dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-23f9fab724b34adeb200118017862dd1 | C1=CCCC=CCC1.C=CCCCC>>C=CCCC=CCCC=CCCCC | C1=CCCC=CCC1.C=CCCCC>>C=CCCC=CCCC=CCCCC | [CH:1]1=[CH:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8]1.[CH2:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14] | C1=CCCC=CCC1.C=CCCCC | C=CCCC=CCCC=CCCCC | null | null | null | C-C Coupling | OtherReaction | d20b4e7dc56465e257fd775d4d8671985ead029dd4419b7ff864815c38b010e4 | ab90d573e51295ebe4fa5fe42d294c94b372ac6d38e43baa10880dc547cec798 | null | [C:1]-[C:2]=[CH2;D1;+0:3].[C:4]1=[CH;D2;+0:5]-[CH2;D2;+0:6]-[C:7]-[C:8]=[C:9]-[C:10]-[C:11]-1>>[C:1]-[C:2]=[CH;D2;+0:3]-[CH2;D2;+0:6]-[C:7]-[C:8]=[C:9]-[C:10]-[C:11]-[C:4]=[CH2;D1;+0:5] | null | [] | null | null | null | null | disproportionating 1,5-cyclooctadiene and 1-hexene in the presence of a disproportionation catalyst under disproportionation conditions suitable to give 1,5,9-tetradecatriene,
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Allyl | C1=CCCC=CCC1 | null | null | null | null | null | null | C1=CCCC=CCC1.C=CCCCC>>C=CCCC=CCCC=CCCCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-04dbb461ed174b00a6244db67ec1e09f | CCCCCCCCCCCC=CC=CC(=O)OCC>>CCCCC=CCCC=CCCCCCCO | C(C)OC(C=CC=CCCCCCCCCCCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>C(CCCCCC=CCCC=CCCCC)O | CCO[C:16]([CH:15]=[CH:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17] | CCCCCCCCCCCC=CC=CC(=O)OCC | CCCCC=CCCC=CCCCCCCO | null | null | O1CCCC1 | Miscellaneous | OtherReaction | c47d5e22a09807ce41258c8c8091cbf374bba9ba440dc37f3a1598f0ad21a2c6 | 51b61043c515ef8fa253c7d7887a5454acb3c42c0a7ec019d773bafeb6ef9856 | null | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-[C:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[C:14]-[C:15]>>[C:15]-[C:14]-[CH;D2;+0:13]=[CH;D2;+0:12]-[C:11]-[C:10]-[CH;D2;+0:9]=[CH;D2;+0:8]-[C:7]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2... | 41 | [{"value": 41.0, "product": "C(CCCCCC=CCCC=CCCCC)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | The ethylhexadecadienoate was reduced with lithium aluminum hydride (LAH) in tetrahydrofuran as follows. An oven dried 3-neck flask equipped with a magnetic stirrer, reflux condenser and an addition funnel was charged with 2 equivalents of LAH in dry tetrahydrofuran (THF). The reaction vessel and contents were maintain... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Conjugated diene | Primary alcohol | null | null | null | HO- | O1CCCC1 | 0 | null | CCCCCCCCCCCC=CC=CC(=O)OCC>O1CCCC1>CCCCC=CCCC=CCCCCCCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1f34b334c3154079baa5ace48e010c6f | C=CCCC=CCCC=CCCCC.CC(=O)OCCBr>>CCCC/C=C\CC/C=C\CCCCCCOC(C)=O | C(C)(=O)OCCBr.C=CCCC=CCCC=CCCCC.C(CCC)[Mg]Cl.Cl>>CCCC/C=C\CC/C=C\CCCCCCOC(=O)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH:13]=[CH2:14].Br[CH2:15][CH2:16][O:17][C:18]([CH3:19])=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]([CH3:19])=[O:20] | C=CCCC=CCCC=CCCCC.CC(=O)OCCBr | CCCC/C=C\CC/C=C\CCCCCCOC(C)=O | null | [Ti](Cl)(Cl)(Cl)Cl | null | C-C Coupling | OtherReaction | e0cd0a1c92898864eb78dc35f69aad261d9d56cb75f84701e3b58315e610ccbc | 593520eafadf1051a99a874788a276472c611d816d2027957f3fb36d0d0b5937 | null | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]=[C:8]-[C:9]-[C:10]-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[C:7]=[C:8]\[C:9]-[C:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6] | 11 | [{"value": 11.0, "product": "CCCC/C=C\\CC/C=C\\CCCCCCOC(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 1,5,9-Tetradecatriene (10 g, 0.052 mol), n-butylmagnesium chloride (24.8 mL of 2.5M in tetrahydrofuran; 0.062 mol) and titanium tetrachloride (0.52 g, 0.0027 mol) were stirred under an inert atmosphere at about 65° C. for about 4.5 hours. The reaction mixture was then cooled to 0° C. and cuprous bromide (0.14 g, 1.0 mm... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | null | null | null | null | Br- | [Ti](Cl)(Cl)(Cl)Cl | 0 | null | C=CCCC=CCCC=CCCCC.CC(=O)OCCBr>[Ti](Cl)(Cl)(Cl)Cl>CCCC/C=C\CC/C=C\CCCCCCOC(C)=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cb7cceca52f64bea985a858db355e6da | C=C[Si](CCC)(CCC)CCC.c1ccc(Pc2ccccc2)cc1>>CCC[Si](CCC)(CCC)CCP(c1ccccc1)c1ccccc1 | C(=C)[Si](CCC)(CCC)CCC.C1(=CC=CC=C1)PC1=CC=CC=C1>>C(CC)[Si](CCC)(CCC)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][Si:4]([CH2:5][CH2:6][CH3:7])([CH2:8][CH2:9][CH3:10])[CH:11]=[CH2:12].[PH:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][CH2:3][Si:4]([CH2:5][CH2:6][CH3:7])([CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][P:13]([c:14]1[cH:15][cH:16][cH:17][cH:18]... | C=C[Si](CCC)(CCC)CCC.c1ccc(Pc2ccccc2)cc1 | CCC[Si](CCC)(CCC)CCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 6e18384a4cb428c82c20d31730f2ac142cfbf9a333fe90e3d93fcc2d02070c0d | 62104ffcb4d4ab6482284e0c7ae124bc1d1d4f4befe80d570c6848ac4dc98f52 | c1ccc(Pc2ccccc2)cc1 | [C:1]-[C:2]-[#14:3](-[C:4]-[C:5])(-[C:6]-[C:7])-[CH;D2;+0:8]=[CH2;D1;+0:9].[c:10]:[c:11](-[PH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[c:16]>>[C:1]-[C:2]-[#14:3](-[C:4]-[C:5])(-[C:6]-[C:7])-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[P;H0;D3;+0:12](-[c:11](:[c:10]):[c:16])-[c:13](:[c:14]):[c:15] | null | [] | null | null | 86 | HOUR | The vinyl tripropyl silane was then reacted with diphenyl phosphine with u.v. initiation for 86 hours in a manner described in Example 1. The conversion was about 95%. The mixture was fractionally distilled to yield approximately 63% of the theoretical yield of the product as a clear, colorless, mobile liquid. The prod... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccccc1 | null | null | null | 86 | C=C[Si](CCC)(CCC)CCC.c1ccc(Pc2ccccc2)cc1>>CCC[Si](CCC)(CCC)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-194e688c8fcd42c49a6cb3b9f02bc458 | C=C[Si](c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(Pc2ccccc2)cc1>>c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | C(=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)PC1=CC=CC=C1>>C1(=CC=CC=C1)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH2:6]=[CH:7][Si:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[cH:1]1[cH:2][cH:3][c:4]([PH:5][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:33][cH:34]1>>[cH:1]1[cH:2][cH:3][c:4]([P:5]([CH2:6][CH2:7][Si:8]([c:9]2[cH:10][cH:11][cH... | C=C[Si](c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(Pc2ccccc2)cc1 | c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | null | null | C1CCCCC1 | Miscellaneous | OtherReaction | 6e18384a4cb428c82c20d31730f2ac142cfbf9a333fe90e3d93fcc2d02070c0d | 62104ffcb4d4ab6482284e0c7ae124bc1d1d4f4befe80d570c6848ac4dc98f52 | c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[#14:3](-[c:4])(-[c:5])-[c:6].[c:7]:[c:8](-[PH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:13]>>[c:4]-[#14:3](-[c:5])(-[c:6])-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[P;H0;D3;+0:9](-[c:8](:[c:7]):[c:13])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | The vinyl triphenyl silane was reacted with 10% excess of diphenyl phosphine. To maintain a homogeneous reaction mixture, a temperature of 80° C. and cyclohexane solvent were employed. After the usual u.v. initiated addition, the reaction mixture was allowed to cool to room temperature. This resulted in the crystalliza... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1CCCCC1 | null | null | C=C[Si](c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(Pc2ccccc2)cc1>C1CCCCC1>c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-909b81726ae141ef9ae0979fc054a554 | C=C[Si](C)(C)C=C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(CCP(c1ccccc1)c1ccccc1)CCP(c1ccccc1)c1ccccc1 | C[Si](C=C)(C=C)C.C1(=CC=CC=C1)PC1=CC=CC=C1>>C1(=CC=CC=C1)P(C1=CC=CC=C1)CC[Si](C)(C)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][Si:2]([CH:4]=[CH2:5])([CH:17]=[CH2:16])[CH3:26].[PH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:31][cH:32][cH:33]1>>[CH3:1][Si:2]([CH3:3])([CH2:4][CH2:5][P:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][P:21]([c:22]1[cH:23][cH:24... | C=C[Si](C)(C)C=C.c1ccc(Pc2ccccc2)cc1 | C[Si](C)(CCP(c1ccccc1)c1ccccc1)CCP(c1ccccc1)c1ccccc1 | null | null | null | Functional Group Addition | OtherReaction | b1bb20dd63ac8c5a5e0bc6b29d4461075647ac2eb63a8a81eeee4a337d766d5c | fe74a335ad2346bf95eb638a0c24226501e5ffaf093082ff41ba660a94071113 | c1ccc(P(CC[SiH2]CCP(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | [C;D1;H3:1]-[Si;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH;D2;+0:4]=[CH2;D1;+0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[c:8]:[c:9](-[PH;D2;+0:10]-[c;H0;D3;+0:11]1:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[c:15]:[cH;D2;+0:16]:1):[c:17]>>[C;D1;H3:1]-[Si;H0;D4;+0:2](-[C;D1;H3:18])(-[C:19]-[C:20]-[#15:21](-[c:22]:[c:23]:[cH;D2;+0:3]:[c:24]:[c:25])... | null | [] | null | null | null | null | A mixture of 9.0 g (0.8 mole) dimethyl divinyl silane and 32.7 g (0.176) diphenylphosphine (10% excess over equivalent amounts) was reacted for 22 hours in the manner described in Example 1. The reaction mixture was fractionated in vacuo to obtain minor amounts of the clear, colorless, slightly viscous liquid monoadduc... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Vinyl.Silyl protective group | Silyl protective group | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | C=C[Si](C)(C)C=C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(CCP(c1ccccc1)c1ccccc1)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ef1ce671b82043a4a7ebe274b6a7e96d | C=CC[Si](C)(C)C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(C)CCCP(c1ccccc1)c1ccccc1 | C(C=C)[Si](C)(C)C.C1(=CC=CC=C1)PC1=CC=CC=C1>>C[Si](C)(C)CCCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH:6]=[CH2:7].[PH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][P:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CC[Si](C)(C)C.c1ccc(Pc2ccccc2)cc1 | C[Si](C)(C)CCCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | c1ccc(Pc2ccccc2)cc1 | [C;D1;H3:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[CH;D2;+0:6]=[CH2;D1;+0:7].[c:8]:[c:9](-[PH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:14]>>[C;D1;H3:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[P;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c:9](:[c:8]):[c:14] | 50 | [{"value": 50.0, "product": "C[Si](C)(C)CCCP(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 22.8 g (0.2 mole) allyl trimethyl silane and 37.2 g (0.2 mole) diphenyl phosphine was reacted for 158 hours in the manner described in Example 1. A subsequent fractional distillation, yielded the desired pure adduct as a clear, colorless liquid. The distillation yield was 50%. The product had a boiling poi... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | c1ccccc1.c1ccccc1 | null | null | null | null | C=CC[Si](C)(C)C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(C)CCCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8d3871044e49488e8efef725977c5779 | CC(C)(C)CP(c1ccccc1)c1ccccc1>>c1ccc(Pc2ccccc2)cc1 | CC(CP(C1=CC=CC=C1)C1=CC=CC=C1)(C)C.CC(CCl)(C)C>>C1(=CC=CC=C1)PC1=CC=CC=C1 | CC(C)(C)C[P:5]([c:4]1[cH:3][cH:2][cH:1][cH:13][cH:12]1)[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[cH:1]1[cH:2][cH:3][c:4]([PH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][cH:13]1 | CC(C)(C)CP(c1ccccc1)c1ccccc1 | c1ccc(Pc2ccccc2)cc1 | null | null | O1CCCC1.CCCCCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Pc2ccccc2)cc1 | C-C(-C)(-C)-C-[P;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[PH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:7] | null | [] | null | null | null | null | The known but unavailable 2,2-dimethylpropyl diphenyl phosphine was derived via reacting 2,2-dimethylpropyl chloride with lithium diphenyl phosphide in a refluxing tetrahydrofuran-hexane solvent mixture. After filtering off the lithium chloride by-product, the 2,2-dimethylpropyl, (i.e., neopentyl) diphenyl phosphine wa... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1.CCCCCC | null | null | CC(C)(C)CP(c1ccccc1)c1ccccc1>O1CCCC1.CCCCCC>c1ccc(Pc2ccccc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-91722db8ad61490eabb8bc763527f4d9 | CC(C)(C)CCCl.c1ccc(Pc2ccccc2)cc1>>CC(C)(C)CCP(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)PC1=CC=CC=C1.CC(CCCl)(C)C>>CC(CCP(C1=CC=CC=C1)C1=CC=CC=C1)(C)C | Cl[CH2:6][CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4].[PH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][P:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CC(C)(C)CCCl.c1ccc(Pc2ccccc2)cc1 | CC(C)(C)CCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccc(Pc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5](-[PH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[P;H0;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c:5](:[c:4]):[c:10] | null | [] | null | null | null | null | As a known compound, t-butylethyl, (i.e., 3,3-dimethylbutyl) diphenyl phosphine was also synthesized via the known displacement approach: the reaction of lithium diphenyl phosphide with 3,3-dimethylbutyl chloride provided the compound in good yield.
Conditions: See reaction.notes.procedure_details.
Workup: provided the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)CCCl.c1ccc(Pc2ccccc2)cc1>>CC(C)(C)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-66a50a8d07224708b09bcfbde3dd4b52 | C=CCN(CC)CC.CCN(CC)C(C)CP(c1ccccc1)c1ccccc1>>CCN(CC)CCCP(c1ccccc1)c1ccccc1 | C(C)N(C(CP(C1=CC=CC=C1)C1=CC=CC=C1)C)CC.C(C=C)N(CC)CC.C1(=CC=CC=C1)PC1=CC=CC=C1>>C(C)N(CC)CCCP(C1=CC=CC=C1)C1=CC=CC=C1 | C=CC[N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].CCN(CC)[CH:7]([CH3:6])[CH2:8][P:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][P:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | C=CCN(CC)CC.CCN(CC)C(C)CP(c1ccccc1)c1ccccc1 | CCN(CC)CCCP(c1ccccc1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dd0928e69b074d78ddca7268fe3286248492488c85489a9d8a4f5b79b2a96d4c | 4fd2dedd0257123b596f490c5ad05d27d987f43ffa88e6da4642bf02540c8c38 | c1ccc(Pc2ccccc2)cc1 | C-C-N(-C-C)-[CH;D3;+0:1](-[CH3;D1;+0:2])-[C:3]-[#15:4].C=C-C-[N;H0;D3;+0:5](-[C:6]-[C;D1;H3:7])-[C:8]-[C;D1;H3:9]>>[#15:4]-[C:3]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:5](-[C:6]-[C;D1;H3:7])-[C:8]-[C;D1;H3:9] | null | [] | null | null | null | null | A mixture of 17 g (0.15 mole) allyl diethyl amine and 30.7 g (0.165 mole, 10% excess) of diphenyl phosphine is reacted in the usual manner with u.v. irradiation for 17 hours. A subsequent analysis of the reaction mixture indicated that about one third of the reactants was converted. The only product formed was the desi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Tertiary amine.Allyl | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | C=CCN(CC)CC.CCN(CC)C(C)CP(c1ccccc1)c1ccccc1>>CCN(CC)CCCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1228ed91a2884b5bbc8e0d36a8f7735b | C=CS(=O)(=O)CC.c1ccc(Pc2ccccc2)cc1>>CCS(=O)(=O)CCP(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)PC1=CC=CC=C1.C(C)S(=O)(=O)C=C>>C(C)S(=O)(=O)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH:6]=[CH2:7].[PH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][P:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CS(=O)(=O)CC.c1ccc(Pc2ccccc2)cc1 | CCS(=O)(=O)CCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 6e18384a4cb428c82c20d31730f2ac142cfbf9a333fe90e3d93fcc2d02070c0d | 62104ffcb4d4ab6482284e0c7ae124bc1d1d4f4befe80d570c6848ac4dc98f52 | c1ccc(Pc2ccccc2)cc1 | [C:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[c:7]:[c:8](-[PH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:13]>>[C:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[P;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c:8](:[c:7]):[c:13] | 69 | [{"value": 69.0, "product": "C(C)S(=O)(=O)CCP(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 105 | MINUTE | A mixture of 64 g (0.34 mole) of diphenyl phosphine and 40.2 g (0.33 mole) of highly reactive, freshly distilled vinyl ethyl sulfone monomer was irradiated in the usual manner. To suppress polymer forming side reactions the temperature of the reaction mixture was kept below 5° C. by an ice-water bath and the u.v. irrad... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccccc1 | null | null | null | 1.75 | C=CS(=O)(=O)CC.c1ccc(Pc2ccccc2)cc1>>CCS(=O)(=O)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-53c96d114adb4998b29cab42f0d8b0f8 | C=CC(=O)OC.c1ccc(Pc2ccccc2)cc1>>COC(=O)CCP(c1ccccc1)c1ccccc1 | C(C=C)(=O)OC.C1(=CC=CC=C1)PC1=CC=CC=C1.C(C=C)(=O)[O-]>>C(=O)(OC)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].[PH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][P:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | C=CC(=O)OC.c1ccc(Pc2ccccc2)cc1 | COC(=O)CCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | d6be27b1041552a496d721dd1299531aa4ec662959125630d6383089b7510de4 | 984b7296581f8a0e0e59498d0e3f240bdf47ba41a5630fc2689c4747c58a9bd0 | c1ccc(Pc2ccccc2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[c:7]:[c:8](-[PH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:13]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[P;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c:8](:[c:7]):[c:13] | null | [] | null | null | 1 | HOUR | A mixture of 8.6 g (0.1 mole) methyl acrylate and 19.5 g (0.105 mole, 5% excess) of diphenyl phosphine was reacted at 15° C. in the routine manner of Example 1. U.V. irradiation resulted in a rapid reaction. After 1 hour, there was no acrylate left unconverted. The expected mono- and diadducts were formed in a weight r... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester | null | null | c1ccccc1.c1ccccc1 | null | null | null | 1 | C=CC(=O)OC.c1ccc(Pc2ccccc2)cc1>>COC(=O)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7c564b3342b0464f82f7c3d532b9c3b1 | C=C[Si](CCC)(CCC)CCC.c1ccc(Pc2ccccc2)cc1>>CCC[Si](CCC)(CCC)CCP(c1ccccc1)c1ccccc1 | C(=C)[Si](CCC)(CCC)CCC.C1(=CC=CC=C1)PC1=CC=CC=C1>>C(CC)[Si](CCC)(CCC)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][Si:4]([CH2:5][CH2:6][CH3:7])([CH2:8][CH2:9][CH3:10])[CH:11]=[CH2:12].[PH:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][CH2:3][Si:4]([CH2:5][CH2:6][CH3:7])([CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][P:13]([c:14]1[cH:15][cH:16][cH:17][cH:18]... | C=C[Si](CCC)(CCC)CCC.c1ccc(Pc2ccccc2)cc1 | CCC[Si](CCC)(CCC)CCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 6e18384a4cb428c82c20d31730f2ac142cfbf9a333fe90e3d93fcc2d02070c0d | 62104ffcb4d4ab6482284e0c7ae124bc1d1d4f4befe80d570c6848ac4dc98f52 | c1ccc(Pc2ccccc2)cc1 | [C:1]-[C:2]-[#14:3](-[C:4]-[C:5])(-[C:6]-[C:7])-[CH;D2;+0:8]=[CH2;D1;+0:9].[c:10]:[c:11](-[PH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[c:16]>>[C:1]-[C:2]-[#14:3](-[C:4]-[C:5])(-[C:6]-[C:7])-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[P;H0;D3;+0:12](-[c:11](:[c:10]):[c:16])-[c:13](:[c:14]):[c:15] | null | [] | null | null | 86 | HOUR | The vinyl tripropyl silane was then reacted with diphenyl phosphine with u.v. initiation for 86 hours in a manner described in Example 1. The conversion was about 95%. The mixture was fractionally distilled to yield approximately 63% of the theoretical yield of the product as a clear, colorless, mobile liquid. The prod... