dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d99672bc286434e8155aafff5a7504c | Br.O=S(c1ccccc1)c1ccccc1.[Br][Mg][c]1ccccc1>>[Br-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | Br.O.C1(=CC=CC=C1)[Mg]Br.C1(=CC=CC=C1)S(=O)C1=CC=CC=C1>>[Br-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 | [BrH:1].O=[S:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[Br][Mg][c:5]1[cH:4][cH:3][cH:2][cH:20][cH:19]1>>[Br-:1].[cH:2]1[cH:3][cH:4][c:5]([S+:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | Br.O=S(c1ccccc1)c1ccccc1.[Br][Mg][c]1ccccc1 | [Br-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | null | null | ClCCl.CCOCC.C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | c3e7e19d16f475257b9d7bc8805000711de7a96dce38a8ec7729a2cf783f497d | e08c543ca026a873c4684fb790ce1775b9f286e62a7470c5b30c446c7de9db77 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | O=[S;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[BrH;D0;+0:8].[Br]-[Mg]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[Br-;H0;D0:8].[c:6]:[c:5](-[S+;H0;D3:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:7] | 49 | [{"value": 49.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a 3-necked 1 L round bottom flask equipped with a still head was added phenylmagnesium bromide (3 M in diethyl ether, 142 ml, 0.426 mol) followed by dry benzene (150 ml). The flask was connected to a water aspirator and the diethyl ether removed under vacuo by gently heating. Additional benzene (150 ml) was added an... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Sulfoxide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HBr.Mg | ClCCl.CCOCC.C1=CC=CC=C1 | null | 8 | Br.O=S(c1ccccc1)c1ccccc1.[Br][Mg][c]1ccccc1>ClCCl.CCOCC.C1=CC=CC=C1>[Br-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-859a3ba4fca04957adca8f06dc6bef2a | Cc1ccc(S(=O)(=O)O)cc1>>Cc1ccc(S(=O)(=O)[O-])cc1 | [Br-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>S(=O)(=O)([O-])C1=CC=C(C)C=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[OH:9])[cH:10][cH:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O-:9])[cH:10][cH:11]1 | Cc1ccc(S(=O)(=O)O)cc1 | Cc1ccc(S(=O)(=O)[O-])cc1 | null | null | O | Oxidation | OtherReaction | 8411f9fce1f185c5c08a89a741e7494817f2d5e55ac6ad2b663e4ffb9ef8fbab | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | c1ccccc1 | [C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]:[c:11]:1>>[C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[#16:6](-[O-;H0;D1:9])(=[O;D1;H0:7])=[O;D1;H0:8]):[c:10]:[c:11]:1 | 73.1 | [{"value": 73.1, "product": "S(=O)(=O)([O-])C1=CC=C(C)C=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of triphenylsulfonium bromide (6.87 g, 20.0 mmol) and p-toluenesulfonic acid (3.80 g, 20.0 mmol) in water (100 ml) was heated at a gentle reflux for 15 hours under nitrogen. After cooling to room temperature, the clear solution was extracted with dichloromethane (4×75 ml). The combined organic extracts were ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | O | null | null | Cc1ccc(S(=O)(=O)O)cc1>O>Cc1ccc(S(=O)(=O)[O-])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7722dbce85914723bdf979fd6d719ccd | COc1cc(C)cc(OC)c1N.O=C1CCCCC1>>COc1cc(C)cc(OC)c1N=C1CCCCC1 | COC1=C(N)C(=CC(=C1)C)OC.C1(CCCCC1)=O.O>>C1(CCCCC1)=NC1=C(C=C(C=C1OC)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH2:12].O=[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[N:12]=[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | COc1cc(C)cc(OC)c1N.O=C1CCCCC1 | COc1cc(C)cc(OC)c1N=C1CCCCC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 2a9250de46baa538fbac4be937bbfb8f618e542288312ab646db5d230a5cbab9 | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | c1ccc(N=C2CCCCC2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:4]-[C:5] | null | [] | null | null | null | null | 4.2 g of 2,6-dimethoxy-4-methylaniline are dissolved in 50 ml of toluene, 2.45 g of cyclohexanone are then added and the reaction mixture is heated at reflux for 18 hours. The water which is formed is removed as it is formed in the reaction mixture using a Dean and Stark apparatus. The toluene is evaporated and the oil... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | C1(=CC=CC=C1)C | null | null | COc1cc(C)cc(OC)c1N.O=C1CCCCC1>C1(=CC=CC=C1)C>COc1cc(C)cc(OC)c1N=C1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bdd11d2834694a83af8ab75f8ab8834a | CC(=O)[O-].COc1cc(C)cc(OC)c1B(O)O.[Pb+4]>>CC(=O)[O-].COc1cc(C)cc(OC)[c]1[Pb+3] | COC1=C(C(=CC(=C1)C)OC)B(O)O.C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].[Pb+4]>>C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].COC1=C(C(=CC(=C1)C)OC)[Pb+3] | [CH3:9][C:10](=[O:11])[O-:12].OB(O)[c:23]1[c:15]([O:14][CH3:13])[cH:16][c:17]([CH3:18])[cH:19][c:20]1[O:21][CH3:22].[Pb+4:24]>>[CH3:9][C:10](=[O:11])[O-:12].[CH3:13][O:14][c:15]1[cH:16][c:17]([CH3:18])[cH:19][c:20]([O:21][CH3:22])[c:23]1[Pb+3:24] | CC(=O)[O-].COc1cc(C)cc(OC)c1B(O)O.[Pb+4] | CC(=O)[O-].COc1cc(C)cc(OC)[c]1[Pb+3] | null | null | ClCCl.C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | c8a986ce245c41ad17a28261bfa049d34a1ff30e54891e5edf3c7e9763daeea9 | 85a3f4ccaf1467b0e39ffb6db17694f38d643e804885c98ae45b58a6f05bcc99 | c1ccccc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2](-[#8:3]):[c:4]):[c:5](-[#8:6]):[c:7].[Pb+4;H0;D0:8]>>[#8:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[Pb+3;H0;D1:8]):[c:5](-[#8:6]):[c:7] | 90 | [{"value": 90.0, "product": "C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].COC1=C(C(=CC(=C1)C)OC)[Pb+3]", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 75 | MINUTE | 45.4 g of lead tetraacetate and 3.2 g of mercuric acetate are suspended in 150 ml of anhydrous chloroform and the mixture is heated to 40° C. under an argon atmosphere. A solution of 20 g of 2,6-dimethoxy-4-methylphenylboronic acid (prepared above) in 100 ml of chloroform is added dropwise to the reaction mixture at 40... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO-.B | ClCCl.C(Cl)(Cl)Cl | 40 | 1.25 | CC(=O)[O-].COc1cc(C)cc(OC)c1B(O)O.[Pb+4]>ClCCl.C(Cl)(Cl)Cl>CC(=O)[O-].COc1cc(C)cc(OC)[c]1[Pb+3] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b26dbc0c04294a50977806d36b2d0d07 | COc1cc(C)cc(OC)[c]1[Pb+3].NC1CCCCCCC1>>COc1cc(C)cc(OC)c1NC1CCCCCCC1 | C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].COC1=C(C(=CC(=C1)C)OC)[Pb+3].C1(CCCCCCC1)N>>C1(CCCCCCC1)NC1=C(C=C(C=C1OC)C)OC | [Pb+3][c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([CH3:6])[cH:7][c:8]1[O:9][CH3:10].[NH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | COc1cc(C)cc(OC)[c]1[Pb+3].NC1CCCCCCC1 | COc1cc(C)cc(OC)c1NC1CCCCCCC1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 2deb6f1e1aa47aa3aca27744bf9128d0bc67c4eb5ed55eed5e02e068a211a4da | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccc(NC2CCCCCCC2)cc1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[Pb+3]):[c:5](-[#8:6]):[c:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH;D2;+0:10]-[C:9](-[C:8])-[C:11]):[c:5](-[#8:6]):[c:7] | 52 | [{"value": 52.0, "product": "C1(CCCCCCC1)NC1=C(C=C(C=C1OC)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 10.56 g of cyclooctylamine are dissolved in 500 ml of anhydrous dichloromethane and 1.5 g of cupric acetate are added thereto. A solution of 44.2 g of 2,6-dimethoxy-4-methylphenyllead triacetate, prepared above, in 250 ml of anhydrous dichloromethane is added dropwise to the reaction mixture under an inert atmosphere. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCCCC1 | Other | ClCCl | null | 18 | COc1cc(C)cc(OC)[c]1[Pb+3].NC1CCCCCCC1>ClCCl>COc1cc(C)cc(OC)c1NC1CCCCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a85fcfa6da084f02a5caf57a4c6ff853 | COc1cc(C)cc(OC)c1N.O=C1C2CC3CC(C2)CC1C3>>COc1cc(C)cc(OC)c1NC1C2CC3CC(C2)CC1C3 | COC1=C(N)C(=CC(=C1)C)OC.C(=O)O.C12C(C3CC(CC(C1)C3)C2)=O>>C12C(C3CC(CC(C1)C3)C2)NC2=C(C=C(C=C2OC)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH2:12].O=[C:13]1[CH:14]2[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19]2)[CH2:20][CH:21]1[CH2:22]3>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH:12][CH:13]1[CH:14]2[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19]2)[CH2:20][CH:21]1[C... | COc1cc(C)cc(OC)c1N.O=C1C2CC3CC(C2)CC1C3 | COc1cc(C)cc(OC)c1NC1C2CC3CC(C2)CC1C3 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Reductive amination with ketone | e29ccb3e9f939fd6ff91843a3b8403d58e3ca6cf6d34c1f56dbc1a49092d2877 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NC2C3CC4CC(C3)CC2C4)cc1 | O=[C;H0;D3;+0:1](-[C:2](-[C:3])-[C:4])-[C:5](-[C:6])-[C:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:3]-[C:2](-[C:4])-[CH;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:5](-[C:6])-[C:7] | 52 | [{"value": 52.0, "product": "C12C(C3CC(CC(C1)C3)C2)NC2=C(C=C(C=C2OC)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.1 g of 2,6-dimethoxy-4-methylaniline are dissolved in 10 ml of toluene, 0.5 ml of formic acid is then added to this solution and the mixture is heated to gentle reflux, under inert atmosphere, and 0.93 g of 2-adamantanone, dissolved in 10 ml of toluene, is added dropwise at this temperature. The reaction mixture is h... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | c1ccccc1.C1C2CC3CC1CC(C2)C3 | Other | C1(=CC=CC=C1)C | null | null | COc1cc(C)cc(OC)c1N.O=C1C2CC3CC(C2)CC1C3>C1(=CC=CC=C1)C>COc1cc(C)cc(OC)c1NC1C2CC3CC(C2)CC1C3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50d4e1528b5f4200af2c175551ee6a2e | COc1cc(C)cc(OC)c1NC=O>>CNc1c(OC)cc(C)cc1OC | O.[OH-].[Na+].O.C(=O)NC1=C(C=C(C=C1OC)C)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CNC1=C(C=C(C=C1OC)C)OC | O=[CH:1][NH:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([CH3:9])[cH:10][c:11]1[O:12][CH3:13]>>[CH3:1][NH:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([CH3:9])[cH:10][c:11]1[O:12][CH3:13] | COc1cc(C)cc(OC)c1NC=O | CNc1c(OC)cc(C)cc1OC | null | null | C(C)(=O)OCC.O1CCCC1 | Reduction | OtherReaction | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccccc1 | O=[CH;D2;+0:1]-[#7:2]-[c:3]>>[CH3;D1;+0:1]-[#7:2]-[c:3] | 85 | [{"value": 85.0, "product": "CNC1=C(C=C(C=C1OC)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 6 g of N-formyl-2,6-dimethoxy-4-methylaniline are suspended in 100 ml of tetrahydrofuran and then 33 ml of a 1M solution of lithium aluminium hydride in tetrahydrofuran are added dropwise under an inert atmosphere. The reaction mixture become homogeneous. The reaction mixture is left at room temperature for 2 hours and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1 | Other | C(C)(=O)OCC.O1CCCC1 | 0 | 2 | COc1cc(C)cc(OC)c1NC=O>C(C)(=O)OCC.O1CCCC1>CNc1c(OC)cc(C)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-008f672ce81f498d931758715cd6380b | CC(C)CC(=O)Cl.COc1cc(C)cc(OC)c1N>>COc1cc(C)cc(OC)c1NC(=O)CC(C)C | O.C(CC(C)C)(=O)Cl.COC1=C(N)C(=CC(=C1)C)OC.C(C)N(CC)CC>>COC1=C(C(=CC(=C1)C)OC)NC(CC(C)C)=O | Cl[C:13](=[O:14])[CH2:15][CH:16]([CH3:17])[CH3:18].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH2:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH:12][C:13](=[O:14])[CH2:15][CH:16]([CH3:17])[CH3:18] | CC(C)CC(=O)Cl.COc1cc(C)cc(OC)c1N | COc1cc(C)cc(OC)c1NC(=O)CC(C)C | null | null | C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 92 | [{"value": 92.0, "product": "COC1=C(C(=CC(=C1)C)OC)NC(CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 8.2 g of 2,6-dimethoxy-4-methylaniline are dissolved in 100 ml of diethyl ether at 0° C. under an inert atmosphere, 5.96 g of triethylamine are added to the reaction mixture and then 6.51 g of isovaleryl chloride are added dropwise, while maintaining the temperature at 0° C. The mixture is left at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(C)OCC | 0 | 0.5 | CC(C)CC(=O)Cl.COc1cc(C)cc(OC)c1N>C(C)OCC>COc1cc(C)cc(OC)c1NC(=O)CC(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9cb77feee68640b1aefc6e6668171bff | CC(C)(C)OC(=O)NCC(=O)O.COc1cc(C)cc(OC)c1N>>COc1cc(C)cc(OC)c1NC(=O)CNC(=O)OC(C)(C)C | Cl.COC1=C(N)C(=CC(=C1)C)OC.C(=O)(OC(C)(C)C)NCC(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.CN(C=O)C>>C(C)(C)(C)OC(=O)NCC(NC1=C(C=C(C=C1OC)C)OC)=O | O[C:13](=[O:14])[CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH2:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[NH:12][C:13](=[O:14])[CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:2... | CC(C)(C)OC(=O)NCC(=O)O.COc1cc(C)cc(OC)c1N | COc1cc(C)cc(OC)c1NC(=O)CNC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.C(C)(C)OC(C)C.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15] | 96 | [{"value": 96.0, "product": "C(C)(C)(C)OC(=O)NCC(NC1=C(C=C(C=C1OC)C)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 6.6 g of N-Boc-glycine and 15.6 g of BOP are successively added to 100 ml of dimethylformamide and then, at 0° C., 14 ml of triethylamine are added dropwise. The mixture is left for 20 minutes at 0° C. and 6.7 g of 2,6-dimethoxy-4-methylaniline hydrochloride are then added portionwise. The reaction mixture is left at r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(C)(=O)OCC.C(C)(C)OC(C)C.C(C)N(CC)CC | null | 0.333333 | CC(C)(C)OC(=O)NCC(=O)O.COc1cc(C)cc(OC)c1N>C(C)(=O)OCC.C(C)(C)OC(C)C.C(C)N(CC)CC>COc1cc(C)cc(OC)c1NC(=O)CNC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6a783fb8430848938491e8e735db7b30 | COC(=O)Cn1c(C(=O)O)cc2ccccc21.COc1cc(C)cc(OC)c1N(CCC(C)C)C(=O)CN>>COC(=O)Cn1c(C(=O)NCC(=O)N(CCC(C)C)c2c(OC)cc(C)cc2OC)cc2ccccc21 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC.COC(=O)CN1C(=CC2=CC=CC=C12)C(=O)O.Cl.COC1=C(C(=CC(=C1)C)OC)N(C(=O)CN)CCC(C)C.Cl.COC1=C(C(=CC(=C1)C)OC)N(C(=O)CN)CCC(C)C.O>>COC(CN1C(=CC2=CC=CC=C12)C(NCC(N(CCC(C)C)C1=C(C=C(C=C1OC)C)OC)=O)=O)=O | O[C:8]([c:7]1[n:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:37]2[c:32]([cH:31]1)[cH:33][cH:34][cH:35][cH:36]2)=[O:9].[NH2:10][CH2:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[c:20]1[c:21]([O:22][CH3:23])[cH:24][c:25]([CH3:26])[cH:27][c:28]1[O:29][CH3:30]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c:7]([C... | COC(=O)Cn1c(C(=O)O)cc2ccccc21.COc1cc(C)cc(OC)c1N(CCC(C)C)C(=O)CN | COC(=O)Cn1c(C(=O)NCC(=O)N(CCC(C)C)c2c(OC)cc(C)cc2OC)cc2ccccc21 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)c1cc2ccccc2[nH]1)Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5](-[C:6]-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10].[C:11]-[#7:12](-[c:13])-[C:14](=[O;D1;H0:15])-[C:16]-[NH2;D1;+0:17]>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7;a:5](:[c:10]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:17]-[C:16]-[C:14](=[O;D1;H0:15])-[#7:12](-[C:11])-[c:13]):... | 91 | [{"value": 91.0, "product": "COC(CN1C(=CC2=CC=CC=C12)C(NCC(N(CCC(C)C)C1=C(C=C(C=C1OC)C)OC)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 0.8 9 of [(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylamine hydrochloride (compound 100) is dissolved in 10 ml of dimethylformamide and 0.58 g of 1-(methoxycarbonylmethyl)-2-indolecarboxylic acid, 1.12 g of BOP and then, dropwise, 0.75 g of triethylamine are successively added to the reaction mixture at ro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cc2ccccc2[nH]1 | HO- | CN(C=O)C | null | 20 | COC(=O)Cn1c(C(=O)O)cc2ccccc21.COc1cc(C)cc(OC)c1N(CCC(C)C)C(=O)CN>CN(C=O)C>COC(=O)Cn1c(C(=O)NCC(=O)N(CCC(C)C)c2c(OC)cc(C)cc2OC)cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3f2f0bb549ae43f2a22173e022628003 | CCN(CC)CC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CN.COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CN>>COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CNC(=O)c1cc2ccccc2n1CCC#N | Cl.C1(CCCCC1)CN(C(=O)CN)C1=C(C=C(C=C1OC)C)OC.Cl.C1(CCCCC1)CN(C(=O)CN)C1=C(C=C(C=C1OC)C)OC.CN(C=O)C.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC.O>>C1(CCCCC1)CN(C(=O)CNC(=O)C=1N(C2=CC=CC=C2C1)CCC#N)C1=C(C=C(C=C1OC)C)OC | CC[N:34](CC)[CH2:35][CH3:36].CN(C)[P+](On1nn[c:33]2[c:28]1[cH:29][cH:30][cH:31][cH:32]2)(N(C)C)N(C)C.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[N:12]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[C:20](=[O:21])[CH2:22][NH2:23].COc1cc([CH3:27])cc(OC)c1N(CC1CCCCC1)[C:24](=[O:25])... | CCN(CC)CC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CN.COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CN | COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CNC(=O)c1cc2ccccc2n1CCC#N | null | null | C(#N)CCN1C(=CC2=CC=CC=C12)C(=O)O | Acylation | OtherReaction | 1daa8e78aa42744d303a7f45bccacd4e746d6a88c52dea0ae5c38dcad2af164f | 48c87d37cfd3265a624eb8d35435956a16bd2e3ba051cd4faef9d220de8e308d | O=C(NCC(=O)N(CC1CCCCC1)c1ccccc1)c1cc2ccccc2[nH]1 | C-C-[N;H0;D3;+0:1](-C-C)-[C:2]-[CH3;D1;+0:3].C-N(-C)-[P+](-O-n1:n:n:[c;H0;D3;+0:4]2:[c:5]:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2:1)(-N(-C)-C)-N(-C)-C.C-O-c1:c:c(-[CH3;D1;+0:10]):c:c(-O-C):c:1-N(-C-C1-C-C-C-C-C-1)-[C;H0;D3;+0:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-N.[C:14]-[#7:15](-[c:16])-[C:17](=[O;D1;H0:18])-[C:19]-[NH2;D1;+0... | 91 | [{"value": 91.0, "product": "C1(CCCCC1)CN(C(=O)CNC(=O)C=1N(C2=CC=CC=C2C1)CCC#N)C1=C(C=C(C=C1OC)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 1.5 g of [(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine hydrochloride (compound 113) are dissolved in 10 ml of dimethylformamide and 0.918 g of 1-(2-cyanoethyl)-2-indolecarboxylic acid, 1.95 g of BOP and then, dropwise, 1.28 g of triethylamine are then successively added. The reaction mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Primary amine.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine | Nitrile.Secondary amide | c1ccc2[nH]nnc2c1.c1ccccc1.C1CCCCC1 | c1cc2ccccc2[nH]1 | c1ccccc1.C1CCCCC1.c1cc2ccccc2[nH]1 | HO- | C(#N)CCN1C(=CC2=CC=CC=C12)C(=O)O | null | 3 | CCN(CC)CC.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CN.COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CN>C(#N)CCN1C(=CC2=CC=CC=C12)C(=O)O>COc1cc(C)cc(OC)c1N(CC1CCCCC1)C(=O)CNC(=O)c1cc2ccccc2n1CCC#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6b5216160b2e4600a21050c273b18922 | CCCCN(C(=O)CN)c1c(OC)cc(C)cc1OC.COC(=O)Cn1c(C(=O)O)cc2ccccc21>>CCCCN(C(=O)CNC(=O)c1cc2ccccc2n1CC(=O)OC)c1c(OC)cc(C)cc1OC | C(CCC)N(C(=O)CN)C1=C(C=C(C=C1OC)C)OC.COC(=O)CN1C(=CC2=CC=CC=C12)C(=O)O>>C(CCC)N(C(=O)CNC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC)C1=C(C=C(C=C1OC)C)OC | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH2:8][NH2:9])[c:26]1[c:27]([O:28][CH3:29])[cH:30][c:31]([CH3:32])[cH:33][c:34]1[O:35][CH3:36].O[C:10](=[O:11])[c:12]1[cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[n:20]1[CH2:21][C:22](=[O:23])[O:24][CH3:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH2:8][NH:9... | CCCCN(C(=O)CN)c1c(OC)cc(C)cc1OC.COC(=O)Cn1c(C(=O)O)cc2ccccc21 | CCCCN(C(=O)CNC(=O)c1cc2ccccc2n1CC(=O)OC)c1c(OC)cc(C)cc1OC | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)c1cc2ccccc2[nH]1)Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5](-[C:6]-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10].[C:11]-[#7:12](-[c:13])-[C:14](=[O;D1;H0:15])-[C:16]-[NH2;D1;+0:17]>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7;a:5](:[c:10]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:17]-[C:16]-[C:14](=[O;D1;H0:15])-[#7:12](-[C:11])-[c:13]):... | 90 | [{"value": 90.0, "product": "C(CCC)N(C(=O)CNC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC)C1=C(C=C(C=C1OC)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This product is prepared according to the process described in EXAMPLE 1 from [butyl(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine and 1-(methoxycarbonylmethyl)-2-indolecarboxylic acid; M.p.=139° C.; Yield: 90%.
