dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-199fcedcf8044722923baaa5b14e12bf | C#CC(=O)OC(C)(C)C.CCOC(=O)C(N)=NO>>CCOC(=O)c1nc(C(=O)OC(C)(C)C)c[nH]1 | C(C#C)(=O)OC(C)(C)C.NC(C(=O)OCC)=NO.C=1(C(=CC=CC1)C)C>>C(C)OC(=O)C=1NC=C(N1)C(=O)OC(C)(C)C | [C:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])#[CH:16].O[N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH2:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][nH:17]1 | C#CC(=O)OC(C)(C)C.CCOC(=O)C(N)=NO | CCOC(=O)c1nc(C(=O)OC(C)(C)C)c[nH]1 | null | null | C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | 1a8eddfecd0917248b2f4bc96ba85ccddcb260b77275366dca5d8d7aae3edf0b | 76dbfeda98b19c1e1248a8fac66bc22be17ead6952c98f11b2e36ab4bdbeafa6 | c1c[nH]cn1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[NH2;D1;+0:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[C;H0;D2;+0:15]#[CH;D1;+0:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:2]1:[n;H0;D2;+0:1]:[c;H0;D3;+0:15](-[C:13](=[O;D1;H0:14])-[#8:12]-[C:9](-[C;D1;H3:8])... | null | [] | null | null | null | null | tert-Butyl 2-ethoxycarbonyl imidazole-4-carboxylate can be prepared as follows: the procedure is as in Example 1 but starting from 15 g of ethyl α-aminooximinoacetate, 500 ml of xylene, 19.1 of triethylamine and 14.3 ml of tert-butyl propiolate. The crude product (19 g) is chromatographed on a silica column, eluting wi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine.Alkyne.Oxime | Ester.Ester | null | c1c[nH]cn1 | c1c[nH]cn1 | HO- | C(C)N(CC)CC | null | null | C#CC(=O)OC(C)(C)C.CCOC(=O)C(N)=NO>C(C)N(CC)CC>CCOC(=O)c1nc(C(=O)OC(C)(C)C)c[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71deb639e501406b8994cac9a143516e | CC(C)CCON=O.CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3>>O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3=NO | O.[H-].[Na+].O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3)C=C(N2)C(=O)OCC.N(=O)OCCC(C)C>>ON=C1C=2C=CC=CC2C=2NC(C=3N(C21)C=C(N3)C(=O)O)=O | CC(C)CCO[N:21]=[O:22].CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6]2[c:7]3[c:8]([nH:9][c:10](=[O:11])[c:12]2[n:13]1)-[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[CH2:20]3>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]2[c:7]3[c:8]([nH:9][c:10](=[O:11])[c:12]2[n:13]1)-[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[C:20]3=[N:21][OH:22] | CC(C)CCON=O.CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3 | O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3=NO | null | null | C(C)(=O)O.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 58239249e615ec552798952b225c21cfaf0b2545ba18fba7dbc485e32ed12672 | 76a27e58b662a405c95e29e5fb6fdbef5dc765e93c458d81e56749745ac9d49d | N=C1c2ccccc2-c2[nH]c(=O)c3nccn3c21 | C-C(-C)-C-C-O-[N;H0;D2;+0:1]=[O;H0;D1;+0:2].C-C-[O;H0;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[#7;a:7]:[c:8]2:[c:9]:[#7;a:10]:[c:11]3:[c:12](:[#7;a:13]:2:[c:14]:1)-[CH2;D2;+0:15]-[c:16](:[c:17]):[c:18]-3>>[O;D1;H0:5]=[C:4](-[OH;D1;+0:3])-[c:6]1:[#7;a:7]:[c:8]2:[c:9]:[#7;a:10]:[c:11]3:[c:12](:[#7;a:13]:2:[c:14]:1)-[C;H0;D3;... | null | [] | null | null | 18 | HOUR | 0.34 g of sodium hydride is added to 1 g of ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in solution in 20 ml of anhydrous dimethyl sulphoxide, while the temperature of the reaction mixture is maintained below 20° C. 0.44 ml of isoamyl nitrite is then added and stirring is continued for... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitroso | Carboxylic acid.Oxime | c1cn2c3c(ncc2n1)c1ccccc1C3 | C1c2ccccc2c2ncc3nccn3c21 | C1c2ccccc2c2ncc3nccn3c21 | HO- | C(C)(=O)O.CS(=O)C | null | 18 | CC(C)CCON=O.CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3>C(C)(=O)O.CS(=O)C>O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3=NO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2183c14e46bb4ed985660d3128597a1a | CCn1c2c(n3c(Cl)c(C(=O)[O-])nc3c1=O)Cc1ccccc1-2.Cl>>O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1cc(Cl)ccc1C3 | C(C)N1C(C=2N(C3=C1C=1C=CC=CC1C3)C(=C(N2)C(=O)[O-])Cl)=O.Cl>>ClC=1C=CC=2CC3=C(NC(C=4N3C=C(N4)C(=O)O)=O)C2C1 | CC[n:9]1[c:8]2[c:7]([n:6]3[c:5](Cl)[c:4]([C:2](=[O:1])[O-:3])[n:13][c:12]3[c:10]1=[O:11])[CH2:21][c:20]1[c:14]-2[cH:15][cH:16][cH:18][cH:19]1.[ClH:17]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]2[c:7]3[c:8]([nH:9][c:10](=[O:11])[c:12]2[n:13]1)-[c:14]1[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]1[CH2:21]3 | CCn1c2c(n3c(Cl)c(C(=O)[O-])nc3c1=O)Cc1ccccc1-2.Cl | O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1cc(Cl)ccc1C3 | null | null | null | Miscellaneous | OtherReaction | 706a38f8d4c69a067eb32b6ad403e7ad392592acd7a7a81f0af6c1b942975906 | 955a001693f5f4b49fc4e2fdd67dfb091f2752f79e87ea36f0c95ba0e1c73fad | O=c1[nH]c2c(n3ccnc13)Cc1ccccc1-2 | C-C-[n;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[c:4]2:[#7;a:5]:[c:6](-[C:7](-[O-;H0;D1:8])=[O;D1;H0:9]):[c;H0;D3;+0:10](-Cl):[#7;a:11]:2:[c:12](:[c:13]:1-[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[c:18])-[C:19].[ClH;D0;+0:20]>>[C:19]-[c:12]1:[#7;a:11]2:[cH;D2;+0:10]:[c:6](-[C:7](=[O;D1;H0:9])-[OH;D1;+0:8]):[#7;a:5]:[c:4]:2:[c:2](=[O... | null | [] | null | null | null | null | 0.58 g of ethyl-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in suspension in 10 ml of 6N hydrochloric acid is heated to reflux for 24 hours. After cooling to a temperature close to 20° C., the insoluble matter is filtered off, washed with water and dried under reduced pressure (1 mm H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide.Carboxylic acid | c1ccc2c(c1)Cc1c2ncc2nccn12 | c1ccc2c(c1)c1ncc3nccn3c1C2 | c1ccc2c(c1)c1ncc3nccn3c1C2 | HCl | null | null | null | CCn1c2c(n3c(Cl)c(C(=O)[O-])nc3c1=O)Cc1ccccc1-2.Cl>>O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1cc(Cl)ccc1C3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c6c6d89b5d34913acc93848722ce98e | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3.[OH-]>>O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3=O | [OH-].[Na+].O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3)C=C(N2)C(=O)OCC>>O=C1C=2N(C3=C(N1)C=1C=CC=CC1C3=O)C=C(N2)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6]2[c:7]3[c:8]([nH:9][c:10](=[O:11])[c:12]2[n:13]1)-[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[CH2:20]3.[OH-:21]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]2[c:7]3[c:8]([nH:9][c:10](=[O:11])[c:12]2[n:13]1)-[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[C:20]3=[O:21] | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3.[OH-] | O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3=O | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6d3703b8db8a90dadf0e806464da31576a6986d3b067935416ad073a4d22d574 | 89fece21d142fe5b25c7ee726efca0f4579a0f2dfb61f1727c636b2f861559cc | O=C1c2ccccc2-c2[nH]c(=O)c3nccn3c21 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]2:[c:7]:[#7;a:8]:[c:9]3:[c:10](:[#7;a:11]:2:[c:12]:1)-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]-3.[OH-;D0:17]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[#7;a:5]:[c:6]2:[c:7]:[#7;a:8]:[c:9]3:[c:10](:[#7;a:11]:2:[c:12]:1)-[C;H0;D3;+0:13](=[O;H0;D1;+0:17])-[c:14](:[c:... | null | [] | null | null | null | null | 5 ml of 1N sodium hydroxide are added to a suspension of 0.2 g of ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in 15 ml of dioxane, and the reaction mixture is stirred vigorously while compressed air is bubbled for 15 hours. After addition of 10 ml of distilled water the mixture is acid... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid.Ketone | c1cn2c3c(ncc2n1)c1ccccc1C3 | C1c2ccccc2c2ncc3nccn3c21 | C1c2ccccc2c2ncc3nccn3c21 | Other | O1CCOCC1 | null | null | CCOC(=O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3.[OH-]>O1CCOCC1>O=C(O)c1cn2c3c([nH]c(=O)c2n1)-c1ccccc1C3=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b57a278ca83a40158214026646782b72 | O=C1CCCc2ccc(OCc3ccncc3)cc21>>OC1CCCc2ccc(OCc3ccncc3)cc21 | N1=CC=C(C=C1)COC1=CC=C2CCCC(C2=C1)=O.[H-].C(C(C)C)[Al+]CC(C)C>>N1=CC=C(C=C1)COC1=CC=C2CCCC(C2=C1)O | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][n:15][cH:16][cH:17]3)[cH:18][c:19]21>>[OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][n:15][cH:16][cH:17]3)[cH:18][c:19]21 | O=C1CCCc2ccc(OCc3ccncc3)cc21 | OC1CCCc2ccc(OCc3ccncc3)cc21 | null | null | C1(=CC=CC=C1)C.O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1cc(COc2ccc3c(c2)CCCC3)ccn1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | 78.2 | [{"value": 78.2, "product": "N1=CC=C(C=C1)COC1=CC=C2CCCC(C2=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of Compound 1 (16.41 g, 64.9 mmol) in tetrahydrofuran (75 mL) at 0° C. was added dropwise a 1M solution of diisobutylaluminum hydride in toluene (97.3 mL). After 1 hr, the reaction was quenched with aqueous potassium sodium tartrate and diluted with ethyl acetate followed by warming to room temperature. A... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccncc1 | null | C1(=CC=CC=C1)C.O1CCCC1 | null | 1 | O=C1CCCc2ccc(OCc3ccncc3)cc21>C1(=CC=CC=C1)C.O1CCCC1>OC1CCCc2ccc(OCc3ccncc3)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e88b3e62b23f461dad90710584c27c0b | NCc1ccccc1.O=C1CCCc2ccc(OCc3ccncc3)cc21>>c1ccc(CNC2CCCc3ccc(OCc4ccncc4)cc32)cc1 | N1=CC=C(C=C1)COC1=CC=C2CCCC(C2=C1)=O.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC1CCCC2=CC=C(C=C12)OCC1=CC=NC=C1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:25][cH:26]1.O=[C:7]1[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][n:20][cH:21][cH:22]3)[cH:23][c:24]21>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH:7]2[CH2:8][CH2:9][CH2:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[cH:18][cH:19][n... | NCc1ccccc1.O=C1CCCc2ccc(OCc3ccncc3)cc21 | c1ccc(CNC2CCCc3ccc(OCc4ccncc4)cc32)cc1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 29755ba5f0cb4006bce04ebfcf05343f0b76e87f1bf151eb9789d383875ad425 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CNC2CCCc3ccc(OCc4ccncc4)cc32)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[C:3]-[C:2]-[CH;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9])-[c:4](:[c:5]):[c:6] | 97.7 | [{"value": 97.7, "product": "C(C1=CC=CC=C1)NC1CCCC2=CC=C(C=C12)OCC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 30 | MINUTE | A solution of Compound 1 (820 mg, 3.24 mmol) and benzyl amine (354 μL, 3.24 mmol) in benzene (10 mL) was heated to reflux under azeotropic conditions. After the calculated amount of water was collected, the reaction was cooled and concentrated in vacuo. The residue was taken-up into ethanol (5 mL) and added to a slurry... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccncc1 | Other | C1=CC=CC=C1 | 80 | 0.5 | NCc1ccccc1.O=C1CCCc2ccc(OCc3ccncc3)cc21>C1=CC=CC=C1>c1ccc(CNC2CCCc3ccc(OCc4ccncc4)cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-10ff625fe5984e5b87fd676cfad5e889 | CCCOc1cc2c(c(OCCC)c1C)CCC(=Cc1cccnc1)C2=O>>CCCOc1cc2c(c(OCCC)c1C)CCC(Cc1cccnc1)C2=O | CC=1C(=C2CCC(C(C2=CC1OCCC)=O)=CC=1C=NC=CC1)OCCC.[H][H]>>CC=1C(=C2CCC(C(C2=CC1OCCC)=O)CC=1C=NC=CC1)OCCC | [CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7]2[c:8]([c:9]([O:10][CH2:11][CH2:12][CH3:13])[c:14]1[CH3:15])[CH2:16][CH2:17][C:18](=[CH:19][c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1)[C:26]2=[O:27]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7]2[c:8]([c:9]([O:10][CH2:11][CH2:12][CH3:13])[c:14]1[CH3:15])[CH2:16][CH2:17][CH:18](... | CCCOc1cc2c(c(OCCC)c1C)CCC(=Cc1cccnc1)C2=O | CCCOc1cc2c(c(OCCC)c1C)CCC(Cc1cccnc1)C2=O | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | ef5776194d0a56b0d0bcb4f3f44edabcb716b463d0f1a539f552dbead062784c | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1c2ccccc2CCC1Cc1cccnc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9])-[C:10](=[O;D1;H0:11])-[c:12]>>[C:1]-[C:2]-[CH;D3;+0:3](-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9])-[C:10](=[O;D1;H0:11])-[c:12] | 68.5 | [{"value": 68.5, "product": "CC=1C(=C2CCC(C(C2=CC1OCCC)=O)CC=1C=NC=CC1)OCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of Compound 25 (3.96 g, 10.8 mmol) and 10% palladium on carbon (600 mg) in abs. methanol (100 mL) was hydrogenated at 1 atm for 12 hr. The hydrogen was replaced with nitrogen, the reaction was filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with 20% ethyl acetate:hexan... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccncc1 | null | [Pd].CO | null | null | CCCOc1cc2c(c(OCCC)c1C)CCC(=Cc1cccnc1)C2=O>[Pd].CO>CCCOc1cc2c(c(OCCC)c1C)CCC(Cc1cccnc1)C2=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3e15f22347a94a73bb5a31fc83b5b69f | CCOC(=O)[C@@H]1CCCNC1.N>>NC(=O)[C@@H]1CCCNC1 | N1C[C@H](C(=O)OCC)CCC1.N>>N1C[C@H](C(=O)N)CCC1 | CCO[C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8][CH2:9]1.[NH3:1]>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8][CH2:9]1 | CCOC(=O)[C@@H]1CCCNC1.N | NC(=O)[C@@H]1CCCNC1 | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[#7:6].[NH3;D0;+0:7]>>[#7:6]-[C:5]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:7])=[O;D1;H0:2])-[C:4] | null | [] | null | null | 3 | DAY | To 14.7 g (93.5 mmol) of (R)-ethyl nipecotate in a 300 ml round-bottomed flask were added 200 ml of concentrated aqueous ammonia at room temperature, and the mixture was allowed to stand for 3 days at room temperature. The reaction mixture was distilled off at a water bath temperature of lower than 40° C. to obtain (R)... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CCNCC1 | HO- | null | null | 72 | CCOC(=O)[C@@H]1CCCNC1.N>>NC(=O)[C@@H]1CCCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-44351331f59d49308273d55a1a4782d5 | COCC(=O)Cl.N[C@@H]1CCCN(Cc2ccccc2)C1>>COCC(=O)N[C@@H]1CCCN(Cc2ccccc2)C1 | O1CCCC1.COCC(=O)Cl.O1CCCC1.C1(=CC=CC=C1)CN1C[C@@H](CCC1)N.O1CCCC1.C(C)N(CC)CC>>COCC(=O)N[C@H]1CN(CCC1)CC1=CC=CC=C1 | Cl[C:4]([CH2:3][O:2][CH3:1])=[O:5].[NH2:6][C@@H:7]1[CH2:8][CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[NH:6][C@@H:7]1[CH2:8][CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1 | COCC(=O)Cl.N[C@@H]1CCCN(Cc2ccccc2)C1 | COCC(=O)N[C@@H]1CCCN(Cc2ccccc2)C1 | null | null | C(Cl)Cl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(CN2CCCCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#7:5]-[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4])-[C:9] | 97 | [{"value": 97.0, "product": "COCC(=O)N[C@H]1CN(CCC1)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "COCC(=O)N[C@H]1CN(CCC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 50 ml anhydrous tetrahydrofuran solution of 5.00 g (26.3 mmol) of (R)-1-phenylmethyl-3-aminopiperidine (Referential example 7) in a 300 ml three-necked flask was added a 50 ml anhydrous tetrahydrofuran solution of 3.20 g (1.2 eg.) of triethylamine, and, to this reaction mixture was added dropwise a 50 ml anhydrous... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1 | HCl | C(Cl)Cl.O | null | null | COCC(=O)Cl.N[C@@H]1CCCN(Cc2ccccc2)C1>C(Cl)Cl.O>COCC(=O)N[C@@H]1CCCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e6ecab20c64a406a8e7634f4425b54c1 | COCC(=O)N[C@@H]1CCCN(Cc2ccccc2)C1>>COCCN[C@@H]1CCCN(Cc2ccccc2)C1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)([O-])[O-].[Mg+2].COCC(=O)N[C@H]1CN(CCC1)CC1=CC=CC=C1.[OH-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>COCCN[C@H]1CN(CCC1)CC1=CC=CC=C1 | O=[C:4]([CH2:3][O:2][CH3:1])[NH:5][C@@H:6]1[CH2:7][CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18]1>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C@@H:6]1[CH2:7][CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18]1 | COCC(=O)N[C@@H]1CCCN(Cc2ccccc2)C1 | COCCN[C@@H]1CCCN(Cc2ccccc2)C1 | null | null | C(C)(=O)OCC.O1CCCC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CN2CCCCC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[#8:5]>>[#8:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[C:3] | 72 | [{"value": 72.0, "product": "COCCN[C@H]1CN(CCC1)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.7, "product": "COCCN[C@H]1CN(CCC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a 50 ml anhydrous tetrahydrofuran suspension of 0.87 g (2.0 eg.) of lithium aluminum hydride in a 300 ml round-bottomed flask was added dropwise a 20 ml anhydrous tetrahydrofuran solution of 3.00 g (11.4 mmol) of (R)-3-(2-methoxyacetylamino)-1-phenylmethylpiperidine. After stirred for 1 hour at room temperature, the... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | C1CC[NH]CC1.c1ccccc1 | Other | C(C)(=O)OCC.O1CCCC1 | null | 1 | COCC(=O)N[C@@H]1CCCN(Cc2ccccc2)C1>C(C)(=O)OCC.O1CCCC1>COCCN[C@@H]1CCCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ebab14589329403cb0aad45984b1c528 | CCCCN1CCC(CO)CC1.O=C(Cl)N1c2ccccc2C2CCCCC21>>CCCCN1CCC(CC2CCCC3c4ccccc4N(C(=O)O)C23)CC1 | ClC(=O)N1C2=CC=CC=C2C2CCCCC12.C1CCOC1.C(CCC)N1CCC(CC1)CO.C1CCOC1.C[Li]>>C(=O)(O)N1C2=CC=CC=C2C2CCCC(C12)CC1CCN(CC1)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][OH:24])[CH2:26][CH2:27]1.Cl[C:22]([N:21]1[c:20]2[c:15]([cH:16][cH:17][cH:18][cH:19]2)[CH:14]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:25]21)=[O:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH:14]3[c:15]4[cH:... | CCCCN1CCC(CO)CC1.O=C(Cl)N1c2ccccc2C2CCCCC21 | CCCCN1CCC(CC2CCCC3c4ccccc4N(C(=O)O)C23)CC1 | null | null | null | Acylation | OtherReaction | daaa169bbd82c6bb3bc9edab65c24b8665f67e454f89501db60b5753128f8c9c | 89dc7006595d86d858314bba2f7057755c60bb7654986b0568cafe8764794404 | c1ccc2c(c1)NC1C(CC3CCNCC3)CCCC21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[c:4])-[C:5](-[C:6])-[CH2;D2;+0:7]-[C:8]-[C:9].