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccccc1 | null | null | null | 86 | C=C[Si](CCC)(CCC)CCC.c1ccc(Pc2ccccc2)cc1>>CCC[Si](CCC)(CCC)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-68fbcfed305f46ffbbad4248378d8a8f | C=C[Si](c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(Pc2ccccc2)cc1>>c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | C(=C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)PC1=CC=CC=C1>>C1(=CC=CC=C1)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH2:6]=[CH:7][Si:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[cH:1]1[cH:2][cH:3][c:4]([PH:5][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:33][cH:34]1>>[cH:1]1[cH:2][cH:3][c:4]([P:5]([CH2:6][CH2:7][Si:8]([c:9]2[cH:10][cH:11][cH... | C=C[Si](c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(Pc2ccccc2)cc1 | c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | null | null | C1CCCCC1 | Miscellaneous | OtherReaction | 6e18384a4cb428c82c20d31730f2ac142cfbf9a333fe90e3d93fcc2d02070c0d | 62104ffcb4d4ab6482284e0c7ae124bc1d1d4f4befe80d570c6848ac4dc98f52 | c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[#14:3](-[c:4])(-[c:5])-[c:6].[c:7]:[c:8](-[PH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:13]>>[c:4]-[#14:3](-[c:5])(-[c:6])-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[P;H0;D3;+0:9](-[c:8](:[c:7]):[c:13])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | The vinyl triphenyl silane was reacted with 10% excess of diphenyl phosphine. To maintain a homogeneous reaction mixture, a temperature of 80° C. and cyclohexane solvent were employed. After the usual u.v. initiated addition, the reaction mixture was allowed to cool to room temperature. This resulted in the crystalliza... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1CCCCC1 | null | null | C=C[Si](c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(Pc2ccccc2)cc1>C1CCCCC1>c1ccc(P(CC[Si](c2ccccc2)(c2ccccc2)c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-32c6ed48ad464867977d13f421d0483d | C=C[Si](C)(C)C=C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(CCP(c1ccccc1)c1ccccc1)CCP(c1ccccc1)c1ccccc1 | C[Si](C=C)(C=C)C.C1(=CC=CC=C1)PC1=CC=CC=C1>>C1(=CC=CC=C1)P(C1=CC=CC=C1)CC[Si](C)(C)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][Si:2]([CH:4]=[CH2:5])([CH:17]=[CH2:16])[CH3:26].[PH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:31][cH:32][cH:33]1>>[CH3:1][Si:2]([CH3:3])([CH2:4][CH2:5][P:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][P:21]([c:22]1[cH:23][cH:24... | C=C[Si](C)(C)C=C.c1ccc(Pc2ccccc2)cc1 | C[Si](C)(CCP(c1ccccc1)c1ccccc1)CCP(c1ccccc1)c1ccccc1 | null | null | null | Functional Group Addition | OtherReaction | b1bb20dd63ac8c5a5e0bc6b29d4461075647ac2eb63a8a81eeee4a337d766d5c | fe74a335ad2346bf95eb638a0c24226501e5ffaf093082ff41ba660a94071113 | c1ccc(P(CC[SiH2]CCP(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | [C;D1;H3:1]-[Si;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH;D2;+0:4]=[CH2;D1;+0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[c:8]:[c:9](-[PH;D2;+0:10]-[c;H0;D3;+0:11]1:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[c:15]:[cH;D2;+0:16]:1):[c:17]>>[C;D1;H3:1]-[Si;H0;D4;+0:2](-[C;D1;H3:18])(-[C:19]-[C:20]-[#15:21](-[c:22]:[c:23]:[cH;D2;+0:3]:[c:24]:[c:25])... | null | [] | null | null | null | null | A mixture of 9.0 g (0.8 mole) dimethyl divinyl silane and 32.7 g (0.176) diphenyl phosphine (10% excess over equivalent amounts) was reacted for 22 hours in the manner described in Example 1. The reaction mixture was fractionated in vacuo to obtain minor amounts of the clear, colorless, slightly viscous liquid monoaddu... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Vinyl.Silyl protective group | Silyl protective group | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | C=C[Si](C)(C)C=C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(CCP(c1ccccc1)c1ccccc1)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fa87d950042d4fcdaa04be4069a18739 | C=CC[Si](C)(C)C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(C)CCCP(c1ccccc1)c1ccccc1 | C(C=C)[Si](C)(C)C.C1(=CC=CC=C1)PC1=CC=CC=C1>>C[Si](C)(C)CCCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH:6]=[CH2:7].[PH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][P:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CC[Si](C)(C)C.c1ccc(Pc2ccccc2)cc1 | C[Si](C)(C)CCCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | c1ccc(Pc2ccccc2)cc1 | [C;D1;H3:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[CH;D2;+0:6]=[CH2;D1;+0:7].[c:8]:[c:9](-[PH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:14]>>[C;D1;H3:1]-[#14:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[P;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c:9](:[c:8]):[c:14] | 50 | [{"value": 50.0, "product": "C[Si](C)(C)CCCP(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 22.8 g (0.2 mole) allyl trimethyl silane and 37.2 g (0.2 mole) diphenyl phosphine was reacted for 158 hours in the manner described in Example 1. A subsequent fractional distillation, yielded the desired pure adduct as a clear, colorless liquid. The distillation yield was 50%. The product had a boiling poi... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | c1ccccc1.c1ccccc1 | null | null | null | null | C=CC[Si](C)(C)C.c1ccc(Pc2ccccc2)cc1>>C[Si](C)(C)CCCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-08b859787be44c5ca80ca28ea039eccf | CC(C)(C)CP(c1ccccc1)c1ccccc1>>c1ccc(Pc2ccccc2)cc1 | CC(CP(C1=CC=CC=C1)C1=CC=CC=C1)(C)C.CC(CCl)(C)C>>C1(=CC=CC=C1)PC1=CC=CC=C1 | CC(C)(C)C[P:5]([c:4]1[cH:3][cH:2][cH:1][cH:13][cH:12]1)[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[cH:1]1[cH:2][cH:3][c:4]([PH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][cH:13]1 | CC(C)(C)CP(c1ccccc1)c1ccccc1 | c1ccc(Pc2ccccc2)cc1 | null | null | O1CCCC1.CCCCCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Pc2ccccc2)cc1 | C-C(-C)(-C)-C-[P;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[PH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:7] | null | [] | null | null | null | null | The known but unavailable 2,2-dimethylpropyl diphenyl phosphine was derived via reacting 2,2-dimethylpropyl chloride with lithium diphenyl phosphide in a refluxing tetrahydrofuran-hexane solvent mixture. After filtering off the lithium chloride by-product, the 2,2-dimethylpropyl, (i.e., neopentyl) diphenyl phosphine wa... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1.CCCCCC | null | null | CC(C)(C)CP(c1ccccc1)c1ccccc1>O1CCCC1.CCCCCC>c1ccc(Pc2ccccc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1d018a0b47bb4fd9ba066ec1241c102e | CC(C)(C)CCCl.c1ccc(Pc2ccccc2)cc1>>CC(C)(C)CCP(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)PC1=CC=CC=C1.CC(CCCl)(C)C>>CC(CCP(C1=CC=CC=C1)C1=CC=CC=C1)(C)C | Cl[CH2:6][CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4].[PH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][P:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CC(C)(C)CCCl.c1ccc(Pc2ccccc2)cc1 | CC(C)(C)CCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccc(Pc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5](-[PH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[P;H0;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c:5](:[c:4]):[c:10] | null | [] | null | null | null | null | As a known compound, t-butylethyl, (i.e., 3,3-dimethylbutyl) diphenyl phosphine was also synthesized via the known displacement approach: the reaction of lithium diphenyl phosphide with 3,3-dimethylbutyl chloride provided the compound in good yield.
Conditions: See reaction.notes.procedure_details.
Workup: provided the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)CCCl.c1ccc(Pc2ccccc2)cc1>>CC(C)(C)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-61afbc3045f548f68df78f5d98b3b73a | C=CCN(CC)CC.CCN(CC)C(C)CP(c1ccccc1)c1ccccc1>>CCN(CC)CCCP(c1ccccc1)c1ccccc1 | C(C)N(C(CP(C1=CC=CC=C1)C1=CC=CC=C1)C)CC.C(C=C)N(CC)CC.C1(=CC=CC=C1)PC1=CC=CC=C1>>C(C)N(CC)CCCP(C1=CC=CC=C1)C1=CC=CC=C1 | C=CC[N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].CCN(CC)[CH:7]([CH3:6])[CH2:8][P:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][P:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | C=CCN(CC)CC.CCN(CC)C(C)CP(c1ccccc1)c1ccccc1 | CCN(CC)CCCP(c1ccccc1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dd0928e69b074d78ddca7268fe3286248492488c85489a9d8a4f5b79b2a96d4c | 4fd2dedd0257123b596f490c5ad05d27d987f43ffa88e6da4642bf02540c8c38 | c1ccc(Pc2ccccc2)cc1 | C-C-N(-C-C)-[CH;D3;+0:1](-[CH3;D1;+0:2])-[C:3]-[#15:4].C=C-C-[N;H0;D3;+0:5](-[C:6]-[C;D1;H3:7])-[C:8]-[C;D1;H3:9]>>[#15:4]-[C:3]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:5](-[C:6]-[C;D1;H3:7])-[C:8]-[C;D1;H3:9] | null | [] | null | null | null | null | A mixture of 17 g (0.15 mole) allyl diethyl amine and 30.70 g (0.165 mole, 10% excess) of diphenyl phosphine is reacted in the usual manner with u.v. irradiation for 17 hours. A subsequent analysis of the reaction mixture indicated that about one third of the reactants was converted. The only product formed was the des... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Tertiary amine.Allyl | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | C=CCN(CC)CC.CCN(CC)C(C)CP(c1ccccc1)c1ccccc1>>CCN(CC)CCCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9d10bc24ee80433b8fb0af20718b63f2 | C=CC(=O)OC.c1ccc(Pc2ccccc2)cc1>>COC(=O)CCP(c1ccccc1)c1ccccc1 | C(C=C)(=O)OC.C1(=CC=CC=C1)PC1=CC=CC=C1.C(C=C)(=O)[O-]>>C(=O)(OC)CCP(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].[PH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][P:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | C=CC(=O)OC.c1ccc(Pc2ccccc2)cc1 | COC(=O)CCP(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | d6be27b1041552a496d721dd1299531aa4ec662959125630d6383089b7510de4 | 984b7296581f8a0e0e59498d0e3f240bdf47ba41a5630fc2689c4747c58a9bd0 | c1ccc(Pc2ccccc2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[c:7]:[c:8](-[PH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:13]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[P;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c:8](:[c:7]):[c:13] | null | [] | null | null | 1 | HOUR | A mixture of 8.6 g (0.1 mole) and methyl acrylate and 19.5 g (0.105 mole, 5% excess) of diphenyl phosphine was reacted at 15° C. in the routine manner of Example 1. U.V. irradiation resulted in a rapid reaction. After 1 hour, there was no acrylate left unconverted. The expected mono- and diadducts were formed in a weig... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester | null | null | c1ccccc1.c1ccccc1 | null | null | null | 1 | C=CC(=O)OC.c1ccc(Pc2ccccc2)cc1>>COC(=O)CCP(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f1cce4a899924dd287b20155ca3edf2d | CC(=O)OC(C)=O.CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1>>COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 | [OH-].[K+].[OH-].[K+].[OH-].[NH4+].CN(C1=CC=C(C=C1)C(=O)C1=C(C(=O)O)C=C(C=C1)N(C)C)C.C(C)(=O)OC(C)=O.N1CCCCC1>>COC1(OC(=O)C2=CC(=CC=C12)N(C)C)C1=CC=C(C=C1)N(C)C | CC(=O)OC(=O)[CH3:1].[O:2]=[C:3]([c:4]1[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[c:24]1[c:16]([C:14]([OH:13])=[O:15])[cH:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]2)[O:13][C:14](=[O:15])[c:16]2[cH:17][c:18]([N:19]([... | CC(=O)OC(C)=O.CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1 | COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 | null | null | C1(=CC=CC=C1)C.CO | Heteroatom Alkylation and Arylation | OtherReaction | bcbfb20cc559fc33ba9c903f9b2a14c33777efc913a1406beebb4bb9ee92d156 | dee7c0056508ca8e095c6fc484821bc9e0a64b51b4d8f83eb277271d425e0163 | O=C1OC(c2ccccc2)c2ccccc21 | C-C(=O)-O-C(=O)-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]):[c:12]>>[CH3;D1;+0:1]-[O;H0;D2;+0:8]-[C;H0;D4;+0:7]1(-[c:9](:[c:10]):[c:11])-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5]:[c:6]-1:[c:12] | null | [] | null | null | null | null | A mixture of 6.3 g of 2-(4-dimethylaminophenyl)carbonyl-5-dimethylaminobenzoic acid and 150.0 ml of acetic anhydride was stirred for approximately fifteen minutes at ambient temperature. Slowly, 10.0 ml of piperidine and 10.0 ml of methyl alcohol were added to the mixture. Two grams of potassium hydroxide was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carboxylic acid.Ketone | Ester.Ether | null | c1ccc2c(c1)COC2 | c1ccccc1.c1ccc2c(c1)COC2 | HO- | C1(=CC=CC=C1)C.CO | null | null | CC(=O)OC(C)=O.CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1>C1(=CC=CC=C1)C.CO>COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a810024a81c5474486c77da724e3fcd8 | CCN(CC)c1ccc(C(=O)c2ccccc2C(=O)O)c(C)c1.O=C/C(Cl)=C(/Cl)C(=O)O.O=S(Cl)Cl>>CCN(CC)c1ccc(C2(OC3OC(=O)C(Cl)=C3Cl)OC(=O)c3ccccc32)c(C)c1 | N1=CC=CC=C1.CC1=C(C=CC(=C1)N(CC)CC)C(=O)C1=C(C(=O)O)C=CC=C1.S(=O)(Cl)Cl.C(/C(/Cl)=C(/Cl)\C=O)(=O)O>>ClC=1C(OC(C1Cl)OC1(OC(=O)C2=CC=CC=C12)C1=C(C=C(C=C1)N(CC)CC)C)=O | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[c:28]2[c:23]([C:21]([OH:20])=[O:22])[cH:24][cH:25][cH:26][cH:27]2)[c:29]([CH3:30])[cH:31]1.O=[C:16](O)/[C:14]([Cl:17])=[C:18](\[CH:12]=[O:13])[Cl:19].ClS(Cl)=[O:15]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([C:10]2([O:11][CH:12... | CCN(CC)c1ccc(C(=O)c2ccccc2C(=O)O)c(C)c1.O=C/C(Cl)=C(/Cl)C(=O)O.O=S(Cl)Cl | CCN(CC)c1ccc(C2(OC3OC(=O)C(Cl)=C3Cl)OC(=O)c3ccccc32)c(C)c1 | null | null | C(CCl)Cl | C-C Coupling | OtherReaction | 9e8a5cecbd285525c46fb0e84b3c103f13ddd5e4f6e4b45059a2b091a780fcc8 | aed12b4a1476e3f519194cd55f841f4c179537b604db6e776b2b137e0f7f8582 | O=C1C=CC(OC2(c3ccccc3)OC(=O)c3ccccc32)O1 | Cl-S(-Cl)=[O;H0;D1;+0:1].O-[C;H0;D3;+0:2](=O)/[C;H0;D3;+0:3](-[Cl;H0;D1;+0:4])=[C;H0;D3;+0:5](/[Cl;D1;H0:6])-[CH;D2;+0:7]=[O;H0;D1;+0:8].[O;D1;H0:9]=[C:10](-[OH;D1;+0:11])-[c:12]:[c:13](-[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-[c:16](:[c:17]):[c:18]):[c:19]>>[Cl;D1;H0:6]-[C;H0;D3;+0:5]1=[C;H0;D3;+0:2](-[Cl;H0;D1;+0:4])-[C;H0... | 84.2 | [{"value": 84.2, "product": "ClC=1C(OC(C1Cl)OC1(OC(=O)C2=CC=CC=C12)C1=C(C=C(C=C1)N(CC)CC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 1 above, 2.0 g of 2-(2-methyl-4-diethylaminophenyl)carbonylbenzoic acid, 0.77 g of thionyl chloride and 1.1 g of mucochloric acid were interacted in 20.0 ml of ethylene dichloride in the presence of 0.8 ml of pyridine to obtain 2.5 g of 3-[3,4-dichloro-2(5H)-furanon-5-yl... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Aldehyde.Carboxylic acid.Carboxylic acid.Ketone | Alkenyl halide.Alkenyl halide.Ester.Ester.Ether | null | C1=CCOC1.c1ccc2c(c1)COC2 | c1ccccc1.C1=CCOC1.c1ccc2c(c1)COC2 | HCl | C(CCl)Cl | null | null | CCN(CC)c1ccc(C(=O)c2ccccc2C(=O)O)c(C)c1.O=C/C(Cl)=C(/Cl)C(=O)O.O=S(Cl)Cl>C(CCl)Cl>CCN(CC)c1ccc(C2(OC3OC(=O)C(Cl)=C3Cl)OC(=O)c3ccccc32)c(C)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8f2a46ac08b540f895adb954e2d1b4c0 | CN(C)c1ccc(C(=O)c2ccccc2C(=O)O)cc1.CO>>COC1(c2ccc(N(C)C)cc2)OC(=O)c2ccccc21 | CN(C1=CC=C(C=C1)C(=O)C1=C(C(=O)O)C=CC=C1)C.S(=O)(Cl)Cl.CO.N1CCCCC1>>COC1(OC(=O)C2=CC=CC=C12)C1=CC=C(C=C1)N(C)C | O=[C:3]([c:4]1[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[c:21]1[c:16]([C:14]([OH:13])=[O:15])[cH:17][cH:18][cH:19][cH:20]1.[CH3:1][OH:2]>>[CH3:1][O:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]2)[O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | CN(C)c1ccc(C(=O)c2ccccc2C(=O)O)cc1.CO | COC1(c2ccc(N(C)C)cc2)OC(=O)c2ccccc21 | null | null | C(CCl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f9feffcf04aa5ebf5f9b0c2acbcad6329f27f6d55c577666e13776d073be7e05 | 12a26a0c5edf61d8688eaa18273b8b77287b4b3c05f7626d937998be3f42715d | O=C1OC(c2ccccc2)c2ccccc21 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7])-[c:8](:[c:9]):[c:10].[C;D1;H3:11]-[OH;D1;+0:12]>>[C;D1;H3:11]-[O;H0;D2;+0:12]-[C;H0;D4;+0:1]1(-[c:8](:[c:9]):[c:10])-[O;H0;D2;+0:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2]-1:[c:3] | null | [] | null | null | null | null | Following a procedure similar to that described in Example 1 above, 4.5 g of 2-(4-dimethylaminophenyl)carbonylbenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of piperidine at ambient temperature for approximately ten minut... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Methanol | Ester.Ether | null | c1ccc2c(c1)COC2 | c1ccccc1.c1ccc2c(c1)COC2 | HO- | C(CCl)Cl | null | null | CN(C)c1ccc(C(=O)c2ccccc2C(=O)O)cc1.CO>C(CCl)Cl>COC1(c2ccc(N(C)C)cc2)OC(=O)c2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-19d90ab0c1644f2d9508609f312bd603 | CCN(CC)c1ccc(C(=O)c2ccccc2C(=O)O)c(C)c1.CO>>CCN(CC)c1ccc(C2(OC)OC(=O)c3ccccc32)c(C)c1 | N1=CC=CC=C1.CC1=C(C=CC(=C1)N(CC)CC)C(=O)C1=C(C(=O)O)C=CC=C1.S(=O)(Cl)Cl.CO>>COC1(OC(=O)C2=CC=CC=C12)C1=C(C=C(C=C1)N(CC)CC)C | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[c:21]2[c:16]([C:14]([OH:13])=[O:15])[cH:17][cH:18][cH:19][cH:20]2)[c:22]([CH3:23])[cH:24]1.O[CH3:12]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([C:10]2([O:11][CH3:12])[O:13][C:14](=[O:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21... | CCN(CC)c1ccc(C(=O)c2ccccc2C(=O)O)c(C)c1.CO | CCN(CC)c1ccc(C2(OC)OC(=O)c3ccccc32)c(C)c1 | null | null | C(CCl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f9feffcf04aa5ebf5f9b0c2acbcad6329f27f6d55c577666e13776d073be7e05 | 12a26a0c5edf61d8688eaa18273b8b77287b4b3c05f7626d937998be3f42715d | O=C1OC(c2ccccc2)c2ccccc21 | O-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]):[c:12]>>[CH3;D1;+0:1]-[O;H0;D2;+0:8]-[C;H0;D4;+0:7]1(-[c:9](:[c:10]):[c:11])-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5]:[c:6]-1:[c:12] | null | [] | null | null | null | null | Proceeding in a manner similar to that described in Example 1 above, 5.2 g of 2-(2-methyl-4-diethylaminophenyl)carbonylbenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of pyridine to obtain 2.5 g of 3-methoxy-3-(2-methyl-4-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Methanol | Ester.Ether | null | c1ccc2c(c1)COC2 | c1ccccc1.c1ccc2c(c1)COC2 | HO- | C(CCl)Cl | null | null | CCN(CC)c1ccc(C(=O)c2ccccc2C(=O)O)c(C)c1.CO>C(CCl)Cl>CCN(CC)c1ccc(C2(OC)OC(=O)c3ccccc32)c(C)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-43ea8ae32d9646759c4d368ad904a617 | CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1.CO>>COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 | CN(C1=CC=C(C=C1)C(=O)C1=C(C(=O)O)C=C(C=C1)N(C)C)C.S(=O)(Cl)Cl.CO.N1=CC=CC=C1>>COC1(OC(=O)C2=CC(=CC=C12)N(C)C)C1=CC=C(C=C1)N(C)C | O=[C:3]([c:4]1[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[c:24]1[c:16]([C:14]([OH:13])=[O:15])[cH:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1.