Conditions: See reaction.notes.procedure_details.
Workup: This product is prepared | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | HO- | null | null | null | CCCCN(C(=O)CN)c1c(OC)cc(C)cc1OC.COC(=O)Cn1c(C(=O)O)cc2ccccc21>>CCCCN(C(=O)CNC(=O)c1cc2ccccc2n1CC(=O)OC)c1c(OC)cc(C)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29290da4f651485f9a89caa1ac100820 | COC(=O)Cn1c(C(=O)N[C@H](CCCCNC(=O)OCc2ccccc2)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21>>COC(=O)Cn1c(C(=O)N[C@H](CCCCN)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21 | COC1=C(C(=CC(=C1)C)OC)CCCCCNC(=O)[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)NC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC>>COC1=C(C(=CC(=C1)C)OC)CCCCCNC(=O)[C@@H](CCCCN)NC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC | O=C(OCc1ccccc1)[NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]([NH:10][C:8]([c:7]1[n:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:42]2[c:37]([cH:36]1)[cH:38][cH:39][cH:40][cH:41]2)=[O:9])[C:17](=[O:18])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][c:25]1[c:26]([O:27][CH3:28])[cH:29][c:30]([CH3:31])[cH:32][c:33]1[O:34][CH3... | COC(=O)Cn1c(C(=O)N[C@H](CCCCNC(=O)OCc2ccccc2)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21 | COC(=O)Cn1c(C(=O)N[C@H](CCCCN)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(CNC(=O)c1cc2ccccc2[nH]1)NCCCCCc1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 85 | [{"value": 85.0, "product": "COC1=C(C(=CC(=C1)C)OC)CCCCCNC(=O)[C@@H](CCCCN)NC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 5.6 g of methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(benzyloxycarbonylamino)pentyl}carbamoyl]indol-1-yl}acetate (EXAMPLE 66) are dissolved in 170 ml of methanol and 0.56 g of 10% Pd/C is added thereto. Hydrogenation is carried out under a pressure of 3 bar and the reaction mixture is left at ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1cc2ccccc2[nH]1 | HO- | [Pd].CO | null | 18 | COC(=O)Cn1c(C(=O)N[C@H](CCCCNC(=O)OCc2ccccc2)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21>[Pd].CO>COC(=O)Cn1c(C(=O)N[C@H](CCCCN)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-92a29c6b2fb348a4acb80711b9b5d5dc | COC(=O)Cn1c(C(=O)N[C@H](CCCCN)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21.O=C(O)C=Cc1ccccc1>>COC(=O)Cn1c(C(=O)N[C@H](CCCCNC(=O)C=Cc2ccccc2)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21 | C(C)N1CCOCC1.COC1=C(C(=CC(=C1)C)OC)CCCCCNC(=O)[C@@H](CCCCN)NC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C=CC1=CC=CC=C1)(=O)O>>COC1=C(C(=CC(=C1)C)OC)CCCCCNC(=O)[C@@H](CCCCNC(C=CC1=CC=CC=C1)=O)NC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c:7]([C:8](=[O:9])[NH:10][C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[C:27](=[O:28])[NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][c:35]2[c:36]([O:37][CH3:38])[cH:39][c:40]([CH3:41])[cH:42][c:43]2[O:44][CH3:45])[cH:46][c:47]2[cH:48][cH:49][cH:50][cH:51][c:52]12.O[C:17](=[O:... | COC(=O)Cn1c(C(=O)N[C@H](CCCCN)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21.O=C(O)C=Cc1ccccc1 | COC(=O)Cn1c(C(=O)N[C@H](CCCCNC(=O)C=Cc2ccccc2)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21 | null | null | CN(C=O)C.O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccccc1)NCCCC[C@@H](NC(=O)c1cc2ccccc2[nH]1)C(=O)NCCCCCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5] | null | [] | -5 | CELSIUS | 18 | HOUR | 0.87 g of methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-aminopentyl}carbamoyl]indol-1-yl}acetate, 0.645 g of BOP and 0.23 g of cinnamic acid are successively added to 30 ml of dimethylformamide. After cooling to -5° C., 0.26 g of N-ethylmorpholine is added under an inert atmosphere and the react... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HO- | CN(C=O)C.O.C(C)(=O)OCC | -5 | 18 | COC(=O)Cn1c(C(=O)N[C@H](CCCCN)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21.O=C(O)C=Cc1ccccc1>CN(C=O)C.O.C(C)(=O)OCC>COC(=O)Cn1c(C(=O)N[C@H](CCCCNC(=O)C=Cc2ccccc2)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f6bb4c0c2bb1418fb1a1edbd930b2162 | C1CCNCC1.C1COCCN1.Cl.O=C(Cl)c1cc(Cl)ccc1Cl.c1ccc(Oc2ccccc2)cc1>>O=C(c1cc(Cl)ccc1Cl)N1CCCCC1.O=C(c1cc(Cl)ccc1Cl)N1CCOCC1 | N1CCOCC1.N1CCCCC1.Cl.ClC1=C(C(=O)Cl)C=C(C=C1)Cl.C1(=CC=CC=C1)OC.C1(=CC=CC=C1)OC1=CC=CC=C1>>ClC1=C(C(=O)N2CCOCC2)C=C(C=C1)Cl.ClC1=C(C(=O)N2CCCCC2)C=C(C=C1)Cl | [NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1.[NH:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1.[ClH:6].[Cl:10][C:18](=[O:17])[c:19]1[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]1[Cl:26].c1ccc(O[c:3]2[cH:4][cH:5][cH:7][cH:8][cH:9]2)cc1>>[O:1]=[C:2]([c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[Cl:10])[N:11]1[CH2:12][CH2:1... | C1CCNCC1.C1COCCN1.Cl.O=C(Cl)c1cc(Cl)ccc1Cl.c1ccc(Oc2ccccc2)cc1 | O=C(c1cc(Cl)ccc1Cl)N1CCCCC1.O=C(c1cc(Cl)ccc1Cl)N1CCOCC1 | null | [Cl-].[Al+3].[Cl-].[Cl-] | C1(=CC=CC=C1)C.C1=CC=CC=C1.N1=CC=CC=C1 | Acylation | OtherReaction | 4cc4c33ad0aef4ca318ac0eedbfdd926dad54cb2db9ce9823faf1472c5d58b83 | b6b0c7439ced26a20194ee7fb1e1611e093c063c708b93f205113aa5a58e7e2f | O=C(c1ccccc1)N1CCCCC1.O=C(c1ccccc1)N1CCOCC1 | O(-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1)-c1:c:c:c:c:c:1.[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1.[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17].[Cl;H0;D1;+0:18]-[C;H0;D3;+0:19](=[O;D1;H0:20])-[c:21](:[c:22]):[c:23].[ClH;D0;+0:24]>>[C:13]-[C:14]-[N;H0;D3;+0:15](-[C:25](=[O;D1;H0:26])-[c;H0;D... | null | [] | null | null | null | null | A wide variety of 2,5-dichlorobenzoyl-containing compounds (e.g. 2,5-dichlorobenzophenones and 2,5-dichlorobenzamides) can be readily prepared from 2,5-dichlorobenzoylchloride. Pure 2,5-dichlorobenzoylchloride is obtained by vacuum distillation of the mixture obtained from the reaction of commercially available 2,5-dic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine.Secondary amine | Aromatic halide.Aromatic halide.Tertiary amide.Tertiary amide | C1CCNCC1.C1COCCN1.c1ccccc1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.C1COCC[NH]1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.C1COCC[NH]1 | HO- | [Cl-].[Al+3].[Cl-].[Cl-].C1(=CC=CC=C1)C.C1=CC=CC=C1.N1=CC=CC=C1 | null | null | C1CCNCC1.C1COCCN1.Cl.O=C(Cl)c1cc(Cl)ccc1Cl.c1ccc(Oc2ccccc2)cc1>[Cl-].[Al+3].[Cl-].[Cl-].C1(=CC=CC=C1)C.C1=CC=CC=C1.N1=CC=CC=C1>O=C(c1cc(Cl)ccc1Cl)N1CCCCC1.O=C(c1cc(Cl)ccc1Cl)N1CCOCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4ed142657f3d431e82ca203fc86540a6 | Cc1cccc(C(=O)Cl)c1.Clc1ccc(Cl)cc1>>Cc1cccc(C(=O)c2cc(Cl)ccc2Cl)c1 | Cl.C1(=CC(=CC=C1)C(=O)Cl)C.ClC1=CC=C(C=C1)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>ClC1=C(C(=O)C2=CC(=CC=C2)C)C=C(C=C1)Cl | Cl[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:17]1)=[O:8].[cH:9]1[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]1[Cl:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([Cl:12])[cH:13][cH:14][c:15]2[Cl:16])[cH:17]1 | Cc1cccc(C(=O)Cl)c1.Clc1ccc(Cl)cc1 | Cc1cccc(C(=O)c2cc(Cl)ccc2Cl)c1 | null | null | CCOCC | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[Cl;D1;H0:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[Cl;D1;H0:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:10]:[c:11] | 53 | [{"value": 53.0, "product": "ClC1=C(C(=O)C2=CC(=CC=C2)C)C=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.4, "product": "ClC1=C(C(=O)C2=CC(=CC=C2)C)C=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A mixture of m-toluoyl chloride (22 g, 0.17 mol) and 1,4-dichlorobenzene (120 g, 0.82 mol) was heated to 100° C. in a flask. Aluminum chloride (60 g, 0.45 mol) was added in one portion. Hydrogen chloride started to evolve from the solution. The mixture was heated to 170° C. in 30 min. and stirred at this temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | CCOCC | 100 | 3 | Cc1cccc(C(=O)Cl)c1.Clc1ccc(Cl)cc1>CCOCC>Cc1cccc(C(=O)c2cc(Cl)ccc2Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9d4147d3edea46ffb150787b3152cac8 | Cc1ccc(Cl)cc1C.O=C(Cl)C(=O)Cl.O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O>>Cc1cc(Cl)c(C(=O)c2cc(C)c(C)cc2Cl)cc1C | ClC=1C=C(C(=CC1)C)C.C1=CC2=C(C=C1C(=O)C3=CC4=C(C=C3)C(=O)OC4=O)C(=O)OC2=O.C(C(=O)Cl)(=O)Cl>>ClC1=C(C(=O)C2=C(C=C(C(=C2)C)C)Cl)C=C(C(=C1)C)C | [CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:18][c:19]1[CH3:20].O=C(Cl)C(=O)[Cl:17].O=C1O[C:12](=O)c2ccc([C:7](=[O:8])[c:9]3[cH:10][cH:11][c:13]4[c:15]([cH:16]3)C(=O)O[C:14]4=O)cc21>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([CH3:12])[c:13]([CH3:14])[cH:15][c:16]2[Cl:17])[cH:18][c:19]1[CH3:20] | Cc1ccc(Cl)cc1C.O=C(Cl)C(=O)Cl.O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O | Cc1cc(Cl)c(C(=O)c2cc(C)c(C)cc2Cl)cc1C | null | null | null | C-C Coupling | OtherReaction | d785ce73f8fa54e79ecd3826562b6989a8f95f0fe4e0d0fb90cb0f95b39142cb | 70e985d43b0076a7012602e4c9840d5fd72f3ec2d002ae00e9d4230eae0d9a16 | O=C(c1ccccc1)c1ccccc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O=C1-O-[C;H0;D3;+0:2](=O)-[c:3]2:[cH;D2;+0:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-c3:c:c:c4:c(:c:3)-C(=O)-O-[C;H0;D3;+0:9]-4=O):[cH;D2;+0:10]:[c;H0;D3;+0:11]:2-1.[Cl;D1;H0:12]-[c:13](:[c:14]):[cH;D2;+0:15]:[c:16]:[c:17]>>[CH3;D1;+0:9]-[c;H0;D3;+0:4]1:[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;... | null | [] | null | null | null | null | Specific benzophenonetetracarboxylic dianhydrides preferred in this invention are readily available from commercial sources or synthesis. For instance, 3,3',4,4'-benzophenonetetracarboxylic dianhydride (D1) is available from Aldrich Chemical Co., Inc. (1001 W. St. Paul Ave., Milwaukee, Wis. 53233). 2,2'-Dichloro-4,4',5... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Anhydride.Anhydride.Ketone.Ester.Ester.Ester.Ester | Aromatic halide.Ketone | c1ccccc1.c1ccc2c(c1)COC2.c1ccc2c(c1)COC2 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | null | Cc1ccc(Cl)cc1C.O=C(Cl)C(=O)Cl.O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O>>Cc1cc(Cl)c(C(=O)c2cc(C)c(C)cc2Cl)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ef6ff2ed718b4bfdb1e48398ec37733b | CCCCCCCCCCCCCCCCCCBr.O=[N+]([O-])c1ccc(O)c([N+](=O)[O-])c1>>CCCCCCCCCCCCCCCCCCOc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | Cl.[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])O.C(CCCCCCCCCCCCCCCCC)Br.C([O-])([O-])=O.[Na+].[Na+]>>C(CCCCCCCCCCCCCCCCC)OC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-] | Br[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:19][c:20]1[cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27][c:28]1[N+:29](=[O:30])[O-:31]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:... | CCCCCCCCCCCCCCCCCCBr.O=[N+]([O-])c1ccc(O)c([N+](=O)[O-])c1 | CCCCCCCCCCCCCCCCCCOc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 79.1 | [{"value": 79.0, "product": "C(CCCCCCCCCCCCCCCCC)OC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "C(CCCCCCCCCCCCCCCCC)OC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 2,4-dinitrophenol (85 wt %, 6.72 g, 31 mmol), octadecyl bromide (20.7 g, 62 mmol), sodium carbonate (6.57 g, 62 mmol) and dimethylformamide (31 mL) was heated to 100° C. under a nitrogen atmosphere for 22 h. The cooled mixture was diluted with water (200 mL), acidified with 10N hydrochloric acid (50 mL) an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C.O | 100 | null | CCCCCCCCCCCCCCCCCCBr.O=[N+]([O-])c1ccc(O)c([N+](=O)[O-])c1>CN(C=O)C.O>CCCCCCCCCCCCCCCCCCOc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5971a4af9d3748bbb69b7eae2a504585 | CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC.O=[N+]([O-])c1ccc(Cl)c([N+](=O)[O-])c1>>CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | ClC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-].C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCCCCCCCCCCCC)NCCCCCCCCCCCCCCCCCC.CN(C=O)C>>C(CCCCCCCCCCCCCCCCC)N(C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])CCCCCCCCCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].Cl[c:38]1[cH:39][cH:40][c:41]([N+... | CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC.O=[N+]([O-])c1ccc(Cl)c([N+](=O)[O-])c1 | CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11]):[c:2]:[c:3] | 87.2 | [{"value": 87.0, "product": "C(CCCCCCCCCCCCCCCCC)N(C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])CCCCCCCCCCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "C(CCCCCCCCCCCCCCCCC)N(C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])CCCCCCCCCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | A mixture of 1-chloro-2,4-dinitrobenzene (Aldrich, 2.02 g, 10 mmol), sodium carbonate (1.27 g, 12 mmol), dioctadecylamine (Pfaltz & Bauer, 6.26 g, 12 mmol) and dry dimethylformamide (10 mL) was heated to 80°-90° C. under a nitrogen atmosphere for 1 h. The cooled mixture was diluted with water and extracted with ether. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O | null | null | CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC.O=[N+]([O-])c1ccc(Cl)c([N+](=O)[O-])c1>O>CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c7f13666e73841749111f9cf0068f690 | Nc1ccc([N+](=O)[O-])cc1C(F)(F)F.Nc1cccc(C(F)(F)F)c1>>Nc1ccc(N=Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)cc1 | FC(C1=C(C=CC(=C1)[N+](=O)[O-])N)(F)F.FC(C=1C=C(C=CC1)N)(F)F.C([O-])([O-])=O.[K+].[K+].N(=O)[O-].[Na+]>>FC(C=1C=C(C=CC1[N+](=O)[O-])N=NC1=CC=C(C=C1)N)(F)F | [NH2:7][c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:20]1[C:16]([F:17])([F:18])[F:19].FC(F)(F)[c:21]1[cH:5][cH:4][cH:3][c:2]([NH2:1])[cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[N:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]2)[cH:21][cH:22]1 | Nc1ccc([N+](=O)[O-])cc1C(F)(F)F.Nc1cccc(C(F)(F)F)c1 | Nc1ccc(N=Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)cc1 | null | null | Cl | C-C Coupling | OtherReaction | 18f98b7f0c9cf3db84b5cb8b114e8fbf5af9b2166f9d2ff0a9a20eed2d1192b6 | 7eecec1bc902af1594125c1c8ce3bf240905e0c7e39309c2fd068a8de44adb2a | c1ccc(N=Nc2ccccc2)cc1 | F-C(-F)(-F)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.[#7;+:7]-[c:8]1:[c:9]:[c:10]:[c:11](-[NH2;D1;+0:12]):[c;H0;D3;+0:13](-[C;H0;D4;+0:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[F;D1;H0:17]):[cH;D2;+0:18]:1>>[#7;+:7]-[c:8]1:[c:9]:[c:10]:[c:11](-[N;H0;D2;+0:12]=[#7:19]-[c;H0;D3;+0:6]2:[c:5]:[c:4]:[c:3]:[c:2]:[cH;D... | null | [] | null | null | 0.5 | HOUR | 2-Trifluoromethyl-4-nitro-benzeneamine (4.92 g, 23.8 mmol) slurried in 5N hydrochloric acid (15.8 mL) and ice (16 g) was diazotized with 2M sodium nitrite (12.6 mL, 25 mmol) at 0°-5° C., followed by coupling with 3-trifluoromethylbenzeneamine (5.0 g, 31 mmol) in 5N hydrochloric acid (8 mL) at 0°-5° C. The mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Trifluoro group.Primary amine | Trifluoro group.Diazene | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HF | Cl | null | 0.5 | Nc1ccc([N+](=O)[O-])cc1C(F)(F)F.Nc1cccc(C(F)(F)F)c1>Cl>Nc1ccc(N=Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f5393e1cc6454a74b09650aa083904a0 | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.CC(C)(C)c1cc(CC2SC(=S)NC2=O)cc(C(C)(C)C)c1O>>CC(C)c1cc(C=C2SCN(C)C2=O)cc(C(C)C)c1O | C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C.S1C(=S)NC(=O)C1.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NCS1)=O.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NCS1)=O.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC1C(NCS1)=O.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC1C(NCS1)=O.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC... | C[C:2]([CH3:1])([CH3:3])[c:4]1[cH:5][c:6]([CH:7]=[C:8]2[S:9][CH2:10][NH:11][C:13]2=[O:14])[cH:15][c:16]([C:17](C)([CH3:18])[CH3:19])[c:20]1[OH:21].CC(C)(C)c1cc(CC2SC(=S)N[C:12]2=O)cc(C(C)(C)C)c1O>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]=[C:8]2[S:9][CH2:10][N:11]([CH3:12])[C:13]2=[O:14])[cH:15][c:16]([CH:17]([CH3... | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.CC(C)(C)c1cc(CC2SC(=S)NC2=O)cc(C(C)(C)C)c1O | CC(C)c1cc(C=C2SCN(C)C2=O)cc(C(C)C)c1O | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 2254c6efd04fa4d0a0952eb05922d7e69eadca72a16ee189b368085006e27388 | 623931a4a70a5aa7e222cd098e3452a845c930a29a7a3ce88c269860d1e71388 | O=C1NCSC1=Cc1ccccc1 | C-C(-C)(-C)-c1:c:c(-C-C2-S-C(=S)-N-[C;H0;D3;+0:1]-2=O):c:c(-C(-C)(-C)-C):c:1-O.C-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5]1:[c:6]:[c:7](-[C:8]=[C:9]2-[#16:10]-[C:11]-[NH;D2;+0:12]-[C:13]-2=[O;D1;H0:14]):[c:15]:[c:16](-[C;H0;D4;+0:17](-C)(-[C;D1;H3:18])-[C;D1;H3:19]):[c:20]:1>>[C;D1;H3:3]-[CH;D3;+0:2](-[C;D1;H3:4... | null | [] | null | null | null | null | The aryl-substituted rhodanine derivatives of formula I are either known in the art or may be prepared by any of a number of well-known procedures. For example, Teuber et al., Leibigs Ann. Chem., 757 (1978) disclose 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone (referred to in the ... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Secondary amide.Aromatic alcohol.Monosulfide | Tertiary amide | C1CSCN1.c1ccccc1.C1CSCN1 | C1CSC[NH]1 | c1ccccc1.C1CSC[NH]1 | Other | C(C)(=O)O | null | null | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.CC(C)(C)c1cc(CC2SC(=S)NC2=O)cc(C(C)(C)C)c1O>C(C)(=O)O>CC(C)c1cc(C=C2SCN(C)C2=O)cc(C(C)C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c6e9632cd19641829385bd2d3cca13fe | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=S)N1>>CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O | C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C.S1C(=S)NC(=O)C1.O.C(C)O>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O | O=[CH:8][c:7]1[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[c:22]([OH:23])[c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:16]1.[CH2:9]1[S:10][C:11](=[S:12])[NH:13][C:14]1=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[C:9]2[S:10][C:11](=[S:12])[NH:13][C:14]2=[O:15])[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[... | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=S)N1 | CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O | null | null | C(C)(=O)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=S)SC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Under a nitrogen atmosphere, 117.2 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde, 66.6 g of rhodanine, and 143.5 g of fused sodium acetate were heated at reflux in 2500 ml of glacial acetic acid. After heating for 23 hours, the reaction mixture was cooled and poured into a mixture of 1 liter of ethanol and 1 liter of ic... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1ccccc1.C1CSCN1 | HO- | C(C)(=O)O | null | null | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.O=C1CSC(=S)N1>C(C)(=O)O>CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72199bbc97064ed2941895c9e2129ccc | CC(C)(C)c1cc(C=C2NC(=O)CS2)cc(C(C)(C)C)c1O.CSCCCl>>CSCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | [H-].[Na+].CSCCCl.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1SCC(N1)=O.CN(C)C=O>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCSC)=O | [NH:5]1[C:8](=[CH:9][c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([OH:18])[c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24]2)[S:7][CH2:6][C:25]1=[O:26].Cl[CH2:4][CH2:3][S:2][CH3:1]>>[CH3:1][S:2][CH2:3][CH2:4][N:5]1[CH2:6][S:7][C:8](=[CH:9][c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([... | CC(C)(C)c1cc(C=C2NC(=O)CS2)cc(C(C)(C)C)c1O.CSCCCl | CSCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | null | null | Cl.C(C)OCC | C-C Coupling | OtherReaction | 7fc90906fcdd4898db86cc09e2f1b4cedb2a6ece49dd2317291e997ed31a0ef5 | 41a805bcc08a9b877e6774d1f0216c1d35b872f237aa67e0e00e43c063cb9134 | O=C1NCSC1=Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-[CH2;D2;+0:6]-[#16:7]-[C;H0;D3;+0:8](=[C:9]-[c:10])-[NH;D2;+0:11]-1>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[CH2;D2;+0:6]-[#16:7]-[C;H0;D3;+0:8](=[C:9]-[c:10])-[C;H0;D3;+0:5]-1=[O;D1;H0:4] | null | [] | 100 | CELSIUS | 6 | DAY | 26.7 g of 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene-4-thiazolidinone (i.e., the compound of Example 2) was dissolved in 418 ml of DMF to which was added 3.34 g of a 60% sodium hydride dispersion. The resultant mixture was stirred at 100° C. under an argon atmosphere. To this was added 8.33 ml of methylth... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary halide.Secondary amide.Monosulfide | Tertiary amide.Monosulfide | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | HCl | Cl.C(C)OCC | 100 | 144 | CC(C)(C)c1cc(C=C2NC(=O)CS2)cc(C(C)(C)C)c1O.CSCCCl>Cl.C(C)OCC>CSCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c9be2f1c1414538a509efd6fbcd16ff | CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O>>CC(C)(C)c1cc(CC2SC(=S)NC2=O)cc(C(C)(C)C)c1O | CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O.CC=1NC(=C(CC1C(=O)OCC)C(=O)OCC)C.C(C)(=O)OCC>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC1C(NC(S1)=S)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[C:9]2[S:10][C:11](=[S:12])[NH:13][C:14]2=[O:15])[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]1[OH:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH2:8][CH:9]2[S:10][C:11](=[S:12])[NH:13][C:14]2=[O:15])[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:2... | CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O | CC(C)(C)c1cc(CC2SC(=S)NC2=O)cc(C(C)(C)C)c1O | null | null | C1(=CC=CC=C1)C | Reduction | Hydrogenation (double to single) | 5287357a9ceae46aa07f85d3bac2070fe5bb40eaa8eb1baec18cbe42a25e8909 | 229264280d760663074461f898bce2a68d1dd7a993ad956085f2c6522e0edd11 | O=C1NC(=S)SC1Cc1ccccc1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[S;D1;H0:5])-[#16:6]-[C;H0;D3;+0:7]-1=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[S;D1;H0:5])-[#16:6]-[CH;D3;+0:7]-1-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11] | 56.9 | [{"value": 56.9, "product": "CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC1C(NC(S1)=S)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under a nitrogen atmosphere, 13.98 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone, 13.17 g of diethyl 2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate and 600 ml of toluene were stirred to effect solution. Forty grams of silica gel 60 (finer than 230 mesh) previously dried in... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1ccccc1.C1CSCN1 | null | C1(=CC=CC=C1)C | null | null | CC(C)(C)c1cc(C=C2SC(=S)NC2=O)cc(C(C)(C)C)c1O>C1(=CC=CC=C1)C>CC(C)(C)c1cc(CC2SC(=S)NC2=O)cc(C(C)(C)C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b9e3c51570840348769e6a40ddaa89d | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.CN1C(=O)CSC1=S>>CN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S | C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C.CN1C(SCC1=O)=S>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)C)=O | O=[CH:6][c:7]1[cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]([OH:15])[c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]1.[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][S:22][C:23]1=[S:24]>>[CH3:1][N:2]1[C:3](=[O:4])[C:5](=[CH:6][c:7]2[cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]([OH:15])[c:16]([C:17]([CH3:18])([CH3:19... | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.CN1C(=O)CSC1=S | CN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S | null | null | null | C-C Coupling | Aldol condensation | 315c5abda6f5c04d5321614cd32fbf107303aab42297b04d1819d58208c94487 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=S)SC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7:6]1-[C:7](=[S;D1;H0:8])-[#16:9]-[CH2;D2;+0:10]-[C:11]-1=[O;D1;H0:12]>>[C;D1;H3:5]-[#7:6]1-[C:7](=[S;D1;H0:8])-[#16:9]-[C;H0;D3;+0:10](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11]-1=[O;D1;H0:12] | 76 | [{"value": 76.0, "product": "CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared in 76% yield from 3,5-di-tert-butyl-4-hydroxybenzaldehyde and N-methylrhodanine following the procedure of Example 1, m.p. >230° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSC[NH]1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | HO- | null | null | null | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O.CN1C(=O)CSC1=S>>CN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-867855b5cbc343afbf6e7d8206f20441 | CN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S>>CN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | C(CCC)[SnH](CCCC)CCCC.N(=NC(C#N)(C)C)C(C#N)(C)C.O.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)C)=O>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)C)=O | S=[C:3]1[N:2]([CH3:1])[C:22](=[O:23])[C:5](=[CH:6][c:7]2[cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]([OH:15])[c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]2)[S:4]1>>[CH3:1][N:2]1[CH2:3][S:4][C:5](=[CH:6][c:7]2[cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]([OH:15])[c:16]([C:17]([CH3:18])([CH3:19])[CH3... | CN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S | CN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | 3075aa4a480315be93c6069c30839bbd13f7a2020ecf519735ecee8afa07f2e9 | 0f72a6a79dcf7806020691b0c331ca1668d57eb95f4b08c405899f23029b31ef | O=C1NCSC1=Cc1ccccc1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3](=[C:4]-[c:5])-[C:6](=[O;D1;H0:7])-[#7:8]-1-[C;D1;H3:9]>>[C;D1;H3:9]-[#7:8]1-[CH2;D2;+0:1]-[#16:2]-[C:3](=[C:4]-[c:5])-[C:6]-1=[O;D1;H0:7] | 71 | [{"value": 71.0, "product": "CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared in 71% yield from 10.31 g of the thione of Example 9 upon heating with 38.15 ml of tri-n-butyl tin hydride and 1.16 g of azobisisobutyronitrile (AIBN) in 142 ml of toluene at reflux temperature for one hour. The product was isolated by adding water to the cooled reaction mixture, separat... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide | Monosulfide | C1CSC[NH]1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | CN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S>C1(=CC=CC=C1)C>CN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-99da04be27454cd9bffd7d2ff5f26253 | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.CCI>>CCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | Cl.C(C)I.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NCS1)=O.[H-].[Na+]>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CC)=O | [NH:3]1[CH2:4][S:5][C:6](=[CH:7][c:8]2[cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([OH:16])[c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]2)[C:23]1=[O:24].I[CH2:2][CH3:1]>>[CH3:1][CH2:2][N:3]1[CH2:4][S:5][C:6](=[CH:7][c:8]2[cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([OH:16])[c:17]([C:18]([CH3:19]... | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.CCI | CCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | null | null | O.O1CCCC1.C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 431f5f5bf6f9cf449d2e55b8c9492e72e15ac1fd928cbbb6a7e09ce10662fe6f | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1NCSC1=Cc1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[C:4]1-[NH;D2;+0:5]-[C:6]-[#16:7]-[C:8]-1=[C:9]-[c:10]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5]1-[C:6]-[#16:7]-[C:8](=[C:9]-[c:10])-[C:4]-1=[O;D1;H0:3] | null | [] | null | null | 2 | DAY | To a solution of 9.58 g of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]methylene]-4-thiazolidinone in 150 ml of tetrahydrofuran were added 1.20 g of a 60% dispersion of sodium hydride in mineral oil. After gas evolution ceased, 2.4 ml of ethyl iodide were added and the reaction mixture was stirred for two days unde... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | HI | O.O1CCCC1.C(C)OCC | null | 48 | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.CCI>O.O1CCCC1.C(C)OCC>CCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58ca17b5dd0d413781b61e87bea26a57 | CCOCC.NCCO.S=C=S>>O=C1CSC(=S)N1CCO | C(=S)=S.C(C)OCC.C(O)CN>>OCCN1C(SCC1=O)=S | CC[O:1][CH2:2][CH3:3].[NH2:7][CH2:8][CH2:9][OH:10].[S:4]=[C:5]=[S:6]>>[O:1]=[C:2]1[CH2:3][S:4][C:5](=[S:6])[N:7]1[CH2:8][CH2:9][OH:10] | CCOCC.NCCO.S=C=S | O=C1CSC(=S)N1CCO | null | null | C(C)O | Acylation | OtherReaction | 8e9a9f9b55f68f5203b4b9892426018f212fb1f27ac89e84cce43a279f00e0d6 | 13db5cf9dd1fff0115257c15afd0219453b1ca2807e072b818e8ecb9af0c0645 | O=C1CSC(=S)N1 | C-C-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[CH3;D1;+0:3].[C:4]-[C:5]-[NH2;D1;+0:6].[S;D1;H0:7]=[C;H0;D2;+0:8]=[S;H0;D1;+0:9]>>[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[CH2;D2;+0:3]-[S;H0;D2;+0:9]-[C;H0;D3;+0:8]-1=[S;D1;H0:7] | null | [] | -5 | CELSIUS | 75 | MINUTE | Sixty milliliters of carbon disulfide were added to 200 ml of diethyl ether. The solution was chilled to -5° C. and slowly added to a solution of 138 ml of ethanolamine in 250 ml of ethanol. After holding the mixture at ambient temperature for 16 hours, the resulting top layer was decanted and the residual oil washed t... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Thioamide.Tertiary amide.Monosulfide | null | C1CSC[NH]1 | C1CSC[NH]1 | Other | C(C)O | -5 | 1.25 | CCOCC.NCCO.S=C=S>C(C)O>O=C1CSC(=S)N1CCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3db3491868884e35b394ce60e7488946 | CC(=O)OCCN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S>>CC(=O)OCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)CCOC(C)=O)=O.C(CCC)[SnH](CCCC)CCCC.CC(C)(C#N)N=NC(C)(C)C#N>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCOC(C)=O)=O | S=[C:8]1[N:7]([CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3])[C:27](=[O:28])[C:10](=[CH:11][c:12]2[cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]([OH:20])[c:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26]2)[S:9]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][N:7]1[CH2:8][S:9][C:10](=[CH:11][c:12]2[cH:13][c:14]([C:15]([CH3:1... | CC(=O)OCCN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S | CC(=O)OCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | 3075aa4a480315be93c6069c30839bbd13f7a2020ecf519735ecee8afa07f2e9 | 0f72a6a79dcf7806020691b0c331ca1668d57eb95f4b08c405899f23029b31ef | O=C1NCSC1=Cc1ccccc1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3](=[C:4]-[c:5])-[C:6](=[O;D1;H0:7])-[#7:8]-1-[C:9]>>[C:9]-[#7:8]1-[CH2;D2;+0:1]-[#16:2]-[C:3](=[C:4]-[c:5])-[C:6]-1=[O;D1;H0:7] | 59.7 | [{"value": 59.7, "product": "CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCOC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Under a nitrogen atmosphere, 82.2 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy) ethyl]-2-thioxo-4-thiazolidinone in 950 ml of toluene was heated to 65° C. Tri-n-butyl tin hydride (219.7 g) and AIBN (4.65 g) were added and the solution heated at reflux temperature for an additional 10 m... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide | Monosulfide | C1CSC[NH]1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | 8 | CC(=O)OCCN1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S>C1(=CC=CC=C1)C>CC(=O)OCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dab83e5f8e4f453e9acc6425fd301ce5 | CC(=O)OCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O>>CC(C)(C)c1cc(C=C2SCN(CCO)C2=O)cc(C(C)(C)C)c1O | CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCOC(C)=O)=O.[OH-].[NH4+]>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCO)=O | CC(=O)[O:15][CH2:14][CH2:13][N:12]1[CH2:11][S:10][C:9](=[CH:8][c:7]2[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[c:24]([OH:25])[c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:18]2)[C:16]1=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[C:9]2[S:10][CH2:11][N:12]([CH2:13][CH2:14][OH:15])[C:16]2=[O:17])[cH:18... | CC(=O)OCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | CC(C)(C)c1cc(C=C2SCN(CCO)C2=O)cc(C(C)(C)C)c1O | null | null | C(C)#N | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C1NCSC1=Cc1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 46.7 | [{"value": 46.7, "product": "CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | HOUR | A solution of 85.2 g of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinone from Example 26 in 1.5 l of acetonitrile was treated with 1 liter of concentrated ammonium hydroxide. The reaction mixture was allowed to stand for approximately 90 hours at room temperature. The s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.C1CSC[NH]1 | HO- | C(C)#N | null | 90 | CC(=O)OCCN1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O>C(C)#N>CC(C)(C)c1cc(C=C2SCN(CCO)C2=O)cc(C(C)(C)C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20eb6cc14ae4481ca9a1fde22cf62941 | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.N#CCBr>>CC(C)(C)c1cc(C=C2SCN(CC#N)C2=O)cc(C(C)(C)C)c1O | CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NCS1)=O.BrCC#N.[H-].[Na+]>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CC#N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[C:9]2[S:10][CH2:11][NH:12][C:16]2=[O:17])[cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]1[OH:25].Br[CH2:13][C:14]#[N:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[C:9]2[S:10][CH2:11][N:12]([CH2:13][C:14]#[N:15])[C:16]2=[O:17])[cH:18][c:19]([... | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.N#CCBr | CC(C)(C)c1cc(C=C2SCN(CC#N)C2=O)cc(C(C)(C)C)c1O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 431f5f5bf6f9cf449d2e55b8c9492e72e15ac1fd928cbbb6a7e09ce10662fe6f | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1NCSC1=Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[C:7]-[#16:8]-[C:9]-1=[C:10]-[c:11]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:7]-[#16:8]-[C:9](=[C:10]-[c:11])-[C:5]-1=[O;D1;H0:4] | 40.7 | [{"value": 40.7, "product": "CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CC#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7.03 g of 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-thiazolidinone and 2.64 g of bromoacetonitrile were reacted in the presence of 0.97 g of 60% sodium hydride in mineral oil and 330 ml of tetrahydrofuran. Work-up of the reaction mixture provided 3.21 g of the desired title product, m.p. 186°-188° C.
... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | C1CSCN1 | C1CSC[NH]1 | c1ccccc1.C1CSC[NH]1 | HBr | O1CCCC1 | null | null | CC(C)(C)c1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O.N#CCBr>O1CCCC1>CC(C)(C)c1cc(C=C2SCN(CC#N)C2=O)cc(C(C)(C)C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95854aeecbe74885a11782806e4adc91 | CCN(C)N1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S>>CCN(C)N1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | C(CCC)[SnH](CCCC)CCCC.CC(C)(C#N)N=NC(C)(C)C#N.CC(C)(C#N)N=NC(C)(C)C#N.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)N(C)CC)=O.Cl>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)N(C)CC)=O | S=[C:6]1[N:5]([N:3]([CH2:2][CH3:1])[CH3:4])[C:25](=[O:26])[C:8](=[CH:9][c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([OH:18])[c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24]2)[S:7]1>>[CH3:1][CH2:2][N:3]([CH3:4])[N:5]1[CH2:6][S:7][C:8](=[CH:9][c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:1... | CCN(C)N1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S | CCN(C)N1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | null | null | C1(=CC=CC=C1)C.C(Cl)(Cl)Cl.CCCCCC.C(C)(=O)OCC | Reduction | OtherReaction | 3075aa4a480315be93c6069c30839bbd13f7a2020ecf519735ecee8afa07f2e9 | 0f72a6a79dcf7806020691b0c331ca1668d57eb95f4b08c405899f23029b31ef | O=C1NCSC1=Cc1ccccc1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3](=[C:4]-[c:5])-[C:6](=[O;D1;H0:7])-[#7:8]-1-[#7:9](-[C:10])-[C;D1;H3:11]>>[C:10]-[#7:9](-[C;D1;H3:11])-[#7:8]1-[CH2;D2;+0:1]-[#16:2]-[C:3](=[C:4]-[c:5])-[C:6]-1=[O;D1;H0:7] | 29.8 | [{"value": 29.8, "product": "CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)N(C)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 7.02 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-(ethylmethylamino)-2-thioxo-4-thiazolidinone (from Example 40D) and 86.3 ml of toluene were stirred and heated to 60° C. under a nitrogen atmosphere. To this was added 18.6 ml of tri-n-butyl tin hydride and 0.43 g of AIBN. The resultant mixture was h... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide | Monosulfide | C1CSC[NH]1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | Other | C1(=CC=CC=C1)C.C(Cl)(Cl)Cl.CCCCCC.C(C)(=O)OCC | 60 | null | CCN(C)N1C(=O)C(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S>C1(=CC=CC=C1)C.C(Cl)(Cl)Cl.CCCCCC.C(C)(=O)OCC>CCN(C)N1CSC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5ea8ac69bd1848ae813a64e74a7a7adf | CC(=O)Cl.CC(C)(C)c1cccc(C(C)(C)C)c1O>>CC(=O)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 | C(C)(=O)Cl.Cl.C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C(C)=O | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][c:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]([OH:12])[c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]([OH:12])[c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18]1 | CC(=O)Cl.CC(C)(C)c1cccc(C(C)(C)C)c1O | CC(=O)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | -4 | CELSIUS | null | null | Under a nitrogen atmosphere, 6.89 ml of acetylchloride and 14.75 ml of stannic chloride were dissolved in 200 ml of methylene chloride and chilled to -4° C. To this was added 20 g of 2,6-di-t-butylphenol (in 100 ml of methylene chloride) over 10 minutes. The resultant mixture was stirred for 30 minutes at 0° C., then p... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(Cl)Cl | -4 | null | CC(=O)Cl.CC(C)(C)c1cccc(C(C)(C)C)c1O>C(Cl)Cl>CC(=O)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c1a0b94f8eae41118a0fa90768e7a49a | CC(=O)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1.CN(C)N1C(=O)CSC1=S>>CN(C)N1C(=O)C(=CCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S | C1(=CC=CC=C1)C.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C(C)=O.CN(N1C(SCC1=O)=S)C.C(C)(=O)[O-].[NH4+]>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC=C1C(N(C(S1)=S)N(C)C)=O | O=[C:9]([CH3:8])[c:10]1[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([OH:18])[c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24]1.[CH3:1][N:2]([CH3:3])[N:4]1[C:5](=[O:6])[CH2:7][S:25][C:26]1=[S:27]>>[CH3:1][N:2]([CH3:3])[N:4]1[C:5](=[O:6])[C:7](=[CH:8][CH2:9][c:10]2[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:1... | CC(=O)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1.CN(C)N1C(=O)CSC1=S | CN(C)N1C(=O)C(=CCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | dfde106ced2a3f73217c11f5f6d51cc4a7248ee710aad45f60a2a92ceaf74e04 | 45dd82e4ad226b68ad41abe96a21c6b8401d4268cf20b034c57837b2fc1df3d6 | O=C1NC(=S)SC1=CCc1ccccc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[#7:7]1-[C:8](=[S;D1;H0:9])-[#16:10]-[CH2;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[#7:6]-[#7:7]1-[C:8](=[S;D1;H0:9])-[#16:10]-[C;H0;D3;+0:11](=[CH;D2;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5])-[C:12]-1=[O;D1;H0:13] | null | [] | null | null | null | null | To 675 ml of toluene were added 20.9 g of 1-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethanone, 13.3 g of N-dimethylaminorhodanine 6.5 g of ammonium acetate and about 20 ml of acetic acid. The mixture was heated at reflux temperature and any aqueous layer generated was collected in a Dean-Stark trap. Over the followi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Monosulfide | Monosulfide | C1CSC[NH]1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | HO- | C(C)(=O)O | null | null | CC(=O)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1.CN(C)N1C(=O)CSC1=S>C(C)(=O)O>CN(C)N1C(=O)C(=CCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)SC1=S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c27d491eec04e228dfd3d1e3bf80bcf | C=CCc1cc(C=O)cc(CC=C)c1O.O=C1CSC(=S)N1>>C=CCc1cc(C=C2SC(=S)NC2=O)cc(CC=C)c1O | C(C=C)C=1C=C(C=O)C=C(C1O)CC=C.S1C(=S)NC(=O)C1.C(C)(=O)[O-].[Na+]>>C(C=C)C=1C=C(C=C(C1O)CC=C)C=C1C(NC(S1)=S)=O | O=[CH:7][c:6]1[cH:5][c:4]([CH2:3][CH:2]=[CH2:1])[c:20]([OH:21])[c:16]([CH2:17][CH:18]=[CH2:19])[cH:15]1.[CH2:8]1[S:9][C:10](=[S:11])[NH:12][C:13]1=[O:14]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([CH:7]=[C:8]2[S:9][C:10](=[S:11])[NH:12][C:13]2=[O:14])[cH:15][c:16]([CH2:17][CH:18]=[CH2:19])[c:20]1[OH:21] | C=CCc1cc(C=O)cc(CC=C)c1O.O=C1CSC(=S)N1 | C=CCc1cc(C=C2SC(=S)NC2=O)cc(CC=C)c1O | null | null | C(C)(=O)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=S)SC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 94.6 | [{"value": 94.6, "product": "C(C=C)C=1C=C(C=C(C1O)CC=C)C=C1C(NC(S1)=S)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3,5-di-(2-propenyl)-4-hydroxybenzaldehyde (50.5 g), 36.6 g of rhodanine and 164 g of sodium acetate were heated together at reflux temperature in 1.25 liter of acetic acid for 14.5 hours. The resultant solution was cooled, poured into 2 liter of ice water to yield, upon separation, about 75 g of 5-[(3,5-di-2-propenyl-4... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1ccccc1.C1CSCN1 | HO- | C(C)(=O)O | null | null | C=CCc1cc(C=O)cc(CC=C)c1O.O=C1CSC(=S)N1>C(C)(=O)O>C=CCc1cc(C=C2SC(=S)NC2=O)cc(CC=C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e337e55a1fd94b369c26bae4adbf39ba | Cc1cccc(C(C)(C)C)c1O.O=C(O)C(F)(F)F>>Cc1cc(C=O)cc(C(C)(C)C)c1O | CC(C)(C)C1=C(C(=CC=C1)C)O.C1N2CN3CN1CN(C2)C3.FC(C(=O)O)(F)F>>CC(C)(C)C=1C=C(C=O)C=C(C1O)C | [CH3:1][c:2]1[cH:3][cH:4][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[c:13]1[OH:14].O[C:5](C(F)(F)F)=[O:6]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]=[O:6])[cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[c:13]1[OH:14] | Cc1cccc(C(C)(C)C)c1O.O=C(O)C(F)(F)F | Cc1cc(C=O)cc(C(C)(C)C)c1O | null | null | null | C-C Coupling | OtherReaction | 90f745ece0b80581a2adb80202cff13794970e7773efa9f99af5aee9558e7702 | 926b2e005c3200dff13912ddbfc878368a562a8e6eabbdd8fa25db32ad9e0671 | c1ccccc1 | F-C(-F)(-F)-[C;H0;D3;+0:1](-O)=[O;D1;H0:2].[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:5](:[c:4]:[c:3]):[c:6]:[c:7] | null | [] | null | null | null | null | Under a nitrogen atmosphere, 76.65 g of 2-(1,1-dimethylethyl)-6-methylphenol (Aldrich), 65.42 g of hexamethylenetetramine and 700 ml of trifluoroacetic acid were stirred at reflux temperature for about 24 hours, then allowed to cool and evaporated. The residue from the evaporation was taken up in 1500 ml of water and 1... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | null | null | null | Cc1cccc(C(C)(C)C)c1O.O=C(O)C(F)(F)F>>Cc1cc(C=O)cc(C(C)(C)C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b92740c81364c30af7dcfcac8c1abbd | CC(C)(C)c1ccccc1O.CN(C=O)c1ccccc1>>CC(C)(C)c1cc(C=O)ccc1O | CN(C1=CC=CC=C1)C=O.P(=O)(Cl)(Cl)Cl.C(C)(C)(C)C1=C(C=CC=C1)O>>CC(C)(C)C=1C=C(C=O)C=CC1O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:10][cH:11][c:12]1[OH:13].CN(c1ccccc1)[CH:8]=[O:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[O:9])[cH:10][cH:11][c:12]1[OH:13] | CC(C)(C)c1ccccc1O.CN(C=O)c1ccccc1 | CC(C)(C)c1cc(C=O)ccc1O | null | null | null | C-C Coupling | OtherReaction | 285803636db9e45ff0b980aa9c160ed6302cad8a21b5d872b908f4e4658d903e | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-[CH;D2;+0:1]=[O;D1;H0:2])-c1:c:c:c:c:c:1.