[C:10]-[C:11](-[CH2;D2;+0:12]-[OH;D1;+0:13])-[C:14]>>[C:9]-[C:8]-[CH;D3;+0:7](-[CH2;D2;+0:12]-[C:11](-[C:10])-[C:14])-[C:5](-[C:6])-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:13])-[c:4] | null | [] | null | null | 10 | MINUTE | 1-Butyl-4-piperidinylmethanol (0.500 g 2.12 mmol) was dissolved in dry THF (3 ml) and treated with methyllithium (1.5M solution in diethyl ether) 2.16 ml, 2.33 mmol) with stirring under nitrogen. After 10 minutes, N-chlorocarbonyl-1,2,3,4,4a,9a-hexahydrocarbazole (0.630 g, 2.68 mmol) (Ref: WO 89/09217) in dry THF (5 ml... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary alcohol | Carbamic acid | c1ccc2c(c1)[NH]C1CCCCC21 | c1ccc2c(c1)[NH]C1CCCCC21 | C1CC[NH]CC1.c1ccc2c(c1)[NH]C1CCCCC21 | HCl | null | null | 0.166667 | CCCCN1CCC(CO)CC1.O=C(Cl)N1c2ccccc2C2CCCCC21>>CCCCN1CCC(CC2CCCC3c4ccccc4N(C(=O)O)C23)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4f6016db03934931aac4c3c4d6a66417 | CCCCN1CCC(CC2CCCC3c4ccccc4N(C(=O)O)C23)CC1>>CCCCN1CCC(Cc2cccc3c4ccccc4n(C(=O)O)c23)CC1 | C(=O)(O)N1C2=CC=CC=C2C2CCCC(C12)CC1CCN(CC1)CCCC.ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O.ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O>>C(=O)(O)N1C2=CC=CC=C2C=2C=CC=C(C12)CC1CCN(CC1)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH:14]3[c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]4[N:21]([C:22](=[O:23])[OH:24])[CH:25]23)[CH2:26][CH2:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]4[cH:16][cH:17... | CCCCN1CCC(CC2CCCC3c4ccccc4N(C(=O)O)C23)CC1 | CCCCN1CCC(Cc2cccc3c4ccccc4n(C(=O)O)c23)CC1 | null | null | C(Cl)(Cl)Cl | Oxidation | OtherReaction | 235d31f3703f6d5aee1f563a32a6c415cf3b9b7d36153d01cdc413c0a36d7f52 | 29b8c465c2ca0e8412ed7ba786d08f9c3cb9639c5d5e81f94fec4733fdb413e6 | c1ccc2c(c1)[nH]c1c(CC3CCNCC3)cccc12 | [C:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH;D3;+0:7]2-[CH;D3;+0:8]-1-[N;H0;D3;+0:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[c:13](:[c:14]):[c:15]-2:[c:16]>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7]2:[c:15](:[c:16]):[c:13](:[c:14]):[n;H0;D3;+0:9](-[C:10](... | null | [] | null | null | null | null | N-Carboxy-[1-butylpiperidin-4-ylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole (0.530 g, 1.32 mmol) was dissolved in chloroform (25 ml) and treated with 2,3-dichloro-5,6-dicyano-1, 4-benzoquinone (0.329 g, 1.58 mmol) with stirring. The mixture was heated to reflux for 12 hours, cooled, and more 2,3-dichloro-5,6-dicyano-1,4-b... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid | null | c1ccc2c(c1)[NH]C1CCCCC21 | c1cccc2c1[nH]c1ccccc12 | C1CC[NH]CC1.c1cccc2c1[nH]c1ccccc12 | null | C(Cl)(Cl)Cl | null | null | CCCCN1CCC(CC2CCCC3c4ccccc4N(C(=O)O)C23)CC1>C(Cl)(Cl)Cl>CCCCN1CCC(Cc2cccc3c4ccccc4n(C(=O)O)c23)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-33fdd502bd9b4b6ab4abded4f14a5ab2 | C#CCBr.COC(=O)c1cc2ccccc2cc1O>>C#CCOc1cc2ccccc2cc1C(=O)OC | COC(=O)C1=CC2=CC=CC=C2C=C1O.[H-].[Na+].C(C#C)Br>>COC(=O)C1=CC2=CC=CC=C2C=C1OCC#C | Br[CH2:3][C:2]#[CH:1].[OH:4][c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[cH:13][c:14]1[C:15](=[O:16])[O:17][CH3:18]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[cH:13][c:14]1[C:15](=[O:16])[O:17][CH3:18] | C#CCBr.COC(=O)c1cc2ccccc2cc1O | C#CCOc1cc2ccccc2cc1C(=O)OC | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3]):[c:10] | 35 | [{"value": 35.0, "product": "COC(=O)C1=CC2=CC=CC=C2C=C1OCC#C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | Methyl-3-hydroxy-2-naphthoate (2.63 g, 0.013 mol) was dissolved in dry THF (80 ml) and treated with sodium hydride (80%) ((0.398 g, 0.013 mol), with stirring under N2. After 0.5 h, propargyl bromide (80% in toluene) (2.57 ml 0.017 mol) was added and the mixture heated to reflux. After 20 h, the reaction mixture was all... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ccccc2c1 | HBr | C1CCOC1 | null | 0.5 | C#CCBr.COC(=O)c1cc2ccccc2cc1O>C1CCOC1>C#CCOc1cc2ccccc2cc1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6d542e3dbdd248a898a4ea74dbd0c2eb | CCCCN1CCC(CN)CC1.Cc1nc2cc(Cl)cc(C(=O)O)c2o1>>CCCCN1CCC(CNC(=O)c2cc(Cl)cc3nc(C)oc23)CC1 | C(CCC)N1CCC(CC1)CN.ClC=1C=C(C2=C(N=C(O2)C)C1)C(=O)O.C(C(=O)Cl)(=O)Cl>>C(CCC)N1CCC(CC1)CNC(=O)C1=CC(=CC=2N=C(OC21)C)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][NH2:10])[CH2:24][CH2:25]1.O[C:11](=[O:12])[c:13]1[cH:14][c:15]([Cl:16])[cH:17][c:18]2[n:19][c:20]([CH3:21])[o:22][c:23]12>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][NH:10][C:11](=[O:12])[c:13]2[cH:14][c:15]([Cl:16])[cH:17][c:18]3[n:19][... | CCCCN1CCC(CN)CC1.Cc1nc2cc(Cl)cc(C(=O)O)c2o1 | CCCCN1CCC(CNC(=O)c2cc(Cl)cc3nc(C)oc23)CC1 | null | null | C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC1CCNCC1)c1cccc2ncoc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]1:[#8;a:6]:[c:7]:[#7;a:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]1:[#8;a:6]:[c:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | null | null | 5-Chloro-2-methylbenzoxazole-7-carboxylic acid (Ger. Offen. 2,225,544) is converted to its acid chloride by treatment with oxalyl chloride. The acid chloride is treated with N-(1-butyl-4-piperidinyl)methylamine in the presence of triethylamine to afford the title compound.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccc2ocnc2c1 | HO- | C(C)N(CC)CC | null | null | CCCCN1CCC(CN)CC1.Cc1nc2cc(Cl)cc(C(=O)O)c2o1>C(C)N(CC)CC>CCCCN1CCC(CNC(=O)c2cc(Cl)cc3nc(C)oc23)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6320ae92480446599727eaa48b88a8bc | O=[N+]([O-])c1cccc(S(=O)(=O)Nc2ccc3nsnc3c2)c1>>Nc1cccc(S(=O)(=O)Nc2ccc3nsnc3c2)c1 | [N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1>>NC=1C=C(C=CC1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]3[n:15][s:16][n:17][c:18]3[cH:19]2)[cH:20]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]3[n:15][s:16][n:17][c:18]3[cH:19]2)[cH:20]1 | O=[N+]([O-])c1cccc(S(=O)(=O)Nc2ccc3nsnc3c2)c1 | Nc1cccc(S(=O)(=O)Nc2ccc3nsnc3c2)c1 | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(Nc1ccc2nsnc2c1)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 solution of 1 g of 3-nitro-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide in 25 ml of methanol is hydrogenated to completion on 1 g of Raney Nickel at normal pressure and 20°. The solution is filtered, evaporated and 3-amino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide is obtained.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2nsnc2c1 | Other | [Ni].CO | null | null | O=[N+]([O-])c1cccc(S(=O)(=O)Nc2ccc3nsnc3c2)c1>[Ni].CO>Nc1cccc(S(=O)(=O)Nc2ccc3nsnc3c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4f6afdd55a85475bb49ce92f2b6145ed | CCc1ccccc1S(=O)(=O)Cl.Nc1ccc2nonc2c1>>CCc1ccccc1S(=O)(=O)Nc1ccc2nonc2c1 | NC1=CC=2C(=NON2)C=C1.C(C)C1=C(C=CC=C1)S(=O)(=O)Cl>>C(C)C1=C(C=CC=C1)S(=O)(=O)NC1=CC=2C(=NON2)C=C1 | Cl[S:9]([c:8]1[c:3]([CH2:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)(=[O:10])=[O:11].[NH2:12][c:13]1[cH:14][cH:15][c:16]2[n:17][o:18][n:19][c:20]2[cH:21]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[S:9](=[O:10])(=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]2[n:17][o:18][n:19][c:20]2[cH:21]1 | CCc1ccccc1S(=O)(=O)Cl.Nc1ccc2nonc2c1 | CCc1ccccc1S(=O)(=O)Nc1ccc2nonc2c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccc2nonc2c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH;D2;+0:11]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):[c:12] | null | [] | null | null | null | null | Analogously to Example 1, by reaction of 5-amino-2,1,3-benzoxadiazole (obtainable by reduction of 5-nitro-2,1,3-benzoxadiazole-1- or 3-N-oxide with triethyl phosphite) with 2-ethylbenzenesulfonyl chloride, 2-ethyl-N-(2,1,3-benzoxadiazol-5-yl)-1-benzenesulfonamide is obtained.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2nonc2c1 | HCl | null | null | null | CCc1ccccc1S(=O)(=O)Cl.Nc1ccc2nonc2c1>>CCc1ccccc1S(=O)(=O)Nc1ccc2nonc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7917d2b512334ae09464c8fd110ae2ba | CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1Br>>CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C#N | CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)Br)C.[Cu](C#N)C#N.N>>CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)C#N)C | Br[c:28]1[c:3]([CH2:2][CH3:1])[cH:4][c:5]2[n:6][o:7][n:8][c:9]2[c:10]1[NH:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][cH:18][c:19]2[c:20]([N:21]([CH3:22])[CH3:23])[cH:24][cH:25][cH:26][c:27]12>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[n:6][o:7][n:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][cH:18][c... | CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1Br | CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C#N | null | null | N1=CC=CC=C1 | Miscellaneous | OtherReaction | b5ec4c140b1cbe117e9bb656507e270a1fb4a9a3ce34a67d4138d3e556f53979 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=S(=O)(Nc1cccc2nonc12)c1cccc2ccccc12 | Br-[c;H0;D3;+0:1]1:[c:2](-[#7:3]):[c:4]2:[#7;a:5]:[#8;a:6]:[#7;a:7]:[c:8]:2:[c:9]:[c:10]:1-[C:11]>>[#7:3]-[c:2]1:[c:4]2:[#7;a:5]:[#8;a:6]:[#7;a:7]:[c:8]:2:[c:9]:[c:10](-[C:11]):[c;H0;D3;+0:1]:1-[C:12]#[N;D1;H0:13] | null | [] | null | null | null | null | A mixture of 4.6 g of 5-dimethylamino-N-(5-bromo-6-ethyl-2,1,3-benzoxadiazol-4-yl)-1-naphthalenesulfonamide and 1.3 g of copper cyanide is heated for 8 hours at 120° in 30 ml of pyridine. The mixture is poured onto aqueous ammonia solution, worked up in the customary manner and 5-dimethylamino- N-(5-cyano-6-ethyl-2,1,3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2nonc2c1 | c1ccc2nonc2c1 | c1ccc2nonc2c1.c1ccc2ccccc2c1 | Br- | N1=CC=CC=C1 | null | null | CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1Br>N1=CC=CC=C1>CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f96c52e9536a47d1afa277c765192b43 | CCO.CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C#N.[OH-]>>CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C(=O)O | CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)C#N)C.[OH-].[K+].C(C)O>>CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)NC1=C(C(=CC2=NON=C21)CC)C(=O)O)C | CC[OH:30].N#[C:29][c:28]1[c:3]([CH2:2][CH3:1])[cH:4][c:5]2[n:6][o:7][n:8][c:9]2[c:10]1[NH:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][cH:18][c:19]2[c:20]([N:21]([CH3:22])[CH3:23])[cH:24][cH:25][cH:26][c:27]12.[OH-:31]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[n:6][o:7][n:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15... | CCO.CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C#N.[OH-] | CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C(=O)O | null | null | O | Acylation | OtherReaction | e41cdaf6ecb9257286a05c8e01433d124042c5939fb4d758964487a1f4637b56 | e38d1b350c527156572f58ef95bb65354ed43ce776b83f166b6fd042d5d9aca9 | O=S(=O)(Nc1cccc2nonc12)c1cccc2ccccc12 | C-C-[OH;D1;+0:1].N#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[OH-;D0:8]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[OH;D1;+0:8]):[c:4] | null | [] | null | null | 8 | HOUR | A solution of 1 g of 5-dimethylamino-N-(5-cyano-6-ethyl-2,1,3-benzoxadiazol-4-yl)-1-naphthalenesulfonamide and 0.7 g of potassium hydroxide in 20 ml of ethanol and 5 ml of water is bailed with stirring for 8 hours. The solvents are removed, the residue is dissolved in water and treated with hydrochloric acid and 5-dime... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Carboxylic acid | null | null | c1ccc2nonc2c1.c1ccc2ccccc2c1 | Other | O | null | 8 | CCO.CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C#N.[OH-]>O>CCc1cc2nonc2c(NS(=O)(=O)c2cccc3c(N(C)C)cccc23)c1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7fa891adf0d455598641c30d6e12a91 | CC=O.Nc1ccc(S(=O)(=O)Nc2ccc3nsnc3c2)cc1>>CCNc1ccc(S(=O)(=O)Nc2ccc3nsnc3c2)cc1 | Cl.NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1.C(C)=O.C(#N)[BH3-].[Na+]>>C(C)NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=2C(=NSN2)C=C1 | O=[CH:2][CH3:1].[NH2:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]3[n:16][s:17][n:18][c:19]3[cH:20]2)[cH:21][cH:22]1>>[CH3:1][CH2:2][NH:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]3[n:16][s:17][n:18][c:19]3[cH:20]2)[cH:21][cH:22]1 | CC=O.Nc1ccc(S(=O)(=O)Nc2ccc3nsnc3c2)cc1 | CCNc1ccc(S(=O)(=O)Nc2ccc3nsnc3c2)cc1 | null | [Ti](Cl)(Cl)(Cl)Cl | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=S(=O)(Nc1ccc2nsnc2c1)c1ccccc1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | HOUR | A solution of 6 g of 4-amino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide and 0.5 g of titanium tetrachloride in 100 ml of methanol is treated with 1 ml of freshly distilled acetaldehyde. 4 g of sodium cyanoborohydride are then added thereto and the mixture is stirred for 30 hours. Cold half-concentrated hydroch... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2nsnc2c1 | Other | [Ti](Cl)(Cl)(Cl)Cl.CO | null | 30 | CC=O.Nc1ccc(S(=O)(=O)Nc2ccc3nsnc3c2)cc1>[Ti](Cl)(Cl)(Cl)Cl.CO>CCNc1ccc(S(=O)(=O)Nc2ccc3nsnc3c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ffa107eae87c458391df6e58d5d78f6e | C[Si](C)(C)N=[N+]=[N-].N#Cc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(-c3nnn[nH]3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C#N)C=C1.C(CCC)[Sn](CCCC)=O.C[Si](C)(C)N=[N+]=[N-]>>O(C1=CC=CC=C1)C1=CC=C(C=C1)C1=NN=NN1 | C[Si](C)(C)[N:14]=[N+:13]=[N-:12].[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:15][cH:16]2)[cH:17][cH:18]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9](-[c:10]3[n:11][n:12][n:13][nH:14]3)[cH:15][cH:16]2)[cH:17][cH:18]1 | C[Si](C)(C)N=[N+]=[N-].N#Cc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(-c3nnn[nH]3)cc2)cc1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 22a456949a340700c38f1369557e2324d3627ca94291920d5593a13d13f086c0 | b0b652611f3449be50404e3527083f5e03f8f4207de666d5db2f0953bd23d0a3 | c1ccc(Oc2ccc(-c3nnn[nH]3)cc2)cc1 | C-[Si](-C)(-C)-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[nH;D2;+0:1]:1):[c:9]:[c:10] | null | [] | null | null | null | null | A solution of 4-phenoxybenzonitrile (9.87 g), dibutyltin oxide (3.88 g), and trimethylsilyl azide (33.5 ml) in anhydrous toluene (200 ml) was heated to reflux for 6 hours. The reaction mixture was washed with 1.6M sodium hydroxide (2×250 ml). The combined aqueous layer was washed with diethyl ether (4×120 ml) then acid... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile.Silyl protective group | null | null | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1nnn[nH]1 | Other | C1(=CC=CC=C1)C | null | null | C[Si](C)(C)N=[N+]=[N-].N#Cc1ccc(Oc2ccccc2)cc1>C1(=CC=CC=C1)C>c1ccc(Oc2ccc(-c3nnn[nH]3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fd2ce529eb5e4230a968d9b7a9207cfc | C#Cc1ccc(C#N)cc1.O=[N+]([O-])c1ccc(Br)o1>>N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])o2)cc1 | BrC=1OC(=CC1)[N+](=O)[O-].C(C)N(CC)CC.C(#C)C1=CC=C(C#N)C=C1>>[N+](=O)([O-])C1=CC=C(O1)C#CC1=CC=C(C#N)C=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[CH:8])[cH:17][cH:18]1.Br[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[o:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[C:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[o:16]2)[cH:17][cH:18]1 | C#Cc1ccc(C#N)cc1.O=[N+]([O-])c1ccc(Br)o1 | N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])o2)cc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)#N | C-C Coupling | Sonogashira alkyne_aryl halide | 85c427816ae28bd4dbb19650a00c34ca6489eaef6ce7658febdd08dde476e105 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccco1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | null | null | 8 | HOUR | To a solution of 2-bromo-5-nitrofuran (1.65 g) and triethylamine (34 ml) in anhydrous acetonitrile (55 ml) under nitrogen was added bis(triphenylphosphine)palladium dichloride (130 mg) and cuprous iodide (35 mg). 4-Ethynylbenzonitrile (1.09 g) was added and the reaction mixture was stirred under nitrogen overnight. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccoc1 | c1ccoc1 | c1ccccc1.c1ccoc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)#N | null | 8 | C#Cc1ccc(C#N)cc1.O=[N+]([O-])c1ccc(Br)o1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)#N>N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])o2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f537d62089cd4cba9bc833054c2f705b | C#Cc1ccc(C#N)cc1.O=[N+]([O-])c1ccc(Br)s1>>N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1 | [Cl-].[Na+].C(#C)C1=CC=C(C#N)C=C1.BrC=1SC(=CC1)[N+](=O)[O-].C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(S1)C#CC1=CC=C(C#N)C=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[CH:8])[cH:17][cH:18]1.Br[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[s:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[C:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[s:16]2)[cH:17][cH:18]1 | C#Cc1ccc(C#N)cc1.O=[N+]([O-])c1ccc(Br)s1 | N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C=O)C.C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 80f1154e8228406a6c3574cdd1c2a206480f305ea213bae402b2ac8502ab2f9e | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1cccs1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | null | null | 3 | DAY | To a solution of 4-ethynylbenzonitrile (0.5 g), 2-bromo-5-nitrothiophene (0.9 g) and bis(triphenylphosphine)palladium dichloride (83 mg) in anhydrous dimethylformamide (4 ml) was added triethylamine (2.2 ml). The reaction mixture was stirred at room temperature for 3 days then ethyl acetate (200 ml) and saturated sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccsc1 | c1ccsc1 | c1ccccc1.c1ccsc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C.C(C)(=O)OCC | null | 72 | C#Cc1ccc(C#N)cc1.O=[N+]([O-])c1ccc(Br)s1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C.C(C)(=O)OCC>N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ba45a428014e4c71895cdbed1fea1c2d | C[Si](C)(C)N=[N+]=[N-].N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1>>O=[N+]([O-])c1ccc(C#Cc2ccc(-c3nnn[nH]3)cc2)s1 | [N+](=O)([O-])C1=CC=C(S1)C#CC1=CC=C(C#N)C=C1.C(CCC)[Sn](CCCC)=O.C[Si](C)(C)N=[N+]=[N-]>>[N+](=O)([O-])C1=CC=C(S1)C#CC1=CC=C(C=C1)C1=NN=NN1 | C[Si](C)(C)[N:18]=[N+:16]=[N-:17].