | ClCCCOc1ccc(Cl)c(Cl)c1.OC1(c2ccc(Cl)c(Cl)c2)CCNCC1>>OC1(c2ccc(Cl)c(Cl)c2)CCN(CCCOc2ccc(Cl)c(Cl)c2)CC1 | ClC=1C=C(OCCCCl)C=CC1Cl.OC1(CCNCC1)C1=CC(=C(C=C1)Cl)Cl>>ClC=1C=C(OCCCN2CCC(CC2)(C2=CC(=C(C=C2)Cl)Cl)O)C=CC1Cl | Cl[CH2:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][c:21]([Cl:22])[c:23]([Cl:24])[cH:25]1.[OH:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]2)[CH2:11][CH2:12][NH:13][CH2:26][CH2:27]1>>[OH:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]2)[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][O:17][... | ClCCCOc1ccc(Cl)c(Cl)c1.OC1(c2ccc(Cl)c(Cl)c2)CCNCC1 | OC1(c2ccc(Cl)c(Cl)c2)CCN(CCCOc2ccc(Cl)c(Cl)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3ccccc3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 97.5 | [{"value": 97.5, "product": "ClC=1C=C(OCCCN2CCC(CC2)(C2=CC(=C(C=C2)Cl)Cl)O)C=CC1Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "ClC=1C=C(OCCCN2CCC(CC2)(C2=CC(=C(C=C2)Cl)Cl)O)C=CC1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3,4-dichlorophenoxy)propylchloride 1.38 g and 4-hydroxy-4-(3,4-dichlorophenyl)piperidine 1.35 g are reacted in the same manner as Example 109 (1) to prepare 2.40 g (Yield: 97.5%) of 1-{3-(3,4-dichlorophenoxy)propyl}-4-hydroxy-4-(3,4-dichlorophenyl) piperidine (III-66). mp. 118.0°-118.5° C.
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HCl | null | null | null | ClCCCOc1ccc(Cl)c(Cl)c1.OC1(c2ccc(Cl)c(Cl)c2)CCNCC1>>OC1(c2ccc(Cl)c(Cl)c2)CCN(CCCOc2ccc(Cl)c(Cl)c2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d60770bcb50476997f7e87cec0a58de | CCOC(=O)N1CCC(O)(c2ccc(Cl)c(Cl)c2)CC1>>OC1(c2ccc(Cl)c(Cl)c2)CCNCC1 | C(C)OC(=O)N1CCC(CC1)(C1=CC(=C(C=C1)Cl)Cl)O.[OH-].[K+]>>OC1(CCNCC1)C1=CC(=C(C=C1)Cl)Cl | CCOC(=O)[N:13]1[CH2:12][CH2:11][C:2]([OH:1])([c:3]2[cH:4][cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]2)[CH2:15][CH2:14]1>>[OH:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]2)[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | CCOC(=O)N1CCC(O)(c2ccc(Cl)c(Cl)c2)CC1 | OC1(c2ccc(Cl)c(Cl)c2)CCNCC1 | null | null | C(CCC)O | Reduction | Hydrogenolysis of tertiary amines | 6dc5c07be2bf2a2ccc4ff166fd44281ea50e6dda805f74758334dcde1ad7a582 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccc(C2CCNCC2)cc1 | C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 90 | [{"value": 90.0, "product": "OC1(CCNCC1)C1=CC(=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "OC1(CCNCC1)C1=CC(=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 64.2 g of 1-ethoxycarbonyl-4-hydroxy-4-(3,4-dichlorophenyl)piperidine (X-1) and a solution of 72.4 g of KOH in 700 ml of nBuOH is refluxed for 2 hours and evaporated. The reaction mixture is concentrated under reduced pressure and extracted with ethyl acetate. The organic layer is washed with water, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | C(CCC)O | null | null | CCOC(=O)N1CCC(O)(c2ccc(Cl)c(Cl)c2)CC1>C(CCC)O>OC1(c2ccc(Cl)c(Cl)c2)CCNCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1550a2c42379468ab53a6c235e7abb7c | CON=C(C(=O)O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.CSCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1>>CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | CSCC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O.C(Cl)Cl.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)C(C(=O)O)=NOC>>CSCC=1CS[C@H]2N(C1C(=O)O)C(C2NC(C(=NOC)C=2N=C(SC2)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=O)=O | O[C:5]([C:4](=[N:3][O:2][CH3:1])[c:23]1[cH:24][s:25][c:26]([NH:27][C:28]([c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[n:47]1)=[O:6].[NH2:7][CH:8]1[C:9](=[O:10])[N:11]2[C:12]([C:13](=[O:14])[OH:15])=[C:16]([CH2:17][S:18][CH3:19])[CH... | CON=C(C(=O)O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.CSCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | null | null | C(C)(=O)O.CC(=O)C.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | N=C(C(=O)NC1C(=O)N2C=CCS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[#7:4]-[#8:5])-[c:6](:[#7;a:7]):[c:8]:[#16;a:9].[#16:10]-[C:11]1-[#7:12](-[C:13](-[C:14](=[O;D1;H0:15])-[O;D1;H1:16])=[C:17])-[C:18](=[O;D1;H0:19])-[C:20]-1-[NH2;D1;+0:21]>>[#16:10]-[C:11]1-[#7:12](-[C:13](-[C:14](=[O;D1;H0:15])-[O;D1;H1:16])=[C:17])-[C:18](=[O;D1;H0:19])-[C:20]-1-... | null | [] | 20 | CELSIUS | null | null | A mixture of 2.6 g of 3-methylthiomethyl-7-amino-ceph -3-eme-4-carboxylic acid, 26 ml of methylene chloride and 3 ml of triethylamine was stirred at 20° C. under an inert atmosphere and after cooling the mixture to -20° C., an acetone suspension of the mixed anhydride of Example 3 prepared from 6 g of the triethylamine... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1=CN2CC[C@H]2SC1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.CC(=O)C.C(C)N(CC)CC | 20 | null | CON=C(C(=O)O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.CSCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1>C(C)(=O)O.CC(=O)C.C(C)N(CC)CC>CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-add39cef9add4eb09014846177ec4042 | CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(N)n1 | CSCC=1CS[C@H]2N(C1C(=O)O)C(C2NC(C(=NOC)C=2N=C(SC2)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=O)=O.FC(C(=O)O)(F)F>>CSCC=1CS[C@H]2N(C1C(=O)O)C(C2NC(C(=NOC)C=2N=C(SC2)N)=O)=O | c1ccc(C(c2ccccc2)(c2ccccc2)[NH:27][c:26]2[s:25][cH:24][c:23]([C:4](=[N:3][O:2][CH3:1])[C:5](=[O:6])[NH:7][CH:8]3[C:9](=[O:10])[N:11]4[C:12]([C:13](=[O:14])[OH:15])=[C:16]([CH2:17][S:18][CH3:19])[CH2:20][S:21][C@H:22]34)[n:28]2)cc1>>[CH3:1][O:2][N:3]=[C:4]([C:5](=[O:6])[NH:7][CH:8]1[C:9](=[O:10])[N:11]2[C:12]([C:13](=[O... | CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(N)n1 | null | null | null | Deprotection | OtherReaction | 7c27519660e9b0607fb80b9d32b9bfde8e19f5eec1a916a21370255e79658eb1 | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | N=C(C(=O)NC1C(=O)N2C=CCS[C@H]12)c1cscn1 | [#16;a:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:1-[NH;D2;+0:6]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[NH2;D1;+0:6]-[c:5]1:[#16;a:1]:[c:2]:[c:3]:[#7;a:4]:1 | null | [] | 20 | CELSIUS | 20 | MINUTE | A mixture of 6.15 g of the product of Step A and 61 ml of trifluoroacetic acid was stirred at 20° C. for 20 minutes and the mixture was evaporated under reduced pressure at 30° C. to a volume of 15 ml. 150 ml of ispropyl ether were added at 10° C. to the mixture which was then stirred at 20° C. for 15 minutes and was v... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1=CN2CC[C@H]2SC1.c1cscn1 | Other | null | 20 | 0.333333 | CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>CON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(CSC)CS[C@H]12)c1csc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dcaa90fa626041689c210e2969f0e25b | C=CCO.CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1>>C=CCOCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O.B(F)(F)F.C(C=C)O>>C(C=C)OCC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O | [CH2:1]=[CH:2][CH2:3][OH:4].CC(=O)O[CH2:5][C:6]1=[C:7]([C:8](=[O:9])[OH:10])[N:11]2[C:12](=[O:13])[C@@H:14]([NH2:15])[C@H:16]2[S:17][CH2:18]1>>[CH2:1]=[CH:2][CH2:3][O:4][CH2:5][C:6]1=[C:7]([C:8](=[O:9])[OH:10])[N:11]2[C:12](=[O:13])[CH:14]([NH2:15])[C@H:16]2[S:17][CH2:18]1 | C=CCO.CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1 | C=CCOCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | null | null | C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | 4252ee116e29ffa2b694d6e7ecc32c5cf1dbb2ee9625404732e0de7be874bedb | 250047d74ba3e9a91b4a9d25ecfcf45e8445a0f7cdc18c5b9e40c2e06683e003 | O=C1C[C@H]2SCC=CN12 | C-C(=O)-O-[CH2;D2;+0:1]-[C:2](=[C:3](-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[#7:7]-[C:8]=[O;D1;H0:9])-[C:10]-[#16:11].[C;D1;H2:12]=[C:13]-[C:14]-[OH;D1;+0:15]>>[#16:11]-[C:10]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:15]-[C:14]-[C:13]=[C;D1;H2:12])=[C:3](-[C:4](=[O;D1;H0:5])-[O;D1;H1:6])-[#7:7]-[C:8]=[O;D1;H0:9] | null | [] | null | null | null | null | Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of boron trifluoride, 136 ml of allyl alcohol and 115 ml of triethylamine were reacted and the 9 g of raw product was purified successively twice with hot hydrochloric acid and ammonium hydroxide to obtain 4.72 g ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ether | null | null | C1=CN2CC[C@H]2SC1 | HO- | C(C)N(CC)CC | null | null | C=CCO.CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1>C(C)N(CC)CC>C=CCOCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-332c42f9e23541eaa37b1a643ef16125 | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.CCCO>>CCCOCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O.B(F)(F)F.C(CC)O>>C(CC)OCC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O | CC(=O)[O:4][CH2:5][C:6]1=[C:7]([C:8](=[O:9])[OH:10])[N:11]2[C:12](=[O:13])[C@@H:14]([NH2:15])[C@H:16]2[S:17][CH2:18]1.O[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1=[C:7]([C:8](=[O:9])[OH:10])[N:11]2[C:12](=[O:13])[CH:14]([NH2:15])[C@H:16]2[S:17][CH2:18]1 | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.CCCO | CCCOCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | null | null | C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | 4252ee116e29ffa2b694d6e7ecc32c5cf1dbb2ee9625404732e0de7be874bedb | 250047d74ba3e9a91b4a9d25ecfcf45e8445a0f7cdc18c5b9e40c2e06683e003 | O=C1C[C@H]2SCC=CN12 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[C:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7])-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11]-[#16:12].O-[CH2;D2;+0:13]-[C:14]-[C;D1;H3:15]>>[#16:12]-[C:11]-[C:3](-[C:2]-[O;H0;D2;+0:1]-[CH2;D2;+0:13]-[C:14]-[C;D1;H3:15])=[C:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | null | null | Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of of boron trifluoride, 131 ml of propanol and 128 ml of triethylamine were reacted to obtain 17.4 g of raw product which was purified with hot hydrochloric acid and ammonium hydroxide to obtain 7.45 g of 3-propo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ether | null | null | C1=CN2CC[C@H]2SC1 | HO- | C(C)N(CC)CC | null | null | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.CCCO>C(C)N(CC)CC>CCCOCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-563744f14f8d4c1594cf03c6eaa41a0e | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.CC(C)O>>CC(C)OCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O.B(F)(F)F.C(C)(C)O>>C(C)(C)OCC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O | O=[C:2]([CH3:1])[O:4][CH2:5][C:6]1=[C:7]([C:8](=[O:9])[OH:10])[N:11]2[C:12](=[O:13])[C@@H:14]([NH2:15])[C@H:16]2[S:17][CH2:18]1.CC(O)[CH3:3]>>[CH3:1][CH:2]([CH3:3])[O:4][CH2:5][C:6]1=[C:7]([C:8](=[O:9])[OH:10])[N:11]2[C:12](=[O:13])[CH:14]([NH2:15])[C@H:16]2[S:17][CH2:18]1 | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.CC(C)O | CC(C)OCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 | null | null | C(C)N(CC)CC | C-C Coupling | OtherReaction | 4b37754320a3a4e9fa7d05a7c8560982c3763f26a82f39c0cd8c8f3cbc557ca8 | 3344fa8ba720230c95001ed564e60a6abd4a907139323d3507fc29876e94fca3 | O=C1C[C@H]2SCC=CN12 | C-C(-O)-[CH3;D1;+0:1].O=[C;H0;D3;+0:2](-[C;D1;H3:3])-[#8:4]-[C:5]-[C:6]=[C:7]>>[C:7]=[C:6]-[C:5]-[#8:4]-[CH;D3;+0:2](-[C;D1;H3:3])-[CH3;D1;+0:1] | null | [] | null | null | null | null | Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of boron trifluoride, 134 ml of isopropanol and 125 ml of triethylamine were reacted to obtain 16.25 g of raw product which was purified by two successive treatments with hot hydrochloric acid and ammonium hydroxi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Ether | null | null | C1=CN2CC[C@H]2SC1 | HO- | C(C)N(CC)CC | null | null | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.CC(C)O>C(C)N(CC)CC>CC(C)OCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-80f62c1c46ba4eb9a6ba6a91577ca2ab | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.OCc1ccccc1>>NC1C(=O)N2C(C(=O)O)=C(OCc3ccccc3)CS[C@H]12 | B(F)(F)F.CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O.C(C1=CC=CC=C1)O.