[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:5](:[c:4]:[c:3]):[c:6]:[c:7] | 22.6 | [{"value": 22.6, "product": "CC(C)(C)C=1C=C(C=O)C=CC1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 70 | MINUTE | Into 101.5 g of N-methylformanilide was added dropwise with cooling 107 g of phosphoryl chloride over a period of 15 minutes. The mixture was allowed to warm to room temperature and stirred for 70 minutes. 67.5 g of ortho-t-butylphenol was added and stirred for about 45 minutes after which the mixture was heated to abo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | null | null | 1.166667 | CC(C)(C)c1ccccc1O.CN(C=O)c1ccccc1>>CC(C)(C)c1cc(C=O)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4349083726d1496ca8ab1e9e85158d89 | Cc1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O>>Cc1cc(CC2SCNC2=O)cc(C(C)(C)C)c1O | CC(C)(C)C=1C=C(C=C(C1O)C)C=C1C(NCS1)=O>>CC(C)(C)C=1C=C(C=C(C1O)C)CC1C(NCS1)=O | [CH3:1][c:2]1[cH:3][c:4]([CH:5]=[C:6]2[S:7][CH2:8][NH:9][C:10]2=[O:11])[cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]1[OH:19]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]2[S:7][CH2:8][NH:9][C:10]2=[O:11])[cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]1[OH:19] | Cc1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O | Cc1cc(CC2SCNC2=O)cc(C(C)(C)C)c1O | null | [Pd] | O1CCCC1 | Reduction | Hydrogenation (double to single) | 5287357a9ceae46aa07f85d3bac2070fe5bb40eaa8eb1baec18cbe42a25e8909 | 229264280d760663074461f898bce2a68d1dd7a993ad956085f2c6522e0edd11 | O=C1NCSC1Cc1ccccc1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4]-[#16:5]-[C;H0;D3;+0:6]-1=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4]-[#16:5]-[CH;D3;+0:6]-1-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10] | 17.7 | [{"value": 17.7, "product": "CC(C)(C)C=1C=C(C=C(C1O)C)CC1C(NCS1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.28 g of the compound of Example 61 in 30 ml of tetrahydrofuran was hydrogenated at 60 pounds per square inch in the presence of 1.12 g of 5% palladium on carbon overnight at 60° C. The reaction mixture was filtered and evaporated to dryness. The resulting residue was dissolved in 3.5 ml of a 1:1.5 ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1ccccc1.C1CSCN1 | null | [Pd].O1CCCC1 | null | null | Cc1cc(C=C2SCNC2=O)cc(C(C)(C)C)c1O>[Pd].O1CCCC1>Cc1cc(CC2SCNC2=O)cc(C(C)(C)C)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f43f465340624f4daaa306b11664c6ec | C=CCBr.CC(C)(C)c1ccccc1O>>CC=COc1ccccc1C(C)(C)C | O.C(C=C)Br.C(C)(C)(C)C1=C(C=CC=C1)O.C([O-])([O-])=O.[K+].[K+]>>CC(C)(C)C1=C(OC=CC)C=CC=C1 | Br[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([CH3:12])([CH3:13])[CH3:14]>>[CH3:1][CH:2]=[CH:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([CH3:12])([CH3:13])[CH3:14] | C=CCBr.CC(C)(C)c1ccccc1O | CC=COc1ccccc1C(C)(C)C | null | null | CC(=O)C | Acylation | OtherReaction | 6e103d63fa32b1f25589a1bb9fee272006c8c773242013ac4b5934f281886540 | 93ac263db2a078733b538b75f825301246e9bd073e80d72516f48f3892614147 | c1ccccc1 | Br-[CH2;D2;+0:1]-[CH;D2;+0:2]=[CH2;D1;+0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[CH3;D1;+0:3]-[CH;D2;+0:2]=[CH;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 35 | CELSIUS | null | null | Allyl bromide (69.2 ml), 2-t-butylphenol (122.9 ml) and potassium carbonate (121.6 g) were stirred in 265 ml of acetone at reflux temperature for 50 hours and then cooled to 35° C. Water (600 ml) was added and the resulting layers were separated. The aqueous layer was extracted with 600 ml of diethyl ether. The organic... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol.Allyl | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | 35 | null | C=CCBr.CC(C)(C)c1ccccc1O>CC(=O)C>CC=COc1ccccc1C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c7e1f9ffd3ca4282bfc5320d69389735 | CC(C)(C)c1ccccc1O.CN(C=O)c1ccccc1>>CC(C)(C)c1cc(C=O)ccc1O | C1(=CC=CC=C1)O.CN(C1=CC=CC=C1)C=O.P(=O)(Cl)(Cl)Cl.C(C)(C)(C)C1=C(C=CC=C1)O>>CC(C)(C)C=1C=C(C=O)C=CC1O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:10][cH:11][c:12]1[OH:13].CN(c1ccccc1)[CH:8]=[O:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[O:9])[cH:10][cH:11][c:12]1[OH:13] | CC(C)(C)c1ccccc1O.CN(C=O)c1ccccc1 | CC(C)(C)c1cc(C=O)ccc1O | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 285803636db9e45ff0b980aa9c160ed6302cad8a21b5d872b908f4e4658d903e | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-[CH;D2;+0:1]=[O;D1;H0:2])-c1:c:c:c:c:c:1.[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:5](:[c:4]:[c:3]):[c:6]:[c:7] | null | [] | null | null | 1 | HOUR | Into 184.4 ml (1,494 mol) of N-methylformanilide were added dropwise, with cooling, 130.9 ml (1,404 mol) of phosphoryl chloride over a period of 20 minutes. The mixture was allowed to warm to room temperature and stirred for one hour. Ortho-tertbutylphenol (138.2 ml; 0.9 mol) was then added dropwise to the reaction sol... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1(=CC=CC=C1)C | null | 1 | CC(C)(C)c1ccccc1O.CN(C=O)c1ccccc1>C1(=CC=CC=C1)C>CC(C)(C)c1cc(C=O)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-da305453c99c4c2c9addcfb5438c3fa0 | CC(C)(C)c1cc(C=C2SCNC2=O)ccc1O>>CC(C)(C)c1cc(CC2SCNC2=O)ccc1O | [Mg].CC(C)(C)C=1C=C(C=CC1O)C=C1C(NCS1)=O.[Mg].C(C)(=O)OCC.[Mg]>>CC(C)(C)C=1C=C(C=CC1O)CC1C(NCS1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH:8]=[C:9]2[S:10][CH2:11][NH:12][C:13]2=[O:14])[cH:15][cH:16][c:17]1[OH:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([CH2:8][CH:9]2[S:10][CH2:11][NH:12][C:13]2=[O:14])[cH:15][cH:16][c:17]1[OH:18] | CC(C)(C)c1cc(C=C2SCNC2=O)ccc1O | CC(C)(C)c1cc(CC2SCNC2=O)ccc1O | null | null | CO | Reduction | Hydrogenation (double to single) | 5287357a9ceae46aa07f85d3bac2070fe5bb40eaa8eb1baec18cbe42a25e8909 | 229264280d760663074461f898bce2a68d1dd7a993ad956085f2c6522e0edd11 | O=C1NCSC1Cc1ccccc1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4]-[#16:5]-[C;H0;D3;+0:6]-1=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4]-[#16:5]-[CH;D3;+0:6]-1-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10] | 72.9 | [{"value": 72.9, "product": "CC(C)(C)C=1C=C(C=CC1O)CC1C(NCS1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A portion of the title compound from Example 77 (395.1 mg; 1.5 mmol) was dissolved in 9 ml of methanol. Magnesium (72.9 mg; 3.0 mmol) was then added to the solution and the resulting reaction mixture was stirred at room temperature for 3 hours. After 3 hours, most of the magnesium which had been added originally appear... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1ccccc1.C1CSCN1 | null | CO | null | 3 | CC(C)(C)c1cc(C=C2SCNC2=O)ccc1O>CO>CC(C)(C)c1cc(CC2SCNC2=O)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bdf0ab77d0b64f258945b0b094a91458 | ClCCN1CCCCC1.N#CCc1ccccc1Cl>>N#CC(CCN1CCCCC1)c1ccccc1Cl | ClCCN1CCCCC1.ClC1=C(C=CC=C1)CC#N>>ClC1=C(C=CC=C1)C(C#N)CCN1CCCCC1 | Cl[CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1.[N:1]#[C:2][CH2:3][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[N:1]#[C:2][CH:3]([CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18] | ClCCN1CCCCC1.N#CCc1ccccc1Cl | N#CC(CCN1CCCCC1)c1ccccc1Cl | null | null | null | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(CCCN2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[N;D1;H0:4]#[C:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:6](-[C:5]#[N;D1;H0:4])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | The present invention relates to a novel process for the preparation of N-heterocyclealkanamide derivatives having the following formula: ##STR1## which comprises reacting 1-(2-chloroethyl)piperidine with 2-chlorobenzeneacetonitrile to give (±)-α-(2-chlorophenyl)-1-piperidinebutanenitrile; alkylating the piperidenebuta... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | C1CC[NH]CC1.c1ccccc1 | HCl | null | null | null | ClCCN1CCCCC1.N#CCc1ccccc1Cl>>N#CC(CCN1CCCCC1)c1ccccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d74b87b2489c48b89d16e8e1866c62a5 | COC(CBr)OC.N#CC(CCN1CCCCC1)c1ccccc1Cl>>COC(CC(C#N)(CCN1CCCCC1)c1ccccc1Cl)OC | [OH-].[K+].ClC1=C(C=CC=C1)C(C#N)CCN1CCCCC1.COC(CBr)OC>>ClC1=C(C=CC=C1)C(C#N)(CCN1CCCCC1)CC(OC)OC | Br[CH2:4][CH:3]([O:2][CH3:1])[O:23][CH3:24].[CH:5]([C:6]#[N:7])([CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[Cl:22]>>[CH3:1][O:2][CH:3]([CH2:4][C:5]([C:6]#[N:7])([CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20... | COC(CBr)OC.N#CC(CCN1CCCCC1)c1ccccc1Cl | COC(CC(C#N)(CCN1CCCCC1)c1ccccc1Cl)OC | null | null | CS(=O)C | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(CCCN2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[C:5]-[C:6]-[CH;D3;+0:7](-[C:8]#[N;D1;H0:9])-[c:10](:[c:11]):[c:12]>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[C;H0;D4;+0:7](-[C:8]#[N;D1;H0:9])(-[C:6]-[C:5])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | The synthesis outlined in Scheme II comprises (a) reacting commercially available 2-chlorobenzeneacetonitrile with 1-(2-chloroethyl)piperidine in the presence of a base, such as sodium hydroxide, and methyltributylammonium chloride to give (±)-α-(2-chlorophenyl)-1-piperidinebutanenitrile; (b) alkylating the resulting p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | C1CC[NH]CC1.c1ccccc1 | HBr | CS(=O)C | null | null | COC(CBr)OC.N#CC(CCN1CCCCC1)c1ccccc1Cl>CS(=O)C>COC(CC(C#N)(CCN1CCCCC1)c1ccccc1Cl)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a0d3c88ef6d4534849af2d89a1f5da0 | ClCCN1CCCCC1.N#CCc1ccccc1Cl>>N#CCCCN1CCCCC1 | ClCCN1CCCCC1.ClC1=C(C=CC=C1)CC#N>>N1(CCCCC1)CCCC#N | Cl[CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1.Clc1ccccc1[CH2:3][C:2]#[N:1]>>[N:1]#[C:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1 | ClCCN1CCCCC1.N#CCc1ccccc1Cl | N#CCCCN1CCCCC1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | d83e445d95973f2b4a9b1f4461f580f6f955409f7468ece658bb0d815a1ab0c7 | 84e12b0159f1d183204538a38a0b22f090552039c6c4b4ca4a95700e436c4e5e | C1CCNCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].Cl-c1:c:c:c:c:c:1-[CH2;D2;+0:4]-[C:5]#[N;D1;H0:6]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[CH2;D2;+0:4]-[C:5]#[N;D1;H0:6] | null | [] | null | null | null | null | A process for the preparation of a compound of the formula ##STR25## which comprises (a) reacting 2-chlorobenzeneacetonitrile with 1-(2-chloroethyl)piperidine in the presence of a base and DMSO to produce a piperidinebutanenitrile of the formula ##STR26## (b) alkylating the resulting piperidinebenzene-butanenitrile wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide | null | c1ccccc1 | null | C1CC[NH]CC1 | HCl | CS(=O)C | null | null | ClCCN1CCCCC1.N#CCc1ccccc1Cl>CS(=O)C>N#CCCCN1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b86839ffe9b04ba9843462354aa0bc38 | O=C(O)c1cc(F)c(F)c(F)c1F.O=S(Cl)Cl>>O=C(Cl)c1cc(F)c(F)c(F)c1F | FC1=C(C(=O)O)C=C(C(=C1F)F)F.S(=O)(Cl)Cl>>FC1=C(C(=O)Cl)C=C(C(=C1F)F)F | O[C:2](=[O:1])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]1[F:13].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]1[F:13] | O=C(O)c1cc(F)c(F)c(F)c1F.O=S(Cl)Cl | O=C(Cl)c1cc(F)c(F)c(F)c1F | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 40 | CELSIUS | null | null | A suspension of 200 g of 2,3,4,5-tetrafluorobenzoic acid, 225 ml of thionyl chloride and 5 ml of N,N-dimethylformamide, prepared at 20° C., is heated at reflux for 3 hours. After cooling at 40° C., the thionyl chloride in excess is evaporated off under vacuum. The residue is taken up with toluene and the solution is co... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | CN(C=O)C | 40 | null | O=C(O)c1cc(F)c(F)c(F)c1F.O=S(Cl)Cl>CN(C=O)C>O=C(Cl)c1cc(F)c(F)c(F)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ece997c552924fb094fb0d886a9ac725 | N#Cc1cnc2cc(Cl)cc(Cl)c2c1O.O=S(=O)(O)O>>N#Cc1cnc2cc(Cl)cc(Cl)c2c1O.Oc1ccnc2cc(Cl)cc(Cl)c12 | ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C#N)O.S(O)(O)(=O)=O>>ClC1=C2C(=CC=NC2=CC(=C1)Cl)O.ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C#N)O | [N:1]#[C:2][c:3]1[c:14]([OH:15])[c:13]2[c:11]([Cl:12])[cH:4][c:23]([Cl:9])[cH:22][c:21]2[n:20][cH:19]1.O=S(=O)(O)[OH:16]>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[cH:7][c:8]([Cl:9])[cH:10][c:11]([Cl:12])[c:13]2[c:14]1[OH:15].[OH:16][c:17]1[cH:18][cH:19][n:20][c:21]2[cH:22][c:23]([Cl:24])[cH:25][c:26]([Cl:27])[c:28]12 | N#Cc1cnc2cc(Cl)cc(Cl)c2c1O.O=S(=O)(O)O | N#Cc1cnc2cc(Cl)cc(Cl)c2c1O.Oc1ccnc2cc(Cl)cc(Cl)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c735019a98d27e585603a74348688f1df57ce11b57c2bf750cbf751ef9525142 | 149b464c7b918309a049375e0f39cf7e369f0f11c620da9fa357bce4f7119362 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | O-S(=O)(=O)-[OH;D1;+0:1].[Cl;D1;H0:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[Cl;H0;D1;+0:6]):[c:7]:[c;H0;D3;+0:8]2:[#7;a:9]:[cH;D2;+0:10]:[c;H0;D3;+0:11](-[C:12]#[N;D1;H0:13]):[c:14](-[O;D1;H1:15]):[c;H0;D3;+0:16]:1:2>>[Cl;D1;H0:17]-[c;H0;D3;+0:5]1:[c:7]:[c;H0;D3;+0:8]2:[#7;a:9]:[cH;D2;+0:10]:[c:18]:[c:19](-[OH;... | null | [] | null | null | null | null | 5,7-Dichloro-3-cyano-4-hydroxyquinoline (7.0 g; 0.0293 mole) and 104 g of 62.5% sulfuric acid were charged in a 300 ml four-necked flask equipped with stirrer, thermometer and reflux condenser, and the mixture was heated up to a boiling point (144°-146° C.) during one hour and subjected to a reaction at the same temper... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic alcohol | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | null | null | null | null | N#Cc1cnc2cc(Cl)cc(Cl)c2c1O.O=S(=O)(O)O>>N#Cc1cnc2cc(Cl)cc(Cl)c2c1O.Oc1ccnc2cc(Cl)cc(Cl)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-57265bf9bb574995a79f159928fe6a0d | CCOC(=O)c1cnc2cc(Cl)cc(Cl)c2c1O.CCOC(=O)c1cnc2cc(Cl)cc(Cl)c2c1O>>O=C(O)c1cnc2cc(Cl)cc(Cl)c2c1O.Oc1ccnc2cc(Cl)cc(Cl)c12 | ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C(=O)OCC)O.ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C(=O)OCC)O.S(O)(O)(=O)=O>>ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C(=O)O)O.ClC1=C2C(=CC=NC2=CC(=C1)Cl)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][c:12]([Cl:13])[c:14]2[c:15]1[OH:16].CCOC(=O)[c:19]1[c:18]([OH:17])[c:29]2[c:22]([n:21][cH:20]1)[cH:23][c:24]([Cl:25])[cH:26][c:27]2[Cl:28]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][c:12]([Cl:13])[c:14]2[c:15]1[OH:16].[OH... | CCOC(=O)c1cnc2cc(Cl)cc(Cl)c2c1O.CCOC(=O)c1cnc2cc(Cl)cc(Cl)c2c1O | O=C(O)c1cnc2cc(Cl)cc(Cl)c2c1O.Oc1ccnc2cc(Cl)cc(Cl)c12 | null | null | C(C)O | Miscellaneous | OtherReaction | 2b397880b8a0c05490437c415034b13cfb138fc45779200235e7a54b468fef7f | 98ceecc6efaef107d55b13485e60ddb1097cad209257014b37d5538dd4834ad5 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[O;D1;H1:7].C-C-[O;H0;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]:[#7;a:13]>>[#7;a:13]:[c:12]:[c:11]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:8].[O;D1;H1:7]-[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[cH;D2;+0:1]:1 | null | [] | 150 | CELSIUS | null | null | 5,7-Dichloro-3-ethoxycarbonyl-4-hydroxyquinoline (114.4 g; 0.4 mole) and 343.2 g of 70% sulfuric acid were charged in a 1,000 ml four-necked flask equipped with stirrer, thermometer and distilling tube and the mixture was heated at 150° C. with stirring. Reaction was continued by heating up to 165° C. during three hour... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | HO- | C(C)O | 150 | null | CCOC(=O)c1cnc2cc(Cl)cc(Cl)c2c1O.CCOC(=O)c1cnc2cc(Cl)cc(Cl)c2c1O>C(C)O>O=C(O)c1cnc2cc(Cl)cc(Cl)c2c1O.Oc1ccnc2cc(Cl)cc(Cl)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-428799f362c448f9a4b5974ac3fa405b | NC1CCCCCC1.O=C(Br)CBr>>O=C(CBr)NC1CCCCCC1 | C1(CCCCCC1)N.C(C)(C)N(CC)C(C)C.BrCC(=O)Br>>BrCC(=O)NC1CCCCCC1 | [NH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.Br[C:2](=[O:1])[CH2:3][Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[NH:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1 | NC1CCCCCC1.O=C(Br)CBr | O=C(CBr)NC1CCCCCC1 | null | null | C(Cl)Cl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1CCCCCC1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8] | 89.7 | [{"value": 89.7, "product": "BrCC(=O)NC1CCCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a -20° C. solution of cycloheptylamine (6.37 mL, 50.0 mmol) and diisopropylethylamine (9.58 mL, 55.0 mmol) in methylene chloride (250 mL) was slowly added bromoacetyl bromide (4.78 mL, 55.0 mmol). The reaction mixture was warmed to room temperature over 20 minutes and stirred for an addition 30 minutes. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCCCC1 | HBr | C(Cl)Cl.O | null | 0.5 | NC1CCCCCC1.O=C(Br)CBr>C(Cl)Cl.O>O=C(CBr)NC1CCCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-31db870c320a495ea81c261721daf508 | NOCc1ccccc1.O=C(Br)CBr>>O=C(CBr)NOCc1ccccc1 | Cl.C(C1=CC=CC=C1)ON.BrCC(=O)Br.C(C)(C)N(CC)C(C)C>>BrCC(=O)NOCC1=CC=CC=C1 | [NH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.Br[C:2](=[O:1])[CH2:3][Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[NH:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | NOCc1ccccc1.O=C(Br)CBr | O=C(CBr)NOCc1ccccc1 | null | null | C1CCOC1.O.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[#8:6]-[C:5] | 52 | [{"value": 52.0, "product": "BrCC(=O)NOCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.0, "product": "BrCC(=O)NOCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 0° C. solution of O-benzylhydroxylamine hydrochloride (1.6 g, 10 mmol) in THF (40 mL) was added bromoacetyl bromide (871 μL, 10 mmol) and diisopropylethylamine (3.5 mL, 20 mmol). The reaction mixture was warmed to room temperature overnight and diluted with ethyl acetate and water. The aqueous layer was separated ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HBr | C1CCOC1.O.C(C)(=O)OCC | null | null | NOCc1ccccc1.O=C(Br)CBr>C1CCOC1.O.C(C)(=O)OCC>O=C(CBr)NOCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a73c3e09e44447508491ea934b7c975c | COc1ccc(N)cc1.O=C(Br)CBr>>COc1ccc(NC(=O)CBr)cc1 | BrCC(=O)Br.COC1=CC=C(N)C=C1.C(C)(C)N(CC)C(C)C>>BrCC(=O)NC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:12][cH:13]1.Br[C:8](=[O:9])[CH2:10][Br:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH2:10][Br:11])[cH:12][cH:13]1 | COc1ccc(N)cc1.O=C(Br)CBr | COc1ccc(NC(=O)CBr)cc1 | null | null | C(Cl)Cl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | -20 | CELSIUS | 30 | MINUTE | The title compound was prepared via a modification of the literature procedure (Vloon, W. J.; Kruk, C.; Pandit, U. K.; Hofs, H. P.; McVie, J. G. J. Med Chem. 1987, 30, 20-4.). To a solution of 4-methoxyaniline (4.93 g, 40.0 mmol) in methylene chloride (200 mL) was added diisopropylethylamine (7.66 mL, 44.0 mmol). The r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HBr | C(Cl)Cl.O | -20 | 0.5 | COc1ccc(N)cc1.O=C(Br)CBr>C(Cl)Cl.O>COc1ccc(NC(=O)CBr)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8bfebd9748154a9780039335f8d6e481 | CC(C)c1ccccc1S.O=C=O>>CC(C)c1cccc(C(=O)O)c1S | C(=O)=O.C(C)(C)C1=C(C=CC=C1)S.CN(C)CCN(C)C.[Li]CCCC>>SC1=C(C(=O)O)C=CC=C1C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:12]1[SH:13].[C:9](=[O:10])=[O:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[SH:13] | CC(C)c1ccccc1S.O=C=O | CC(C)c1cccc(C(=O)O)c1S | null | null | C1CCCCC1 | Acylation | OtherReaction | d512242205ca0afb7920772ddd09825654068f093b5b2190929ae26db328221a | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccccc1 | [O;D1;H0:1]=[C;H0;D2;+0:2]=[O;H0;D1;+0:3].[S;D1;H1:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:3])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[S;D1;H1:4]):[c:6] | null | [] | null | null | 24 | HOUR | To a solution of 1.0 mmol 2-isopropylthiophenol and 2.2 mmol TMEDA in 2 mL cyclohexane was added 2.2 mmol n-BuLi. Then after stirring 24 h it was added to solid CO2 and stirred for 16 h when extraction and chromatography provided 2-mercapto-3-isopropylbenzoic acid. The methyl ester of this was treated as in example 3 t... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C1CCCCC1 | null | 24 | CC(C)c1ccccc1S.O=C=O>C1CCCCC1>CC(C)c1cccc(C(=O)O)c1S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-53859d19f5084c73a9229630dac0c84d | BrCCCBr.COC(=O)CNCC(=O)OC>>COC(=O)CN(CCCBr)CC(=O)OC | Cl.COC(CNCC(=O)OC)=O.C(C)(C)N(C(C)C)CC.BrCCCBr>>BrCCCN(CC(=O)OC)CC(=O)OC | Br[CH2:7][CH2:8][CH2:9][Br:10].[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH2:11][C:12](=[O:13])[O:14][CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]([CH2:7][CH2:8][CH2:9][Br:10])[CH2:11][C:12](=[O:13])[O:14][CH3:15] | BrCCCBr.COC(=O)CNCC(=O)OC | COC(=O)CN(CCCBr)CC(=O)OC | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:6](=[O;D1;H0:7])-[#8:5]-[C;D1;H3:4])-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14] | null | [] | 90 | CELSIUS | 16 | HOUR | A mixture of 1 mmol iminodiacetic acid dimethylester hydrochloride salt, 5 mmol N,N-diisopropyl-ethylamine and 3 mmol 1,3-dibromopropane in 2 mL toluene was stirred at 90° C. for 16 h and then chromatographed to provide the title compound as an oil.