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([C:8]#[C:9][c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:19][cH:20]2)[s:21]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([C:8]#[C:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[n:15][n:16][n:17][nH:18]3)[cH:19][cH:20]2)[s:21]1 | C[Si](C)(C)N=[N+]=[N-].N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1 | O=[N+]([O-])c1ccc(C#Cc2ccc(-c3nnn[nH]3)cc2)s1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 22a456949a340700c38f1369557e2324d3627ca94291920d5593a13d13f086c0 | b0b652611f3449be50404e3527083f5e03f8f4207de666d5db2f0953bd23d0a3 | C(#Cc1cccs1)c1ccc(-c2nnn[nH]2)cc1 | C-[Si](-C)(-C)-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[nH;D2;+0:1]:1):[c:9]:[c:10] | null | [] | null | null | null | null | To a solution of 4-[(5-nitro-2-thienyl)ethynyl]benzonitrile (0.6 g) and dibutyltin oxide (59 mg) in anhydrous toluene (30 ml) was added trimethylsilyl azide (0.5 ml). The reaction mixture was heated to reflux in the dark for 12 hours, then allowed to cool to room temperature. The reaction mixture was washed with satura... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile.Silyl protective group | null | null | c1nnn[nH]1 | c1ccsc1.c1ccccc1.c1nnn[nH]1 | Other | C1(=CC=CC=C1)C | null | null | C[Si](C)(C)N=[N+]=[N-].N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1>C1(=CC=CC=C1)C>O=[N+]([O-])c1ccc(C#Cc2ccc(-c3nnn[nH]3)cc2)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25fc14e42f424677aa73d3c6c5b9ae9d | C[Si](C)(C)N=[N+]=[N-].N#CCc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(Cc3nnn[nH]3)cc2)cc1 | [OH-].[Na+].O(C1=CC=CC=C1)C1=CC=C(C=C1)CC#N.C[Si](C)(C)N=[N+]=[N-].C(CCC)[Sn](CCCC)=O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CC1=NN=NN1 | C[Si](C)(C)[N:15]=[N+:13]=[N-:14].[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][C:11]#[N:12])[cH:16][cH:17]2)[cH:18][cH:19]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][c:11]3[n:12][n:13][n:14][nH:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1 | C[Si](C)(C)N=[N+]=[N-].N#CCc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(Cc3nnn[nH]3)cc2)cc1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 22a456949a340700c38f1369557e2324d3627ca94291920d5593a13d13f086c0 | b0b652611f3449be50404e3527083f5e03f8f4207de666d5db2f0953bd23d0a3 | c1ccc(Oc2ccc(Cc3nnn[nH]3)cc2)cc1 | C-[Si](-C)(-C)-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[C:6]-[c:7]>>[c:7]-[C:6]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[nH;D2;+0:1]:1 | null | [] | null | null | null | null | To a solution of 4-phenoxyphenylacetonitrile (1.16 g) in anhydrous toluene (30 ml) was added trimethylsilylazide (1.1 ml) and dibutyltin oxide (0.19 g). The mixture was heated to reflux for 19 hours then allowed to cool to room temperature. The reaction mixture was then added to 1M sodium hydroxide (100 ml) and washed ... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile.Silyl protective group | null | null | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1nnn[nH]1 | Other | C1(=CC=CC=C1)C | null | null | C[Si](C)(C)N=[N+]=[N-].N#CCc1ccc(Oc2ccccc2)cc1>C1(=CC=CC=C1)C>c1ccc(Oc2ccc(Cc3nnn[nH]3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c7cc9bbc71144c7ae9f1e2d0e680324 | O=C1NC(=O)c2cc(Cl)ccc21>>Clc1cccc2c1CNC2 | ClC=1C=C2C(C(=O)NC2=O)=CC1.Cl>>ClC1=C2CNCC2=CC=C1 | O=[C:8]1[c:7]2[cH:2][c:3]([Cl:1])[cH:4][cH:5][c:6]2[C:10](=O)[NH:9]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][NH:9][CH2:10]2 | O=C1NC(=O)c2cc(Cl)ccc21 | Clc1cccc2c1CNC2 | null | null | O1CCCC1 | Functional Group Addition | OtherReaction | 106327c249cf5b274d3cd701f19740fc83f3bb2c9dcfabcd3e04bdc802a8246e | c611a163eef2f0598d60d9d37ad9b17d64e4ef0dbf9dfba690515b4ad6bf1fa7 | c1ccc2c(c1)CNC2 | O=[C;H0;D3;+0:1]1-[#7:2]-[C;H0;D3;+0:3](=O)-[c:4]2:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:7]):[c:8]:[c:9]:[c:10]:2-1>>[Cl;H0;D1;+0:7]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:8]:[c:9]:[c:10]2:[c:4]:1-[CH2;D2;+0:3]-[#7:2]-[CH2;D2;+0:1]-2 | null | [] | null | null | null | null | To a solution of 4-chlorophthalimide (60 g) in 1 liter of tetrahydrofuran was added borane-methyl sulfide complex (100 ml of 10M), and the mixture was refluxed overnight. After cooling, 100 ml of 6N hydrochloric acid was added slowly, the mixture refluxed for 2 hours, and then filtered. The filtrate was concentrated un... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide | Aromatic halide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | Other | O1CCCC1 | null | null | O=C1NC(=O)c2cc(Cl)ccc21>O1CCCC1>Clc1cccc2c1CNC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0591013fd92545f5bf5092992c26919f | CSC1=NCCS1.Clc1cccc2c1CNC2>>Clc1cccc2c1CN(C1=NCCS1)C2 | ClC1=C2CNCC2=CC=C1.CSC=1SCCN1.C1=C(C=CC2=CC=CC=C12)S(=O)(=O)O>>ClC1=C2CN(CC2=CC=C1)C=1SCCN1 | CS[C:10]1=[N:11][CH2:12][CH2:13][S:14]1.[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][NH:9][CH2:15]2>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][N:9]([C:10]1=[N:11][CH2:12][CH2:13][S:14]1)[CH2:15]2 | CSC1=NCCS1.Clc1cccc2c1CNC2 | Clc1cccc2c1CN(C1=NCCS1)C2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a668efb51512d8228bf8a4303df72f4ce701e31a18e7cebe5b171cd8ab0c703e | bfc582950bdf0b5fb9b3d55b1008f32b1f1c2ec643ca7f4d617bfc2865cc9bc5 | c1ccc2c(c1)CN(C1=NCCS1)C2 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#16:5]-1.[C:6]1-[NH;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[#16:5]1-[C:4]-[C:3]-[#7:2]=[C;H0;D3;+0:1]-1-[N;H0;D3;+0:7]1-[C:6]-[c:10]:[c:9]-[C:8]-1 | null | [] | 150 | CELSIUS | null | null | A mixture of 4-chloroisoindoline (700 mg), 2-methylthio-2-thiazoline (600 mg), and β-naphthylsulfonic acid (35 mg) was heated at 150° C. for 30 minutes. The product was cooled, dissolved in methylene chloride, washed with water, the organic layer dried over anhydrous potassium carbonate, filtered, and solvent removed f... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide.Monosulfide | Tertiary amine.Monosulfide | C1=NCCS1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.C1=NCCS1 | c1ccc2c(c1)C[NH]C2.C1=NCCS1 | Other | C(Cl)Cl | 150 | null | CSC1=NCCS1.Clc1cccc2c1CNC2>C(Cl)Cl>Clc1cccc2c1CN(C1=NCCS1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0aed4da618f94372b6ebcb5dce352131 | CCOC1=NCCO1.Fc1cccc2c1CNC2>>Fc1cccc2c1CN(C1=NCCO1)C2 | FC1=C2CNCC2=CC=C1.C(C)OC=1OCCN1.C1=C(C=CC2=CC=CC=C12)S(=O)(=O)O>>FC1=C2CN(CC2=CC=C1)C=1OCCN1 | CCO[C:10]1=[N:11][CH2:12][CH2:13][O:14]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][NH:9][CH2:15]2>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH2:8][N:9]([C:10]1=[N:11][CH2:12][CH2:13][O:14]1)[CH2:15]2 | CCOC1=NCCO1.Fc1cccc2c1CNC2 | Fc1cccc2c1CN(C1=NCCO1)C2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Displacement of ethoxy group by secondary amine | f6da5addeff690dff47c54c98a2b6a6446d1a91d82b399c0daec008e45bdf8b7 | d8eb8c9b1e09b7f4b257948057ae13ffa7a454df2815ac36c03139e6598690c5 | c1ccc2c(c1)CN(C1=NCCO1)C2 | C-C-O-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#8:5]-1.[C:6]1-[NH;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[#7:2]1=[C;H0;D3;+0:1](-[N;H0;D3;+0:7]2-[C:6]-[c:10]:[c:9]-[C:8]-2)-[#8:5]-[C:4]-[C:3]-1 | null | [] | 100 | CELSIUS | 1 | HOUR | A mixture of 4-fluoroisoindoline (400 mg), 2-ethoxy-2-oxazoline (400 mg), and β-naphthylsulfonic acid (30 mg) in 50 ml of toluene was stirred at 100° C. for 1 hour. The solvent as removed under reduced pressure, and the residue chromatographed on silica gel, eluting with 1-4% methanol in ethyl acetate, to give 4-fluoro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amine | Ether.Tertiary amine | C1=NCCO1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.C1=NCCO1 | c1ccc2c(c1)C[NH]C2.C1=NCCO1 | HO- | C1(=CC=CC=C1)C | 100 | 1 | CCOC1=NCCO1.Fc1cccc2c1CNC2>C1(=CC=CC=C1)C>Fc1cccc2c1CN(C1=NCCO1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c4710f63ab8144a9acdfc1350b467c98 | CCCCCCc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C.O=C(OCc1ccccc1)c1ccc(O)nc1>>CCCCCCc1cc2c(cc1C(=O)Oc1ccc(C(=O)OCc3ccccc3)cn1)C(C)(C)CCC2(C)C | C(CCCCC)C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)O.OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1.C1(CCCCC1)N=C=NC1CCCCC1>>C(CCCCC)C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1 | O[C:13]([c:12]1[c:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:8][c:9]2[c:10]([cH:11]1)[C:32]([CH3:33])([CH3:34])[CH2:35][CH2:36][C:37]2([CH3:38])[CH3:39])=[O:14].[OH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30][n:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4]... | CCCCCCc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C.O=C(OCc1ccccc1)c1ccc(O)nc1 | CCCCCCc1cc2c(cc1C(=O)Oc1ccc(C(=O)OCc3ccccc3)cn1)C(C)(C)CCC2(C)C | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(OCc1ccccc1)c1ccc(OC(=O)c2ccc3c(c2)CCCC3)nc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 57 | [{"value": 57.0, "product": "C(CCCCC)C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 6 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid were dissolved in 180 ml of methylene chloride. After the addition of a solution of 4.8 g of benzyl 6-hydroxy-nicotinate in 160 ml of methylene chloride and of 2.3 g of 4-dimethylaminopyridine, the solution was cooled to 0° C. and tre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccncc1.c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | 0 | 2 | CCCCCCc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C.O=C(OCc1ccccc1)c1ccc(O)nc1>CN(C1=CC=NC=C1)C.C(Cl)Cl>CCCCCCc1cc2c(cc1C(=O)Oc1ccc(C(=O)OCc3ccccc3)cn1)C(C)(C)CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d21f97b1712426ea5d91e06fbf86981 | CCCCCCc1cc2c(cc1Br)C(C)(C)CCC2(C)C.O=C=O>>CCCCCCc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C | C(=O)=O.C(C)(C)(C)[Li].BrC=1C=C2C(CCC(C2=CC1CCCCCC)(C)C)(C)C.Cl>>C(CCCCC)C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)O | Br[c:12]1[c:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:8][c:9]2[c:10]([cH:11]1)[C:16]([CH3:17])([CH3:18])[CH2:19][CH2:20][C:21]2([CH3:22])[CH3:23].[C:13](=[O:14])=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][c:9]2[c:10]([cH:11][c:12]1[C:13](=[O:14])[OH:15])[C:16]([CH3:17])([CH3:18])[CH2:19][CH2... | CCCCCCc1cc2c(cc1Br)C(C)(C)CCC2(C)C.O=C=O | CCCCCCc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C | null | null | CCCCC.O1CCCC1 | Acylation | OtherReaction | 2c77db6aaec596a76b7a465634b3055972748ecc9b259d7fb098a14192761a6e | d0d963f3850574b1f0fda744314036458b2dd627cb0c4e2f893b9c52a88ad449 | c1ccc2c(c1)CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[O;H0;D1;+0:9]>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:8](=[O;D1;H0:7])-[OH;D1;+0:9]):[c:2]:[c:3] | null | [] | -78 | CELSIUS | 1 | HOUR | 15 g of 6-bromo-7-hexyl-1,1,4,4-tetramethyl-1, 2,3,4-tetrahydro-naphthalene were dissolved in 180 ml of tetrahydrofuran and treated dropwise at -78° C. with 64.5 ml of a 1.5 molar solution of tert.butyl-lithium in pentane. After stirring at -78° C. for 1 hour, a carbon dioxide stream was conducted vigorously into the r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Carboxylic acid | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Br- | CCCCC.O1CCCC1 | -78 | 1 | CCCCCCc1cc2c(cc1Br)C(C)(C)CCC2(C)C.O=C=O>CCCCC.O1CCCC1>CCCCCCc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e55407ae46c4beabc510d9038b027f8 | O=C(O)c1ccc(O)nc1.OCc1ccccc1>>O=C(OCc1ccccc1)c1ccc(O)nc1 | OC1=NC=C(C(=O)O)C=C1.S(O)(O)(=O)=O.C(C1=CC=CC=C1)O>>OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1 | O[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([OH:15])[n:16][cH:17]1.[OH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([OH:15])[n:16][cH:17]1 | O=C(O)c1ccc(O)nc1.OCc1ccccc1 | O=C(OCc1ccccc1)c1ccc(O)nc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(OCc1ccccc1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[OH;D1;+0:8]-[C:9]-[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:8]-[C:9]-[c:10])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | 30 g of 6-hydroxynicotinic acid were treated with 500 ml of benzyl alcohol and 1 ml of concentrated sulfuric acid. After boiling at reflux for 3 days, the reaction mixture was poured on to ice-water, extracted several times with ethyl acetate, washed with water, dried over sodium sulfate and evaporated, firstly in a wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccncc1 | HO- | null | null | null | O=C(O)c1ccc(O)nc1.OCc1ccccc1>>O=C(OCc1ccccc1)c1ccc(O)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-315e56646a1f498680f098449e45c81e | CCCCC#Cc1ccc2c(c1)C(C)(C)CCCC2>>CCCCCCc1ccc2c(c1)C(C)(C)CCCC2 | C(#CCCCC)C=1C=CC2=C(C(CCCC2)(C)C)C1>>C(CCCCC)C=1C=CC2=C(C(CCCC2)(C)C)C1 | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[C:13]([CH3:14])([CH3:15])[CH2:16][CH2:17][CH2:18][CH2:19]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[C:13]([CH3:14])([CH3:15])[CH2:16][CH2:17][CH2:18][CH2:19]2 | CCCCC#Cc1ccc2c(c1)C(C)(C)CCCC2 | CCCCCCc1ccc2c(c1)C(C)(C)CCCC2 | null | [Pd] | C(C)(=O)OCC | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc2c(c1)CCCCC2 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | This alkyne was dissolved in 30 ml of ethy acetate and hydrogenated over 2 g of Pd/C (10%) at room temperature and under 1 atm H2. Filtration over diatomaceous earth and removal of the solvent gave 3.08 g of 2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene as a colorless oil (GC purity: 98%).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccc2c(c1)CCCCC2 | null | [Pd].C(C)(=O)OCC | null | null | CCCCC#Cc1ccc2c(c1)C(C)(C)CCCC2>[Pd].C(C)(=O)OCC>CCCCCCc1ccc2c(c1)C(C)(C)CCCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f15578709608425ca7e804635f32e399 | BrBr.CCCCCCc1ccc2c(c1)C(C)(C)CCCC2>>CCCCCCc1cc2c(cc1Br)CCCCC2(C)C | C(CCCCC)C=1C=CC2=C(C(CCCC2)(C)C)C1.BrBr>>BrC=1C(=CC2=C(CCCCC2(C)C)C1)CCCCCC | Br[Br:13].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][c:9]2[c:10]([cH:11][cH:12]1)[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2([CH3:19])[CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][c:9]2[c:10]([cH:11][c:12]1[Br:13])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2([CH3:19])[CH3:20] | BrBr.CCCCCCc1ccc2c(c1)C(C)(C)CCCC2 | CCCCCCc1cc2c(cc1Br)CCCCC2(C)C | null | [Fe] | C(Cl)Cl | Functional Group Interconversion | Bromination | 4a6454c45deb843afe911cae2e4e04b415b9aa2380a0e17448996842b1f937f0 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2c(c1)CCCCC2 | Br-[Br;H0;D1;+0:1].[C:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[C:2]):[c:4] | null | [] | null | null | 30 | MINUTE | This 3.08 g of 2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene were dissolved in 35 ml of CH2Cl2, treated at 0° with a spatula tip of Fe powder and then reacted with a solution of 0.67 ml of Br2 (1.1 eq.) in 5 ml of CH2Cl2. After 30 min., the mixture was poured on to ice, extracted with diethyl ether, wash... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCCCC2 | c1ccc2c(c1)CCCCC2 | c1ccc2c(c1)CCCCC2 | HBr | [Fe].C(Cl)Cl | null | 0.5 | BrBr.CCCCCCc1ccc2c(c1)C(C)(C)CCCC2>[Fe].C(Cl)Cl>CCCCCCc1cc2c(cc1Br)CCCCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bec0b13badfd4aa9b7a9fafcead8a865 | CCCCCCc1cc2c(cc1Br)CCCCC2(C)C.O=C=O>>CCCCCCc1cc2c(cc1C(=O)O)CCCCC2(C)C | C(=O)=O.[Li]CCCC.BrC=1C(=CC2=C(CCCCC2(C)C)C1)CCCCCC>>C(CCCCC)C1=CC2=C(CCCCC2(C)C)C=C1C(=O)O | Br[c:12]1[c:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:8][c:9]2[c:10]([cH:11]1)[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2([CH3:21])[CH3:22].[C:13](=[O:14])=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][c:9]2[c:10]([cH:11][c:12]1[C:13](=[O:14])[OH:15])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2([CH3:21]... | CCCCCCc1cc2c(cc1Br)CCCCC2(C)C.O=C=O | CCCCCCc1cc2c(cc1C(=O)O)CCCCC2(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | ba320636bb74c150bbda303a1bba98ca25ba6cb1c2e144aaf6ffcd505d4cde2b | d0d963f3850574b1f0fda744314036458b2dd627cb0c4e2f893b9c52a88ad449 | c1ccc2c(c1)CCCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[O;H0;D1;+0:9]>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:8](=[O;D1;H0:7])-[OH;D1;+0:9]):[c:2]:[c:3] | null | [] | null | null | 40 | MINUTE | This 3.21 g of 2-bromo-3-hexyl-5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene were placed in 30 ml of abs. tetrahydrofuran under Ar and treated at -78° with 6.75 ml of 1.55M nBuLi (hexane) (1.1 eq.). The metal/halogen exchange was followed by gas chromatography (GC). After 40 min., a large excess of CO2 gas was i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Carboxylic acid | c1ccc2c(c1)CCCCC2 | c1ccc2c(c1)CCCCC2 | c1ccc2c(c1)CCCCC2 | Br- | O1CCCC1 | null | 0.666667 | CCCCCCc1cc2c(cc1Br)CCCCC2(C)C.O=C=O>O1CCCC1>CCCCCCc1cc2c(cc1C(=O)O)CCCCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-998b94bdae2a4efb8c11261a196e92e3 | C[Si](C)(C)C/C=C/CO.O=C(O)c1ccc(O)nc1>>C[Si](C)(C)C/C=C/COC(=O)c1ccc(O)nc1 | C[Si](C/C=C/CO)(C)C.OC1=NC=C(C(=O)O)C=C1.C1(CCCCC1)N=C=NC1CCCCC1>>OC1=NC=C(C(=O)OC\C=C\C[Si](C)(C)C)C=C1 | [CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5]/[CH:6]=[CH:7]/[CH2:8][OH:9].O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([OH:16])[n:17][cH:18]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5]/[CH:6]=[CH:7]/[CH2:8][O:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([OH:16])[n:17][cH:18]1 | C[Si](C)(C)C/C=C/CO.O=C(O)c1ccc(O)nc1 | C[Si](C)(C)C/C=C/COC(=O)c1ccc(O)nc1 | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]/[C:9]=[C:10]/[C:11]-[OH;D1;+0:12]>>[C:8]/[C:9]=[C:10]/[C:11]-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 38 | [{"value": 38.0, "product": "OC1=NC=C(C(=O)OC\\C=C\\C[Si](C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.3 g of 4-trimethylsilyl-(E)-but-2-en-1-ol (synthesis described in J. Org. Chem. 1984, 49, 4092), 1.08 g of 6-hydroxy-nicotinic acid and 178 mg of 4-dimethylaminopyridine were placed in succession in 30 ml of abs. dimethylformamide. 