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-c34472859da14a81bfe0f74e60f15c43 | ord-cb4a46d648dd4f1a83720a3d3f18dc4c | COc1c[n+]([O-])c(C)c(C)c1OC>>COc1cnc(CO)c(C)c1OC | COC1=C(C(=[N+](C=C1OC)[O-])C)C.C(C)(=O)OC(C)=O>>OCC1=NC=C(C(=C1C)OC)OC | [CH3:1][O:2][c:3]1[cH:4][n+:5]([O-:8])[c:6]([CH3:7])[c:9]([CH3:10])[c:11]1[O:12][CH3:13]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([CH2:7][OH:8])[c:9]([CH3:10])[c:11]1[O:12][CH3:13] | COc1c[n+]([O-])c(C)c(C)c1OC | COc1cnc(CO)c(C)c1OC | null | null | null | Miscellaneous | OtherReaction | 7e561d7afee9600ed6bdb2a097e47ef139bafb1884a12ad7f91414ba01df7b33 | 0607ce9ac404b7f992b14bf13602ccd36eb29bd5911f2b79cc25c0bfd203a764 | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O-;H0;D1:5]):[c:6]:[c:7]>>[OH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:6]:[c:7] | 89 | [{"value": 89.0, "product": "OCC1=NC=C(C(=C1C)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | 4.5 of 4,5-dimethoxy-2,3-dimethylpyridine 1-oxide are warmed to 110° C. in 20 ml of acetic anhydride in the course of 30 minutes and the mixture is then concentrated on a rotary evaporator. The oily residue, which consists of the intemediate 2-acetoxymethyl-4,5-dimethoxy-3-methylpyridine, is stirred in 30 ml of 3N sodi... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | null | null | 80 | 2 | COc1c[n+]([O-])c(C)c(C)c1OC>>COc1cnc(CO)c(C)c1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-63bcfa1627524035ab17caa52c67434b | COc1cnc(C)c(C)c1OC>>COc1c[n+]([O-])c(C)c(C)c1OC | COC1=C(C(=NC=C1OC)C)C.ClC=1C=C(C(=O)OO)C=CC1.[OH-].[Na+]>>COC1=C(C(=[N+](C=C1OC)[O-])C)C | [CH3:1][O:2][c:3]1[cH:4][n:5][c:7]([CH3:8])[c:9]([CH3:10])[c:11]1[O:12][CH3:13]>>[CH3:1][O:2][c:3]1[cH:4][n+:5]([O-:6])[c:7]([CH3:8])[c:9]([CH3:10])[c:11]1[O:12][CH3:13] | COc1cnc(C)c(C)c1OC | COc1c[n+]([O-])c(C)c(C)c1OC | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc[nH+]cc1 | [C;D1;H3:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6]>>[C;D1;H3:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O;-;D1;H0:7]):[c:5]:[c:6] | 66.6 | [{"value": 66.0, "product": "COC1=C(C(=[N+](C=C1OC)[O-])C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "COC1=C(C(=[N+](C=C1OC)[O-])C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2 | HOUR | 6.3 g of 4,5-dimethoxy-2,3-dimethylpyridine are dissolved in 120 ml of methylene chloride, 20 g of m-chloroperoxybenzoic acid are added successively and the mixture is stirred first at 20° C. for 2 hours and then at 40° C. for 4 hours. After addition of 20 ml of 5N sodium hydroxide solution, the mixture is washed three... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | null | C(Cl)Cl | 20 | 2 | COc1cnc(C)c(C)c1OC>C(Cl)Cl>COc1c[n+]([O-])c(C)c(C)c1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f635efdd0db543148499f921950620e1 | COc1ccnc(COC(C)=O)c1OC>>COc1ccnc(CO)c1OC | [OH-].[Na+].C(C)(=O)OCC1=NC=CC(=C1OC)OC>>OCC1=NC=CC(=C1OC)OC | CC(=O)[O:9][CH2:8][c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:10]1[O:11][CH3:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][OH:9])[c:10]1[O:11][CH3:12] | COc1ccnc(COC(C)=O)c1OC | COc1ccnc(CO)c1OC | null | null | null | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#7;a:4]>>[#7;a:4]:[c:3]-[C:2]-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "OCC1=NC=CC(=C1OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "OCC1=NC=CC(=C1OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | After adding 15 ml of 2N sodium hydroxide solution, 4.8 g of 2-acetoxymethyl-3,4-dimethoxypyridine are stirred vigorously at 80° C., whereupon a homogeneous solution forms from the initial two-phase mixture. After 2 hours, the solution is allowed to cool and is extracted five times with 30 ml of methylene chloride each... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | null | null | 2 | COc1ccnc(COC(C)=O)c1OC>>COc1ccnc(CO)c1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c54f61d1844b40efaf008bcca8fff9bf | CC(=O)OC(C)=O.COc1cc[n+]([O-])c(C)c1OC>>COc1ccnc(COC(C)=O)c1OC | COC=1C(=[N+](C=CC1OC)[O-])C.C(C)(=O)OC(C)=O>>C(C)(=O)OCC1=NC=CC(=C1OC)OC | CC(=O)[O:9][C:10]([CH3:11])=[O:12].[O-][n+:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH3:15])[c:7]1[CH3:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH2:8][O:9][C:10]([CH3:11])=[O:12])[c:13]1[O:14][CH3:15] | CC(=O)OC(C)=O.COc1cc[n+]([O-])c(C)c1OC | COc1ccnc(COC(C)=O)c1OC | null | null | null | Protection | OtherReaction | f4e85b633bf4e79d1b81c036d2f4e246a93c2eb8ec0202f93c45d73e710e4f0d | dd0b9e5a615173b1d6c9fe991a352f69d24fef80f4bf0eeab7c46667d446dcd0 | c1ccncc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[n+;H0;D3:8](-[O-]):[c:9]:[c:10]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[O;H0;D2;+0:1]-[CH2;D2;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10] | 90 | [{"value": 90.0, "product": "C(C)(=O)OCC1=NC=CC(=C1OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4.8 g (28 mmol) of 3,4-dimethoxy-2-methylpyridine 1-oxide are metered into 25 ml of acetic anhydride at 85° C. in the course of one hour, the mixture is stirred at the same temperature for one hour and concentrated completely in vacuo and the brown oily residue is distilled in a bulb type still under 1 Pa. 5.3 g (90% o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ester | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HO- | null | null | 1 | CC(=O)OC(C)=O.COc1cc[n+]([O-])c(C)c1OC>>COc1ccnc(COC(C)=O)c1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7c86e719293c4a85964d03812b201ded | COc1c([N+](=O)[O-])cc[n+]([O-])c1C.C[O-]>>COc1cc[n+]([O-])c(C)c1OC | COC=1C(=[N+](C=CC1[N+](=O)[O-])[O-])C.C[O-].[Na+].S(O)(O)(=O)=O>>COC=1C(=[N+](C=CC1OC)[O-])C | O=[N+]([O-])[c:3]1[cH:4][cH:5][n+:6]([O-:7])[c:8]([CH3:9])[c:10]1[O:11][CH3:12].[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n+:6]([O-:7])[c:8]([CH3:9])[c:10]1[O:11][CH3:12] | COc1c([N+](=O)[O-])cc[n+]([O-])c1C.C[O-] | COc1cc[n+]([O-])c(C)c1OC | null | null | CO | Functional Group Interconversion | OtherReaction | 27f99d080b738ed3c11247d992420b7c028ad8e0895bb75728d6435304986321 | 5d154e9342b990e3d7c4ce2c6f7cc039bc2f1990cb4cb06dbac9dbddc28572dc | c1cc[nH+]cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a;+:4](-[O;-;D1;H0:5]):[c:6](-[C;D1;H3:7]):[c:8]:1-[#8:9].[C;D1;H3:10]-[O-;H0;D1:11]>>[#8:9]-[c:8]1:[c:6](-[C;D1;H3:7]):[#7;a;+:4](-[O;-;D1;H0:5]):[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:11]-[C;D1;H3:10] | 88 | [{"value": 88.0, "product": "COC=1C(=[N+](C=CC1OC)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 16 | HOUR | 4.5 g (25 mmol) of 3-methoxy-2-methyl-4-nitropyridine 1-oxide are stirred at 40° C. in 75 ml of dry methanol, after addition of 4.7 ml of 30% strength sodium methylate solution, for 16 hours. The mixture is then cooled, brought to pH 7 with concentrated sulphuric acid, filtered and concentrated completely in vacuo, the... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Ether | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | Other | CO | 40 | 16 | COc1c([N+](=O)[O-])cc[n+]([O-])c1C.C[O-]>CO>COc1cc[n+]([O-])c(C)c1OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-561c4e56cfd54777a4013971762f0f41 | COc1ccc[n+]([O-])c1C.O=[N+]([O-])O>>COc1c([N+](=O)[O-])cc[n+]([O-])c1C | [OH-].[Na+].[N+](=O)(O)[O-].COC=1C(=[N+](C=CC1)[O-])C.[N+](=O)(O)[O-]>>COC=1C(=[N+](C=CC1[N+](=O)[O-])[O-])C | [CH3:1][O:2][c:3]1[cH:4][cH:8][cH:9][n+:10]([O-:11])[c:12]1[CH3:13].O[N+:5](=[O:6])[O-:7]>>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][n+:10]([O-:11])[c:12]1[CH3:13] | COc1ccc[n+]([O-])c1C.O=[N+]([O-])O | COc1c([N+](=O)[O-])cc[n+]([O-])c1C | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | ca5f1190ddada94452e11b52ea1eb215875524fe8173f14c45d3608500a1c3bf | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1cc[nH+]cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#8:4]-[c:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[#7;a;+:9](-[O;-;D1;H0:10]):[c:11]:1-[C;D1;H3:12]>>[#8:4]-[c:5]1:[c:11](-[C;D1;H3:12]):[#7;a;+:9](-[O;-;D1;H0:10]):[c:8]:[c:7]:[c;H0;D3;+0:6]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | null | [] | null | null | 8 | HOUR | 8 ml of concentrated nitric acid are added in four portions of 2 ml each to 5.4 g of 3-methoxy-2-methylpyridine 1-oxide in 12 ml of glacial acetic acid at 80° C. in the course of 6 hours, the mixture is stirred at the same temperature overnight, a further 8 ml of nitric acid are added in three portions in the course of... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | C(C)(=O)O | null | 8 | COc1ccc[n+]([O-])c1C.O=[N+]([O-])O>C(C)(=O)O>COc1c([N+](=O)[O-])cc[n+]([O-])c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4408d181f6a54f72929cd29a06522ab8 | COc1cccnc1C.OO>>COc1ccc[n+]([O-])c1C | COC=1C(=NC=CC1)C.OO>>COC=1C(=[N+](C=CC1)[O-])C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:9]1[CH3:10].O[OH:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][n+:7]([O-:8])[c:9]1[CH3:10] | COc1cccnc1C.OO | COc1ccc[n+]([O-])c1C | null | null | C(C)(=O)O | Functional Group Interconversion | OtherReaction | d7f3c84fb751fef5567bc0e84a2e7c0afb271257e8dfb17aa871e038ff1a84c7 | bf536f3bf8ed7b8faf08cf1c004ccd0a5e7fe59339402dd73ac837bb4a52f2ba | c1cc[nH+]cc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | 60 | [{"value": 60.0, "product": "COC=1C(=[N+](C=CC1)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 15.3 g (0.124 mol) of 3-methoxy-2-methylpyridine are dissolved in 100 ml of glacial acetic acid, and 40 ml of 30% strength hydrogen peroxide are added in 4 portions at 80° C. in the course of 6 hours. The mixture is stirred for a further 3 hours and then concentrated in vacuo (1.5 kPa), and two 50 ml portions of acetic... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | C(C)(=O)O | null | 3 | COc1cccnc1C.OO>C(C)(=O)O>COc1ccc[n+]([O-])c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d9e9a77157924c8592aec16db23141ed | COc1ccnc(C(C)O)c1.O=S(Cl)Cl>>COc1ccnc(C(C)Cl)c1.Cl | S(=O)(Cl)Cl.COC1=CC(=NC=C1)C(C)O.C1(=CC=CC=C1)C>>Cl.ClC(C)C1=NC=CC(=C1)OC | O[CH:8]([c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:11]1)[CH3:9].O=S([Cl:10])[Cl:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH:8]([CH3:9])[Cl:10])[cH:11]1.[ClH:12] | COc1ccnc(C(C)O)c1.O=S(Cl)Cl | COc1ccnc(C(C)Cl)c1.Cl | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1ccncc1 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].O=S(-[Cl;H0;D1;+0:7])-[Cl;H0;D1;+0:8]>>[C;D1;H3:2]-[CH;D3;+0:1](-[Cl;H0;D1;+0:7])-[c:3](:[c:4]):[#7;a:5]:[c:6].[ClH;D0;+0:8] | null | [] | null | null | null | null | 36 ml of thionyl chloride are added dropwise to a cooled suspension of 57 g of (±)-1-[4-methoxy-2-pyridyl]ethanol in 400 ml of dichloromethane, in such a way that the internal temperature does not exceed 15° C. The mixture is then heated under reflux for 2.5 h, treated with 300 ml of toluene and concentrated to 150 ml.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccncc1 | Other | ClCCl | null | null | COc1ccnc(C(C)O)c1.O=S(Cl)Cl>ClCCl>COc1ccnc(C(C)Cl)c1.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-30efe7987615405c8b41b1f3ee99935c | COc1ccnc(C(C)OC(C)=O)c1>>COc1ccnc(C(C)O)c1 | C(C)(=O)OC(C)C1=NC=CC(=C1)OC.[OH-].[Na+]>>COC1=CC(=NC=C1)C(C)O | CC(=O)[O:10][CH:8]([c:7]1[n:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:11]1)[CH3:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH:8]([CH3:9])[OH:10])[cH:11]1 | COc1ccnc(C(C)OC(C)=O)c1 | COc1ccnc(C(C)O)c1 | null | null | null | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | c1ccncc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](-[C;D1;H3:3])-[OH;D1;+0:1] | null | [] | 75 | CELSIUS | 2 | HOUR | 114 g of (+)-1-[4-methoxy-2-pyridyl]-ethyl acetate are added dropwise at 70° C. to 220 ml of 4N sodium hydroxide solution. The mixture is then stirred for a further 2 h at 75° C., cooled and extracted with four times 200 ml of dichloromethane. The organic phase is washed with 2N sodium hydroxide solution and water, dri... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1ccncc1 | HO- | null | 75 | 2 | COc1ccnc(C(C)OC(C)=O)c1>>COc1ccnc(C(C)O)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-500050d121a64feabe3a407461393efa | CC(=O)OC(C)=O.CCc1cc(OC)cc[n+]1[O-]>>COc1ccnc(C(C)OC(C)=O)c1 | C(C)C1=[N+](C=CC(=C1)OC)[O-].C(C)(=O)OC(C)=O.C(C)(=O)OC(C)=O>>C(C)(=O)OC(C)C1=NC=CC(=C1)OC | CC(=O)[O:10][C:11]([CH3:12])=[O:13].[O-][n+:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][c:7]1[CH2:8][CH3:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][c:7]([CH:8]([CH3:9])[O:10][C:11]([CH3:12])=[O:13])[cH:14]1 | CC(=O)OC(C)=O.CCc1cc(OC)cc[n+]1[O-] | COc1ccnc(C(C)OC(C)=O)c1 | null | null | null | Protection | OtherReaction | f4e85b633bf4e79d1b81c036d2f4e246a93c2eb8ec0202f93c45d73e710e4f0d | dd0b9e5a615173b1d6c9fe991a352f69d24fef80f4bf0eeab7c46667d446dcd0 | c1ccncc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[C;D1;H3:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[n+;H0;D3:9](-[O-]):[c:10]:[c:11]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[O;H0;D2;+0:1]-[CH;D3;+0:6](-[C;D1;H3:5])-[c:7](:[c:8]):[n;H0;D2;+0:9]:[c:10]:[c:11] | 78 | [{"value": 78.0, "product": "C(C)(=O)OC(C)C1=NC=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 2.5 | HOUR | 171 g of 2-ethyl-4-methoxy-pyridine N-oxide are added dropwise within 3 h to 312 ml of acetic anhydride heated to 90° C., in such a way that the internal temperature does not exceed 115° C. The mixture is then left to stand for a further 2.5 h at 100° C., and excess acetic anhydride is stripped off. Distillation of the... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ester | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HO- | null | 90 | 2.5 | CC(=O)OC(C)=O.CCc1cc(OC)cc[n+]1[O-]>>COc1ccnc(C(C)OC(C)=O)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-aa2d9d186baa4dec80079d17c6497e03 | Nc1cc(F)c(OC(F)F)cc1[N+](=O)[O-]>>Cl.Nc1cc(F)c(OC(F)F)cc1N | FC(OC1=CC(=C(N)C=C1F)[N+](=O)[O-])F.FC(OC1=CC(=C(C=C1F)NC(C)=O)[N+](=O)[O-])F.[N+](=O)(O)[O-].Cl>>Cl.Cl.FC(OC1=CC(=C(C=C1F)N)N)F | O=[N+:15]([O-])[c:14]1[c:4]([NH2:3])[cH:5][c:6]([F:7])[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13]1>>[ClH:2].[NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][c:14]1[NH2:15] | Nc1cc(F)c(OC(F)F)cc1[N+](=O)[O-] | Cl.Nc1cc(F)c(OC(F)F)cc1N | null | null | ClCCl.C1CCCCC1.CO | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 85 | [{"value": 85.0, "product": "Cl.Cl.FC(OC1=CC(=C(C=C1F)N)N)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 22.5 ml of 100% nitric acid are added dropwise at 20° C. within 30 min. to 20 g of the above compound in 200 ml of dichloromethane, and the mixture is stirred for a further 15 h at room temperature. Analogously to Example B7c, this gives N-(4-difluoromethoxy-5-fluoro-2-nitrophenyl)acetamide of m.p. 72°-74° C. (from cyc... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | ClCCl.C1CCCCC1.CO | null | 15 | Nc1cc(F)c(OC(F)F)cc1[N+](=O)[O-]>ClCCl.C1CCCCC1.CO>Cl.Nc1cc(F)c(OC(F)F)cc1N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-afc1b28b948743f0ab162dbe3eb3f56e | Nc1c([N+](=O)[O-])ccc2c1OC(F)(F)O2>>Cl.Nc1ccc2c(c1N)OC(F)(F)O2 | NC1=C(C=CC=2OC(OC21)(F)F)[N+](=O)[O-].Cl>>Cl.Cl.FC1(OC=2C(O1)=CC=C(C2N)N)F | O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]2[c:8]([c:9]1[NH2:10])[O:11][C:12]([F:13])([F:14])[O:15]2>>[ClH:2].[NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([c:9]1[NH2:10])[O:11][C:12]([F:13])([F:14])[O:15]2 | Nc1c([N+](=O)[O-])ccc2c1OC(F)(F)O2 | Cl.Nc1ccc2c(c1N)OC(F)(F)O2 | null | [Pd] | CO | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccc2c(c1)OCO2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97 | [{"value": 97.0, "product": "Cl.Cl.FC1(OC=2C(O1)=CC=C(C2N)N)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 30 g of 4-amino-2,2-difluoro-5-nitro-1,3-benzodioxole are hydrogenated in 300 ml of methanol on 0.5 g of 10% palladium-on-carbon in a circulating hydrogenation apparatus under atmospheric pressure and at room temperature, 2.5 equivalents of methanolic hydrogen chloride solution are added, the mixture is filtered, the s... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)OCO2 | Other | [Pd].CO | null | null | Nc1c([N+](=O)[O-])ccc2c1OC(F)(F)O2>[Pd].CO>Cl.Nc1ccc2c(c1N)OC(F)(F)O2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0b49246c61754d2eb5f40629087f96d0 | COc1cccc(O)c1OC.FC(F)Cl.O=[N+]([O-])O>>COc1cc([N+](=O)[O-])cc(OC(F)F)c1OC | COC1=C(C=CC=C1OC)O.ClC(F)F.[N+](=O)(O)[O-].[OH-].[K+]>>FC(OC1=C(C(=CC(=C1)[N+](=O)[O-])OC)OC)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:9][c:10]([OH:11])[c:15]1[O:16][CH3:17].Cl[CH:12]([F:13])[F:14].O[N+:6](=[O:7])[O-:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]([O:11][CH:12]([F:13])[F:14])[c:15]1[O:16][CH3:17] | COc1cccc(O)c1OC.FC(F)Cl.O=[N+]([O-])O | COc1cc([N+](=O)[O-])cc(OC(F)F)c1OC | null | CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3C(C([C@@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]\4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/C([C@@H](C(=N8)/C(=C4\[N-]5)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.O.[Co+2] | C1CCCCC1.C(C)(=O)OCC.O1CCOCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 2edee3a90d086e0c6aecabbbb84387827a7cfa69a1985004a8e5da1b9462ed39 | 88e41d56e95ada653e6c3e7bd29bcb9c274826b2a35bc97c304754c936ddd589 | c1ccccc1 | Cl-[CH;D3;+0:1](-[F;D1;H0:2])-[F;D1;H0:3].O-[N+;H0;D3:4](-[O;-;D1;H0:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8]1:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:12](-[N+;H0;D3:4](-[O;-;D1;H0:5])=[O;D1;H0:6]):[c:13]:1 | 48 | [{"value": 48.0, "product": "FC(OC1=C(C(=CC(=C1)[N+](=O)[O-])OC)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 50 g of 2,3-dimethoxyphenol are reacted analogously to Example B12a with 80 g of potassium hydroxide and chlorodifluoromethane in dioxane/water. The mixture is extracted with diisopropyl ether by shaking, the extract is washed with sodium hydroxide solution and 35 g of a product (b.p. 70°-74° C./0.3 mbar) are obtained ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Nitrate.Aromatic alcohol | Secondary halide.Secondary halide.Ether.Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3C(C([C@@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]\4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/C([C@@H](C(=N8)/C(=C4\[N-]5)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.O.[Co+2].C1CCCCC1.C(C)(=O)OCC.O1CCOCC1.O | null | null | COc1cccc(O)c1OC.FC(F)Cl.O=[N+]([O-])O>CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3C(C([C@@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]\4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/C([C@@H](C(=N8)/C(=C4\[N-]5)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.O.[Co+2].C1CCCCC1.C(C)(... |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b146a08d4e884b7fbc08bcc79a0d1f24 | CC(=O)C(C)C.ClCc1ccc(Cl)cc1>>CC(=O)C(C)(C)Cc1ccc(Cl)cc1 | [OH-].[K+].ClC1=CC=C(CCl)C=C1.C(C)(C)C(=O)C>>ClC1=CC=C(C=C1)CC(C(C)=O)(C)C | [CH3:1][C:2](=[O:3])[CH:4]([CH3:5])[CH3:6].Cl[CH2:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[C:4]([CH3:5])([CH3:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | CC(=O)C(C)C.ClCc1ccc(Cl)cc1 | CC(=O)C(C)(C)Cc1ccc(Cl)cc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | e8b75e5efb691ecf3c9116420e15918cdd0fda7b899536fb179ed39cbdad1bc2 | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "ClC1=CC=C(C=C1)CC(C(C)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "ClC1=CC=C(C=C1)CC(C(C)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 3 | HOUR | 254.4 g (4 mols) of powdered technical grade potassium hydroxide (88% strength) are suspended in 1 liter of toluene, 40 g of tetrabutylammonium bromide are added, and a mixture of 644 g (4 mols) of 4-chlorobenzyl chloride and 430 g (5 mols) of methyl isopropyl ketone is then slowly added dropwise at 85° C. To complete ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | null | null | c1ccccc1 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | 85 | 3 | CC(=O)C(C)C.ClCc1ccc(Cl)cc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>CC(=O)C(C)(C)Cc1ccc(Cl)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-51cb3e7d23ad4c4bb41ea2033ba73586 | C=CCCl.CC(=O)C(C)C>>C=CCC(C)(C)C(C)=O | C1(=CC=CC=C1)C.[OH-].[K+].C(C=C)Cl.C(C)(C)C(=O)C>>CC(CC=C)(C(C)=O)C | Cl[CH2:3][CH:2]=[CH2:1].[CH:4]([CH3:5])([CH3:6])[C:7]([CH3:8])=[O:9]>>[CH2:1]=[CH:2][CH2:3][C:4]([CH3:5])([CH3:6])[C:7]([CH3:8])=[O:9] | C=CCCl.CC(=O)C(C)C | C=CCC(C)(C)C(C)=O | null | [Cl-].C(CCCCCCC)[NH+](CCCCCCCC)CCCCCCCC | null | C-C Coupling | OtherReaction | cd9c61577f3b1e4398b200b69dbc22378f11d930d200a7cd1fe8916ac61b33c7 | f5ccd90096c3201115eb6510107831f398bf8f80381c3ea6084a10b0ebb25a81 | null | Cl-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H3:4]-[CH;D3;+0:5](-[C;D1;H3:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:5](-[C;D1;H3:4])(-[C;D1;H3:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 76 | [{"value": 76.0, "product": "CC(CC=C)(C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 4 | HOUR | 63.6 g (1 mol) of powdered technical grade potassium hydroxide (88% strength) are suspended in 200 ml of toluene, and 10 g of trioctylammonium chloride are added. A mixture of 76.5 g (1 mol) of allyl chloride and 129 g (1.5 mols) of methyl isopropyl ketone is then added dropwise so that the temperature does not exceed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Allyl | null | null | null | HCl | [Cl-].C(CCCCCCC)[NH+](CCCCCCCC)CCCCCCCC | 70 | 4 | C=CCCl.CC(=O)C(C)C>[Cl-].C(CCCCCCC)[NH+](CCCCCCCC)CCCCCCCC>C=CCC(C)(C)C(C)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9a4daa9ae65a4e5fadbc80d78186f469 | C#CCBr.CC(=O)C(C)C>>C#CCC(C)(C)C(C)=O | C(C#C)Br.C(C)(C)C(=O)C.[OH-].[K+].C1(=CC=CC=C1)C>>CC(CC#C)(C(C)=O)C | Br[CH2:3][C:2]#[CH:1].[CH:4]([CH3:5])([CH3:6])[C:7]([CH3:8])=[O:9]>>[CH:1]#[C:2][CH2:3][C:4]([CH3:5])([CH3:6])[C:7]([CH3:8])=[O:9] | C#CCBr.CC(=O)C(C)C | C#CCC(C)(C)C(C)=O | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | C-C Coupling | OtherReaction | e8b75e5efb691ecf3c9116420e15918cdd0fda7b899536fb179ed39cbdad1bc2 | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | null | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C;D1;H3:4]-[CH;D3;+0:5](-[C;D1;H3:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]>>[C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:5](-[C;D1;H3:4])(-[C;D1;H3:6])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9] | 54 | [{"value": 54.0, "product": "CC(CC#C)(C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 12 | HOUR | 70 g (1.1 mols) of powdered technical grade potassium hydroxide (88% strength) and 10 g of tetrabutylammonium bromide in 250 ml of toluene are initially introduced. A mixture if 119 g (1 mol) of propargyl bromide and 103.2 g (1.2 mols) of methyl isopropyl ketone is then added dropwise so that the temperature does not e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | null | null | null | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | 45 | 12 | C#CCBr.CC(=O)C(C)C>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>C#CCC(C)(C)C(C)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0e9e073cc57d485fad6ab38501ccba80 | CC(=O)C(C)C.ClCc1ccccc1>>CC(=O)C(C)(C)Cc1ccccc1 | O.C(C)(C)C(=O)C.C(C1=CC=CC=C1)Cl.[OH-].[K+]>>CC(C(C)=O)(CC1=CC=CC=C1)C | [CH3:1][C:2](=[O:3])[CH:4]([CH3:5])[CH3:6].Cl[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[C:4]([CH3:5])([CH3:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CC(=O)C(C)C.ClCc1ccccc1 | CC(=O)C(C)(C)Cc1ccccc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | e8b75e5efb691ecf3c9116420e15918cdd0fda7b899536fb179ed39cbdad1bc2 | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 47.9 | [{"value": 47.9, "product": "CC(C(C)=O)(CC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 12 | HOUR | 516 g (6 mols) of methyl isopropyl ketone, 759 g (6 mols) of benzyl chloride and 60 g (0.186 mol) of tetrabutylammonium bromide are dissolved in 1 liter of toluene, and the solution is heated to 100° C. 420 g (7.49 mols) of powered potassium hydroxide are slowly metered in at this temperature. The reaction mixture is s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | null | null | c1ccccc1 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | 100 | 12 | CC(=O)C(C)C.ClCc1ccccc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>CC(=O)C(C)(C)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2f4f64a7a9604d9cb15c5894dbbdf971 | BrBr.CC(=O)C(C)(C)Cc1ccccc1>>CC(C)(Cc1ccccc1)C(=O)CBr | CC(C(C)=O)(CC1=CC=CC=C1)C.BrBr>>BrCC(C(CC1=CC=CC=C1)(C)C)=O | Br[Br:14].[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11](=[O:12])[CH3:13]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11](=[O:12])[CH2:13][Br:14] | BrBr.CC(=O)C(C)(C)Cc1ccccc1 | CC(C)(Cc1ccccc1)C(=O)CBr | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:4]-[C:3](-[C:2])=[O;D1;H0:5] | 100 | [{"value": 100.0, "product": "BrCC(C(CC1=CC=CC=C1)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 100 g (0.57 mol) of 3,3-dimethyl-4-phenylbutan-2-one (Example 5) are dissolved in 0.8 liter of chloroform, and 29 ml (91.9 g; 1.14 mols) of bromine are added slowly at room temperature. The mixture is stirred for a further hour at room temperature and is concentrated. 145.5 g (quantitative) of 1-bromo-3,3-dimethyl-4-ph... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(Cl)(Cl)Cl | null | null | BrBr.CC(=O)C(C)(C)Cc1ccccc1>C(Cl)(Cl)Cl>CC(C)(Cc1ccccc1)C(=O)CBr |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a4036584ea9043a3bc1ad0d617585e2e | CC(C)(Cc1ccccc1)C(=O)CBr.c1nc[nH]n1>>CC(C)(Cc1ccccc1)C(=O)Cn1cncn1 | BrCC(C(CC1=CC=CC=C1)(C)C)=O.N1N=CN=C1.C([O-])([O-])=O.[K+].[K+]>>CC(C(CN1N=CN=C1)=O)(CC1=CC=CC=C1)C | Br[CH2:13][C:11]([C:2]([CH3:1])([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)=[O:12].[nH:14]1[cH:15][n:16][cH:17][n:18]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11](=[O:12])[CH2:13][n:14]1[cH:15][n:16][cH:17][n:18]1 | CC(C)(Cc1ccccc1)C(=O)CBr.c1nc[nH]n1 | CC(C)(Cc1ccccc1)C(=O)Cn1cncn1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5fd537c1811b5d927630316f1d8d0b895550dd6e0a23faad4b2f0cac2b65c9fb | 0844e813fd6aa8a6f803ffd9d05cd5ff5272ddf69396b8c87d384d86e0562add | O=C(CCc1ccccc1)Cn1cncn1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[#7;a:5]1:[c:6]:[nH;D2;+0:7]:[#7;a:8]:[c:9]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[#7;a:5]:[c:6]:1 | 48.4 | [{"value": 48.4, "product": "CC(C(CN1N=CN=C1)=O)(CC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.3, "product": "CC(C(CN1N=CN=C1)=O)(CC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 74 g (0.29 mol) of 1-bromo-3,3-dimethyl-4-phenylbutan-2-one, 40 g (0.58 mol) of 1,2,4-triazole and 80 g of potassium carbonate are dissolved in 700 ml of acetone, and the solution is heated under reflux for 3 hours. Thereafter, it is allowed to cool and is filtered off under suction from the inorganic residue, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | c1nc[nH]n1 | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | HBr | CC(=O)C | null | null | CC(C)(Cc1ccccc1)C(=O)CBr.c1nc[nH]n1>CC(=O)C>CC(C)(Cc1ccccc1)C(=O)Cn1cncn1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6ff56abd36cd489b8cb4b6495cf0458f | CC(C)(Cc1ccccc1)C(=O)Cn1cncn1.ClCc1ccccc1>>CC(C)(Cc1ccccc1)C(=O)C(Cc1ccccc1)n1cncn1 | CC(C(CN1N=CN=C1)=O)(CC1=CC=CC=C1)C.C(C1=CC=CC=C1)Cl.[OH-].[K+]>>C1(=CC=CC=C1)CC(C(C(CC1=CC=CC=C1)N1N=CN=C1)=O)(C)C | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11](=[O:12])[CH2:13][n:21]1[cH:22][n:23][cH:24][n:25]1.Cl[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11](=[O:12])[CH:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:2... | CC(C)(Cc1ccccc1)C(=O)Cn1cncn1.ClCc1ccccc1 | CC(C)(Cc1ccccc1)C(=O)C(Cc1ccccc1)n1cncn1 | null | null | O.CS(=O)C | C-C Coupling | OtherReaction | e8b75e5efb691ecf3c9116420e15918cdd0fda7b899536fb179ed39cbdad1bc2 | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | O=C(CCc1ccccc1)C(Cc1ccccc1)n1cncn1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[#7;a:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1>>[C:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#7;a:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1 | 81.8 | [{"value": 81.8, "product": "C1(=CC=CC=C1)CC(C(C(CC1=CC=CC=C1)N1N=CN=C1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "C1(=CC=CC=C1)CC(C(C(CC1=CC=CC=C1)N1N=CN=C1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | 48.6 g (0.2 mol) of 3,3-dimethyl-4-phenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 27.9 g (0.22 mol) of benzyl chloride and 12.3 g (0.22 mol) of potassium hydroxide in 15 ml of water are dissolved in 300 ml of dimethylsulphoxide. The reaction mixture is stirred for a further 8 hours at 50° C. and then poured onto water. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1nc[nH]n1 | HCl | O.CS(=O)C | 50 | 8 | CC(C)(Cc1ccccc1)C(=O)Cn1cncn1.ClCc1ccccc1>O.CS(=O)C>CC(C)(Cc1ccccc1)C(=O)C(Cc1ccccc1)n1cncn1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a9bc5be1b5fe444bb0b94e7222020b44 | COC(=O)CC(O)CCl.NCC(N)=O>>NC(=O)CN1CC(O)CC1=O | Cl.NCC(=O)N.C([O-])([O-])=O.[Na+].[Na+].ClCC(CC(=O)OC)O>>C1C(CN(C1=O)CC(=O)N)O | CO[C:10]([CH2:9][CH:7]([CH2:6]Cl)[OH:8])=[O:11].[NH2:1][C:2](=[O:3])[CH2:4][NH2:5]>>[NH2:1][C:2](=[O:3])[CH2:4][N:5]1[CH2:6][CH:7]([OH:8])[CH2:9][C:10]1=[O:11] | COC(=O)CC(O)CCl.NCC(N)=O | NC(=O)CN1CC(O)CC1=O | null | null | C(C)O | Acylation | OtherReaction | 819e3f2b7868adc1c1b9de9bb195abc43156b28c3cf194597f96cec7ac859f91 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C1CCCN1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[O;D1;H1:5])-[CH2;D2;+0:6]-Cl.[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[C:10]-[NH2;D1;+0:11]>>[N;D1;H2:7]-[C:8](=[O;D1;H0:9])-[C:10]-[N;H0;D3;+0:11]1-[CH2;D2;+0:6]-[C:4](-[O;D1;H1:5])-[C:3]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 75 | [{"value": 75.0, "product": "C1C(CN(C1=O)CC(=O)N)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In 10 ml of ethanol, 1.11 g (10 m.moles) of glycinamide hydrochloride, 1.06 g (10 m.moles) of sodium carbonate, and 1.53 g (10 m.moles) of methyl 4-chloro-3-hydroxybutyrate were stirred and refluxed simultaneously for 20 hours. After completion of the reaction, the warm reaction mixture was filtered to expel inorganic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1 | HCl | C(C)O | null | null | COC(=O)CC(O)CCl.NCC(N)=O>C(C)O>NC(=O)CN1CC(O)CC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4f322b0df7884eecbb913acbcc3a95a3 | CCOC(=O)c1cc(NC(C)=O)c([N+](=O)[O-])cc1OCC>>CCOc1cc([N+](=O)[O-])c(N)cc1C(=O)OC | C(C)(=O)NC=1C(=CC(=C(C(=O)OCC)C1)OCC)[N+](=O)[O-].S(O)(O)(=O)=O>>NC=1C(=CC(=C(C(=O)OC)C1)OCC)[N+](=O)[O-] | CC(=O)[NH:11][c:10]1[c:6]([N+:7](=[O:8])[O-:9])[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:13]([C:14](=[O:15])[O:16][CH2:17]C)[cH:12]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([NH2:11])[cH:12][c:13]1[C:14](=[O:15])[O:16][CH3:17] | CCOC(=O)c1cc(NC(C)=O)c([N+](=O)[O-])cc1OCC | CCOc1cc([N+](=O)[O-])c(N)cc1C(=O)OC | null | null | null | Reduction | OtherReaction | 4a88b9d891ba339b9f646daf4454983fe862101e27f3f81079d77433b43c2a4d | 0f81e8b234be8a24e6ae74926d0948198849f4c90af528e8f6929d1a30a9bbd7 | c1ccccc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-C(-C)=O):[c:9]>>[CH3;D1;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9] | null | [] | null | null | null | null | A suspension of 1 5 g of ethyl 5-acetylamino-2-ethoxy-4-nitrobenzoate in 50 ml of 5 % (v/v) sulfuric acid methanolic solution was refluxed for 4 hours After cooling, the reaction solution was poured into an ice water, the resulting crystals were collected by filtration and recrystallized from methanol to give the title... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Ester.Primary amine | null | null | c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cc(NC(C)=O)c([N+](=O)[O-])cc1OCC>>CCOc1cc([N+](=O)[O-])c(N)cc1C(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-080db1e1911245f1a72773b25eb51c23 | CCOc1cc([N+](=O)[O-])c(N)cc1C(=O)OC>>CCOc1cc(N)c(N)cc1C(=O)OC | NC=1C(=CC(=C(C(=O)OC)C1)OCC)[N+](=O)[O-]>>NC1=CC(=C(C(=O)OC)C=C1N)OCC | O=[N+:7]([O-])[c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:11]([C:12](=[O:13])[O:14][CH3:15])[cH:10][c:8]1[NH2:9]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([NH2:9])[cH:10][c:11]1[C:12](=[O:13])[O:14][CH3:15] | CCOc1cc([N+](=O)[O-])c(N)cc1C(=O)OC | CCOc1cc(N)c(N)cc1C(=O)OC | null | [C].[Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A suspension of 873 mg of methyl 5-amino-2-ethoxy-4-nitrobenzoate and 50 mg of 10 % palladium carbon in 50 ml of ethanol was stirred at room temperature under a hydrogen atmosphere. After the absorption of hydrogen was completed, the catalyst was removed by filtration, and the filtrate was evaporated to dryness under r... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [C].[Pd].C(C)O | null | null | CCOc1cc([N+](=O)[O-])c(N)cc1C(=O)OC>[C].[Pd].C(C)O>CCOc1cc(N)c(N)cc1C(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-891c1c61ec8840a4be4dcb49b477b3d6 | CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O.CCOc1cc(N)c(N)cc1C(=O)OC>>CCOC(=O)c1c(O)c2ccccc2c2nc3cc(OCC)c(C(=O)OC)cc3nc12 | C(C)O.NC1=CC(=C(C(=O)OC)C=C1N)OCC.OC1=C(C(C2=CC=CC=C2C1=O)=O)C(=O)OCC>>C(C)OC=1C(=CC2=NC3=C(C(=C4C(=C3N=C2C1)C=CC=C4)O)C(=O)OCC)C(=O)OC | O=[C:15]1[c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[C:7](=[O:8])[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[C:31]1O.[NH2:16][c:17]1[cH:18][c:19]([O:20][CH2:21][CH3:22])[c:23]([C:24](=[O:25])[O:26][CH3:27])[cH:28][c:29]1[NH2:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([OH:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[... | CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O.CCOc1cc(N)c(N)cc1C(=O)OC | CCOC(=O)c1c(O)c2ccccc2c2nc3cc(OCC)c(C(=O)OC)cc3nc12 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 0f37fd42aea68cadbedb11d01c9c5ebfd4f7677147d66d48c8da29ffeb8db436 | db2db5c11675d0fa08e932d30f06638472b18a8a17601e3ea92d2edabfa89b7b | c1ccc2c(c1)ccc1nc3ccccc3nc12 | O-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11](:[c:12])-[C;H0;D3;+0:13]-1=O.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17](-[NH2;D1;+0:18]):[c:19]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[c;H0;D3;+0:1]2:[n;H0;D2;+0:18]:[c:17](:[c:19]):[c:15](:[... | null | [] | null | null | 2 | HOUR | To a solution of 895 mg of ethyl 3-hydroxy-1,4-dihydro1,4-dioxo-2-naphthoate in 10 ml of N,N-dimethylformamide was added 620 mg of N,N'-carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours. To the mixture was added the crude methyl 4,5-diamino-2-ethoxybenzoate in 10 ml of N,N-dimethyl-formam... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Enol.Primary amine.Primary amine | Ester.Aromatic alcohol | C1=CCc2ccccc2C1.c1ccccc1 | c1ccc2c(c1)ccc1nc3ccccc3nc12 | c1ccc2c(c1)ccc1nc3ccccc3nc12 | HO- | CN(C=O)C | null | 2 | CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O.CCOc1cc(N)c(N)cc1C(=O)OC>CN(C=O)C>CCOC(=O)c1c(O)c2ccccc2c2nc3cc(OCC)c(C(=O)OC)cc3nc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a170a4be891f44c2bc90932bb1a45f78 | COC(=O)c1cc(N)c([N+](=O)[O-])cc1OC>>COc1cc([N+](=O)[O-])c(N)cc1C(=O)O | NC=1C(=CC(=C(C(=O)OC)C1)OC)[N+](=O)[O-].[OH-].