Conditions: See reaction.notes.procedure_details.
Workup: chromatograp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | null | HBr | C1(=CC=CC=C1)C | 90 | 16 | BrCCCBr.COC(=O)CNCC(=O)OC>C1(=CC=CC=C1)C>COC(=O)CN(CCCBr)CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5a686fbf7b9481c9a917b96b78bc8ab | CN.Cc1ccc(C(=O)O)cc1I>>CNC(=O)c1ccc(C)c(I)c1 | IC=1C=C(C(=O)O)C=CC1C.S(=O)(=O)(C1=CC=C(C)C=C1)Cl.Cl.CN>>CNC(=O)C1=CC(=C(C=C1)C)I | [CH3:1][NH2:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([I:11])[cH:12]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([I:11])[cH:12]1 | CN.Cc1ccc(C(=O)O)cc1I | CNC(=O)c1ccc(C)c(I)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | HOUR | A solution of 1.0 mmol of 3-iodo-4-methylbenzoic acid, 1.2 mmol of TsCl, and 25 mmol of Py was stirred for 3 h and then 5 mmol of methylamine hydrochloride was added and stirring continued for 5 h. Chromatography provided N-methyl-(3-iodo-4-methylphenyl)carboxamide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | null | null | 5 | CN.Cc1ccc(C(=O)O)cc1I>>CNC(=O)c1ccc(C)c(I)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f2ad81b1f6b433ea7c984999ad32978 | COC(=O)[C@@H](N)Cc1ccccc1.O=CO>>COC(=O)[C@H](Cc1ccccc1)NC=O | Cl.COC([C@@H](N)CC1=CC=CC=C1)=O.C(C)N(CC)CC.C(=O)O.C(C)(=O)OC(C)=O>>COC([C@@H](NC=O)CC1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[NH2:13].O[CH:14]=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[NH:13][CH:14]=[O:15] | COC(=O)[C@@H](N)Cc1ccccc1.O=CO | COC(=O)[C@H](Cc1ccccc1)NC=O | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4](-[NH2;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9]>>[C:3]-[C:4](-[NH;D2;+0:5]-[CH;D2;+0:1]=[O;D1;H0:2])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9] | null | [] | null | null | 16 | HOUR | To a mixture of 1 mmol of phenylalanine methyl ester hydrochloride and 2 mmol of triethylamine in 1 mL of DMF at 0 ° C. was added 2 mL of formic acid and 0.7 mL of acetic anhydride. After stirring for 16 h at rt, extractive isolation provided N-formylphenylalanine methyl ester.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C)C=O | null | 16 | COC(=O)[C@@H](N)Cc1ccccc1.O=CO>CN(C)C=O>COC(=O)[C@H](Cc1ccccc1)NC=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c2ee4b9716b4027b28c9669b15472c1 | BrCc1ccccc1.O=C1CCCCCO1>>O=C1OCCCCC1Cc1ccccc1 | C1(CCCCCO1)=O.[Li+].CC(C)[N-]C(C)C.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)C1C(=O)OCCCC1 | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[O:1]=[C:2]1[O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1>>[O:1]=[C:2]1[O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | BrCc1ccccc1.O=C1CCCCCO1 | O=C1OCCCCC1Cc1ccccc1 | null | null | CN1CCCN(C1=O)C.C1CCOC1 | C-C Coupling | OtherReaction | 25c036e5de60d2288e3219b581ab60fd04dc861e67c8f6fab6b2a429046f7fbb | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C1OCCCCC1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10]-[C:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10]-[C:11] | null | [] | null | null | 2 | HOUR | A solution of 1 mmol of caprolactone in 0.5 mL THF was added to a solution of LDA in 0.5 mL THF at -78° C. and this stirred for 2 h. Then a solution of 1.1 mmol of a benzylbromide in 0.14 mL DMPU was added to the above mixture and after stirring for 1 h at -15° C., the 2-benzylcaprolactone was isolated by extraction an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | C1CCCOCC1 | C1CCCOCC1 | C1CCCOCC1.c1ccccc1 | HBr | CN1CCCN(C1=O)C.C1CCOC1 | null | 2 | BrCc1ccccc1.O=C1CCCCCO1>CN1CCCN(C1=O)C.C1CCOC1>O=C1OCCCCC1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-43fc139c41d84237a967f7fa62214d1c | CCOC(=O)c1ccc(C)c(Br)c1.O=C1CCC(=O)N1Br>>CCOC(=O)c1ccc(CBr)c(Br)c1 | BrC=1C=C(C(=O)OCC)C=CC1C.C1CC(=O)N(C1=O)Br.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrC=1C=C(C(=O)OCC)C=CC1CBr | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH3:10])[c:12]([Br:13])[cH:14]1.O=C1CCC(=O)N1[Br:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][Br:11])[c:12]([Br:13])[cH:14]1 | CCOC(=O)c1ccc(C)c(Br)c1.O=C1CCC(=O)N1Br | CCOC(=O)c1ccc(CBr)c(Br)c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture of 1.0 mmol of ethyl 3-bromo-4-methylbenzoate, 1.0 mmol NBS, and 0.02 mmol benzoyl peroxide in 5 mL CCl4 was refluxed for 4 h and then processed by filtration and chromatography to provide ethyl 3-bromo-4-bromomethylbenzoate as an oil.
Conditions: See reaction.notes.procedure_details.
Workup: was refluxed for... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | CCOC(=O)c1ccc(C)c(Br)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CCOC(=O)c1ccc(CBr)c(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-22f4a8336221412198601584d84cd4b1 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CCOC(=O)Cc1cccc(Br)c1>>C=Cc1cccc(CC(=O)OCC)c1 | BrC=1C=C(C=CC1)CC(=O)OCC.C(=C)[Sn](CCCC)(CCCC)CCCC>>C(=C)C=1C=C(C=CC1)CC(=O)OCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[O:11][CH2:12][CH3:13])[cH:14]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[O:11][CH2:12][CH3:13])[cH:14]1 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CCOC(=O)Cc1cccc(Br)c1 | C=Cc1cccc(CC(=O)OCC)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C)C=O | C-C Coupling | Stille reaction_vinyl | 70c70ea31829ab76af60acb09a55c00bc191f62cf69589ba5bf99dde81769bb5 | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:6]=[C;D1;H2:7]>>[C;D1;H2:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 90 | CELSIUS | null | null | A mixture of 1.0 mmol of ethyl 3-bromophenylacetate, 1.5 mmol of vinyltributyltin, and 0.1 mmol of Pd(PPh3)4 in 4 mL DMF was stirred and heated at 90° C. for 1-16 h. Chromatography provided ethyl 3-vinylphenylacetate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O | 90 | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CCOC(=O)Cc1cccc(Br)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O>C=Cc1cccc(CC(=O)OCC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2717ca80753c46a39e12e91d075435b5 | Cc1ccc(C(=O)O)cc1I>>Cc1ccc(CO)cc1I | II.IC=1C=C(C(=O)O)C=CC1C.[BH4-].[Na+]>>IC=1C=C(CO)C=CC1C | O=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:9]([I:10])[cH:8]1)[OH:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][OH:7])[cH:8][c:9]1[I:10] | Cc1ccc(C(=O)O)cc1I | Cc1ccc(CO)cc1I | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | A mixture of 1.0 mmol of 3-iodo-4-methylbenzoic acid and 1.2 mmol of NaBH4 in 4 mL of anhydrous THF was stirred for 30 min and then 0.5 mmol of iodine in 2.0 mL of THF at 5° C. was added. After stirring for 2 h the mixture was processed by extraction to provide 3-iodo-4-methylbenzyl alcohol.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | null | 0.5 | Cc1ccc(C(=O)O)cc1I>C1CCOC1>Cc1ccc(CO)cc1I |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bd82a5043a4441d6bb653b1731c79827 | Cc1ccc(CO)cc1I>>Cc1ccc(C=O)cc1I | IC=1C=C(CO)C=CC1C>>IC=1C=C(C=O)C=CC1C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][OH:7])[cH:8][c:9]1[I:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]1[I:10] | Cc1ccc(CO)cc1I | Cc1ccc(C=O)cc1I | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 16 | HOUR | A mixture of 1.0 mmol of this alcohol and 5.0 mmol of MnO2 in 5 mL of CH2Cl2 was stirred for 16 h at rt. Chromatography provided 3-iodo-4-methylbenzaldehyde.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | O=[Mn]=O.C(Cl)Cl | null | 16 | Cc1ccc(CO)cc1I>O=[Mn]=O.C(Cl)Cl>Cc1ccc(C=O)cc1I |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e65eb05600a341c1a97cfb8e1984da81 | Cc1ccc(C=O)cc1I>>C=Cc1ccc(C)c(I)c1 | IC=1C=C(C=O)C=CC1C.[Li]CCCC>>IC=1C=C(C=C)C=CC1C | O=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[c:8]([I:9])[cH:10]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[c:8]([I:9])[cH:10]1 | Cc1ccc(C=O)cc1I | C=Cc1ccc(C)c(I)c1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1 | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4.5 | HOUR | This aldehyde (1 mmol)was added to a premixed solution of 1.5 mmol of methyl triphenylphosphonium bromide and 1.2 mmol of n-BuLi in 5 mL of THF at 0° C. and this mixture was stirred for 3-6 h at rt and then processed by extraction and chromatography to give 3-iodo-4-methylstyrene.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | c1ccccc1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1 | null | 4.5 | Cc1ccc(C=O)cc1I>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>C=Cc1ccc(C)c(I)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d9642a5bf49d4ae5ab36a31093ec85a4 | CN(C)C=O.CO.O=Cc1ccc(F)c(Br)c1>>COC(=O)c1c(F)ccc(C=O)c1C | BrC=1C=C(C=O)C=CC1F.CN(C)C=O.C(C)N(CC)CC.CO>>CC1=C(C=O)C=CC(=C1C(=O)OC)F | CN([CH:3]=[O:4])[CH3:14].[CH3:1][OH:2].Br[c:5]1[c:6]([F:7])[cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][cH:9][c:10]([CH:11]=[O:12])[c:13]1[CH3:14] | CN(C)C=O.CO.O=Cc1ccc(F)c(Br)c1 | COC(=O)c1c(F)ccc(C=O)c1C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | Acylation | OtherReaction | ba60403ad7d45c466fc5a7cbbd7ecd8e4611ae8790a58d10f5ebcfca5f732591 | 3e4a6d9d1b66fe5eba87f87fea1406f49c9bbd0c9181018bc2624480752f7ca5 | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6]:[c:7]:[c:8]:1-[F;D1;H0:9].C-N(-[CH3;D1;+0:10])-[CH;D2;+0:11]=[O;D1;H0:12].[C;D1;H3:13]-[OH;D1;+0:14]>>[C;D1;H3:13]-[O;H0;D2;+0:14]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c;H0;D3;+0:1]1:[c:8](-[F;D1;H0:9]):[c:7]:[c:6]:[c:3](-[C:4]=[O;D1;H0:5]):[c;H0;D3;+0:2]:1-[CH... | null | [] | 90 | CELSIUS | null | null | A mixture of 1.0 mmol of 3-bromo-4-fluorobenzaldehyde, 4 mL of DMF, 0.2 mL of triethylamine, 0.4 mL of MeOH and 0.05 mmol of Pd(PPh3)4 was heated at 90° C. at 40 psi under CO atmosphere for 16 h. Extraction and chromatography provided methyl 3-carbomethoxy-4-fluorobenzaldehyde.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide.Methanol | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | 90 | null | CN(C)C=O.CO.O=Cc1ccc(F)c(Br)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>COC(=O)c1c(F)ccc(C=O)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-136efa4c469642d7aa6076afa6f445aa | C=CCBr.COC(=O)c1ccc(O)cc1>>C=CCOc1ccc(C(=O)OC)cc1 | OC1=CC=C(C(=O)OC)C=C1.C(C=C)Br.C(=O)([O-])[O-].[K+].[K+]>>C(C=C)OC1=CC=C(C(=O)OC)C=C1 | Br[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][cH:14]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][cH:14]1 | C=CCBr.COC(=O)c1ccc(O)cc1 | C=CCOc1ccc(C(=O)OC)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 16 | HOUR | A mixture of 1.0 mmol of methyl 4-hydroxybenzoate, 2.0 mmol of allyl bromide, 5.0 mmol of K2CO3 in 2 mL of acetone was stirred for 16 h. Extraction provided methyl 4-allyloxybenzoate.
Conditions: See reaction.notes.procedure_details.