1.77 g (1.1 eq.) of dicyclohexylcarbodiimide were added thereto at 0° and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | null | C[Si](C)(C)C/C=C/CO.O=C(O)c1ccc(O)nc1>CN(C1=CC=NC=C1)C.CN(C=O)C>C[Si](C)(C)C/C=C/COC(=O)c1ccc(O)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93220ca147a845ff95c1f6c722b6fe11 | CCCC/C=C\c1cc2c(cc1Br)C(C)(C)CCC2(C)C.O=C=O>>CCCC/C=C\c1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C | [Li]CCCC.BrC=1C=C2C(CCC(C2=CC1\C=C/CCCC)(C)C)(C)C.C(=O)=O>>C(=C/CCCC)/C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)O | Br[c:12]1[c:7](/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][CH3:1])[cH:8][c:9]2[c:10]([cH:11]1)[C:16]([CH3:17])([CH3:18])[CH2:19][CH2:20][C:21]2([CH3:22])[CH3:23].[C:13](=[O:14])=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[c:7]1[cH:8][c:9]2[c:10]([cH:11][c:12]1[C:13](=[O:14])[OH:15])[C:16]([CH3:17])([CH3:18])[CH2:19][C... | CCCC/C=C\c1cc2c(cc1Br)C(C)(C)CCC2(C)C.O=C=O | CCCC/C=C\c1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C | null | null | O1CCCC1 | Acylation | OtherReaction | 2c77db6aaec596a76b7a465634b3055972748ecc9b259d7fb098a14192761a6e | d0d963f3850574b1f0fda744314036458b2dd627cb0c4e2f893b9c52a88ad449 | c1ccc2c(c1)CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](/[C:5]=[C:6]\[C:7]):[c:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[O;H0;D1;+0:11]>>[C:7]/[C:6]=[C:5]\[c:4](:[c:8]):[c;H0;D3;+0:1](-[C;H0;D3;+0:10](=[O;D1;H0:9])-[OH;D1;+0:11]):[c:2]:[c:3] | null | [] | null | null | null | null | 3.72 g of (Z)-6-bromo-7-hex-1-enyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene (75% pure) were placed in 25 ml of abs. tetrahydrofuran and treated at -75° with 8.25 ml of 1.55M n-BuLi (hexane) (1.2 eq.). After 1/2h., a CO2 stream was conducted vigorously through the solution for 30 min., with the temperature ris... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Carboxylic acid | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Br- | O1CCCC1 | null | null | CCCC/C=C\c1cc2c(cc1Br)C(C)(C)CCC2(C)C.O=C=O>O1CCCC1>CCCC/C=C\c1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-34b88de89a834c5b93af8ffabf69f38c | CCCCCOc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C.O=C(OCc1ccccc1)c1ccc(O)nc1>>CCCCCOc1cc2c(cc1C(=O)Oc1ccc(C(=O)OCc3ccccc3)cn1)C(C)(C)CCC2(C)C | C(CCCC)OC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)O.BrC=1C=C2C(CCC(C2=CC1OCCCCC)(C)C)(C)C.C(C)(C)(C)[Li].OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1.C(=O)=O>>C(CCCC)OC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1 | O[C:13]([c:12]1[c:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:8][c:9]2[c:10]([cH:11]1)[C:32]([CH3:33])([CH3:34])[CH2:35][CH2:36][C:37]2([CH3:38])[CH3:39])=[O:14].[OH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30][n:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C... | CCCCCOc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C.O=C(OCc1ccccc1)c1ccc(O)nc1 | CCCCCOc1cc2c(cc1C(=O)Oc1ccc(C(=O)OCc3ccccc3)cn1)C(C)(C)CCC2(C)C | null | null | null | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(OCc1ccccc1)c1ccc(OC(=O)c2ccc3c(c2)CCCC3)nc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | In analogy to Example 1, by metallating 6-bromo-7-pentoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene with tert.butyl-lithium and reacting with carbon dioxide gas there was prepared 3-pentoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (m.p. 67°-68° C., from hexane). Reaction of this aci... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccncc1.c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | CCCCCOc1cc2c(cc1C(=O)O)C(C)(C)CCC2(C)C.O=C(OCc1ccccc1)c1ccc(O)nc1>>CCCCCOc1cc2c(cc1C(=O)Oc1ccc(C(=O)OCc3ccccc3)cn1)C(C)(C)CCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0833dde5dcd44e279ff441b2ca2671fd | CC(C)(C)[Si](C)(C)Oc1ccc(Br)cc1C12CC3CC(CC(C3)C1)C2.O=C=O>>CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)O)cc1C12CC3CC(CC(C3)C1)C2 | C(=O)=O.Cl.C(CCC)[Li].[Cl-].[NH4+].C12(CC3CC(CC(C1)C3)C2)C2=C(O[Si](C)(C)C(C)(C)C)C=CC(=C2)Br>>C12(CC3CC(CC(C1)C3)C2)C=2C=C(C(=O)O)C=CC2O[Si](C)(C)C(C)(C)C | Br[c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:17]([C:18]23[CH2:19][CH:20]4[CH2:21][CH:22]([CH2:23][CH:24]([CH2:25]4)[CH2:26]2)[CH2:27]3)[cH:16]1.[C:13](=[O:14])=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:... | CC(C)(C)[Si](C)(C)Oc1ccc(Br)cc1C12CC3CC(CC(C3)C1)C2.O=C=O | CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)O)cc1C12CC3CC(CC(C3)C1)C2 | null | null | CCCCCC.O1CCCC1 | Acylation | OtherReaction | 07ac4a201d363784a28677e85b547e572f4793f5010c94050885192cae13600e | d0d963f3850574b1f0fda744314036458b2dd627cb0c4e2f893b9c52a88ad449 | c1ccc(C23CC4CC(CC(C4)C2)C3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[O;H0;D1;+0:8]>>[O;D1;H0:6]=[C;H0;D3;+0:7](-[OH;D1;+0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 1.5 | HOUR | 9.3 g of (2-adamantan-1-yl-4-bromo-phenoxy)-tert-butyl-dimethylsilane were dissolved in 120 ml of absolute tetrahydrofuran and treated dropwise at -78° C. with 15.5 ml of a 1.6 molar solution of n-butyl-lithium in hexane. After stirring at -78° C. for 1.5 hours, a vigorous stream of carbon dioxide was introduced for on... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C2CC3CC1CC(C2)C3 | Br- | CCCCCC.O1CCCC1 | -78 | 1.5 | CC(C)(C)[Si](C)(C)Oc1ccc(Br)cc1C12CC3CC(CC(C3)C1)C2.O=C=O>CCCCCC.O1CCCC1>CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)O)cc1C12CC3CC(CC(C3)C1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-429d4cda5f5a43799ceb5fbb3c399100 | C=CCOC(=O)c1ccc(OC(=O)c2ccc(O[Si](C)(C)C(C)(C)C)c(C34CC5CC(CC(C5)C3)C4)c2)nc1>>CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)Oc2ccc(C(=O)O)cn2)cc1C12CC3CC(CC(C3)C1)C2 | C(CCC)[SnH](CCCC)CCCC.C12(CC3CC(CC(C1)C3)C2)C=2C=C(C(=O)OC3=NC=C(C(=O)OCC=C)C=C3)C=CC2O[Si](C)(C)C(C)(C)C.Cl>>C12(CC3CC(CC(C1)C3)C2)C=2C=C(C(=O)OC3=NC=C(C(=O)O)C=C3)C=CC2O[Si](C)(C)C(C)(C)C | C=CC[O:22][C:20]([c:19]1[cH:18][cH:17][c:16]([O:15][C:13]([c:12]2[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:26]([C:27]34[CH2:28][CH:29]5[CH2:30][CH:31]([CH2:32][CH:33]([CH2:34]5)[CH2:35]3)[CH2:36]4)[cH:25]2)=[O:14])[n:24][cH:23]1)=[O:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3... | C=CCOC(=O)c1ccc(OC(=O)c2ccc(O[Si](C)(C)C(C)(C)C)c(C34CC5CC(CC(C5)C3)C4)c2)nc1 | CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)Oc2ccc(C(=O)O)cn2)cc1C12CC3CC(CC(C3)C1)C2 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | ed269ca55aec5bff4b12be2d0b3de5ee7266c084a9f8e361574d4479e760fc9a | 9247ae44385773b8f4b33d9727786bed234278529a98c511521a502ffe365790 | O=C(Oc1ccccn1)c1cccc(C23CC4CC(CC(C4)C2)C3)c1 | C=C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 22.7 | [{"value": 22.7, "product": "C12(CC3CC(CC(C1)C3)C2)C=2C=C(C(=O)OC3=NC=C(C(=O)O)C=C3)C=CC2O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 100 mg of this ester were dissolved in 5 ml of absolute tetrahydrofuran and treated under argon with 104 mg of tetrakis-(triphenylphosphine)-palladium and 61 mg of tributyltin hydride. After stirring at room temperature for 30 min., the reaction mixture was poured on to ice/saturated ammonium chloride solution, acidifi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Allyl | Carboxylic acid | null | null | c1ccccc1.c1ccncc1.C1C2CC3CC1CC(C2)C3 | Other | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1 | null | 0.5 | C=CCOC(=O)c1ccc(OC(=O)c2ccc(O[Si](C)(C)C(C)(C)C)c(C34CC5CC(CC(C5)C3)C4)c2)nc1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1>CC(C)(C)[Si](C)(C)Oc1ccc(C(=O)Oc2ccc(C(=O)O)cn2)cc1C12CC3CC(CC(C3)C1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d998b7fe2794f36a0da66f08e6c5190 | CN=C=O.C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3>>CNC(=O)[O-].C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3 | C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C.CN=C=O>>C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C.CNC([O-])=O | [CH3:1][N:2]=[C:3]=[O:4].[OH:5][C@@H:8]1[C@H:7]([CH3:6])[C@@H:22]2[CH2:21][CH2:20][C@@H:18]([CH3:19])[C@@H:17]3[CH2:16][CH2:15][C:13]4([CH3:14])[O:12][C@@H:11]([O:10]1)[C@@:23]32[O:24][O:25]4>>[CH3:1][NH:2][C:3](=[O:4])[O-:5].[CH3:6][C@H:7]1[C@@H:8]([OH:9])[O:10][C@@H:11]2[O:12][C:13]3([CH3:14])[CH2:15][CH2:16][C@H:17]... | CN=C=O.C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3 | CNC(=O)[O-].C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3 | null | null | C(Cl)Cl | Acylation | OtherReaction | 7daf814dac15ef7d283e5348fdd3c8b2fc54980ade315ce55b0bdc7532f8d52b | 324b9b0d41dbdbd0410a7ca73b88d13aa195b02e8c8e5363c25d974e101242aa | C1C[C@@H]2CCC3OO[C@@]24[C@@H](C1)CCO[C@@H]4O3 | [#8:1]-[C:2]-[#8:3]-[C@H;D3;+0:4](-[OH;D1;+0:5])-[C:6](-[C;D1;H3:7])-[C:8].[C;D1;H3:9]-[N;H0;D2;+0:10]=[C;H0;D2;+0:11]=[O;D1;H0:12]>>[#8:1]-[C:2]-[#8:3]-[C@H;D3;+0:4](-[O;D1;H1:13])-[C:6](-[C;D1;H3:7])-[C:8].[C;D1;H3:9]-[NH;D2;+0:10]-[C;H0;D3;+0:11](-[O-;H0;D1:5])=[O;D1;H0:12] | 121.4 | [{"value": 121.4, "product": "C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C.CNC([O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of dihydroqinghaosu (284 mg, 1 mmol) in dry CH2Cl2 (6 ml) and methyl isocyanate (63 mg, 1.1 mmol) was refluxed for ca. 2 days. The solution was filtered and evaporated in vacuo at 40° C. to give a solid, which was chromatographed on a silica-gel column with petroleumether/AcOEt 8:2. The fraction obtained was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Isocyanate.Secondary alcohol | Carbamic acid.Ether.Secondary alcohol | C1C[C@@H]2CCC3OO[C@@]24[C@@H](C1)CCO[C@@H]4O3 | C1C[C@@H]2CCC3OO[C@@]24[C@@H](C1)CCO[C@@H]4O3 | C1C[C@@H]2CCC3OO[C@@]24[C@@H](C1)CCO[C@@H]4O3 | Other | C(Cl)Cl | null | null | CN=C=O.C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3>C(Cl)Cl>CNC(=O)[O-].C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e14621919a904c08b3c9d56e77154681 | O=C=Nc1cccc([N+](=O)[O-])c1>>O=C([O-])Nc1cccc([N+](=O)[O-])c1 | C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C.[N+](=O)([O-])C=1C=C(C=CC1)N=C=O>>C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C.[N+](=O)([O-])C=1C=C(C=CC1)NC(=O)[O-] | [O:21]=[C:22]=[N:24][c:25]1[cH:26][cH:27][cH:28][c:29]([N+:30](=[O:23])[O-:32])[cH:33]1>>[O:21]=[C:22]([O-:23])[NH:24][c:25]1[cH:26][cH:27][cH:28][c:29]([N+:30](=[O:31])[O-:32])[cH:33]1 | O=C=Nc1cccc([N+](=O)[O-])c1 | O=C([O-])Nc1cccc([N+](=O)[O-])c1 | null | null | null | Functional Group Addition | OtherReaction | 420c7c4fe30cfc3fffb8332defbfeb637efb89651ae26c0575d9d088ab57e86b | 6d26e3011880c7a427aadbc9aa67cdb6ed04eaa3210d938c9f2b8a36bf6fd25a | c1ccccc1 | [O;-;D1;H0:1]-[N+;H0;D3:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]:[c:7](-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;D1;H0:10]):[c:11]>>[O-;H0;D1:3]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:8]-[c:7](:[c:11]):[c:6]:[c:4](-[N+;H0;D3:2](-[O;-;D1;H0:1])=[O;D1;H0:12]):[c:5] | null | [] | null | null | null | null | The title compound was similarly prepared from dihydroqinghaosu and m-nitrophenyl isocyanate as Example 3.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Isocyanate | Carbamic acid.Nitro group | null | null | c1ccccc1 | Other | null | null | null | O=C=Nc1cccc([N+](=O)[O-])c1>>O=C([O-])Nc1cccc([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0029680d3ec4bf2ada8460d535c1585 | CN(C)Cc1ccc(C2CCC(=O)CC2)cc1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1 | CN(C)CC1=CC=C(C=C1)C1CCC(CC1)=O.[BH4-].[Na+]>>CN(C)CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([CH:9]2[CH2:10][CH2:11][C:12](=[O:13])[CH2:14][CH2:15]2)[cH:16][cH:17]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:14][CH2:15]2)[cH:16][cH:17]1 | CN(C)Cc1ccc(C2CCC(=O)CC2)cc1 | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 2851cada23ce4ae5bca04d1ef48c1473fe285273d9a82803d040df273fff8e79 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C2CCCCC2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6]>>[C:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6] | null | [] | null | null | null | null | To a solution of 11.1 g (0.048 mol) of 4-(4-dimethylaminomethylphenyl)-cyclohexanone in 100 ml of absolute methanol, which has been cooled to -10° C., is added 1.82 g (0.048 mol) of sodium borohydride in batches with stirring. The reaction mixture is allowed to react for 1.5 hours at ambient temperature and then evapor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | null | CO | null | null | CN(C)Cc1ccc(C2CCC(=O)CC2)cc1>CO>CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-106a0c8f6a4340dd99e577e214caf696 | CN(C)Cc1ccc(C2CCC(=O)CC2)cc1>>CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1 | C(C)O.OO.CN(C)CC1=CC=C(C=C1)C1CCC(CC1)=O.C(C)(CC)[BH-](C(C)CC)C(C)CC.[Li+]>>CN(C)CC1=CC=C(C=C1)[C@H]1CC[C@H](CC1)O | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([CH:9]2[CH2:10][CH2:11][C:12](=[O:13])[CH2:14][CH2:15]2)[cH:16][cH:17]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@@H:12]([OH:13])[CH2:14][CH2:15]2)[cH:16][cH:17]1 | CN(C)Cc1ccc(C2CCC(=O)CC2)cc1 | CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 2851cada23ce4ae5bca04d1ef48c1473fe285273d9a82803d040df273fff8e79 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C2CCCCC2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6]>>[C:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6] | null | [] | null | null | 10 | MINUTE | 50 ml (0.05 mol) of a 1 molar solution of lithium tri-sec.-butyl-borohydride in absolute tetrahydrofuran are diluted with 100 ml of absolute tetrahydrofuran under a nitrogen atmosphere and then, at -65° C. to -70° C., with stirring and within 10 minutes, a solution of 5.8 g (0.025 mol) of 4-(4-dimethylaminomethylphenyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | null | O1CCCC1 | null | 0.166667 | CN(C)Cc1ccc(C2CCC(=O)CC2)cc1>O1CCCC1>CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-59ad5f10a39944bab640d9fbd6671548 | O=C1CCC(c2ccccc2)CC1>>OC1CCC(c2ccccc2)CC1 | C1(=CC=CC=C1)C1CCC(CC1)=O.[BH4-].[Na+]>>C1(=CC=CC=C1)C1CCC(CC1)O | [O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13]1>>[OH:1][CH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13]1 | O=C1CCC(c2ccccc2)CC1 | OC1CCC(c2ccccc2)CC1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 2851cada23ce4ae5bca04d1ef48c1473fe285273d9a82803d040df273fff8e79 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C2CCCCC2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6] | 66.2 | [{"value": 66.0, "product": "C1(=CC=CC=C1)C1CCC(CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "C1(=CC=CC=C1)C1CCC(CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 31.4 g (0.18 mol) of 4-phenylcyclohexanone in 500 ml of absolute methanol, which is cooled to -10° C., are added 6.8 g (0.18 mol) of sodium borohydride in batches with stirring. The reaction mixture is allowed to react for 0.5 hours at -10° C. and for 3 hours at ambient temperature and then evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | null | CO | null | null | O=C1CCC(c2ccccc2)CC1>CO>OC1CCC(c2ccccc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9d8b4bad4cfc4f6f9993dde1eca90539 | CC(=O)OC(C)=O.OC1CCC(c2ccccc2)CC1>>CC(=O)OC1CCC(c2ccccc2)CC1 | C1(=CC=CC=C1)C1CCC(CC1)O.CC(=O)OC(=O)C>>C(C)(=O)OC1CCC(CC1)C1=CC=CC=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1>>[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1 | CC(=O)OC(C)=O.OC1CCC(c2ccccc2)CC1 | CC(=O)OC1CCC(c2ccccc2)CC1 | null | CN(C1=CC=NC=C1)C | C(C)N(CC)CC | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | c1ccc(C2CCCCC2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7] | 92 | [{"value": 92.0, "product": "C(C)(=O)OC1CCC(CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.6, "product": "C(C)(=O)OC1CCC(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 20.3 g (0.115 mol) of 4-phenylcyclohexanol, 14.2 ml (0.15 mol) of acetanhydride and 29 ml of triethylamine are added, with stirring and at ambient temperature, 2.3 g (0.02 mol) of 4-dimethylaminopyridine, a clear solution being produced in an exothermic reaction. This is heated to 80° C. for 3 hours and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | C1CCCCC1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(C)N(CC)CC | null | null | CC(=O)OC(C)=O.OC1CCC(c2ccccc2)CC1>CN(C1=CC=NC=C1)C.C(C)N(CC)CC>CC(=O)OC1CCC(c2ccccc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-989f1c45e316471198b7f2d873102bdb | C=O.CC(=O)OC1CCC(c2ccccc2)CC1.Cl>>CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1 | C(Cl)Cl.C(C)(=O)OC1CCC(CC1)C1=CC=CC=C1.C=O.Cl>>C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCl | O=[CH2:13].[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:15][cH:16]2)[CH2:17][CH2:18]1.[ClH:14]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([c:9]2[cH:10][cH:11][c:12]([CH2:13][Cl:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | C=O.CC(=O)OC1CCC(c2ccccc2)CC1.Cl | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1 | null | [Cl-].