[OH-].[NH4+].B(F)(F)F>>C(C1=CC=CC=C1)OC=1CS[C@H]2N(C1C(=O)O)C(C2N)=O | CC(=O)OC[C:10]1=[C:6]([C:7](=[O:8])[OH:9])[N:5]2[C:3](=[O:4])[C@@H:2]([NH2:1])[C@H:21]2[S:20][CH2:19]1.[OH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[NH2:1][CH:2]1[C:3](=[O:4])[N:5]2[C:6]([C:7](=[O:8])[OH:9])=[C:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][S:20][C@H:21]12 | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.OCc1ccccc1 | NC1C(=O)N2C(C(=O)O)=C(OCc3ccccc3)CS[C@H]12 | null | null | C(C)(=O)O.Cl.C(C)N(CC)CC | Acylation | OtherReaction | d48ee1196e65f97a301708ef8ff641ddb01af021a1e09c53eb7629c897f78fb1 | ea7fec9b87f263517f6d6d5ea567ba191e6eeb412002bf8de9a1b87edd81c107 | O=C1C[C@H]2SCC(OCc3ccccc3)=CN12 | C-C(=O)-O-C-[C;H0;D3;+0:1]1=[C:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[#7:6](-[C:7]-[#16:8]-[C:9]-1)-[C:10]=[O;D1;H0:11].[OH;D1;+0:12]-[C:13]-[c:14]>>[O;D1;H0:11]=[C:10]-[#7:6]1-[C:7]-[#16:8]-[C:9]-[C;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:13]-[c:14])=[C:2]-1-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | null | [] | null | null | null | null | Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 128 ml of the etherate of boron trifluoride, 126 ml of benzyl alcohol and 90 ml of triethylamine were reacted to obtain 27.1 g of raw product. 25 g of the said product and 250 ml of acetic acid were added to 25 ml of the etherate of bor... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Primary alcohol | Enamine.Ether | C1=CN2CC[C@H]2SC1 | C1=CN2CC[C@H]2SC1 | C1=CN2CC[C@H]2SC1.c1ccccc1 | HO- | C(C)(=O)O.Cl.C(C)N(CC)CC | null | null | CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.OCc1ccccc1>C(C)(=O)O.Cl.C(C)N(CC)CC>NC1C(=O)N2C(C(=O)O)=C(OCc3ccccc3)CS[C@H]12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-15135c6a32ce4d6eb19033f97ae48811 | CSCC1=C(C(=O)O)N2C(=O)C(NC(=O)C(=NO)c3csc(N)n3)[C@H]2SC1>>CSCC1=C(C(=O)[O-])N2C(=O)C(NC(=O)C(=NO)c3csc(N)n3)[C@H]2SC1 | C(C)(=O)[O-].[Na+].C(C)O.CSCC=1CS[C@H]2N(C1C(=O)O)C(C2NC(C(=NO)C=2N=C(SC2)N)=O)=O>>CSCC=1CS[C@H]2N(C1C(=O)[O-])C(C2NC(C(=NO)C=2N=C(SC2)N)=O)=O.[Na+] | [CH3:1][S:2][CH2:3][C:4]1=[C:5]([C:6](=[O:7])[OH:8])[N:9]2[C:10](=[O:11])[CH:12]([NH:13][C:14](=[O:15])[C:16](=[N:17][OH:18])[c:19]3[cH:20][s:21][c:22]([NH2:23])[n:24]3)[C@H:25]2[S:26][CH2:27]1>>[CH3:1][S:2][CH2:3][C:4]1=[C:5]([C:6](=[O:7])[O-:8])[N:9]2[C:10](=[O:11])[CH:12]([NH:13][C:14](=[O:15])[C:16](=[N:17][OH:18])... | CSCC1=C(C(=O)O)N2C(=O)C(NC(=O)C(=NO)c3csc(N)n3)[C@H]2SC1 | CSCC1=C(C(=O)[O-])N2C(=O)C(NC(=O)C(=NO)c3csc(N)n3)[C@H]2SC1 | null | null | CN(C=O)C | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | N=C(C(=O)NC1C(=O)N2C=CCS[C@H]12)c1cscn1 | [#16:1]-[C:2]-[C:3](-[C:4])=[C:5](-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8])-[#7:9]-[C:10]=[O;D1;H0:11]>>[#16:1]-[C:2]-[C:3](-[C:4])=[C:5](-[C:6](-[O-;H0;D1:8])=[O;D1;H0:7])-[#7:9]-[C:10]=[O;D1;H0:11] | null | [] | null | null | null | null | 3.5 ml of a methanolic solution of sodium acetate and 30 ml of ethanol were added to a solution of 1 g of the syn isomer of 3-methylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid in 2 ml of dimethylformamide and the mixture was vacuum filtered. The product was rinsed with e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1=CN2CC[C@H]2SC1.c1cscn1 | null | CN(C=O)C | null | null | CSCC1=C(C(=O)O)N2C(=O)C(NC(=O)C(=NO)c3csc(N)n3)[C@H]2SC1>CN(C=O)C>CSCC1=C(C(=O)[O-])N2C(=O)C(NC(=O)C(=NO)c3csc(N)n3)[C@H]2SC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-259cdfd8194a46da8519bc2b1b2c0ec8 | C=CCOCCCCCCCCCCI.COC(=O)c1ccc(O)cc1>>C=CCOCCCCCCCCCCOc1ccc(C(=O)O)cc1 | [OH-].[K+].C(C=C)OCCCCCCCCCCI.COC(=O)C=1C=CC(=CC1)O.C([O-])([O-])=O.[K+].[K+].Cl>>C(C=C)OCCCCCCCCCCOC1=CC=C(C(=O)O)C=C1 | I[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][CH2:3][CH:2]=[CH2:1].C[O:22][C:20]([c:19]1[cH:18][cH:17][c:16]([OH:15])[cH:24][cH:23]1)=[O:21]>>[CH2:1]=[CH:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([C:20](... | C=CCOCCCCCCCCCCI.COC(=O)c1ccc(O)cc1 | C=CCOCCCCCCCCCCOc1ccc(C(=O)O)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].I-[CH2;D2;+0:9]-[C:10]-[C:11]>>[C:11]-[C:10]-[CH2;D2;+0:9]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 80 | [{"value": 80.0, "product": "C(C=C)OCCCCCCCCCCOC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "C(C=C)OCCCCCCCCCCOC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 70 mmol (22.7 g) of 10-iododecyl allyl ether, 70 mmol (10.6 g) of methyl p-hydroxybenzoate, and 70 mmol (9.6 g) of potassium carbonate were refluxed in absolute ethanol for 15 hours. After addition of an aqueous potassium hydroxide solution (containing 4.0 g of potassium hydroxide) into the reaction solution, the resul... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1 | HI | C(C)O | 80 | null | C=CCOCCCCCCCCCCI.COC(=O)c1ccc(O)cc1>C(C)O>C=CCOCCCCCCCCCCOc1ccc(C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ef2495e77e554402bda2035c66f5f24f | CCOC(OCC)P(=O)(CCC#N)OCC>>CCOC(OCC)P(=O)(CCCN)OCC | [H][H].C(#N)CCP(OCC)(=O)C(OCC)OCC.N>>NCCCP(OCC)(=O)C(OCC)OCC | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH2:11][C:12]#[N:13])[O:14][CH2:15][CH3:16]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH2:11][CH2:12][NH2:13])[O:14][CH2:15][CH3:16] | CCOC(OCC)P(=O)(CCC#N)OCC | CCOC(OCC)P(=O)(CCCN)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | null | null | A solution of 9.6 g of ethyl 2-cyanoethyl(diethoxymethyl)phosphinate in 450 ml of ethanol is added to 82 g of an 8% solution of ammonia in ethanol. To this is added 5 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture is then fil... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CCC#N)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CCCN)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b947884471ff43dea42884fb63629a10 | C/C=C/C#N.CCOC(OCC)P([O-])OCC>>CCOC(OCC)P(=O)(OCC)C(C)CC#N | C(C)(=O)O.C(C)OC(OCC)P(OCC)[O-].C(\C=C\C)#N.[H-].[Na+]>>C(#N)CC(C)P(OCC)(=O)C(OCC)OCC | [CH:13](\[CH3:14])=[CH:15]/[C:16]#[N:17].[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8]([O-:9])[O:10][CH2:11][CH3:12]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([O:10][CH2:11][CH3:12])[CH:13]([CH3:14])[CH2:15][C:16]#[N:17] | C/C=C/C#N.CCOC(OCC)P([O-])OCC | CCOC(OCC)P(=O)(OCC)C(C)CC#N | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [#8:1]-[C:2](-[#8:3])-[P;H0;D3;+0:4](-[O-;H0;D1:5])-[#8:6]-[C:7].[C;D1;H3:8]/[CH;D2;+0:9]=[CH;D2;+0:10]/[C:11]#[N;D1;H0:12]>>[#8:1]-[C:2](-[#8:3])-[P;H0;D4;+0:4](=[O;H0;D1;+0:5])(-[#8:6]-[C:7])-[CH;D3;+0:9](-[C;D1;H3:8])-[CH2;D2;+0:10]-[C:11]#[N;D1;H0:12] | null | [] | null | null | 4 | HOUR | A solution of 23.5 g of ethyl (diethoxymethyl)phosphonite and 6.7 g of crotononitrile in 30 ml of dry ethanol is added to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 ml of ethanol at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature and sti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | 4 | C/C=C/C#N.CCOC(OCC)P([O-])OCC>C(C)O>CCOC(OCC)P(=O)(OCC)C(C)CC#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8451bd41350741798488ec1da4264c87 | CCOC(OCC)P(=O)(OCC)C(C)CC#N>>CCOC(OCC)P(=O)(OCC)C(C)CCN | [H][H].CC(CC#N)P(OCC)(=O)C(OCC)OCC.N>>NCCC(C)P(OCC)(=O)C(OCC)OCC | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([O:10][CH2:11][CH3:12])[CH:13]([CH3:14])[CH2:15][C:16]#[N:17]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([O:10][CH2:11][CH3:12])[CH:13]([CH3:14])[CH2:15][CH2:16][NH2:17] | CCOC(OCC)P(=O)(OCC)C(C)CC#N | CCOC(OCC)P(=O)(OCC)C(C)CCN | null | [Ni] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | null | null | A solution of 17.0 g of ethyl 1-methyl-2-cyanoethyl(diethoxymethyl)phosphinate in 150 ml of ethanol is added to 155.0 g of an 8% solution of ammonia in ethanol. To this are added 10 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(OCC)C(C)CC#N>[Ni].C(C)O>CCOC(OCC)P(=O)(OCC)C(C)CCN |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1ae62f932ea54514b4d903d6fdb8d064 | CCOC(OCC)P(=O)(CC(C)CN)OCC>>CC(CN)CP(O)O.O | NCC(CP(OCC)(=O)C(OCC)OCC)C>>O.NCC(CP(O)O)C | CCOC([P:6]([CH2:5][CH:2]([CH3:1])[CH2:3][NH2:4])([O:7]CC)=[O:8])[O:9]CC>>[CH3:1][CH:2]([CH2:3][NH2:4])[CH2:5][P:6]([OH:7])[OH:8].[OH2:9] | CCOC(OCC)P(=O)(CC(C)CN)OCC | CC(CN)CP(O)O.O | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | null | C-C-O-C(-[O;H0;D2;+0:1]-C-C)-[P;H0;D4;+0:2](=[O;H0;D1;+0:3])(-[C:4]-[C:5])-[O;H0;D2;+0:6]-C-C>>[C:5]-[C:4]-[P;H0;D3;+0:2](-[OH;D1;+0:6])-[OH;D1;+0:3].[OH2;D0;+0:1] | null | [] | null | null | null | null | A solution of 6.0 g of ethyl 3-amino-2-methylpropyl(diethoxymethyl)phosphinate in 30 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 7 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 10 ml of water under re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | null | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(C)CN)OCC>Cl>CC(CN)CP(O)O.O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eef10675c57b4433ad24a46cb58f9591 | C=C(C)C#N.CCOC(OCC)P([O-])OCC>>CCOC(OCC)P(=O)(CC(C)C#N)OCC | C(C)(=O)O.C(C)OC(OCC)P(OCC)[O-].C(C(=C)C)#N.[H-].[Na+]>>C(C)OP(=O)(C(OCC)OCC)CC(C)C#N | [CH2:10]=[C:11]([CH3:12])[C:13]#[N:14].