[CH3:1][OH:2]>>[CH3:1][O:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]2)[O:13][C:14](=[O:15])[c:16]2[cH:17][c:18]([N:19]([CH3:20])[C... | CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1.CO | COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 | null | null | C(CCl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f9feffcf04aa5ebf5f9b0c2acbcad6329f27f6d55c577666e13776d073be7e05 | 12a26a0c5edf61d8688eaa18273b8b77287b4b3c05f7626d937998be3f42715d | O=C1OC(c2ccccc2)c2ccccc21 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7])-[c:8](:[c:9]):[c:10].[C;D1;H3:11]-[OH;D1;+0:12]>>[C;D1;H3:11]-[O;H0;D2;+0:12]-[C;H0;D4;+0:1]1(-[c:8](:[c:9]):[c:10])-[O;H0;D2;+0:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2]-1:[c:3] | null | [] | null | null | null | null | In a manner similar to that described in Example 1 above, 5.2 g of 2-(4-dimethylaminophenyl)carbonyl-5-dimethylaminobenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of pyridine at ambient temperature overnight to obtain 4.5... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Methanol | Ester.Ether | null | c1ccc2c(c1)COC2 | c1ccccc1.c1ccc2c(c1)COC2 | HO- | C(CCl)Cl | null | null | CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1.CO>C(CCl)Cl>COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e9cef888cfe447b9a68601f054b7153b | CCn1c(C)c(C(=O)c2ccccc2C(=O)O)c2ccccc21.CO>>CCn1c(C)c(C2(OC)OC(=O)c3ccccc32)c2ccccc21 | N1=CC=CC=C1.C(C)N1C(=C(C2=CC=CC=C12)C(=O)C1=C(C(=O)O)C=CC=C1)C.S(=O)(Cl)Cl.CO>>COC1(OC(=O)C2=CC=CC=C12)C1=C(N(C2=CC=CC=C12)CC)C | O=[C:7]([c:6]1[c:4]([CH3:5])[n:3]([CH2:2][CH3:1])[c:24]2[c:19]1[cH:20][cH:21][cH:22][cH:23]2)[c:18]1[c:13]([C:11]([OH:10])=[O:12])[cH:14][cH:15][cH:16][cH:17]1.[OH:8][CH3:9]>>[CH3:1][CH2:2][n:3]1[c:4]([CH3:5])[c:6]([C:7]2([O:8][CH3:9])[O:10][C:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[c:19]2[cH:20][cH:21... | CCn1c(C)c(C(=O)c2ccccc2C(=O)O)c2ccccc21.CO | CCn1c(C)c(C2(OC)OC(=O)c3ccccc32)c2ccccc21 | null | null | C(CCl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f9feffcf04aa5ebf5f9b0c2acbcad6329f27f6d55c577666e13776d073be7e05 | 12a26a0c5edf61d8688eaa18273b8b77287b4b3c05f7626d937998be3f42715d | O=C1OC(c2c[nH]c3ccccc23)c2ccccc21 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7])-[c:8]1:[c:9]:[c:10]:[#7;a:11](-[C:12]):[c:13]:1-[C;D1;H3:14].[C;D1;H3:15]-[OH;D1;+0:16]>>[C:12]-[#7;a:11]1:[c:10]:[c:9]:[c:8](-[C;H0;D4;+0:1]2(-[O;H0;D2;+0:16]-[C;D1;H3:15])-[O;H0;D2;+0:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2]-2:[c:3]):[c:13]:1-[C;D1;H3:... | null | [] | null | null | null | null | Proceeding in a manner similar to that described in Example 1 above, 5.1 g of 2-(1-ethyl-2-methylindol-3-yl)carbonylbenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 ml of ethylene dichloride in the presence of 1.3 ml of pyridine to obtain 2.1 g of 3-methoxy-3-(1-ethyl-2-meth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Methanol | Ester.Ether | null | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2.c1cc2ccccc2[nH]1 | HO- | C(CCl)Cl | null | null | CCn1c(C)c(C(=O)c2ccccc2C(=O)O)c2ccccc21.CO>C(CCl)Cl>CCn1c(C)c(C2(OC)OC(=O)c3ccccc32)c2ccccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1aa94ad3e2534bfdbb80782c5620c2cb | CC(=O)O.CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1>>COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 | [OH-].[NH4+].C(C)(=O)OC(C)=O.C(C)(=O)O.CN(C1=CC=C(C=C1)C(=O)C1=C(C(=O)O)C=C(C=C1)N(C)C)C>>COC1(OC(=O)C2=CC(=CC=C12)N(C)C)C1=CC=C(C=C1)N(C)C | O=C(O)[CH3:1].[O:2]=[C:3]([c:4]1[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[c:24]1[c:16]([C:14]([OH:13])=[O:15])[cH:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([N:8]([CH3:9])[CH3:10])[cH:11][cH:12]2)[O:13][C:14](=[O:15])[c:16]2[cH:17][c:18]([N:19]([CH3:20... | CC(=O)O.CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1 | COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 | null | null | C1(=CC=CC=C1)C.CO | Heteroatom Alkylation and Arylation | OtherReaction | 20d3ebc0682c57632becbe678a7ca19da9dac565710e494256fb6aeb31437396 | 7b5f381e55f8adac8972daeb972c7a1c99acaba913b25c686a96df3348bce8e0 | O=C1OC(c2ccccc2)c2ccccc21 | O-C(=O)-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]):[c:12]>>[CH3;D1;+0:1]-[O;H0;D2;+0:8]-[C;H0;D4;+0:7]1(-[c:9](:[c:10]):[c:11])-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5]:[c:6]-1:[c:12] | null | [] | 47 | CELSIUS | null | null | To a stirred mixture of 30.0 ml of acetic anhydride and 15.0 ml of glacial acetic acid there was added gradually 5.0 g of 2-(4-dimethylaminophenyl)carbonyl-5-dimethylaminobenzoic acid. The reaction mixture was heated slowly to approximately 47° C. and maintained at a temperature in the range of 45° to 50° C. for approx... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ketone | Ester.Ether | null | c1ccc2c(c1)COC2 | c1ccccc1.c1ccc2c(c1)COC2 | HO- | C1(=CC=CC=C1)C.CO | 47 | null | CC(=O)O.CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2C(=O)O)cc1>C1(=CC=CC=C1)C.CO>COC1(c2ccc(N(C)C)cc2)OC(=O)c2cc(N(C)C)ccc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-97027fce6f1e4875ac3ae1510fc2b45f | CC(C)CCI.c1ccc2cnccc2c1>>CC(C)CC[n+]1ccc2ccccc2c1.[I-] | C(CC(C)C)I.C1=NC=CC2=CC=CC=C12>>[I-].C(CC(C)C)[N+]1=CC2=CC=CC=C2C=C1 | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][I:16].[n:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][n+:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1.[I-:16] | CC(C)CCI.c1ccc2cnccc2c1 | CC(C)CC[n+]1ccc2ccccc2c1.[I-] | null | null | C(C)O | Functional Group Interconversion | OtherReaction | c63f1f397f499ce78ae56f5ee18af026b0e8fcca7137567d0130c126ce0be3ad | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc2c[nH+]ccc2c1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[I;H0;D1;+0:4].[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8]:[c:9]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[n+;H0;D3:7](:[c:6]:[c:5]):[c:8]:[c:9].[I-;H0;D0:4] | 91 | [{"value": 91.0, "product": "[I-].C(CC(C)C)[N+]1=CC2=CC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 15.3 g of isoamyliodide and 10 g of isoquinoline placed in a four-necked flask equipped with a reflux condenser and mechanical stirrer was added 30 ml of ethanol. The mixture was reacted for 3 hours under reflux. When the reaction was completed, ethanol was removed from the reaction mixture under reduced pressure, t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2cnccc2c1 | C1=[NH+]C=c2ccccc2=C1 | C1=[NH+]C=c2ccccc2=C1 | null | C(C)O | null | null | CC(C)CCI.c1ccc2cnccc2c1>C(C)O>CC(C)CC[n+]1ccc2ccccc2c1.[I-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bb97313df20841e593595712f8498a7c | N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1>>N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1 | [I-].C(CC(C)C)[N+]1=CC2=CC=CC=C2C=C1.C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N.C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N>>C(CC(C)C)[N+]1=CC2=CC=CC=C2C=C1.C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N | [N:16]#[C:17][C:18]([C:19]#[N:20])=[c:21]1[cH:22][cH:23][c:24](=[C:25]([C:26]#[N:27])[C:28]#[N:29])[cH:30][cH:31]1>>[N:16]#[C:17][C:18]([C:19]#[N:20])=[c:21]1[cH:22][cH:23][c:24](=[C:25]([C:26]#[N:27])[C:28]#[N:29])[cH:30][cH:31]1 | N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1 | N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C=c1ccc(=C)cc1 | null | null | [] | 5 | CELSIUS | null | null | To 15.3 g of isoamyliodide and 10 g of isoquinoline placed in a four-necked flask equipped with a reflux condenser and mechanical stirrer was added 30 ml of ethanol. The mixture was reacted for 3 hours under reflux. When the reaction was completed, ethanol was removed from the reaction mixture under reduced pressure, t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)#N | 5 | null | N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1>C(C)#N>N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3173c8608eef49989521d6454a2d815e | CN1CC(O)N(c2cc(C(C)(C)C)on2)C1=O.OCS>>CSC1CN(C)C(=O)N1c1cc(C(C)(C)C)on1 | SCO.C(C)(C)(C)C1=CC(=NO1)N1C(N(CC1O)C)=O.C1(=CC=C(C=C1)S(=O)(=O)O)C.SCO>>C(C)(C)(C)C1=CC(=NO1)N1C(N(CC1SC)C)=O | O[CH:3]1[CH2:4][N:5]([CH3:6])[C:7](=[O:8])[N:9]1[c:10]1[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[o:17][n:18]1.O[CH2:1][SH:2]>>[CH3:1][S:2][CH:3]1[CH2:4][N:5]([CH3:6])[C:7](=[O:8])[N:9]1[c:10]1[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[o:17][n:18]1 | CN1CC(O)N(c2cc(C(C)(C)C)on2)C1=O.OCS | CSC1CN(C)C(=O)N1c1cc(C(C)(C)C)on1 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 6ebff92bf0d453922eabbc2c83d8de4614320072c750e35cdd58c01a9a99068a | 75fa9b34af5fe851c34cba67126ce3452e1d9f7b11a3896da2bcf677caa017b1 | O=C1NCCN1c1ccon1 | O-[CH2;D2;+0:1]-[SH;D1;+0:2].O-[CH;D3;+0:3]1-[C:4]-[#7:5](-[C;D1;H3:6])-[C:7](=[O;D1;H0:8])-[#7:9]-1-[c:10]:[#7;a:11]:[#8;a:12]>>[#8;a:12]:[#7;a:11]:[c:10]-[#7:9]1-[C:7](=[O;D1;H0:8])-[#7:5](-[C;D1;H3:6])-[C:4]-[CH;D3;+0:3]-1-[S;H0;D2;+0:2]-[CH3;D1;+0:1] | null | [] | null | null | 17 | HOUR | To a three-necked flask provided with a magnetic stirring bar, dry-ice/acetone condenser and a gas inlet tube were charged 70 grams of 3-(5-t-butyl-3-isoxazolyl)-1-methyl-4-hydroxy-2-imidazolidinone, 5.0 grams of p-toluene sulfonic acid and 700 milliliters of t-butanol. A slow stream of gaseous mercaptomethanol was int... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol.Aliphatic thiol | Monosulfide | C1C[NH]C[NH]1 | C1C[NH]C[NH]1 | C1C[NH]C[NH]1.c1cnoc1 | HO- | C(C)(C)(C)O | null | 17 | CN1CC(O)N(c2cc(C(C)(C)C)on2)C1=O.OCS>C(C)(C)(C)O>CSC1CN(C)C(=O)N1c1cc(C(C)(C)C)on1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-92a52f538f554a5093be7b8af150e8d1 | CN(C)C(=O)Nc1ccc(Cl)c(Cl)c1.ClP(Cl)(Cl)(Cl)Cl>>CN(C)C(Cl)=Nc1ccc(Cl)c(Cl)c1 | P(Cl)(Cl)(Cl)(Cl)Cl.CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)C>>CN(C(=NC1=CC(=C(C=C1)Cl)Cl)Cl)C | O=[C:4]([N:2]([CH3:1])[CH3:3])[NH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1.ClP(Cl)(Cl)(Cl)[Cl:5]>>[CH3:1][N:2]([CH3:3])[C:4]([Cl:5])=[N:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1 | CN(C)C(=O)Nc1ccc(Cl)c(Cl)c1.ClP(Cl)(Cl)(Cl)Cl | CN(C)C(Cl)=Nc1ccc(Cl)c(Cl)c1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 60811a9caeffe3d7277a657d28cc3d7288798240356f6a4e5c5bb54c29d56f23 | 66b9fb05d7a69612663ae5fba3e0f1846fd695bde064e1987943ce282973d411 | c1ccccc1 | Cl-P(-Cl)(-Cl)(-Cl)-[Cl;H0;D1;+0:1].O=[C;H0;D3;+0:2](-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[#7:7](-[C;D1;H3:8])-[C;D1;H3:9]>>[C;D1;H3:8]-[#7:7](-[C;D1;H3:9])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 100.2 | [{"value": 100.2, "product": "CN(C(=NC1=CC(=C(C=C1)Cl)Cl)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10.4 g (0.05 mole) of phosphorus pentachloride and 11.6 g (0.05 mole) of N,N-dimethyl-N'-(3,4-dichlorophenyl)-urea in 74 ml of toluene are refluxed for 3 hours, and the volatile components are distilled off under 0.13 mbar to give 12.6 g of N,N-dimethyl-N'-(3,4-dichlorophenyl)-chloroformamidine in the form of an oil; n... | 10.6084/m9.figshare.5104873.v1 | null | Urea | Alkenyl halide | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | CN(C)C(=O)Nc1ccc(Cl)c(Cl)c1.ClP(Cl)(Cl)(Cl)Cl>C1(=CC=CC=C1)C>CN(C)C(Cl)=Nc1ccc(Cl)c(Cl)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-696211169c204a97a942d3f05a95269f | C#CC(C)(C)O.Cc1cc(Cl)nc(N)n1>>CC(O)C#CC1(C)C=CN=C(N)N1 | NC1=NC(=CC(=N1)Cl)C.CC(C)(C#C)O.O1CCCC1>>NC1=NC=CC(N1)(C)C#CC(C)O | C[C:2]([CH3:1])([OH:3])[C:4]#[CH:5].Cl[c:9]1[cH:8][c:6]([CH3:7])[n:13][c:11]([NH2:12])[n:10]1>>[CH3:1][CH:2]([OH:3])[C:4]#[C:5][C:6]1([CH3:7])[CH:8]=[CH:9][N:10]=[C:11]([NH2:12])[NH:13]1 | C#CC(C)(C)O.Cc1cc(Cl)nc(N)n1 | CC(O)C#CC1(C)C=CN=C(N)N1 | null | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | C(C)N(CC)CC | C-C Coupling | OtherReaction | e4534ad455f776132e42f7d032b381e6608776ff6a4569d907eebaec4b6f33de | e1f59202490f2a6fed0765cc82d706b5485139e5b892c2ce311783c619ecb20a | C1=CN=CNC1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[O;D1;H1:3])-[C:4]#[CH;D1;+0:5].Cl-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C;D1;H3:9]):[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[N;D1;H2:12]):[n;H0;D2;+0:13]:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[O;D1;H1:3])-[C:4]#[C;H0;D2;+0:5]-[C;H0;D4;+0:8]1(-[C;D1;H3:9])-[CH;D2;+0:7]=[CH;D2;+0:6]-[N;H0;D2;+0:1... | null | [] | null | null | null | null | A mixture of 10.0 g of 2-amino-4-chloro-6-methylpyrimidine, 8.8 ml of 2-methyl-3-butyn-2-ol, 400 ml of tetrahydrofuran (THF), 0.06 g of copper (I) iodide, 0.5 g of bis(triphenylphosphine)palladium (II) chloride and 20.4 ml of triethylamine was heated overnight at reflux under a nitrogen atmosphere. The reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary alcohol.Alkyne | Secondary alcohol.Secondary amine.Alkyne | c1cncnc1 | C1=CN=CNC1 | C1=CN=CNC1 | HCl | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)N(CC)CC | null | null | C#CC(C)(C)O.Cc1cc(Cl)nc(N)n1>[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)N(CC)CC>CC(O)C#CC1(C)C=CN=C(N)N1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bc4fd103bc7e48e291eff8e257739a7b | CC(O)C#CC1(C)C=CN=C(N)N1>>C#Cc1cc(C)nc(N)n1 | NC1=NC=CC(N1)(C)C#CC(C)O.[OH-].[Na+].O1CCOCC1>>NC1=NC(=CC(=N1)C#C)C | CC(O)[C:1]#[C:2][C:3]1([CH3:6])[CH:4]=[CH:5][N:7]=[C:8]([NH2:9])[NH:10]1>>[CH:1]#[C:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:10]1 | CC(O)C#CC1(C)C=CN=C(N)N1 | C#Cc1cc(C)nc(N)n1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 045f842bbe8ec6f6d524e1a82536d42e0ff6be0930be4cd6512994b280a350d6 | d1dbf24a45f015ac7d2d81e2b7ccc9adc57d756a2cda65f79664152407f61239 | c1cncnc1 | C-C(-O)-[C;H0;D2;+0:1]#[C:2]-[C;H0;D4;+0:3]1(-[CH3;D1;+0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[N;H0;D2;+0:7]=[C;H0;D3;+0:8](-[N;D1;H2:9])-[NH;D2;+0:10]-1>>[CH3;D1;+0:4]-[c;H0;D3;+0:6]1:[cH;D2;+0:5]:[c;H0;D3;+0:3](-[C:2]#[CH;D1;+0:1]):[n;H0;D2;+0:10]:[c;H0;D3;+0:8](-[N;D1;H2:9]):[n;H0;D2;+0:7]:1 | null | [] | null | null | null | null | A mixture of 4.44 g of 4-(2-amino-4-methylpyrimidin-4-yl)-3-butyne-2-ol, 1 g of sodium hydroxide, 5 ml of dioxane and 50 ml of toluene was refluxed for two hours. The toluene layer was decanted from the residue, concentrated under reduced pressure and chromatographed on a silica gel dry column. The product band eluted ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine.Alkyne | Alkyne | C1=CN=CNC1 | c1cncnc1 | c1cncnc1 | HO- | C1(=CC=CC=C1)C | null | null | CC(O)C#CC1(C)C=CN=C(N)N1>C1(=CC=CC=C1)C>C#Cc1cc(C)nc(N)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cd5e2fced7ff400abb7abbacc0c0e028 | C=Cc1cc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O>>C#Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC)n1 | NC1=NC(=CC(=N1)C=C)C.C(=O)(OC)C1=C(C=CC=C1)S(=O)(=O)N=C=O.ClCCl>>C(#C)C1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1 | [CH2:1]=[CH:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:26]1.[C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22](=[O:23])[O:24][CH3:25]>>[CH:1]#[C:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:2... | C=Cc1cc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O | C#Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC)n1 | null | null | C(CCC)Cl | Acylation | OtherReaction | 1f92dde865e07ec146074863c12594338e8987df22d9bd59d98ce20669c89c71 | dd2d746c472a7d035c6e8e9104e673f320ded95fa202dc929fc9d0395c6ae0c9 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5](-[NH2;D1;+0:6]):[#7;a:7]:[c:8]:[c:9]:1.[O;D1;H0:10]=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[#16:13](=[O;D1;H0:14])(=[O;D1;H0:15])-[c:16]>>[CH;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[NH;D2;+0:12]-[#16:13](=[O;D1;H0:14])(=[O;D1;... | 84.2 | [{"value": 84.2, "product": "C(#C)C1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | In a dry flask under a nitrogen atmosphere was mixed 0.24 g of 2-amino-4-ethenyl-6-methylpyrimidine, 0.61 g of 2-carbomethoxybenzenesulfonylisocyanate and 25 ml of dry dichloromethane. The solution was heated to reflux for five minutes and allowed to stir at room temperature overnight. A precipitate formed. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Vinyl | Sulfonamide.Urea.Alkyne | null | null | c1cncnc1.c1ccccc1 | null | C(CCC)Cl | null | 8 | C=Cc1cc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O>C(CCC)Cl>C#Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-12c266befdb54ca28cb9b7f267717d8c | CSC(=NS(=O)(=O)c1ccccc1Cl)Nc1nc(C)cc(C)n1.NO>>Cc1cc(C)nc(NC(=NO)NS(=O)(=O)c2ccccc2Cl)n1 | ClC1=C(C=CC=C1)S(=O)(=O)N=C(NC1=NC(=CC(=N1)C)C)SC.Cl.NO.C(C)(=O)[O-].[Na+]>>ClC1=C(C=CC=C1)S(=O)(=O)NC(=NO)NC1=NC(=CC(=N1)C)C | CS[C:9]([NH:8][c:7]1[n:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[n:23]1)=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[Cl:22].[NH2:10][OH:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9](=[N:10][OH:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[n:... | CSC(=NS(=O)(=O)c1ccccc1Cl)Nc1nc(C)cc(C)n1.NO | Cc1cc(C)nc(NC(=NO)NS(=O)(=O)c2ccccc2Cl)n1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | bfefe9a971f821a544f44ae0b50298c9d00b30ea619e32efc239d5f059d9cdab | 38c94484faab7afee752647a77b11f0e76d2633d5a09c90ce6faca4c32f14ac7 | N=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | C-S-[C;H0;D3;+0:1](-[#7:2]-[c:3](:[#7;a:4]):[#7;a:5])=[N;H0;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10].[NH2;D1;+0:11]-[O;D1;H1:12]>>[#7;a:4]:[c:3](-[#7:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:11]-[O;D1;H1:12])-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]):[#7;a:5] | 62.5 | [{"value": 62.5, "product": "ClC1=C(C=CC=C1)S(=O)(=O)NC(=NO)NC1=NC(=CC(=N1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 0.5 g of methyl N'-(2-chlorophenylsulfonyl)-N-(4,6-dimethylpyrimdin-2-yl)carbamimidothioate in 10 ml of tetrahydrofuran was added 0.3 g of hydroxylamine hydrochloride and 0.3 g of sodium acetate. The mixture was stirred at room temperature for 2 hours, whereupon the product was precipitated with ice-wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Sulfonamide.Oxime | null | null | c1cncnc1.c1ccccc1 | Other | O1CCCC1 | null | 2 | CSC(=NS(=O)(=O)c1ccccc1Cl)Nc1nc(C)cc(C)n1.NO>O1CCCC1>Cc1cc(C)nc(NC(=NO)NS(=O)(=O)c2ccccc2Cl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-678a5f2cc6bf4bd19684d016bda9dfe7 | Cc1cc(C)nc(NC#N)n1.S>>Cc1cc(C)nc(NC(N)=S)n1 | C(Cl)Cl.S.C(#N)NC1=NC(=CC(=N1)C)C.S>>CC1=NC(=NC(=C1)C)NC(=S)N | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9]#[N:10])[n:12]1.[SH2:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9]([NH2:10])=[S:11])[n:12]1 | Cc1cc(C)nc(NC#N)n1.S | Cc1cc(C)nc(NC(N)=S)n1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | ed78cdf70c0f89f7e5fe39f0ed4af5a67574ff4b674472eafe0747ed664a3d35 | d0f3787c02b5b5fa4087cb14d3ee90e3b6c138b2fe7523599b12f5add1514ca6 | c1cncnc1 | [#7;a:1]:[c:2](-[#7:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]):[#7;a:6].