[Zn+2].[Cl-] | null | C-C Coupling | OtherReaction | 8fe6a9acd6712eceb303cec1f37294821c7a3812792483df6fdf1f25e3f9d768 | 9040382df3c5c738c70f57f2da5c03057ad8ce8a09c32bd12c78827f9fd1b464 | c1ccc(C2CCCCC2)cc1 | O=[CH2;D1;+0:1].[ClH;D0;+0:2].[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[Cl;H0;D1;+0:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[c:4]:[c:3]):[c:6]:[c:7] | null | [] | null | null | 2.5 | HOUR | A solution of 24.3 g (0.11 mol) of O-acetyl-4-phenylcyclohexanol in 1300 ml of methylene chloride is combined with 26.0 g (0.86 mol) of paraformaldehyde and 26.0 g (0.19 mol) of zinc chloride. Hydrogen chloride is introduced into this suspension, with stirring, for 2.5 hours, whilst the temperature rises to about 30° C... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary halide | c1ccccc1 | c1ccccc1 | C1CCCCC1.c1ccccc1 | HO- | [Cl-].[Zn+2].[Cl-] | null | 2.5 | C=O.CC(=O)OC1CCC(c2ccccc2)CC1.Cl>[Cl-].[Zn+2].[Cl-]>CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fe8da988a6f64ed0968009c91353edde | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)c1ccc(Cl)cc1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)c3ccc(Cl)cc3)CC2)cc1 | [OH-].[Na+].CN(C)CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O.C(C)N(CC)CC.ClC1=CC=C(C(=O)Cl)C=C1>>ClC1=CC=C(C(=O)O[C@@H]2CC[C@H](CC2)C2=CC=C(C=C2)CN(C)C)C=C1 | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:23][CH2:24]2)[cH:25][cH:26]1.Cl[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([O:13][C:14](=[O:15])[c:16]3[cH:17][cH... | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)c1ccc(Cl)cc1 | CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)c3ccc(Cl)cc3)CC2)cc1 | null | null | C(Cl)Cl.O | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(O[C@H]1CC[C@H](c2ccccc2)CC1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9] | null | [] | null | null | null | null | A solution of 1.0 g (0.0043 mol) of trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and 0.6 ml of triethylamine in 50 ml of methylene chloride is combined, dropwise, with 0.75 g (0.0043 mol) of 4-chlorobenzoylchloride, with stirring, and refluxed for 3 hours. After cooling, 50 ml of water are added, the mixture is a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HCl | C(Cl)Cl.O | null | null | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)c1ccc(Cl)cc1>C(Cl)Cl.O>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)c3ccc(Cl)cc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-98aa976f41dc49e1bd5ec855777b801d | CC(=O)Cl.CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1>>CC(=O)O[C@@H]1CC[C@@H](c2ccc(CN(C)C)cc2)CC1 | CN(C)CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O.C(C)(=O)Cl.C(C)N(CC)CC>>C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C | Cl[C:2]([CH3:1])=[O:3].[OH:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([c:9]2[cH:10][cH:11][c:12]([CH2:13][N:14]([CH3:15])[CH3:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([c:9]2[cH:10][cH:11][c:12]([CH2:13][N:14]([CH3:15])[CH3:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1 | CC(=O)Cl.CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1 | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CN(C)C)cc2)CC1 | null | null | null | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccc(C2CCCCC2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7] | null | [] | null | null | null | null | from trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and acetylchloride/triethylamine. Colourless syrup.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1CCCCC1.c1ccccc1 | HCl | null | null | null | CC(=O)Cl.CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1>>CC(=O)O[C@@H]1CC[C@@H](c2ccc(CN(C)C)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e78195adcc9b4f1e92d9c95ef4fa295b | CCCC(=O)Cl.CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1>>CCCC(=O)O[C@@H]1CC[C@@H](c2ccc(CN(C)C)cc2)CC1 | CN(C)CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O.C(CCC)(=O)Cl.C(C)N(CC)CC>>C(CCC)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[OH:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([c:11]2[cH:12][cH:13][c:14]([CH2:15][N:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[O:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([c:11]2[cH:12][cH:13][c:14]([CH2:15][N:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)[CH... | CCCC(=O)Cl.CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1 | CCCC(=O)O[C@@H]1CC[C@@H](c2ccc(CN(C)C)cc2)CC1 | null | null | null | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccc(C2CCCCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-[C:8] | null | [] | null | null | null | null | from trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and butyric acid chloride/triethylamine. Colourless oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1CCCCC1.c1ccccc1 | HCl | null | null | null | CCCC(=O)Cl.CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1>>CCCC(=O)O[C@@H]1CC[C@@H](c2ccc(CN(C)C)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7f6c0cb8ddf545bda5b486eb8435608e | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)C1CC1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)C3CC3)CC2)cc1 | CN(C)CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O.C1(CC1)C(=O)Cl.C(C)N(CC)CC>>C1(CC1)C(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:19][CH2:20]2)[cH:21][cH:22]1.Cl[C:14](=[O:15])[CH:16]1[CH2:17][CH2:18]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([O:13][C:14](=[O:15])[CH:16]3[CH2:17][CH2:18]3)[CH2:19][CH2:20]2... | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)C1CC1 | CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)C3CC3)CC2)cc1 | null | null | null | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(O[C@H]1CC[C@H](c2ccccc2)CC1)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1)-[C:9] | null | [] | null | null | null | null | from trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and cyclopropane carboxylic acid chloride/triethylamine. Colourless wax.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CCCCC1.C1CC1 | HCl | null | null | null | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)C1CC1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)C3CC3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-65d0d248651b4777b9672b8046a54da0 | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)C1CCCCC1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)C3CCCCC3)CC2)cc1 | CN(C)CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O.C1(CCCCC1)C(=O)Cl.C(C)N(CC)CC>>C1(CCCCC1)C(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:22][CH2:23]2)[cH:24][cH:25]1.Cl[C:14](=[O:15])[CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([O:13][C:14](=[O:15])[CH:16]3[CH2:17][CH... | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)C1CCCCC1 | CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)C3CCCCC3)CC2)cc1 | null | null | null | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(O[C@H]1CC[C@H](c2ccccc2)CC1)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5])-[C:9] | null | [] | null | null | null | null | from trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and cyclohexane carboxylic acid chloride/triethylamine. White crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CCCCC1.C1CCCCC1 | HCl | null | null | null | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)C1CCCCC1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)C3CCCCC3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fb382a38ecde4b3498d73cf8d48e3315 | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)CC=Cc1ccccc1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)CC=Cc3ccccc3)CC2)cc1 | CN(C)CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)O.C1(=CC=CC=C1)C=CCC(=O)Cl.C(C)N(CC)CC>>C1(=CC=CC=C1)C=CCC(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:25][CH2:26]2)[cH:27][cH:28]1.Cl[C:14](=[O:15])[CH2:16][CH:17]=[CH:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([O:13][C:14](=[O:15])[C... | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)CC=Cc1ccccc1 | CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)CC=Cc3ccccc3)CC2)cc1 | null | null | null | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(CC=Cc1ccccc1)O[C@H]1CC[C@H](c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]=[C:5]-[c:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]=[C:5]-[c:6])-[C:10] | null | [] | null | null | null | null | from trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and 4-phenyl-3-butenoic acid chloride/triethylamine. White crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HCl | null | null | null | CN(C)Cc1ccc([C@@H]2CC[C@@H](O)CC2)cc1.O=C(Cl)CC=Cc1ccccc1>>CN(C)Cc1ccc([C@@H]2CC[C@@H](OC(=O)CC=Cc3ccccc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-558c9a0ee99e4a3bb4ba4d9621782c8f | CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1.O=C(Cl)CC=Cc1ccccc1>>CN(C)Cc1ccc([C@@H]2CC[C@H](OC(=O)CC=Cc3ccccc3)CC2)cc1 | CN(C)CC1=CC=C(C=C1)[C@H]1CC[C@H](CC1)O.C1(=CC=CC=C1)C=CCC(=O)Cl.C(C)N(CC)CC>>C1(=CC=CC=C1)C=CCC(=O)O[C@@H]1CC[C@@H](CC1)C1=CC=C(C=C1)CN(C)C | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@@H:12]([OH:13])[CH2:25][CH2:26]2)[cH:27][cH:28]1.Cl[C:14](=[O:15])[CH2:16][CH:17]=[CH:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@@H:12]([O:13][C:14](=[O:15])... | CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1.O=C(Cl)CC=Cc1ccccc1 | CN(C)Cc1ccc([C@@H]2CC[C@H](OC(=O)CC=Cc3ccccc3)CC2)cc1 | null | null | null | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(CC=Cc1ccccc1)O[C@H]1CC[C@@H](c2ccccc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]=[C:5]-[c:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]=[C:5]-[c:6])-[C:10] | null | [] | null | null | null | null | from cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol and 4-phenyl-3-butenoic acid chloride/triethylamine. White crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HCl | null | null | null | CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1.O=C(Cl)CC=Cc1ccccc1>>CN(C)Cc1ccc([C@@H]2CC[C@H](OC(=O)CC=Cc3ccccc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46545033cfa54ccfbfeb9970eade577f | CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1.O=C(Cl)c1ccc(Cl)cc1>>CN(C)Cc1ccc([C@@H]2CC[C@H](OC(=O)c3ccc(Cl)cc3)CC2)cc1 | ClC1=CC=C(C(=O)Cl)C=C1.CN(C)CC1=CC=C(C=C1)[C@H]1CC[C@H](CC1)O.C(C)N(CC)CC.CN(C)C1=NC=CC=C1.[OH-].[Na+]>>ClC1=CC=C(C(=O)O[C@@H]2CC[C@@H](CC2)C2=CC=C(C=C2)CN(C)C)C=C1 | [CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@@H:12]([OH:13])[CH2:23][CH2:24]2)[cH:25][cH:26]1.Cl[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C@H:9]2[CH2:10][CH2:11][C@@H:12]([O:13][C:14](=[O:15])[c:16]3[cH:17][... | CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1.O=C(Cl)c1ccc(Cl)cc1 | CN(C)Cc1ccc([C@@H]2CC[C@H](OC(=O)c3ccc(Cl)cc3)CC2)cc1 | null | null | C(Cl)Cl.O | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(O[C@H]1CC[C@@H](c2ccccc2)CC1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9] | null | [] | null | null | 12 | HOUR | 0.24 g (0.001 mol) of cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol, 0,34 ml (0.0025 mol) of triethylamine and 0.12 g (0.001 mol) of dimethylaminopyridine are dissolved in 20 ml of methylene chloride, mixed with 0.175 g (0.001 mol) of 4-chlorobenzoylchloride and stirred for 12 hours at ambient temperature. The react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HCl | C(Cl)Cl.O | null | 12 | CN(C)Cc1ccc([C@@H]2CC[C@H](O)CC2)cc1.O=C(Cl)c1ccc(Cl)cc1>C(Cl)Cl.O>CN(C)Cc1ccc([C@@H]2CC[C@H](OC(=O)c3ccc(Cl)cc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5a8195f23794884af3a23a8c8f6148d | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1.CCNCC>>CCN(CC)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 | O.C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCl.C([O-])([O-])=O.[K+].[K+].C(C)NCC>>C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(CC)CC | Cl[CH2:6][c:7]1[cH:8][cH:9][c:10]([C@H:11]2[CH2:12][CH2:13][C@H:14]([O:15][C:16]([CH3:17])=[O:18])[CH2:19][CH2:20]2)[cH:21][cH:22]1.[CH3:1][CH2:2][NH:3][CH2:4][CH3:5]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([C@H:11]2[CH2:12][CH2:13][C@H:14]([O:15][C:16]([CH3:17])=[O:18])[CH2:19][CH2:20]2)[cH... | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1.CCNCC | CCN(CC)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C;D1;H3:9]>>[C;D1;H3:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C;D1;H3:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 50 | CELSIUS | null | null | A solution of 1 g (3.75 mmol) of trans-O-acetyl-4-(4-chloromethylphenyl)-cyclohexanol in 10 ml of dimethylformamide is mixed with 0.52 g (3.75 mmol) of potassium carbonate and 0.27 g (3.75 mmol) of diethylamine. This mixture is heated to 50° C. for 6 hours with stirring, then water is added and the mixture is extracted... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CCCCC1 | HCl | CN(C=O)C | 50 | null | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1.CCNCC>CN(C=O)C>CCN(CC)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f2d5dfa3dcc34983a499f39832ce5301 | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1.CCCNCCC>>CCCN(CCC)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 | C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCl.C(CC)NCCC>>C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(CCC)CCC | Cl[CH2:8][c:9]1[cH:10][cH:11][c:12]([C@H:13]2[CH2:14][CH2:15][C@H:16]([O:17][C:18]([CH3:19])=[O:20])[CH2:21][CH2:22]2)[cH:23][cH:24]1.[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH3:7]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH2:8][c:9]1[cH:10][cH:11][c:12]([C@H:13]2[CH2:14][CH2:15][C@H:16]([O:17][C:18]([CH3:1... | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1.CCCNCCC | CCCN(CCC)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | from trans-O-acetyl-4-(4-chloromethylphenyl)-cyclohexanol and dipropylamine. Colourless oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CCCCC1 | HCl | null | null | null | CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1.CCCNCCC>>CCCN(CCC)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c57a2e6edd64e5e962d5636e0b02f36 | C=CCNCC=C.CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1>>C=CCN(CC=C)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 | C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCl.C(C=C)NCC=C>>C(C)(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(CC=C)CC=C | [CH2:1]=[CH:2][CH2:3][NH:4][CH2:5][CH:6]=[CH2:7].Cl[CH2:8][c:9]1[cH:10][cH:11][c:12]([C@H:13]2[CH2:14][CH2:15][C@H:16]([O:17][C:18]([CH3:19])=[O:20])[CH2:21][CH2:22]2)[cH:23][cH:24]1>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[CH2:8][c:9]1[cH:10][cH:11][c:12]([C@H:13]2[CH2:14][CH2:15][C@H:16]([O:17][C:18]([CH3:1... | C=CCNCC=C.CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1 | C=CCN(CC=C)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H2:5]=[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]=[C;D1;H2:11]>>[C;D1;H2:5]=[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10]=[C;D1;H2:11])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | from trans-O-acetyl-4-(4-chloromethylphenyl)-cyclohexanol and diallylamine. Colourless oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CCCCC1 | HCl | null | null | null | C=CCNCC=C.CC(=O)O[C@@H]1CC[C@@H](c2ccc(CCl)cc2)CC1>>C=CCN(CC=C)Cc1ccc([C@@H]2CC[C@@H](OC(C)=O)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf6dff211f2249548afbc224153b66a4 | Cl>>Cl | ClC1=CC=C(C=C1)CC(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C.Cl>>Cl.ClC1=CC=C(C=C1)CC(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C | [ClH:28]>>[ClH:28] | Cl | Cl | null | null | C(C)(C)O.C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 1 | HOUR | A solution of 0.39 g (0.001 mol) of trans-O-(4-chlorophenylacetyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol in 10 ml of diethyl ether is combined at ambient temperature, with stirring, with a 1.5 times equimolar amount of hydrogen chloride in isopropanol added dropwise. The precipitate formed is left for 1 hour at ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O.C(C)OCC | null | 1 | Cl>C(C)(C)O.C(C)OCC>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-55aacc7a80b0419cab9d2c65fa6adadb | O=C(O)C(O)C(O)C(=O)O>>O=C([O-])C(O)C(O)C(=O)[O-] | C(C(O)C(O)C(=O)O)(=O)O.ClC1=CC=C(C=C1)CC(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C.C(C)OCC>>ClC1=CC=C(C=C1)CC(=O)O[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CN(C)C.C(=O)([O-])C(O)C(O)C(=O)[O-] | [O:28]=[C:29]([OH:30])[CH:31]([OH:32])[CH:33]([OH:34])[C:35](=[O:36])[OH:37]>>[O:28]=[C:29]([O-:30])[CH:31]([OH:32])[CH:33]([OH:34])[C:35](=[O:36])[O-:37] | O=C(O)C(O)C(O)C(=O)O | O=C([O-])C(O)C(O)C(=O)[O-] | null | null | C(C)O | Oxidation | OtherReaction | 4af04878ecd22d61c6d7d46db52e672904d5e72408231940a5cea872324a16a2 | 4e878a1fdc9370141a3ed00507bdfaa037f36d163bb15c5076375a9835c80b8f | null | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[O-;H0;D1:3]-[C:2](=[O;D1;H0:1])-[C:4]-[C:5]-[C:6](-[O-;H0;D1:8])=[O;D1;H0:7] | null | [] | null | null | 8 | HOUR | First 0.15 g (0.001 mol) of anhydrous tartaric acid and then 0.39 g (0.001 mol) of trans-O-(4-chlorophenylacetyl)-4-(4-dimethylaminomethylphenyl)-cyclohexanol are dissolved in 7 ml of absolute ethanol. Diethyl ether is then added to the clear solution until it becomes slightly cloudy and it is then left to stand for 8 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | null | null | null | null | null | C(C)O | null | 8 | O=C(O)C(O)C(O)C(=O)O>C(C)O>O=C([O-])C(O)C(O)C(=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b8ac393b893c42cfb6d34015ef8c6939 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | O.BrCC1=CC=C(C#N)C=C1.