[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8]([O-:9])[O:15][CH2:16][CH3:17]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH3:12])[C:13]#[N:14])[O:15][CH2:16][CH3:17] | C=C(C)C#N.CCOC(OCC)P([O-])OCC | CCOC(OCC)P(=O)(CC(C)C#N)OCC | null | null | C(C)O | Miscellaneous | OtherReaction | 6e18384a4cb428c82c20d31730f2ac142cfbf9a333fe90e3d93fcc2d02070c0d | 62104ffcb4d4ab6482284e0c7ae124bc1d1d4f4befe80d570c6848ac4dc98f52 | null | [#8:1]-[C:2](-[#8:3])-[P;H0;D3;+0:4](-[O-;H0;D1:5])-[#8:6]-[C:7].[C;D1;H3:8]-[C;H0;D3;+0:9](=[CH2;D1;+0:10])-[C:11]#[N;D1;H0:12]>>[#8:1]-[C:2](-[#8:3])-[P;H0;D4;+0:4](=[O;H0;D1;+0:5])(-[#8:6]-[C:7])-[CH2;D2;+0:10]-[CH;D3;+0:9](-[C;D1;H3:8])-[C:11]#[N;D1;H0:12] | null | [] | null | null | 4 | HOUR | A solution of 23.5 g of ethyl (diethoxymethyl)phosphonite and 6.7 g of methacrylonitrile in 30 ml of ethanol is added dropwise to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 ml of ethanol at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | null | null | C(C)O | null | 4 | C=C(C)C#N.CCOC(OCC)P([O-])OCC>C(C)O>CCOC(OCC)P(=O)(CC(C)C#N)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bd87fbc37fc84c7d8ac7af5c2a634c49 | CCOC(OCC)P(=O)(CC(C)C#N)OCC>>CCOC(OCC)P(=O)(CC(C)CN)OCC | [H][H].C(#N)C(CP(OCC)(=O)C(OCC)OCC)C.N>>NCC(CP(OCC)(=O)C(OCC)OCC)C | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH3:12])[C:13]#[N:14])[O:15][CH2:16][CH3:17]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH3:12])[CH2:13][NH2:14])[O:15][CH2:16][CH3:17] | CCOC(OCC)P(=O)(CC(C)C#N)OCC | CCOC(OCC)P(=O)(CC(C)CN)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [C:1]-[C:2](-[C;D1;H3:3])-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[C:1]-[C:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | null | null | null | null | A solution of 17.0 g of ethyl 2-cyanopropyl(diethoxymethyl)phosphinate in 150 ml of ethanol is added to 155 g of an 8% solution of ammonia in ethanol. To this are added 10 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture is the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CC(C)C#N)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CC(C)CN)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-30eae213606d47d0a395349b420efeef | C=CC(C)=O.CCOC(OCC)[PH]([O-])(OCC)[Si](C)(C)C>>CCOC(OCC)P(=O)(CCC(C)=O)OCC | C[Si](C)(C)P(OCC)([O-])C(OCC)OCC.C(=C)C(=O)C.C(Cl)(Cl)Cl>>O=C(CCP(OCC)(=O)C(OCC)OCC)C | [CH2:10]=[CH:11][C:12]([CH3:13])=[O:14].C[Si](C)(C)[PH:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])([O-:9])[O:15][CH2:16][CH3:17]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH2:11][C:12]([CH3:13])=[O:14])[O:15][CH2:16][CH3:17] | C=CC(C)=O.CCOC(OCC)[PH]([O-])(OCC)[Si](C)(C)C | CCOC(OCC)P(=O)(CCC(C)=O)OCC | null | null | O | Miscellaneous | OtherReaction | 7d7e0fb375dd2c5cfc37764f94acfc8098223f35039f3d05eac8e8d72fdb3708 | 5caae0ad5d16d18fc5881c6147ddf5ea7b358c9624a0ebbc0fc9d7ba66c36201 | null | C-[Si](-C)(-C)-[PH;D4;+0:1](-[O-;H0;D1:2])(-[#8:3]-[C:4])-[C:5](-[#8:6])-[#8:7].[C;D1;H3:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[#8:6]-[C:5](-[#8:7])-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[#8:3]-[C:4])-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[C:9](-[C;D1;H3:8])=[O;D1;H0:10] | null | [] | 50 | CELSIUS | 0.5 | HOUR | 15.0 g of ethyl trimethylsilyl(diethoxymethyl)phosphonite are added dropwise to a stirred solution of 3.9 g of methyl vinyl ketone under an atmosphere of nitrogen at room temperature. The mixture is then heated to 50° C. for a period of 1 hour. The mixture is then allowed to cool to room temperature, 25 ml of chlorofor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Vinyl.Silyl protective group | Ketone | null | null | null | Other | O | 50 | 0.5 | C=CC(C)=O.CCOC(OCC)[PH]([O-])(OCC)[Si](C)(C)C>O>CCOC(OCC)P(=O)(CCC(C)=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-88ebe0a4089a43fc83a6dd6a91de9f79 | CCOC(OCC)P(=O)(CCC(C)=O)OCC.[NH4+]>>CCOC(OCC)P(=O)(CCC(C)N)OCC | Cl.O=C(CCP(OCC)(=O)C(OCC)OCC)C.C(C)(=O)[O-].[NH4+].C(#N)[BH3-].[Na+]>>NC(CCP(OCC)(=O)C(OCC)OCC)C | O=[C:12]([CH2:11][CH2:10][P:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])(=[O:9])[O:15][CH2:16][CH3:17])[CH3:13].[NH4+:14]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH2:11][CH:12]([CH3:13])[NH2:14])[O:15][CH2:16][CH3:17] | CCOC(OCC)P(=O)(CCC(C)=O)OCC.[NH4+] | CCOC(OCC)P(=O)(CCC(C)N)OCC | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | null | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH2;D1;+0:5] | null | [] | null | null | 2.5 | HOUR | To a solution of 8.0 g of ethyl 3-oxobutyl(diethoxymethyl)phosphinate in 100 ml of methanol is added 22.8 g of ammonium acetate and 1.3 g of sodium cyanoborohydride. The mixture is stirred under an atmosphere of nitrogen at room temperature for a period of 2.5 h, and then left to stand overnight. The mixture is then ac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | null | HO- | CO | null | 2.5 | CCOC(OCC)P(=O)(CCC(C)=O)OCC.[NH4+]>CO>CCOC(OCC)P(=O)(CCC(C)N)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2d1131dab45645f4ab0bcc2a3bb89e9f | CCOC(OCC)P(=O)(OCC)C(CCN)c1ccc(Cl)cc1>>NCCC(c1ccc(Cl)cc1)P(O)O | NCCC(C1=CC=C(C=C1)Cl)P(OCC)(=O)C(OCC)OCC>>NCCC(C1=CC=C(C=C1)Cl)P(O)O | CCOC(OCC)[P:12]([CH:4]([CH2:3][CH2:2][NH2:1])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)(=[O:13])[O:14]CC>>[NH2:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[P:12]([OH:13])[OH:14] | CCOC(OCC)P(=O)(OCC)C(CCN)c1ccc(Cl)cc1 | NCCC(c1ccc(Cl)cc1)P(O)O | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[O;H0;D2;+0:3]-C-C)-[C:4](-[C:5])-[c:6]>>[C:5]-[C:4](-[c:6])-[P;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:3] | null | [] | null | null | null | null | A solution of 17.9 g of ethyl 3-amino-1-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 200 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 6 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 50 ml of wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(OCC)C(CCN)c1ccc(Cl)cc1>Cl>NCCC(c1ccc(Cl)cc1)P(O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c9b492f8af154b9a8a86074c4ebadc12 | CCOC(OCC)P([O-])OCC.N#CC=Cc1ccc(Cl)cc1>>CCOC(OCC)P(=O)(OCC)C(CC#N)c1ccc(Cl)cc1 | C(C)(=O)O.C(C)OC(OCC)P(OCC)[O-].ClC1=CC=C(C=CC#N)C=C1.[H-].[Na+]>>ClC1=CC=C(C=C1)C(CC#N)P(OCC)(=O)C(OCC)OCC | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8]([O-:9])[O:10][CH2:11][CH3:12].[CH:13](=[CH:14][C:15]#[N:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([O:10][CH2:11][CH3:12])[CH:13]([CH2:14][C:15]#[N:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22... | CCOC(OCC)P([O-])OCC.N#CC=Cc1ccc(Cl)cc1 | CCOC(OCC)P(=O)(OCC)C(CC#N)c1ccc(Cl)cc1 | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | [#8:1]-[C:2](-[#8:3])-[P;H0;D3;+0:4](-[O-;H0;D1:5])-[#8:6]-[C:7].[N;D1;H0:8]#[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:1]-[C:2](-[#8:3])-[P;H0;D4;+0:4](=[O;H0;D1;+0:5])(-[#8:6]-[C:7])-[CH;D3;+0:11](-[CH2;D2;+0:10]-[C:9]#[N;D1;H0:8])-[c:12](:[c:13]):[c:14] | null | [] | null | null | 4 | HOUR | A solution of 25.8 g of ethyl (diethoxymethyl)phosphonite and 18.0 g of 4-chlorocinnamonitrile in 100 ml of ethanol is added to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 ml of ethanol at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)O | null | 4 | CCOC(OCC)P([O-])OCC.N#CC=Cc1ccc(Cl)cc1>C(C)O>CCOC(OCC)P(=O)(OCC)C(CC#N)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ccb1ee78f6554d898be6494680e71a61 | CCOC(OCC)P(=O)(OCC)C(CC#N)c1ccc(Cl)cc1>>CCOC(OCC)P(=O)(OCC)C(CCN)c1ccc(Cl)cc1 | [H][H].ClC1=CC=C(C=C1)C(CC#N)P(OCC)(=O)C(OCC)OCC.N>>NCCC(C1=CC=C(C=C1)Cl)P(OCC)(=O)C(OCC)OCC | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([O:10][CH2:11][CH3:12])[CH:13]([CH2:14][C:15]#[N:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([O:10][CH2:11][CH3:12])[CH:13]([CH2:14][CH2:15][NH2:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[c... | CCOC(OCC)P(=O)(OCC)C(CC#N)c1ccc(Cl)cc1 | CCOC(OCC)P(=O)(OCC)C(CCN)c1ccc(Cl)cc1 | null | [Ni] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccccc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | null | null | A solution of 20 g of ethyl 1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinate in 85 ml of ethanol is added to 131 g of an 8% solution of ammonia in ethanol. To this are added 8.5 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(OCC)C(CC#N)c1ccc(Cl)cc1>[Ni].C(C)O>CCOC(OCC)P(=O)(OCC)C(CCN)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55868750e6b040479bb094ca25ef81c9 | CCOC(OCC)P(=O)(CCC(N)c1ccc(Cl)cc1)OCC>>NC(CCP(O)O)c1ccc(Cl)cc1 | NC(CCP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl>>NC(CCP(O)O)C1=CC=C(C=C1)Cl | CCOC(OCC)[P:5]([CH2:4][CH2:3][CH:2]([NH2:1])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)([O:6]CC)=[O:7]>>[NH2:1][CH:2]([CH2:3][CH2:4][P:5]([OH:6])[OH:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CCOC(OCC)P(=O)(CCC(N)c1ccc(Cl)cc1)OCC | NC(CCP(O)O)c1ccc(Cl)cc1 | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:5])-[OH;D1;+0:2] | null | [] | null | null | null | null | A solution of 10.5 g of ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 100 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 2 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure, and co-evaporated twice with 25 ml of w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CCC(N)c1ccc(Cl)cc1)OCC>Cl>NC(CCP(O)O)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8b74142270b4473b95606c08d755bcbc | C=CC(=O)c1ccc(Cl)cc1.CCOC(OCC)[PH]([O-])(OCC)[Si](C)(C)C>>CCOC(OCC)P(=O)(CCC(=O)c1ccc(Cl)cc1)OCC | C[Si](C)(C)P(OCC)([O-])C(OCC)OCC.C(=C)C(=O)C1=CC=C(C=C1)Cl.C(Cl)(Cl)Cl>>ClC1=CC=C(C(=O)CCP(OCC)(=O)C(OCC)OCC)C=C1 | [CH2:10]=[CH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.C[Si](C)(C)[PH:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])([O-:9])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20... | C=CC(=O)c1ccc(Cl)cc1.CCOC(OCC)[PH]([O-])(OCC)[Si](C)(C)C | CCOC(OCC)P(=O)(CCC(=O)c1ccc(Cl)cc1)OCC | null | null | O | Miscellaneous | OtherReaction | 7d7e0fb375dd2c5cfc37764f94acfc8098223f35039f3d05eac8e8d72fdb3708 | 5caae0ad5d16d18fc5881c6147ddf5ea7b358c9624a0ebbc0fc9d7ba66c36201 | c1ccccc1 | C-[Si](-C)(-C)-[PH;D4;+0:1](-[O-;H0;D1:2])(-[#8:3]-[C:4])-[C:5](-[#8:6])-[#8:7].[CH2;D1;+0:8]=[CH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[#8:6]-[C:5](-[#8:7])-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[#8:3]-[C:4])-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12] | null | [] | null | null | 1 | HOUR | 17.7 g of ethyl trimethylsilyl(diethoxymethyl)phosphonite is added dropwise to a stirred solution of 11.7 g of 4-chlorophenyl vinyl ketone under an atmosphere of nitrogen, at room temperature. The reaction mixture is stirred for a period of 1 hour, 25 ml of chloroform is added followed by 10 ml of water and this mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Vinyl.Silyl protective group | Ketone | null | null | c1ccccc1 | Other | O | null | 1 | C=CC(=O)c1ccc(Cl)cc1.CCOC(OCC)[PH]([O-])(OCC)[Si](C)(C)C>O>CCOC(OCC)P(=O)(CCC(=O)c1ccc(Cl)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-289773cedfb2422f9ae710bf263f973b | CCOC(OCC)P(=O)(CCC(=O)c1ccc(Cl)cc1)OCC.