Workup: Extraction | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | 16 | C=CCBr.COC(=O)c1ccc(O)cc1>CC(=O)C>C=CCOc1ccc(C(=O)OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dfbffeb92a874b419566deb178159f88 | C[Si](C)(C)CCOCCl.c1nnn[nH]1>>C[Si](C)(C)CCOCc1nnn[nH]1 | [H-].[Na+].N1N=NN=C1.C[Si](C)(C)CCOCCl>>C[Si](C)(C)CCOCC1=NN=NN1 | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[cH:9]1[n:10][n:11][n:12][nH:13]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][c:9]1[n:10][n:11][n:12][nH:13]1 | C[Si](C)(C)CCOCCl.c1nnn[nH]1 | C[Si](C)(C)CCOCc1nnn[nH]1 | null | null | CN(C)C=O | C-C Coupling | Friedel-Crafts alkylation with halide | fb624e15b1c94610b78ecee997322e12ee4707e936679f3788c5e4286a6590ad | 2c1c1647472d7e3cff37f0f3aad955b760f0ad2f8b7aa7e7825b1c0344bab3bb | c1nnn[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[#7;a:4]1:[#7;a:5]:[#7;a:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:8]1:[#7;a:4]:[#7;a:5]:[#7;a:6]:[#7;a:7]:1 | null | [] | null | null | 30 | MINUTE | To a Suspension of 1.1 mmol NaH in 5 mL DMF at 0° C. was added a solution of 1.0 mmol tetrazole in 2 mL DMF. After 30 min, trimethylsilylethoxymethylchloride was added and the mixture stirred for 16 h. Extraction and chromatography provided trimethylsilylethoxymethyltetrazole as an oil.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1nnn[nH]1 | c1nnn[nH]1 | c1nnn[nH]1 | HCl | CN(C)C=O | null | 0.5 | C[Si](C)(C)CCOCCl.c1nnn[nH]1>CN(C)C=O>C[Si](C)(C)CCOCc1nnn[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eddefb32d5b447c197ab4f1fb15647c7 | CCOC(=O)/N=N/C(=O)OCC.C[Si](C)(C)N=[N+]=[N-].Cc1ccc(C(=O)NCCCC#N)cc1Br>>Cc1ccc(-c2nnn[nH]2)cc1Br | C(#N)CCCNC(=O)C1=CC(=C(C=C1)C)Br.[Si](C)(C)(C)N=[N+]=[N-].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.CCOC(=O)/N=N/C(=O)OCC.[OH-].[Na+]>>BrC=1C=C(C=CC1C)C1=NN=NN1 | CCOC(=O)/N=[N:10]/C(=O)OCC.C[Si](C)(C)[N:9]=[N+:8]=[N-].N#CCCC[NH:7][C:6](=O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:12]([Br:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8][n:9][nH:10]2)[cH:11][c:12]1[Br:13] | CCOC(=O)/N=N/C(=O)OCC.C[Si](C)(C)N=[N+]=[N-].Cc1ccc(C(=O)NCCCC#N)cc1Br | Cc1ccc(-c2nnn[nH]2)cc1Br | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 1e21f3339edb565a87527ed8b41757afdd8ecc03dd2de2fc093175815bb9944d | c439d693e9db7d84799a5ea85d9916e0b6f8dc5cf4b645e682ed127f0e19a112 | c1ccc(-c2nnn[nH]2)cc1 | C-C-O-C(=O)/N=[N;H0;D2;+0:1]/C(=O)-O-C-C.C-[Si](-C)(-C)-[N;H0;D2;+0:2]=[N+;H0;D2:3]=[N-].N#C-C-C-C-[NH;D2;+0:4]-[C;H0;D3;+0:5](=O)-[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;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[nH;D2;+0:1]:1):[c:9]:[c:10] | null | [] | null | null | 24 | HOUR | A solution of 1.0 mmol of this amide, 4.0 mmol of TMSN3, 4.0 mmol of PPh3, and 4.0 mmol of DEAD in 4 mL of THF at 0° C. was stirred 24 h and then concentrated. The residue was mixed with 5 mL of THF and 12.0 mmol of 1N NaOH. After stirring for 24 h and processing by extraction, 5-(3'-bromo-4'-methylphenyl)tetrazole was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Azide.Diazene.Nitrile.Secondary amide.Silyl protective group | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | HO- | C1CCOC1 | null | 24 | CCOC(=O)/N=N/C(=O)OCC.C[Si](C)(C)N=[N+]=[N-].Cc1ccc(C(=O)NCCCC#N)cc1Br>C1CCOC1>Cc1ccc(-c2nnn[nH]2)cc1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23c1255e56f24480bb48d53be97ec0f6 | C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.C[Si](C)(C)CCOCCl.Cc1ccc(-c2nnn[nH]2)cc1Br>>C=CCc1cc(-c2nnnn2COCC[Si](C)(C)C)ccc1C | BrC=1C=C(C=CC1C)C1=NN=NN1.C[Si](C)(C)CCOCCl.C(C=C)[Sn](CCCC)(CCCC)CCCC>>C[Si](C)(C)CCOCN1N=NN=C1C1=CC(=C(C=C1)C)CC=C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2:3][CH:2]=[CH2:1].Cl[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19].Br[c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9][n:10][nH:11]2)[cH:20][cH:21][c:22]1[CH3:23]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9][n:10][n:11]2[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17]... | C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.C[Si](C)(C)CCOCCl.Cc1ccc(-c2nnn[nH]2)cc1Br | C=CCc1cc(-c2nnnn2COCC[Si](C)(C)C)ccc1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a005e3878e30a43bf567259f70b7f4ba1d07ab5f5c0f00f14c0c90d125f4a848 | f7295bf3a083b1df3497aac2272bb2d18238061c7b432d6c594e7b471a2845a5 | c1ccc(-c2nnn[nH]2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[c:4]1:[#7;a:5]:[#7;a:6]:[#7;a:7]:[nH;D2;+0:8]:1):[c:9](-[C;D1;H3:10]):[c:11].C-C-C-[CH2]-[Sn](-[CH2;D2;+0:12]-[C:13]=[C;D1;H2:14])(-[CH2]-C-C-C)-[CH2]-C-C-C.Cl-[CH2;D2;+0:15]-[#8:16]-[C:17]>>[C:17]-[#8:16]-[CH2;D2;+0:15]-[n;H0;D3;+0:8]1:[#7;a:7]:[#7;a:6]:[#7;a:5]:[c:4]:1-[c:3]:[c:2]:[c;H... | null | [] | 70 | CELSIUS | null | null | A solution of 1.0 mmol of this tetrazole, 2.0 mmol of SEMCl in 10 mL DMF was stirred for 1 h. 2.0 mmol of allyltributyltin and 0.1 mmol of Pd(Ph3)4 was added and heated at 70° C. for 14 h. Chromatography provided N-trimethylsilylethoxymethyl-5-(3'-allyl-4'-methylphenyl)tetrazole.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Ether.Allyl.Tin | Ether.Allyl | c1ccccc1.c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | HCl.Br-.Sn | CN(C)C=O | 70 | null | C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.C[Si](C)(C)CCOCCl.Cc1ccc(-c2nnn[nH]2)cc1Br>CN(C)C=O>C=CCc1cc(-c2nnnn2COCC[Si](C)(C)C)ccc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5c175917ded84c229e4c8ca00b6486e9 | C(=NC1CCCCC1)=NC1CCCCC1.CCN(CC)CC.CCOC(=O)CN.CN(C)C=O.O=C1CCC(=O)N1O>>CCOC(=O)CNC(=O)CCCn1cnc2c1N=CNCC2O | Cl.C(C)OC(CN)=O.C(C)N(CC)CC.C1(CCCCC1)N=C=NC1CCCCC1.ON1C(CCC1=O)=O.CN(C)C=O>>C(C)OC(CNC(CCCN1C=NC2=C1N=CNCC2O)=O)=O | C1CCC([N:18]=[C:17]=[N:13][CH:12]2CCCCC2)CC1.CCN(CC)[CH2:21][CH3:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH2:7].C[N:15]([CH:14]=O)[CH3:16].O=[C:19]1[CH2:11][CH2:10][C:8](=[O:9])[N:20]1[OH:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[CH2:10][CH2:11][CH2:12][n:13]1[cH:14][n:15][c:16]2[c:17]1[N:18]=... | C(=NC1CCCCC1)=NC1CCCCC1.CCN(CC)CC.CCOC(=O)CN.CN(C)C=O.O=C1CCC(=O)N1O | CCOC(=O)CNC(=O)CCCn1cnc2c1N=CNCC2O | null | null | null | Acylation | OtherReaction | b1abdcadc3c4683d16c91172c8d64f5ab275ec50a8adae785fdeb2779ee36e25 | 195215e4a044c563979e91a1ee35b31da4f8d65b9f4a25f3bf6c083ce76b08e2 | C1=Nc2[nH]cnc2CCN1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-[N;H0;D3;+0:3](-[CH3;D1;+0:4])-[CH;D2;+0:5]=O.C1-C-C-C(-[N;H0;D2;+0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[CH;D3;+0:9]2-C-C-C-C-C-2)-C-C-1.O=[C;H0;D3;+0:10]1-[CH2;D2;+0:11]-[C:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[N;H0;D3;+0:15]-1-[OH;D1;+0:16].[C:17]-[#8:18]-[C:19](=[O;D1;H0:20])-[C:... | null | [] | null | null | null | null | A mixture of 1 mmol of 3-(3'-carbobenzyloxypropyl)coformycin aglycone and10 mg of 10% Pd/C in 4 mL of methanol was subjected to hydrogenation. After filtration and removal of the solvent, 3-(3'-carboxypropyl)coformycin aglycone was obtained. This product, 2 mmol glycine ethyl ester hydrochloride, 2 mmol triethylamine, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Tertiary amide.Primary amine.Tertiary amine | Secondary amide.Secondary alcohol.Secondary amine | C1CCCCC1.C1CCCCC1.C1CC[NH]C1 | [CH]1CNC=Nc2[nH]cnc21 | [CH]1CNC=Nc2[nH]cnc21 | HO- | null | null | null | C(=NC1CCCCC1)=NC1CCCCC1.CCN(CC)CC.CCOC(=O)CN.CN(C)C=O.O=C1CCC(=O)N1O>>CCOC(=O)CNC(=O)CCCn1cnc2c1N=CNCC2O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c03739439424e59810e1f608eed556f | CS(=O)(=O)Cl.O=C(O)CCCCC(O)CCCl>>CS(=O)(=O)OC(CCCl)CCCCC(=O)O | ClCCC(CCCCC(=O)O)O.C(C)N(CC)CC.O.CS(=O)(=O)Cl>>ClCCC(CCCCC(=O)O)OS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH:6]([CH2:7][CH2:8][Cl:9])[CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[OH:16]>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH:6]([CH2:7][CH2:8][Cl:9])[CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[OH:16] | CS(=O)(=O)Cl.O=C(O)CCCCC(O)CCCl | CS(=O)(=O)OC(CCCl)CCCCC(=O)O | null | null | C1(=CC=CC=C1)C | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 30 | MINUTE | The methyl ester of (+)-8-chloro-6-hydroxy-octanoic acid (+)-(VIII) (R=Me) (4.0 g, 19.2 mmoles) and 1.97 g (19.2 mmoles) of triethylamine were mixed in 90 ml toluene. While cooling to an internal temperature of 10° to 15° C., 2.63 g (23.0 mmoles) of methanesulfonyl chloride were added slowly. Stirring was continued for... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C1(=CC=CC=C1)C | null | 0.5 | CS(=O)(=O)Cl.O=C(O)CCCCC(O)CCCl>C1(=CC=CC=C1)C>CS(=O)(=O)OC(CCCl)CCCCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b0a7372fca44f93a027eca27e6da381 | CS(=O)(=O)Cl.O=C(O)CCCCC(O)CCCl>>CS(=O)(=O)OC(CCCl)CCCCC(=O)O | ClCCC(CCCCC(=O)O)O.C(C)N(CC)CC.O.CS(=O)(=O)Cl>>ClCCC(CCCCC(=O)O)OS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH:6]([CH2:7][CH2:8][Cl:9])[CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[OH:16]>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH:6]([CH2:7][CH2:8][Cl:9])[CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[OH:16] | CS(=O)(=O)Cl.O=C(O)CCCCC(O)CCCl | CS(=O)(=O)OC(CCCl)CCCCC(=O)O | null | null | C1(=CC=CC=C1)C | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 30 | MINUTE | The methyl ester of (-)-8-chloro-6-hydroxy-octanoic acid (-)-(VIII), (R=Me) (2.1 g, 10 mmoles) and 1.0 g (10 mmoles) of triethylamine were mixed in 40 ml of toluene. While cooling to an internal temperature of 10° to 15° C., 1.4 g (12 mmoles) of methanesulfonyl chloride were added slowly. Stirring was continued for 30 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C1(=CC=CC=C1)C | null | 0.5 | CS(=O)(=O)Cl.O=C(O)CCCCC(O)CCCl>C1(=CC=CC=C1)C>CS(=O)(=O)OC(CCCl)CCCCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad0e6003b3be4ab6ac0a6c1f57d6ff26 | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>>O=C(O)CCCCC(Cl)CCCl | ClCCC(CCCCC(=O)O)O.N1=CC=CC=C1.S(=O)(Cl)Cl>>ClC(CCCCC(=O)O)CCCl | O[CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])[CH2:10][CH2:11][Cl:12].O=S(Cl)[Cl:9]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([Cl:9])[CH2:10][CH2:11][Cl:12] | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl | O=C(O)CCCCC(Cl)CCCl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6]>>[C:4]-[C:3]-[CH;D3;+0:2](-[Cl;H0;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | null | null | To a solution of 2.4 g (11.0 mmoles) of the methyl ester of (+)-8-chloro-6hydroxy-octanoic acid (+)-(VIII) (R=Me) and 0.04 g (0.5 mmoles) of pyridine in 8 ml toluene, 1.6 g (13.5 mmoles) of thionyl chloride in 5 ml of toluene were added slowly. The mixture was then refluxed for 1 hour. After cooling to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | null | HCl | C1(=CC=CC=C1)C | null | null | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>C1(=CC=CC=C1)C>O=C(O)CCCCC(Cl)CCCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7e0a7be4dd4457c99da60d09cb113ab | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>>O=C(O)CCCCC(Cl)CCCl | ClCCC(CCCCC(=O)O)O.N1=CC=CC=C1.S(=O)(Cl)Cl>>ClC(CCCCC(=O)O)CCCl | O[CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])[CH2:10][CH2:11][Cl:12].O=S(Cl)[Cl:9]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([Cl:9])[CH2:10][CH2:11][Cl:12] | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl | O=C(O)CCCCC(Cl)CCCl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6]>>[C:4]-[C:3]-[CH;D3;+0:2](-[Cl;H0;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | null | null | To a solution of 2.9 g (13.2 mmoles) of the methyl ester of (-)-8-chloro-6-hydroxy-octanoic acid (-)-(VIII), (R=Me) and 0.05 g (0.6 mmoles) of pyridine in 10 ml toluene, 1.9 g (16.2 mmoles) of thionyl chloride in 6 ml toluene were added slowly. The mixture was then refluxed for 1 hour. After cooling to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | null | HCl | C1(=CC=CC=C1)C | null | null | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>C1(=CC=CC=C1)C>O=C(O)CCCCC(Cl)CCCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc41cd91f23e45a6ab06f2b380bb0c6e | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>>O=C(O)CCCCC(Cl)CCCl | ClCCC(CCCCC(=O)O)O.N1=CC=CC=C1.S(=O)(Cl)Cl>>ClC(CCCCC(=O)O)CCCl | O[CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])[CH2:10][CH2:11][Cl:12].O=S(Cl)[Cl:9]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([Cl:9])[CH2:10][CH2:11][Cl:12] | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl | O=C(O)CCCCC(Cl)CCCl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6]>>[C:4]-[C:3]-[CH;D3;+0:2](-[Cl;H0;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | 4 | HOUR | To a solution of 2.4 g (12.3 mmoles) of (+)-8-chloro-6-hydroxy-octanoic acid (+)-(VI) and 0.05 g (0.6 mmoles) of pyridine in 30 ml toluene, 3.3 g (27.7 mmoles) of thionyl chloride were added slowly. The mixture was then refluxed for 1 hour. The reaction mixture was cooled to room temperature and added to 50 ml ice wate... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | null | HCl | C1(=CC=CC=C1)C | null | 4 | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>C1(=CC=CC=C1)C>O=C(O)CCCCC(Cl)CCCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-426a0ebf081b4289a13701855d6e1618 | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>>O=C(O)CCCCC(Cl)CCCl | ClCCC(CCCCC(=O)O)O.N1=CC=CC=C1.S(=O)(Cl)Cl>>ClC(CCCCC(=O)O)CCCl | O[CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])[CH2:10][CH2:11][Cl:12].O=S(Cl)[Cl:9]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([Cl:9])[CH2:10][CH2:11][Cl:12] | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl | O=C(O)CCCCC(Cl)CCCl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6]>>[C:4]-[C:3]-[CH;D3;+0:2](-[Cl;H0;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | 4 | HOUR | To a solution of 3.0 g (15.4 mmoles) of (-)-8-chloro-6-hydroxy-octanoic acid (-)-(VI) and 0.06 g (0.8 mmoles) of pyridine in 40 ml toluene, 4.1 g (34.4 mmoles) of thionyl chloride were added slowly. The mixture was then refluxed for 1 hour, cooled to room temperature and added to 60 ml of ice water. The organic phase w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | null | HCl | C1(=CC=CC=C1)C | null | 4 | O=C(O)CCCCC(O)CCCl.O=S(Cl)Cl>C1(=CC=CC=C1)C>O=C(O)CCCCC(Cl)CCCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d4bf2d31e824543ac5f1049cd6477c4 | CC(=O)Nc1ccc(O)cc1.CC(C)(Oc1ccc(N)cc1)C(=O)O>>CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 | NC1=CC=C(OC(C(=O)O)(C)C)C=C1.C(Cl)(Cl)Cl.[OH-].[Na+].C(C)(=O)NC1=CC=C(C=C1)O.CC(=O)C>>N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1 | Oc1ccc(N[C:2]([CH3:1])=[O:3])cc1.[NH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([CH3:11])([CH3:12])[C:13](=[O:14])[OH:15])[cH:16][cH:17]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([CH3:11])([CH3:12])[C:13](=[O:14])[OH:15])[cH:16][cH:17]1 | CC(=O)Nc1ccc(O)cc1.CC(C)(Oc1ccc(N)cc1)C(=O)O | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 | null | null | null | Acylation | OtherReaction | f0587316dec6322bc8536bc1554a2dcfb19ea5ea59546c16f81f49f5f2fb7d70 | 07fa0d1f4d8418421a4320317c5bccf00c4e081ec51f5368bcd2c8236c65866e | c1ccccc1 | O-c1:c:c:c(-N-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):c:c:1.[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 60 | [{"value": 60.0, "product": "N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | FIG. 2A illustrates a reaction scheme for preparing 2-(4-aminophenoxy)-2-methyl propionic acid, a compound that is useful as a precursor in the preparation of Group I compounds. In accordance with the scheme of FIG. 2A, 8 grams (g) (0.2 mol) of pulverized sodium hydroxide is added to a suspension of 5.28 g (0.035 mol) ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol.Primary amine | Secondary amide | c1ccccc1 | null | c1ccccc1 | HO- | null | null | 0.5 | CC(=O)Nc1ccc(O)cc1.CC(C)(Oc1ccc(N)cc1)C(=O)O>>CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5df4ba9dfa614b57afe5f1e9bd2ce8ad | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1>>CC(C)(Oc1ccc(N)cc1)C(=O)O | N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1.C(C)(=O)O>>NC1=CC=C(OC(C(=O)O)(C)C)C=C1 | CC(=O)[NH:9][c:8]1[cH:7][cH:6][c:5]([O:4][C:2]([CH3:1])([CH3:3])[C:12](=[O:13])[OH:14])[cH:11][cH:10]1>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][cH:11]1)[C:12](=[O:13])[OH:14] | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 | CC(C)(Oc1ccc(N)cc1)C(=O)O | null | null | [OH-].[K+] | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 62 | [{"value": 62.0, "product": "NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.5, "product": "NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.18 g (0.005 mol) of the 2-(4-acetaminophenoxy)-2-methyl propionic acid is boiled in 10% KOH (60 ml) for 1/2 hour. The solution is then cooled and acidified with acetic acid to yield 0.6 g (62% yield) of 2-(4-aminophenoxy)-2-methyl propionic acid as a yellowish white powder, mp 214°-16° C.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | [OH-].[K+] | null | null | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1>[OH-].[K+]>CC(C)(Oc1ccc(N)cc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1dc4037cb7e3432d91b32f13bfcb1203 | CC(C)(Oc1ccc(N)cc1)C(=O)O.O=C(Cl)Cc1ccccc1>>CC(C)(Oc1ccc(NC(=O)Cc2ccccc2)cc1)C(=O)O | NC1=CC=C(OC(C(=O)O)(C)C)C=C1.C1(=CC=CC=C1)CC(=O)Cl.O.[OH-].[Na+]>>C1(=CC=CC=C1)CC(=O)NC1=CC=C(OC(C(=O)O)(C)C)C=C1 | [CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:19][cH:20]1)[C:21](=[O:22])[OH:23].Cl[C:10](=[O:11])[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1)[C:21](=[O:2... | CC(C)(Oc1ccc(N)cc1)C(=O)O.O=C(Cl)Cc1ccccc1 | CC(C)(Oc1ccc(NC(=O)Cc2ccccc2)cc1)C(=O)O | null | [OH-].[Na+] | CCOCC.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 57.4 | [{"value": 56.0, "product": "C1(=CC=CC=C1)CC(=O)NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "C1(=CC=CC=C1)CC(=O)NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | FIG. 2C illustrates a general reaction scheme for preparing the Group I 2-[4-(arylacetamido)phenoxy]-2-methyl propionic acids. In accordance with the illustrated scheme, 1 g (0.005 mol) of 2-(4-aminophenoxy)-2-methyl propionic acid is dissolved with stirring in 10 ml of water containing 0.41 g (0.1 mol) of NaOH. To thi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | [OH-].[Na+].CCOCC.O1CCCC1 | null | 1 | CC(C)(Oc1ccc(N)cc1)C(=O)O.O=C(Cl)Cc1ccccc1>[OH-].