[SH2;D0;+0:7]>>[#7;a:1]:[c:2](-[#7:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[S;H0;D1;+0:7]):[#7;a:6] | null | [] | null | null | 1 | HOUR | A suspension of 10 g of 2-cyanoamino-4,6-dimethylpyrimidine in 50 ml of pyridine was saturated with hydrogen sulfide and stored for 1 hour at 25°. The H2S treatment was repeated twice more, and the mixture was allowed to stir at 25° for 16 hours. Methylene chloride was added, and the product was filtered and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide | Thiourea | null | null | c1cncnc1 | null | N1=CC=CC=C1 | null | 1 | Cc1cc(C)nc(NC#N)n1.S>N1=CC=CC=C1>Cc1cc(C)nc(NC(N)=S)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a40805c7071b481f815b33baed5200e6 | COc1cc(C)nc(NC(=S)NNC(=O)c2ccccc2)n1>>COc1cc(C)nc(NC(N)=S)n1 | COC1=NC(=NC(=C1)C)NC(=S)NNC(C1=CC=CC=C1)=O.[OH-].[Na+].Cl>>COC1=NC(=NC(=C1)C)NC(=S)N | O=C(N[NH:11][C:10]([NH:9][c:8]1[n:7][c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[n:13]1)=[S:12])c1ccccc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10]([NH2:11])=[S:12])[n:13]1 | COc1cc(C)nc(NC(=S)NNC(=O)c2ccccc2)n1 | COc1cc(C)nc(NC(N)=S)n1 | null | null | null | Reduction | OtherReaction | b74d85043f2fa063af8c5e9cf50c05c234a057e2439c6fb551e5d0929a6d1011 | 5ef4e140eaf2e2141dfa542de18c071153f90971893f54ba2cf40de8cb0ac817 | c1cncnc1 | O=C(-N-[NH;D2;+0:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[c:5](:[#7;a:6]):[#7;a:7])-c1:c:c:c:c:c:1>>[#7;a:6]:[c:5](-[#7:4]-[C:2](-[NH2;D1;+0:1])=[S;D1;H0:3]):[#7;a:7] | 102.5 | [{"value": 102.5, "product": "COC1=NC(=NC(=C1)C)NC(=S)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 25 g of the compound from Example 3 and 55 ml of 10% aqueous sodium hydroxide was heated on the steam bath for 30 minutes, cooled, neutralized with aqueous HCl to pH 8, filtered, washed with water, dried by suction, and washed with ether to afford 16 g of the title compound, m.p. 220° d.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Thiourea | Thiourea | c1ccccc1 | null | c1cncnc1 | HO- | null | null | null | COc1cc(C)nc(NC(=S)NNC(=O)c2ccccc2)n1>>COc1cc(C)nc(NC(N)=S)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9e4ab9bb60124a2eb95bb9f736b4bfaa | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(C)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 | NC1=NC(=CC(=N1)C)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>CC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([CH3:21])[cH:22][c:23]([CH3:24])[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20]([CH3:21])... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(C)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | To 37 g. of 2-amino-4,6-dimethylpyrimidine in 500 ml of anhydrous acetonitrile was added 67 g of 2-methoxycarbonylbenzenesulfonylisocyanate with stirring at ambient temperatures. The resulting mixture was thereafter stirred for sixteen hours and then filtered to remove the desired product which had precipitated as a wh... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(C)#N | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(C)nc(N)n1>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-769634cdbbf7463d91bb9643312df044 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1ncccn1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1ncccn1 | NC1=NC=CC=N1.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>N1=C(N=CC=C1)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][cH:20][cH:21][cH:22][n:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][cH:20][cH:21][cH:22][n:23]1 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1ncccn1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1ncccn1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | 65.7 | [{"value": 65.7, "product": "N1=C(N=CC=C1)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | With stirring at ambient temperature, 1.0 g of 2-aminopyrimidine in 25 ml of anhydrous acetonitrile was added to 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring that mixture for 24 hours, the resultant precipitate was filtered off to yield 2.2 g of the desired compound which melted at 188°-192°. Its... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(C)#N | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Nc1ncccn1>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1ncccn1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1d54cc81eba14da0a16f1e27f919872c | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(C)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | NC1=NC(=CC(=N1)OC)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([CH3:21])[cH:22][c:23]([O:24][CH3:25])[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20]([CH... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(C)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | 21.1 | [{"value": 21.1, "product": "COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrous methylene chloride was added at ambient temperature 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring for 16 hours, the foregoing mixture was filtered to remove unreacted amine, and the filtrate evaporated a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(Cl)Cl | null | 16 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(C)nc(N)n1>C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-61626fc7d5534f01883eebf809b6b0d7 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(OC)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 | [OH-].[Na+].NC1=NC(=CC(=N1)OC)OC.C(Cl)Cl.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([O:21][CH3:22])[cH:23][c:24]([O:25][CH3:26])[n:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:2... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(OC)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 | null | null | O | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | 43.1 | [{"value": 43.1, "product": "COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture containing 1.6 g of 2-amino-4,6-dimethoxypyrimidine, 30 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate was stirred at ambient temperature and pressure for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | O | null | 16 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1cc(OC)nc(N)n1>O>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1d93b740d37a45249a4e3a5411ee6423 | BrCc1ccccc1.Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1>>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCc2ccccc2)n1 | CC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C(=O)O)C=CC=C1.C(C)N(CC)CC.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC(=O)C1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=NC(=CC(=N1)C)C | Br[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9](=[O:10])[NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21](=[O:22])[OH:23])[n:31]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9](=[O:10])[NH:11][S:12](=[O:13])(=[O:14])[c... | BrCc1ccccc1.Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCc2ccccc2)n1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1C(=O)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]>>[O;D1;H0:5]=[C:6](-[c:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To 1.75 g of 2-(4,6-dimethylpyrimidin-2-ylaminocarbonylsulfamoyl)benzoic acid was added 0.51 g of triethylamine in 10 ml tetrahydrofuran and 0.88 g of benzyl bromide in 10 ml of tetrahydrofuran. The mixture was heated to reflux for 1.5 hours, filtered and the tetrahydrofuran evaporated in-vacuo. The residue was extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | null | BrCc1ccccc1.Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1>O1CCCC1>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCc2ccccc2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2d42eb4e371646ed84350a954967c4a8 | COc1nc(N)nc(OC)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)nc(OC)n1 | NC1=NC(=NC(=N1)OC)OC.ClCCOC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OCCCl | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:25][c:26]([O:27][CH3:28])[n:29]1.[C:7](=[O:8])=[N:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19](=[O:20])[O:21][CH2:22][CH2:23][Cl:24]>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][C:7](=[O:8])[NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:... | COc1nc(N)nc(OC)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl | COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | null | null | To 0.7 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(β-chloroethoxycarbonyl)benzenesulfonyl isocyanate. After stirring at ambient temperature for sixteen hours the solvent was removed under reduced pressure, the residue triturated with ether and the solid pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1nc(N)nc(OC)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>C(Cl)Cl>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-aca69c831ea64ea8a4344234fbcbb6c6 | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)n1 | NC1=NC(=NC(=N1)OC)C.ClCCOC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OCCCl | [CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:28]1.[C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22](=[O:23])[O:24][CH2:25][CH2:26][Cl:27]>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][... | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | 80.1 | [{"value": 80.1, "product": "COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 0.7 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(β-chloroethoxycarbonyl)benzenesulfonyl isocyanate with stirring at ambient temperature. The mixture was thereafter stirred for sixteen hours. The solvent was evaporated under reduced pressure and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | COc1nc(C)nc(N)n1.O=C=NS(=O)(=O)c1ccccc1C(=O)OCCCl>C(Cl)Cl>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OCCCl)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e171686f59644326b8423a8c6d2b385d | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)nc(OC)n1 | NC1=NC(=NC(=N1)OC)OC.C(C)(C)OC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C | [C:7](=[O:8])=[N:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19](=[O:20])[O:21][CH:22]([CH3:23])[CH3:24].[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:25][c:26]([O:27][CH3:28])[n:29]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][C:7](=[O:8])[NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][... | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1 | COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | 26.2 | [{"value": 26.2, "product": "COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 0.7 g of 2-amino-4,6-dimethoxy-1,3,5-triazine suspended in 5.0 ml anhydrous methylene chloride was added 1.6 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 5.0 ml anhydrous methylene chloride. The resulting mixture was filtered to remove some unreacted 2-amino-4,6-dimethoxytriazine, the methylene chloride fi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>C(Cl)Cl>COc1nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-635c0517f3744cbd8dfb588b31a8772f | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 | NC1=NC(=NC(=N1)OC)C.C(C)(C)OC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C | [C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22](=[O:23])[O:24][CH:25]([CH3:26])[CH3:27].[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:28]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18... | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1 | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | 51.1 | [{"value": 51.1, "product": "COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 26.8 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 300 ml anhydrous methylene chloride was added 67.0 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 100 ml anhydrous methylene chloride. The resultant suspension was stirred at ambient temperature for 72 hours, and filtered to yield 40.0 g of the desired p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ncncn1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>C(Cl)Cl>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-95e16a10e3ca47ff8d9163b6af78d34b | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | NC1=NC(=NC(=N1)OC)OC.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([O:21][CH3:22])[n:23][c:24]([O:25][CH3:26])[n:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | 16 | HOUR | A mixture of 1.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine, 25 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate was stirred at ambient temperature for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40° under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1ncncn1 | null | C(Cl)Cl | null | 16 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(N)nc(OC)n1>C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4700b6f180bd4a7db3b80c492d9e1560 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | NC1=NC(=NC(=N1)OC)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][c:20]([CH3:21])[n:22][c:23]([O:24][CH3:25])[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][c:20]([CH3... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | null | null | To an anhydrous suspension of 1.4 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 25 ml of methylene chloride was added with stirring at ambient temperature and pressure 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was thereafter stirred for 16 hours and filtered. The filtrate was evaporated to dr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1ncncn1 | null | C(Cl)Cl | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1>C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1272049606dc47cf8be4c43d2ac836f1 | CCCCC(C)O.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1>>CCCCC(C)OC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.CC(CCCC)O.C[Al](C)C>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(CCCC)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:6])[OH:7].CO[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[S:16](=[O:17])(=[O:18])[NH:19][C:20](=[O:21])[NH:22][c:23]1[n:24][c:25]([CH3:26])[n:27][c:28]([O:29][CH3:30])[n:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:6])[O:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:1... | CCCCC(C)O.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | CCCCC(C)OC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | c0c33fb70857974614ced096ed85cd9b1bb936117e81e0eac2307cf6764d59e0 | ee972764a3733e36048c715131dfbc8d317259bd5c7179f132b5465c9f9ff85f | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[OH;D1;+0:9]>>[C:6]-[C:7](-[C;D1;H3:8])-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 57.8 | [{"value": 57.8, "product": "COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC(CCCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 2-Hexanol (0.61 g) in 2 ml dry toluene was slowly added at room temperature to a solution of 1.5 ml (2M) trimethylaluminum diluted with 5.0 ml dry toluene under nitrogen. The mixture was stirrred at room temperature for 15 minutes and 0.95 g of N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylb... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Ester | null | null | c1ccccc1.c1ncncn1 | HO- | C1(=CC=CC=C1)C | null | 0.25 | CCCCC(C)O.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1>C1(=CC=CC=C1)C>CCCCC(C)OC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ab8071e9ff544daaa7243203fdd5d9d8 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1nnc(N)nc1C>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nnc(C)c(C)n1 | NC=1N=NC(=C(N1)C)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>CC=1N=C(N=NC1C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[n:19][n:20][c:21]([CH3:22])[c:23]([CH3:24])[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[n:19][n:20][c:21]([CH3... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1nnc(N)nc1C | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nnc(C)c(C)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1nccnn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1 | 70.8 | [{"value": 70.8, "product": "CC=1N=C(N=NC1C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a stirred suspension of 1.2 g of 3-amino-5,6-dimethyl-1,2,4-triazine in 25 ml of anhydrous acetonitrile was added at ambient temperature 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. After stirring for 24 hours at ambient temperature, the resultant precipitate was filtered off to yield 2.5 g of the desired co... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cnncn1 | null | C(C)#N | null | 24 | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1nnc(N)nc1C>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nnc(C)c(C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7122059c556d4c9ca5cb511975cd690a | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(N)nc(C)n1>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1cc(C)nc(C)n1 | NC1=NC(=NC(=C1)C)C.COC(=O)C1=C(C=CC=C1)S(=O)(=O)N=C=O>>CC1=NC(=CC(=N1)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16].[NH2:17][c:18]1[cH:19][c:20]([CH3:21])[n:22][c:23]([CH3:24])[n:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16])[NH:17][c:18]1[cH:19][c:20]([CH3:21]... | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(N)nc(C)n1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1cc(C)nc(C)n1 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | b2f9721fe12517bb4ddb059bee81df64632e89cc2635ea9f7de5f84d579af016 | ad01beb75a98e2ae01d9fc14d1face2625004bf1eae4aa0352da70e1110fdd06 | O=C(Nc1ccncn1)NS(=O)(=O)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | null | null | To a suspension of 1.2 g of 4-amino-2,6-dimethylpyrimidine in 30 ml of dry acetonitrile with stirring was added 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was stirred for two hours at ambient temperature, allowed to stand for sixteen hours and the desired product, which had precipitated, was remov... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonamide.Urea | null | null | c1ccccc1.c1cncnc1 | null | C(C)#N | null | null | COC(=O)c1ccccc1S(=O)(=O)N=C=O.Cc1cc(N)nc(C)n1>C(C)#N>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1cc(C)nc(C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-406ad0a2f8ae430e88d9a701a55ba15d | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1>>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | CC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.[OH-].[Na+]>>CC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)O | C[O:23][C:21]([c:20]1[c:15]([S:12]([NH:11][C:9]([NH:8][c:7]2[n:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[n:24]2)=[O:10])(=[O:13])=[O:14])[cH:16][cH:17][cH:18][cH:19]1)=[O:22]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[n:6][c:7]([NH:8][C:9](=[O:10])[NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21](=[O:2... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1 | Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A mixture of 2.0 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and 11 ml. of 50% aqueous sodium hydroxide was warmed on a steam bath with shaking; 40 ml. of water was added and heating and shaking continued during the next half hour. The resulting solution was then filtered and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | O | null | null | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(C)n1>O>Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6733e48ccf3a4c649590e34bbc1869b6 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1>>COc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.