[NH4+]>>CCOC(OCC)P(=O)(CCC(N)c1ccc(Cl)cc1)OCC | Cl.ClC1=CC=C(C(=O)CCP(OCC)(=O)C(OCC)OCC)C=C1.C(C)(=O)[O-].[NH4+].C(#N)[BH3-].[Na+]>>NC(CCP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl | O=[C:12]([CH2:11][CH2:10][P:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])(=[O:9])[O:21][CH2:22][CH3:23])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.[NH4+:13]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH2:11][CH:12]([NH2:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1)[O:... | CCOC(OCC)P(=O)(CCC(=O)c1ccc(Cl)cc1)OCC.[NH4+] | CCOC(OCC)P(=O)(CCC(N)c1ccc(Cl)cc1)OCC | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[NH4+;D0:7]>>[C:3]-[C:2]-[CH;D3;+0:1](-[NH2;D1;+0:7])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 3 | DAY | To a solution of 25.4 g of ethyl 2-(4-chlorobenzoyl)ethyl(diethoxymethyl)phosphinate in 200 ml of methanol is added 52 g of ammonium acetate and 4.23 g of sodium cyanoborohydride. The mixture is stirred under an atmosphere of nitrogen at room temperature for a period of 3 days. The mixture is then acidified to pH 2 wit... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | c1ccccc1 | HO- | CO | null | 72 | CCOC(OCC)P(=O)(CCC(=O)c1ccc(Cl)cc1)OCC.[NH4+]>CO>CCOC(OCC)P(=O)(CCC(N)c1ccc(Cl)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5d3d5e2e87004cd9903c0e82a10c90bf | CCOC(OCC)P(=O)(CC(CN)c1ccc(Cl)cc1)OCC>>NCC(CP(O)O)c1ccc(Cl)cc1 | NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl>>NCC(CP(O)O)C1=CC=C(C=C1)Cl | CCOC(OCC)[P:5]([CH2:4][CH:3]([CH2:2][NH2:1])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)([O:6]CC)=[O:7]>>[NH2:1][CH2:2][CH:3]([CH2:4][P:5]([OH:6])[OH:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CCOC(OCC)P(=O)(CC(CN)c1ccc(Cl)cc1)OCC | NCC(CP(O)O)c1ccc(Cl)cc1 | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:5])-[OH;D1;+0:2] | null | [] | null | null | null | null | A solution of 5.0 g of ethyl 3-amino-2-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 60 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water un... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)c1ccc(Cl)cc1)OCC>Cl>NCC(CP(O)O)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5452f2a370614bcb8a2b00ea97ee9967 | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccc(Cl)cc1>>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(Cl)cc1)OCC | ClC1=CC=C(C=C[N+](=O)[O-])C=C1.C(C)OC(OCC)P(OCC)(=O)C.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li]>>ClC1=CC=C(C=C1)C(CP(OCC)(=O)C(OCC)OCC)C[N+](=O)[O-] | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH3:10])[O:23][CH2:24][CH3:25].[CH:11](=[CH:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][c:19]... | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccc(Cl)cc1 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(Cl)cc1)OCC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Michael addition methyl | 4792ab23977aa8f2d8848039e3cf8e0149eb8bcd2b5b236e5f3910f20c70f1a9 | 62f7b8b1b06d8abe0a7458fcdb08bc1ff61c22493460bb08abd465e204dda1f5 | c1ccccc1 | [#8:1]-[#15:2](-[C:3])(-[CH3;D1;+0:4])=[O;D1;H0:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[#15:2](-[C:3])(=[O;D1;H0:5])-[CH2;D2;+0:4]-[CH;D3;+0:10](-[CH2;D2;+0:9]-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:8])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 10 | MINUTE | To a solution of 1.16 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 7.2 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 2.0 g of ethyl (diethoxymethyl)... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | CCCCCC.O1CCCC1 | null | 0.166667 | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccc(Cl)cc1>CCCCCC.O1CCCC1>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(Cl)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c5a1a84c29f44ee782fe93c28e070f30 | CCOC(OCC)P(=O)(CC(CN)C1CCCCC1)OCC>>NCC(CP(O)O)C1CCCCC1 | NCC(CP(OCC)(=O)C(OCC)OCC)C1CCCCC1>>NCC(CP(O)O)C1CCCCC1 | CCOC(OCC)[P:5]([CH2:4][CH:3]([CH2:2][NH2:1])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)(=[O:6])[O:7]CC>>[NH2:1][CH2:2][CH:3]([CH2:4][P:5]([OH:6])[OH:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | CCOC(OCC)P(=O)(CC(CN)C1CCCCC1)OCC | NCC(CP(O)O)C1CCCCC1 | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | C1CCCCC1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:5] | null | [] | null | null | null | null | A solution of 1.4 g of ethyl 3-amino-2-cyclohexylpropyl(diethoxymethyl)phosphinate in 30 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 hour. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 10 ml of water under... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | C1CCCCC1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)C1CCCCC1)OCC>Cl>NCC(CP(O)O)C1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8eac40f644db47c7bd864d7aafcf3b39 | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccccc1>>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC | [N+](=O)([O-])C=CC1=CC=CC=C1.C(C)OC(OCC)P(OCC)(=O)C.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li]>>[N+](=O)([O-])CC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH3:10])[O:22][CH2:23][CH3:24].[CH:11](=[CH:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][cH:19][cH:20]... | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccccc1 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Michael addition methyl | 4792ab23977aa8f2d8848039e3cf8e0149eb8bcd2b5b236e5f3910f20c70f1a9 | 62f7b8b1b06d8abe0a7458fcdb08bc1ff61c22493460bb08abd465e204dda1f5 | c1ccccc1 | [#8:1]-[#15:2](-[C:3])(-[CH3;D1;+0:4])=[O;D1;H0:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[#15:2](-[C:3])(=[O;D1;H0:5])-[CH2;D2;+0:4]-[CH;D3;+0:10](-[CH2;D2;+0:9]-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:8])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 10 | MINUTE | To a solution of 5.8 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 35.7 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 10.0 g of ethyl (diethoxymethyl... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | CCCCCC.O1CCCC1 | null | 0.166667 | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccccc1>CCCCCC.O1CCCC1>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c56a0fae75ff4778b92cc4966c5ef390 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC>>CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC | [H][H].[N+](=O)([O-])CC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1.N>>NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1 | O=[N+:13]([O-])[CH2:12][CH:11]([CH2:10][P:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])(=[O:9])[O:20][CH2:21][CH3:22])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[O:20][CH2:21][... | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of 1.0 g of ethyl 3-nitro-2-phenylpropyl(diethoxymethyl)phosphinate in 25 ml of ethanol is added to 25 g of an 8% solution of ammonia in ethanol. To this are added 0.5 ml of Raney Nickel and the resulting mixture hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5f9fd3310074c17a1faf12c0f5dc92c | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC>>CCOC(OCC)P(=O)(CC(CN)C1CCCCC1)OCC | NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1>>NCC(CP(OCC)(=O)C(OCC)OCC)C1CCCCC1 | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[O:20][CH2:21][CH3:22]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[O:20][CH2:21][C... | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC | CCOC(OCC)P(=O)(CC(CN)C1CCCCC1)OCC | null | [Rh] | C(C)(C)(C)O | Reduction | Arene hydrogenation | cfd1f3b98f7cd3ca3735c14f302dc0acdc6f0d4501cd6920cbb5c1a3d892ff3a | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCCC1 | [C:1]-[C:2](-[C:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1>>[C:1]-[C:2](-[C:3])-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-1 | null | [] | null | null | 20 | HOUR | A solution of 3.45 g of ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate in 25 ml of tertiary butanol is added to 2.0 g of 5% rhodium in alumina, suspended in 25 ml of tertiary butanol. The resulting mixture is hydrogenated at an atmosphere of 150 bar and temperature of 100° C. for a period of 20 hours. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | C1CCCCC1 | C1CCCCC1 | null | [Rh].C(C)(C)(C)O | null | 20 | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC>[Rh].C(C)(C)(C)O>CCOC(OCC)P(=O)(CC(CN)C1CCCCC1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0233c2129abb4c02a5960c402417b8d8 | CCOC(OCC)P(=O)(CC(CN)Cc1ccccc1)OCC>>NCC(Cc1ccccc1)CP(O)O | NCC(CP(OCC)(=O)C(OCC)OCC)CC1=CC=CC=C1>>NCC(CP(O)O)CC1=CC=CC=C1 | CCOC(OCC)[P:12]([CH2:11][CH:3]([CH2:2][NH2:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)(=[O:13])[O:14]CC>>[NH2:1][CH2:2][CH:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH2:11][P:12]([OH:13])[OH:14] | CCOC(OCC)P(=O)(CC(CN)Cc1ccccc1)OCC | NCC(Cc1ccccc1)CP(O)O | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:5] | null | [] | null | null | null | null | A solution of 3.5 g of ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate in 35 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 3 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)Cc1ccccc1)OCC>Cl>NCC(Cc1ccccc1)CP(O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-856eab2a0560410681b793d4b1b773fd | BrCc1ccccc1.CCOC(OCC)P(=O)(CCC#N)OCC>>CCOC(OCC)P(=O)(CC(C#N)Cc1ccccc1)OCC | C(C1=CC=CC=C1)Br.C(#N)CCP(OCC)(=O)C(OCC)OCC.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li]>>C(C1=CC=CC=C1)C(CP(OCC)(=O)C(OCC)OCC)C#N | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH2:11][C:12]#[N:13])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([C:12]#[N:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[O:21][CH2... | BrCc1ccccc1.CCOC(OCC)P(=O)(CCC#N)OCC | CCOC(OCC)P(=O)(CC(C#N)Cc1ccccc1)OCC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#15:5]-[C:6]-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9]>>[#15:5]-[C:6]-[CH;D3;+0:7](-[C:8]#[N;D1;H0:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 10 | MINUTE | To a solution of 0.97 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 6.0 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 2.0 g of ethyl 2-cyanoethyl(die... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HBr | CCCCCC.O1CCCC1 | null | 0.166667 | BrCc1ccccc1.CCOC(OCC)P(=O)(CCC#N)OCC>CCCCCC.O1CCCC1>CCOC(OCC)P(=O)(CC(C#N)Cc1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37b50643042144889ddbf8ea19fd8458 | CCOC(OCC)P(=O)(CC(C#N)Cc1ccccc1)OCC>>CCOC(OCC)P(=O)(CC(CN)Cc1ccccc1)OCC | [H][H].C(C1=CC=CC=C1)C(CP(OCC)(=O)C(OCC)OCC)C#N.N>>NCC(CP(OCC)(=O)C(OCC)OCC)CC1=CC=CC=C1 | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([C:12]#[N:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[O:21][CH... | CCOC(OCC)P(=O)(CC(C#N)Cc1ccccc1)OCC | CCOC(OCC)P(=O)(CC(CN)Cc1ccccc1)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccccc1 | [C:1]-[C:2](-[C:3])-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[C:1]-[C:2](-[C:3])-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | null | null | null | null | A solution of 3.5 g of ethyl 2-benzyl-2-cyanoethyl(diethoxymethyl)phosphinate in 50 ml of ethanol is added to 25 g of an 8% solution of ammonia in ethanol. To this are added 2 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CC(C#N)Cc1ccccc1)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CC(CN)Cc1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-19a9b1f0815341adbd64aa967ff7b15f | CCOC(OCC)P(=O)(CC(CN)c1ccc(Cl)cc1)OCC>>Cl.NCC(CP(O)O)c1ccc(Cl)cc1 | NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)Cl>>Cl.NCC(CP(O)O)C1=CC=C(C=C1)Cl | CCOC(OCC)[P:6]([CH2:5][CH:4]([CH2:3][NH2:2])[c:9]1[cH:10][cH:11][c:12]([Cl:1])[cH:14][cH:15]1)(=[O:7])[O:8]CC>>[ClH:1].[NH2:2][CH2:3][CH:4]([CH2:5][P:6]([OH:7])[OH:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | CCOC(OCC)P(=O)(CC(CN)c1ccc(Cl)cc1)OCC | Cl.NCC(CP(O)O)c1ccc(Cl)cc1 | null | null | Cl | Miscellaneous | OtherReaction | a1a8c8915d84e005416c9f23b64d1565b30cfa9a9f9a8c6c76d7f39da21921b3 | 1c6f68af3a00735409b48f113e6c8647fe15c8e43c4864833ee19c70c719047c | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C.[Cl;H0;D1;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:5].[Cl;D1;H0:12]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[ClH;D0;+0:6] | null | [] | null | null | null | null | A solution of 5.0 g of ethyl 3-amino-2-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 60 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 hour. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure, and co-evaporated three times with 20 ml o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)c1ccc(Cl)cc1)OCC>Cl>Cl.NCC(CP(O)O)c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a76616da146e429fbd1b8adac259000a | NCC(CP(O)O)c1ccc(Cl)cc1>>NCC(C[PH](=O)[O-])c1ccc(Cl)cc1 | NCC(CP(O)O)C1=CC=C(C=C1)Cl.[OH-].[Na+]>>NCC(CP([O-])=O)C1=CC=C(C=C1)Cl.[Na+] | [NH2:1][CH2:2][CH:3]([CH2:4][P:5]([OH:6])[OH:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[NH2:1][CH2:2][CH:3]([CH2:4][PH:5](=[O:6])[O-:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | NCC(CP(O)O)c1ccc(Cl)cc1 | NCC(C[PH](=O)[O-])c1ccc(Cl)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccccc1 | [C:1]-[C:2]-[P;H0;D3;+0:3](-[OH;D1;+0:4])-[OH;D1;+0:5]>>[C:1]-[C:2]-[PH;D3;+0:3](-[O-;H0;D1:5])=[O;H0;D1;+0:4] | null | [] | null | null | null | null | A solution of 0.25 g of 3-amino-2-(4-chlorophenyl)propylphosphonous acid in 10 ml of 0.1M sodium hydroxide solution is stirred at room temperature for a period of 1 hour, and then concentrated under reduced pressure to give sodium 3-amino-2-(4-chlorophenyl)propylphosphinate as a hygroscopic solid, 31 p=+26.0 ppm (D2O).... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | null | null | null | NCC(CP(O)O)c1ccc(Cl)cc1>>NCC(C[PH](=O)[O-])c1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2bbc92e2ff0d431487501fe1aa3d360f | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC>>NCC(CP(O)O)c1ccccc1 | NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1>>NCC(CP(O)O)C1=CC=CC=C1 | CCOC(OCC)[P:5]([CH2:4][CH:3]([CH2:2][NH2:1])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)(=[O:6])[O:7]CC>>[NH2:1][CH2:2][CH:3]([CH2:4][P:5]([OH:6])[OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC | NCC(CP(O)O)c1ccccc1 | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:5] | null | [] | null | null | null | null | A solution of 4.0 g of ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate in 40 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 2 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduce... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC>Cl>NCC(CP(O)O)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5336d52842114646b59fecae49e4dd9d | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccccc1>>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC | [N+](=O)([O-])C=CC1=CC=CC=C1.C(C)OC(OCC)P(OCC)(=O)C.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li]>>[N+](=O)([O-])CC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH3:10])[O:22][CH2:23][CH3:24].[CH:11](=[CH:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][cH:19][cH:20]... | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccccc1 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Michael addition methyl | 4792ab23977aa8f2d8848039e3cf8e0149eb8bcd2b5b236e5f3910f20c70f1a9 | 62f7b8b1b06d8abe0a7458fcdb08bc1ff61c22493460bb08abd465e204dda1f5 | c1ccccc1 | [#8:1]-[#15:2](-[C:3])(-[CH3;D1;+0:4])=[O;D1;H0:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[#15:2](-[C:3])(=[O;D1;H0:5])-[CH2;D2;+0:4]-[CH;D3;+0:10](-[CH2;D2;+0:9]-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:8])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 10 | MINUTE | To a solution of 5.8 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 35.7 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 10.0 g of ethyl (diethoxymethyl... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | CCCCCC.O1CCCC1 | null | 0.166667 | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccccc1>CCCCCC.O1CCCC1>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7dc71600b17042d78234f99e2162c0fb | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC>>CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC | [H][H].[N+](=O)([O-])CC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1.N>>NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=CC=C1 | O=[N+:13]([O-])[CH2:12][CH:11]([CH2:10][P:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])(=[O:9])[O:20][CH2:21][CH3:22])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[O:20][CH2:21][... | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC | CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of 5.7 g of ethyl 3-nitro-2-phenylpropyl(diethoxymethyl)phosphinate in 60 ml of ethanol is added to 50 g of an 8% solution of ammonia in ethanol. To this are added 9 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccccc1)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CC(CN)c1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a1d96c615d30475b87d289bd7824e029 | CCOC(OCC)P(=O)(CC(CN)c1ccc(F)cc1)OCC>>NCC(CP(O)O)c1ccc(F)cc1 | NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)F>>NCC(CP(O)O)C1=CC=C(C=C1)F | CCOC(OCC)[P:5]([CH2:4][CH:3]([CH2:2][NH2:1])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)([O:6]CC)=[O:7]>>[NH2:1][CH2:2][CH:3]([CH2:4][P:5]([OH:6])[OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1 | CCOC(OCC)P(=O)(CC(CN)c1ccc(F)cc1)OCC | NCC(CP(O)O)c1ccc(F)cc1 | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:5])-[OH;D1;+0:2] | null | [] | null | null | null | null | A solution of 4.4 g of ethyl 3-amino-2-(4-fluorophenyl)propyl(diethoxymethyl)phosphinate in 40 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 2 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water un... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)c1ccc(F)cc1)OCC>Cl>NCC(CP(O)O)c1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ccb81927c486466b913958dd34a1a9b4 | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccc(F)cc1>>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(F)cc1)OCC | FC1=CC=C(C=C[N+](=O)[O-])C=C1.C(C)OP(=O)(C)C(OCC)OCC.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li]>>FC1=CC=C(C=C1)C(CP(OCC)(=O)C(OCC)OCC)C[N+](=O)[O-] | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH3:10])[O:23][CH2:24][CH3:25].[CH:11](=[CH:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][c:19](... | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccc(F)cc1 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(F)cc1)OCC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Michael addition methyl | 4792ab23977aa8f2d8848039e3cf8e0149eb8bcd2b5b236e5f3910f20c70f1a9 | 62f7b8b1b06d8abe0a7458fcdb08bc1ff61c22493460bb08abd465e204dda1f5 | c1ccccc1 | [#8:1]-[#15:2](-[C:3])(-[CH3;D1;+0:4])=[O;D1;H0:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[#15:2](-[C:3])(=[O;D1;H0:5])-[CH2;D2;+0:4]-[CH;D3;+0:10](-[CH2;D2;+0:9]-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:8])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 10 | MINUTE | To a solution of 5.8 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 35.7 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 10.0 g of ethyl(diethoxymethyl)... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | CCCCCC.O1CCCC1 | null | 0.166667 | CCOC(OCC)P(C)(=O)OCC.O=[N+]([O-])C=Cc1ccc(F)cc1>CCCCCC.O1CCCC1>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(F)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6ea9919d85d9467ea82fcb08f059f9d8 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(F)cc1)OCC>>CCOC(OCC)P(=O)(CC(CN)c1ccc(F)cc1)OCC | [H][H].FC1=CC=C(C=C1)C(CP(OCC)(=O)C(OCC)OCC)C[N+](=O)[O-].N>>NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)F | O=[N+:13]([O-])[CH2:12][CH:11]([CH2:10][P:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])(=[O:9])[O:21][CH2:22][CH3:23])[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[... | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(F)cc1)OCC | CCOC(OCC)P(=O)(CC(CN)c1ccc(F)cc1)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of 5.0 g of ethyl 2-(4-fluorophenyl)-3-nitropropyl(diethoxymethyl)phosphinate in 50 ml of ethanol is added to 40 g of an 8% solution of ammonia in ethanol. To this are added 7 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(F)cc1)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CC(CN)c1ccc(F)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2727d84160a24d0ca7d4fd9ff1eb90d8 | CCOC(OCC)P(=O)(CC(CN)c1ccc(C)cc1)OCC>>Cc1ccc(C(CN)CP(O)O)cc1 | NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)C>>NCC(CP(O)O)C1=CC=C(C=C1)C | CCOC(OCC)[P:10]([CH2:9][CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:14][cH:13]1)[CH2:7][NH2:8])(=[O:11])[O:12]CC>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([CH2:7][NH2:8])[CH2:9][P:10]([OH:11])[OH:12])[cH:13][cH:14]1 | CCOC(OCC)P(=O)(CC(CN)c1ccc(C)cc1)OCC | Cc1ccc(C(CN)CP(O)O)cc1 | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:5] | null | [] | null | null | null | null | A solution of 3.7 g of ethyl 3-amino-2-(4-methylphenyl)propyl(diethoxymethyl)phosphinate in 40 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 h. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water un... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)c1ccc(C)cc1)OCC>Cl>Cc1ccc(C(CN)CP(O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-789e38ffe1424cb886e603ae877f3048 | CCOC(OCC)P(C)(=O)OCC.Cc1ccc(C=C[N+](=O)[O-])cc1>>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(C)cc1)OCC | CC1=CC=C(C=C[N+](=O)[O-])C=C1.C(C)OP(=O)(C)C(OCC)OCC.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li]>>CC1=CC=C(C=C1)C(CP(OCC)(=O)C(OCC)OCC)C[N+](=O)[O-] | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH3:10])[O:23][CH2:24][CH3:25].[CH:11](=[CH:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][c:19]([CH3:20])[cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][c:19... | CCOC(OCC)P(C)(=O)OCC.Cc1ccc(C=C[N+](=O)[O-])cc1 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(C)cc1)OCC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Michael addition methyl | 4792ab23977aa8f2d8848039e3cf8e0149eb8bcd2b5b236e5f3910f20c70f1a9 | 62f7b8b1b06d8abe0a7458fcdb08bc1ff61c22493460bb08abd465e204dda1f5 | c1ccccc1 | [#8:1]-[#15:2](-[C:3])(-[CH3;D1;+0:4])=[O;D1;H0:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[#15:2](-[C:3])(=[O;D1;H0:5])-[CH2;D2;+0:4]-[CH;D3;+0:10](-[CH2;D2;+0:9]-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:8])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 10 | MINUTE | To a solution of 8.7 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 53.6 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 15.0 g of ethyl(diethoxymethyl)... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | CCCCCC.O1CCCC1 | null | 0.166667 | CCOC(OCC)P(C)(=O)OCC.Cc1ccc(C=C[N+](=O)[O-])cc1>CCCCCC.O1CCCC1>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(C)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7b87461ecdde45988aceaf88c872f80d | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(C)cc1)OCC>>CCOC(OCC)P(=O)(CC(CN)c1ccc(C)cc1)OCC | [H][H].CC1=CC=C(C=C1)C(CP(OCC)(=O)C(OCC)OCC)C[N+](=O)[O-].N>>NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)C | O=[N+:13]([O-])[CH2:12][CH:11]([CH2:10][P:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])(=[O:9])[O:21][CH2:22][CH3:23])[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20... | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(C)cc1)OCC | CCOC(OCC)P(=O)(CC(CN)c1ccc(C)cc1)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of 6.5 g of ethyl 2-(4-methylphenyl)-3-nitropropyl(diethoxymethyl)phosphinate in 60 ml of ethanol is added to 52 g of an 8% solution of ammonia in ethanol. To this are added 8 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(C)cc1)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CC(CN)c1ccc(C)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3dbe2fa47a034bca8062cd9450dbb32c | CCOC(OCC)P(=O)(CC(CN)c1ccc(OC)cc1)OCC>>COc1ccc(C(CN)CP(O)O)cc1 | NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)OC>>NCC(CP(O)O)C1=CC=C(C=C1)OC | CCOC(OCC)[P:11]([CH2:10][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15][cH:14]1)[CH2:8][NH2:9])([O:12]CC)=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][NH2:9])[CH2:10][P:11]([OH:12])[OH:13])[cH:14][cH:15]1 | CCOC(OCC)P(=O)(CC(CN)c1ccc(OC)cc1)OCC | COc1ccc(C(CN)CP(O)O)cc1 | null | null | Cl | Miscellaneous | OtherReaction | 27a7ce5124ce9df58d78a5aef67d94157caa3dd464298a2201254c2545b8416a | 79a17d37832f2717ceac93b17ac3ad97b0bc0d876910e15be3eeb8366cf301c1 | c1ccccc1 | C-C-O-C(-O-C-C)-[P;H0;D4;+0:1](=[O;H0;D1;+0:2])(-[C:3]-[C:4])-[O;H0;D2;+0:5]-C-C>>[C:4]-[C:3]-[P;H0;D3;+0:1](-[OH;D1;+0:5])-[OH;D1;+0:2] | null | [] | null | null | null | null | A solution of 4.6 g of ethyl 3-amino-2-(4-methoxyphenyl)propyl(diethoxymethyl)phosphinate in 30 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 hour. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | null | null | c1ccccc1 | HO- | Cl | null | null | CCOC(OCC)P(=O)(CC(CN)c1ccc(OC)cc1)OCC>Cl>COc1ccc(C(CN)CP(O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-052fc1659f244dcba4296a66d0377419 | CCOC(OCC)P(C)(=O)OCC.COc1ccc(C=C[N+](=O)[O-])cc1>>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(OC)cc1)OCC | COC1=CC=C(C=C[N+](=O)[O-])C=C1.C(C)OC(OCC)P(OCC)(=O)C.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li]>>COC1=CC=C(C=C1)C(CP(OCC)(=O)C(OCC)OCC)C[N+](=O)[O-] | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH3:10])[O:24][CH2:25][CH3:26].[CH:11](=[CH:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][N+:13](=[O:14])[O-:15])[c:16]1[cH:17][cH:18... | CCOC(OCC)P(C)(=O)OCC.COc1ccc(C=C[N+](=O)[O-])cc1 | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(OC)cc1)OCC | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Michael addition methyl | 4792ab23977aa8f2d8848039e3cf8e0149eb8bcd2b5b236e5f3910f20c70f1a9 | 62f7b8b1b06d8abe0a7458fcdb08bc1ff61c22493460bb08abd465e204dda1f5 | c1ccccc1 | [#8:1]-[#15:2](-[C:3])(-[CH3;D1;+0:4])=[O;D1;H0:5].[O;-;D1;H0:6]-[#7;+:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:1]-[#15:2](-[C:3])(=[O;D1;H0:5])-[CH2;D2;+0:4]-[CH;D3;+0:10](-[CH2;D2;+0:9]-[#7;+:7](-[O;-;D1;H0:6])=[O;D1;H0:8])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 10 | MINUTE | To a solution of 8.7 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 53.6 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 15.0 g of ethyl (diethoxymethyl... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | null | null | c1ccccc1 | null | CCCCCC.O1CCCC1 | null | 0.166667 | CCOC(OCC)P(C)(=O)OCC.COc1ccc(C=C[N+](=O)[O-])cc1>CCCCCC.O1CCCC1>CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(OC)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c7d3f848b65b4035934634d4b5b9371c | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(OC)cc1)OCC>>CCOC(OCC)P(=O)(CC(CN)c1ccc(OC)cc1)OCC | [H][H].COC1=CC=C(C=C1)C(CP(OCC)(=O)C(OCC)OCC)C[N+](=O)[O-].N>>NCC(CP(OCC)(=O)C(OCC)OCC)C1=CC=C(C=C1)OC | O=[N+:13]([O-])[CH2:12][CH:11]([CH2:10][P:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])(=[O:9])[O:22][CH2:23][CH3:24])[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[P:8](=[O:9])([CH2:10][CH:11]([CH2:12][NH2:13])[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[... | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(OC)cc1)OCC | CCOC(OCC)P(=O)(CC(CN)c1ccc(OC)cc1)OCC | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of 6.6 g of ethyl 2-(4-methoxyphenyl)-3-nitropropyl(diethoxymethyl)phosphinate in 50 ml of ethanol is added to 52 g of an 8% solution of ammonia in ethanol. To this are added 8 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C(C)O | null | null | CCOC(OCC)P(=O)(CC(C[N+](=O)[O-])c1ccc(OC)cc1)OCC>[Ni].C(C)O>CCOC(OCC)P(=O)(CC(CN)c1ccc(OC)cc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-765eee938f5f4e1793095537f302f9ea | CC(=O)CC(=O)[O-].N=C(N)NN>>CC(CC(=O)O)=NNC(=N)N | C(CC(=O)C)(=O)[O-].[Li+].C(=N)(N)NN.Cl.C(C)O>>C(N)(=N)NN=C(CC(=O)O)C | O=[C:2]([CH3:1])[CH2:3][C:4](=[O:5])[O-:6].[NH2:7][NH:8][C:9](=[NH:10])[NH2:11]>>[CH3:1][C:2]([CH2:3][C:4](=[O:5])[OH:6])=[N:7][NH:8][C:9](=[NH:10])[NH2:11] | CC(=O)CC(=O)[O-].N=C(N)NN | CC(CC(=O)O)=NNC(=N)N | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 88005d6d8085d6ee296ad8005c0568792897129ef26cedaae52e63e5012734c7 | 348380d82fd877efc76db31f1a616d192c30557986be45e68c3952f08c73a05b | null | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4](-[O-;H0;D1:5])=[O;D1;H0:6].[N;D1;H1:7]=[C:8]-[#7:9]-[NH2;D1;+0:10]>>[C;D1;H3:2]-[C;H0;D3;+0:1](-[C:3]-[C:4](=[O;D1;H0:6])-[OH;D1;+0:5])=[N;H0;D2;+0:10]-[#7:9]-[C:8]=[N;D1;H1:7] | 54.9 | [{"value": 54.9, "product": "C(N)(=N)NN=C(CC(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Lithium acetoacetate (0.655 g) in 2 ml water treated with 0.665 g aminoguanidine HCl in 1.33 ml water. The solution was heated to reflux over 30 minutes and then allowed to cool. Ethanol (10 ml) was added and the mixture was stored at -20° C. for 24 hrs., then at 4° C. for 24 hrs. The mixture was allowed to reach room ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone.Carboxylic acid | null | null | null | HO- | O | null | 24 | CC(=O)CC(=O)[O-].N=C(N)NN>O>CC(CC(=O)O)=NNC(=N)N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a9a5f08948ef490a8633b44f5ca2f366 | C=CC(=O)O.COCCCCCCO>>C=CC(=O)OCCCCCCOC | C1(=CC=C(C=C1)S(=O)(=O)O)C.COC.COCCCCCCO.C(C=C)(=O)O>>C(C=C)(=O)OCCCCCCOC | O[C:3]([CH:2]=[CH2:1])=[O:4].[OH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13]>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13] | C=CC(=O)O.COCCCCCCO | C=CC(=O)OCCCCCCOC | null | null | C1(=CC=CC=C1)C.O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4] | null | [] | null | null | null | null | 803.6 grams of the monomethyl ether described in Part (A) above were azeotropically esterified with 629.8 grams acrylic acid in 254.6 grams toluene in the presence of 24 grams p-toluenesulfonic acid and inhibitors until no more water was collected. Conditions were 95°-98° C., nitrogen sparge in vacuo. On completion, th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | null | HO- | C1(=CC=CC=C1)C.O | null | null | C=CC(=O)O.COCCCCCCO>C1(=CC=CC=C1)C.O>C=CC(=O)OCCCCCCOC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0490a3c74fb84af38fee37a9f0e79743 | COCCOCCO.O>>COC(O)COCCO | O.COCCOCCO.C(C=C)(=O)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C=C)(=O)O.COC(COCCO)O | [CH3:6][O:7][CH2:8][CH2:10][O:11][CH2:12][CH2:13][OH:14].[OH2:9]>>[CH3:6][O:7][CH:8]([OH:9])[CH2:10][O:11][CH2:12][CH2:13][OH:14] | COCCOCCO.O | COC(O)COCCO | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | e436aa388eea9f8fec2004301a7209b67f19650883978f247ad90d876368643d | c5b0d75b63e227d521baa73581cf28339228a50fdabb8eebf3697b67f34937a0 | null | [#8:1]-[C:2]-[CH2;D2;+0:3]-[#8:4]-[C;D1;H3:5].[OH2;D0;+0:6]>>[#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:6])-[#8:4]-[C;D1;H3:5] | null | [] | null | null | null | null | 682 grams Methyl Carbitol (diethylene glycol monomethyl ether, Union Carbide) were azeotropically esterified with 598.9 grams acrylic acid in 272 grams toluene in the presence of 22.8 grams p-toluenesulfonic acid and inhibitors until no more water was collected. Conditions were 95°-98° C., nitrogen sparge in vacuo. On ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether.Secondary alcohol | null | null | null | null | C1(=CC=CC=C1)C | null | null | COCCOCCO.O>C1(=CC=CC=C1)C>COC(O)COCCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da7e98e9ee854ef08afec3f05f935e77 | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2ccccc2)cc1Cl>>Clc1ccc(COc2ccc(Oc3ccccc3)cc2Cl)cn1 | [H-].