[K+].Cl>>NC=1C(=CC(=C(C(=O)O)C1)OC)[N+](=O)[O-] | C[O:15][C:13]([c:12]1[c:3]([O:2][CH3:1])[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11]1)=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11][c:12]1[C:13](=[O:14])[OH:15] | COC(=O)c1cc(N)c([N+](=O)[O-])cc1OC | COc1cc([N+](=O)[O-])c(N)cc1C(=O)O | null | null | O1CCOCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | To a suspension of 13.57 g of methyl 5-amino-2-methoxy-4-nitrobenzoate in 250 ml of dioxane was added a solution of 4.36 g of potassium hydroxide in 25 ml of water, and the mixture was refluxed for 4 hours. To the reaction solution was added 7 ml of concentrated hydrochloric acid. The solvent was evaporated under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O1CCOCC1.O | null | null | COC(=O)c1cc(N)c([N+](=O)[O-])cc1OC>O1CCOCC1.O>COc1cc([N+](=O)[O-])c(N)cc1C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bcfdfddfae3a43ad965c1d4f29ef6011 | C1CCNC1.COc1cc([N+](=O)[O-])c(N)cc1C(=O)O>>COc1cc([N+](=O)[O-])c(N)cc1C(=O)N1CCCC1 | N1CCCC1.NC=1C(=CC(=C(C(=O)O)C1)OC)[N+](=O)[O-]>>NC=1C(=CC(=C(C(=O)N2CCCC2)C1)OC)[N+](=O)[O-] | [NH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1.O[C:13]([c:12]1[c:3]([O:2][CH3:1])[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11]1)=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11][c:12]1[C:13](=[O:14])[N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1 | C1CCNC1.COc1cc([N+](=O)[O-])c(N)cc1C(=O)O | COc1cc([N+](=O)[O-])c(N)cc1C(=O)N1CCCC1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | To a solution of 4.24 g of 5-amino-2-methoxy-4-nitrobenzoic acid in 30 ml of N,N-dimethylformamide was added 3.24 g of N,N'-carbonyldiimidazole at room temperature. After 30 minutes, 5 ml of pyrrolidine was added, and the mixture was stirred for 2 hours. The solvent was evaporated under reduced pressure, and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | CN(C=O)C | null | 0.5 | C1CCNC1.COc1cc([N+](=O)[O-])c(N)cc1C(=O)O>CN(C=O)C>COc1cc([N+](=O)[O-])c(N)cc1C(=O)N1CCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f895edc41e134a04912976c873e74c91 | COC(=O)c1cc(N)c([N+](=O)[O-])cc1OC.N>>COc1cc([N+](=O)[O-])c(N)cc1C(N)=O | NC=1C(=CC(=C(C(=O)OC)C1)OC)[N+](=O)[O-].O.N>>NC=1C(=CC(=C(C(=O)N)C1)OC)[N+](=O)[O-] | CO[C:13]([c:12]1[c:3]([O:2][CH3:1])[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11]1)=[O:15].[NH3:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11][c:12]1[C:13]([NH2:14])=[O:15] | COC(=O)c1cc(N)c([N+](=O)[O-])cc1OC.N | COc1cc([N+](=O)[O-])c(N)cc1C(N)=O | null | null | O1CCOCC1 | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 40 | HOUR | To a solution of 5.66 g of methyl 5-amino-2-methoxy-4-nitrobenzoate in 200 ml of dioxane was added 50 ml of 28 % ammonia water, and then the mixture was allowed to stand at room temperature for 40 hours. The solvent was evaporated under reduced pressure, and the residue was recrystallized from dioxane to give the title... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccccc1 | HO- | O1CCOCC1 | null | 40 | COC(=O)c1cc(N)c([N+](=O)[O-])cc1OC.N>O1CCOCC1>COc1cc([N+](=O)[O-])c(N)cc1C(N)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b3e0e8b3d9e24c10a6b7e68172cefca4 | COc1cc([N+](=O)[O-])c(N)cc1C(=O)O>>COc1cc([N+](=O)[O-])c(N)cc1C(=O)Oc1ccccc1 | NC=1C(=CC(=C(C(=O)O)C1)OC)[N+](=O)[O-].S(=O)(Cl)Cl>>NC=1C(=CC(=C(C(=O)OC2=CC=CC=C2)C1)OC)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11][c:12]1[C:13](=[O:14])[OH:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH2:10])[cH:11][c:12]1[C:13](=[O:14])[O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc([N+](=O)[O-])c(N)cc1C(=O)O | COc1cc([N+](=O)[O-])c(N)cc1C(=O)Oc1ccccc1 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 2640b6d528093b776d79d942911e114b3490be6981cb7ca8e05a8b09997b8c38 | 2544f5a75f58466594e8a458c4167bc85e6ab94e6608e9185a9356c6df8260b8 | O=C(Oc1ccccc1)c1ccccc1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:4]>>[O;D1;H0:1]=[C:2](-[c:4])-[O;H0;D2;+0:3]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 30 | MINUTE | To a suspension of 5.55 g of 5-amino-2-methoxy-4-nitrobenzoic acid in 40 ml of benzene was added 40 ml of thionyl chloride, and the mixture was refluxed for 4 hours. Subsequently, an excess amount of the thionyl chloride and the solvent were evaporated, the residue was dissolved in 40 ml of benzene, and then 12.3 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C1=CC=CC=C1 | null | 0.5 | COc1cc([N+](=O)[O-])c(N)cc1C(=O)O>C1=CC=CC=C1>COc1cc([N+](=O)[O-])c(N)cc1C(=O)Oc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-491a4f8f742343318b3697e3cf01bfb4 | COc1cc([N+](=O)[O-])c(N)cc1C(N)=O>>COc1cc(N)c(N)cc1C(N)=O | NC=1C(=CC(=C(C(=O)N)C1)OC)[N+](=O)[O-]>>NC1=CC(=C(C(=O)N)C=C1N)OC | O=[N+:6]([O-])[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([C:11]([NH2:12])=[O:13])[cH:9][c:7]1[NH2:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([NH2:8])[cH:9][c:10]1[C:11]([NH2:12])=[O:13] | COc1cc([N+](=O)[O-])c(N)cc1C(N)=O | COc1cc(N)c(N)cc1C(N)=O | null | [C].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 60 | CELSIUS | null | null | A suspension of 3.04 g of 5-amino-2-methoxy-4-nitrobenzamide and 110 mg of 10 % palladium carbon in 300 ml of methanol was stirred at 60° C. under a hydrogen atmosphere. After absorption of hydrogen was completed, the catalyst was removed by filtration, and the filtrate was concentrated to give the title compound, m.p.... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [C].[Pd].CO | 60 | null | COc1cc([N+](=O)[O-])c(N)cc1C(N)=O>[C].[Pd].CO>COc1cc(N)c(N)cc1C(N)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-645d23f56c494813b02511252ba424b5 | CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O.CCOC(=O)Cl>>CCOC(=O)OC1=C(C(=O)OCC)C(=O)c2ccccc2C1=O | OC1=C(C(C2=CC=CC=C2C1=O)=O)C(=O)OCC.C(C)N(CC)CC.ClC(=O)OCC>>C(C)OC(=O)OC1=C(C(C2=CC=CC=C2C1=O)=O)C(=O)OCC | [OH:6][C:7]1=[C:8]([C:9](=[O:10])[O:11][CH2:12][CH3:13])[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:23].Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6][C:7]1=[C:8]([C:9](=[O:10])[O:11][CH2:12][CH3:13])[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:2... | CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O.CCOC(=O)Cl | CCOC(=O)OC1=C(C(=O)OCC)C(=O)c2ccccc2C1=O | null | null | O1CCCC1 | Acylation | Schotten-Baumann to ester | 5c9831da69657409ba7bd0a3096162b750678f7e141d35459e83185367325ab9 | 0e42a6e697573ca10503dcf2b634671b9afcb1038f77ae84d0feab55946900a5 | O=C1C=CC(=O)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8](=[C:9](-[OH;D1;+0:10])-[C:11](=[O;D1;H0:12])-[c:13])-[C:14]=[O;D1;H0:15]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8](=[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:11](=[O;D1;H0:12])-[c:13])-[C:14]=[O;D1;H0:15] | null | [] | null | null | 2 | HOUR | To a solution of 2.48 g of ethyl 3-hydroxy-1,4-dihydro1,4-dioxo-2-naphthoate and 1.5 ml of triethylamine in 10 ml of dry tetrahydrofuran was added dropwise 1 ml of ethyl chloroformate at 5° C. or below, and the mixture was stirred at room temperature for 2 hours. The resulting solid was removed by filtration, and the f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Enol | Carbonic Ester | null | null | C1=CCc2ccccc2C1 | HCl | O1CCCC1 | null | 2 | CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O.CCOC(=O)Cl>O1CCCC1>CCOC(=O)OC1=C(C(=O)OCC)C(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-25d717c20516453d9c35a1cb80195294 | COc1cc([N+](=O)[O-])c(N)cc1C(=O)N(C)C>>COc1cc(N)c(N)cc1C(=O)N(C)C | CN(C(C1=C(C=C(C(=C1)N)[N+](=O)[O-])OC)=O)C>>CN(C(C1=C(C=C(C(=C1)N)N)OC)=O)C | O=[N+:6]([O-])[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([C:11](=[O:12])[N:13]([CH3:14])[CH3:15])[cH:9][c:7]1[NH2:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([NH2:8])[cH:9][c:10]1[C:11](=[O:12])[N:13]([CH3:14])[CH3:15] | COc1cc([N+](=O)[O-])c(N)cc1C(=O)N(C)C | COc1cc(N)c(N)cc1C(=O)N(C)C | null | [C].[Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A suspension of 3.62 g of N,N-dimethyl 5-amino-2-methoxy4-nitrobenzamide and 150 mg of 10 % palladium carbon in 140 ml of ethanol was stirred at 70°-80° C. under a hydrogen atmosphere. After the absorption of hydrogen was completed, the catalyst was removed by filtration, and the filtrate was evaporated to dryness to g... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [C].[Pd].C(C)O | null | null | COc1cc([N+](=O)[O-])c(N)cc1C(=O)N(C)C>[C].[Pd].C(C)O>COc1cc(N)c(N)cc1C(=O)N(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-669afe21a6c94457b614431828ff5378 | CCOC(=O)OC1=C(C(=O)OCC)C(=O)c2ccccc2C1=O>>CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O | C(C)OC(=O)OC1=C(C(C2=CC=CC=C2C1=O)=O)C(=O)OCC>>OC1=C(C(C2=CC=CC=C2C1=O)=O)C(=O)OCC | CCOC(=O)[O:8][C:7]1=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:17](=[O:18])[c:16]2[c:11]([cH:12][cH:13][cH:14][cH:15]2)[C:9]1=[O:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([OH:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]1=[O:18] | CCOC(=O)OC1=C(C(=O)OCC)C(=O)c2ccccc2C1=O | CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O | null | null | O1CCCC1 | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 1f127acc721d58b85f26233246e4bb998945459af6b424dde9f17c27128b810d | fde344b61345cfd3921c83775cd6c5b93b7c81dba5b2fd728b3eb5fd56fc77ae | O=C1C=CC(=O)c2ccccc21 | C-C-O-C(=O)-[O;H0;D2;+0:1]-[C:2](=[C:3](-[C:4](-[#8:5])=[O;D1;H0:6])-[C:7]=[O;D1;H0:8])-[C:9](=[O;D1;H0:10])-[c:11]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3](=[C:2](-[OH;D1;+0:1])-[C:9](=[O;D1;H0:10])-[c:11])-[C:7]=[O;D1;H0:8] | null | [] | null | null | null | null | To the tetrahydrofuran solution under water cooling was added a solution of ethyl 3-ethoxycarbonyloxy-1,4-dihydro-1,4-dioxo-2-naphthoate, obtained by the procedure of Referential Example 22(1) using 3.41 g of ethyl 3-hydroxy-1,4-dihydro-1,4-dioxo-2-naphthoate, in 10 ml of tetrahydrofuran. The mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester | Enol | null | null | C1=CCc2ccccc2C1 | HO- | O1CCCC1 | null | null | CCOC(=O)OC1=C(C(=O)OCC)C(=O)c2ccccc2C1=O>O1CCCC1>CCOC(=O)C1=C(O)C(=O)c2ccccc2C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5cc48f0a138a4dc4bcee162880e6a771 | C=CC#N.C=CC(CCCCCCCCC)=NO>>C=C(C#N)CCCCCCCCC | C(C=C)#N.CC=1C=CC=CC1C.C(CCCCCCCC)C(C=C)=NO>>C(CCCCCCCC)C(C#N)=C | [CH2:1]=[CH:2][C:3]#[N:4].C=CC(=NO)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>>[CH2:1]=[C:2]([C:3]#[N:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13] | C=CC#N.C=CC(CCCCCCCCC)=NO | C=C(C#N)CCCCCCCCC | null | C(C)C(C(=O)[O-])CCCC.[Cu+2].C(C)C(C(=O)[O-])CCCC | null | C-C Coupling | OtherReaction | fd79b1593b2906913d9dceb9488c568dd9acd9840935e9931bf8c9c472997196 | a259f45a344da3183e96d62de08419dd5868237740e0b89dd258fcbc666488fd | null | C=C-C(=N-O)-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H2:4]=[CH;D2;+0:5]-[C:6]#[N;D1;H0:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:5](=[C;D1;H2:4])-[C:6]#[N;D1;H0:7] | 89 | [{"value": 89.0, "product": "C(CCCCCCCC)C(C#N)=C", "details": "PERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | 10 | MINUTE | A solution of 80.7 g of acrylonitrile and 5.3 g of copper(II) 2-ethylhexanoate in 250 g or o-xylene was heated to the boil (97° C.), after which 151.5 g of 99% pure alpha-nonylacrolein oxime were added dropwise in the course of 15 minutes, the temperature increasing to 115° C. during the addition. When the addition was... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Vinyl.Oxime | Vinyl | null | null | null | HO- | C(C)C(C(=O)[O-])CCCC.[Cu+2].C(C)C(C(=O)[O-])CCCC | 115 | 0.166667 | C=CC#N.C=CC(CCCCCCCCC)=NO>C(C)C(C(=O)[O-])CCCC.[Cu+2].C(C)C(C(=O)[O-])CCCC>C=C(C#N)CCCCCCCCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c71aa7c41c254ef8940038a9e76a0288 | CN(C)c1ccc(C=NO)cc1>>CN(C)c1ccc(C#N)cc1 | C(C=C)#N.CN(C1=CC=C(C=NO)C=C1)C>>CN(C1=CC=C(C#N)C=C1)C | O[N:9]=[CH:8][c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:11][cH:10]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1 | CN(C)c1ccc(C=NO)cc1 | CN(C)c1ccc(C#N)cc1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | CC=1C=CC=CC1C | Functional Group Interconversion | OtherReaction | 17f476cc256704e312f02cdb730538a4d2e78e129aaed9ef4aa555a9b052c890 | 9ad4e779dba60265752423413bc1b61ff9562539f91b24f3b3d9205e4bb46232 | c1ccccc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 90.4 | [{"value": 90.0, "product": "CN(C1=CC=C(C#N)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "CN(C1=CC=C(C#N)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | 8 | HOUR | A solution of 53 g of acrylonitrile and 1.0 g of copper(II) acetate in 100 g of o-xylene was heated to the boil (85° C.), after which a solution of 82 g of p-dimethylaminobenzaldoxime in 110 g of o-xylene was added dropwise by heating further. During the addition, the boiling point of the reaction mixture increased to ... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Nitrile | null | null | c1ccccc1 | HO- | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CC=1C=CC=CC1C | 135 | 8 | CN(C)c1ccc(C=NO)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CC=1C=CC=CC1C>CN(C)c1ccc(C#N)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-32ae5c7ca03e4dc381e964a85ea45d07 | CCCCCCOc1ccc(CCC(=O)Cl)cc1.Oc1ccc(-c2ccc(F)cc2)cc1>>CCCCCCOc1ccc(CC(C)C(=O)Oc2ccc(-c3ccc(F)cc3)cc2)cc1 | OC1=CC=C(C=C1)C1=CC=C(C=C1)F.N1=CC=CC=C1.C(CCCCC)OC1=CC=C(C=C1)CCC(=O)Cl>>CC(C(=O)OC1=CC=C(C=C1)C1=CC=C(C=C1)F)CC1=CC=C(C=C1)OCCCCCC | Cl[C:15]([CH2:13][CH2:12][c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:32][cH:31]1)=[O:16].[OH:17][c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]2)[cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][CH:13]([CH3... | CCCCCCOc1ccc(CCC(=O)Cl)cc1.Oc1ccc(-c2ccc(F)cc2)cc1 | CCCCCCOc1ccc(CC(C)C(=O)Oc2ccc(-c3ccc(F)cc3)cc2)cc1 | null | null | O | Acylation | OtherReaction | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(CCc1ccccc1)Oc1ccc(-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C:4]-[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:10]-[CH;D3;+0:3](-[C:4]-[c:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 48 | [{"value": 48.0, "product": "CC(C(=O)OC1=CC=C(C=C1)C1=CC=C(C=C1)F)CC1=CC=C(C=C1)OCCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-Hydroxy-4'-fluorobiphenyl (2.1 g, 0.012 mol) was dissolved in pyridine (10 ml), and to the solution was added β-(4-hexyloxyphenyl)propionic acid chloride (3.0 g, 0.01 mol) with sufficient shaking, followed by allowing the resulting reaction solution to stand overnight, thereafter pouring it in water (100 ml), extract... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | O | null | 8 | CCCCCCOc1ccc(CCC(=O)Cl)cc1.Oc1ccc(-c2ccc(F)cc2)cc1>O>CCCCCCOc1ccc(CC(C)C(=O)Oc2ccc(-c3ccc(F)cc3)cc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-149cf621368447ca9478e75c0d11594b | CCCCCOc1ccc(CCC(=O)Cl)cc1.CCCc1ccc(-c2ccc(O)cc2)cc1>>CCCCCOc1ccc(CC(C)C(=O)Oc2ccc(-c3ccc(CCC)cc3)cc2)cc1 | OC1=CC=C(C=C1)C1=CC=C(C=C1)CCC.N1=CC=CC=C1.C(CCCC)OC1=CC=C(C=C1)CCC(=O)Cl>>CC(C(=O)OC1=CC=C(C=C1)C1=CC=C(C=C1)CCC)CC1=CC=C(C=C1)OCCCCC | Cl[C:14]([CH2:12][CH2:11][c:10]1[cH:9][cH:8][c:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:33][cH:32]1)=[O:15].[OH:16][c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([CH2:25][CH2:26][CH3:27])[cH:28][cH:29]2)[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH:12]([C... | CCCCCOc1ccc(CCC(=O)Cl)cc1.CCCc1ccc(-c2ccc(O)cc2)cc1 | CCCCCOc1ccc(CC(C)C(=O)Oc2ccc(-c3ccc(CCC)cc3)cc2)cc1 | null | null | O | Acylation | OtherReaction | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(CCc1ccccc1)Oc1ccc(-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C:4]-[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:10]-[CH;D3;+0:3](-[C:4]-[c:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | 4-Hydroxy-4'-propylbiphenyl (2.5 g, 0.012 mol) was dissolved in pyridine (10 ml) and to the solution was added β-(4-pentyloxyphenyl)propionic acid chloride (2.5 g, 0.01 mol) with sufficient shaking, followed by allowing the resulting reaction solution to stand overnight, pouring it in water (100 ml), extracting the res... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | O | null | 8 | CCCCCOc1ccc(CCC(=O)Cl)cc1.CCCc1ccc(-c2ccc(O)cc2)cc1>O>CCCCCOc1ccc(CC(C)C(=O)Oc2ccc(-c3ccc(CCC)cc3)cc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-872ec79cdd2e42ecb9a3d4b0e647897d | BrCCc1cccc(Br)c1Br>>BrC(Br)=Cc1ccccc1 | BrCCC=1C(=C(C=CC1)Br)Br.[OH-].[Na+].[Br-].C(C)[N+](CCCCC)(CC)CC>>BrC(=CC1=CC=CC=C1)Br | Br[c:9]1[cH:8][cH:7][cH:6][c:5]([CH2:4][CH2:2][Br:1])[c:10]1[Br:3]>>[Br:1][C:2]([Br:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | BrCCc1cccc(Br)c1Br | BrC(Br)=Cc1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 84b153b3b69ebce5def9af64ea344141980bb8d9e401ce4573d6e309559af488 | 5b120c389fcf30b9aa92d3fab7f855f7a7447308c566c8fdec7d2a54cd05faa5 | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[Br;D1;H0:8]):[c;H0;D3;+0:9]:1-[Br;H0;D1;+0:10]>>[Br;D1;H0:8]-[C;H0;D3;+0:7](-[Br;H0;D1;+0:10])=[CH;D2;+0:6]-[c:5]1:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:[cH;D2;+0:9]:1 | null | [] | null | null | null | null | A solution of 147.90 g. (0.431 mole) of 2-bromoethyldibromobenzene in 250 ml. of methylene chloride was stirred for 7 ks (2 hours) at 5 Hz (300 rpm) at 313 K. (40° C.) with 150 g (2.25 mole) of 60 percent sodium hydroxide solution and 3.12 g. (0.0124 mole) of triethylpentyl ammonium bromide. The product was washed with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary halide | Alkenyl halide.Alkenyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(Cl)Cl | null | null | BrCCc1cccc(Br)c1Br>C(Cl)Cl>BrC(Br)=Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d281ede4768c447887f8d1e077b75f5f | CC(=O)CCCCO[Si](C)(C)C(C)(C)C.CC1(C)OCC(CC=O)O1>>CC1(C)OCC(CC(O)CC(=O)CCCCO[Si](C)(C)C(C)(C)C)O1 | C(CCC)[Li].CCCCCC.C(C)(C)NC(C)C.