[OH-].[K+].Cl>>COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)O | C[O:24][C:22]([c:21]1[c:16]([S:13]([NH:12][C:10]([NH:9][c:8]2[n:7][c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[n:25]2)=[O:11])(=[O:14])=[O:15])[cH:17][cH:18][cH:19][cH:20]1)=[O:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | COc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 | null | null | O.C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 24 | HOUR | 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide was dissolved in a mixture of 20 ml of absolute ethanol, 2.5 ml of water and 2.5 g of potassium hydroxide. After stirring at 25° for 24 hours the mixture had become a semi-solid mass. Enough cold water was added to dissolve... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | O.C(C)O | null | 24 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1>O.C(C)O>COc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-df889e238e9c4d9a9277611c2937cc0a | CCOC(=O)C(C)Oc1nc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O>>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC(C)C(=O)O)n1 | S(=O)(=O)(N=C=O)N=C=O.Cl.N(=C=O)S(=O)(=O)C1=C(C(=O)OC)C=CC=C1.NC1=NC(=NC(=N1)C)OC(C(=O)OCC)C.[OH-].[Na+].S(=O)(=O)(N=C=O)N=C=O>>C(=O)(O)C(C)OC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1 | CC[O:29][C:27]([CH:25]([O:24][c:23]1[n:22][c:20]([CH3:21])[n:19][c:18]([NH2:17])[n:30]1)[CH3:26])=[O:28].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[N:14]=[C:15]=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[NH:14][C:15](=[O:16]... | CCOC(=O)C(C)Oc1nc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC(C)C(=O)O)n1 | null | null | O.C(Cl)Cl | Acylation | OtherReaction | 873ec03fe95613b89e1cc5a05f22b73e12ebaee68f679a7c1a383abbdb2c243b | 5dcf854e8ae1ebe2ca3cab743b2d9636aaa3c8192f5216ab3e9c6da3c3a8eaed | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:1.[O;D1;H0:12]=[#16:13](=[O;D1;H0:14])(-[c:15])-[N;H0;D2;+0:16]=[C;H0;D2;+0:17]=[O;D1;H0:18]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:12]=[#16:13](=[O;D1;H0:14])(-[c:15])-[NH;D2;+0:16]-[C;H0;D3;+0:17](=[O;... | 23.8 | [{"value": 23.8, "product": "C(=O)(O)C(C)OC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C(=O)OC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 2-(isocyanatosulfonyl)benzoate (10.1 g) and 8.0 g of ethyl 2-[(4-amino-6-methyl-1,3,5-triazin-2-yl)oxy]propanoate were stirred in 80 ml of methylene chloride at ambient temperature for 18 hours. An additional 2 g of the sulfonylisocyanate was added and the reaction mixture was stirred for four more hours and the... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Sulfonamide.Carboxylic acid.Urea | null | null | c1ccccc1.c1ncncn1 | Other | O.C(Cl)Cl | null | null | CCOC(=O)C(C)Oc1nc(C)nc(N)n1.COC(=O)c1ccccc1S(=O)(=O)N=C=O>O.C(Cl)Cl>COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC(C)C(=O)O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9b7bed28437b45aa91a2069ef0051de5 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)NN1N=C(OC)C=C(C)N1.CS>>COC1=NN(NC(=O)NS(=O)(=O)c2ccccc2C(=O)SC)NC(C)=C1 | C[Al](C)C.COC1=NN(NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.CS>>COC1=NN(NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)SC | CO[C:19]([c:18]1[c:13]([S:10]([NH:9][C:7]([NH:6][N:5]2[N:4]=[C:3]([O:2][CH3:1])[CH:26]=[C:24]([CH3:25])[NH:23]2)=[O:8])(=[O:11])=[O:12])[cH:14][cH:15][cH:16][cH:17]1)=[O:20].[SH:21][CH3:22]>>[CH3:1][O:2][C:3]1=[N:4][N:5]([NH:6][C:7](=[O:8])[NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19](=... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)NN1N=C(OC)C=C(C)N1.CS | COC1=NN(NC(=O)NS(=O)(=O)c2ccccc2C(=O)SC)NC(C)=C1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | c823aed818d01e122d4213eef16971b16859047f24c9408150d480c9cbf7c870 | 46b20de9e98593a3c8a090991815ec74dc6f5a01657f01a6f6db1ed958280181 | O=C(NN1N=CC=CN1)NS(=O)(=O)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[SH;D1;+0:7]>>[C;D1;H3:6]-[S;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | Trimethylaluminum (6.0 ml, 2M) was charged via syringe to 15 ml dry toluene under nitrogen atmosphere and 3.8 g N-[(4-methoxy-6-methyltriazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide was added portionwise. After stirring at room temperature for one hour, methyl mercaptan (gas) was passed through the reac... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aliphatic thiol | Carbo-thioester | null | null | C1=CN[NH]N=C1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 1 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)NN1N=C(OC)C=C(C)N1.CS>C1(=CC=CC=C1)C>COC1=NN(NC(=O)NS(=O)(=O)c2ccccc2C(=O)SC)NC(C)=C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d747406f0a4e45e7871e9db7c0135f95 | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1.[CH3][Al]([CH3])[CH3]>>CCCCSC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | C[Al](C)C.COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC>>COC1=NC(=NC(=C1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)SCCCC | O([CH3:4])[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:5](=[O:15])(=[O:16])[NH:17][C:18](=[O:19])[NH:20][c:21]1[n:22][c:23]([CH3:24])[cH:25][c:26]([O:27][CH3:28])[n:29]1.[Al]([CH3:1])([CH3:2])[CH3:3]>>[CH3:1][CH2:2][CH2:3][CH2:4][S:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[S:14](=[O:15])(=[O:16... | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1.[CH3][Al]([CH3])[CH3] | CCCCSC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 278ae0d28540c9554333d1751c4d8864b8f05ad2e43bfc48a420bf0664bdbb56 | f9b8b2b39f1824e0bcab4a130c63b5122605294cff8ca1aa0ec1553a229324e0 | O=C(Nc1ncccn1)NS(=O)(=O)c1ccccc1 | [#7;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[S;H0;D4;+0:7](=[O;H0;D1;+0:8])(=[O;H0;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-[CH3;D1;+0:16]):[c:17]):[#7;a:18].[CH3;D1;+0:19]-[Al](-[CH3;D1;+0:20])-[CH3;D1;+0:21]>>[#7;a:1]:[c:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]... | null | [] | 80 | CELSIUS | null | null | Trimethylaluminum (1.5 ml) (2M) was charged via syringe to 5.0 ml dry toluene under nitrogen atmosphere and 0.54 g (0.006 mole) N-butanethiol in 2.0 ml toluene was added dropwise. N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide (0.95 g) was added portionwise and the mixture warme... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ester.Urea | Sulfonamide.Urea.Carbo-thioester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1 | HO- | C1(=CC=CC=C1)C | 80 | null | COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1.[CH3][Al]([CH3])[CH3]>C1(=CC=CC=C1)C>CCCCSC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)cc(OC)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9192a0a5af414f0dace034f8e1bc1889 | CC(C)S.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=S)C(C)C)n1 | COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC.C[Al](C)C.CC(C)S.C1(=CC=CC=C1)C.C1(=CC=CC=C1)C.Cl.[Al]>>COC1=NC(=NC(=N1)C)NC(=O)NS(=O)(=O)C1=C(C=CC=C1)C(=S)C(C)C | [SH:23][CH:24]([CH3:25])[CH3:26].CO[C:22](=O)[c:21]1[c:16]([S:13]([NH:12][C:10]([NH:9][c:8]2[n:7][c:5]([CH3:6])[n:4][c:3]([O:2][CH3:1])[n:27]2)=[O:11])(=[O:14])=[O:15])[cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18]... | CC(C)S.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 | COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=S)C(C)C)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 36827b64c13cf65c6e52cebaa9062cdf58fab985f2c9cdbf979bb47a3868d38c | f21a09760a88a80841695969620085328ea5d75a4ab5df4999a2de5bb620d932 | O=C(Nc1ncncn1)NS(=O)(=O)c1ccccc1 | C-O-[C;H0;D3;+0:1](=O)-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[SH;D1;+0:8]>>[C;D1;H3:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[C;H0;D3;+0:1](=[S;H0;D1;+0:8])-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | null | null | To 1.5 ml (2N) trimethylaluminum in 5 ml dry toluene under N2 was added dropwise 0.48 g (6.0 mmole) 2-propanethiol in 2 ml toluene. The resultant aluminum reagent was stirred at room temperature for 15 minutes, and 0.95 g (2.5 mmole) N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aliphatic thiol | Thiocarbonyl | null | null | c1ncncn1.c1ccccc1 | HO- | null | 80 | null | CC(C)S.COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=S)C(C)C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7c9c3f5ab6b3464a9a375be91bb42a21 | NCc1ccc(C(=O)O)cc1.O=C(Cl)CCCc1ccccc1>>O=C(CCCc1ccccc1)NCc1ccc(C(=O)O)cc1 | Cl.NCC1=CC=C(C(=O)O)C=C1.Cl[Si](C)(C)C.C1(=CC=CC=C1)CCCC(=O)Cl>>C(=O)(O)C1=CC=C(CNC(CCCC2=CC=CC=C2)=O)C=C1 | [NH2:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]1.Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]1 | NCc1ccc(C(=O)O)cc1.O=C(Cl)CCCc1ccccc1 | O=C(CCCc1ccccc1)NCc1ccc(C(=O)O)cc1 | null | null | C(C)N(CC)CC.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CCCc1ccccc1)NCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | 1 | HOUR | 4-(Aminomethyl)benzoic acid (3.6 g) is suspended in methylene chloride (100 mL), to which 15 mL triethylamine is added. Chlorotrimethylsilane (10 mL) is then added and the mixture allowed to stir at room temperature for 1 hr. The mixture is then cooled in an ice bath and 4-phenylbutyryl chloride (5.3 g) in methylene ch... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(C)N(CC)CC.C(Cl)Cl | null | 1 | NCc1ccc(C(=O)O)cc1.O=C(Cl)CCCc1ccccc1>C(C)N(CC)CC.C(Cl)Cl>O=C(CCCc1ccccc1)NCc1ccc(C(=O)O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2983717c5ff843609eb3651968b56a3e | CCCCCC(=O)O.NCc1ccc(C(=O)O)cc1>>CCCCCC(=O)NCc1ccc(C(=O)O)cc1 | C(CCCCC)(=O)O.CN1CCOCC1.NCC1=CC=C(C=C1)C(=O)O.Cl[Si](C)(C)C.ClC(=O)OCC>>C(=O)(O)C1=CC=C(CNC(CCCCC)=O)C=C1 | O[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]1 | CCCCCC(=O)O.NCc1ccc(C(=O)O)cc1 | CCCCCC(=O)NCc1ccc(C(=O)O)cc1 | null | null | C(C)#N.C(C)N(CC)CC.C(=O)(O)C1=CC=C(CNC(CCCC2=CC=CC=C2)=O)C=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | -20 | CELSIUS | 8 | HOUR | Hexanoic acid (3.06 g) in 20 mL acetonitrile is treated with N-methylmorpholine (2.9 mL) and the mixture cooled to -20° C. with stirring. Ethyl chloroformate (2.8 mL) is then added dropwise, keeping the temperature below or at -20° C. After stirring for an additional 40 min at that temperature, the solution is transfer... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(C)#N.C(C)N(CC)CC.C(=O)(O)C1=CC=C(CNC(CCCC2=CC=CC=C2)=O)C=C1 | -20 | 8 | CCCCCC(=O)O.NCc1ccc(C(=O)O)cc1>C(C)#N.C(C)N(CC)CC.C(=O)(O)C1=CC=C(CNC(CCCC2=CC=CC=C2)=O)C=C1>CCCCCC(=O)NCc1ccc(C(=O)O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c7f22c22bf7248b09d9b1658ab15c25e | CC(=O)c1ccc(C(=O)O)cc1.N>>CC(N)c1ccc(C(=O)O)cc1 | C(C)(=O)C1=CC=C(C(=O)O)C=C1.N>>NC(C)C1=CC=C(C(=O)O)C=C1 | O=[C:2]([CH3:1])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1.[NH3:3]>>[CH3:1][CH:2]([NH2:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][cH:12]1 | CC(=O)c1ccc(C(=O)O)cc1.N | CC(N)c1ccc(C(=O)O)cc1 | null | [Ni] | null | Heteroatom Alkylation and Arylation | OtherReaction | 093a425c24820cdc0dc5498ac97584b843c895d02cd3985cef27fb65990a19ae | 57403092f2152b38361ff8e391b9a821f5623bf2a2bbf7514162beafc6524986 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[NH3;D0;+0:6]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH2;D1;+0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 4-Acetylbenzoic acid (4.1 g) is dissolved in 50 mL ammonia-saturated methanol. Raney nickel catalyst (1.5 g; activity grade III) is then added and the mixture reduced under hydrogen atmosphere (4750 psi) at 80° C. for 17 hrs. After removal of the catalyst by suction filtration, the filtrate is evaporated and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | c1ccccc1 | Other | [Ni] | null | null | CC(=O)c1ccc(C(=O)O)cc1.N>[Ni]>CC(N)c1ccc(C(=O)O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fce11ed57542484f99d16dc452968749 | CCCCCCCCC(=O)Cl.N#Cc1ccc(CN)cc1>>CCCCCCCCC(=O)NCc1ccc(C#N)cc1 | C(CCCCCCCC)(=O)Cl.NCC1=CC=C(C#N)C=C1.C(C)N(CC)CC>>C(#N)C1=CC=C(CNC(CCCCCCCC)=O)C=C1 | Cl[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:10].[NH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[NH:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1 | CCCCCCCCC(=O)Cl.N#Cc1ccc(CN)cc1 | CCCCCCCCC(=O)NCc1ccc(C#N)cc1 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 98.5 | [{"value": 98.5, "product": "C(#N)C1=CC=C(CNC(CCCCCCCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 4-(aminomethyl)benzonitrile (5.0 g, 0.038 moles) in 100 mL chloroform is added 3.82 g (0.038 moles) triethylamine. A solution of nonanoyl chloride (6.68 g, 0.038 moles) in 10 mL chloroform is then added dropwise with stirring over a 10 min period and the final mixture stirred at room temperature for 18... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 0.166667 | CCCCCCCCC(=O)Cl.N#Cc1ccc(CN)cc1>C(Cl)(Cl)Cl>CCCCCCCCC(=O)NCc1ccc(C#N)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1f7059ca42634837b7b995e414e4f63a | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)OCC)cc2)cc1.CCOC(=O)c1ccc(-c2ccc(O)cc2)cc1>>CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)O)cc2)cc1 | CC(CCCCCC)OS(=O)(=O)C=1C(=CC=CC1)C.C(C)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(CCCCCC)C.[OH-].[Na+].[OH-].[K+].C(C)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)O>>CC(CCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O | CCOC(=O)c1ccc(-c2ccc(O[CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH3:8])cc2)cc1.CC[O:20][C:18]([c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][cH:11][c:10]([OH:9])[cH:24][cH:23]2)[cH:22][cH:21]1)=[O:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16]... | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)OCC)cc2)cc1.CCOC(=O)c1ccc(-c2ccc(O)cc2)cc1 | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)O)cc2)cc1 | null | null | O.C1(=CC=CC=C1)C.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 6bf234bed3816464d95cc34f217e2e2df8c9a6ea3e1240efcc21e1db8d0769aa | fdde2439a4b82e26b70a14eed2ee49e33eff2a45a5183f418d9b5244a048673c | c1ccc(-c2ccccc2)cc1 | C-C-O-C(=O)-c1:c:c:c(-c2:c:c:c(-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]):c:c:2):c:c:1.C-C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 65.8 | [{"value": 65.8, "product": "CC(CCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | On the other hand, 4-hydroxy-4'-biphenylcarboxylic acid ethyl ester (IV) (38.7 g, 0.160 mol) was dissolved in ethanol (200 ml), and KOH (9 g, 0.160 mol) was added to and dissolved in the solution, followed by adding optically active toluenesulfonic acid 1-methyl-heptyl ester (50 g, 0.176 mol) obtained above, keeping th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Aromatic alcohol | Carboxylic acid.Ether | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | O.C1(=CC=CC=C1)C.C(C)O | null | null | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)OCC)cc2)cc1.CCOC(=O)c1ccc(-c2ccc(O)cc2)cc1>O.C1(=CC=CC=C1)C.C(C)O>CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)O)cc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-05c7a79b32a14c249690b3af58161101 | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)OCC)cc2)cc1.CCOC(=O)c1ccc(-c2ccc(O)cc2)cc1>>CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)O)cc2)cc1 | [OH-].[Na+].FC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(CCCCCC)C.BrC1=CC=C(C=C1)C1=CC=C(C=C1)OC(C1=CC=C(C=C1)OC(CCCCCC)C)=O.[OH-].[K+].C(C)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(CCCCCC)C.Cl.C(C)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)O>>CC(CCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O | CCOC(=O)c1ccc(-c2ccc(O[CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH3:8])cc2)cc1.CC[O:20][C:18]([c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][cH:11][c:10]([OH:9])[cH:24][cH:23]2)[cH:22][cH:21]1)=[O:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16]... | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)OCC)cc2)cc1.CCOC(=O)c1ccc(-c2ccc(O)cc2)cc1 | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)O)cc2)cc1 | null | null | O.C1(=CC=CC=C1)C.CO.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 6bf234bed3816464d95cc34f217e2e2df8c9a6ea3e1240efcc21e1db8d0769aa | fdde2439a4b82e26b70a14eed2ee49e33eff2a45a5183f418d9b5244a048673c | c1ccc(-c2ccccc2)cc1 | C-C-O-C(=O)-c1:c:c:c(-c2:c:c:c(-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]):c:c:2):c:c:1.C-C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 12 | [{"value": 12.0, "product": "CC(CCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Preparation of optically active p-(1-methylheptyloxy)benzoic acid 4'-bromo-4-biphenylyl ester (a compound of the formula (I) wherein l=1, m=1, R=C6H13, X=Br and Y, Z=H; Sample No. 9) P-hydroxybenzoic acid methyl ester (IV) (28.5 g, 0.187 mol) was dissolved in methanol (120 ml), and KOH (10.1 g, 0.187 mol) was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Aromatic alcohol | Carboxylic acid.Ether | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | O.C1(=CC=CC=C1)C.CO.C(C)O | null | null | CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)OCC)cc2)cc1.CCOC(=O)c1ccc(-c2ccc(O)cc2)cc1>O.C1(=CC=CC=C1)C.CO.C(C)O>CCCCCCC(C)Oc1ccc(-c2ccc(C(=O)O)cc2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-04a69b390603494d8ec23214d1692e8d | O=[N+]([O-])[O-]>>O=[N+]([O-])[O-] | O.O.O.O.[N+](=O)([O-])[O-].[Ca+2].[N+](=O)([O-])[O-]>>[N+](=O)([O-])[O-].[Ca+2].[N+](=O)([O-])[O-] | [O:1]=[N+:2]([O-:3])[O-:4]>>[O:1]=[N+:2]([O-:3])[O-:4] | O=[N+]([O-])[O-] | O=[N+]([O-])[O-] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 1.470 grams of calcium nitrate tetrahydrate are dissolved in deionised water and the solution is made up to 1 liter;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | O=[N+]([O-])[O-]>O>O=[N+]([O-])[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-097272a242654e05afb16ca1f82bb65b | Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1c(N)cc(Oc3ccccc3)c(O)c1C2=O>>CCCCOc1cc(N)c2c(c1O)C(=O)c1c(O)c(OCCCC)cc(N)c1C2=O | C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.NC1=CC(=C(C=2C(C3=C(C(=CC(=C3C(C12)=O)N)OC1=CC=CC=C1)O)=O)O)OC1=CC=CC=C1>>NC1=CC(=C(C=2C(C3=C(C(=CC(=C3C(C12)=O)N)OCCCC)O)=O)O)OCCCC | c1c[c:4]([O:5][c:6]2[cH:7][c:8]([NH2:9])[c:10]3[c:11]([c:12]2[OH:13])[C:14](=[O:15])[c:16]2[c:17]([OH:18])[c:19]([O:20][c:21]4cc[cH:24][cH:23][cH:22]4)[cH:25][c:26]([NH2:27])[c:28]2[C:29]3=[O:30])[cH:3][cH:2][cH:1]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[c:10]2[c:11]([c:12]1[OH:13])[C:14](=[O:15])... | Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1c(N)cc(Oc3ccccc3)c(O)c1C2=O | CCCCOc1cc(N)c2c(c1O)C(=O)c1c(O)c(OCCCC)cc(N)c1C2=O | null | null | null | Miscellaneous | OtherReaction | 71d8dbd5ceb3f01579ada7a6b2f508b86da626f9dd0c7f994a227c3a44d3ca3b | 86987b8d209edb1ce435f440f2173683a0ee5e65bacddfa7c9c1b7e6b42d5e7e | O=C1c2ccccc2C(=O)c2ccccc21 | [c:1]-[#8:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:c:c:1.