[H-].[Na+].N1C(NCC1)=O>>O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23]1.[NH:8]1[CH2:9][CH2:15][NH:11][C:21]1=[O:22]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]3)[C:21]2=[O:22])[cH:23][cH:24]1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1 | N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 39571f641692bae0ab2e4fb7e56baf0a046bbe68e5d15065d8f936b61702d85c | 04064b000c1f037cb6379c4a9b891971302bcd094d2302ea56061b3b37327222 | O=C1N(Cc2ccccc2)CCN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1>>[C:11]-[c:12](:[c:13]):[cH;D2;+0:8]:[c:14]:[c:15]-[C:16]-[N;H0;D3;+0:7]1-[C:17]-[CH2;D2;+0:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:6]-1=[O;D1;H0:5] | null | [] | null | null | 1 | HOUR | To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea.Nitrile | C1CNCN1 | C1C[NH]C[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | Br- | CN(C=O)C | null | 1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>CN(C=O)C>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d53ccc1fdb224edc9a97f3bf1af38c7c | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O>>CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 | NC(=O)N.CN(C1=CC=C(C=C1)C(C(=O)C1=CC=CC=C1)O)C>>CN(C1=CC=C(C=C1)C=1NC(NC1C1=CC=CC=C1)=O)C | O=[C:13]([CH:8](O)[c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:21][cH:20]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[NH2:9][C:10](=[O:11])[NH2:12]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[nH:9][c:10](=[O:11])[nH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1 | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O | CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 7a04490902783a9d1d6099ad78b95538301d0ef7b8b6cc364284d393dbdf37cd | 19da97726e6dc44d537eff971a50046c3e80ca62fdecca0b64533a3c10927d47 | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | O-[CH;D3;+0:1](-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[NH2;D1;+0:13]-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[O;D1;H0:16]>>[O;D1;H0:16]=[c;H0;D3;+0:14]1:[nH;D2;+0:13]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:... | null | [] | 120 | CELSIUS | 2 | HOUR | To acetic acid (2 mL) was added urea (0.6 g, 10 mmol) and 2-(4-dimethylaminophenyl)-2-hydroxy-1-phenylethanone (2.6 g, 10 mmol). After stirring for 2 hours at 120° C., the reaction was cooled to ambient temperature. The resulting solid was filtered, washed with ether, and dried in vacuo to give 4-(4-dimethylaminophenyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Urea.Secondary alcohol | null | null | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.c1ccccc1 | HO- | C(C)(=O)O | 120 | 2 | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O>C(C)(=O)O>CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b724f3ac05e046b9b06047e61353e43e | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.BrCC=1C=C(C#N)C=CC1.[H-].[Na+]>>C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:27]1.[nH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[nH:24][c:25]1=[O:26]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:1... | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chroma... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C=O)C | null | null | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C=O)C>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5dd855de65c9493aa839d921f58ac95c | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | Cl.C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.[H-].[Na+].BrCC=1C=C(C(=O)OC)C=CC1>>COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:29]1.[nH:11]1[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[nH:26][c:27]1=[O:28]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][n:11]2[c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:... | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 25 | [{"value": 25.0, "product": "COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DM... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C)C=O | 50 | 0.5 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C)C=O>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-786127000a804395a2a606287fdb5b82 | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O.BrCC1=CC=C2C=CC(=CC2=C1)C#N>>C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O | Br[CH2:25][c:26]1[cH:27][cH:28][c:29]2[cH:30][cH:31][c:32]([C:33]#[N:34])[cH:35][c:36]2[cH:37]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[nH:24][c:38]2=[O:39])[cH:40]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6... | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1n(Cc2ccccc2)c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:1=[O;D1;H0:13] | null | [] | null | null | null | null | In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s, 1), 7... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.c1c[nH]cn1 | HBr | null | null | null | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-308160af0fe341559cc3cb76dcacfde8 | C=CC(=O)OC.CCCN(CCC)C1CCc2cc(Br)ccc2C1>>CCCN(CCC)C1CCc2cc(/C=C/C(=O)OC)ccc2C1 | BrC=1C=C2CCC(CC2=CC1)N(CCC)CCC.C(C=C)(=O)OC.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C(C)N(CC)CC>>COC(\C=C\C=1C=C2CCC(CC2=CC1)N(CCC)CCC)=O | [CH2:14]=[CH:15][C:16](=[O:17])[O:18][CH3:19].Br[c:13]1[cH:12][c:11]2[c:22]([cH:21][cH:20]1)[CH2:23][CH:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9][CH2:10]2>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH:8]1[CH2:9][CH2:10][c:11]2[cH:12][c:13](/[CH:14]=[CH:15]/[C:16](=[O:17])[O:18][CH3:19])[cH:20... | C=CC(=O)OC.CCCN(CCC)C1CCc2cc(Br)ccc2C1 | CCCN(CCC)C1CCc2cc(/C=C/C(=O)OC)ccc2C1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C=O)C.O | C-C Coupling | Heck terminal vinyl | 7d54f98603f982a766802e8a50fd3c154a20a496d1d88bfc154a88f37c1a4dfc | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccc2c(c1)CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]=[CH2;D1;+0:11]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])/[C:10]=[CH;D2;+0:11]/[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 28.5 | [{"value": 28.5, "product": "COC(\\C=C\\C=1C=C2CCC(CC2=CC1)N(CCC)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.1 g (0.01 mol) of 6-bromo-2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphthalene are dissolved in 50 ml of dimethylformamide. There are added in succession to that solution 0.94 g (0.011 mol) of methyl acrylate, 22.4 mg (0.1 mmol) of palladium acetate, 121 mg (0.4 mmol) of tri-ortho-tolylphosphine and 1.6 ml (0.011 mol)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C.O | null | null | C=CC(=O)OC.CCCN(CCC)C1CCc2cc(Br)ccc2C1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C.O>CCCN(CCC)C1CCc2cc(/C=C/C(=O)OC)ccc2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b4fd402e735143d2ba1df2c8a9a0fe8f | BrCc1ccccc1.COC(=O)c1ccc(O)cc1O>>COC(=O)c1ccc(OCc2ccccc2)cc1O | OC1=C(C(=O)OC)C=CC(=C1)O.C(=O)([O-])[O-].[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC1=CC(=C(C(=O)OC)C=C1)O | Br[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:17][c:18]1[OH:19]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[OH:19] | BrCc1ccccc1.COC(=O)c1ccc(O)cc1O | COC(=O)c1ccc(OCc2ccccc2)cc1O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | null | null | To a stirred, 0° C. solution of methyl 2,4-dihydroxybenzoate (50 g, 300 mmol) in acetone (1000 mL) was added K2CO3 (150 g, 1000 mmol) and benzyl bromide (330 mmol, 39 mL). The solution was allowed to warm to ambient temperature over 48 h. The reaction solution was filtered through celite and the acetone solution stripp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | null | BrCc1ccccc1.COC(=O)c1ccc(O)cc1O>CC(=O)C>COC(=O)c1ccc(OCc2ccccc2)cc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c4670bc17b3d4dddbc6d0f72787fbc62 | CI.COC(=O)c1ccc(OCc2ccccc2)cc1O>>COC(=O)c1ccc(OCc2ccccc2)cc1OC | C(C1=CC=CC=C1)OC1=CC(=C(C(=O)OC)C=C1)O.[H-].[Na+].CI>>C(C1=CC=CC=C1)OC1=CC(=C(C(=O)OC)C=C1)OC | I[CH3:20].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[OH:19]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]1[O:19][CH3:20] | CI.COC(=O)c1ccc(OCc2ccccc2)cc1O | COC(=O)c1ccc(OCc2ccccc2)cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(COc2ccccc2)cc1 | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[O;H0;D2;+0:7]-[CH3;D1;+0:1]):[c:8] | null | [] | null | null | null | null | To a stirred, 0° C. solution of methyl 4-benzyloxy-2-hydroxybenzoate (12 g, 46 mmol) in DMF (150 mL) was added NaH (2.76 g, 69 mmol) and methyl iodide (7.2 mL, 116 mmol). The solution was allowed to warm to ambient temperature overnight with stirring. The reaction mixture was poured onto ice and the resulting aqueous s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HI | CN(C)C=O | null | null | CI.COC(=O)c1ccc(OCc2ccccc2)cc1O>CN(C)C=O>COC(=O)c1ccc(OCc2ccccc2)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c1656a56b0b84177904d3a04b5264874 | COC(=O)c1ccc(O)cc1OC>>COc1cc(O)ccc1C(=O)O | Cl.OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>OC1=CC(=C(C(=O)O)C=C1)OC | C[O:12][C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([OH:6])[cH:7][cH:8]1)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[cH:7][cH:8][c:9]1[C:10](=[O:11])[OH:12] | COC(=O)c1ccc(O)cc1OC | COc1cc(O)ccc1C(=O)O | null | null | C1CCOC1 | 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 | 24 | HOUR | To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (11 g, 60 mmol) in THF:H2O (100 mL:10 mL) was added LiOH.H2O (3 g, 71 mmol). The solution was stirred over 24 h and then made slightly acidic (pH 5) with 10% HCl (approx 15 mL). The reaction solution was extracted with CH2Cl2 (3×50 mL). The organic phase was d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C1CCOC1 | null | 24 | COC(=O)c1ccc(O)cc1OC>C1CCOC1>COc1cc(O)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48df0370b6c1448ea65c1fd6355a24c2 | COC(=O)c1ccc(O)cc1OC>>COC(=O)c1cc(F)c(O)cc1OC | OC1=CC(=C(C(=O)OC)C=C1)OC.[O-]S(=O)(=O)C(F)(F)F.ClC=1C=[N+](C=C(C1)Cl)F>>FC=1C(=CC(=C(C(=O)OC)C1)OC)O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:9]([OH:10])[cH:11][c:12]1[O:13][CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([OH:10])[cH:11][c:12]1[O:13][CH3:14] | COC(=O)c1ccc(O)cc1OC | COC(=O)c1cc(F)c(O)cc1OC | null | null | C(Cl)Cl | Functional Group Addition | Aromatic fluorination | 2e63a9b91d60f82a8e59b7c72ed55b9aec048f26be2f5eb9ca65b1b73867743c | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[cH;D2;+0:6]:[c:7](-[O;D1;H1:8]):[c:9]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c;H0;D3;+0:6](-[F;D1;H0:10]):[c:7](-[O;D1;H1:8]):[c:9] | null | [] | null | null | null | null | To a stirred solution of the methyl 4-hydroxy-2-methoxybenzoate (1 g, 5 mmol, from Step 3) in CH2Cl2 (20 mL) was added 3,5-dichloro-1-fluoropyridinium triflate (2.25 g, 6 mmol). The solution was refluxed for 48 h and then cooled to ambient temperature and stripped down under reduced pressure. The crude oil was purified... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(Cl)Cl | null | null | COC(=O)c1ccc(O)cc1OC>C(Cl)Cl>COC(=O)c1cc(F)c(O)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e02459c44114d51802676f652203008 | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.OC1CCOCC1>>COC(=O)c1ccc(OC(=O)C2CCOCC2)cc1OC | O1CCC(CC1)O.N(=NC(=O)OCC)C(=O)OCC.OC1=CC(=C(C(=O)OC)C=C1)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>O1CCC(CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC | CCOC(=O)N=N[C:10](OCC)=[O:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:18][c:19]1[O:20][CH3:21].O[CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[cH:18][c:19]1[O:20][CH3:21] | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.OC1CCOCC1 | COC(=O)c1ccc(OC(=O)C2CCOCC2)cc1OC | null | null | C1CCOC1 | Acylation | OtherReaction | c4890e071978b0b6e02f922f3692bc2e5bc322d64b2e3a6224c530fe8f3a9533 | 99cbc1de664ce75fe7841777e00c71bc93fd4ae2bce0b73a15911d06040840b5 | O=C(Oc1ccccc1)C1CCOCC1 | C-C-O-C(=O)-N=N-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C-C.O-[CH;D3;+0:3]1-[C:4]-[C:5]-[#8:6]-[C:7]-[C:8]-1.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[CH;D3;+0:3]1-[C:4]-[C:5]-[#8:6]-[C:7]-[C:8]-1 | null | [] | 0 | CELSIUS | null | null | To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (713 mg, 3.92 mmol) in dry THF (7.5 mL) was added triphenylphosphine (1.42 g, 5.4 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of tetrahydro-4H-pyran-4-ol (466 mL, 4.90 mmol) and diethyl azodicarboxylate (850 μL, 5.4 mmol) in THF was added dropwi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Secondary alcohol.Aromatic alcohol | Ester | C1CCOCC1 | C1CCOCC1 | c1ccccc1.C1CCOCC1 | HO- | C1CCOC1 | 0 | null | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.OC1CCOCC1>C1CCOC1>COC(=O)c1ccc(OC(=O)C2CCOCC2)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-effcf6e5366a4bfca9b4bac40907f32c | COC(=O)c1ccc(OC(=O)C2CCOCC2)cc1OC>>COc1cc(OC(=O)C2CCOCC2)ccc1C(=O)O | O1CCC(CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>O1CCC(CC1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC | C[O:20][C:18]([c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][cH:16]1)=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][cH:16][c:17]1[C:18](=[O:19])[OH:20] | COC(=O)c1ccc(OC(=O)C2CCOCC2)cc1OC | COc1cc(OC(=O)C2CCOCC2)ccc1C(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)C1CCOCC1 | 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 | [] | 45 | CELSIUS | null | null | To a stirred solution of methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate (369 mg, 1.38 mmol) in THF:H2O (2.5 mL: 0.5 mL) was added LiOH.H2O (116.4 mg, 2.77 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CCOCC1 | Other | C1CCOC1 | 45 | null | COC(=O)c1ccc(OC(=O)C2CCOCC2)cc1OC>C1CCOC1>COc1cc(OC(=O)C2CCOCC2)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d1e263a61084d54a5924ad814549c11 | COC(=O)c1ccc(OC(=O)C2CCc3ccccc32)cc1OC>>COc1cc(OC(=O)C2CCc3ccccc32)ccc1C(=O)O | C1(CCC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>C1(CCC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC | C[O:23][C:21]([c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]32)[cH:18][cH:19]1)=[O:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]32)[cH:18][cH:19][c:20]1[C:21](=[O:22])[OH:23] | COC(=O)c1ccc(OC(=O)C2CCc3ccccc32)cc1OC | COc1cc(OC(=O)C2CCc3ccccc32)ccc1C(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)C1CCc2ccccc21 | 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 | [] | 45 | CELSIUS | null | null | To a stirred solution of methyl 4-(1-indanoyloxy)-2-methoxy-benzoate (125 mg, 0.43 mmol) in THF:H2O (1 mL: 0.2 mL) was added LiOH.H2O (35.2 mg, 0.84 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed throu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CCC2 | Other | C1CCOC1 | 45 | null | COC(=O)c1ccc(OC(=O)C2CCc3ccccc32)cc1OC>C1CCOC1>COc1cc(OC(=O)C2CCc3ccccc32)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e05a7f6ef00b40218847ea8339f5616a | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.O[C@@H]1CCCC[C@H]1c1ccccc1>>COC(=O)c1ccc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)cc1OC | C1(=CC=CC=C1)[C@H]1[C@@H](CCCC1)O.N(=NC(=O)OCC)C(=O)OCC.OC1=CC(=C(C(=O)OC)C=C1)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=CC=C1)[C@@H]1[C@@H](CCCC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC | CCOC(=O)N=N[C:10](OCC)=[O:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:24][c:25]1[O:26][CH3:27].O[C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]1[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:... | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.O[C@@H]1CCCC[C@H]1c1ccccc1 | COC(=O)c1ccc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)cc1OC | null | null | C1CCOC1 | Acylation | OtherReaction | 8e7f7aec30b10cb52f82d427bef98ab15d43a92fc5e2b024cb3b9ec94ed6a028 | 99cbc1de664ce75fe7841777e00c71bc93fd4ae2bce0b73a15911d06040840b5 | O=C(Oc1ccccc1)[C@@H]1CCCC[C@@H]1c1ccccc1 | C-C-O-C(=O)-N=N-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C-C.O-[C@H;D3;+0:3](-[C:4]-[C:5])-[C:6](-[c:7])-[C:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[C:4]-[C@@H;D3;+0:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:6](-[c:7])-[C:8] | null | [] | 0 | CELSIUS | null | null | To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (310 mg, 1.7 mmol) in dry THF (1.25 mL) was added triphenylphosphine (446 mg, 1.7 mmol) and the solution was cooled to 0° C. A 500 mL volume of trans-2-phenyl-1-cyclohexanol (200 mg, 1.35 mmol) and diethyl azodicarboxylate (319 μL, 2.02 mmol) in THF was added ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Secondary alcohol.Aromatic alcohol | Ester | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1.c1ccccc1 | HO- | C1CCOC1 | 0 | null | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.O[C@@H]1CCCC[C@H]1c1ccccc1>C1CCOC1>COC(=O)c1ccc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9cf6d25d3c4e47a1a40710053bd23b71 | COC(=O)c1ccc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)cc1OC>>COc1cc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)ccc1C(=O)O | C1(=CC=CC=C1)[C@@H]1[C@@H](CCCC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>C1(=CC=CC=C1)[C@@H]1[C@@H](CCCC1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC | C[O:26][C:24]([c:23]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7](=[O:8])[C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]2[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1)=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]2[c:15]2[cH:16][cH:17][cH:18][cH... | COC(=O)c1ccc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)cc1OC | COc1cc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)ccc1C(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)[C@@H]1CCCC[C@@H]1c1ccccc1 | 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 | [] | 45 | CELSIUS | null | null | To a stirred solution of methyl 4-(cis-2-phenyl- 1-cyclohexanoyloxy)-2-methoxybenzoate (230 mg, 0.64 mmol) in THF:H2O (5 mL:1 mL) was added LiOH.H2O (113.5 mg, 2.7 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | Other | C1CCOC1 | 45 | null | COC(=O)c1ccc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)cc1OC>C1CCOC1>COc1cc(OC(=O)[C@@H]2CCCC[C@@H]2c2ccccc2)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a806a2b38c847b7b222d09354336829 | CCOC(=O)c1cccnc1C>>Cc1ncccc1CO | Cl.CC1=C(C(=O)OCC)C=CC=N1.