[Na+].CCOCC.O1CCCC1>CC(C)(Oc1ccc(NC(=O)Cc2ccccc2)cc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-628fb4c02d854452b86ab6726458ce3f | Nc1ccc(Cl)cc1.O=C(O)Cc1ccc(O)cc1>>O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1 | CC(=O)C.P(Cl)(Cl)(Cl)(Cl)Cl.OC1=CC=C(C=C1)CC(=O)O.ClC1=CC=C(N)C=C1>>ClC1=CC=C(NC(=O)CC=2C=C(C=CC2)O)C=C1 | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:10][c:8]([OH:9])[cH:7][cH:6]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | Nc1ccc(Cl)cc1.O=C(O)Cc1ccc(O)cc1 | O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1 | null | null | C(C)C(=O)CC.C1(=CC(=CC(=C1)C)C)C | Acylation | OtherReaction | 4d66d758b08f9f828e782c8e08171e18b46fe11b590da48a7f0ca692ffa62bad | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7](-[O;D1;H1:8]):[c:9]:[cH;D2;+0:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:6]:[c:7](-[O;D1;H1:8]):[c:9]:[cH;D2;+0:10]:[cH;D2;+0:5]:1)-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14] | 90 | [{"value": 90.0, "product": "ClC1=CC=C(NC(=O)CC=2C=C(C=CC2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | FIG. 6b presents a similar reaction scheme to FIG. 6a, except that 3- rather than 4-hydroxyphenylacetic acid (HPAA) is used as the precursor material so that the final compound has a meta rather than a para substitution. In addition, rather than reacting with acetone (dimethyl ketone) a diethyl ketone is used to positi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C(C)C(=O)CC.C1(=CC(=CC(=C1)C)C)C | null | 2 | Nc1ccc(Cl)cc1.O=C(O)Cc1ccc(O)cc1>C(C)C(=O)CC.C1(=CC(=CC(=C1)C)C)C>O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-30b24befdf374a5dae019d09392b25b1 | CC(C)C(=O)O.O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1>>CC(C)(Oc1ccc(CC(=O)Nc2ccc(Cl)cc2)cc1)C(=O)O | C(Cl)(Cl)Cl.ClC1=CC=C(NC(=O)CC=2C=C(C=CC2)O)C=C1.[OH-].[Na+].CC(C(=O)O)C>>ClC1=CC=C(C=C1)NC(=O)CC1=CC=C(OC(C(=O)O)(C)C)C=C1 | [CH3:1][CH:2]([CH3:3])[C:22](=[O:23])[OH:24].[OH:4][c:5]1[cH:6][cH:7][cH:20][c:8]([CH2:9][C:10](=[O:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[cH:21]1>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C:10](=[O:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[cH:20][cH:21]1... | CC(C)C(=O)O.O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1 | CC(C)(Oc1ccc(CC(=O)Nc2ccc(Cl)cc2)cc1)C(=O)O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 025692b3b9d8300828a9105e6358b2c6fdb859a5c9ba0b1ead852eb26168ed5c | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=C(Cc1ccccc1)Nc1ccccc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[O;D1;H0:7]=[C:8](-[#7:9]-[c:10])-[C:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[c:15]:[c:16](-[OH;D1;+0:17]):[cH;D2;+0:18]:1>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[O;H0;D2;+0:17]-[c:16]1:[c:15]:[cH;D2;+0:14]:[c;H0;D3;+0:12](-[C:11]-[C:8]... | null | [] | null | null | 10 | HOUR | FIG. 6b presents a similar reaction scheme to FIG. 6a, except that 3- rather than 4-hydroxyphenylacetic acid (HPAA) is used as the precursor material so that the final compound has a meta rather than a para substitution. In addition, rather than reacting with acetone (dimethyl ketone) a diethyl ketone is used to positi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | CC(=O)C | null | 10 | CC(C)C(=O)O.O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1>CC(=O)C>CC(C)(Oc1ccc(CC(=O)Nc2ccc(Cl)cc2)cc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2f4cd40f5274991995429276bf093da | CC(C)C=O.Cc1cc(C)cc(NC(=O)Cc2ccc(O)cc2)c1.[OH-]>>Cc1cc(C)cc(NC(=O)Cc2ccc(OC(C(=O)O)C(C)C)cc2)c1 | C(C(C)C)=O.C(Cl)(Cl)Cl.CC=1C=C(C=C(C1)C)NC(CC1=CC=C(C=C1)O)=O.[OH-].[Na+].C1CCOC1>>CC(C(C(=O)O)OC1=CC=C(C=C1)CC(=O)NC1=CC(=CC(=C1)C)C)C | [CH:17](=[O:19])[CH:21]([CH3:22])[CH3:23].[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([NH:8][C:9](=[O:10])[CH2:11][c:12]2[cH:13][cH:14][c:15]([OH:16])[cH:24][cH:25]2)[cH:26]1.[OH-:20]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([NH:8][C:9](=[O:10])[CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH:17]([C:18](=[O:19])[OH:... | CC(C)C=O.Cc1cc(C)cc(NC(=O)Cc2ccc(O)cc2)c1.[OH-] | Cc1cc(C)cc(NC(=O)Cc2ccc(OC(C(=O)O)C(C)C)cc2)c1 | null | null | null | Acylation | OtherReaction | 8966c347fe7d5847673f4e4ed6151b3d5564cdfbc4bf493e861b286ffe9eb4a9 | db6cf59fea3528d352436dae74cfe22277bb6bd4271b0c69e59fe259dbb76662 | O=C(Cc1ccccc1)Nc1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5].[OH-;D0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:11](=[O;H0;D1;+0:5])-[OH;D1;+0:6] | 23.5 | [{"value": 23.5, "product": "CC(C(C(=O)O)OC1=CC=C(C=C1)CC(=O)NC1=CC(=CC(=C1)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. 5.45 ml (60 mmol) of isobutyraldehyde and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirring continued overnight at room temperature. THF is removed under vacuu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.c1ccccc1 | null | null | null | 8 | CC(C)C=O.Cc1cc(C)cc(NC(=O)Cc2ccc(O)cc2)c1.[OH-]>>Cc1cc(C)cc(NC(=O)Cc2ccc(OC(C(=O)O)C(C)C)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fbc0fc4f8a714c35aadd804f9ca4453c | Cc1cc(C)cc(NC(=O)Cc2ccc(O)cc2)c1.ClC(Cl)Cl.O=C1CCCCC1>>Cl.O=C(O)C1CCCCC1 | CC=1C=C(C=C(C1)C)NC(CC1=CC=C(C=C1)O)=O.[OH-].[Na+].C1(CCCCC1)=O.C(Cl)(Cl)Cl>>Cl.C1(CCCCC1)C(=O)O | Cc1cc(C)cc(N[C:3](Cc2ccc(O)cc2)=[O:2])c1.ClC(Cl)[Cl:1].[O:4]=[C:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1>>[ClH:1].[O:2]=[C:3]([OH:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | Cc1cc(C)cc(NC(=O)Cc2ccc(O)cc2)c1.ClC(Cl)Cl.O=C1CCCCC1 | Cl.O=C(O)C1CCCCC1 | null | null | C1CCOC1 | Acylation | OtherReaction | a2bf721cf58c03e40a423b16655e17dafb743d2c27059ec129a5414eac9b5efb | 9950a7109cacf615b23644366646aa0d94256a221dca15ba75273b0adc7365b4 | C1CCCCC1 | C-c1:c:c(-C):c:c(-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-C-c2:c:c:c(-O):c:c:2):c:1.Cl-C(-Cl)-[Cl;H0;D1;+0:3].[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[C:9]>>[C:4]-[C:5]-[CH;D3;+0:6](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:7])-[C:8]-[C:9].[ClH;D0;+0:3] | null | [] | null | null | 8 | HOUR | N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. Subsequently 5.889 gms (60 mmol) of cyclohexanone and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirred overnight at room temperature. THF is removed under vacu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Ketone.Secondary amide.Aromatic alcohol | Carboxylic acid | c1ccccc1.c1ccccc1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HCl | C1CCOC1 | null | 8 | Cc1cc(C)cc(NC(=O)Cc2ccc(O)cc2)c1.ClC(Cl)Cl.O=C1CCCCC1>C1CCOC1>Cl.O=C(O)C1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-01039e4c25c144fb9c3dd548ff4937c0 | ClCC1CC1.OCCc1ccc(O)cc1>>Oc1ccc(CCOCC2CC2)cc1 | OC1=CC=C(CCO)C=C1.CC(C)([O-])C.[K+].ClCC1CC1>>C1C(C1)COCCC1=CC=C(C=C1)O | Cl[CH2:9][CH:10]1[CH2:11][CH2:12]1.[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][OH:8])[cH:13][cH:14]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)[cH:13][cH:14]1 | ClCC1CC1.OCCc1ccc(O)cc1 | Oc1ccc(CCOCC2CC2)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccc(CCOCC2CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1 | null | [] | 50 | CELSIUS | 30 | MINUTE | A reaction flask was charged with 4-Hydroxyphenethyl alcohol (1) (100 g, 0.72 mol), Potassium tert-butoxide (243 g, 2.17 mol), and 500 mL of DMSO. The mixture was stirred under nitrogen at 50° C. for 30 minutes. A solution of (Chloromethyl)cyclopropane (100 g, 1.10 mol) in 500 mL of DMSO was added dropwise to the react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1.C1CC1 | HCl | CS(=O)C | 50 | 0.5 | ClCC1CC1.OCCc1ccc(O)cc1>CS(=O)C>Oc1ccc(CCOCC2CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c286a2e885484b41ab2ffed0b7d175fa | ClCC1CO1.Oc1ccc(CCOCC2CC2)cc1>>c1cc(OCC2CO2)ccc1CCOCC1CC1 | C1C(C1)COCCC1=CC=C(C=C1)O.C(Cl)C1CO1>>C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1 | Cl[CH2:5][CH:6]1[CH2:7][O:8]1.[cH:1]1[cH:2][c:3]([OH:4])[cH:9][cH:10][c:11]1[CH2:12][CH2:13][O:14][CH2:15][CH:16]1[CH2:17][CH2:18]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH:6]2[CH2:7][O:8]2)[cH:9][cH:10][c:11]1[CH2:12][CH2:13][O:14][CH2:15][CH:16]1[CH2:17][CH2:18]1 | ClCC1CO1.Oc1ccc(CCOCC2CC2)cc1 | c1cc(OCC2CO2)ccc1CCOCC1CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cc(OCC2CO2)ccc1CCOCC1CC1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | null | null | reaction 4-[(2-Cyclopropylmethoxy)-ethyl]-phenol with epichlorohydrin in presence of base to form 1- {4-[2-(Cyclopropylmethoxy)-ethyl]-phenoxy}-2,3-epoxypropane; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CO1.C1CC1 | HCl | null | null | null | ClCC1CO1.Oc1ccc(CCOCC2CC2)cc1>>c1cc(OCC2CO2)ccc1CCOCC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ba91dbc28c63462ca93bd46a2b37e7f2 | CC(C)N.c1cc(OCC2CO2)ccc1CCOCC1CC1>>CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1 | C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1.C(C)(C)N>>CC(C)NCC(COC=1C=CC(=CC1)CCOCC2CC2)O | [CH3:1][CH:2]([CH3:3])[NH2:4].[CH2:5]1[CH:6]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH2:15][O:16][CH2:17][CH:18]3[CH2:19][CH2:20]3)[cH:21][cH:22]2)[O:7]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH:6]([OH:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][CH2:15][O:16][CH2:17][CH:18]2[CH2:19][CH2:20]2)[cH:21][cH... | CC(C)N.c1cc(OCC2CO2)ccc1CCOCC1CC1 | CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(CCOCC2CC2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[C:5]-[C:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[C:5]-[C:6](-[OH;D1;+0:8])-[CH2;D2;+0:7]-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | null | [] | null | null | null | null | reacting 1-{4-[2-(Cyclopropylmethoxy)ethyl]phenoxy}-2,3-epoxypropane with isopropylamine to produce Betaxolol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.C1CC1 | null | null | null | null | CC(C)N.c1cc(OCC2CO2)ccc1CCOCC1CC1>>CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3621f94f482749a0aab619c530182860 | ClCC1CO1.Oc1ccc(CCOCC2CC2)cc1>>c1cc(OCC2CO2)ccc1CCOCC1CC1 | C1C(C1)COCCC1=CC=C(C=C1)O.C(Cl)C1CO1>>C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1 | Cl[CH2:5][CH:6]1[CH2:7][O:8]1.[cH:1]1[cH:2][c:3]([OH:4])[cH:9][cH:10][c:11]1[CH2:12][CH2:13][O:14][CH2:15][CH:16]1[CH2:17][CH2:18]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH:6]2[CH2:7][O:8]2)[cH:9][cH:10][c:11]1[CH2:12][CH2:13][O:14][CH2:15][CH:16]1[CH2:17][CH2:18]1 | ClCC1CO1.Oc1ccc(CCOCC2CC2)cc1 | c1cc(OCC2CO2)ccc1CCOCC1CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cc(OCC2CO2)ccc1CCOCC1CC1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | null | null | reaction 4-[(2-Cyclopropylmethoxy)-ethyl]-phenol with epichlorohydrin in presence of base to form 1-{4-[2-(Cyclopropylmethoxy)-ethyl]-phenoxy}-2,3-epoxypropane;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CO1.C1CC1 | HCl | null | null | null | ClCC1CO1.Oc1ccc(CCOCC2CC2)cc1>>c1cc(OCC2CO2)ccc1CCOCC1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68c25eceade145838696ca87a1c247b2 | CC(C)N.c1cc(OCC2CO2)ccc1CCOCC1CC1>>CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1 | C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1.C(C)(C)N>>CC(C)NCC(COC=1C=CC(=CC1)CCOCC2CC2)O | [CH3:1][CH:2]([CH3:3])[NH2:4].[CH2:5]1[CH:6]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH2:15][O:16][CH2:17][CH:18]3[CH2:19][CH2:20]3)[cH:21][cH:22]2)[O:7]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH:6]([OH:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][CH2:15][O:16][CH2:17][CH:18]2[CH2:19][CH2:20]2)[cH:21][cH... | CC(C)N.c1cc(OCC2CO2)ccc1CCOCC1CC1 | CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc(CCOCC2CC2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[C:5]-[C:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[C:5]-[C:6](-[OH;D1;+0:8])-[CH2;D2;+0:7]-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | null | [] | null | null | null | null | reacting 1-{4-[2-(Cyclopropylmethoxy)ethyl]phenoxy}-2,3-epoxypropane with isopropylamine to produce Betaxolol; and
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.C1CC1 | null | null | null | null | CC(C)N.c1cc(OCC2CO2)ccc1CCOCC1CC1>>CC(C)NCC(O)COc1ccc(CCOCC2CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5e03f22df256414685d3dd552140fa88 | CCOC(=O)CC(=O)c1ccc(OC)cc1.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2>>CCOC(=O)C(C(=O)c1ccc(OC)cc1)C(CC[N+](=O)[O-])c1ccc2c(c1)OCO2 | C(C)OC(CC(C1=CC=C(C=C1)OC)=O)=O.C(C)(=O)OCC.C1(=CC=CC=C1)C.[N+](=O)([O-])C=CC1=CC2=C(OCO2)C=C1.C1(=CC=CC=C1)C>>COC1=CC=C(C(=O)C(C(=O)OCC)C(CC[N+](=O)[O-])C2=CC3=C(OCO3)C=C2)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1.[c:17]1([CH:18]=[CH:19][N+:20](=[O:21])[O-:22])[cH:24][cH:25][c:26]2[c:27]([cH:28]1)[O:29][CH2:30][O:31]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c... | CCOC(=O)CC(=O)c1ccc(OC)cc1.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2 | CCOC(=O)C(C(=O)c1ccc(OC)cc1)C(CC[N+](=O)[O-])c1ccc2c(c1)OCO2 | null | N12CCCCCC2=NCCC1.N12CCCCCC2=NCCC1 | C(Cl)Cl | C-C Coupling | OtherReaction | a63c55febfbfd717c2d410575850c839b0a8ad395f0e0803e0b81bd77c6c8859 | 4652ebdea1fa74679a2753b2c3d8e4bdb2ddfc9067198bef14270d9d75ac279c | O=C(CCc1ccc2c(c1)OCO2)c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8].[O;-;D1;H0:9]-[#7;+:10](=[O;D1;H0:11])-[CH;D2;+0:12]=[CH;D2;+0:13]-[c;H0;D3;+0:14]1:[cH;D2;+0:15]:[c:16]:[c:17]2:[c:18](:[cH;D2;+0:19]:1)-[#8:20]-[C:21]-[#8:22]-2>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:6](=[O;D1;H0:7])-[c:8])-[CH;D3;+0... | null | [] | 80 | CELSIUS | null | null | To ethyl(4-methoxybenzoyl)acetate (23.0 g, 0.104 mol), prepared by the method of Krapcho et al., Org. Syn. 47, 20 (1967), and 5-(2-nitrovinyl)-1,3-benzodioxole (17.0 g, 0.088 mol) dissolved in 180 mL of toluene and heated to 80° C. was added 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 0.65 g) with stirring. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Ester | Ketone.Ester.Nitro group | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | Other | N12CCCCCC2=NCCC1.N12CCCCCC2=NCCC1.C(Cl)Cl | 80 | null | CCOC(=O)CC(=O)c1ccc(OC)cc1.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2>N12CCCCCC2=NCCC1.N12CCCCCC2=NCCC1.C(Cl)Cl>CCOC(=O)C(C(=O)c1ccc(OC)cc1)C(CC[N+](=O)[O-])c1ccc2c(c1)OCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7daf333146d4b1e9607ee1dc94808ae | C[N+](=O)[O-].O=Cc1ccc2c(c1)OCO2>>O=[N+]([O-])/C=C/c1ccc2c(c1)OCO2 | C1=CC2=C(C=C1C=O)OCO2.[N+](=O)([O-])C.[OH-].[Na+].Cl>>C1OC=2C=C(/C=C/[N+](=O)[O-])C=CC2O1 | [O:1]=[N+:2]([O-:3])[CH3:4].O=[CH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[O:12][CH2:13][O:14]2>>[O:1]=[N+:2]([O-:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[O:12][CH2:13][O:14]2 | C[N+](=O)[O-].O=Cc1ccc2c(c1)OCO2 | O=[N+]([O-])/C=C/c1ccc2c(c1)OCO2 | null | null | CO.O | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccc2c(c1)OCO2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 55 | [{"value": 55.0, "product": "C1OC=2C=C(/C=C/[N+](=O)[O-])C=CC2O1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.9, "product": "C1OC=2C=C(/C=C/[N+](=O)[O-])C=CC2O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred solution of piperonal (75 g, 500 mmol) in methanol (120 mL) at 10° C. was added nitromethane (27.1 mL, 500 mmol, 1 eq) followed by the dropwise addition of sodium hydroxide (21 g, 525 mmol, 1.05 eq) in sufficient water to achieve a total volume of 50 mL while maintaining the temperature between 10°-15° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccc2c(c1)OCO2 | HO- | CO.O | null | 0.5 | C[N+](=O)[O-].O=Cc1ccc2c(c1)OCO2>CO.O>O=[N+]([O-])/C=C/c1ccc2c(c1)OCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a77e34e2ec91434fa697b43c33d45133 | c1ccc2c(c1)CCO2>>O=Cc1ccc2c(c1)CCO2 | O1CCC2=C1C=CC=C2.COC(Cl)Cl>>O1CCC2=C1C=CC(=C2)C=O | [cH:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][O:11]2>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][O:11]2 | c1ccc2c(c1)CCO2 | O=Cc1ccc2c(c1)CCO2 | null | null | CCOCC.C(Cl)Cl | Miscellaneous | OtherReaction | c575f431b3127090be8382568230b261240de97350cb8e70e8cf496a0db5ebef | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccc2c(c1)CCO2 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]:[c:5]>>[O;D1;H0:6]=[C:7]-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]:[c:5] | 60.3 | [{"value": 60.0, "product": "O1CCC2=C1C=CC(=C2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "O1CCC2=C1C=CC(=C2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a stirred solution of α,α-dichloromethyl methyl ether (2.15 g, 19 mmol, 1.35 eq) in methylene chloride (30 mL) at -40° C. was added successively stannic chloride (1.65 g, 17 mmol, 1.2 eq) and 15 minutes later, a solution of 2,3-dihydrobenzofuran (1.68 g, 14 mmol) in CH2Cl2 (5 mL) maintaining the temperature at or be... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | Other | CCOCC.C(Cl)Cl | 0 | 1 | c1ccc2c(c1)CCO2>CCOCC.C(Cl)Cl>O=Cc1ccc2c(c1)CCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9216403abe2a471cb8b491c2ec69c28c | CCCC(CCC)C(=O)O.Cl>>CCCC(CCC)C(=O)CCl | [N+](=[N-])=C.Cl.O1CCOCC1.C(C(=O)Cl)(=O)Cl.C(CC)C(C(=O)O)CCC>>ClCC(C(CCC)CCC)=O | O[C:8]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9].[ClH:11]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[CH2:10][Cl:11] | CCCC(CCC)C(=O)O.Cl | CCCC(CCC)C(=O)CCl | null | null | ClCCl.CN(C)C=O | C-C Coupling | OtherReaction | a88a538b7ccbd80769a19dc61ba7a4c471b9d5294566a11e2f34cd0c85bd2ed2 | 55e89b9a967dd11f3d24b505d358c78d986ed007c8a7b35e0472c2b81cdbe7d6 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[ClH;D0;+0:6]>>[C:4]-[C:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:7]-[Cl;H0;D1;+0:6] | null | [] | 0 | CELSIUS | 18 | HOUR | To 2-propylpentanoic acid (156.6 μl, 1.00 mmol) dissolved in anhydrous dichloromethane (2 mL) was added DMF (3 μL, 4 mole %), and the solution was cooled to 0° C. under a nitrogen atmosphere. To the solution was added oxalyl chloride (94.3 μL, 1.08 mmol) dropwise over a few minutes. The reaction was stirred 18 hours wh... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary halide.Ketone | null | null | null | null | ClCCl.CN(C)C=O | 0 | 18 | CCCC(CCC)C(=O)O.Cl>ClCCl.CN(C)C=O>CCCC(CCC)C(=O)CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a43f21651da24fe980f402c4a2514be5 | CC=CCCC(=O)CC(=O)OC.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2>>CC=CCCC(=O)C(C(=O)OC)C(C[N+](=O)[O-])c1ccc2c(c1)OCO2 | O=C(CC(=O)OC)CCC=CC.[N+](=O)([O-])C=CC1=CC2=C(OCO2)C=C1.C(C)(=O)OCC.CCCCCC>>C(CCC=CC)(=O)C(C(=O)OC)C(C[N+](=O)[O-])C1=CC2=C(OCO2)C=C1 | [CH3:1][CH:2]=[CH:3][CH2:4][CH2:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[O:11][CH3:12].[CH:13](=[CH:14][N+:15](=[O:16])[O-:17])[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][O:26]2>>[CH3:1][CH:2]=[CH:3][CH2:4][CH2:5][C:6](=[O:7])[CH:8]([C:9](=[O:10])[O:11][CH3:12])[CH:13]([CH2:14][N+:15](=[O:16])[O-:17])[c:18]1... | CC=CCCC(=O)CC(=O)OC.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2 | CC=CCCC(=O)C(C(=O)OC)C(C[N+](=O)[O-])c1ccc2c(c1)OCO2 | null | C1CCC2=NCCCN2CC1 | C(C)(C)O.C1CCOC1 | C-C Coupling | Michael addition | 78592dd0b65ee51b61909e39c62f9c065e02236b9cc01c910f5062287d6763bc | ab6a9edd4f7bf4a62d0b4eb9db37e0264a97273a347adf154936153225c1e329 | c1ccc2c(c1)OCO2 | [C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].