[Si](C)(C)(C(C)(C)C)OCCCCC(C)=O.CC1(OCC(O1)CC=O)C>>[Si](C)(C)(C(C)(C)C)OCCCCC(CC(CC1OC(OC1)(C)C)O)=O | [CH3:10][C:11](=[O:12])[CH2:13][CH2:14][CH2:15][CH2:16][O:17][Si:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[CH3:24].[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][CH:8]=[O:9])[O:25]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][CH:8]([OH:9])[CH2:10][C:11](=[O:12])[CH2:13][CH2:14][CH2:15][CH2:16][O:17][Si:... | CC(=O)CCCCO[Si](C)(C)C(C)(C)C.CC1(C)OCC(CC=O)O1 | CC1(C)OCC(CC(O)CC(=O)CCCCO[Si](C)(C)C(C)(C)C)O1 | null | null | O.C1CCOC1 | C-C Coupling | OtherReaction | d08eb7b2615717189cce315501bb2cfa7ee3668e6d8eaa24218b092d1454a850 | 7d7139092067ff475e8e8a4ad6adb4833600ca969e282ed08dc56c016dccb864 | C1COCO1 | [#8:1]-[C:2]-[C:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5].[C:6]-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9]>>[#8:1]-[C:2]-[C:3]-[CH;D3;+0:4](-[OH;D1;+0:5])-[CH2;D2;+0:8]-[C:7](-[C:6])=[O;D1;H0:9] | null | [] | null | null | 20 | MINUTE | A solution of n-butyl lithium in hexane (119 ml, 1.6M, 0.19 mol) is added dropwise to a solution of diisopropylamine (19.3 g, 0.191 mol) in THF (100 ml) cooled in an ice bath. After the addition, the mixture is stirred for 20 minutes then cooled to -78°. A solution of 6-t-butyldimethylsilyloxy-hexan-2-one (40.0 g, 0.17... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Secondary alcohol | null | null | C1COCO1 | null | O.C1CCOC1 | null | 0.333333 | CC(=O)CCCCO[Si](C)(C)C(C)(C)C.CC1(C)OCC(CC=O)O1>O.C1CCOC1>CC1(C)OCC(CC(O)CC(=O)CCCCO[Si](C)(C)C(C)(C)C)O1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b1c8ce92ad7041c4bfcaac9c619c0317 | CCOC(=O)/C(C)=C/CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1>>C/C(=C\O)CCC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 | CC(C)C[AlH]CC(C)C.CC(C)(C)[SiH2]OC1CC(OC2(C1)OCCCC2)C/C=C(/C(=O)OCC)\C.C(C)(=O)OCC.CCCCCC.CO>>CC(C)(C)[SiH2]OC1CC(OC2(C1)OCCCC2)CC/C(=C/O)/C | CCO[C:3](/[C:2]([CH3:1])=[CH:5]/[CH2:6][CH:7]1[CH2:8][CH:9]([O:10][SiH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][C:17]2([CH2:18][CH2:19][CH2:20][CH2:21][O:22]2)[O:23]1)=[O:4]>>[CH3:1]/[C:2](=[CH:3]\[OH:4])[CH2:5][CH2:6][CH:7]1[CH2:8][CH:9]([O:10][SiH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][C:17]2([CH2:18]... | CCOC(=O)/C(C)=C/CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 | C/C(=C\O)CCC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 376e540652952c6e822fc93ca8a82f0b5972de8286f641931ad175283484e914 | 7b120640ba088dcf1d992af005dc3b1a94f9ed638ceed084bca0b30ee3d1d840 | C1CCC2(CCCCO2)OC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])/[C;H0;D3;+0:3](-[C;D1;H3:4])=[CH;D2;+0:5]/[C:6]-[C:7]-[#8:8]>>[#8:8]-[C:7]-[C:6]-[CH2;D2;+0:5]/[C;H0;D3;+0:3](-[C;D1;H3:4])=[CH;D2;+0:1]/[OH;D1;+0:2] | null | [] | null | null | null | null | A solution of 1M DIBAL (155 ml; 155 mmoles) is added dropwise to a solution of ethyl 4-[4-[(1,1-dimethylethyl)silyl]oxy-1,7-dioxaspiro[5.5]undec-2-yl]-2-methyl-2E-butenoate, (29.0 g; 70.3 mmoles) in methylene chloride (350 ml) with stirring under nitrogen at -78°. Upon completion of the addition, the reaction mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Enol | null | null | C1CCC2(CCCCO2)OC1 | HO- | C(Cl)Cl | null | null | CCOC(=O)/C(C)=C/CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1>C(Cl)Cl>C/C(=C\O)CCC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-97558f66ea4445e291a3e8e538aec74a | CCOC(=O)/C(C)=C/CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1>>C/C(C=O)=C\CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 | CC(C)(C)[SiH2]OC1CC(OC2(C1)OCCCC2)C/C=C(/C(=O)OCC)\C.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>CC(C)(C)[SiH2]OC1CC(OC2(C1)OCCCC2)C/C=C(/C=O)\C | CCO[C:3](/[C:2]([CH3:1])=[CH:5]/[CH2:6][CH:7]1[CH2:8][CH:9]([O:10][SiH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][C:17]2([CH2:18][CH2:19][CH2:20][CH2:21][O:22]2)[O:23]1)=[O:4]>>[CH3:1]/[C:2]([CH:3]=[O:4])=[CH:5]\[CH2:6][CH:7]1[CH2:8][CH:9]([O:10][SiH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][C:17]2([CH2:18][... | CCOC(=O)/C(C)=C/CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 | C/C(C=O)=C\CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 | null | null | CCOCC.C(Cl)Cl | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | C1CCC2(CCCCO2)OC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3](-[C;D1;H3:4])=[C:5]/[C:6]-[C:7]-[#8:8]>>[#8:8]-[C:7]-[C:6]/[C:5]=[C:3](\[C;D1;H3:4])-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | null | null | To a solution of ethyl 4-[4-[(1,1-dimethylethyl)silyl]oxy-1,7-dioxaspiro[5.5]undec-2-yl]-2-methyl-2E-butenoate, (10.0 g; 27.0 mmoles) in methylene chloride (160 ml) is added finely powdered pyridinium chlorochromate (PCC; 8.7 g; 40.5 mmoles) in a single portion with stirring under nitrogen at 25°. After twenty minutes ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | C1CCC2(CCCCO2)OC1 | HO- | CCOCC.C(Cl)Cl | null | null | CCOC(=O)/C(C)=C/CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1>CCOCC.C(Cl)Cl>C/C(C=O)=C\CC1CC(O[SiH2]C(C)(C)C)CC2(CCCCO2)O1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-af9b398431b84c62bf61834b7fe891d4 | O=C(NCCCC[C@H](OP(=O)(O)C(Cc1ccccc1)OC(=O)c1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1)OCc1ccccc1>>O=C(OCc1ccccc1)[C@@H]1CCCN1 | C(C1=CC=CC=C1)(=O)OC(CC1=CC=CC=C1)P(=O)(O[C@H](C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1)CCCCNC(=O)OCC1=CC=CC=C1)O.ClCCC(C(=O)[O-])(C)C.ClCCC(C(=O)[O-])(C)C.C([O-])([O-])=O.[K+].[K+]>>N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1 | O=C(NCCCC[C@H](OP(=O)(O)C(Cc1ccccc1)OC(=O)c1ccccc1)C(=O)[N:15]1[C@H:11]([C:2](=[O:1])[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:12][CH2:13][CH2:14]1)OCc1ccccc1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]1[CH2:12][CH2:13][CH2:14][NH:15]1 | O=C(NCCCC[C@H](OP(=O)(O)C(Cc1ccccc1)OC(=O)c1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1)OCc1ccccc1 | O=C(OCc1ccccc1)[C@@H]1CCCN1 | null | null | CN(C=O)C.C(C)(=O)OCC | Reduction | Hydrogenolysis of tertiary amines | f88b1249c2b143fc5d85cf9dcec02127d48320f42bb4a811327e633d965756da | 0149663aa25bdac246afd8acdcdc0f22a7ea1635947435099953c93482349ddc | O=C(OCc1ccccc1)[C@@H]1CCCN1 | O-P(=O)(-O-[C@H](-C-C-C-C-N-C(=O)-O-C-c1:c:c:c:c:c:1)-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-C(-C-c1:c:c:c:c:c:1)-O-C(=O)-c1:c:c:c:c:c:1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | 8 | HOUR | 1-[(S)-2-[[[1-(Benzoyloxy)-2-phenylethyl]hydroxyphosphinyl]oxy]-1-oxo-6-[[(phenylmethoxy)carbonyl]amino]hexyl]-L-proline, phenylmethyl ester from Example 5(d) is suspended in dry dimethylformamide and treated with chloromethylpivalate. After several hours, additional chloromethylpivalate and anhydrous potassium carbona... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Tertiary amide | Secondary amine | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | C1CCNC1 | c1ccccc1.C1CCNC1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 8 | O=C(NCCCC[C@H](OP(=O)(O)C(Cc1ccccc1)OC(=O)c1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1)OCc1ccccc1>CN(C=O)C.C(C)(=O)OCC>O=C(OCc1ccccc1)[C@@H]1CCCN1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6bd97a4a77f74b30bd8dfa2238b52eb2 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C1=CC=CC=C1)=O.C(CCC)[Li].C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.Cl>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.[CH:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | CCCCCC.COCCOC.C(C)OCC | C-C Coupling | OtherReaction | 3ebd6f16ba89cc360449fd30ab34ced1781fbed4a414d9e59bcf754777378132 | 2f319ce34b90d24c5ffbe402ed9c6fde7375d736dd872cea5121694203d4c1fd | [CH]=C(CC1CCCCC1)c1ccccc1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7]):c(-C(-C)-C):c:1.[O;H0;D1;+0:8]=[CH;D2;+0:9]-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:1>>[#7:4]-[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[CH;D3;+0:9](-[OH;D1;+0:8])-[CH;D3;+0... | null | [] | 0 | CELSIUS | 15 | MINUTE | A 1.5M solution (29 cc) of n-butyllithium in hexane is added to a solution of β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (9.15 g) in 1,2-dimethoxyethane (100 cc) kept under a nitrogen atmosphere at a temperature in the region of -75° C. The orange solution obtained is then stirred for 15 m... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aldehyde | Secondary alcohol | c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | CCCCCC.COCCOC.C(C)OCC | 0 | 0.25 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1>CCCCCC.COCCOC.C(C)OCC>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-834831151d84462eb2ebc4e92790c02c | CCN(CC)CCC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(CC)CC)C1=CC=CC=C1.C(C1=CC=CC=C1)=O>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH2:1]C)[CH2:3]C)[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.[CH:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH... | CCN(CC)CCC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1.O=Cc1ccccc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 3ebd6f16ba89cc360449fd30ab34ced1781fbed4a414d9e59bcf754777378132 | 2f319ce34b90d24c5ffbe402ed9c6fde7375d736dd872cea5121694203d4c1fd | [CH]=C(CC1CCCCC1)c1ccccc1 | C-[CH2;D2;+0:1]-[#7:2](-[C:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=N-N-S(=O)(=O)-c1:c(-C(-C)-C):c:c(-C(-C)-C):c:c:1-C(-C)-C)-[c:6](:[c:7]):[c:8])-[CH2;D2;+0:9]-C.[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[CH3;D1;+0:1]-[#7:2](-[CH3;D1;+0:9])-[C:3]-[C... | null | [] | null | null | null | null | By using a method similar to that described in Example 22, but starting from β-diethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (30 g) and benzaldehyde (6.9 cc), 4-diethylamino-1,2-diphenyl-2-buten-1-ol (Z) hydrochloride (3.2 g) is obtained, after recrystallisation from acetone, in the form of whit... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aldehyde | Secondary alcohol | c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | null | null | null | CCN(CC)CCC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3db90bb8ed7d4a83b2cd6d140be26831 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN2CCCC2)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN1CCCC1)C1=CC=CC=C1.C(C1=CC=CC=C1)=O>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]2[CH2:1]CC[CH2:3]2)[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.[CH:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN2CCCC2)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | c45b75d201fa0fc63b5af89abaf2e5cd11b5109f3038ca7df05c17bfe01224db | 2f319ce34b90d24c5ffbe402ed9c6fde7375d736dd872cea5121694203d4c1fd | [CH]=C(CC1CCCCC1)c1ccccc1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3]-[#7:4]2-[CH2;D2;+0:5]-C-C-[CH2;D2;+0:6]-2)-[c:7](:[c:8]):[c:9]):c(-C(-C)-C):c:1.[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[CH3;D1;+0:5]-[#7:4](-[CH3;D1;+0:6])-[C:3]... | null | [] | null | null | null | null | By using a method similar to that described in Example 22, but starting from β-(1-pyrrolidinyl)propiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g), and benzaldehyde (4.6 cc), 1,2-diphenyl-4-(1-pyrrolidinyl)-2-buten-1-ol (Z) hydrochloride (9.9 g) is obtained, after recrystallisation from a mixture of 2-prop... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aldehyde | Secondary alcohol | c1ccccc1.C1CC[NH]C1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN2CCCC2)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-48017fd73a1c4f57ad670594cebf5361 | CNC1C=C(c2ccccc2)C(c2ccccc2)O1.CO>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | [BH4-].[Na+].C1(=CC=CC=C1)C1OC(C=C1C1=CC=CC=C1)NC.CO>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | [CH3:1][NH:2][CH:4]1[CH:5]=[C:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH:13]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[O:14]1.O[CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | CNC1C=C(c2ccccc2)C(c2ccccc2)O1.CO | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ac9840b6515733b11f214a4630f191bc01cc9e09bc9ae80f0e97909cad33ebfc | 6ef7e83d526b7eb20c61e46462d34cb565cd38bffa4c0faa2c98debacd425740 | [CH]=C(CC1CCCCC1)c1ccccc1 | O-[CH3;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[CH;D3;+0:4]1-[C:5]=[C:6](-[c:7])-[C:8](-[c;H0;D3;+0:9]2:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:2)-[O;H0;D2;+0:15]-1>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[CH3;D1;+0:1])-[CH2;D2;+0:4]-[C:5]=[C:6](-[c:7])-[C:8](-[OH;D1;+0:15])-[CH;D3;+0:9]1-[CH2;D2;+0:10]-[C... | null | [] | 20 | CELSIUS | 18 | HOUR | Sodium borohydride (10.3 g) is added over approximately 30 minutes at a temperature in the region of 5° C. to a solution of 2,3-diphenyl-5-methylamino-2,5-dihydrofuran (9.7 g) in methanol (90 cc) and distilled water (10 cc). The reaction mixture is then stirred for 18 hours at a temperature in the region of 20° C., and... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine.Methanol | Secondary alcohol.Tertiary amine | C1=CCOC1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | Other | null | 20 | 18 | CNC1C=C(c2ccccc2)C(c2ccccc2)O1.CO>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-475f9554de1148c0944b4557eb4b3965 | Cl>>Cl | C1(=CC=CC=C1)C1OC(C=C1C1=CC=CC=C1)NC.[H-].[Na+].Cl.C1(=CC=CC=C1)C(=O)C(O)C1=CC=CC=C1.CN=CCP(OCC)(OCC)=O>>Cl.C1(=CC=CC=C1)C1OC(C=C1C1=CC=CC=C1)NC | [ClH:20]>>[ClH:20] | Cl | Cl | null | null | O1CCCC1.O.C(C)(=O)OCC.C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 20 | CELSIUS | 30 | MINUTE | 2,3-Diphenyl-5-methylamino-2,5-dihydrofuran can be prepared as follows: benzoin (29.7 g) dissolved in tetrahydrofuran (400 cc) is added to a suspension of sodium hydride (3.4 g) in tetrahydrofuran (50 cc) kept under a nitrogen atmosphere at a temperature in the region of 0° C., and the reaction mixture is stirred for 3... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O1CCCC1.O.C(C)(=O)OCC.C(C)OCC | 20 | 0.5 | Cl>O1CCCC1.O.C(C)(=O)OCC.C(C)OCC>Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2bec0db7777d45418f92d4f32b0400dd | CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | P(=O)(Cl)(Cl)Cl.CN(C=CC(=O)C1=CC=CC=C1)C.C1(=CC=CC=C1)S.[OH-].[Na+].C(#N)[BH3-].[Na+].Cl>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | [CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].S[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | O.C(C)N(CC)CC.C(Cl)(Cl)Cl.CO.C(Cl)Cl.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | d3753080378e8b20b0eab8cb0647dcbd1c690dba65847cdc72439e586f418fa6 | 7190e6f5f02f53d96c757c88d1ed0b3f7706d003dbd95bb86d4860d15fd3d555 | [CH]=C(CC1CCCCC1)c1ccccc1 | S-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[CH;D2;+0:10]=[CH;D2;+0:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[c:14](:[c:15]):[c:16]>>[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[CH2;D2;+0:10]-[CH;D2;+0:11]=[C;H0;D3;+0:12](-[C:17](-[OH;D1;+0:13])-[CH;D3;+0:1]1-... | null | [] | 0 | CELSIUS | 15 | MINUTE | Phosphorus oxychloride (2.5 cc) dissolved in methylene chloride (6 cc) is added dropwise at 0° C. to a solution of 3-dimethylaminoacrylophenone (5 g) in methylene chloride (16 cc). After stirring for 15 minutes at 0° C. and then 30 minutes at 20° C., the temperature is again brought down to 0° C. The precipitate formed... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Aromatic thiol | Secondary alcohol | c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | null | O.C(C)N(CC)CC.C(Cl)(Cl)Cl.CO.C(Cl)Cl.C(C)OCC | 0 | 0.25 | CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1>O.C(C)N(CC)CC.C(Cl)(Cl)Cl.CO.C(Cl)Cl.C(C)OCC>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4d74cf0142914f1a99f632065fe19ea0 | CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1>>CN(C)CC=C(Sc1ccccc1)c1ccccc1 | CN(C=CC(=O)C1=CC=CC=C1)C.C1(=CC=CC=C1)S.C(#N)[BH3-].[Na+]>>CN(CC=C(SC1=CC=CC=C1)C1=CC=CC=C1)C | O=[C:6]([CH:5]=[CH:4][N:2]([CH3:1])[CH3:3])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[SH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1 | CN(C)CC=C(Sc1ccccc1)c1ccccc1 | null | null | P(=O)(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 4762356a283a4dd15b9c6c402bec2a8d06b05d6260a2333b5a6b92e7043303a0 | 102db1557e8988ecf5e34231cc3ffb434e574fba60712f7d6b62030e75389393 | [CH]=C(Sc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[CH;D2;+0:2]=[CH;D2;+0:3]-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6])-[c:7](:[c:8]):[c:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[CH2;D2;+0:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (80 g), phosphorus oxychloride (40 cc), thiophenol (50.3 cc) and sodium cyanoborohydride (16 g), and crystallising the (Z)-isomer, a yellow solid is isolated after evaporation of the mother liquors under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1 | Other | P(=O)(Cl)(Cl)Cl | null | null | CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1>P(=O)(Cl)(Cl)Cl>CN(C)CC=C(Sc1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-76c9e3d8f8064427b92e1694b802ac91 | CCO.CN(C)C=CC(=O)c1ccccc1.Sc1ccc(Cl)cc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(#N)[BH3-].[Na+].C(C)O.CN(C=CC(=O)C1=CC=CC=C1)C.P(=O)(Cl)(Cl)Cl.Cl.ClC1=CC=C(C=C1)S>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | O[CH2:17][CH3:16].[CH3:1][N:2]([CH3:3])[CH:5]=[CH:6][C:13](=[O:14])[c:15]1[cH:12][cH:11][cH:10][cH:9][cH:20]1.S[c:7]1cc[c:18](Cl)[cH:19][cH:8]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | CCO.CN(C)C=CC(=O)c1ccccc1.Sc1ccc(Cl)cc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 405a039f51659caa1e8c43958e23f806a037c4c59238574dcd8dcbc4faa45ced | 54947926ef1b05f1c941996ef79177c8404f5f26356adf51e3a232e3b2392eab | [CH]=C(CC1CCCCC1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-S):c:c:1.O-[CH2;D2;+0:5]-[CH3;D1;+0:6].