[H-].C(C(C)C)[Al+]CC(C)C.[OH-].[Na+]>>OCC=1C(=NC=CC1)C | CCO[C:8]([c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1)=[O:9]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][OH:9] | CCOC(=O)c1cccnc1C | Cc1ncccc1CO | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[C;D1;H3:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | 0 | CELSIUS | 6 | HOUR | To a stirred solution of ethyl 2-methylnicotinate (1.50 g, 9.09 mmol) in freshly distilled THF (100 mL) at 0° C. was added diisobutylaluminum hydride (11.2 mL of a 1.5M solution in toluene, 16.9 mmol). The solution was stirred for 6 h at 0° C. and then warmed to ambient temperature. After 1 h, the solution was cooled i... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | C1(=CC=CC=C1)C.C1CCOC1 | 0 | 6 | CCOC(=O)c1cccnc1C>C1(=CC=CC=C1)C.C1CCOC1>Cc1ncccc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b03b7005ae0f4e16a4358a35620a3d77 | Cc1ncccc1CO.O=S(Cl)Cl>>Cc1ncccc1CCl | OCC=1C(=NC=CC1)C.O=S(Cl)Cl>>ClCC=1C(=NC=CC1)C | O[CH2:8][c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1.O=S(Cl)[Cl:9]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][Cl:9] | Cc1ncccc1CO.O=S(Cl)Cl | Cc1ncccc1CCl | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[C;D1;H3:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1]):[c:4] | null | [] | null | null | 4 | HOUR | To a stirred solution of 3-hydroxymethyl-2-methylpyridine from Step 1 above (1.00 g, 8.13 mmol) in 40 mL of CH2Cl2 at ambient temperature was added SOCl2 (9.0 mL, 123 mmol). The reaction mixture was stirred for 4 hours, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was partitioned... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | 4 | Cc1ncccc1CO.O=S(Cl)Cl>C(Cl)Cl>Cc1ncccc1CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b8dbba8e74ff4118bc3513f530757669 | Cc1ncccc1CCl.O=C(OO)c1cccc(Cl)c1>>Cc1c(CCl)ccc[n+]1[O-] | ClCC=1C(=NC=CC1)C.ClC=1C=C(C(=O)OO)C=CC1>>ClCC=1C(=[N+](C=CC1)[O-])C | [CH3:1][c:2]1[c:3]([CH2:4][Cl:5])[cH:6][cH:7][cH:8][n:9]1.O=C(O[OH:10])c1cccc(Cl)c1>>[CH3:1][c:2]1[c:3]([CH2:4][Cl:5])[cH:6][cH:7][cH:8][n+:9]1[O-:10] | Cc1ncccc1CCl.O=C(OO)c1cccc(Cl)c1 | Cc1c(CCl)ccc[n+]1[O-] | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1cc[nH+]cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c: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] | null | [] | null | null | 1.5 | HOUR | To a stirred solution of 3-chloromethyl-2-methylpyridine from Step 2 above (0.50 g; 3.5 mmol) in CHCl3 (40 mL) was added m-chloroperoxybenzoic acid (1.1 g of 55:45 mCPBA:mCBA; 3.5 mmol). After 1.5 h, TLC analysis indicated complete conversion to a lower Rf product. The solution was extracted with equal volumes of satur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HCl | C(Cl)(Cl)Cl | null | 1.5 | Cc1ncccc1CCl.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>Cc1c(CCl)ccc[n+]1[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c76a22e184294ef893b6fc5df9e611d7 | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.OC1CCOc2ccccc21>>COC(=O)c1ccc(OC(=O)C2CCOc3ccccc32)cc1OC | O1CCC(C2=CC=CC=C12)O.N(=NC(=O)OCC)C(=O)OCC.OC1=CC(=C(C(=O)OC)C=C1)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>O1CCC(C2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC | CCOC(=O)N=N[C:10](OCC)=[O:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:22][c:23]1[O:24][CH3:25].O[CH:12]1[CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[CH:12]2[CH2:13][CH2:14][O:15][c:16]3[cH:17][cH:18][cH:19][c... | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.OC1CCOc2ccccc21 | COC(=O)c1ccc(OC(=O)C2CCOc3ccccc32)cc1OC | null | null | C1CCOC1 | Acylation | OtherReaction | f5703f0bb6d4de4f021493fee785ea9b023c9960545798c80ef6df53e039ff97 | 99cbc1de664ce75fe7841777e00c71bc93fd4ae2bce0b73a15911d06040840b5 | O=C(Oc1ccccc1)C1CCOc2ccccc21 | C-C-O-C(=O)-N=N-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C-C.O-[CH;D3;+0:3]1-[C:4]-[C:5]-[#8:6]-[c:7]:[c:8]-1:[c:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[CH;D3;+0:3]1-[C:4]-[C:5]-[#8:6]-[c:7]:[c:8]-1:[c:9] | null | [] | 0 | CELSIUS | null | null | To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (364 mg, 2.0 mmol) in dry THF (1.25 mL) was added triphenylphosphine (525 mg, 2.0 mmol) and the solution was cooled to 0° C. A 500 mL volume of 4-chromanol (200 mg, 1.33 mmol) and diethyl azodicarboxylate (315 mL, 2.0 mmol) in THF was added dropwise via syring... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Secondary alcohol.Aromatic alcohol | Ester | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2 | HO- | C1CCOC1 | 0 | null | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.OC1CCOc2ccccc21>C1CCOC1>COC(=O)c1ccc(OC(=O)C2CCOc3ccccc32)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-319ce102069542b08b0f9d0be725ed30 | COC(=O)c1ccc(OC(=O)C2CCOc3ccccc32)cc1OC>>COc1cc(OC(=O)C2CCOc3ccccc32)ccc1C(=O)O | O1CCC(C2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>O1CCC(C2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC | C[O:24][C:22]([c:21]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][cH:20]1)=[O:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][CH2:11][O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][cH:20][c:21]1[C:22](=[O... | COC(=O)c1ccc(OC(=O)C2CCOc3ccccc32)cc1OC | COc1cc(OC(=O)C2CCOc3ccccc32)ccc1C(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)C1CCOc2ccccc21 | 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 | [] | 45 | CELSIUS | null | null | To a stirred solution of methyl 4-(4-chromanoyloxy)-2-methoxybenzoate (260 mg, 0.82 mmol) in THF:H2O (4 mL:0.8 mL) was added LiOH.H2O (172 mg, 4.1 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | C1CCOC1 | 45 | null | COC(=O)c1ccc(OC(=O)C2CCOc3ccccc32)cc1OC>C1CCOC1>COc1cc(OC(=O)C2CCOc3ccccc32)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-997799bff2054cbcbc860fbe74d39dc5 | Cc1cnc2c(c1)C(=O)CC(C)(C)C2>>Cc1cnc2c(c1)C(O)CC(C)(C)C2 | CC=1C=NC=2CC(CC(C2C1)=O)(C)C.[BH4-].[Na+]>>CC=1C=NC=2CC(CC(C2C1)O)(C)C | [CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14]2>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[CH:8]([OH:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14]2 | Cc1cnc2c(c1)C(=O)CC(C)(C)C2 | Cc1cnc2c(c1)C(O)CC(C)(C)C2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 82dfffcf6439c6136c0fbf9d7fad4a584d93f84eff1938ce9f23f430baa33464 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1cnc2c(c1)CCCC2 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[c:6](:[#7;a:7]:[c:8]):[c:9]-1:[c:10]>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[c:6](:[#7;a:7]:[c:8]):[c:9]-1:[c:10] | null | [] | null | null | 14 | HOUR | A stirred solution of 5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-one (240 mg, 1.3 mmol) in MeOH (6.5 mL) was cooled to 0° C. under Argon and treated with NaBH4 (48 mg, 1.3 mmol). The reaction was stirred over 14 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crud... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | null | CO | null | 14 | Cc1cnc2c(c1)C(=O)CC(C)(C)C2>CO>Cc1cnc2c(c1)C(O)CC(C)(C)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aaa0ddfbf41e452299afe064a36ec3cd | CCc1ncccc1C(=O)[O-]>>CCc1ncccc1CO | [Li+].C(C)C1=C(C(=O)[O-])C=CC=N1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)C1=NC=CC=C1CO | [O-][C:9]([c:8]1[c:3]([CH2:2][CH3:1])[n:4][cH:5][cH:6][cH:7]1)=[O:10]>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][OH:10] | CCc1ncccc1C(=O)[O-] | CCc1ncccc1CO | null | null | C1CCOC1 | Reduction | OtherReaction | 3ee00ae8302f5a9cabfd43f47c90c2bc696c7c0e2b77ca13873c453d0520692e | c2c13922fe3c9358e6ba38897f2383764691ea247b267e6643408d03716a3879 | c1ccncc1 | [C:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[C;H0;D3;+0:6](-[O-])=[O;H0;D1;+0:7]):[c:8]>>[C:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8] | null | [] | null | null | 3 | HOUR | The 2-ethyl nicotinic acid lithium salt (5 g, 3.18 mmol) in distilled THF (400 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF) (25 mL) was added dropwise. The reaction was stirred for 3 hours at room temperature then cooled to 0° C. and quenched with EtOAc (949 μL), then H2O (949 μL), th... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | null | 3 | CCc1ncccc1C(=O)[O-]>C1CCOC1>CCc1ncccc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-090d23f63738479ca8c99ffd51c34f39 | CCc1ncccc1CO.O=S(Cl)Cl>>CCc1ncccc1CCl | C(C)C1=NC=CC=C1CO.S(=O)(Cl)Cl>>C(C)C1=NC=CC=C1CCl | O[CH2:9][c:8]1[c:3]([CH2:2][CH3:1])[n:4][cH:5][cH:6][cH:7]1.O=S(Cl)[Cl:10]>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][Cl:10] | CCc1ncccc1CO.O=S(Cl)Cl | CCc1ncccc1CCl | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C:6]):[#7;a:7]:[c:8]>>[C:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1]):[c:4] | null | [] | 0 | CELSIUS | 3 | HOUR | The 2-ethyl-3-hydroxymethylpyridine (2.3 g, 16.8 mmol) was dissolved in CH2Cl2 (100 mL) and cooled under nitrogen to 0° C. and thionyl chloride (7.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (100 mL) and s... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | HCl | C(Cl)Cl | 0 | 3 | CCc1ncccc1CO.O=S(Cl)Cl>C(Cl)Cl>CCc1ncccc1CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50b5f885709f4236b5aee536d764bea9 | CCc1ncccc1CCl.O=C(OO)c1cccc(Cl)c1>>CCc1c(CCl)ccc[n+]1[O-] | C(C)C1=NC=CC=C1CCl.ClC1=CC(=CC=C1)C(=O)OO>>C(C)C1=[N+](C=CC=C1CCl)[O-] | [CH3:1][CH2:2][c:3]1[c:4]([CH2:5][Cl:6])[cH:7][cH:8][cH:9][n:10]1.O=C(O[OH:11])c1cccc(Cl)c1>>[CH3:1][CH2:2][c:3]1[c:4]([CH2:5][Cl:6])[cH:7][cH:8][cH:9][n+:10]1[O-:11] | CCc1ncccc1CCl.O=C(OO)c1cccc(Cl)c1 | CCc1c(CCl)ccc[n+]1[O-] | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1cc[nH+]cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[C:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | null | [] | 0 | CELSIUS | 2 | HOUR | The 2-ethyl-3-chloromethylpyridine (2.4 g, 15.4 mmol) was dissolved in CHCl3 (100 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 4.2 g) was added in small portions. The reaction was stirred for 2 hours. The reaction was extracted twice with saturated aqueous sodium bicarbonate (100 mL). The or... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HCl | C(Cl)(Cl)Cl | 0 | 2 | CCc1ncccc1CCl.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>CCc1c(CCl)ccc[n+]1[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13eeac45e3ff4344b45ee3f41e200838 | CCOC(=O)c1cccnc1C(C)C>>CC(C)c1ncccc1CO | C(C)(C)C1=NC=CC=C1C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)(C)C1=NC=CC=C1CO | CCO[C:10]([c:9]1[c:4]([CH:2]([CH3:1])[CH3:3])[n:5][cH:6][cH:7][cH:8]1)=[O:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][OH:11] | CCOC(=O)c1cccnc1C(C)C | CC(C)c1ncccc1CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[C:6]):[#7;a:7]:[c:8]>>[C:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | 18 | HOUR | The 2-isopropyl-3-carboethoxypyridine (400 mg, 2 mmol) in distilled THF (50 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF) (2.07 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (100 μL), then H2O (100 μL), th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 18 | CCOC(=O)c1cccnc1C(C)C>C1CCOC1>CC(C)c1ncccc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4bba085d9504420e80535135054ff927 | CC(C)c1ncccc1CO.O=S(Cl)Cl>>CC(C)c1ncccc1CCl | C(C)(C)C1=NC=CC=C1CO.S(=O)(Cl)Cl>>C(C)(C)C1=NC=CC=C1CCl | O[CH2:10][c:9]1[c:4]([CH:2]([CH3:1])[CH3:3])[n:5][cH:6][cH:7][cH:8]1.O=S(Cl)[Cl:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][Cl:11] | CC(C)c1ncccc1CO.O=S(Cl)Cl | CC(C)c1ncccc1CCl | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C:6]):[#7;a:7]:[c:8]>>[C:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1]):[c:4] | null | [] | 0 | CELSIUS | 3 | HOUR | The 2-isopropyl-3-hydroxymethylpyridine (240 mg, 1.59 mmol) was dissolved in CH2Cl2 (15 mL) and cooled under nitrogen to 0° C. and thionyl chloride (1.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and satura... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | HCl | C(Cl)Cl | 0 | 3 | CC(C)c1ncccc1CO.O=S(Cl)Cl>C(Cl)Cl>CC(C)c1ncccc1CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-52cbceab19b44bab836d091fb3264cf6 | CC(C)c1ncccc1CCl.O=C(OO)c1cccc(Cl)c1>>CC(C)c1c(CCl)ccc[n+]1[O-] | C(C)(C)C1=NC=CC=C1CCl.ClC1=CC(=CC=C1)C(=O)OO>>C(C)(C)C1=[N+](C=CC=C1CCl)[O-] | [CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([CH2:6][Cl:7])[cH:8][cH:9][cH:10][n:11]1.O=C(O[OH:12])c1cccc(Cl)c1>>[CH3:1][CH:2]([CH3:3])[c:4]1[c:5]([CH2:6][Cl:7])[cH:8][cH:9][cH:10][n+:11]1[O-:12] | CC(C)c1ncccc1CCl.O=C(OO)c1cccc(Cl)c1 | CC(C)c1c(CCl)ccc[n+]1[O-] | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1cc[nH+]cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[C:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | null | [] | 0 | CELSIUS | 2 | HOUR | The 2-isopropyl-3-hydroxymethylpyridine (240 mg, 1.59 mmol) was dissolved in CH2Cl2 (15 mL) and cooled under nitrogen to 0° C. and thionyl chloride (1.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and satura... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HCl | C(Cl)(Cl)Cl | 0 | 2 | CC(C)c1ncccc1CCl.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>CC(C)c1c(CCl)ccc[n+]1[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b7921c79135478487a5a927dd9e4a45 | CCOC(=O)c1c(C)ccnc1C>>Cc1ccnc(C)c1CO | CC1=NC=CC(=C1C(=O)OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CC1=NC=CC(=C1CO)C | CCO[C:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][n:5][c:6]1[CH3:7])=[O:10]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH3:7])[c:8]1[CH2:9][OH:10] | CCOC(=O)c1c(C)ccnc1C | Cc1ccnc(C)c1CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[C;D1;H3:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | 18 | HOUR | The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (2.5 mL), then H2O (2.5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 18 | CCOC(=O)c1c(C)ccnc1C>C1CCOC1>Cc1ccnc(C)c1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bfc9e545236f4da9864ea3f99c2d6fe8 | Cc1ccnc(C)c1CO.O=S(Cl)Cl>>Cc1ccnc(C)c1CCl | CC1=NC=CC(=C1CO)C.S(=O)(Cl)Cl>>CC1=NC=CC(=C1CCl)C | O[CH2:9][c:8]1[c:2]([CH3:1])[cH:3][cH:4][n:5][c:6]1[CH3:7].O=S(Cl)[Cl:10]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH3:7])[c:8]1[CH2:9][Cl:10] | Cc1ccnc(C)c1CO.O=S(Cl)Cl | Cc1ccnc(C)c1CCl | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[C;D1;H3:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1]):[c:4] | null | [] | 0 | CELSIUS | 18 | HOUR | The 2,4-dimethyl-3-hydroxymethylpyridine (19.2 g, 140 mmol) was dissolved in CH2Cl2 (800 mL) and cooled under nitrogen to 0° C. and thionyl chloride (125 mL) was slowly added and the reaction was stirred for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and satu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | HCl | C(Cl)Cl | 0 | 18 | Cc1ccnc(C)c1CO.O=S(Cl)Cl>C(Cl)Cl>Cc1ccnc(C)c1CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc2379efbe054eccaf35ae30843004da | Cc1ccnc(C)c1CCl>>Cc1cc[n+]([O-])c(C)c1CCl | CC1=NC=CC(=C1CCl)C.ClC1=CC(=CC=C1)C(=O)OO>>CC1=[N+](C=CC(=C1CCl)C)[O-] | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:7]([CH3:8])[c:9]1[CH2:10][Cl:11]>>[CH3:1][c:2]1[cH:3][cH:4][n+:5]([O-:6])[c:7]([CH3:8])[c:9]1[CH2:10][Cl:11] | Cc1ccnc(C)c1CCl | Cc1cc[n+]([O-])c(C)c1CCl | null | null | C(Cl)(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] | null | [] | 0 | CELSIUS | 4 | HOUR | The 2,4-dimethyl-3-chloromethylpyridine (21.5 g, 138 mmol) was dissolved in CHCl3 (800 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 35 g) was added in small portions. The reaction was stirred for 4 hours. The solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL). Th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | null | C(Cl)(Cl)Cl | 0 | 4 | Cc1ccnc(C)c1CCl>C(Cl)(Cl)Cl>Cc1cc[n+]([O-])c(C)c1CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-75cd419ae27e4e64877635a7083429d0 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC>>COC(=O)c1ccc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1OC | C(=O)(OC(C)(C)C)N[C@@H]1CC[C@H](CC1)O.N(=NC(=O)OCC)C(=O)OCC.OC1=CC(=C(C(=O)OC)C=C1)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(=O)(OC(C)(C)C)N[C@@H]1CC[C@@H](CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC | O[C@H:12]1[CH2:13][CH2:14][C@H:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]1.CCOC(=O)N=N[C:10](OCC)=[O:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:26][c:27]1[O:28][CH3:29]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[C@H:12]2[CH2:13][C... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC | COC(=O)c1ccc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1OC | null | null | C1CCOC1 | Acylation | OtherReaction | 8e7f7aec30b10cb52f82d427bef98ab15d43a92fc5e2b024cb3b9ec94ed6a028 | 99cbc1de664ce75fe7841777e00c71bc93fd4ae2bce0b73a15911d06040840b5 | O=C(Oc1ccccc1)C1CCCCC1 | C-C-O-C(=O)-N=N-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C-C.O-[C@@H;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[C:4]-[C@@H;D3;+0:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:6]-[C:7] | null | [] | 0 | CELSIUS | null | null | To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (1.09 g, 6.0 mmol) in dry THF (7 mL) was added triphenylphosphine (1.57 g, 6.0 mmol) and the solution was cooled to 0° C. A 4.0 mL volume of N-Boc-trans-1-amino-4-cyclohexanol (1 g, 4.0 mmol) and diethyl azodicarboxylate (945 μL, 6.0 mmol) in THF was added dro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Secondary alcohol.Aromatic alcohol | Ester | C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | C1CCOC1 | 0 | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC>C1CCOC1>COC(=O)c1ccc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c883c9ea34ed4863b03fce02c544723e | COC(=O)c1ccc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1OC>>COc1cc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)ccc1C(=O)O | C(=O)(OC(C)(C)C)N[C@@H]1CC[C@@H](CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>C(=O)(OC(C)(C)C)N[C@@H]1CC[C@@H](CC1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC | C[O:28][C:26]([c:25]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7](=[O:8])[C@H:9]2[CH2:10][CH2:11][C@@H:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]2)[cH:23][cH:24]1)=[O:27]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[C@H:9]2[CH2:10][CH2:11][C@@H:12]([NH:13][C:14](=[O:15])[O:16]... | COC(=O)c1ccc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1OC | COc1cc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)ccc1C(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)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 | [] | 45 | CELSIUS | null | null | To a stirred solution of methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate (220 mg, 0.52 mmol) in THF:H2O (5 mL: 1 mL) was added LiOH.H2O (67.6 mg, 1.59 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude so... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CCCCC1 | Other | C1CCOC1 | 45 | null | COC(=O)c1ccc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1OC>C1CCOC1>COc1cc(OC(=O)[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a131d665a87f4613af62e1177a8607d3 | O=C1C=COC(=S(=O)=O)C1>>O=S(=O)=c1cc(O)cco1 | S(=O)(=O)=C1OC=CC(C1)=O.[BH4-].[Na+]>>S(=O)(=O)=C1OC=CC(=C1)O | [O:1]=[S:2](=[O:3])=[C:4]1[CH2:5][C:6](=[O:7])[CH:8]=[CH:9][O:10]1>>[O:1]=[S:2](=[O:3])=[c:4]1[cH:5][c:6]([OH:7])[cH:8][cH:9][o:10]1 | O=C1C=COC(=S(=O)=O)C1 | O=S(=O)=c1cc(O)cco1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 48f6a1ae20952a8d41bee1c84e0d2ca7d83fe14adec55c711dcca672b806b331 | 809a3d08c9122e2f3c0270c24e439deaab1c0993f94d7d2072d61ea347b6388c | S=c1cccco1 | [O;D1;H0:1]=[#16:2](=[O;D1;H0:3])=[C;H0;D3;+0:4]1-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-[O;H0;D2;+0:10]-1>>[O;D1;H0:1]=[#16:2](=[O;D1;H0:3])=[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[OH;D1;+0:7]):[cH;D2;+0:8]:[cH;D2;+0:9]:[o;H0;D2;+0:10]:1 | null | [] | null | null | 16 | HOUR | A stirred solution of sulfonylpyran-4-one (1.2 g, 8.1 mmol) in MeOH (20 mL) was cooled to 0° C. under Argon and treated with NaBH4 (331 mg, 9.0 mmol). The reaction was stirred over 16 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil was chromatographed on a ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Aromatic alcohol | C1=COCCC1 | c1ccocc1 | c1ccocc1 | null | CO | null | 16 | O=C1C=COC(=S(=O)=O)C1>CO>O=S(=O)=c1cc(O)cco1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e3ff06e7d5dc4790a4038ff5d1f041f4 | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.O=S(=O)=c1cc(O)cco1>>COC(=O)c1ccc(OC(=O)c2cc(=S(=O)=O)cco2)cc1OC | S(=O)(=O)=C1OC=CC(=C1)O.N(=NC(=O)OCC)C(=O)OCC.C1CCOC1.OC1=CC(=C(C(=O)OC)C=C1)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>>S(=O)(=O)=C1C=C(OC=C1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC | CCOC(=O)N=N[C:10](OCC)=[O:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:21][c:22]1[O:23][CH3:24].O[c:14]1[cH:13][c:12](=[S:15](=[O:16])=[O:17])[o:20][cH:19][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[c:12]2[cH:13][c:14](=[S:15](=[O:16])=[O:17])[cH:18][cH:19][o:20]2)... | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.O=S(=O)=c1cc(O)cco1 | COC(=O)c1ccc(OC(=O)c2cc(=S(=O)=O)cco2)cc1OC | null | null | null | Acylation | OtherReaction | 82d3e3db198980f8c67f3eef4d9a4d912866b4f02d668a9bb06a72a6b1dd6d52 | e265b1a668f6a16830e4b2b8abe472d5c9a52f6819ca25184b71f87b06186734 | O=C(Oc1ccccc1)c1cc(=S)cco1 | C-C-O-C(=O)-N=N-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C-C.O-[c;H0;D3;+0:3]1:[c:4]:[c;H0;D3;+0:5](=[S;H0;D3;+0:6](=[O;D1;H0:7])=[O;D1;H0:8]):[#8;a:9]:[c:10]:[c:11]:1.[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15])-[c;H0;D3;+0:5]1:[#8;a:9]:[c:10]:[c:11]:[c;H0;D3;+0:3](=[... | null | [] | 0 | CELSIUS | null | null | To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (364 mg, 2.0 mmol) in dry THF (4 mL) was added triphenylphosphine (524.6 mg, 2.0 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of sulfonylpyran-4-ol (200 mg, 1.33 mmol) and diethyl azodicarboxylate (315 μL, 2.0 mmol) in THF was added dropwise via ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Aromatic alcohol.Aromatic alcohol | Ester | c1ccocc1 | c1ccocc1 | c1ccccc1.c1ccocc1 | HO- | null | 0 | null | CCOC(=O)N=NC(=O)OCC.COC(=O)c1ccc(O)cc1OC.O=S(=O)=c1cc(O)cco1>>COC(=O)c1ccc(OC(=O)c2cc(=S(=O)=O)cco2)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-633f98fd12d84e92930ec5dccc1d3957 | COC(=O)c1ccc(OC(=O)c2cc(=S(=O)=O)cco2)cc1OC>>COc1cc(OC(=O)c2cc(=S(=O)=O)cco2)ccc1C(=O)O | S(=O)(=O)=C1C=C(OC=C1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>S(=O)(=O)=C1C=C(OC=C1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC | C[O:23][C:21]([c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7](=[O:8])[c:9]2[cH:10][c:11](=[S:12](=[O:13])=[O:14])[cH:15][cH:16][o:17]2)[cH:18][cH:19]1)=[O:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[c:9]2[cH:10][c:11](=[S:12](=[O:13])=[O:14])[cH:15][cH:16][o:17]2)[cH:18][cH:19][c:20]1[C:21](=[O:22])[OH:23] | COC(=O)c1ccc(OC(=O)c2cc(=S(=O)=O)cco2)cc1OC | COc1cc(OC(=O)c2cc(=S(=O)=O)cco2)ccc1C(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)c1cc(=S)cco1 | 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 | [] | 45 | CELSIUS | null | null | To a stirred solution of methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate (470 mg, 1.5 mmol)in THF:H2O (18 mL: 2 mL) was added LiOH.H2O (128 mg, 3 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid passed through a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccocc1 | Other | C1CCOC1 | 45 | null | COC(=O)c1ccc(OC(=O)c2cc(=S(=O)=O)cco2)cc1OC>C1CCOC1>COc1cc(OC(=O)c2cc(=S(=O)=O)cco2)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46bdac7b5dca4dd2b9ea60dfb2c0fdfb | COC(=O)c1ccc(OC(=O)C2CC(=S(=O)=O)c3ccccc3O2)cc1OC>>COc1cc(OC(=O)C2CC(=S(=O)=O)c3ccccc3O2)ccc1C(=O)O | S(=O)(=O)=C1CC(OC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC.O.O[Li].O>>S(=O)(=O)=C1CC(OC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC | C[O:27][C:25]([c:24]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][C:11](=[S:12](=[O:13])=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[O:21]2)[cH:22][cH:23]1)=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[CH:9]2[CH2:10][C:11](=[S:12](=[O:13])=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19]... | COC(=O)c1ccc(OC(=O)C2CC(=S(=O)=O)c3ccccc3O2)cc1OC | COc1cc(OC(=O)C2CC(=S(=O)=O)c3ccccc3O2)ccc1C(=O)O | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Oc1ccccc1)C1CC(=S)c2ccccc2O1 | 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 | [] | 45 | CELSIUS | null | null | To a stirred solution of methyl 4-[4-sulfonylchromanoyloxy]-2-methoxybenzoate (500 mg, 1.38 mmol) in THF:H2O (18 mL: 2 mL) was added LiOH.H2O (175 mg, 4.14 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passe... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | C1CCOC1 | 45 | null | COC(=O)c1ccc(OC(=O)C2CC(=S(=O)=O)c3ccccc3O2)cc1OC>C1CCOC1>COc1cc(OC(=O)C2CC(=S(=O)=O)c3ccccc3O2)ccc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69fd522121284a219b8d7faaa6a44613 | COc1c(C(=O)O)cc(F)c(O)c1C.C[C@H](O)c1ccncc1>>COC(=O)c1cc(F)c(O[C@@H](C)c2ccncc2)cc1OC | CC=1C(=C(C(=O)O)C=C(C1O)F)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1=CC=C(C=C1)[C@H](C)O>>FC=1C(=CC(=C(C(=O)OC)C1)OC)O[C@@H](C)C1=CC=NC=C1 | [CH3:1][c:19]1[c:9]([OH:10])[c:7]([F:8])[cH:6][c:5]([C:3]([OH:2])=[O:4])[c:20]1[O:21][CH3:22].O[C@@H:11]([CH3:12])[c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([O:10][C@@H:11]([CH3:12])[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][c:20]1[O:21][CH3:22] | COc1c(C(=O)O)cc(F)c(O)c1C.C[C@H](O)c1ccncc1 | COC(=O)c1cc(F)c(O[C@@H](C)c2ccncc2)cc1OC | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8a8724ed8fc380edd0de18f8c85c3981a493ec1ce8a1f1b33cae45dc36c4c406 | f169f08614001d3d83f7341aab0dfd0af402046a91ce1b341334937672ec5630 | c1ccc(OCc2ccncc2)cc1 | O-[C@@H;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[#8:9]-[c:10](:[c:11]-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14]):[c;H0;D3;+0:15](-[CH3;D1;+0:16]):[c:17](-[OH;D1;+0:18]):[c:19]>>[#8:9]-[c:10](:[c:11]-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-[CH3;D1;+0:16]):[cH;D2;+0:15]:[c:17](-[O;H0;D2;+0:18]-[C@@H;D3;+... | null | [] | 0 | CELSIUS | null | null | A stirred solution of methyl 5-fluoro-2-methoxy-4-hydroxybenzoic acid (250 mg, 1.25 mmol, see Scheme II) in THF (15 mL) was treated with triphenylphosphine (494 mg, 1.88 mmol) and cooled to 0° C. under Argon. To this was added, dropwise over a period of 1 h, a solution of (S)-(-)-1-(4-pyridyl)-ethanol (232 mg, 1.88 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | C1CCOC1 | 0 | null | COc1c(C(=O)O)cc(F)c(O)c1C.C[C@H](O)c1ccncc1>C1CCOC1>COC(=O)c1cc(F)c(O[C@@H](C)c2ccncc2)cc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71a42b3bba7745d89371d9c19ddb7d49 | COC(=O)c1cc(F)c(O[C@@H](C)c2ccncc2)cc1OC>>COc1cc(O[C@@H](C)c2ccncc2)c(F)cc1C(=O)O | O.CC#N.Cl.FC=1C(=CC(=C(C(=O)OC)C1)OC)O[C@@H](C)C1=CC=NC=C1.[OH-].[Na+]>>FC=1C(=CC(=C(C(=O)O)C1)OC)O[C@@H](C)C1=CC=NC=C1 | C[O:21][C:19]([c:18]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][C@@H:7]([CH3:8])[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[c:15]([F:16])[cH:17]1)=[O:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][C@@H:7]([CH3:8])[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[c:15]([F:16])[cH:17][c:18]1[C:19](=[O:20])[OH:21] | COC(=O)c1cc(F)c(O[C@@H](C)c2ccncc2)cc1OC | COc1cc(O[C@@H](C)c2ccncc2)c(F)cc1C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OCc2ccncc2)cc1 | 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 | 8 | HOUR | To a stirred solution of methyl 5-fluoro-2-methoxy-4-[1-(S)-(4-pyridyl)ethoxy]benzoate (290 mg, 0.95 mmol) in methanol (5 mL) was added aqueous NaOH (396 μL, 3.6M). The reaction was stirred at ambient temperature overnight and then heated to 45° C. in an oil bath for another 24 h. The reaction pH was lowered to pH 3 us... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | CO | null | 8 | COC(=O)c1cc(F)c(O[C@@H](C)c2ccncc2)cc1OC>CO>COc1cc(O[C@@H](C)c2ccncc2)c(F)cc1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9773b48b03f44090887256b458e3e63d | O=S(=O)(Cl)C(F)(F)F.OCC(F)(F)F>>O=S(=O)(OCC(F)(F)F)C(F)(F)F | FC(S(=O)(=O)Cl)(F)F.C(=O)=O.FC(CO)(F)F.C(C)N(CC)CC>>FC(COS(=O)(=O)C(F)(F)F)(F)F | Cl[S:2](=[O:1])(=[O:3])[C:10]([F:11])([F:12])[F:13].[OH:4][CH2:5][C:6]([F:7])([F:8])[F:9]>>[O:1]=[S:2](=[O:3])([O:4][CH2:5][C:6]([F:7])([F:8])[F:9])[C:10]([F:11])([F:12])[F:13] | O=S(=O)(Cl)C(F)(F)F.OCC(F)(F)F | O=S(=O)(OCC(F)(F)F)C(F)(F)F | null | null | CCOCC.CC(C)O.C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 48fe3ab9ea419cabd2d3de445d20daee08ec8a66d593e83c888de3f63cb35bc2 | 90c05d4caa9001bd1d36ec239cccc93846c698579e9e88faf7db9bc82dbd1926 | null | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[F;D1;H0:8]-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[C:12]-[OH;D1;+0:13]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:13]-[C:12]-[C:9](-[F;D1;H0:8])(-[F;D1;H0:10])-[F;D1;H0:11... | null | [] | 0 | CELSIUS | 1.5 | HOUR | A solution of trifluoromethanesulfonyl chloride (640 μL, 6 mmol) in CH2Cl2 (5 mL) was cooled under argon to -78° C. (IPA:dry ice bath). 2,2,2-Trifluoroethanol was added (365 μL, 5 mmol) and triethylamine (834 μL, 6 mmol) was added dropwise. The reaction was stirred for 1.5 hours then warmed to 0° C. for 1 hour. Anhydro... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Triflate | null | null | null | HCl | CCOCC.CC(C)O.C(Cl)Cl | 0 | 1.5 | O=S(=O)(Cl)C(F)(F)F.OCC(F)(F)F>CCOCC.CC(C)O.C(Cl)Cl>O=S(=O)(OCC(F)(F)F)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c1eb50330c204669ac80b93517bb8dec | O=S(=O)(Cl)C(F)(F)F.OCC(F)(F)F>>O=S(=O)(OCC(F)(F)F)C(F)(F)F | FC(S(=O)(=O)Cl)(F)F.C(=O)=O.FC(CO)(F)F.C(C)N(CC)CC>>FC(COS(=O)(=O)C(F)(F)F)(F)F | Cl[S:2](=[O:1])(=[O:3])[C:10]([F:11])([F:12])[F:13].[OH:4][CH2:5][C:6]([F:7])([F:8])[F:9]>>[O:1]=[S:2](=[O:3])([O:4][CH2:5][C:6]([F:7])([F:8])[F:9])[C:10]([F:11])([F:12])[F:13] | O=S(=O)(Cl)C(F)(F)F.OCC(F)(F)F | O=S(=O)(OCC(F)(F)F)C(F)(F)F | null | null | CCOCC.CC(C)O.C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 48fe3ab9ea419cabd2d3de445d20daee08ec8a66d593e83c888de3f63cb35bc2 | 90c05d4caa9001bd1d36ec239cccc93846c698579e9e88faf7db9bc82dbd1926 | null | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[F;D1;H0:8]-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[C:12]-[OH;D1;+0:13]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:13]-[C:12]-[C:9](-[F;D1;H0:8])(-[F;D1;H0:10])-[F;D1;H0:11... | null | [] | 0 | CELSIUS | 1.5 | HOUR | A solution of trifluoromethanesulfonyl chloride (800 uL, 7.5 mmole) in CH2Cl2 (6 mL) was cooled under argon to -60° C. (IPA:dry ice bath). 2,2,2-Trifluoroethanol was added (456 uL, 6 mmol) and triethylamine (1.04 uL, 7.5 mmol) was added dropwise. The reaction was stirred for 1.5 hours then warmed to 0° C. for 1 hour. A... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Triflate | null | null | null | HCl | CCOCC.CC(C)O.C(Cl)Cl | 0 | 1.5 | O=S(=O)(Cl)C(F)(F)F.OCC(F)(F)F>CCOCC.CC(C)O.C(Cl)Cl>O=S(=O)(OCC(F)(F)F)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e6b8897562d412183a40fa3b1ae7fd3 | COc1cc(OCC(F)(F)F)c(F)cc1C(=O)[O-]>>O=C(O)c1ccc(OCC(F)(F)F)c(F)c1 | COC1=C(C(=O)[O-])C=C(C(=C1)OCC(F)(F)F)F.[OH-].[Na+].Cl>>FC(COC1=CC=C(C(=O)O)C=C1F)(F)F | CO[c:5]1[c:4]([C:2](=[O:1])[O-:3])[cH:16][c:14]([F:15])[c:7]([O:8][CH2:9][C:10]([F:11])([F:12])[F:13])[cH:6]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][C:10]([F:11])([F:12])[F:13])[c:14]([F:15])[cH:16]1 | COc1cc(OCC(F)(F)F)c(F)cc1C(=O)[O-] | O=C(O)c1ccc(OCC(F)(F)F)c(F)c1 | null | null | C1CCOC1.O | Reduction | OtherReaction | 1429fe65d6db718c9183c85d60c34e1d02dcb32f985a35486f4318002b1dab1d | fc36b78de76f2c5141892df769222d9a793f25ecdae731308a2cae6bc6b43b17 | c1ccccc1 | C-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[O-;H0;D1:6])=[O;D1;H0:7]):[c:8]>>[O;D1;H0:7]=[C:5](-[OH;D1;+0:6])-[c:4](:[c:8]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | 50 | CELSIUS | 18 | HOUR | The above methoxy-4-trifluoroethoxy-5-fluorobenzoate (420 mg, 1.7 mmol) was dissolved in freshly distilled THF (50 mL) and water was added (20 mL) and 2N NaOH (2 mL) was dropped into the rapidly stirring solution at room temperature. The solution was warmed to 50° C. and stirred rapidly for 18 hours. The biphasic resul... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C1CCOC1.O | 50 | 18 | COc1cc(OCC(F)(F)F)c(F)cc1C(=O)[O-]>C1CCOC1.O>O=C(O)c1ccc(OCC(F)(F)F)c(F)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68830d19234b4026807695ab721a68e9 | CN(C)C(=O)N(C)C.O=C(Cl)C(=O)Cl>>CN(C)C(Cl)=[N+](C)C.[Cl-] | C(=O)=O.C(C(=O)Cl)(=O)Cl.CN(C(N(C)C)=O)C>>[Cl-].CN(C(=[N+](C)C)Cl)C | O=[C:4]([N:2]([CH3:1])[CH3:3])[N:6]([CH3:7])[CH3:8].O=C(C(=O)[Cl:9])[Cl:5]>>[CH3:1][N:2]([CH3:3])[C:4]([Cl:5])=[N+:6]([CH3:7])[CH3:8].[Cl-:9] | CN(C)C(=O)N(C)C.O=C(Cl)C(=O)Cl | CN(C)C(Cl)=[N+](C)C.[Cl-] | null | null | C(Cl)(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 343921b6cff5b43b8473a5520afb84d0f50313d1265a93af30b50408e3de339a | acce834eaacd8ad844a742ace5a164ab68132488e5eb9b0306e028af44623650 | null | O=C(-[Cl;H0;D1;+0:1])-C(=O)-[Cl;H0;D1;+0:2].O=[C;H0;D3;+0:3](-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6])-[N;H0;D3;+0:7](-[C;D1;H3:8])-[C;D1;H3:9]>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[C;H0;D3;+0:3](-[Cl;H0;D1;+0:1])=[N+;H0;D3:7](-[C;D1;H3:8])-[C;D1;H3:9].[Cl-;H0;D0:2] | null | [] | null | null | null | null | A solution of 3.2 ml (0.037 mol) of oxalyl chloride in 30 ml of anhydrous carbon tetrachloride is added dropwise to a solution of 4.4 ml (0.037 mol) of tetramethylurea in 20 ml of anhydrous carbon tetrachloride with stirring. The reaction medium is maintained at reflux, with continued stirring, until the evolution of g... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Urea | Alkenyl halide.Amidinium | null | null | null | Other | C(Cl)(Cl)(Cl)Cl | null | null | CN(C)C(=O)N(C)C.O=C(Cl)C(=O)Cl>C(Cl)(Cl)(Cl)Cl>CN(C)C(Cl)=[N+](C)C.[Cl-] |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.