[c:7]-[#8:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:c:c:1>>[CH3;D1;+0:12]-[CH2;D2;+0:11]-[CH2;D2;+0:10]-[CH2;D2;+0:9]-[#8:8]-[c:7].[CH3;D1;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[#8:2]-[c:1] | null | [] | null | null | null | null | When the process described in Example 165a is carried out and, instead of the anthraquinone derivative mentioned there, 5.7 g of 1,8-diamino-4,5-dihydroxy-3,6-diphenoxyanthraquinone (preparation see Example 351a) are used, then 4.2 g, corresponding to 80% of theory, of 1,8-diamino-4,5-dihydroxy-3,6-di-n-butoxyanthraqui... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ether.Ether | c1ccccc1.c1ccccc1 | null | c1ccc2c(c1)Cc1ccccc1C2 | Other | null | null | null | Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1c(N)cc(Oc3ccccc3)c(O)c1C2=O>>CCCCOc1cc(N)c2c(c1O)C(=O)c1c(O)c(OCCCC)cc(N)c1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5d2d9add6bc14a31b538c5d40432cf60 | Nc1c(Br)cc(O)c2c1C(=O)c1c(O)cc(Br)c(N)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21>>Nc1c(Br)cc(O)c2c1C(=O)c1c(O)cc(Oc3ccccc3)c(N)c1C2=O | C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.NC1=C(C=C(C=2C(C3=C(C(=CC(=C3C(C12)=O)O)Br)N)=O)O)Br>>NC1=C(C=C(C=2C(C3=C(C(=CC(=C3C(C12)=O)O)Br)N)=O)O)OC1=CC=CC=C1 | Br[c:16]1[cH:15][c:13]([OH:14])[c:12]2[c:26]([c:24]1[NH2:25])[C:27](=[O:28])[c:8]1[c:6]([OH:7])[cH:5][c:3]([Br:4])[c:2]([NH2:1])[c:9]1[C:10]2=[O:11].O=C1c2ccccc2C(=[O:17])[c:22]2[cH:21][cH:20][cH:19][cH:18][c:23]21>>[NH2:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([OH:7])[c:8]2[c:9]1[C:10](=[O:11])[c:12]1[c:13]([OH:14])[cH:15][c:... | Nc1c(Br)cc(O)c2c1C(=O)c1c(O)cc(Br)c(N)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21 | Nc1c(Br)cc(O)c2c1C(=O)c1c(O)cc(Oc3ccccc3)c(N)c1C2=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df99467353cd9a58057c83a561ffd810cfbb9d7f534fb7ba414a2597728cdbac | b765e65d02c0118596ca0b0929fad1cff9a0fe4e7b851975a8542a4eed0f5923 | O=C1c2ccccc2C(=O)c2cc(Oc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6]-[C:7]=[O;D1;H0:8].O=C1-[c;H0;D3;+0:9]2:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:[c;H0;D3;+0:14]:2-C(=[O;H0;D1;+0:15])-c2:c:c:c:c:c:2-1>>[N;D1;H2:5]-[c:4](:[c:6]-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:1](-[O;H0;D2;+0:15]-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:[cH;... | null | [] | null | null | null | null | When the process according to Example 190a is carried out and, instead of the anthraquinone component mentioned there, 11.7 g of 1,5-diamino-4,8-dihydroxy-2,6-dibromoanthraquinone, compare Example 348a, are used, then 3.8 g, corresponding to 31% of theory, of 1,5-diamino-4,8-dihydroxy-2-phenoxy-6-bromoanthraquinone are... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ketone | Ether | c1ccc2c(c1)Cc1ccccc1C2.c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | HBr | null | null | null | Nc1c(Br)cc(O)c2c1C(=O)c1c(O)cc(Br)c(N)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21>>Nc1c(Br)cc(O)c2c1C(=O)c1c(O)cc(Oc3ccccc3)c(N)c1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-30c616f407b74e7c8cef1dc122b53a6e | Nc1cc(Br)c(O)c2c1C(=O)c1c(O)c(Br)cc(N)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21>>Nc1cc(Br)c(O)c2c1C(=O)c1c(O)c(Oc3ccccc3)cc(N)c1C2=O | NC1=CC(=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)O)Br)N)=O)O)Br.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O>>NC1=CC(=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)O)Br)N)=O)O)OC1=CC=CC=C1 | Br[c:15]1[c:13]([OH:14])[c:12]2[c:26]([c:24]([NH2:25])[cH:23]1)[C:27](=[O:28])[c:8]1[c:6]([OH:7])[c:4]([Br:5])[cH:3][c:2]([NH2:1])[c:9]1[C:10]2=[O:11].O=C1c2ccccc2[C:17](=[O:16])[c:22]2c1[cH:18][cH:19][cH:20][cH:21]2>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[c:6]([OH:7])[c:8]2[c:9]1[C:10](=[O:11])[c:12]1[c:13]([OH:14])[c:15]([... | Nc1cc(Br)c(O)c2c1C(=O)c1c(O)c(Br)cc(N)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21 | Nc1cc(Br)c(O)c2c1C(=O)c1c(O)c(Oc3ccccc3)cc(N)c1C2=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df99467353cd9a58057c83a561ffd810cfbb9d7f534fb7ba414a2597728cdbac | b765e65d02c0118596ca0b0929fad1cff9a0fe4e7b851975a8542a4eed0f5923 | O=C1c2ccccc2C(=O)c2cc(Oc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6]-[C:7]=[O;D1;H0:8].O=C1-c2:[cH;D2;+0:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:2-[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-c2:c:c:c:c:c:2-1>>[O;D1;H0:8]=[C:7]-[c:6]:[c:4](-[O;D1;H1:5]):[c;H0;D3;+0:1](-[O;H0;D2;+0:15]-[c;H0;D3;+0:14]1:[cH;D2;+0:9]:[c:10]:[c:11]:[c:12]:[cH;D... | null | [] | null | null | null | null | When 11.7 g of 1,5-diamino-4,8-dihydroxy-3,7-dibromoanthraquinone, compared Example 349a, are used as the anthraquinone component in Example 415a, then 3.9 g, corresponding to 32% of theory, of 1,5-diamino-4,8-dihydroxy-3-phenoxy-7-bromoanthraquinone are obtained quite analogously, the colour shade of which, adsorbed o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ketone | Ether | c1ccc2c(c1)Cc1ccccc1C2.c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | HBr | null | null | null | Nc1cc(Br)c(O)c2c1C(=O)c1c(O)c(Br)cc(N)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21>>Nc1cc(Br)c(O)c2c1C(=O)c1c(O)c(Oc3ccccc3)cc(N)c1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7787c3ce113841c98cb4a33921498271 | Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Br)cc(O)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21>>Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Oc3ccccc3)cc(O)c1C2=O | NC1=C(C=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)N)Br)O)=O)O)Br.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O>>NC1=C(C=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)N)Br)O)=O)O)OC1=CC=CC=C1 | Br[c:15]1[c:13]([NH2:14])[c:12]2[c:26]([c:24]([OH:25])[cH:23]1)[C:27](=[O:28])[c:8]1[c:6]([OH:7])[cH:5][c:3]([Br:4])[c:2]([NH2:1])[c:9]1[C:10]2=[O:11].O=C1c2cc[cH:20][cH:19][c:18]2[C:17](=[O:16])[c:22]2c1ccc[cH:21]2>>[NH2:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([OH:7])[c:8]2[c:9]1[C:10](=[O:11])[c:12]1[c:13]([NH2:14])[c:15]([... | Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Br)cc(O)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21 | Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Oc3ccccc3)cc(O)c1C2=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df99467353cd9a58057c83a561ffd810cfbb9d7f534fb7ba414a2597728cdbac | b765e65d02c0118596ca0b0929fad1cff9a0fe4e7b851975a8542a4eed0f5923 | O=C1c2ccccc2C(=O)c2cc(Oc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N;D1;H2:5]):[c:6]-[C:7]=[O;D1;H0:8].O=C1-c2:c:c:[cH;D2;+0:9]:[c:10]:[c;H0;D3;+0:11]:2-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[c;H0;D3;+0:14]2:[cH;D2;+0:15]:c:c:c:c:2-1>>[N;D1;H2:5]-[c:4](:[c:6]-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:1](-[O;H0;D2;+0:13]-[c;H0;D3;+0:12]1:[cH;D2;+0:11]:[c:10]:[c... | null | [] | null | null | null | null | When 11.7 g of 1,8-diamino-4,5-dihydroxy-2,7-dibromoanthraquinone (compare Example 350a) are used as the anthraquinone component in Example 415a, then 4.5 g, corresponding to 37% of theory, of 1,8-diamino-4,5-dihydroxy-2-phenoxy-7-bromoanthraquinone are correspondingly obtained. Colour shade on silica gel: blue of Indi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ketone | Ether | c1ccc2c(c1)Cc1ccccc1C2.c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | HBr | null | null | null | Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Br)cc(O)c1C2=O.O=C1c2ccccc2C(=O)c2ccccc21>>Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Oc3ccccc3)cc(O)c1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5ab9733b73e248a5897dce1cc7235956 | Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Oc3ccccc3)cc(O)c1C2=O>>CCCCOc1cc(O)c2c(c1N)C(=O)c1c(N)c(Br)cc(O)c1C2=O | NC1=C(C=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)N)Br)O)=O)O)OC1=CC=CC=C1.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O>>NC1=C(C=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)N)Br)O)=O)O)OCCCC | c1c[c:4]([O:5][c:6]2[cH:7][c:8]([OH:9])[c:10]3[c:11]([c:12]2[NH2:13])[C:14](=[O:15])[c:16]2[c:17]([NH2:18])[c:19]([Br:20])[cH:21][c:22]([OH:23])[c:24]2[C:25]3=[O:26])[cH:3][cH:2][cH:1]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([OH:9])[c:10]2[c:11]([c:12]1[NH2:13])[C:14](=[O:15])[c:16]1[c:17]([NH2:18])[c:19](... | Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Oc3ccccc3)cc(O)c1C2=O | CCCCOc1cc(O)c2c(c1N)C(=O)c1c(N)c(Br)cc(O)c1C2=O | null | null | null | Miscellaneous | OtherReaction | 8b8bcce0813fb7fd128f1b1f2b7d91323370ec043815f214fbbc57359676ea39 | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | O=C1c2ccccc2C(=O)c2ccccc21 | [c:1]-[#8:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:c:c:1>>[CH3;D1;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[#8:2]-[c:1] | null | [] | null | null | null | null | When 5.5 of 1,8-diamino-4,5-dihydroxy-2-phenoxy-7-bromoanthraquinone (preparation see Example 417a) are used in Example 338a instead of the anthraquinone component mentioned there, then 4.5 g, corresponding to 85% of theory, of 1,8-diamino-4,5-dihydroxy-2-n-butoxy-7-bromoanthraquinone are obtained quite correspondingly... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | c1ccccc1 | null | c1ccc2c(c1)Cc1ccccc1C2 | Other | null | null | null | Nc1c(Br)cc(O)c2c1C(=O)c1c(N)c(Oc3ccccc3)cc(O)c1C2=O>>CCCCOc1cc(O)c2c(c1N)C(=O)c1c(N)c(Br)cc(O)c1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ae0d07ead4c04e6a8c070aef170e9faf | Nc1c(Br)cc(Br)c2c1C(=O)c1ccc(Cl)cc1C2=O.Nc1c(Br)cc(Br)c2c1C(=O)c1ccccc1C2=O>>Nc1c(Br)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O | NC1=C(C=C(C=2C(C3=CC(=CC=C3C(C12)=O)Cl)=O)Br)Br.B(O)(O)O.S(O)(O)(=O)=O.NC1=C(C=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)Br)Br>>NC1=C(C=C(C=2C(C3=CC(=CC=C3C(C12)=O)Cl)=O)O)Br | Br[c:6]1[cH:5][c:3]([Br:4])[c:2]([NH2:1])[c:9]2[c:8]1[C:19](=[O:20])[c:18]1[c:12]([cH:13][cH:14][c:15]([Cl:16])[cH:17]1)[C:10]2=[O:11].Nc1c(Br)cc(Br)c2c1C(=O)c1ccccc1C2=[O:7]>>[NH2:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([OH:7])[c:8]2[c:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]1[C:19]2=[O:20] | Nc1c(Br)cc(Br)c2c1C(=O)c1ccc(Cl)cc1C2=O.Nc1c(Br)cc(Br)c2c1C(=O)c1ccccc1C2=O | Nc1c(Br)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dc217a1eb23b8421f4796b85ea24143adbaf5f0a694f96742eec4fcf53237aa2 | 96a208e5cde71d3d2a584dd67ac8ebfad83ae2dcb4df5564875507c8a019d05e | O=C1c2ccccc2C(=O)c2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]-[C:6]=[O;D1;H0:7])-[C:8](=[O;D1;H0:9])-[c:10].Br-c1:c:c(-Br):c2:c(:c:1-N)-C(=O)-c1:c:c:c:c:c:1-C-2=[O;H0;D1;+0:11]>>[O;D1;H0:7]=[C:6]-[c:5]:[c:4](:[c;H0;D3;+0:1](-[OH;D1;+0:11]):[c:2]:[c:3])-[C:8](=[O;D1;H0:9])-[c:10] | null | [] | null | null | null | null | When 104 g of 1-amino-2,4-dibromo-6-chloroanthraquinone (preparation see Example 467a) are treated with boric acid/sulphuric acid according to the procedure for 1-amino-2,4-dibromoanthraquinone in BIOS 1484, page 5, then 83.9 g, corresponding to 95% of theory, of 1-amino-2-bromo-4-hydroxy-6-chloroanthraquinone are obta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ketone.Ketone.Primary amine | Aromatic alcohol | c1ccc2c(c1)Cc1ccccc1C2.c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | HBr | null | null | null | Nc1c(Br)cc(Br)c2c1C(=O)c1ccc(Cl)cc1C2=O.Nc1c(Br)cc(Br)c2c1C(=O)c1ccccc1C2=O>>Nc1c(Br)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3b0a368a26d1420fa70558b211b82b38 | Nc1cc(Br)c(O)c2c1C(=O)c1cc(Cl)ccc1C2=O.[O-]c1ccccc1>>Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1cc(Cl)ccc1C2=O | OC1=C(C=C(C=2C(C3=CC(=CC=C3C(C12)=O)Cl)=O)N)Br.C1(=CC=CC=C1)[O-]>>OC1=C(C=C(C=2C(C3=CC(=CC=C3C(C12)=O)Cl)=O)N)OC1=CC=CC=C1 | Br[c:4]1[cH:3][c:2]([NH2:1])[c:15]2[c:14]([c:12]1[OH:13])[C:25](=[O:26])[c:24]1[c:18]([cH:19][c:20]([Cl:21])[cH:22][cH:23]1)[C:16]2=[O:17].[O-:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([OH:13])[c:14]2[c:15]1[C:16](=[O:17])[c:18]1[cH:19][c:20]... | Nc1cc(Br)c(O)c2c1C(=O)c1cc(Cl)ccc1C2=O.[O-]c1ccccc1 | Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1cc(Cl)ccc1C2=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a641d08ab0f76020b7550a72b1d496f3b945fcd3fbebda633a6546f25db4f81e | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=C1c2ccccc2C(=O)c2cc(Oc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6]-[C:7]=[O;D1;H0:8].[O-;H0;D1:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:8]=[C:7]-[c:6]:[c:4](-[O;D1;H1:5]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | null | [] | null | null | null | null | When 70.5 g of the 1-hydroxy-2-bromo-4-amino-6-chloroanthraquinone prepared above are subjected to a phenolate fusion as described in Example 467c, then 59 g, corresponding to 80% of theory, of 1-hydroxy-2-phenoxy-4-amino-6-chloroanthraquinone are obtained, the colour shade of which on silica gel is a pink tinged with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | Br- | null | null | null | Nc1cc(Br)c(O)c2c1C(=O)c1cc(Cl)ccc1C2=O.[O-]c1ccccc1>>Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1cc(Cl)ccc1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a983ac3eee2e42748e865bdbd507ab4d | Nc1cc(Br)c(O)c2c1C(=O)c1ccc(Cl)cc1C2=O.[O-]c1ccccc1>>Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1ccc(Cl)cc1C2=O | OC1=C(C=C(C=2C(C3=CC=C(C=C3C(C12)=O)Cl)=O)N)Br.C1(=CC=CC=C1)[O-]>>OC1=C(C=C(C=2C(C3=CC=C(C=C3C(C12)=O)Cl)=O)N)OC1=CC=CC=C1 | Br[c:4]1[cH:3][c:2]([NH2:1])[c:15]2[c:14]([c:12]1[OH:13])[C:25](=[O:26])[c:24]1[c:18]([cH:19][cH:20][c:21]([Cl:22])[cH:23]1)[C:16]2=[O:17].[O-:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([OH:13])[c:14]2[c:15]1[C:16](=[O:17])[c:18]1[cH:19][cH:20... | Nc1cc(Br)c(O)c2c1C(=O)c1ccc(Cl)cc1C2=O.[O-]c1ccccc1 | Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1ccc(Cl)cc1C2=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a641d08ab0f76020b7550a72b1d496f3b945fcd3fbebda633a6546f25db4f81e | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=C1c2ccccc2C(=O)c2cc(Oc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6]-[C:7]=[O;D1;H0:8].[O-;H0;D1:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:8]=[C:7]-[c:6]:[c:4](-[O;D1;H1:5]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | null | [] | null | null | null | null | When 70.5 g of the 1-hydroxy-2-bromo-4-amino-7-chloroanthraquinone prepared above are subjected to a phenolate fusion as described in Example 467c, then 61 g, corresponding to 83% of theory, of 1-hydroxy-2-phenoxy-4-amino-7-chloro-anthraquinone are obtained, the colour shade of which on silica gel is a pink tinged with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | Br- | null | null | null | Nc1cc(Br)c(O)c2c1C(=O)c1ccc(Cl)cc1C2=O.[O-]c1ccccc1>>Nc1cc(Oc2ccccc2)c(O)c2c1C(=O)c1ccc(Cl)cc1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0b831d043d2d403abc9af91ccf49b8fe | Nc1c(Oc2ccccc2)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O.OCCc1ccccc1>>Nc1c(OCCc2ccccc2)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O | C1(=CC=CC=C1)CCO.C1(CCCCCN1)=O.C([O-])([O-])=O.[K+].[K+].NC1=C(C=C(C=2C(C3=CC(=CC=C3C(C12)=O)Cl)=O)O)OC1=CC=CC=C1>>NC1=C(C=C(C=2C(C3=CC(=CC=C3C(C12)=O)Cl)=O)O)OCCC1=CC=CC=C1 | c1ccc(O[c:3]2[c:2]([NH2:1])[c:17]3[c:16]([c:14]([OH:15])[cH:13]2)[C:27](=[O:28])[c:26]2[c:20]([cH:21][cH:22][c:23]([Cl:24])[cH:25]2)[C:18]3=[O:19])cc1.[OH:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[NH2:1][c:2]1[c:3]([O:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]([OH:15])[c:16]... | Nc1c(Oc2ccccc2)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O.OCCc1ccccc1 | Nc1c(OCCc2ccccc2)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | d45daca12b62d5daedc63800836fbb244721eac6a88f01ca56f4e007cfff7656 | a72e725f7f9cab7f04874d9b7b6053baae17ea0414c85629e84910c31cd64b5f | O=C1c2ccccc2C(=O)c2cc(OCCc3ccccc3)ccc21 | [C:1]-[C:2]-[OH;D1;+0:3].[N;D1;H2:4]-[c:5](:[c:6]-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:9](-O-c1:c:c:c:c:c:1):[c:10]:[c:11]>>[C:1]-[C:2]-[O;H0;D2;+0:3]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:5](-[N;D1;H2:4]):[c:6]-[C:7]=[O;D1;H0:8] | null | [] | 140 | CELSIUS | null | null | A mixture of 48.8 g of β-phenylethanol, 45.2 g of ε-caprolactam, 5.2 g of dry potassium carbonate and 18.3 g of 1-amino-2-phenoxy-4-hydroxy-6-chloroanthraquinone (preparation see Example 467c) is heated at 140° C. until, after about 4 hours, the reaction is complete. The mixture at 70° C. is diluted with 100 ccm of met... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | HO- | CO | 140 | null | Nc1c(Oc2ccccc2)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O.OCCc1ccccc1>CO>Nc1c(OCCc2ccccc2)cc(O)c2c1C(=O)c1ccc(Cl)cc1C2=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-189ddf3bf8b14151ae66f2b2feefb8e0 | COc1ccccc1.O=C1c2c(O)ccc([N+](=O)[O-])c2C(=O)c2c([N+](=O)[O-])ccc(O)c21>>COc1ccc(-c2cc([N+](=O)[O-])c3c(c2O)C(=O)c2c(O)c(-c4ccc(OC)cc4)cc([N+](=O)[O-])c2C3=O)cc1 | OC1=CC=C(C=2C(C3=C(C=CC(=C3C(C12)=O)O)[N+](=O)[O-])=O)[N+](=O)[O-].C1(=CC=CC=C1)OC>>OC1=C(C=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)O)C1=CC=C(C=C1)OC)[N+](=O)[O-])=O)[N+](=O)[O-])C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:39][cH:40]1.[cH:7]1[cH:8][c:9]([OH:16])[c:13]2[c:14]([c:15]1[N+:10]([O-:11])=[O:21])[C:17](=[O:18])[c:19]1[c:20]([N+:33]([O-:12])=[O:34])[cH:22][cH:29][c:26]([OH:27])[c:36]1[C:37]2=[O:38]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]3[c:14... | COc1ccccc1.O=C1c2c(O)ccc([N+](=O)[O-])c2C(=O)c2c([N+](=O)[O-])ccc(O)c21 | COc1ccc(-c2cc([N+](=O)[O-])c3c(c2O)C(=O)c2c(O)c(-c4ccc(OC)cc4)cc([N+](=O)[O-])c2C3=O)cc1 | null | null | B(O)(O)O.S(O)(O)(=O)=O | Aromatic Heterocycle Formation | OtherReaction | 4e72a949318515fa5b558821473213981737ac4678c1ee334ec48d35da00ccce | afb79effa3b6044aa31a94a7c13fa7413ed61bceded3ab7770f05f814cfbcd7c | O=C1c2ccc(-c3ccccc3)cc2C(=O)c2cc(-c3ccccc3)ccc21 | [O-;H0;D1:1]-[N+;H0;D3:2](=[O;H0;D1;+0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c:6]:[c;H0;D3;+0:7](-[OH;D1;+0:8]):[c:9]2:[c:10]:1-[C:11](=[O;D1;H0:12])-[c:13]1:[c;H0;D3;+0:14](-[N+;H0;D3:15](-[O-;H0;D1:16])=[O;D1;H0:17]):[cH;D2;+0:18]:[cH;D2;+0:19]:[c;H0;D3;+0:20](-[OH;D1;+0:21]):[c;H0;D3;+0:22]:1-[C:23]-2=[O;D1;H0:24].[c:25... | 77.5 | [{"value": 77.0, "product": "OC1=C(C=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)O)C1=CC=C(C=C1)OC)[N+](=O)[O-])=O)[N+](=O)[O-])C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "OC1=C(C=C(C=2C(C3=C(C=C(C(=C3C(C12)=O)O)C1=CC=C(C=C1)OC)[N+](=O)[O-])=O)[N+](=O)[O-])C1=CC=C(C=C1)OC", "details... | 0 | CELSIUS | null | null | 9.9 g of 1,8-dihydroxy-4,5-dinitroanthraquinone are dissolved in a mixture of 15.6 g of boric acid and 228 g of 100 percent sulphuric acid. The solution obtained is cooled down to -10° to 0° C. and 7.4 g of anisole are added dropwise. The temperature is maintained for a further 1 hour at 0° C. and then the mixture is p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group.Nitro group.Aromatic alcohol.Aromatic alcohol | Ketone.Ether.Nitro group.Nitro group.