[O;-;D1;H0:9]-[#7;+:10](=[O;D1;H0:11])-[CH;D2;+0:12]=[CH;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])-[CH;D3;+0:13](-[CH2;D2;+0:12]-[#7;+:10](-[O;-;D1;H0:9])=[O;D1;H0:11])-... | 82 | [{"value": 82.0, "product": "C(CCC=CC)(=O)C(C(=O)OC)C(C[N+](=O)[O-])C1=CC2=C(OCO2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "C(CCC=CC)(=O)C(C(=O)OC)C(C[N+](=O)[O-])C1=CC2=C(OCO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of methyl 3-oxo-6-octenoate (502 mg, 2.95 mmol) in 10 mL of isopropanol was added to a solution of 5-(2-nitrovinyl)-1,3-benzodioxole (712 mg, 3.69 mmol) in 10 mL THF, then DBU (22 μL, 0.15 mmol) was added. The resulting reddish solution was stirred at room temperature for 20 minutes. TLC (ethyl acetate-hexan... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone | Ketone.Ester.Nitro group | null | null | c1ccc2c(c1)OCO2 | null | C1CCC2=NCCCN2CC1.C(C)(C)O.C1CCOC1 | null | 0.333333 | CC=CCCC(=O)CC(=O)OC.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2>C1CCC2=NCCCN2CC1.C(C)(C)O.C1CCOC1>CC=CCCC(=O)C(C(=O)OC)C(C[N+](=O)[O-])c1ccc2c(c1)OCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ffd6541cc5d749e1855a0974ed600183 | C1=COCC1.CC(=O)Cl>>CC(=O)c1ccc2c(c1)CCO2 | O1CCC=C1.C(C)(=O)Cl>>C(C)(=O)C=1C=CC2=C(CCO2)C1 | [CH2:4]1[CH:6]=[CH:7][O:12][CH2:11]1.Cl[C:2]([CH3:1])=[O:3]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][O:12]2 | C1=COCC1.CC(=O)Cl | CC(=O)c1ccc2c(c1)CCO2 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 7c9b39299a35adb64f40e2004e842aa35eb58963a5eed91c604baee2b536409f | 78af1ccd18c432da7226d1eb9452ce663384f9111077a903124847a8f0f30a9a | c1ccc2c(c1)CCO2 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]1-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH;D2;+0:7]=[CH;D2;+0:8]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6]1:[c:9]:[cH;D2;+0:7]:[c;H0;D3;+0:8]2:[c:10](:[c:11]:1)-[C:12]-[CH2;D2;+0:5]-[#8:4]-2 | 186.7 | [{"value": 93.0, "product": "C(C)(=O)C=1C=CC2=C(CCO2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 186.7, "product": "C(C)(=O)C=1C=CC2=C(CCO2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a 0° C. solution of acetyl chloride (1.64 mL, 23.0 mmol, 1.3 equivalents) in methylene chloride (30 mL) was added stannic chloride (2.49 mL, 21.3 mmol, 1.2 equivalents), maintaining the temperature below 5° C. The solution was stirred 15 minutes at 0° C., and then a solution of 2,3-dihydrofuran (2.00 mL, 17.7 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ketone.Ether | C1=COCC1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | C(Cl)Cl | 0 | 0.25 | C1=COCC1.CC(=O)Cl>C(Cl)Cl>CC(=O)c1ccc2c(c1)CCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7dbf314416104f6e992b4a9d5e3d2526 | CCOC(=O)OCC.COc1ccc(C(C)=O)cc1>>CCOC(=O)CC(=O)c1ccc(OC)cc1 | [H-].[Na+].CC(=O)C1=CC=C(C=C1)OC.C(C)(=O)C1=CC=CC=C1.C(C)(=O)O.C(OCC)(OCC)=O>>COC1=CC=C(C=C1)C(CC(=O)OCC)=O | CCO[C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH3:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1 | CCOC(=O)OCC.COc1ccc(C(C)=O)cc1 | CCOC(=O)CC(=O)c1ccc(OC)cc1 | null | null | C1(=CC=CC=C1)C.O | C-C Coupling | OtherReaction | 984c35cff4b3f334715b1696c3f8f2fb17ccd67fc374fcef5afdd55b5aabecf9 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8] | null | [] | null | null | 5 | MINUTE | Simultaneous reactions were run in both a 65-L reactor and a 35-L reactor that share the same reflux system. A nitrogen atmosphere was maintained in both. 4.0 kg (100 moles) of 60% sodium hydride in mineral oil and 32 L toluene were charged into the ambient temperature reactors. The mixture was agitated for 5 minutes a... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C.O | null | 0.083333 | CCOC(=O)OCC.COc1ccc(C(C)=O)cc1>C1(=CC=CC=C1)C.O>CCOC(=O)CC(=O)c1ccc(OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f03c70e534504a4d9fbd8ac5c0c335af | C[N+](=O)[O-].O=Cc1ccc2c(c1)OCO2>>O=[N+]([O-])C=Cc1ccc2c(c1)OCO2 | [OH-].[Na+].C1=CC2=C(C=C1C=O)OCO2.[N+](=O)([O-])C>>C1OC=2C=C(C=CC2O1)C=C[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[CH3:4].O=[CH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[O:12][CH2:13][O:14]2>>[O:1]=[N+:2]([O-:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[O:12][CH2:13][O:14]2 | C[N+](=O)[O-].O=Cc1ccc2c(c1)OCO2 | O=[N+]([O-])C=Cc1ccc2c(c1)OCO2 | null | null | CO.O | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccc2c(c1)OCO2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 4 | CELSIUS | 30 | MINUTE | In a 45-L cryogenic reactor with a contoured, anchor stirrer was dissolved 5.537 kg (36.9 moles) piperonal in 9 L methanol and 2.252 kg (36.9 moles) nitromethane at 15°-20° C. The jacket temperature was set to -5° C. and the reaction solution cooled to a temperature of +3.5° C. A 21° C. solution of 3.10 kg (38.8 moles)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccc2c(c1)OCO2 | HO- | CO.O | 4 | 0.5 | C[N+](=O)[O-].O=Cc1ccc2c(c1)OCO2>CO.O>O=[N+]([O-])C=Cc1ccc2c(c1)OCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-89e91895296b44e384eadd8c11cead93 | CCOC(=O)CC(=O)c1ccc(OC)cc1.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2>>CCOC(=O)C(C(=O)c1ccc(OC)cc1)C(C[N+](=O)[O-])c1ccc2c(c1)OCO2 | N12CCCCCC2=NCCC1.COC1=CC=C(C=C1)C(CC(=O)OCC)=O.C1OC=2C=C(C=CC2O1)C=C[N+](=O)[O-]>>COC1=CC=C(C(=O)C(C(=O)OCC)C(C[N+](=O)[O-])C2=CC3=C(C=C2)OCO3)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1.[CH:17](=[CH:18][N+:19](=[O:20])[O-:21])[c:22]1[cH:23][cH:24][c:25]2[c:26]([cH:27]1)[O:28][CH2:29][O:30]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c... | CCOC(=O)CC(=O)c1ccc(OC)cc1.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2 | CCOC(=O)C(C(=O)c1ccc(OC)cc1)C(C[N+](=O)[O-])c1ccc2c(c1)OCO2 | null | null | C(C)(=O)OCC | C-C Coupling | Michael addition | 78592dd0b65ee51b61909e39c62f9c065e02236b9cc01c910f5062287d6763bc | ab6a9edd4f7bf4a62d0b4eb9db37e0264a97273a347adf154936153225c1e329 | O=C(CCc1ccc2c(c1)OCO2)c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8].[O;-;D1;H0:9]-[#7;+:10](=[O;D1;H0:11])-[CH;D2;+0:12]=[CH;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:6](=[O;D1;H0:7])-[c:8])-[CH;D3;+0:13](-[CH2;D2;+0:12]-[#7;+:10](-[O;-;D1;H0:9])=[O;D1;H0:11])-[c:14](:[c:1... | null | [] | null | null | null | null | Into a 45-L stirred reactor at ambient temperature were charged 5.819 kg (30.1 moles) 3,4-methylenedioxy-1-(2-nitroethenyl)-benzene and 24 L ethyl acetate. A solution of 5.355 kg (24.1 moles) ethyl 3-(4-methoxyphenyl)-3-oxopropionate in 16 L ethyl acetate was added. 280 g (275 ml, 1.84 moles) of 1,8-diaza-bicyclo[5.4.0... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone | Ketone.Ester.Nitro group | null | null | c1ccccc1.c1ccc2c(c1)OCO2 | null | C(C)(=O)OCC | null | null | CCOC(=O)CC(=O)c1ccc(OC)cc1.O=[N+]([O-])C=Cc1ccc2c(c1)OCO2>C(C)(=O)OCC>CCOC(=O)C(C(=O)c1ccc(OC)cc1)C(C[N+](=O)[O-])c1ccc2c(c1)OCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cc2851f5ea1a4929ac56dab75ef1b205 | CCOC(=O)C1C(c2ccc(OC)cc2)=NCC1c1ccc2c(c1)OCO2>>CCOC(=O)C1C(c2ccc3c(c2)OCO3)CNC1c1ccc(OC)cc1 | C(#N)[BH3-].[Na+].Cl.COC1=CC=C(C=C1)C1=NCC(C1C(=O)OCC)C1=CC2=C(C=C1)OCO2>>COC1=CC=C(C=C1)C1NCC(C1C(=O)OCC)C1=CC2=C(C=C1)OCO2 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]([c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[O:14][CH2:15][O:16]3)[CH2:17][N:18]=[C:19]1[c:20]1[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]([c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[O:14][CH2:15][O:16]3)[CH2:17][NH:18][CH... | CCOC(=O)C1C(c2ccc(OC)cc2)=NCC1c1ccc2c(c1)OCO2 | CCOC(=O)C1C(c2ccc3c(c2)OCO3)CNC1c1ccc(OC)cc1 | null | CC1=C(C=C(C(=C1Br)O)Br)C2(C=3C=CC=CC3S(=O)(=O)O2)C=4C=C(C(=C(C4C)Br)O)Br | C(C)O | Reduction | OtherReaction | 6601a56bbc4a2cc51a03708618f04052b1e0a9a4ea35a474eb1fd3a3948e96ab | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | c1ccc(C2CC(c3ccc4c(c3)OCO4)CN2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]-[C:7]-[N;H0;D2;+0:8]=[C;H0;D3;+0:9]-1-[c:10](:[c:11]):[c:12]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[CH;D3;+0:9]-1-[c:10](:[c:11]):[c:12] | 96.8 | [{"value": 96.8, "product": "COC1=CC=C(C=C1)C1NCC(C1C(=O)OCC)C1=CC2=C(C=C1)OCO2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Into a 12-L flask equipped with magnetic stirring, addition funnel, temperature probe, and nitrogen inlet was charged 0.460 kg ethyl 2-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4,5-dihydro-3H -pyrrole-3-carboxylate (1.25 mol). The reaction vessel was degassed with nitrogen. Absolute 3.7 L ethanol and 1.12 L of THF... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | C1=NCCC1 | C1CCNC1 | C1CCNC1.c1ccc2c(c1)OCO2.c1ccccc1 | null | CC1=C(C=C(C(=C1Br)O)Br)C2(C=3C=CC=CC3S(=O)(=O)O2)C=4C=C(C(=C(C4C)Br)O)Br.C(C)O | null | 0.5 | CCOC(=O)C1C(c2ccc(OC)cc2)=NCC1c1ccc2c(c1)OCO2>CC1=C(C=C(C(=C1Br)O)Br)C2(C=3C=CC=CC3S(=O)(=O)O2)C=4C=C(C(=C(C4C)Br)O)Br.C(C)O>CCOC(=O)C1C(c2ccc3c(c2)OCO3)CNC1c1ccc(OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8461c7f0620f4c95ae6a995e75ca2bad | CC(=O)OC1C=Cc2ccccc21.CC(C)=O>>CC(=O)O[C@H]1C=Cc2ccccc21.O[C@@H]1C=Cc2ccccc21 | C(C)(=O)OC1C=CC2=CC=CC=C12.CC(=O)C>>C(C)(=O)O[C@H]1C=CC2=CC=CC=C12.[C@H]1(C=CC2=CC=CC=C12)O | [CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH:6]=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21.[O:14]=[C:15]([CH3:16])[CH3:23]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH:6]=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21.[OH:14][C@@H:15]1[CH:16]=[CH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21 | CC(=O)OC1C=Cc2ccccc21.CC(C)=O | CC(=O)O[C@H]1C=Cc2ccccc21.O[C@@H]1C=Cc2ccccc21 | null | null | P(=O)([O-])([O-])[O-] | C-C Coupling | OtherReaction | d922d81e30c02698529b5ebf11944e992f45b0edecf65f13fbb0d16f5177cbe1 | e1209d2ea55b3285252e47984246e99f6bf72d06c47f658ccc932ed7a33cc970 | C1=Cc2ccccc2C1.C1=Cc2ccccc2C1 | [CH3;D1;+0:1]-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;H0;D1;+0:4]>>[OH;D1;+0:4]-[C@@H;D3;+0:2]1-[CH;D2;+0:1]=[C:5]-[c:6](:[c:7]):[c;H0;D3;+0:3]-1:[c:8]:[c:9] | 46.1 | [{"value": 44.6, "product": "C(C)(=O)O[C@H]1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.1, "product": "[C@H]1(C=CC2=CC=CC=C12)O", "details": "PERCENTYIELD", "is_desired": false}] | 37 | CELSIUS | 48 | HOUR | 1.0 g (5.75 mmol) of racemic 1-acetoxyindene and 57.5 mg of lipase PS (made by Amano Seiyaku Sha, derived from Pseudomonas bacterium) were suspended in 58 ml of phosphate buffer (0.1M)-acetone mixed solution (9:1 V/V) and stirred at 37° C. for 48 hours. The reaction solution was filtered on Celite to remove lipase. The... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1.C1=Cc2ccccc2C1 | Other | P(=O)([O-])([O-])[O-] | 37 | 48 | CC(=O)OC1C=Cc2ccccc21.CC(C)=O>P(=O)([O-])([O-])[O-]>CC(=O)O[C@H]1C=Cc2ccccc21.O[C@@H]1C=Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a52c34c433e043df8e5ada85e1f85e19 | C=COC(C)=O.OC1C=Cc2ccccc21>>CC(=O)O[C@@H]1C=Cc2ccccc21.O[C@H]1C=Cc2ccccc21 | C1(C=CC2=CC=CC=C12)O.C(C)(=O)OC=C>>C(C)(=O)O[C@@H]1C=CC2=CC=CC=C12.[C@@H]1(C=CC2=CC=CC=C12)O | [CH3:1][C:2](=[O:3])[O:4][CH:11]=[CH2:5].[OH:14][CH:15]1[CH:16]=[CH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH:6]=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21.[OH:14][C@H:15]1[CH:16]=[CH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21 | C=COC(C)=O.OC1C=Cc2ccccc21 | CC(=O)O[C@@H]1C=Cc2ccccc21.O[C@H]1C=Cc2ccccc21 | null | null | C(C)(C)(C)OC | Aromatic Heterocycle Formation | Transesterification | 095962ef03069584f3d6236025c3cc13c630a748c18b32c6275ef7d00ca1ac23 | 1c252658b75f48af10f505b14baa8fc4445be7ff1e240fac6cd4c913596aa367 | C1=Cc2ccccc2C1.C1=Cc2ccccc2C1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH;D2;+0:5]=[CH2;D1;+0:6]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C@@H;D3;+0:6]1-[C:7]=[C:8]-[c:9]2:[c:10]:[c:11]:[cH;D2;+0:5]:[c:12]:[c:13]:2-1 | 38 | [{"value": 38.0, "product": "C(C)(=O)O[C@@H]1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.0, "product": "[C@@H]1(C=CC2=CC=CC=C12)O", "details": "PERCENTYIELD", "is_desired": false}] | 37 | CELSIUS | 7 | DAY | 100 mg (0.76 mmol) of racemic inden-1-ol, 0.13 mg (1.15 mmol) of vinyl acetate and 75.6 mg (100 mg of racemate/mmol) of lipase PS were suspended in 10 ml of t-butylmethyl ether and stirred at 37° C. for 7 days. After the end of the reaction, the suspension was filtered off to remove lipase. The filtrate was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1.C1=Cc2ccccc2C1 | Other | C(C)(C)(C)OC | 37 | 168 | C=COC(C)=O.OC1C=Cc2ccccc21>C(C)(C)(C)OC>CC(=O)O[C@@H]1C=Cc2ccccc21.O[C@H]1C=Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9afdcd5c41e54866bb140805a4791d37 | NCCN.O=C(O)/C=C\C(=O)O.[OH-]>>O=C(O)CC(NCCNC(CC(=O)O)C(=O)O)C(=O)O | C(\C=C/C(=O)O)(=O)O.Cl.C(CN)N.[OH-].[Na+]>>C(CNC(CC(=O)O)C(=O)O)NC(CC(=O)O)C(=O)O | [CH2:5]([NH2:6])[CH2:15][NH2:9].[O:1]=[C:2]([OH:3])/[CH:4]=[CH:11]\[C:12](=[O:13])[OH:14].[OH-:16]>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([NH:6][CH2:7][CH2:8][NH:9][CH:10]([CH2:11][C:12](=[O:13])[OH:14])[C:15](=[O:16])[OH:17])[C:18](=[O:19])[OH:20] | NCCN.O=C(O)/C=C\C(=O)O.[OH-] | O=C(O)CC(NCCNC(CC(=O)O)C(=O)O)C(=O)O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 5c5931eda1d6ff3431a54a5c4d75321ec4c63306e9d0945ecee8722f26cda564 | 3aef9ccf2f5fbebe99bf05c11e97960293a788b684303d235dff5eed5458d0ff | null | [NH2;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4].[O;D1;H0:5]=[C:6](-[O;D1;H1:7])/[CH;D2;+0:8]=[CH;D2;+0:9]\[C:10](=[O;D1;H0:11])-[O;D1;H1:12].[OH-;D0:13]>>[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[CH2;D2;+0:8]-[C:14](-[NH;D2;+0:4]-[C:15]-[C:16]-[NH;D2;+0:1]-[CH;D3;+0:2](-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-... | null | [] | 140 | CELSIUS | null | null | A beaker was charged with maleic acid (120.5 g, 1.03 mole); deionized water (120 g); and 50 percent aqueous NaOH (167 g, 2.08 mole). The mixture was stirred until dissolution occurred; the resulting solution was transferred to a 1-liter, stainless-steel autoclave, using 40 g deionized water as a rinse. Ethylenediamine ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Carboxylic acid.Carboxylic acid.Secondary amine.Secondary amine | null | null | null | null | O | 140 | null | NCCN.O=C(O)/C=C\C(=O)O.[OH-]>O>O=C(O)CC(NCCNC(CC(=O)O)C(=O)O)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e8deb101489c4e02b8ab82ed05f8e3e0 | CC(C)C=C=O.FC(F)(F)C(Cl)Br>>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | CC(C)([O-])C.[Na+].BrC(C(F)(F)F)Cl.CC(C=C=O)C.O1CCCC1>>BrC(C(C=C(C)C)O)(C(F)(F)F)Cl | [CH3:1][CH:2]([CH3:3])[CH:4]=[C:5]=[O:6].[CH:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH:5]([OH:6])[C:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13] | CC(C)C=C=O.FC(F)(F)C(Cl)Br | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | null | null | CN(C=O)C | C-C Coupling | OtherReaction | a555a0218c8ffda0a8d9ad72f436a897605d75c2ecc35d1571cb0a895708f2b6 | c0aafa762e8e97773a571cd9698e9eec9342bb07704960a5a3263af845ada306 | null | [Br;D1;H0:1]-[CH;D3;+0:2](-[Cl;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[C;D1;H3:8]-[CH;D3;+0:9](-[C;D1;H3:10])-[CH;D2;+0:11]=[C;H0;D2;+0:12]=[O;H0;D1;+0:13]>>[Br;D1;H0:1]-[C;H0;D4;+0:2](-[Cl;D1;H0:3])(-[CH;D3;+0:12](-[OH;D1;+0:13])-[CH;D2;+0:11]=[C;H0;D3;+0:9](-[C;D1;H3:8])-[C;D1;H3:10])-[C:4](-[F;D1;H0... | null | [] | -78 | CELSIUS | 40 | MINUTE | Sodium t-butoxide (1.39 g of a 42% solution in dry dimethyl formamide was added dropwise over a period of 5 minutes to a stirred mixture of 1-bromo-1-chloro-2,2,2-trifluoroethane (0.535 ml), 3-methylbut-1-en-1-al (0.538 ml) and dry tetrahydrofuran (10 ml) maintained at a temperature of -78° C. by external cooling under... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Tertiary halide.Tertiary halide.Secondary alcohol | null | null | null | null | CN(C=O)C | -78 | 0.666667 | CC(C)C=C=O.FC(F)(F)C(Cl)Br>CN(C=O)C>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c5c150db0d6042c384ac6e15e60907af | CC(C)=CC=O.FC(F)(F)C(Cl)Br>>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | BrC(C(F)(F)F)Cl.C(C=C(C)C)=O.CC(C)([O-])C.[Na+]>>BrC(C(C=C(C)C)O)(C(F)(F)F)Cl | [CH3:1][C:2]([CH3:3])=[CH:4][CH:5]=[O:6].[CH:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH:5]([OH:6])[C:7]([Cl:8])([Br:9])[C:10]([F:11])([F:12])[F:13] | CC(C)=CC=O.FC(F)(F)C(Cl)Br | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 5435d0ec6b37aa9738fb0b43202d46adad1fb62e47985a626acc8e0a0b0a1203 | cb00fcdc041dbd2da5d224bc1b019b9ae570e5bc5d8f0a5146770346817407c6 | null | [Br;D1;H0:1]-[CH;D3;+0:2](-[Cl;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])=[C:11]-[CH;D2;+0:12]=[O;H0;D1;+0:13]>>[Br;D1;H0:1]-[C;H0;D4;+0:2](-[Cl;D1;H0:3])(-[CH;D3;+0:12](-[OH;D1;+0:13])-[C:11]=[C:9](-[C;D1;H3:8])-[C;D1;H3:10])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7] | 73.8 | [{"value": 70.0, "product": "BrC(C(C=C(C)C)O)(C(F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "BrC(C(C=C(C)C)O)(C(F)(F)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -60 | CELSIUS | null | null | Tetrahydrofuran (230 ml) and sodium t-butoxide (57.6 g; 40% w/v solution in dimethylformamide) was charged to a split-neck reaction flask, and cooled to -60° C. with stirring. 1-Bromo-1-chloro-2,2,2-trifluorethane (47.6 g) and senecialdehyde (20.9 g) were charged simultaneously over 25 minutes, then the mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Aldehyde | Tertiary halide.Tertiary halide.Secondary alcohol | null | null | null | null | O1CCCC1 | -60 | null | CC(C)=CC=O.FC(F)(F)C(Cl)Br>O1CCCC1>CC(C)=CC(O)C(Cl)(Br)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5232ccbb96cf4bf19ed922c74f60ad33 | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>>COC(C)(OC)OC(C=C(C)C)C(Cl)(Br)C(F)(F)F | BrC(C(C=C(C)C)O)(C(F)(F)F)Cl.C(C)(OC)(OC)OC.C(C(C)C)(=O)O>>BrC(C(C=C(C)C)OC(C)(OC)OC)(C(F)(F)F)Cl | [OH:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH3:12])[C:13]([Cl:14])([Br:15])[C:16]([F:17])([F:18])[F:19].CO[C:3]([O:2][CH3:1])([CH3:4])[O:5][CH3:6]>>[CH3:1][O:2][C:3]([CH3:4])([O:5][CH3:6])[O:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH3:12])[C:13]([Cl:14])([Br:15])[C:16]([F:17])([F:18])[F:19] | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC | COC(C)(OC)OC(C=C(C)C)C(Cl)(Br)C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | da59a6e496e58629453a78c5e1487b31b25688d768592f6d7000493943d39c02 | 9cde3f0ce3308e8c18bafc8301e5ba0177f0ef4f63237b39a252a2d6edcd92fd | null | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[#8:3]-[C;D1;H3:4])-[#8:5]-[C;D1;H3:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]=[C:11](-[C;D1;H3:12])-[C;D1;H3:13]>>[C:7]-[C:8](-[C:10]=[C:11](-[C;D1;H3:12])-[C;D1;H3:13])-[O;H0;D2;+0:9]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[#8:3]-[C;D1;H3:4])-[#8:5]-[C;D1;H3:6] | null | [] | 111 | CELSIUS | null | null | 5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (48.0 g) and isobutyric acid (0.29 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and Dean and Stark received packed with 5A molecular seives. The mixture was heated with agitation t... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol | Ether.Ether.Ether | null | null | null | HO- | null | 111 | null | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>>COC(C)(OC)OC(C=C(C)C)C(Cl)(Br)C(F)(F)F |
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