[Na+].ClC1=C(C=CC(=C1)OC1=CC=CC=C1)O.ClC1=NC=C(C=C1)CCl>>ClC1=NC=C(C=C1)COC1=C(C=C(C=C1)OC1=CC=CC=C1)Cl | Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:23][cH:22]1.[OH:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][c:20]1[Cl:21]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][c:20]2[Cl:21])[cH:22][n:23]1 | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2ccccc2)cc1Cl | Clc1ccc(COc2ccc(Oc3ccccc3)cc2Cl)cn1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Oc2ccc(OCc3cccnc3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]):[c:10] | 70.8 | [{"value": 70.8, "product": "ClC1=NC=C(C=C1)COC1=C(C=C(C=C1)OC1=CC=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 0.09 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there was added dropwise a solution of 0.45 g of 2-chloro-4-phenoxyphenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 30 minutes, a solution of 0.34 g of 2-chloro-5-chloromethylpyridine in 5 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | 0.5 | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2ccccc2)cc1Cl>CN(C=O)C>Clc1ccc(COc2ccc(Oc3ccccc3)cc2Cl)cn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cfef7c7616f74cf4b1c7989b7ccd6e17 | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2cccc(C(F)(F)F)c2)cc1Cl>>FC(F)(F)c1cccc(Oc2ccc(OCc3ccc(Cl)nc3)c(Cl)c2)c1 | [H-].[Na+].ClC1=C(C=CC(=C1)OC1=CC(=CC=C1)C(F)(F)F)O.ClC1=NC=C(C=C1)CCl>>ClC1=NC=C(C=C1)COC1=C(C=C(C=C1)OC1=CC(=CC=C1)C(F)(F)F)Cl | Cl[CH2:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[n:22][cH:23]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([OH:15])[c:24]([Cl:25])[cH:26]2)[cH:27]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][c:20]... | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2cccc(C(F)(F)F)c2)cc1Cl | FC(F)(F)c1cccc(Oc2ccc(OCc3ccc(Cl)nc3)c(Cl)c2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Oc2ccc(OCc3cccnc3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]):[c:10] | null | [] | null | null | 30 | MINUTE | To a solution 0.07 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there was added dropwise a solution of 0.50 g of 2-chloro-4-(3-trifluoromethylphenoxy)phenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 30 minutes, a solution of 0.28 g of 2-chloro-5-chloromethylpyr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | HCl | CN(C=O)C | null | 0.5 | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2cccc(C(F)(F)F)c2)cc1Cl>CN(C=O)C>FC(F)(F)c1cccc(Oc2ccc(OCc3ccc(Cl)nc3)c(Cl)c2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1b4f35597bfc40f99c6612fc401f6e22 | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2cccc(Br)c2)cc1Cl>>Clc1ccc(COc2ccc(Oc3cccc(Br)c3)cc2Cl)cn1 | [H-].[Na+].ClC1=C(C=CC(=C1)OC1=CC(=CC=C1)Br)O.ClC1=NC=C(C=C1)CCl>>ClC1=NC=C(C=C1)COC1=C(C=C(C=C1)OC1=CC(=CC=C1)Br)Cl | Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[n:24][cH:23]1.[OH:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]2)[cH:20][c:21]1[Cl:22]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]3)[cH:20][c:21]2[Cl:22])[cH:... | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2cccc(Br)c2)cc1Cl | Clc1ccc(COc2ccc(Oc3cccc(Br)c3)cc2Cl)cn1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Oc2ccc(OCc3cccnc3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]):[c:10] | null | [] | null | null | 30 | MINUTE | To a solution of 0.07 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there is added dropwise a solution of 0.50 g of 2-chloro-4-(3-bromophenoxy)phenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 30 minutes, a solution of 0.27 g of 2-chloro-5-chloromethylpyridine in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | 0.5 | ClCc1ccc(Cl)nc1.Oc1ccc(Oc2cccc(Br)c2)cc1Cl>CN(C=O)C>Clc1ccc(COc2ccc(Oc3cccc(Br)c3)cc2Cl)cn1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-11045075c0464d549a020ace23fc45e9 | Oc1ccc(Oc2cc(F)cc(F)c2)cc1>>Oc1ccc(Oc2cc(F)cc(F)c2)cc1Cl | FC=1C=C(OC2=CC=C(C=C2)O)C=C(C1)F>>ClC1=C(C=CC(=C1)OC1=CC(=CC(=C1)F)F)O | [OH:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][c:9]([F:10])[cH:11][c:12]([F:13])[cH:14]2)[cH:15][cH:16]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][c:9]([F:10])[cH:11][c:12]([F:13])[cH:14]2)[cH:15][c:16]1[Cl:17] | Oc1ccc(Oc2cc(F)cc(F)c2)cc1 | Oc1ccc(Oc2cc(F)cc(F)c2)cc1Cl | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Addition | Aromatic chlorination | 2e63a9b91d60f82a8e59b7c72ed55b9aec048f26be2f5eb9ca65b1b73867743c | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccc(Oc2ccccc2)cc1 | [O;D1;H1:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[Cl;D1;H0:7]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[O;D1;H1:1]):[c:3] | null | [] | null | null | 5 | HOUR | To a solution of 5.0 g p-(3,5-difluorophenoxy)phenol in 50 mg of carbon tetrachloride, there were added dropwise 2.45 of tert-butylhypochlorous acid with stirring and ice-cooling, and stirring was continued at room temperature for 5 hours. The reaction mixture was concentrated and extracted with 200 ml of ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C(Cl)(Cl)(Cl)Cl | null | 5 | Oc1ccc(Oc2cc(F)cc(F)c2)cc1>C(Cl)(Cl)(Cl)Cl>Oc1ccc(Oc2cc(F)cc(F)c2)cc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7cea9b0826894985a9e86e4b858b5be2 | BrCCCCCCBr.OCCc1ccccc1>>BrCCCCCCOCCc1ccccc1 | C(CC1=CC=CC=C1)O.BrCCCCCCBr.[OH-].[Na+]>>BrCCCCCCOCCC1=CC=CC=C1 | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1].[OH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | BrCCCCCCBr.OCCc1ccccc1 | BrCCCCCCOCCc1ccccc1 | null | S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 55.7 | [{"value": 55.7, "product": "BrCCCCCCOCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of phenethyl alcohol (20 g), 1,6-dibromohexane (195 g) and tetrabutylammonium bisulphate (3.0 g) in 50% w/v NaOH solution (100 ml) was heated at 65-70° for 4h. The cooled reaction mixture was poured into H2O (400 ml) and extracted with CX (2×300 ml). The dried extracts were evaporated in vacuo to give a yello... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC.O | null | null | BrCCCCCCBr.OCCc1ccccc1>S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC.O>BrCCCCCCOCCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-17aed5b9702b46f69ddfc58fdccf4fd4 | BrCCCCCCBr.OCCCCc1ccccc1>>BrCCCCCCOCCCCc1ccccc1 | O.[H-].[Na+].C1(=CC=CC=C1)CCCCO.BrCCCCCCBr>>BrCCCCCCOCCCCC1=CC=CC=C1 | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | BrCCCCCCBr.OCCCCc1ccccc1 | BrCCCCCCOCCCCc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 48 | [{"value": 48.0, "product": "BrCCCCCCOCCCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | NaH (46% dispersion in oil; 6.5 g) was added portionwise to a solution of 4-phenyl-1-butanol (15.0 g) and 1,6-dibromohexane (48.8 g) in THF (200 ml) under nitrogen. The resulting suspension was refluxed for 27 h and treated with H2O (80 ml). The mixture was extracted with ER (2×200 ml) and the dried extract was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | C1CCOC1 | null | null | BrCCCCCCBr.OCCCCc1ccccc1>C1CCOC1>BrCCCCCCOCCCCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c168fac950b8444d8d024b6f43774ded | C=C(C)OC.O=C(CBr)c1ccc(O)c(CO)c1>>CC1(C)OCc2cc(C(=O)CBr)ccc2O1 | COC(=C)C.BrCC(=O)C1=CC(=C(C=C1)O)CO.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrCC(=O)C1=CC2=C(OC(OC2)(C)C)C=C1 | CO[C:2](=[CH2:1])[CH3:3].[OH:4][CH2:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[CH2:11][Br:12])[cH:13][cH:14][c:15]1[OH:16]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][c:6]2[cH:7][c:8]([C:9](=[O:10])[CH2:11][Br:12])[cH:13][cH:14][c:15]2[O:16]1 | C=C(C)OC.O=C(CBr)c1ccc(O)c(CO)c1 | CC1(C)OCc2cc(C(=O)CBr)ccc2O1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 0f672d215e527014d9141e70d05d5718fa217fdfa248c8eb2528a90aa9055ba8 | 8119ee9e00187f1c0b478e3c1dce92c3b914153c12cfed038c7de8671ef37557 | c1ccc2c(c1)COCO2 | C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[CH2;D1;+0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[CH3;D1;+0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]-[O;H0;D2;+0:9]-1 | 82.5 | [{"value": 82.5, "product": "BrCC(=O)C1=CC2=C(OC(OC2)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Methoxypropene (10 g) was added over 15 min to a stirred solution of 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone (5 g) and toluene-4-sulphonic acid (0.5 g) in CH2Cl2 (100 ml) at 23°. The mixture was stirred for 3h, filtered through a wad of triethylamine-deactivated silica and evaporated to give an oil. Pur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Aromatic alcohol.Vinyl | Ether.Ether | null | c1ccc2c(c1)COCO2 | c1ccc2c(c1)COCO2 | HO- | C(Cl)Cl | null | null | C=C(C)OC.O=C(CBr)c1ccc(O)c(CO)c1>C(Cl)Cl>CC1(C)OCc2cc(C(=O)CBr)ccc2O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b0c4d599e3284cc39dfd6ae880a00517 | BrCCCCCCBr.OCCCc1ccccc1>>BrCCCCCCOCCCc1ccccc1 | C1(=CC=CC=C1)CCCO.S(=O)(=O)(O)O.BrCCCCCCBr.[OH-].[Na+]>>BrCCCCCCOCCCC=1C=CC=CC1 | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1].[OH:8][CH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | BrCCCCCCBr.OCCCc1ccccc1 | BrCCCCCCOCCCc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 1,223 | [{"value": 1223.0, "product": "BrCCCCCCOCCCC=1C=CC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Phenylpropanol (3.00 g) and 1,6-dibromohexane hydrogen sulphate (0.5 g) and 12.5 M aqueous NaOH (16 ml) for 30 h. The mixture was diluted with H2O (80 ml), extracted with ER (3×100 ml), and the combined organic extracts were washed consecutively with H2O (80 ml) and BR (80 ml). The dried extracts were evaporated and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | O | null | null | BrCCCCCCBr.OCCCc1ccccc1>O>BrCCCCCCOCCCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ac03c135aa2e493cb63eaf76ba6c32fa | BrCCCCCCBr.COc1ccccc1CCCCO>>COc1ccccc1CCCCOCCCCCCBr | O.[H-].[Na+].COC1=C(C=CC=C1)CCCCO.BrCCCCCCBr>>BrCCCCCCOCCCCC1=C(C=CC=C1)OC | Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][CH2:11][CH2:12][OH:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20] | BrCCCCCCBr.COc1ccccc1CCCCO | COc1ccccc1CCCCOCCCCCCBr | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 58.8 | [{"value": 58.8, "product": "BrCCCCCCOCCCCC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | NaH (46% dispersion in oil; 1.36 g) was added portionwise to a solution of 2-methoxybenzenebutanol (5.0 g) and 1,6-dibromohexane (13.8 g) in THF (50 ml). The suspension was refluxed for 20 h and was treated cautiously with H2O (20 ml). The resulting emulsion was extracted with ER (2×50 ml) and the dried extract was eva... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | C1CCOC1 | null | null | BrCCCCCCBr.COc1ccccc1CCCCO>C1CCOC1>COc1ccccc1CCCCOCCCCCCBr |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5c394360b9934f6ea34c45ca866ffcda | BrCCCc1ccccc1.C1COC1>>OCCCCCCc1ccccc1 | BrCCCC1=CC=CC=C1.[Mg].[NH4+].[Cl-].O1CCC1>>C1(=CC=CC=C1)CCCCCCO | Br[CH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[O:1]1[CH2:2][CH2:3][CH2:4]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | BrCCCc1ccccc1.C1COC1 | OCCCCCCc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 637c455f8adb2e182e9efd933b19dd0e74f5dc12d12c6269b2293bb0d517dc42 | 30e13948c8786a09f1276ae1d49b379da946c0f461d188344ec892c684344fba | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH2;D2;+0:6]-[C:5]-[C:4]-[OH;D1;+0:7] | 33.8 | [{"value": 33.8, "product": "C1(=CC=CC=C1)CCCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (3-Bromopropyl)benzene (20 g) in THF (75 ml) was added dropwise to magnesium (2.43 g) at a rate to maintain gentle reflux. The mixture was stirred for 2 h at RT and oxetane (10 g) was added dropwise. The resulting suspension was stirred at RT for 2h and at reflux for 16 h and poured into saturated aqueous NH4Cl (100 ml... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Primary alcohol | C1COC1 | null | c1ccccc1 | Br- | C1CCOC1 | null | 2 | BrCCCc1ccccc1.C1COC1>C1CCOC1>OCCCCCCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8d888550453845d89f366f2eeaefe39f | C1=COCCC1.OCCCCCl>>ClCCCCOC1CCCCO1 | O1CCCC=C1.ClCCCCO>>ClCCCCOC1OCCCC1 | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6]>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.OCCCCCl | ClCCCCOC1CCCCO1 | null | Cl | null | 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]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | 89.9 | [{"value": 89.9, "product": "ClCCCCOC1OCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Dihydropyran (15.5 g) was added dropwise to a mixture of 4-chlorobutanol (20 g) and hydrochloric acid (18 M, 1 drop) at RT. The mixture was stirred for 30 min and washed with H2O (100 ml), aqueous NaHCO3 (1 M, 50 ml) and BR (50 ml). The dried liquid was heated under reduced pressure to leave the title compound as a col... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | Cl | null | 0.5 | C1=COCCC1.OCCCCCl>Cl>ClCCCCOC1CCCCO1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-acc0d0ac996740c1aa636be541a52c57 | BrCCCCCCBr.Cc1cccc(C)c1CCO>>Cc1cccc(C)c1CCOCCCCCCBr | [H-].[Na+].CC1=C(C(=CC=C1)C)CCO.BrCCCCCCBr.O>>BrCCCCCCOCCC1=C(C=CC=C1C)C | Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[CH2:9][CH2:10][OH:11]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18] | BrCCCCCCBr.Cc1cccc(C)c1CCO | Cc1cccc(C)c1CCOCCCCCCBr | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | 52.7 | [{"value": 52.7, "product": "BrCCCCCCOCCC1=C(C=CC=C1C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | NaH (46% dispersion in oil; 4.2 g) was added portionwise to a solution f 2,6-dimethylbenzenethanol (6.0 g) and 1,6-dibromohexane (19.52 g) in THF (50 ml) under nitrogen. The mixture was refluxed for 18 h and treated cautiously with H2O (20 ml). The resulting emulsion was extracted with ER (3×100 ml) and the dried extra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | C1CCOC1 | null | null | BrCCCCCCBr.Cc1cccc(C)c1CCO>C1CCOC1>Cc1cccc(C)c1CCOCCCCCCBr |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-818d644ce64a41d8816409c37119191b | C1COC1.Fc1ccc(Br)cc1>>OCCCc1ccc(F)cc1 | II.O1CCC1.[NH4+].[Cl-].BrC1=CC=C(C=C1)F.[Mg]>>FC1=CC=C(C=C1)CCCO | [O:1]1[CH2:2][CH2:4][CH2:3]1.Br[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1>>[OH:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1 | C1COC1.Fc1ccc(Br)cc1 | OCCCc1ccc(F)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | ab402a405392853d5b7c6e8072d47a43f8468f3d0c950058e1f959f41ce09a3a | 104534dc5f965e596cd2f673f5d9f6169287a1e8ccc931bc81d74b3081323966 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH2;D2;+0:6]1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[OH;D1;+0:9]-[CH2;D2;+0:6]-[CH2;D2;+0:8]-[CH2;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 51.6 | [{"value": 51.6, "product": "FC1=CC=C(C=C1)CCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A Grignard reagent was prepared from 4-bromo-1-fluorobenzene (8.0 g)., magnesium turnings (1.10 g), and iodine (one small crystal) in THF (40 ml). Oxetane (2.3 g) in THF (10 ml) was added at RT and the reaction mixture was heated at reflux overnight. The cooled solution was poured into aqueous saturated NH4Cl (100 ml),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Primary alcohol | C1COC1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | C1CCOC1 | null | null | C1COC1.Fc1ccc(Br)cc1>C1CCOC1>OCCCc1ccc(F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b66b5c858c9f4603b5c7693801f728e2 | BrCCCCCCBr.COc1ccc(CCO)cc1>>COc1ccc(CCOCCCCCCBr)cc1 | COC1=CC=C(C=C1)CCO.BrCCCCCCBr.[OH-].[Na+]>>BrCCCCCCOCCC1=CC=C(C=C1)OC | Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:16])[cH:17][cH:18]1 | BrCCCCCCBr.COc1ccc(CCO)cc1 | COc1ccc(CCOCCCCCCBr)cc1 | null | S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | 237.5 | [{"value": 237.5, "product": "BrCCCCCCOCCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Methoxybenzeneethanol (5.0 g) and 1,6-dibromohexane (23.7 g) were stirred rapidly at RT with tetra-n-butyl ammonium bisulphate (0.94 g) and 12.5 M aqueous NaOH (30 ml) for 16 h. The mixture was diluted with H2O (125 ml), extracted with ER (3×150 ml) and the combined organic extracts were washed consecutively with H2O... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC.O | null | null | BrCCCCCCBr.COc1ccc(CCO)cc1>S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC.O>COc1ccc(CCOCCCCCCBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e69fe70ae7ca4200a4a1976a61404a61 | BrCCCCCBr.OCCc1ccc(F)cc1>>Fc1ccc(CCOCCCCCBr)cc1 | FC1=CC=C(C=C1)CCO.BrCCCCCBr.[OH-].[Na+]>>BrCCCCCOCCC1=CC=C(C=C1)F | Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14].[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][OH:8])[cH:15][cH:16]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14])[cH:15][cH:16]1 | BrCCCCCBr.OCCc1ccc(F)cc1 | Fc1ccc(CCOCCCCCBr)cc1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | null | [] | null | null | null | null | 4-Fluorobenzeneethanol (10.0 g), 1,5-dibromopentane (29 ml), tetra-n-butylammonium hydrogen sulphate (3.2 g, 9 mmol), and aqueous 12.5 M NaOH (109 ml) were stirred vigorously at RT overnight. The mixture was diluted with H2O (400 ml), extracted with ER (3×200 ml), and the combined organic extracts were evaporated. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O | null | null | BrCCCCCBr.OCCc1ccc(F)cc1>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>Fc1ccc(CCOCCCCCBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b8644227ad934494a702894e391ecfb3 | BrCCCCCBr.COc1ccc(CCCO)cc1>>COc1ccc(CCCOCCCCCBr)cc1 | COC1=CC=C(C=C1)CCCO.BrCCCCCBr.[OH-].[Na+]>>BrCCCCCOCCCC1=CC=C(C=C1)OC | Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][OH:10])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:16])[cH:17][cH:18]1 | BrCCCCCBr.COc1ccc(CCCO)cc1 | COc1ccc(CCCOCCCCCBr)cc1 | null | S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | 244.6 | [{"value": 244.6, "product": "BrCCCCCOCCCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Methoxybenzenepropanol (7.5 g) and 1,5 dibromopentane (30.5 g) were stirred rapidly at RT with tetra-n-butylammonium bisulphate (1.02 g) and 12.5 M aqueous NaOH (36 ml) for 16 h. The mixture was diluted with H2O (170 ml), extracted with ER (3×20 ml) and the combined organic extracts were washed consecutively with H2O... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC.O | null | null | BrCCCCCBr.COc1ccc(CCCO)cc1>S([O-])(O)(=O)=O.C(CCC)[N+](CCCC)(CCCC)CCCC.O>COc1ccc(CCCOCCCCCBr)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-514bf848f79a4968bbf480ff0bb655b9 | BrCCOCCCc1ccccc1.C#CC(C)(C)N>>CC(C)(N)C#CCCOCCCc1ccccc1 | CC(C)(C#C)N.[Li+].[NH2-].BrCCOCCCC1=CC=CC=C1>>CC(C#CCCOCCCC1=CC=CC=C1)(N)C | Br[CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][C:2]([CH3:3])([NH2:4])[C:5]#[CH:6]>>[CH3:1][C:2]([CH3:3])([NH2:4])[C:5]#[C:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | BrCCOCCCc1ccccc1.C#CC(C)(C)N | CC(C)(N)C#CCCOCCCc1ccccc1 | null | null | N | C-C Coupling | OtherReaction | a2902088eeffba8af7cde0e465024f8c5b6cd6239687cb7ab88d93a01519cd51 | 65c5c213019f4e08c3c32f7e1ced539ac3ff1efc4a39855e6d21bd16502eefc5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]#[CH;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:6]#[C:5]-[C:4] | 13.8 | [{"value": 13.8, "product": "CC(C#CCCOCCCC1=CC=CC=C1)(N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | 1,1-Dimethylpropargylamine (8.5 g) was added dropwise to a suspension of lithamide [from lithium (1.7 g)] in liquid ammonia (100 ml) at -33°. The mixture was stirred for 90 min and a solution of [3-(2-bromoethoxy)propyl]benzene (21.5 g) in ER (30 ml) was added dropwise. The suspension was stirred at 4 h and ammonia was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Alkyne | Alkyne | null | null | c1ccccc1 | HBr | N | null | 1.5 | BrCCOCCCc1ccccc1.C#CC(C)(C)N>N>CC(C)(N)C#CCCOCCCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cea66657c1d54213bd0be73281450b4e | CNC.COC(=O)c1cc(C(=O)CBr)ccc1OCc1ccccc1>>COC(=O)c1cc(C(O)CN(C)C)ccc1OCc1ccccc1 | CNC.BrCC(=O)C=1C=CC(=C(C(=O)OC)C1)OCC1=CC=CC=C1.[BH4-].[Na+]>>CN(CC(O)C=1C=CC(=C(C(=O)OC)C1)OCC1=CC=CC=C1)C | [NH:11]([CH3:12])[CH3:13].Br[CH2:10][C:8]([c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:15][cH:14]1)=[O:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]([OH:9])[CH2:10][N:11]([CH3:12])[CH3:13])[cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21... | CNC.COC(=O)c1cc(C(=O)CBr)ccc1OCc1ccccc1 | COC(=O)c1cc(C(O)CN(C)C)ccc1OCc1ccccc1 | null | null | C(C)O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | a65602a3b96095e5dbb2f138d3f287ce56a941015a66cef48c8137cee7280ea1 | 45a6cc47e2b15c343ede1c801f826eabfff338b5dc3020746051ac4edcfff0cc | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | Dimethylamine (33% in ethanol, 156 ml) was added to a stirred suspension of methyl 5-(bromoacetyl)-2-(phenylmethoxy)benzoate (105.8 g) in absolute ethanol (1l) and THF (1l). The resulting solution was stirred at RT for 2 h, treated with NaBH4 (25 g) and stirred at RT overnight. The solvent was removed in vacuo and H2O ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Secondary alcohol.Tertiary amine | null | null | c1ccccc1.c1ccccc1 | Br- | C(C)O.C1CCOC1 | null | 2 | CNC.COC(=O)c1cc(C(=O)CBr)ccc1OCc1ccccc1>C(C)O.C1CCOC1>COC(=O)c1cc(C(O)CN(C)C)ccc1OCc1ccccc1 |
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