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2.c1ccccc1 | null | B(O)(O)O.S(O)(O)(=O)=O | 0 | null | COc1ccccc1.O=C1c2c(O)ccc([N+](=O)[O-])c2C(=O)c2c([N+](=O)[O-])ccc(O)c21>B(O)(O)O.S(O)(O)(=O)=O>COc1ccc(-c2cc([N+](=O)[O-])c3c(c2O)C(=O)c2c(O)c(-c4ccc(OC)cc4)cc([N+](=O)[O-])c2C3=O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9bc2befe3f19445da6adb574b315731c | C=C(C)C(=O)OC.C=CC(=O)OCCCC.O=S(=O)([O-])OOS(=O)(=O)[O-].[NH4+]>>C=CC(=O)NC(O)C(=O)O | C(C(C)C)C1=C(C(=C(C=C1)O)CC(C)C)CC(C)C.C(CCC)OC(C=C)=O.[Na].C1CO1.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+].C(C(=C)C)(=O)OC.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+]>>C(C=C)(=O)NC(C(=O)O)O | C=[C:6](C)[C:8](=[O:9])[O:10]C.CCCCO[C:3]([CH:2]=[CH2:1])=[O:4].O=S(=O)([O-])O[O:7]S(=O)(=O)[O-].[NH4+:5]>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH:6]([OH:7])[C:8](=[O:9])[OH:10] | C=C(C)C(=O)OC.C=CC(=O)OCCCC.O=S(=O)([O-])OOS(=O)(=O)[O-].[NH4+] | C=CC(=O)NC(O)C(=O)O | null | null | O | Protection | OtherReaction | 7dd18ac173b664dbe8787dde28b3f34e4ddb6207911b20b612c95781ab96d2a1 | f1349a5de3352191cf95dc132b7c21f727405f79a883393630a0ff813912baf6 | null | C-C-C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](-C)=C.O=S(=O)(-[O-])-O-[O;H0;D2;+0:9]-S(=O)(=O)-[O-].[NH4+;D0:10]>>[C;D1;H2:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:6](=[O;D1;H0:7])-[OH;D1;+0:5] | null | [] | 80 | CELSIUS | null | null | Into a polymerization vessel equipped with a reflux condenser, stirrer rod and thermometer, is added an emulsion consisting of 44 parts by weight of methyl methacrylate, 56 parts by weight of n-butyl-acrylate, 61.5 parts by weight of completely deionized water, 1.5 parts by weight of the sodium salt of a sulfated addit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Peroxide.Vinyl | Carboxylic acid.Secondary amide.Secondary alcohol | null | null | null | HO- | O | 80 | null | C=C(C)C(=O)OC.C=CC(=O)OCCCC.O=S(=O)([O-])OOS(=O)(=O)[O-].[NH4+]>O>C=CC(=O)NC(O)C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-641689d78f1e402c9f9195a831d149ca | CN(C)C=O.Nc1ncnc2nc[nH]c12>>Nc1ncnc2c1ncn2C=CC=O | [Cl-].[NH4+].N1=CN=C2N=CNC2=C1N.CN(C=O)C.[O-]CC.[Na+]>>N1=CN=C2N(C=NC2=C1N)C=CC=O | CN([CH3:7])[CH:13]=[O:14].[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[n:8][cH:9][nH:10][c:11]12>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[CH:11]=[CH:12][CH:13]=[O:14] | CN(C)C=O.Nc1ncnc2nc[nH]c12 | Nc1ncnc2c1ncn2C=CC=O | null | null | C(C)O | C-C Coupling | OtherReaction | d655facb8f38ff560ff95f6191a4dfeca7c47eeaa8b43c51dd2ad95f85a20c65 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ncc2nc[nH]c2n1 | C-N(-[CH3;D1;+0:1])-[CH;D2;+0:2]=[O;D1;H0:3].[N;D1;H2:4]-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9]2:[n;H0;D2;+0:10]:[c:11]:[nH;D2;+0:12]:[c;H0;D3;+0:13]:1:2>>[N;D1;H2:4]-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9]2:[c;H0;D3;+0:1]:1:[n;H0;D2;+0:10]:[c:11]:[n;H0;D3;+0:12]:2-[CH;D2;+0:13]=[C:14]-[C... | 52.9 | [{"value": 52.9, "product": "N1=CN=C2N(C=NC2=C1N)C=CC=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of adenine (135 mg; 1 mmole) in dimethylformamide (2 ml) at -40° there is added a solution of sodium ethoxide (prepared from 15 mg of sodium hydride) in ethanol (1 ml) and the mixture is stirred for 10 min. Propargyl aldehyde (59 mg; 1.1 mmole) is added in one portion and stirring is continued at -40° f... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ncc2nc[nH]c2n1 | c1ncnc2nc[nH]c12 | c1ncnc2nc[nH]c12 | Other | C(C)O | null | 0.166667 | CN(C)C=O.Nc1ncnc2nc[nH]c12>C(C)O>Nc1ncnc2c1ncn2C=CC=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-358b3d5ba0e5479496f40cd68ccde256 | CN(C)C=O.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@@](O)(C=CC=O)[C@@H](CO)O2)c(=O)[nH]c1=O | [C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1.CN(C=O)C.C(C)N(CC)CC>>[C@@H]1(C[C@](O)([C@@H](CO)O1)C=CC=O)N1C(=O)NC(=O)C(C)=C1 | N([CH3:9])([CH3:10])[CH:11]=[O:12].[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21]>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@@:7]([OH:8])([CH:9]=[CH:10][CH:11]=[O:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21] | CN(C)C=O.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O | Cc1cn([C@H]2C[C@@](O)(C=CC=O)[C@@H](CO)O2)c(=O)[nH]c1=O | null | null | null | C-C Coupling | OtherReaction | ce6a764b46b701752c9b05017b110d4a19cac53de4432b6a661e1c9d6ac4500e | a8cca5f4ef4471a5e1db0a9fc83f3db7b644c8e5c53782bcb0a1c2810ffa5013 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | [CH3;D1;+0:1]-N(-[CH3;D1;+0:2])-[CH;D2;+0:3]=[O;D1;H0:4].[C:5]-[C:6]1-[#8:7]-[C:8]-[C:9]-[C@@H;D3;+0:10]-1-[O;D1;H1:11]>>[C:5]-[C:6]1-[#8:7]-[C:8]-[C:9]-[C@@;H0;D4;+0:10]-1(-[O;D1;H1:11])-[CH;D2;+0:2]=[CH;D2;+0:1]-[CH;D2;+0:3]=[O;D1;H0:4] | 35 | [{"value": 35.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Thymidine (488 mg, 2 mmol) is dissolved in dimethylformamide (4 ml), triethylamine (280 μl; 2 mmole) is added and the mixture is stirred for 1 hr. then cooled to -78°. Propargyl aldehyde (200 μl; 4 mmole) is added and the mixture is stirred at this temperature for 2 hrs. and then allowed to come to room temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Secondary alcohol | Aldehyde.Tertiary alcohol | C1CCOC1 | C1CCOC1 | c1cncnc1.C1CCOC1 | Other | null | null | 1 | CN(C)C=O.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O>>Cc1cn([C@H]2C[C@@](O)(C=CC=O)[C@@H](CO)O2)c(=O)[nH]c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-151fb1f329b940ba95ba25455a784d4b | CCOC(C)=O.CO.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=CC=C[C@]1(O)C[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1CO | C(C)(=O)OCC.[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1.C(C)N(CC)CC.CO>>[C@@H]1(C[C@](O)([C@@H](CO)O1)C=CC=O)N1C(=O)NC(=O)C=C1 | CCO[C:2](=[O:1])[CH3:3].O[CH3:4].[C@H:5]1([OH:6])[CH2:7][C@H:8]([n:9]2[cH:10][cH:11][c:12](=[O:13])[nH:14][c:15]2=[O:16])[O:17][C@@H:18]1[CH2:19][OH:20]>>[O:1]=[CH:2][CH:3]=[CH:4][C@:5]1([OH:6])[CH2:7][C@H:8]([n:9]2[cH:10][cH:11][c:12](=[O:13])[nH:14][c:15]2=[O:16])[O:17][C@@H:18]1[CH2:19][OH:20] | CCOC(C)=O.CO.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 | O=CC=C[C@]1(O)C[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1CO | null | null | null | C-C Coupling | OtherReaction | 10483adf4605591fa9e645fc5b98369036fec3737289daa7efa9a6d5ca7f8403 | c76599389d33b00140dba332172bfe40f4da2ec4feddf6bf10a5bb43b32cd039 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-C-O-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].O-[CH3;D1;+0:4].[C:5]-[C:6]1-[#8:7]-[C:8]-[C:9]-[C@@H;D3;+0:10]-1-[O;D1;H1:11]>>[C:5]-[C:6]1-[#8:7]-[C:8]-[C:9]-[C@@;H0;D4;+0:10]-1(-[O;D1;H1:11])-[CH;D2;+0:4]=[CH;D2;+0:2]-[CH;D2;+0:1]=[O;D1;H0:3] | 34 | [{"value": 34.0, "product": "[C@@H]1(C[C@](O)([C@@H](CO)O1)C=CC=O)N1C(=O)NC(=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure used in Example IV is followed utilizing 2'-deoxyuridine (456 mg; 2 mmole) triethylamine (280 μl; 2 mmole) and propargyl aldehyde (200 μl; 4 mmole) to obtain, after preparative TLC (eluant 5% methanol in ethyl acetate), the desired title compound as a pale yellow oil (190 mg; 34% yield) pure by TLC analys... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Methanol | Aldehyde.Tertiary alcohol | C1CCOC1 | C1CCOC1 | C1CCOC1.c1ccncn1 | HO- | null | null | null | CCOC(C)=O.CO.O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1>>O=CC=C[C@]1(O)C[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1CO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4b6f99895a6949e0951fbb44073175d2 | C#C.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.[C-]#N>>Cc1cn([C@H]2C[C@@](O)(C=CC#N)[C@@H](CO)O2)c(=O)[nH]c1=O | [C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1.C(C)N(CC)CC.[C-]#N.C#C>>[C@@H]1(C[C@](O)([C@@H](CO)O1)C=CC#N)N1C(=O)NC(=O)C(C)=C1 | [CH:9]#[CH:10].[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21].[C-:11]#[N:12]>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@@:7]([OH:8])([CH:9]=[CH:10][C:11]#[N:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[nH:19][c:20]1=[O:21] | C#C.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.[C-]#N | Cc1cn([C@H]2C[C@@](O)(C=CC#N)[C@@H](CO)O2)c(=O)[nH]c1=O | null | null | null | C-C Coupling | OtherReaction | 4f5d1efae148e2e95d8c7cb742e9461e97215485f9f0ce653da674a7be2f89c5 | ec5d9fc71dffdbf67886d3e506e7ceb040b07ee52e367c0cf40fa028df8e5bea | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | [C-;H0;D1:1]#[N;D1;H0:2].[CH;D1;+0:3]#[CH;D1;+0:4].[C:5]-[C:6]1-[#8:7]-[C:8]-[C:9]-[C@@H;D3;+0:10]-1-[O;D1;H1:11]>>[C:5]-[C:6]1-[#8:7]-[C:8]-[C:9]-[C@@;H0;D4;+0:10]-1(-[O;D1;H1:11])-[CH;D2;+0:4]=[CH;D2;+0:3]-[C;H0;D2;+0:1]#[N;D1;H0:2] | null | [] | null | null | null | null | The title compound is obtained by following essentially the same method described in Example V. Thus starting from thymidine (360 mg, 1.5 mmol), triethylamine (210 μl, 1.5 mmol) and acetylene cyanide. (152 mg, 3 mmol), the title compound is obtained after purification on preparative TLC (5% methanol in ethyl acetate, R... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Alkyne | Nitrile.Tertiary alcohol | C1CCOC1 | C1CCOC1 | c1cncnc1.C1CCOC1 | null | null | null | null | C#C.Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O.[C-]#N>>Cc1cn([C@H]2C[C@@](O)(C=CC#N)[C@@H](CO)O2)c(=O)[nH]c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-eea5d259ce154d80a3a765c17b71a210 | O=S(=O)([O-])[O-].O[C@@H]1[C@H]2OC[C@@H](O[C@@H]1O)[C@@H]2O>>O=C[C@H](OS(=O)(=O)O)[C@H]1OC[C@@H](O)[C@@H]1O | O[C@@H]1[C@H](O)[C@@H]2[C@@H](O)[C@H](O1)CO2.S(=O)(=O)([O-])[O-]>>S(=O)(=O)(O)O[C@@H](C=O)[C@@H]1[C@@H](O)[C@H](O)CO1 | [O-][S:5](=[O:6])(=[O:7])[O-:8].[OH:1][C@@H:2]1[C@H:3]([OH:4])[C@H:9]2[O:10][CH2:11][C@@H:12]([O:13]1)[C@@H:14]2[OH:15]>>[O:1]=[CH:2][C@H:3]([O:4][S:5](=[O:6])(=[O:7])[OH:8])[C@H:9]1[O:10][CH2:11][C@@H:12]([OH:13])[C@@H:14]1[OH:15] | O=S(=O)([O-])[O-].O[C@@H]1[C@H]2OC[C@@H](O[C@@H]1O)[C@@H]2O | O=C[C@H](OS(=O)(=O)O)[C@H]1OC[C@@H](O)[C@@H]1O | null | null | null | Acylation | OtherReaction | 769f281eff7c3ee97f840dfebb47f8145f48c81f0afa30fe5113b624bf68c44f | 6e07809921f98cd2c7e0ed7928b3ae2614ed9ef2dd637adfef30014a1980c86e | C1CCOC1 | [O-;H0;D1:1]-[S;H0;D4;+0:2](-[O-])(=[O;D1;H0:3])=[O;D1;H0:4].[OH;D1;+0:5]-[C@H;D3;+0:6]1-[O;H0;D2;+0:7]-[C:8]2-[C:9]-[#8:10]-[C:11](-[C:12]-2)-[C:13]-1-[OH;D1;+0:14]>>[O;D1;H0:3]=[S;H0;D4;+0:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[O;H0;D2;+0:14]-[C:13](-[CH;D2;+0:6]=[O;H0;D1;+0:5])-[C:11]1-[#8:10]-[C:9]-[C:8](-[OH;D1;+0:7])-[... | null | [] | null | null | null | null | Carrageenans having a moleculr weight of from 100.000 to 800.000 Dalton are known; approximately 25% sulfate-content; various types: kappa-carrageenan: comprised of alternating 1,3 or 1,6, respectively, linked 3,6-anhydro-α-D-galactose and D-galactose-4-sulfate; gel-forming; only partially oxidizable lambda carrageenan... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Secondary alcohol | Aldehyde.Secondary alcohol.Sulfate | C1C[C@@H]2C[C@@H](CO2)O1 | null | C1CCOC1 | Other | null | null | null | O=S(=O)([O-])[O-].O[C@@H]1[C@H]2OC[C@@H](O[C@@H]1O)[C@@H]2O>>O=C[C@H](OS(=O)(=O)O)[C@H]1OC[C@@H](O)[C@@H]1O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f9d2463dc43f455aa100ca6eb792b428 | Cc1c([N+](=O)[O-])cc[n+]([O-])c1C.OCC(F)(F)C(F)F>>Cc1c(OCC(F)(F)C(F)F)cc[n+]([O-])c1C | CC1=[N+](C=CC(=C1C)[N+](=O)[O-])[O-].FC(CO)(C(F)F)F.CC(C)([O-])C.[K+]>>CC1=[N+](C=CC(=C1C)OCC(C(F)F)(F)F)[O-] | O=[N+]([O-])[c:3]1[c:2]([CH3:1])[c:16]([CH3:17])[n+:14]([O-:15])[cH:13][cH:12]1.[OH:4][CH2:5][C:6]([F:7])([F:8])[CH:9]([F:10])[F:11]>>[CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[CH:9]([F:10])[F:11])[cH:12][cH:13][n+:14]([O-:15])[c:16]1[CH3:17] | Cc1c([N+](=O)[O-])cc[n+]([O-])c1C.OCC(F)(F)C(F)F | Cc1c(OCC(F)(F)C(F)F)cc[n+]([O-])c1C | null | null | O | Functional Group Interconversion | OtherReaction | 936d99471ea23de6bb74bd9dfa4853c4e7f9ce3385bfcedd89499f7c22b9b426 | 3990f9215b5a078e088ba5bbd0b8243e92e0f699f4ee1f20fbddffff29ec99ce | c1cc[nH+]cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a;+:4](-[O;-;D1;H0:5]):[c:6](-[C;D1;H3:7]):[c:8]:1-[C;D1;H3:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a;+:4](-[O;-;D1;H0:5]):[c:6](-[C;D1;H3:7]):[c:8]:1-[C;D1;H3:9] | null | [] | null | null | null | null | In 2,2,3,3-tetrafluoropropanol (10 ml) was dissolved 2,3-dimethyl-4-nitropyridine-1-oxide (2 g). To the solution was added potassium t-butoxide (1.6 g) little by little at room temperature. The mixture was then heated at 80°-90° C. for 22 hours. The reaction solution was diluted with water, which was subjected to extra... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Ether | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | O | null | null | Cc1c([N+](=O)[O-])cc[n+]([O-])c1C.OCC(F)(F)C(F)F>O>Cc1c(OCC(F)(F)C(F)F)cc[n+]([O-])c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e4ff6077d17347fd9c757525513074bb | Cc1c([N+](=O)[O-])cc[n+]([O-])c1C.OCC(F)(F)C(F)(F)F>>Cc1c(OCC(F)(F)C(F)(F)F)cc[n+]([O-])c1C | CC1=[N+](C=CC(=C1C)[N+](=O)[O-])[O-].C(C)C(=O)C.FC(CO)(C(F)(F)F)F.C([O-])([O-])=O.[K+].[K+]>>CC1=[N+](C=CC(=C1C)OCC(C(F)(F)F)(F)F)[O-] | O=[N+]([O-])[c:3]1[c:2]([CH3:1])[c:17]([CH3:18])[n+:15]([O-:16])[cH:14][cH:13]1.[OH:4][CH2:5][C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12]>>[CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][n+:15]([O-:16])[c:17]1[CH3:18] | Cc1c([N+](=O)[O-])cc[n+]([O-])c1C.OCC(F)(F)C(F)(F)F | Cc1c(OCC(F)(F)C(F)(F)F)cc[n+]([O-])c1C | null | null | CN(P(N(C)C)(N(C)C)=O)C | Functional Group Interconversion | OtherReaction | 936d99471ea23de6bb74bd9dfa4853c4e7f9ce3385bfcedd89499f7c22b9b426 | 3990f9215b5a078e088ba5bbd0b8243e92e0f699f4ee1f20fbddffff29ec99ce | c1cc[nH+]cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a;+:4](-[O;-;D1;H0:5]):[c:6](-[C;D1;H3:7]):[c:8]:1-[C;D1;H3:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a;+:4](-[O;-;D1;H0:5]):[c:6](-[C;D1;H3:7]):[c:8]:1-[C;D1;H3:9] | null | [] | null | null | null | null | A mixture of 2,3-dimethyl-4-nitropyridine-1-oxide (2.0 g), methyl ethyl ketone (30 ml), 2,2,3,3,3-pentafluoropropanol (3.05 ml), anhydrous potassium carbonate (3.29 g) and hexamethyl phosphoric acid triamide (2.07 g) was heated at 70°-80° C. for 4.5 days under stirring, then insolubles were filtered off. The filtrate w... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Ether | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | CN(P(N(C)C)(N(C)C)=O)C | null | null | Cc1c([N+](=O)[O-])cc[n+]([O-])c1C.OCC(F)(F)C(F)(F)F>CN(P(N(C)C)(N(C)C)=O)C>Cc1c(OCC(F)(F)C(F)(F)F)cc[n+]([O-])c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3385d19c944a4f86b62403eb7a76a7a4 | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.Cc1c(OCC(F)(F)C(F)F)cc[n+]([O-])c1C>>Cc1c(OCC(F)(F)C(F)F)ccnc1CO | CC1=[N+](C=CC(=C1C)OCC(C(F)F)(F)F)[O-].CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C>>OCC1=NC=CC(=C1C)OCC(C(F)F)(F)F | CC(=O)OCc1c2ccccc2c(C[O:17]C(C)=O)c2ccccc12.[O-][n+:14]1[cH:13][cH:12][c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[CH:9]([F:10])[F:11])[c:2]([CH3:1])[c:15]1[CH3:16]>>[CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[CH:9]([F:10])[F:11])[cH:12][cH:13][n:14][c:15]1[CH2:16][OH:17] | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.Cc1c(OCC(F)(F)C(F)F)cc[n+]([O-])c1C | Cc1c(OCC(F)(F)C(F)F)ccnc1CO | null | S(O)(O)(=O)=O | null | Protection | OtherReaction | 28720b12c3ae6d49805be44c6c8dae75606448e55e6da97023d076b64636c6a7 | f4e7e0d4941a86584eaaed937e76f42a56dc8862ee4e8ee737501eefde178d5a | c1ccncc1 | C-C(=O)-O-C-c1:c2:c:c:c:c:c:2:c(-C-[O;H0;D2;+0:1]-C(-C)=O):c2:c:c:c:c:c:1:2.[CH3;D1;+0:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-]):[c:6]:[c:7]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7] | null | [] | 110 | CELSIUS | 4 | HOUR | Concentrated sulfuric acid (two drops) was added to a solution of 2,3-dimethyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine-1-oxide (2.6 g) in acetic anydride (8 ml). The mixture was stirred at 110° C. for 4 hours, which was then concentrated. The residue was dissolved in methanol (20 ml), to which was added sodium hydroxide... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Primary alcohol | c1ccc2cc3ccccc3cc2c1.C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HO- | S(O)(O)(=O)=O | 110 | 4 | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.Cc1c(OCC(F)(F)C(F)F)cc[n+]([O-])c1C>S(O)(O)(=O)=O>Cc1c(OCC(F)(F)C(F)F)ccnc1CO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3d944872a4c84c12aebb7d0274d5ef22 | Cc1c[n+]([O-])cc(C)c1[N+](=O)[O-].OCC(F)(F)C(F)(F)F>>Cc1c[n+]([O-])cc(C)c1OCC(F)(F)C(F)(F)F | C(Cl)(Cl)Cl.CC=1C=[N+](C=C(C1[N+](=O)[O-])C)[O-].CC(C)([O-])C.[K+].FC(CO)(C(F)(F)F)F>>CC=1C=[N+](C=C(C1OCC(C(F)(F)F)(F)F)C)[O-] | O=[N+]([O-])[c:9]1[c:2]([CH3:1])[cH:3][n+:4]([O-:5])[cH:6][c:7]1[CH3:8].[OH:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18]>>[CH3:1][c:2]1[cH:3][n+:4]([O-:5])[cH:6][c:7]([CH3:8])[c:9]1[O:10][CH2:11][C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[F:18] | Cc1c[n+]([O-])cc(C)c1[N+](=O)[O-].OCC(F)(F)C(F)(F)F | Cc1c[n+]([O-])cc(C)c1OCC(F)(F)C(F)(F)F | null | null | null | Functional Group Interconversion | OtherReaction | 936d99471ea23de6bb74bd9dfa4853c4e7f9ce3385bfcedd89499f7c22b9b426 | 3990f9215b5a078e088ba5bbd0b8243e92e0f699f4ee1f20fbddffff29ec99ce | c1cc[nH+]cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4]:[#7;a;+:5](-[O;-;D1;H0:6]):[c:7]:[c:8]:1-[C;D1;H3:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4]:[#7;a;+:5](-[O;-;D1;H0:6]):[c:7]:[c:8]:1-[C;D1;H3:9] | 80.6 | [{"value": 80.6, "product": "CC=1C=[N+](C=C(C1OCC(C(F)(F)F)(F)F)C)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 18 | HOUR | To a solution of 3,5-dimethyl-4-nitropyridine-1-oxide (2.0 g) in 2,2,3,3,3-pentafluoropropanol (10 g) was added at 0° C. little by little potassium t-butoxide (2 g) over 15 minutes. The mixture was stirred at 60° C. for 18 hours. To the reaction mixture was added chloroform, which was subjected to filtration with celit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Ether | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | null | 60 | 18 | Cc1c[n+]([O-])cc(C)c1[N+](=O)[O-].OCC(F)(F)C(F)(F)F>>Cc1c[n+]([O-])cc(C)c1OCC(F)(F)C(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e0da6059df4742e89025b6e0cf1ca225 | COS(=O)(=O)OC.Cc1c[n+]([O-])cc(C)c1OCC(F)(F)C(F)(F)F>>Cc1cnc(CO)c(C)c1OCC(F)(F)C(F)(F)F | CC=1C=[N+](C=C(C1OCC(C(F)(F)F)(F)F)C)[O-].S(=O)(=O)(OC)OC.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+]>>CC=1C(=NC=C(C1OCC(C(F)(F)F)(F)F)C)CO | COS(=O)(=O)[O:7][CH3:6].[O-][n+:4]1[cH:3][c:2]([CH3:1])[c:10]([O:11][CH2:12][C:13]([F:14])([F:15])[C:16]([F:17])([F:18])[F:19])[c:8]([CH3:9])[cH:5]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([CH2:6][OH:7])[c:8]([CH3:9])[c:10]1[O:11][CH2:12][C:13]([F:14])([F:15])[C:16]([F:17])([F:18])[F:19] | COS(=O)(=O)OC.Cc1c[n+]([O-])cc(C)c1OCC(F)(F)C(F)(F)F | Cc1cnc(CO)c(C)c1OCC(F)(F)C(F)(F)F | null | null | O.CO | C-C Coupling | OtherReaction | 6d193ace7094051a919e223dad8dd5e46cbbd1f12da2faffcb6d9feb405fd956 | 500d1582864ea12492c385b56253ca58954536df30f0d8eeff0cd9bd06fff224 | c1ccncc1 | C-O-S(=O)(=O)-[O;H0;D2;+0:1]-[CH3;D1;+0:2].