[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[CH;D2;+0:10]=[CH;D2;+0:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[c;H0;D3;+0:14]1:[cH;D2;+0:15]:[c:16]:[c:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:1>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-... | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.5 cc), p-chlorothiophenol (4.13 g) and sodium cyanoborohydride (1 g), and after evaporating the reaction mixture under reduced pressure (2.7 kPa) at 40° C., a residue is obtained, w... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone.Primary alcohol.Aromatic thiol | Secondary alcohol.Tertiary amine | c1ccccc1.c1ccccc1 | c1ccccc1.C1CCCCC1 | c1ccccc1.C1CCCCC1 | Other | C(C)OCC | null | null | CCO.CN(C)C=CC(=O)c1ccccc1.Sc1ccc(Cl)cc1>C(C)OCC>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f4d74320692a4dfaa4096e7c39523c9c | CN(C)C=CC(=O)c1ccccc1.Sc1ccncc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(#N)[BH3-].[Na+].P(=O)(Cl)(Cl)Cl.SC1=CC=NC=C1.Cl.CN(C=CC(=O)C1=CC=CC=C1)C.C(C(=O)O)(=O)O>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | [CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].S[c:15]1[cH:16][cH:17]n[cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | CN(C)C=CC(=O)c1ccccc1.Sc1ccncc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | da58b9b01ed6d9c6b3cf459555d1b76f311474cd5082f582d3af10df6ccbb5b8 | 7190e6f5f02f53d96c757c88d1ed0b3f7706d003dbd95bb86d4860d15fd3d555 | [CH]=C(CC1CCCCC1)c1ccccc1 | S-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:n:[cH;D2;+0:4]:[cH;D2;+0:5]:1.[C;D1;H3:6]-[#7:7](-[C;D1;H3:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[c:13](:[c:14]):[c:15]>>[C;D1;H3:6]-[#7:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[CH;D2;+0:10]=[C;H0;D3;+0:11](-[C:16](-[OH;D1;+0:12])-[CH;D3;+0:1]1-[CH2;D2;+0:2]... | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (10 g), phosphorus oxychloride (5 cc), 4-mercaptopyridine (6.35 g) and sodium cyanoborohydride (2 g), a chestnut-coloured residue is obtained which is taken up in water (100 cc). The solution is acidified to pH 2 b... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Aromatic thiol | Secondary alcohol | c1ccncc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | null | O.C(C)O | null | null | CN(C)C=CC(=O)c1ccccc1.Sc1ccncc1>O.C(C)O>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3065eef9ebf54707a979828bb3decf18 | CN(C)C=CC(=O)c1ccc(F)cc1.Sc1ccccc1>>CN(C)CC=C(Sc1ccccc1)c1ccc(F)cc1 | FC1=CC=C(C=C1)C(C=CN(C)C)=O.Cl.[OH-].[Na+].C1(=CC=CC=C1)S.C(#N)[BH3-].[Na+].P(=O)(Cl)(Cl)Cl>>CN(CC=C(SC1=CC=CC=C1)C1=CC=C(C=C1)F)C | O=[C:6]([CH:5]=[CH:4][N:2]([CH3:1])[CH3:3])[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1.[SH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1 | CN(C)C=CC(=O)c1ccc(F)cc1.Sc1ccccc1 | CN(C)CC=C(Sc1ccccc1)c1ccc(F)cc1 | null | null | C(Cl)(Cl)Cl.C(C)(C)O.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4762356a283a4dd15b9c6c402bec2a8d06b05d6260a2333b5a6b92e7043303a0 | 102db1557e8988ecf5e34231cc3ffb434e574fba60712f7d6b62030e75389393 | [CH]=C(Sc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[CH;D2;+0:2]=[CH;D2;+0:3]-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6])-[c:7](:[c:8]):[c:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[CH2;D2;+0:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 1-(4-fluorophenyl)-3-dimethylamino-2-propen-1-one (10 g), phosphorus oxychloride (4.76 cc), thiophenol (5.57 cc) and sodium cyanoborohydride (1.92 g), a residue is obtained which is taken up in chloroform. The solution is then adjusted to pH 1... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1 | Other | C(Cl)(Cl)Cl.C(C)(C)O.C(C)OCC | null | null | CN(C)C=CC(=O)c1ccc(F)cc1.Sc1ccccc1>C(Cl)(Cl)Cl.C(C)(C)O.C(C)OCC>CN(C)CC=C(Sc1ccccc1)c1ccc(F)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cf43cabef56e42ff831c0043b831c695 | CN(C)C=CC(=O)c1ccc(Br)cc1.Sc1ccccc1>>CN(C)CC=C(Sc1ccccc1)c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(C=CN(C)C)=O.[OH-].[Na+].C1(=CC=CC=C1)S.C(#N)[BH3-].[Na+].Cl.P(=O)(Cl)(Cl)Cl>>BrC1=CC=C(C=C1)C(=CCN(C)C)SC1=CC=CC=C1 | O=[C:6]([CH:5]=[CH:4][N:2]([CH3:1])[CH3:3])[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1.[SH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1 | CN(C)C=CC(=O)c1ccc(Br)cc1.Sc1ccccc1 | CN(C)CC=C(Sc1ccccc1)c1ccc(Br)cc1 | null | null | CCOCC.C(Cl)(Cl)Cl.C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 4762356a283a4dd15b9c6c402bec2a8d06b05d6260a2333b5a6b92e7043303a0 | 102db1557e8988ecf5e34231cc3ffb434e574fba60712f7d6b62030e75389393 | [CH]=C(Sc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[CH;D2;+0:2]=[CH;D2;+0:3]-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6])-[c:7](:[c:8]):[c:9].[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[CH2;D2;+0:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 1-(4-bromophenyl)-3-dimethylamino-2-propen-1-one (10 g), phosphorus oxychloride (3.64 g), thiophenol (4.2 cc) and sodium cyanoborohydride (1.47 g), a residue is obtained which is taken up in chloroform. The solution is adjusted to pH 10 by add... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1 | Other | CCOCC.C(Cl)(Cl)Cl.C(C)(C)O | null | null | CN(C)C=CC(=O)c1ccc(Br)cc1.Sc1ccccc1>CCOCC.C(Cl)(Cl)Cl.C(C)(C)O>CN(C)CC=C(Sc1ccccc1)c1ccc(Br)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-437d9ff9e7c043fe95a9f0b8da7e0249 | CN(C)C=CC(=O)c1ccccc1.Sc1ccc(Br)cc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | CN(C=CC(=O)C1=CC=CC=C1)C.[OH-].[Na+].BrC1=CC=C(C=C1)S.C(#N)[BH3-].[Na+].Cl.P(=O)(Cl)(Cl)Cl>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | [CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].S[c:15]1[cH:16][cH:17][c:18](Br)[cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | CN(C)C=CC(=O)c1ccccc1.Sc1ccc(Br)cc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | CCOCC.C(Cl)(Cl)Cl.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1e537e83cebfd43b146ccf8ea392cf5d3050879ecbe689f3ec93b9cce50b64c2 | ddd1516ad43f47fa7b86b0594e44d52ec4b102fdedd9f20b49005145737c746a | [CH]=C(CC1CCCCC1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-S):[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[CH;D2;+0:10]=[CH;D2;+0:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[c:14](:[c:15]):[c:16]>>[C;D1;H3:7]-[#7:8](-[C;D1;H3:9])-[CH2;D2;+0:10]-[CH;D2;+0:11]=[C;H0;D3;+0:12](-[C:17](-[OH;D1;+0:13])-[CH;D3;... | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.47 cc), 4-bromothiophenol (5.39 g) and sodium cyanoborohydride (1 g), a chestnut-coloured residue is obtained which is taken up in chloroform. The solution is made alkaline to pH 10... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone.Aromatic thiol | Secondary alcohol | c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | Br- | CCOCC.C(Cl)(Cl)Cl.C(C)O | null | null | CN(C)C=CC(=O)c1ccccc1.Sc1ccc(Br)cc1>CCOCC.C(Cl)(Cl)Cl.C(C)O>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d9922a320104492598aad6f7450006e5 | CCN(CC)CC.CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1.CO.[OH-]>>CCOC(=O)OC(C(=CCN)c1ccccc1)c1ccccc1 | [OH-].[Na+].C(C)N(CC)CC.C(CCS)S.C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O.CO>>NCC=C(C(OC(=O)OCC)C1=CC=CC=C1)C1=CC=CC=C1 | CCN(CC)[CH2:2][CH3:1].C[N:11](C)[CH2:10][CH:9]=[C:8]([CH:7]([OH:6])[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[OH:3][CH3:4].[OH-:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6][CH:7]([C:8](=[CH:9][CH2:10][NH2:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:... | CCN(CC)CC.CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1.CO.[OH-] | CCOC(=O)OC(C(=CCN)c1ccccc1)c1ccccc1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 623b1b8dd75701180f14d12f6469fe8fa4bef224afaf799df33b41aafa681763 | 3189d70a09073085feb5c65a6b0c23cebbe2ad41207a23d57ad58e1eb3599814 | [CH]=C(Cc1ccccc1)c1ccccc1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[C;D1;H3:2].C-[N;H0;D3;+0:3](-C)-[C:4]-[C:5]=[C:6](-[c:7])-[C:8](-[OH;D1;+0:9])-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[CH2;D2;+0:15]-1.[CH3;D1;+0:16]-[OH;D1;+0:17].[OH-;D0:18]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:17]-[C;H0;D3;+0:16](=[O;H0;D1;+0:18])-[O;H... | null | [] | null | null | 18 | HOUR | Triethylamine (1.05 cc) and 1,3-propanedithiol (0.74 cc) are added to a solution of 4-azido-1,2-diphenyl-1-ethoxycarbonyloxy-2-butene (Z) (0.5 g) in methanol (7.5 cc). The mixture is stirred under a nitrogen atmosphere for 18 hours at ambient temperature. The reaction mixture is then poured into water (10 cc), adjusted... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Tertiary amine.Tertiary amine.Methanol | Carbonic Ester.Primary amine | C1CCCCC1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | O | null | 18 | CCN(CC)CC.CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1.CO.[OH-]>O>CCOC(=O)OC(C(=CCN)c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bafaf1cd37ff4a9e9438a2f3b095ad7f | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1F>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.FC1=C(C=O)C=CC=C1>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.F[c:20]1[c:15]([CH:13]=[O:14])[cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1F | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | e9d48bb333e25370f39508268f8fab0013d8c9d2216ebb4925f8d09549804f1a | 05339c96fb0a21edb48547dfb79b5c1cd719c10814e28a0fe9b4657ab6ae568d | [CH]=C(CC1CCCCC1)c1ccccc1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7]):c(-C(-C)-C):c:1.F-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[CH;D2;+0:14]=[O;H0;D1;+0:15]>>[#7:4]-[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[CH;D3;+0:14](-[OH;D1;+0:15])-[CH... | null | [] | null | null | null | null | By using a method similar to that described in Example 22, but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (10 g) and 2-fluorobenzaldehyde (2.6 cc), 4-dimethylamino-1-(2-fluorophenyl)-2-phenyl-2-buten-1-ol (Z) hydrochloride (3.5 g) is obtained in the form of a white powder mel... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HF | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1ccccc1F>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e8cacf0dd8e14469911f26b32ae1fd9e | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1cccc(Br)c1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.BrC=1C=C(C=O)C=CC1>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.Br[c:19]1[cH:18][cH:17][cH:16][c:15]([CH:13]=[O:14])[cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1cccc(Br)c1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | e9d48bb333e25370f39508268f8fab0013d8c9d2216ebb4925f8d09549804f1a | 05339c96fb0a21edb48547dfb79b5c1cd719c10814e28a0fe9b4657ab6ae568d | [CH]=C(CC1CCCCC1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[cH;D2;+0:8]:1.C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:9](-[CH2;D2;+0:10]-[C:11]-[#7:12])-[c:13](:[c:14]):[c:15]):c(-C(-C)-C):c:1>>[#7:12]-[C:11]-[CH;D2;+0:10]=[C;H0;D3;+0:9](-[CH;D3;+0:6](-[OH;D1;+0:7])... | null | [] | null | null | null | null | By using a method similar to that described in Example 22, but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and 3-bromobenzaldehyde (5.6 cc), 1-(3-bromophenyl)-4dimethylamino-2-phenyl-2-buten-1-ol (Z) hydrochloride (11.3 g ) is obtained in the form of a white solid melti... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HBr | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=Cc1cccc(Br)c1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1119c717db4a4fe39ded8a3d3c1e6c12 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.Cc1ccccc1C=O>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.C=1(C(=CC=CC1)C=O)C>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.C[c:20]1[c:15]([CH:13]=[O:14])[cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.Cc1ccccc1C=O | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 3ebd6f16ba89cc360449fd30ab34ced1781fbed4a414d9e59bcf754777378132 | 2f319ce34b90d24c5ffbe402ed9c6fde7375d736dd872cea5121694203d4c1fd | [CH]=C(CC1CCCCC1)c1ccccc1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7]):c(-C(-C)-C):c:1.C-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[CH;D2;+0:14]=[O;H0;D1;+0:15]>>[#7:4]-[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[CH;D3;+0:14](-[OH;D1;+0:15])-[CH... | 85.4 | [{"value": 85.4, "product": "C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By using a method similar to that described in Example 22, but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and from o-tolualdehyde (5.78 g), 4-dimethylamino-1-(2-methylphenyl)-2-phenyl-2-buten-1-ol (Z) hydrochloride (10.2 g) is obtained in the form of a white powder mel... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aldehyde | Secondary alcohol | c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.Cc1ccccc1C=O>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c08a21ca488a4c3cba0c0cc8ce71679a | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.COc1ccccc1C=O>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.C(C=1C(=CC=CC1)OC)=O>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.CO[c:20]1[c:15]([CH:13]=[O:14])[cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.COc1ccccc1C=O | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | dbdcade79204e0a56ee5dd8ca835909d31858cdd25556e93a2e48c42de6cfc67 | a6ca4bb4b6273366d3220f5e21425d37f94d720df0cf6fa944abf75c839397d5 | [CH]=C(CC1CCCCC1)c1ccccc1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7]):c(-C(-C)-C):c:1.C-O-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[CH;D2;+0:14]=[O;H0;D1;+0:15]>>[#7:4]-[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[CH;D3;+0:14](-[OH;D1;+0:15])-[... | 60.3 | [{"value": 60.3, "product": "C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By using a method similar to that described in Example 22, but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and from o-anisaldehyde (6.5 g), 4-dimethylamino-1-(2-methoxyphenyl)-2-phenyl-2-buten-1-ol (Z) (7.2 g) is obtained in the form of a white powder melting at 77° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aldehyde.Ether | Secondary alcohol | c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.COc1ccccc1C=O>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-db19edbbd8e3453fbede5bf34086d2cf | COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CC(OC)N(C)C)C1=CC=CC=C1.C(C1=CC=CC=C1)=O>>C1(CCCCC1)C(C(=CCN(C)C)C1=CC=CC=C1)O | CO[CH:4]([N:2]([CH3:1])[CH3:3])[CH2:5][C:6](=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[CH:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH:13]([OH:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2... | COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C.O=Cc1ccccc1 | CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | dbdcade79204e0a56ee5dd8ca835909d31858cdd25556e93a2e48c42de6cfc67 | a6ca4bb4b6273366d3220f5e21425d37f94d720df0cf6fa944abf75c839397d5 | [CH]=C(CC1CCCCC1)c1ccccc1 | C-O-[CH;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=N-N-S(=O)(=O)-c1:c(-C(-C)-C):c:c(-C(-C)-C):c:c:1-C(-C)-C)-[c:4](:[c:5]):[c:6])-[#7:7](-[C;D1;H3:8])-[C;D1;H3:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[C;D1;H3:8]-[#7:7](-[C;D1;H3:9])-[CH2;D2... | null | [] | null | null | null | null | By using a method similar to that described in Example 22, but starting from β-dimethylamino-3-methoxypropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (21.7 g) and from benzaldehyde (5.4 cc), 4-dimethylamino-2-(3-methoxyphenyl)-1-phenyl-2-buten-1-ol (Z) hydrochloride (11.9 g) is obtained in the form of a white... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aldehyde.Ether | Secondary alcohol | c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | null | null | null | COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C(O)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-09f2dc9bd7e647de8c42509b9a2f23f0 | COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C.COC(CC(=O)c1ccccc1)N(C)C>>COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C | Cl.CN(C(CC(=O)C1=CC=CC=C1)OC)C.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CC(OC)N(C)C)C1=CC=CC=C1.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN>>Cl.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CC(OC)N(C)C)C1=CC=CC=C1 | COC(CC(c1ccccc1)=[N:6][NH:7][S:8](=[O:9])(=[O:10])[c:11]1[c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][c:22]1[CH:23]([CH3:24])[CH3:25])N(C)C.O=[C:5]([CH2:4][CH:3]([O:2][CH3:1])[N:32]([CH3:33])[CH3:34])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][O:2][CH:3]([CH2:4][C:5](=[N:6][... | COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C.COC(CC(=O)c1ccccc1)N(C)C | COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0c2b5a2a8b3a7ec9ac4dc44d972abcaaa626b1aa98d94ffc0bbb0902425de6b3 | 27a0181f8ce20ba7c73a6073a00fbe45a31cc81b202698f805c5c59d0572138b | O=S(=O)(NN=Cc1ccccc1)c1ccccc1 | C-O-C(-C-C(=[N;H0;D2;+0:1]-[#7:2]-[#16:3])-c1:c:c:c:c:c:1)-N(-C)-C.O=[C;H0;D3;+0:4](-[C:5]-[C:6])-[c:7](:[c:8]):[c:9]>>[#16:3]-[#7:2]-[N;H0;D2;+0:1]=[C;H0;D3;+0:4](-[C:5]-[C:6])-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | β-Dimethylamino-3-methoxypropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone can be prepared by a method similar to that described in Example 22 for the preparation of β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone, but starting from 2,4,6-triisopropylbenzenesulphonylhydrazine (25.3 g) a... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone.Ether.Tertiary amine | Hydrazone | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C.COC(CC(=O)c1ccccc1)N(C)C>>COC(CC(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1)N(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-057736d84dce4583ac2843e145deeba9 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=C1CCCc2ccccc21>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.C1CC2=CC=CC=C2C(=O)C1>>OC1(CCCC2=CC=CC=C12)C(=CCN(C)C)C1=CC=CC=C1 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c(C(C)C)c1.[C:13]1(=[O:14])[CH2:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13]1([OH:14])[CH2:15][CH2:... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=C1CCCc2ccccc21 | CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | null | null | null | C-C Coupling | OtherReaction | 962f47f6f8a0ba8f5776d76748b695cc760c3fd02e61302b9e486bc76a80ee92 | be7df71ea82e782c3aad2bcb7c0413b1294333bcd0b030726d2fd5180ffb4746 | [CH]=C(c1ccccc1)C1CCCc2ccccc21 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7]):c(-C(-C)-C):c:1.[C:8]-[C:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14]>>[#7:4]-[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[c:5](:[c:6]):[c:7])-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[C:9]-[C:8])-[c:12](:[c:13]):[c... | null | [] | null | null | null | null | By using a method similar to that described in Example 22 but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and from α-tetralone (6.4 cc), 1-(1-hydroxy-1,2,3,4-tetrahydro-1-naphthyl)-3-dimethylamino-1-phenyl-1-propene (Z) (3.8 g) is obtained in the form of a white powder ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Ketone | Tertiary alcohol | c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=C1CCCc2ccccc21>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dd5c9bc449b941468df29aa629851196 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=C1CCCCC1>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CCN(C)C)C1=CC=CC=C1.C1(CCCCC1)=O>>OC1(CCCC2=CC=CC=C12)C(=CCN(C)C)C1=CC=CC=C1 | CC(C)c1c[c:22](C(C)C)[c:23](S(=O)(=O)NN=[C:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:18](C(C)C)[cH:17]1.[C:13]1(=[O:14])[CH2:15][CH2:16][CH2:21][CH2:20][CH2:19]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13]1([OH:14])[CH2:15][CH2:16][C... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=C1CCCCC1 | CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | null | null | null | C-C Coupling | OtherReaction | a261bd99a8a92a2d89f9c3684f105c3de74eb8d4a99c9cfa511931cd4e34c000 | be7df71ea82e782c3aad2bcb7c0413b1294333bcd0b030726d2fd5180ffb4746 | [CH]=C(c1ccccc1)C1CCCc2ccccc21 | C-C(-C)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:c(-C(-C)-C):c:[c;H0;D3;+0:3](-C(-C)-C):[c;H0;D3;+0:4]:1-S(=O)(=O)-N-N=[C;H0;D3;+0:5](-[CH2;D2;+0:6]-[C:7]-[#7:8])-[c:9](:[c:10]):[c:11].[O;H0;D1;+0:12]=[C;H0;D3;+0:13]1-[C:14]-[CH2;D2;+0:15]-[CH2;D2;+0:16]-[CH2;D2;+0:17]-[CH2;D2;+0:18]-1>>[#7:8]-[C:7]-[CH;D2;+0:6]=[C;H0;D3;+0:5](-[c... | null | [] | null | null | null | null | By using a procedure similar to that described in Example 22 but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and from cyclohexanone (5 cc), 1-(1-hydroxy-1-cyclohexyl)-3-dimethylamino-1-phenyl-1-propene (Z) hydrochloride (6 g) is obtained in the form of a white powder me... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Ketone | Tertiary alcohol | c1ccccc1.C1CCCCC1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CCN(C)C)c2ccccc2)c(C(C)C)c1.O=C1CCCCC1>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e86a3e9ff2604fdf978a729dc5841fcf | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN)c(C(C)C)c1.CN1CCCC1CC(=O)c1ccccc1>>CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CC2CCCN2C)c2ccccc2)c(C(C)C)c1 | C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CC1N(CCC1)C)C1=CC=CC=C1.CN(CCC(=O)C1=CC=CC=C1)C.Cl.CN1C(CCC1)CC(=O)C1=CC=CC=C1>>Cl.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(CC1N(CCC1)C)C1=CC=CC=C1 | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[c:10]([S:11](=[O:12])(=[O:13])[NH:14][NH2:15])[c:30]([CH:31]([CH3:32])[CH3:33])[cH:34]1.O=[C:16]([CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][N:22]1[CH3:23])[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6]([CH:7]([CH3:8])[CH... | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN)c(C(C)C)c1.CN1CCCC1CC(=O)c1ccccc1 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CC2CCCN2C)c2ccccc2)c(C(C)C)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 83882590079d324612170330ec542715e8ce71411b1b2946e5f0d75ea75ad4dd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | O=S(=O)(NN=C(CC1CCCN1)c1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7].[#16:8]-[#7:9]-[NH2;D1;+0:10]>>[#16:8]-[#7:9]-[N;H0;D2;+0:10]=[C;H0;D3;+0:1](-[C:2]-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | α-(1-Methyl-2-pyrrolidinyl)acetophenone 2,4,6-triisopropylbenzenesulphonylhydrazone can be prepared by a method similar to that described in Example 22 for the preparation of β-dimethylaminopropiophenone, 2,4,6-triisopropylbenzenesulphonylhydrazone, but starting from 2,4,6-triisopropylbenzenesulphonylhydrazine (30.6 g)... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | null | null | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN)c(C(C)C)c1.CN1CCCC1CC(=O)c1ccccc1>>CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=C(CC2CCCN2C)c2ccccc2)c(C(C)C)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e523d3bf6d6f4be7aaccce500d9e3658 | CC(CN(C)C)C(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1.O=Cc1ccccc1>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | C(C1=CC=CC=C1)=O.C(C)(C)(C)[Li].C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(C(CN(C)C)C)C1=CC=CC=C1.Cl.Cl>>OC1(CCCC2=CC=CC=C12)C(=CCN(C)C)C1=CC=CC=C1 | CC(C)c1cc(C(C)C)c(S(=O)(=O)NN=[C:6]([CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH3:15])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)c([CH:17](C)[CH3:16])c1.[CH:13](=[O:14])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13]1([OH:14])[CH2:15][CH2:16... | CC(CN(C)C)C(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1.O=Cc1ccccc1 | CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | null | null | O.CCCCC.CC(=O)C.COCCOC.C(C)OCC | C-C Coupling | OtherReaction | 1cbd32a051eafbbb080795e8a663b5e7083fd4b13a4460c3abba6e7e78ec81ce | 993855a2ea4c79485046a4d8ea0ca7051719a1c4ea0d6f63d12db845ee36cf08 | [CH]=C(c1ccccc1)C1CCCc2ccccc21 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-N-N=[C;H0;D3;+0:1](-[CH;D3;+0:2](-[CH3;D1;+0:3])-[C:4]-[#7:5])-[c:6](:[c:7]):[c:8]):c(-[CH;D3;+0:9](-C)-[CH3;D1;+0:10]):c:1.[O;H0;D1;+0:11]=[CH;D2;+0:12]-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[c:16]:[c:17]:[cH;D2;+0:18]:1>>[#7:5]-[C:4]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[c:6](:[c:7]):[c:8])-[C;... | null | [] | 15 | CELSIUS | 20 | MINUTE | A 1.9M solution (30.4 cc) of tert-butyllithium in pentane is added to a solution of β-dimethylamino-α-methylpropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (10.9 g) in 1,2-dimethoxyethane (109 cc), kept under nitrogen atmosphere at a temperature in the region of -75° C. Once the addition has been completed th... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Aldehyde | Tertiary alcohol | c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | O.CCCCC.CC(=O)C.COCCOC.C(C)OCC | 15 | 0.333333 | CC(CN(C)C)C(=NNS(=O)(=O)c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1ccccc1.O=Cc1ccccc1>O.CCCCC.CC(=O)C.COCCOC.C(C)OCC>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cad463dd5b794184bd05ea983ee11d4c | Cl>>Cl | O.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(C(CN(C)C)C)C1=CC=CC=C1.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN.Cl.CC(C(=O)C1=CC=CC=C1)CN(C)C>>Cl.C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)NN=C(C(CN(C)C)C)C1=CC=CC=C1 | [ClH:34]>>[ClH:34] | Cl | Cl | null | null | C(C)(=O)O.C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 24 | HOUR | β-Dimethylamino-α-methylpropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone can be prepared as follows: 2,4,6-triisopropylbenzenesulphonylhydrazine (23.8 g) is added to α-methyl-β-dimethylaminopropiophenone hydrochloride (16.3 g) dissolved in methylene chloride (150 cc) and acetic acid (5 cc). The solution is sti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(=O)O.C(Cl)Cl | null | 24 | Cl>C(C)(=O)O.C(Cl)Cl>Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0cce6a139615472cb7594067073fa6a4 | CC(C)O.CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1Cl>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | C(#N)[BH3-].[Na+].C(C)(C)O.CN(C=CC(=O)C1=CC=CC=C1)C.P(=O)(Cl)(Cl)Cl.Cl.ClC1=C(C=CC=C1)S>>OC1(CCCC2=CC=CC=C12)C(=CCN(C)C)C1=CC=CC=C1 | O[CH:13]([CH3:15])[CH3:17].[CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].S[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1Cl>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13]1([OH:14])[CH2:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22]... | CC(C)O.CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1Cl | CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 8d83f6ca45ac827a93af4e5a9762e2536a73a6aa8fbe03ff6c989f700c3a6d78 | 4c02746a7bcb3f60b9410fd6f58e28fd8dc6dcef087ecf59d23b8c4d87859c2b | [CH]=C(c1ccccc1)C1CCCc2ccccc21 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-S.O-[CH;D3;+0:7](-[CH3;D1;+0:8])-[CH3;D1;+0:9].[C;D1;H3:10]-[#7:11](-[C;D1;H3:12])-[CH;D2;+0:13]=[CH;D2;+0:14]-[C;H0;D3;+0:15](=[O;H0;D1;+0:16])-[c:17](:[c:18]):[c:19]>>[C;D1;H3:10]-[#7:11](-[C;D1;H3:12])-[CH2;D2;+0:13]-[CH;D2;+0:14]=[C;H0;D3;+0:15](-[c:17](:[... | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (6.1 g), phosphorus oxychloride (3 cc), 2-chlorothiophenol (5 g) and sodium cyanoborohydride (1.3 g), and after evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C., a yellow oil is o... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone.Secondary alcohol.Aromatic thiol | Tertiary alcohol | c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HCl | C(C)OCC | null | null | CC(C)O.CN(C)C=CC(=O)c1ccccc1.Sc1ccccc1Cl>C(C)OCC>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-afe170f81add48948f8c1aa954ce0259 | CC(C)=O.CN(C)C=CC(=O)c1ccccc1.Sc1cccc(Cl)c1>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | C(#N)[BH3-].[Na+].CC(=O)C.CN(C=CC(=O)C1=CC=CC=C1)C.P(=O)(Cl)(Cl)Cl.Cl.ClC=1C=C(C=CC1)S>>OC1(CCCC2=CC=CC=C12)C(=CCN(C)C)C1=CC=CC=C1 | O=[C:13]([CH3:22])[CH3:23].[CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].S[c:20]1[cH:15][cH:16][cH:17][c:18](Cl)[cH:19]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13]1([OH:14])[CH2:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:2... | CC(C)=O.CN(C)C=CC(=O)c1ccccc1.Sc1cccc(Cl)c1 | CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | null | null | C(C)OCC | Aromatic Heterocycle Formation | OtherReaction | 5d4fb066042b9c0d5a9632ed89dde9c7ca52f374909b06d95f813f88e3166c0a | d283927a0205aa30e926eea5d70f92cd65ba9dc33533b37bc72d16ef464b4bee | [CH]=C(c1ccccc1)C1CCCc2ccccc21 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-S):[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.O=[C;H0;D3;+0:7](-[CH3;D1;+0:8])-[CH3;D1;+0:9].[C;D1;H3:10]-[#7:11](-[C;D1;H3:12])-[CH;D2;+0:13]=[CH;D2;+0:14]-[C;H0;D3;+0:15](=[O;H0;D1;+0:16])-[c:17](:[c:18]):[c:19]>>[C;D1;H3:10]-[#7:11](-[C;D1;H3:12])-[CH2;D2;+0:13]-[CH;D2;+0:14]=[... | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.5 cc), 3-chlorothiophenol (4.13 g) and sodium cyanoborohydride (1 g), and after evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C., a residue is obt... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone.Ketone.Aromatic thiol | Tertiary alcohol | c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | Other | C(C)OCC | null | null | CC(C)=O.CN(C)C=CC(=O)c1ccccc1.Sc1cccc(Cl)c1>C(C)OCC>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3d6a0a5566b347cb9e82ee1e43eb1bee | CC(C)O.CN(C)C=CC(=O)c1ccccc1.Cc1ccc(S)cc1>>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | C(#N)[BH3-].[Na+].C(C)(C)O.CN(C=CC(=O)C1=CC=CC=C1)C.P(=O)(Cl)(Cl)Cl.Cl.CC1=CC=C(C=C1)S>>OC1(CCCC2=CC=CC=C12)C(=CCN(C)C)C1=CC=CC=C1 | O[CH:20]([CH3:19])[CH3:21].[CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].S[c:23]1[cH:13][cH:15][c:16]([CH3:17])[cH:18][cH:22]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:13]1([OH:14])[CH2:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21... | CC(C)O.CN(C)C=CC(=O)c1ccccc1.Cc1ccc(S)cc1 | CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 | null | null | C(C)OCC | Aromatic Heterocycle Formation | OtherReaction | 3c273c4d6d071f4bac60c71def7bc310168d971792cc9dc702b87a6eb4b960d8 | 434d667421f49e168b0a4474941b0a4a16434d6ae30c3f3d228a76739210d470 | [CH]=C(c1ccccc1)C1CCCc2ccccc21 | O-[CH;D3;+0:1](-[CH3;D1;+0:2])-[CH3;D1;+0:3].S-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[CH3;D1;+0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H3:11]-[#7:12](-[C;D1;H3:13])-[CH;D2;+0:14]=[CH;D2;+0:15]-[C;H0;D3;+0:16](=[O;H0;D1;+0:17])-[c:18](:[c:19]):[c:20]>>[C;D1;H3:11]-[#7:12](-[C;D1;H3:13])-[CH2;D2;+0:14... | null | [] | null | null | null | null | By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.47 cc), 4-methylthiophenol (3.55 g) and sodium cyanoborohydride (1 g), and after evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C., an orange oil i... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Secondary alcohol.Aromatic thiol | Tertiary alcohol | c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | Other | C(C)OCC | null | null | CC(C)O.CN(C)C=CC(=O)c1ccccc1.Cc1ccc(S)cc1>C(C)OCC>CN(C)CC=C(c1ccccc1)C1(O)CCCc2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2b42240b607b49ddbd42f80892057fb4 | C=Cc1ccccc1.CC(C)c1ccccc1>>CC(C)c1ccccc1C(C)c1ccccc1 | C1(=CC=CC=C1)C(C)C.C=CC1=CC=CC=C1>>C1(=CC=CC=C1)C(C)C1=C(C=CC=C1)C(C)C | [CH:10](=[CH2:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH:10]([CH3:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C=Cc1ccccc1.CC(C)c1ccccc1 | CC(C)c1ccccc1C(C)c1ccccc1 | null | S(O)(O)(=O)=O | null | C-C Coupling | Friedel-Crafts alkylation | f6021e53f57d07d48a856391b21137517c9bd669381174a55381b6219a6afd68 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccc(Cc2ccccc2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[CH;D3;+0:2](-[CH3;D1;+0:1])-[c:3](:[c:4]):[c:5]):[c:10]:[c:11] | null | [] | null | null | null | null | Aralkylation of cumene with styrene was carried out in the presence of sulfuric acid catalyst. From the reaction product, a fraction mainly containing 1-phenyl-1-(isopropylphenyl)ethane was obtained by distillation.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | S(O)(O)(=O)=O | null | null | C=Cc1ccccc1.CC(C)c1ccccc1>S(O)(O)(=O)=O>CC(C)c1ccccc1C(C)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dd05b8f1b2c540f8a6f6e96280a71fb4 | CCCCN(CCCC)C(=O)c1cccc(OC(C)=O)c1>>CCCCN(CCCC)Cc1cccc(O)c1 | S(=O)(=O)([O-])[O-].[Mg+2].[OH-].[Na+].C(C)(=O)OC=1C=C(C(=O)N(CCCC)CCCC)C=CC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OC=1C=C(CN(CCCC)CCCC)C=CC1 | CC(=O)[O:16][c:15]1[cH:14][cH:13][cH:12][c:11]([C:10](=O)[N:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][CH2:8][CH3:9])[cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]1 | CCCCN(CCCC)C(=O)c1cccc(OC(C)=O)c1 | CCCCN(CCCC)Cc1cccc(O)c1 | null | null | O.CCOCC | Reduction | OtherReaction | 9abc997e012ed9d8d834b9a3f63bfe3454f23ced03bff048e83e49d30af1132c | 9f208a8b94e5538e117d755d0b06e07196757bf445f80a083aafb16ca1eb9d6a | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[C;H0;D3;+0:6](=O)-[#7:7](-[C:8])-[C:9]):[c:10]>>[C:8]-[#7:7](-[C:9])-[CH2;D2;+0:6]-[c:5](:[c:10]):[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | null | null | A mixture of 33.0 g (0.133 m) of 3-acetoxy-N,N-dibutylbenzamide in 400 ml of ether was slowly added over one half hour to a suspension of 5.0 (0.133 m) grams of lithium aluminum hydride (LAH) in 300 ml of ether. The mixture was heated to reflux for 2 hours. The mixture was slowly treated with 5.0 ml of water, 5.0 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Aromatic alcohol | null | null | c1ccccc1 | Other | O.CCOCC | null | null | CCCCN(CCCC)C(=O)c1cccc(OC(C)=O)c1>O.CCOCC>CCCCN(CCCC)Cc1cccc(O)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8a6119e32beb49ab984ec47353dcc123 | CCCCI.CCCCN(CCCC)Cc1cccc(O)c1>>CCCC[N+](CCCC)(CCCC)Cc1cccc(O)c1.[I-] | OC=1C=C(CN(CCCC)CCCC)C=CC1.C(CCC)I>>[I-].C(CCC)[N+](CCCC)(CCCC)CC1=CC(=CC=C1)O | [CH3:1][CH2:2][CH2:3][CH2:4][I:22].[N:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([OH:20])[cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N+:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([OH:20])[cH:21... | CCCCI.CCCCN(CCCC)Cc1cccc(O)c1 | CCCC[N+](CCCC)(CCCC)Cc1cccc(O)c1.[I-] | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | cf95568d208ea67162a1e8aa2ffc7c679479f5b8aaab2573599ff5258836e869 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccccc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[I;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[c:9])-[C:10]-[C:11]>>[C:5]-[C:6]-[N+;H0;D4:7](-[C:8]-[c:9])(-[C:10]-[C:11])-[CH2;D2;+0:3]-[C:2]-[C:1].[I-;H0;D0:4] | null | [] | null | null | null | null | A mixture was prepared containing 10 g (0.042 m) of 3-hydroxy N,N-dibutylbenzylamine, 15 g (0.082 m) of butyliodide and 25 ml of acetonitrile. The mixture was heated to reflux overnight. The completion of the reaction was determined by high pressure liquid chromatography. After completion, the solvent was removed and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | null | null | c1ccccc1 | null | C(C)#N | null | null | CCCCI.CCCCN(CCCC)Cc1cccc(O)c1>C(C)#N>CCCC[N+](CCCC)(CCCC)Cc1cccc(O)c1.[I-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0c0178a0dfca4667947a0499d672e7af | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1cc(Cl)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(N)cc(Cl)n1 | NC1=NC(=CC(=N1)N)Cl.C(=O)(OC)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>NC1=NC(=NC(=C1)Cl)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([NH2:21])[cH:22][c:23]([Cl:24])[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20]([NH2:21])[... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1cc(Cl)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(N)cc(Cl)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 4 | DAY | To a warmed mixture containing 1.4 g (0.01 mole) 2,4-diamino-6-chloropyrimidine in 50 ml acetonitrile is added 2.4 g (0.01 mole) 2-carbomethoxybenzenesulfonylisocyanate. The reaction mixture was stirred at room temperature for four days. The reaction mixture was filtered and the precipitate washed with ether. The filte... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(C)#N | null | 96 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1cc(Cl)nc(N)n1>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(N)cc(Cl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1aa257d84f0a42fc9e249dbfb9ff3317 | COC(=O)c1cccc([N+](=O)[O-])c1C.O=C1CCC(=O)N1Br>>COC(=O)c1cccc([N+](=O)[O-])c1CBr | ClCCCC.C1CCCCC1.CC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-].BrN1C(CCC1=O)=O.C(Cl)(Cl)(Cl)Cl>>BrCC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[CH3:14].O=C1CCC(=O)N1[Br:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[CH2:14][Br:15] | COC(=O)c1cccc([N+](=O)[O-])c1C.O=C1CCC(=O)N1Br | COC(=O)c1cccc([N+](=O)[O-])c1CBr | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | CCOCC | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:1]):[c:8] | 52.6 | [{"value": 52.6, "product": "BrCC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 100.0 g of methyl 2-methyl-3-nitrobenzoate, 100.0 g of N-bromosuccinimide, 3.0 g of dibenzoyl peroxide and 1000 ml of carbon tetrachloride was refluxed for 24 hours. The reaction mixture was cooled, 3.0 g of dibenzoyl peroxide added, and refluxing continued an additional 24 hours. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.CCOCC | null | 24 | COC(=O)c1cccc([N+](=O)[O-])c1C.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.CCOCC>COC(=O)c1cccc([N+](=O)[O-])c1CBr |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-16231784b9784304b58199bd7c4f5769 | COC(=O)c1cccc([N+](=O)[O-])c1CBr>>O=C1OCc2c1cccc2[N+](=O)[O-] | BrCC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-]>>[N+](=O)([O-])C1=CC=CC=2C(OCC21)=O | C[O:3][C:2](=[O:1])[c:6]1[c:5]([CH2:4]Br)[c:10]([N+:11](=[O:12])[O-:13])[cH:9][cH:8][cH:7]1>>[O:1]=[C:2]1[O:3][CH2:4][c:5]2[c:6]1[cH:7][cH:8][cH:9][c:10]2[N+:11](=[O:12])[O-:13] | COC(=O)c1cccc([N+](=O)[O-])c1CBr | O=C1OCc2c1cccc2[N+](=O)[O-] | null | null | O1CCOCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | aea24383edbe96de2d472a5cab034365c9438019ff5020199b3fcfad09fd8a38 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=C1OCc2ccccc21 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C>>[O;D1;H0:6]=[C:5]1-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-1 | 59.7 | [{"value": 59.7, "product": "[N+](=O)([O-])C1=CC=CC=2C(OCC21)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 54.8 g of methyl 2-bromomethyl-3-nitrobenzoate in a mixture of 200 ml dioxane and 45 ml water was refluxed for 72 hours. The reaction solution was cooled and concentrated in vacuo. The resulting solid was slurried in water, collected, washed with water and dried. Recrystallization from 1-chlorobutane gave... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | HBr | O1CCOCC1.O | null | null | COC(=O)c1cccc([N+](=O)[O-])c1CBr>O1CCOCC1.O>O=C1OCc2c1cccc2[N+](=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b9aaf99d87f6452baa0b885bec5e43ab | O=C1OCc2c1cccc2[N+](=O)[O-]>>O=[N+]([O-])c1cccc2c1COC2 | [N+](=O)([O-])C1=CC=CC=2C(OCC21)=O>>[N+](=O)([O-])C1=CC=CC=2COCC21 | O=[C:12]1[c:8]2[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:9]2[CH2:10][O:11]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][O:11][CH2:12]2 | O=C1OCc2c1cccc2[N+](=O)[O-] | O=[N+]([O-])c1cccc2c1COC2 | null | null | B(F)(F)F.CCOCC | Reduction | OtherReaction | fe61f926af1f03b39ab4264cfb4b79e476d6001758cdd7c373343d5ebadbb2b1 | 827848a04fae177f236c29c6caa2fc79931c8d66451736910cacf959ca644e0e | c1ccc2c(c1)COC2 | O=[C;H0;D3;+0:1]1-[#8:2]-[C:3]-[c:4]:[c:5]-1:[c:6]>>[c:6]:[c:5]1:[c:4]-[C:3]-[#8:2]-[CH2;D2;+0:1]-1 | 85.7 | [{"value": 85.7, "product": "[N+](=O)([O-])C1=CC=CC=2COCC21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 19.5 g of 1,3-dihydro-4-nitrobenzo[c]furan-1-one in 100 ml of boron trifluoride etherate was cooled to 0°-5° under nitrogen. 125 ml of a 1M solution of borane-tetrahydrofuran complex was added dropwise below 10°. The orange suspension was allowed to warm to ambient temperature (H2 evolution), and the re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ether | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | Other | B(F)(F)F.CCOCC | null | null | O=C1OCc2c1cccc2[N+](=O)[O-]>B(F)(F)F.CCOCC>O=[N+]([O-])c1cccc2c1COC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1648cd82d5bd4d05bf80b3d180ec237b | Cl.Nc1cccc2c1COC2.O=S=O>>O=S(=O)(Cl)c1cccc2c1COC2 | N(=O)[O-].[Na+].C1OCC2=C1C=CC=C2N.Cl.S(=O)=O.N(=O)[O-].[Na+].Cl>>C1OCC2=C1C=CC=C2S(=O)(=O)Cl | [ClH:4].N[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:11][O:12][CH2:13]2.[O:1]=[S:2]=[O:3]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:11][O:12][CH2:13]2 | Cl.Nc1cccc2c1COC2.O=S=O | O=S(=O)(Cl)c1cccc2c1COC2 | null | O.O.[Cu](Cl)Cl | O.C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 298b7523df104b16c2f933c319292577559cdcf41a184e06cb1ebbdbb03d5eca | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccc2c(c1)COC2 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6]-[#8:7].[ClH;D0;+0:8].[O;D1;H0:9]=[S;H0;D2;+0:10]=[O;D1;H0:11]>>[#8:7]-[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[S;H0;D4;+0:10](-[Cl;H0;D1;+0:8])(=[O;D1;H0:9])=[O;D1;H0:11]):[c:2]:[c:3] | null | [] | null | null | 1 | HOUR | A suspension of 22.1 g of the crude hydrochloride salt prepared in Example 2 in a mixture of 30 ml of concentrated hydrochloric acid and 30 ml acetic acid was cooled to 0°-5°. A solution of 6.2 g of sodium nitrite in 15 ml water was added dropwise at 0°-5°. The thick suspension was diluted with 19 ml of concentrated hy... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | Other | O.O.[Cu](Cl)Cl.O.C(C)(=O)O | null | 1 | Cl.Nc1cccc2c1COC2.O=S=O>O.O.[Cu](Cl)Cl.O.C(C)(=O)O>O=S(=O)(Cl)c1cccc2c1COC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1b8604044755497b8d713cda5a70a3fa | C1CCOC1.O=S(=O)(Cl)Cl.[NH4+].[OH-]>>NS(=O)(=O)c1cccc2c1COC2 | S(=O)(=O)(Cl)Cl.O1CCCC1.[OH-].[NH4+]>>C1OCC2=C1C=CC=C2S(=O)(=O)N | O1[CH2:5][CH2:8][CH2:9][CH2:10]1.Cl[S:2](Cl)(=[O:3])=[O:4].[NH4+:1].[OH-:12]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:11][O:12][CH2:13]2 | C1CCOC1.O=S(=O)(Cl)Cl.[NH4+].[OH-] | NS(=O)(=O)c1cccc2c1COC2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 977d8c666e412a53b664075ea73d0125eeefc2947eddbd1499ee7c191988d0bc | d239650332f2cf8d0af06622e2859ddb0cf4ecc1f38f84ddc5e28b00f2af42d8 | c1ccc2c(c1)COC2 | Cl-[S;H0;D4;+0:1](-Cl)(=[O;D1;H0:2])=[O;D1;H0:3].O1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1.[NH4+;D0:8].[OH-;D0:9]>>[NH2;D1;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:7]1:[c:10]:[c:11]:[cH;D2;+0:6]:[c;H0;D3;+0:5]2:[c;H0;D3;+0:4]:1-[C:12]-[O;H0;D2;+0:9]-[C:13]-2 | null | [] | null | null | 0.5 | HOUR | A solution of 9.8 g of the sulfonyl chloride, prepared in Part A, in 150 ml tetrahydrofuran was cooled to approximately 5°, and 6.6 ml of concentrated ammonium hydroxide was added dropwise. The resulting yellow suspension was allowed to warm to ambient temperature and stirred 0.5 hour; thin-layer chromatography showed ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Sulfonamide.Ether | C1CCOC1 | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | HCl | null | null | 0.5 | C1CCOC1.O=S(=O)(Cl)Cl.[NH4+].[OH-]>>NS(=O)(=O)c1cccc2c1COC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cc092392aa584ae0992038eb02f92cc7 | CCCCN=C=O.NS(=O)(=O)c1cccc2c1COC2>>O=C=NS(=O)(=O)c1cccc2c1COC2 | C(=O)(Cl)Cl.C1OCC2=C1C=CC=C2S(=O)(=O)N.C(CCC)N=C=O.C1CN2CCN1CC2.C(=O)(Cl)Cl>>C1OCC2=C1C=CC=C2S(=O)(=O)N=C=O | CCCCN=[C:2]=[O:1].[NH2:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][O:14][CH2:15]2>>[O:1]=[C:2]=[N:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][O:14][CH2:15]2 | CCCCN=C=O.NS(=O)(=O)c1cccc2c1COC2 | O=C=NS(=O)(=O)c1cccc2c1COC2 | null | null | C=1(C(=CC=CC1)C)C | Functional Group Interconversion | OtherReaction | d6c69f89b87c5c421a628563544ee2b8b0164ec4561bcd29a2cbba0dce4075ac | 5df9e857f75ada60baf9e936007533a18389016451154bd1ed26e91b5babd844 | c1ccc2c(c1)COC2 | C-C-C-C-N=[C;H0;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7] | null | [] | null | null | null | null | A mixture of 7.0 g of 1,3-dihydrobenzo[c]furan-4-sulfonamide, 4.0 ml of butyl isocyanate, 0.1 g of DABCO® and 150 ml xylene was heated to reflux. Phosgene (3.1 ml) was added in small portions to the reaction mixture while maintaining the reaction temperature <130°. When addition of phosgene was complete, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | null | null | null | c1ccc2c(c1)COC2 | Other | C=1(C(=CC=CC1)C)C | null | null | CCCCN=C=O.NS(=O)(=O)c1cccc2c1COC2>C=1(C(=CC=CC1)C)C>O=C=NS(=O)(=O)c1cccc2c1COC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9807506e1fd84e8989ff7c4a88a76aeb | CC(C)(C)S.COC(=O)c1cccc([N+](=O)[O-])c1CBr>>COC(=O)c1cccc([N+](=O)[O-])c1CSC(C)(C)C | BrCC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-].C[O-].[Na+].CC(C)(S)C>>CC(C)(SCC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-])C | [SH:15][C:16]([CH3:17])([CH3:18])[CH3:19].Br[CH2:14][c:13]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[CH2:14][S:15][C:16]([CH3:17])([CH3:18])[CH3:19] | CC(C)(C)S.COC(=O)c1cccc([N+](=O)[O-])c1CBr | COC(=O)c1cccc([N+](=O)[O-])c1CSC(C)(C)C | null | null | CO | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[SH;D1;+0:12]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:12]-[C:9](-[C;D1;H3:8])(-[C;D1;H3:10])-[C;D1;H3:11]):[c:3] | 92 | [{"value": 92.0, "product": "CC(C)(SCC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 34.7 g of sodium methoxide in 600 ml methanol was added 57.9 g of 1,1-dimethylethanethiol below 25°. The resulting solution was stirred one hour before the portionwise addition of 172.7 g of methyl 2-bromomethyl-3-nitrobenzoate. The resulting suspension was refluxed two hours. The mixture was cooled, a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1 | HBr | CO | null | null | CC(C)(C)S.COC(=O)c1cccc([N+](=O)[O-])c1CBr>CO>COC(=O)c1cccc([N+](=O)[O-])c1CSC(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-05a324f4402741408c24e634cccd45e7 | O=C1SCc2c1cccc2[N+](=O)[O-]>>Nc1cccc2c1CSC2=O | [N+](=O)([O-])C1=CC=CC=2C(SCC21)=O.Cl>>Cl.O=C1SCC2=C1C=CC=C2N | O=[N+:2]([O-])[c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH2:9][S:10][C:11]2=[O:12]>>[NH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH2:9][S:10][C:11]2=[O:12] | O=C1SCc2c1cccc2[N+](=O)[O-] | Nc1cccc2c1CSC2=O | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1SCc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 4-Nitrobenzo[c]thiophene-1(3H)-one (38.1 g) was added portionwise to a solution of 146.0 g of stannous chloride dihydrate in 325 ml concentrated hydrochloric acid. A slow exotherm from 18° to 42° occurred and the reaction mixture was maintained at 40°-45° by cooling. When the exotherm subsided, the suspension was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CSC2 | Other | null | null | null | O=C1SCc2c1cccc2[N+](=O)[O-]>>Nc1cccc2c1CSC2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5f3a1c1934ff44819208f12cf8073b61 | CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2=O>>CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2 | B(F)(F)F.CCOCC.CC(C)(C)NS(=O)(=O)C1=CC=CC=2C(SCC21)=O>>CC(C)(C)NS(=O)(=O)C1=CC=CC=2CSCC21 | O=[C:17]1[c:13]2[cH:12][cH:11][cH:10][c:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[c:14]2[CH2:15][S:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[CH2:15][S:16][CH2:17]2 | CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2=O | CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2 | null | null | O1CCCC1 | Reduction | OtherReaction | d43898b8eaf7ddd83b2ce67a1416e7f6a7945d083cd3daf5ffa5f056080cba6b | 2ca05ab8de5156f6c61f18ec42bac575d94b50ddbeffeb0dbed053d2d8fdb54d | c1ccc2c(c1)CSC2 | O=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[c:4]:[c:5]-1:[c:6]>>[c:6]:[c:5]1:[c:4]-[C:3]-[#16:2]-[CH2;D2;+0:1]-1 | 47.3 | [{"value": 47.3, "product": "CC(C)(C)NS(=O)(=O)C1=CC=CC=2CSCC21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A suspension of 8.0 g of 1,3-dihydro-N-(1,1-dimethylethyl)-1-oxobenzo[c]thiophene-4-sulfonamide in a mixture of 15 ml of tetrahydrofuran, 25 ml of boron trifluoride etherate was cooled to 10° under N2, and 56 ml of a 1M solution of borane tetrahydrofuran complex was added dropwise at approximately 10°. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Monosulfide | c1ccc2c(c1)CSC2 | c1ccc2c(c1)CSC2 | c1ccc2c(c1)CSC2 | Other | O1CCCC1 | null | 8 | CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2=O>O1CCCC1>CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c00937995bdd4e3994a23e4c6555f433 | CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2>>NS(=O)(=O)c1cccc2c1CSC2 | CC(C)(C)NS(=O)(=O)C1=CC=CC=2CSCC21>>C1SCC2=C1C=CC=C2S(=O)(=O)N | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:11][S:12][CH2:13]2>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[CH2:11][S:12][CH2:13]2 | CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2 | NS(=O)(=O)c1cccc2c1CSC2 | null | null | CCCCCC.C(C)(=O)OCC.FC(C(=O)O)(F)F | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1ccc2c(c1)CSC2 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 58.8 | [{"value": 58.8, "product": "C1SCC2=C1C=CC=C2S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3.0 g of 1,3-dihydro-N-(1,1-dimethylethyl)benzo[c]thiophene-4-sulfonamide in 50 ml of trifluoroacetic acid was stirred at ambient temperature for 4 hours. The brown solution was concentrated in vacuo. 1-Chlorobutane was added to the resulting brown oil and the mixture concentrated in vacuo. Repeating this... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccc2c(c1)CSC2 | Other | CCCCCC.C(C)(=O)OCC.FC(C(=O)O)(F)F | null | null | CC(C)(C)NS(=O)(=O)c1cccc2c1CSC2>CCCCCC.C(C)(=O)OCC.FC(C(=O)O)(F)F>NS(=O)(=O)c1cccc2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e1893475f31044b7b7638714ac2306e2 | CCCCN=C=O.NS(=O)(=O)c1cccc2c1CSC2>>O=C=NS(=O)(=O)c1cccc2c1CSC2 | C(=O)(Cl)Cl.C1SCC2=C1C=CC=C2S(=O)(=O)N.C(CCC)N=C=O.C1CN2CCN1CC2.C(=O)(Cl)Cl>>C1SCC2=C1C=CC=C2S(=O)(=O)N=C=O | CCCCN=[C:2]=[O:1].[NH2:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][S:14][CH2:15]2>>[O:1]=[C:2]=[N:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][S:14][CH2:15]2 | CCCCN=C=O.NS(=O)(=O)c1cccc2c1CSC2 | O=C=NS(=O)(=O)c1cccc2c1CSC2 | null | null | C=1(C(=CC=CC1)C)C | Functional Group Interconversion | OtherReaction | d6c69f89b87c5c421a628563544ee2b8b0164ec4561bcd29a2cbba0dce4075ac | 5df9e857f75ada60baf9e936007533a18389016451154bd1ed26e91b5babd844 | c1ccc2c(c1)CSC2 | C-C-C-C-N=[C;H0;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7] | null | [] | null | null | 5 | MINUTE | A mixture of 5.5 g of 1,3-dihydrobenzo[c]thiophene-4-sulfonamide, 2.5 g of butyl isocyanate and 0.05 g of DABCO® in 50 ml of xylene was heated to 135° and 2.2 ml of liquid phosgene was added in small portions at approximately 135°. When the addition of phosgene was complete, heating was continued for 5 minutes before t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Isocyanate | null | null | null | c1ccc2c(c1)CSC2 | Other | C=1(C(=CC=CC1)C)C | null | 0.083333 | CCCCN=C=O.NS(=O)(=O)c1cccc2c1CSC2>C=1(C(=CC=CC1)C)C>O=C=NS(=O)(=O)c1cccc2c1CSC2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-063544486b52402f879594b5f17cda45 | COC(=O)Nc1nc(OC)cc(OC)n1.NS(=O)(=O)c1cccc2c1CS(=O)(=O)C2>>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2cccc3c2CSC3)n1 | COC1=NC(=NC(=C1)OC)NC(OC)=O.C[Al](C)C.C1S(CC2=C1C=CC=C2S(=O)(=O)N)(=O)=O.Cl>>COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=CC=CC=2CSCC21 | CO[C:11]([NH:10][c:9]1[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:26]1)=[O:12].O=[S:24]1(=O)[CH2:23][c:22]2[c:17]([S:14]([NH2:13])(=[O:15])=[O:16])[cH:18][cH:19][cH:20][c:21]2[CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:1... | COC(=O)Nc1nc(OC)cc(OC)n1.NS(=O)(=O)c1cccc2c1CS(=O)(=O)C2 | COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2cccc3c2CSC3)n1 | null | null | C1(=CC=CC=C1)C.C(Cl)Cl | Acylation | OtherReaction | 48c18f6ef5bb69256637d7ec4e1277e7b1fb85955944d5b1024807a279058c13 | 9cf7fb13481173a489ce6c8f5303d937443bb3154e5e0bf1c0e0faf659542570 | O=C(Nc1ncccn1)NS(=O)(=O)c1cccc2c1CSC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4](:[#7;a:5]):[#7;a:6].O=[S;H0;D4;+0:7]1(=O)-[C:8]-[c:9](:[c:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]):[c:15]-[C:16]-1>>[#7;a:5]:[c:4](-[#7:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[#16:11](=[O;D1;H0:13])(=[O;D1;H0:14])-[c:10]:[c:9]1:[c:15]-[C:16]-[S;H0;D... | 26.1 | [{"value": 26.1, "product": "COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=CC=CC=2CSCC21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 0.74 g of the sulfonamide prepared in Example 13 in 50 ml of methylene chloride was cooled to 10° to 15° under nitrogen, and 1.7 ml of a 2M solution of trimethylaluminum in toluene was added slowly. The suspension was allowed to warm to room temperature, 0.67 g of methyl N-(4,6-dimethoxypyrimidin-2-yl)c... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carbamic ester.Ether.Sulfone | Sulfonamide.Urea.Monosulfide | c1ccc2c(c1)CSC2 | c1ccc2c(c1)CSC2 | c1cncnc1.c1ccc2c(c1)CSC2 | HO- | C1(=CC=CC=C1)C.C(Cl)Cl | null | null | COC(=O)Nc1nc(OC)cc(OC)n1.NS(=O)(=O)c1cccc2c1CS(=O)(=O)C2>C1(=CC=CC=C1)C.C(Cl)Cl>COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2cccc3c2CSC3)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-249b94811ba9490698afb75a6c5f7e0e | CN1Cc2cccc(S(=O)(=O)NC(C)(C)C)c2C1>>CN1Cc2cccc(S(N)(=O)=O)c2C1 | CC(C)(C)NS(=O)(=O)C=1C=2CN(CC2C=CC1)C.B.Cl>>Cl.CN1CC=2C=CC=C(C2C1)S(=O)(=O)N | CC(C)(C)[NH:10][S:9]([c:8]1[cH:7][cH:6][cH:5][c:4]2[c:13]1[CH2:14][N:2]([CH3:1])[CH2:3]2)(=[O:11])=[O:12]>>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:7][c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[c:13]2[CH2:14]1 | CN1Cc2cccc(S(=O)(=O)NC(C)(C)C)c2C1 | CN1Cc2cccc(S(N)(=O)=O)c2C1 | null | null | CO | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | c1ccc2c(c1)CNC2 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | A suspension of 5.3 g of the compound prepared in Example 16 in 20 ml of methanol was cooled to 10° and 50 ml of concentrated hydrochloric acid was added dropwise at 10°-15° (gas evolution). The reaction mixture was allowed to warm to room temperature and then refluxed 3.75 hours. The reaction solution was cooled and c... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccc2c(c1)C[NH]C2 | Other | CO | null | null | CN1Cc2cccc(S(=O)(=O)NC(C)(C)C)c2C1>CO>CN1Cc2cccc(S(N)(=O)=O)c2C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a50d1f052edd4cf8a047bd5fea03700d | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(C)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 | NC1=NC(=CC(=N1)C)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>CC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([CH3:21])[cH:22][c:23]([CH3:24])[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20]([CH3:21])... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(C)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | To 37 g. of 2-amino-4,6-dimethylpyrimidine in 500 ml of anhydrous acetonitrile was added 67 g of 2-methoxycarbonylbenzenesulfonylisocyanate with stirring at ambient temperatures. The resulting mixture was thereafter stirred for sixteen hours and then filtered to remove the desired product which had precipitated as a wh... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(C)#N | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(C)nc(N)n1>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6ac58de6463b4514a146dc2fe7fd0150 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1ncccn1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1ncccn1 | NC1=NC=CC=N1.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>N1=C(N=CC=C1)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][cH:20][cH:21][cH:22][n:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][cH:20][cH:21][cH:22][n:23]1 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1ncccn1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1ncccn1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | With stirring at ambient temperature, 1.0 g of 2-aminopyrimidine in 25 ml of anhydrous acetonitrile was added to 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring that mixture for 24 hours, the resultant precipitate was filtered off to yield 2.2 of the desired compound which melted at 188°-192°. Its s... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(C)#N | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1ncccn1>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1ncccn1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d7657689bdfa4d728e9fe502d770f8f4 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(C)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | NC1=NC(=CC(=N1)OC)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([CH3:21])[cH:22][c:23]([O:24][CH3:25])[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20]([CH... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(C)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 16 | HOUR | To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrous methylene chloride was added at ambient temperature 2.4 of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring for 16 hours, the foregoing mixture was filtered to remove unreacted amine, and the filtrate evaporated at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(Cl)Cl | null | 16 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(C)nc(N)n1>C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-29ddd2f7388744f782d178475a0763ad | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(OC)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 | [OH-].[Na+].NC1=NC(=CC(=N1)OC)OC.C(Cl)Cl.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([O:21][CH3:22])[cH:23][c:24]([O:25][CH3:26])[n:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:2... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(OC)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 | null | null | O | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | 43.1 | [{"value": 43.1, "product": "COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture containing 1.6 g of 2-amino-4,6-dimethoxypyrimidine, 30 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate was stirred at ambient temperature and pressure for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | O | null | 16 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(OC)nc(N)n1>O>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5c979161a8de4610822a99c0859d08c6 | COc1nc(N)nc(OC)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)nc(OC)n1 | NC1=NC(=NC(=N1)OC)OC.ClCCOC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OCCCl | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:25][c:26]([O:27][CH3:28])[n:29]1.[C:7](=[O:8])=[N:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19](=[O:20])[O:21][CH2:22][CH2:23][Cl:24]>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][C:7](=[O:8])[NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:... | COc1nc(N)nc(OC)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl | COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | null | null | To 0.7 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(β-chloroethoxycarbonyl)benzenesulfonyl isocyanate. After stirring at ambient temperature for sixteen hours the solvent was removed under reduced pressure, the residue triturated with ether and the solid pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1nc(N)nc(OC)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>C(Cl)Cl>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7328358f9f674acfa9a4e50d2e72f16b | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)n1 | NC1=NC(=NC(=N1)OC)C.ClCCOC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OCCCl | [CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:28]1.[C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22](=[O:23])[O:24][CH2:25][CH2:26][Cl:27]>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][... | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | 80.1 | [{"value": 80.1, "product": "COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 0.7 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(β-chloroethoxycarbonyl)benzenesulfonyl isocyanate with stirring at ambient temperature. The mixture was thereafter stirred for sixteen hours. The solvent was evaporated under reduced pressure and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>C(Cl)Cl>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-379f1a67d29d44b48e396b3ea3fe3528 | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)nc(OC)n1 | NC1=NC(=NC(=N1)OC)OC.C(C)(C)OC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C | [C:7](=[O:8])=[N:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19](=[O:20])[O:21][CH:22]([CH3:23])[CH3:24].[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:25][c:26]([O:27][CH3:28])[n:29]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][C:7](=[O:8])[NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][... | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1 | COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | 26.2 | [{"value": 26.2, "product": "COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 0.7 g of 2-amino-4,6-dimethoxy-1,3,5-triazine suspended in 5.0 ml anhydrous methylene chloride was added 1.6 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 5.0 ml anhydrous methylene chloride. The resulting mixture was filtered to remove some unreacted 2-amino-4,6-dimethoxytriazine, the methylene chloride fi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>C(Cl)Cl>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3e64374bceef4d3e98affc0f14b126ad | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 | NC1=NC(=NC(=N1)OC)C.C(C)(C)OC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C | [C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22](=[O:23])[O:24][CH:25]([CH3:26])[CH3:27].[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:28]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18... | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1 | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | 51.1 | [{"value": 51.1, "product": "COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 26.8 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 300 ml anhydrous methylene chloride was added 67.0 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 100 ml anhydrous methylene chloride. The resultant suspension was stirred at ambient temperature for 72 hours, and filtered to yield 40.0 g of the desired p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>C(Cl)Cl>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1a42b4a852c246918fc407ff080bfbe6 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | NC1=NC(=NC(=N1)OC)OC.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([O:21][CH3:22])[n:23][c:24]([O:25][CH3:26])[n:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | 16 | HOUR | A mixture of 1.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine, 25 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate was stirred at ambient temperature for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40° under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1ncncn1 | null | C(Cl)Cl | null | 16 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-17f4e25cab9e495396ead1253b029761 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | NC1=NC(=NC(=N1)OC)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([CH3:21])[n:22][c:23]([O:24][CH3:25])[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20]([CH3... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | null | null | To an anhydrous suspension of 1.4 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 25 ml of methylene chloride was added with stirring at ambient temperature and pressure 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was thereafter stirred for 16 hours and filtered. The filtrate was evaporated to dr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1ncncn1 | null | C(Cl)Cl | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-df9242c3024e438a932c728f85902814 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1nnc(N)nc1C>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nnc(C)c(C)n1 | NC=1N=NC(=C(N1)C)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>CC=1N=C(N=NC1C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][n:20][c:21]([CH3:22])[c:23]([CH3:24])[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][n:20][c:21]([CH3... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1nnc(N)nc1C | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nnc(C)c(C)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1nccnn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1 | 70.8 | [{"value": 70.8, "product": "CC=1N=C(N=NC1C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a stirred suspension of 1.2 g of 3-amino-5,6-dimethyl-1,2,4-triazine in 25 ml of anhydrous acetonitrile was added at ambient temperature 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring for 24 hours at ambient temperature, the resultant precipitate was filtered off to yield 2.5 g of the desired co... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cnncn1 | null | C(C)#N | null | 24 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1nnc(N)nc1C>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nnc(C)c(C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3896c410ab374976982939d1b785eef7 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(N)nc(C)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1cc(C)nc(C)n1 | NC1=NC(=NC(=C1)C)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>CC1=NC(=CC(=N1)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[cH:19][c:20]([CH3:21])[n:22][c:23]([CH3:24])[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[cH:19][c:20]([CH3:21]... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(N)nc(C)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1cc(C)nc(C)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ccncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | null | null | To a suspension of 1.2 g of 4-amino-2,6-dimethylpyrimidine in 30 ml of dry acetonitrile with stirring was added 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was stirred for two hours at ambient temperature, allowed to stand for sixteen hours and the desired product, which had precipitated, was remov... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(C)#N | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(N)nc(C)n1>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1cc(C)nc(C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-78754e277bf64816b19f44ca82c06a8b | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1>>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | CC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.[OH-].[Na+]>>CC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)O | C[O:23][C:21]([c:20]1[c:15]([S:12]([NH:11][C:9]([NH:8][c:7]2[n:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[n:24]2)=[O:10])(=[O:13])=[O:14])[cH:16][cH:17][cH:18][cH:19]1)=[O:22]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9](=[O:10])[NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21](=[O:2... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 | Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A mixture of 2.0 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and 11 ml. of 50% aqueous sodium hydroxide was warmed on a steam bath with shaking; 40 ml. of water was added and heating and shaking continued during the next half hour. The resulting solution was then filtered and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | O | null | null | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1>O>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b579e7d807ce471091ae61696148e0d8 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1>>COc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.[OH-].[K+].Cl>>COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)O | C[O:24][C:22]([c:21]1[c:16]([S:13]([NH:12][C:10]([NH:9][c:8]2[n:7][c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[n:25]2)=[O:11])(=[O:14])=[O:15])[cH:17][cH:18][cH:19][cH:20]1)=[O:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | COc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | null | null | O.C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 24 | HOUR | 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide was dissolved in a mixture of 20 ml of absolute ethanol, 2.5 ml of water and 2.5 g of potassium hydroxide. After stirring at 25° for 24 hours the mixture had become a semi-solid mass. Enough cold water was added to dissolve... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | O.C(C)O | null | 24 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1>O.C(C)O>COc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4436e129eaef4387a197daa3a9056f9a | CCOC(=O)C(C)Oc1nc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC(C)C(=O)O)n1 | S(=O)(=O)(N=C=O)N=C=O.Cl.N(=C=O)S(=O)(=O)C1=C(C(=O)OC)C=CC=C1.NC1=NC(=NC(=N1)C)OC(C(=O)OCC)C.[OH-].[Na+].S(=O)(=O)(N=C=O)N=C=O>>C(=O)(O)C(C)OC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1 | CC[O:29][C:27]([CH:25]([O:24][c:23]1[n:22][c:20]([CH3:21])[n:19][c:18]([NH2:17])[n:30]1)[CH3:26])=[O:28].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16]... | CCOC(=O)C(C)Oc1nc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC(C)C(=O)O)n1 | null | null | O.C(Cl)Cl | Acylation | OtherReaction | 873ec03fe95613b89e1cc5a05f22b73e12ebaee68f679a7c1a383abbdb2c243b | 5dcf854e8ae1ebe2ca3cab743b2d9636aaa3c8192f5216ab3e9c6da3c3a8eaed | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:1.[O;D1;H0:12]=[#16:13](=[O;D1;H0:14])(-[c:15])-[N;H0;D2;+0:16]=[C;H0;D2;+0:17]=[O;D1;H0:18]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:12]=[#16:13](=[O;D1;H0:14])(-[c:15])-[NH;D2;+0:16]-[C;H0;D3;+0:17](=[O;... | 23.8 | [{"value": 23.8, "product": "C(=O)(O)C(C)OC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 2-(isocyanatosulfonyl)benzoate (10.1 g) and 8.0 g of ethyl 2-[(4-amino-6-methyl-1,3,5-triazin-2-yl)oxy]propanoate were stirred in 80 ml of methylene chloride at ambient temperature for 18 hours. An additional 2 g of the sulfonylisocyanate was added and the reaction mixture was stirred for four more hours and the... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Sulfonamide.Carboxylic acid.Urea | null | null | c1ccccc1.c1ncncn1 | Other | O.C(Cl)Cl | null | null | CCOC(=O)C(C)Oc1nc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O>O.C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC(C)C(=O)O)n1 |
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