[C;D1;H3:3]-[c:4]1:[c:5]:[c:6]:[c:7]:[n+;H0;D3:8](-[O-]):[cH;D2;+0:9]:1>>[C;D1;H3:3]-[c:4]1:[c:5]:[c:6]:[c:7]:[n;H0;D2;+0:8]:[c;H0;D3;+0:9]:1-[CH2;D2;+0:2]-[OH;D1;+0:1] | null | [] | 120 | CELSIUS | 30 | MINUTE | A mixture of 3,5-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide (2.5 g) and dimethyl sulfate (1 ml) was heated at 120° C. for 30 minutes, to which was then added methanol (12.5 ml). To the mixture was added dropwise at 80° C. ammonium persulfate (4.3 g) dissolved in water (20 ml)-methanol (10 ml) over 30 min... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HO- | O.CO | 120 | 0.5 | COS(=O)(=O)OC.Cc1c[n+]([O-])cc(C)c1OCC(F)(F)C(F)(F)F>O.CO>Cc1cnc(CO)c(C)c1OCC(F)(F)C(F)(F)F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-476b763d978042baa4c140cbda1fb6b6 | Cc1c(OCC(F)(F)C(F)(F)F)ccnc1CSc1nc2ccccc2[nH]1.O=C(OO)c1cccc(Cl)c1>>Cc1c(OCC(F)(F)C(F)(F)F)ccnc1CS(=O)c1nc2ccccc2[nH]1 | CC=1C(=NC=CC1OCC(C(F)(F)F)(F)F)CSC=1NC2=C(N1)C=CC=C2.ClC1=CC(=CC=C1)C(=O)OO>>CC=1C(=NC=CC1OCC(C(F)(F)F)(F)F)CS(=O)C=1NC2=C(N1)C=CC=C2 | [CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][n:15][c:16]1[CH2:17][S:18][c:20]1[n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[nH:28]1.O=C(O[OH:19])c1cccc(Cl)c1>>[CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][n:15][c:16]1[CH2:... | Cc1c(OCC(F)(F)C(F)(F)F)ccnc1CSc1nc2ccccc2[nH]1.O=C(OO)c1cccc(Cl)c1 | Cc1c(OCC(F)(F)C(F)(F)F)ccnc1CS(=O)c1nc2ccccc2[nH]1 | null | null | C(Cl)(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=S(Cc1ccccn1)c1nc2ccccc2[nH]1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#7;a:2]:[c:3]-[C:4]-[S;H0;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[#7;a:2]:[c:3]-[C:4]-[S;H0;D3;+0:5](=[O;H0;D1;+0:1])-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 77.8 | [{"value": 77.8, "product": "CC=1C(=NC=CC1OCC(C(F)(F)F)(F)F)CS(=O)C=1NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-[3-methyl-4-(2,2,3,3,3-pentafluoropropoxy)pyrid-2-yl]methylthiobenzimidazole (2.2 g) in chloroform (20 ml) was added dropwise under ice-cooling over a period of 30 minutes m-chloroperbenzoic acid (1.3 g) dissolved in chloroform (15 ml). The solution was washed with a saturated aqueous solution of sod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccncc1.c1ccc2[nH]cnc2c1 | HCl | C(Cl)(Cl)Cl | null | null | Cc1c(OCC(F)(F)C(F)(F)F)ccnc1CSc1nc2ccccc2[nH]1.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>Cc1c(OCC(F)(F)C(F)(F)F)ccnc1CS(=O)c1nc2ccccc2[nH]1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ab075777cdf646ed84ee3c549480365d | CC1OC1(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1.c1nc[nH]n1>>CC(n1cncn1)C(O)(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1 | Cl.N1N=CN=C1.[H-].[Na+].FC(C1=CC=C(C=C1)C1(OC1C)C1=CC=C(C=C1)C(F)(F)F)(F)F>>FC(C1=CC=C(C=C1)C(C(C)N1N=CN=C1)(O)C1=CC=C(C=C1)C(F)(F)F)(F)F | [CH3:1][CH:2]1[C:8]([c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)([c:20]2[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]2)[O:9]1.[nH:3]1[cH:4][n:5][cH:6][n:7]1>>[CH3:1][CH:2]([n:3]1[cH:4][n:5][cH:6][n:7]1)[C:8]([OH:9])([c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17]... | CC1OC1(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1.c1nc[nH]n1 | CC(n1cncn1)C(O)(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 28a0254009916c6c546927d7927691482e70d5ce5f7580284682740d091ca734 | 64c863766284618c8c914b50974c3faab567499928c69890adf3711c924533f0 | c1ccc(C(Cn2cncn2)c2ccccc2)cc1 | [#7;a:1]1:[c:2]:[nH;D2;+0:3]:[#7;a:4]:[c:5]:1.[C;D1;H3:6]-[CH;D3;+0:7]1-[O;H0;D2;+0:8]-[C:9]-1(-[c:10])-[c:11]>>[C;D1;H3:6]-[CH;D3;+0:7](-[n;H0;D3;+0:3]1:[#7;a:4]:[c:5]:[#7;a:1]:[c:2]:1)-[C:9](-[OH;D1;+0:8])(-[c:10])-[c:11] | null | [] | 100 | CELSIUS | 1.5 | HOUR | 1,2,4-1H-triazole was added to a stirred suspension of sodium hydride (0.86 g., 50% dispersion, washed with petroleum ether to remove oil) in dry dimethylformamide (40 cm3). After stirring for 1.5 hours, the oxirane (formed in (b) above) dissolved in dimethylformamide (5 cm3) was added slowly. The mixture was heated at... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol | C1CO1.c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.c1ccccc1 | null | O.CN(C=O)C | 100 | 1.5 | CC1OC1(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1.c1nc[nH]n1>O.CN(C=O)C>CC(n1cncn1)C(O)(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-053fd1b6192942fb9e9834543cbccf19 | COC(=O)C(C)n1cccn1.FC(F)(F)Oc1ccc(Br)cc1>>CC(n1cccn1)C(O)(c1ccc(OC(F)(F)F)cc1)c1ccc(OC(F)(F)F)cc1 | N1(N=CC=C1)C(C(=O)OC)C.Cl.FC(OC1=CC=C(C=C1)Br)(F)F.[Mg].II>>FC(OC1=CC=C(C=C1)C(C(C)N1N=CC=C1)(O)C1=CC=C(C=C1)OC(F)(F)F)(F)F | [CH3:1][CH:2]([n:3]1[cH:4][cH:5][cH:6][n:7]1)[C:8](=[O:9])[O:25][CH3:10].Br[c:21]1[cH:20][cH:19][c:13]([O:14][C:15]([F:16])([F:17])[F:27])[cH:12][cH:31]1>>[CH3:1][CH:2]([n:3]1[cH:4][cH:5][cH:6][n:7]1)[C:8]([OH:9])([c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1)[c:21]1[cH:22][cH:23][c:24]... | COC(=O)C(C)n1cccn1.FC(F)(F)Oc1ccc(Br)cc1 | CC(n1cccn1)C(O)(c1ccc(OC(F)(F)F)cc1)c1ccc(OC(F)(F)F)cc1 | null | null | O1CCCC1.O | Aromatic Heterocycle Formation | OtherReaction | b63d9db219d3790bdbe18ba0b03d98396c5b533b736c00e63215774ae9aeff2b | f1554405a30d089a25ef669848c81974272a39dcedeef0a7744cdc34791d9519 | c1ccc(C(Cn2cccn2)c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3]:[c:4](-[#8:5]-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;H0;D1;+0:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:1.[#7;a:12]-[C:13](-[C;D1;H3:14])-[C;H0;D3;+0:15](=[O;H0;D1;+0:16])-[O;H0;D2;+0:17]-[CH3;D1;+0:18]>>[#7;a:12]-[C:13](-[C;D1;H3:14])-[C;H0;D4;+0:15](-[OH;D1;+0:16])(-[c;H0;D3;+0:18]1... | 8.6 | [{"value": 8.6, "product": "FC(OC1=CC=C(C=C1)C(C(C)N1N=CC=C1)(O)C1=CC=C(C=C1)OC(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 4-trifluoromethoxybromobenzene (6.3 g.) in dry tetrahydrofuran (40 cm3) was added dropwise to a stirred mixture of magnesium turnings (0.62 g.), dry tetrahydrofuran (10 cm3) and a crystal of iodine under a nitrogen atmosphere. The reaction commenced after about 3 cm3 of the solution had been added and the... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Ester.Ether | Trifluoro group.Trifluoro group.Ether.Ether.Tertiary alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1cn[nH]c1.c1ccccc1.c1ccccc1 | Br- | O1CCCC1.O | null | 2 | COC(=O)C(C)n1cccn1.FC(F)(F)Oc1ccc(Br)cc1>O1CCCC1.O>CC(n1cccn1)C(O)(c1ccc(OC(F)(F)F)cc1)c1ccc(OC(F)(F)F)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dbbba0078ad54f84ae7168e12023cf15 | COC(=O)C(C)n1cncn1.FC(F)(F)Oc1ccc(Br)cc1>>CC(n1cncn1)C(O)(c1ccc(OC(F)(F)F)cc1)c1ccc(OC(F)(F)F)cc1 | FC(OC1=CC=C(C=C1)Br)(F)F.[Mg].N1(N=CN=C1)C(C(=O)OC)C.II>>FC(OC1=CC=C(C=C1)C(C(C)N1N=CN=C1)(O)C1=CC=C(C=C1)OC(F)(F)F)(F)F | [CH3:1][CH:2]([n:3]1[cH:4][n:5][cH:6][n:7]1)[C:8](=[O:9])[O:25][CH3:21].Br[c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[CH3:1][CH:2]([n:3]1[cH:4][n:5][cH:6][n:7]1)[C:8]([OH:9])([c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1)[c:21]1[cH:22][cH:23][c:24]([... | COC(=O)C(C)n1cncn1.FC(F)(F)Oc1ccc(Br)cc1 | CC(n1cncn1)C(O)(c1ccc(OC(F)(F)F)cc1)c1ccc(OC(F)(F)F)cc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 1581725578b6892db858a74632b4feb223f910cc15517f5e10dd4e7b10ffab0d | 4720cfd6c4452a000eccbfdb81d12ad027e046060c2b6f667956dc61ced48f7a | c1ccc(C(Cn2cncn2)c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]-[C:7](-[C;D1;H3:8])-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[O;H0;D2;+0:11]-[CH3;D1;+0:12]>>[#7;a:6]-[C:7](-[C;D1;H3:8])-[C;H0;D4;+0:9](-[OH;D1;+0:10])(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c:15](-[O;H0;D2;+0:11]-[C:16](-[F;D1;H0:17])(-[... | 11.6 | [{"value": 11.6, "product": "FC(OC1=CC=C(C=C1)C(C(C)N1N=CN=C1)(O)C1=CC=C(C=C1)OC(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 2 | HOUR | A solution of 4-trifluoromethoxybromobenzene (9.3 g.) in dry tetrahydrofuran (40 cm3) was added dropwise to a stirred mixture of magnesium turnings (0.93 g.), dry tetrahydrofuran (15 cm3) and a crystal of iodine under a nitrogen atmosphere and at the ambient temperature. The reaction was observed to have commenced afte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Trifluoro group.Ether.Tertiary alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1nc[nH]n1.c1ccccc1.c1ccccc1 | Br- | O1CCCC1 | 40 | 2 | COC(=O)C(C)n1cncn1.FC(F)(F)Oc1ccc(Br)cc1>O1CCCC1>CC(n1cncn1)C(O)(c1ccc(OC(F)(F)F)cc1)c1ccc(OC(F)(F)F)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5b343c9424bd4933834810374e403f9e | CC(=O)Cl.CC(n1cncn1)C(O)(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1>>CC(=O)OC(c1ccc(C(F)(F)F)cc1)(c1ccc(C(F)(F)F)cc1)C(C)n1cncn1 | FC(C1=CC=C(C=C1)C(C(C)N1N=CN=C1)(O)C1=CC=C(C=C1)C(F)(F)F)(F)F.[H-].[Na+].C(C)(=O)Cl>>C(C)(=O)OC(C(C)N1N=CN=C1)(C1=CC=C(C=C1)C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F | Cl[C:2]([CH3:1])=[O:3].[OH:4][C:5]([c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1)([c:16]1[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]1)[CH:26]([CH3:27])[n:28]1[cH:29][n:30][cH:31][n:32]1>>[CH3:1][C:2](=[O:3])[O:4][C:5]([c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:1... | CC(=O)Cl.CC(n1cncn1)C(O)(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1 | CC(=O)OC(c1ccc(C(F)(F)F)cc1)(c1ccc(C(F)(F)F)cc1)C(C)n1cncn1 | null | null | O.CN(C=O)C | Acylation | Schotten-Baumann to ester | 98017bac06eb42265c00528a12d8ad0fd443a81d4f2c4b4bd7765730c559bb5b | cda6b3bfc0599ee5e7303a58cf8c674c7577cf9fbc7c186a45060ebd8ab26e4f | c1ccc(C(Cn2cncn2)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:8]>>[C:4]-[C:5](-[c:7])(-[c:8])-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 29.1 | [{"value": 29.1, "product": "C(C)(=O)OC(C(C)N1N=CN=C1)(C1=CC=C(C=C1)C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,1-Bis-(4-trifluoromethylphenyl)-2-(1,2,4-1H- triazol-1-yl)propan-1-ol (0.5 g.) was added carefully to a suspension of sodium hydride (60 mg., freed from dispersion in oil by washing with hexane) in dry dimethylformamide (20 cm3) under a nitrogen atmosphere. After stirring the mixture for 2 hours acetyl chloride (0.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1nc[nH]n1 | HCl | O.CN(C=O)C | null | null | CC(=O)Cl.CC(n1cncn1)C(O)(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1>O.CN(C=O)C>CC(=O)OC(c1ccc(C(F)(F)F)cc1)(c1ccc(C(F)(F)F)cc1)C(C)n1cncn1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c4cc47b5c6174bd9a055b86afe362b76 | ClCCCCOCCl.Clc1nc(Cl)c(Cl)[nH]1>>ClCCCCOCn1c(Cl)nc(Cl)c1Cl | ClCCCCOCCl.[Na].ClC=1NC(=C(N1)Cl)Cl.[H-].[Na+]>>ClCCCCOCN1C(=NC(=C1Cl)Cl)Cl | Cl[CH2:7][O:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1].[nH:8]1[c:9]([Cl:10])[n:11][c:12]([Cl:13])[c:14]1[Cl:15]>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][n:8]1[c:9]([Cl:10])[n:11][c:12]([Cl:13])[c:14]1[Cl:15] | ClCCCCOCCl.Clc1nc(Cl)c(Cl)[nH]1 | ClCCCCOCn1c(Cl)nc(Cl)c1Cl | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1c[nH]cn1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9](-[Cl;D1;H0:10]):[nH;D2;+0:11]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:9](-[Cl;D1;H0:10]):[c:7](-[Cl;D1;H0:8]):[#7;a:6]:[c:5]:1-[Cl;D1;H0:4] | 70.9 | [{"value": 70.9, "product": "ClCCCCOCN1C(=NC(=C1Cl)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of a sodium salt, prepared from 0.69 g of 2,4,5-trichloroimidazole and 0.16 g of 60% oil-based sodium hydride, in 5 ml of N,N-dimethylformamide was added dropwise 0.63 g of 4-chlorobutoxymethyl chloride at room temperature. After stirring at room temperature for 3 hours, 50 ml of water was added to the re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HCl | O.CN(C=O)C | null | 3 | ClCCCCOCCl.Clc1nc(Cl)c(Cl)[nH]1>O.CN(C=O)C>ClCCCCOCn1c(Cl)nc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d34625343e7649b5af49a1270004d653 | BrCCCCOCBr.Brc1nc(Br)c(Br)[nH]1>>BrCCCCOCn1c(Br)nc(Br)c1Br | BrCCCCOCBr.[Na].BrC=1NC(=C(N1)Br)Br.[H-].[Na+]>>BrCCCCOCN1C(=NC(=C1Br)Br)Br | Br[CH2:7][O:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1].[nH:8]1[c:9]([Br:10])[n:11][c:12]([Br:13])[c:14]1[Br:15]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][n:8]1[c:9]([Br:10])[n:11][c:12]([Br:13])[c:14]1[Br:15] | BrCCCCOCBr.Brc1nc(Br)c(Br)[nH]1 | BrCCCCOCn1c(Br)nc(Br)c1Br | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[#8:2]-[C:3].[Br;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7](-[Br;D1;H0:8]):[c:9](-[Br;D1;H0:10]):[nH;D2;+0:11]:1>>[Br;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7](-[Br;D1;H0:8]):[c:9](-[Br;D1;H0:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[#8:2]-[C:3] | 39.3 | [{"value": 39.3, "product": "BrCCCCOCN1C(=NC(=C1Br)Br)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of a sodium salt, prepared from 1.22 g of 2,4,5-tribromoimidazole and 0.16 g of 60% oil-based sodium hydride, in 5 ml of N,N-dimethylformamide was added dropwise 1.23 g of 4-bromobutoxymethyl bromide at room temperature. After stirring at room temperature for 3 hours, 50 ml of water was added to the react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HBr | O.CN(C=O)C | null | 3 | BrCCCCOCBr.Brc1nc(Br)c(Br)[nH]1>O.CN(C=O)C>BrCCCCOCn1c(Br)nc(Br)c1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-19260d8363044c62bef46126e599e8c7 | Cc1c(CO)cccc1-n1cccc1>>Cc1c(C=O)cccc1-n1cccc1 | N1(C=CC=C1)C=1C(=C(CO)C=CC1)C>>N1(C=CC=C1)C=1C(=C(C=O)C=CC1)C | [CH3:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][cH:7][cH:8][c:9]1-[n:10]1[cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][cH:7][cH:8][c:9]1-[n:10]1[cH:11][cH:12][cH:13][cH:14]1 | Cc1c(CO)cccc1-n1cccc1 | Cc1c(C=O)cccc1-n1cccc1 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4] | C1=CC=CC=C1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-n2cccc2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 82.4 | [{"value": 82.4, "product": "N1(C=CC=C1)C=1C(=C(C=O)C=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A suspension of 6 g of (3-pyrrol-1-yl)2-methylbenzyl alcohol, 300 ml of benzene and 30 g of manganese dioxide was stirred at room temperature for 3 hours and 12 g of manganese dioxide were added thereto. After stirring for 2 hours, another 6 g of manganese dioxide were added to the mixture which was then stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1cc[nH]c1 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C1=CC=CC=C1 | null | 3 | Cc1c(CO)cccc1-n1cccc1>[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C1=CC=CC=C1>Cc1c(C=O)cccc1-n1cccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-912f5ab9171743f2899efb12b84534f2 | CC(=O)OC(C)=O.Cc1cccc(N)n1>>CC(=O)Nc1cccc(C)n1 | NC1=CC=CC(=N1)C.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=CC=CC(=N1)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[n:11]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[n:11]1 | CC(=O)OC(C)=O.Cc1cccc(N)n1 | CC(=O)Nc1cccc(C)n1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccncc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | null | null | A mixture of 50 g of 6-amino-2-methyl-pyridine in 250 ml of acetic acid anhydride was refluxed for one hour and was then evaporated to dryness under reduced pressure. The residue was taken up in methylene chloride and the solution was washed with water and then with aqueous sodium hydroxide solution and then with water... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | null | null | null | CC(=O)OC(C)=O.Cc1cccc(N)n1>>CC(=O)Nc1cccc(C)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7ab193707983430c94d04bf84c07320d | COC(=O)c1cccc(N)n1.COC1CCC(OC)O1>>COC(=O)c1cccc(-n2cccc2)n1 | COC1OC(CC1)OC.NC1=NC(=CC=C1)C(=O)OC>>N1(C=CC=C1)C1=NC(=CC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[n:15]1.CO[CH:11]1O[CH:14](OC)[CH2:13][CH2:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][cH:12][cH:13][cH:14]2)[n:15]1 | COC(=O)c1cccc(N)n1.COC1CCC(OC)O1 | COC(=O)c1cccc(-n2cccc2)n1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 0e9d22b0723ec2930c6f0b28cb06c2d86835df697b962917265b2a52889a76e9 | 37da407ba22aeb87f9320448e7710117027e549cd7c89e722598c54789c5481f | c1ccc(-n2cccc2)nc1 | C-O-[CH;D3;+0:1]1-O-[CH;D3;+0:2](-O-C)-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[#7;a:9]:[c;H0;D3;+0:10](-[NH2;D1;+0:11]):[c:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[#7;a:9]:[c;H0;D3;+0:10](-[n;H0;D3;+0:11]1:[cH;D2;+0:1]:[cH;D2;+0:4]:[cH;D2;+0:3]:[cH;D2;+0:2]:1):[c:12]:[c:13] | null | [] | null | null | null | null | 6.3 ml of 2,5-dimethoxy-tetrahydrofuran were added with stirring at room temperature to a solution of 7 g of the product of Step C in 17.5 ml of acetic acid and was refluxed for one hour. Acetic acid was evaporated under reduced pressure and the oil residue was chromatographed over silica gel. Elution with methylene ch... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine | null | C1CCOC1 | c1cc[nH]c1 | c1ccncc1.c1cc[nH]c1 | HO- | C(C)(=O)O | null | null | COC(=O)c1cccc(N)n1.COC1CCC(OC)O1>C(C)(=O)O>COC(=O)c1cccc(-n2cccc2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-112d3b0b5e7a4589acf2c402c7916f73 | COC(=O)c1cccc(-n2cccc2)n1>>OCc1cccc(-n2cccc2)n1 | C(C(C)C)[Al]CC(C)C.N1(C=CC=C1)C1=NC(=CC=C1)C(=O)OC.C(C(O)C(O)C(=O)[O-])(=O)[O-].[K+].[Na+]>>N1(C=CC=C1)C1=NC(=CC=C1)CO | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7](-[n:8]2[cH:9][cH:10][cH:11][cH:12]2)[n:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[n:8]2[cH:9][cH:10][cH:11][cH:12]2)[n:13]1 | COC(=O)c1cccc(-n2cccc2)n1 | OCc1cccc(-n2cccc2)n1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-n2cccc2)nc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 91 | [{"value": 91.0, "product": "N1(C=CC=C1)C1=NC(=CC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 30 | MINUTE | 38 ml of diisobutyl aluminum were added dropwise over one hour at -40° C. to a solution of 3.7 g of the product of Step D in 40 ml of toluene and the mixture was stirred at -30° C. for 30 minutes. 110 ml of an aqueous molar solution of double sodium potassium tartarate were slowly added to the mixture while keeping the... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1.c1cc[nH]c1 | Other | C1(=CC=CC=C1)C | -30 | 0.5 | COC(=O)c1cccc(-n2cccc2)n1>C1(=CC=CC=C1)C>OCc1cccc(-n2cccc2)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-99a2331c88664704a50a163db33a54cd | CNC(=O)N1CCSC1c1ccccc1O.ClCCN1CCN(c2ccccc2)CC1>>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | CNC(=O)N1C(SCC1)C1=C(C=CC=C1)O.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].ClCCN1CCN(CC1)C1=CC=CC=C1>>CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1 | [CH3:1][NH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[OH:16].Cl[CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][NH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[... | CNC(=O)N1CCSC1c1ccccc1O.ClCCN1CCN(c2ccccc2)CC1 | CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 44.4 | [{"value": 44.4, "product": "CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 24 | HOUR | A mixture of 2.38 g of N-methyl-2-(2-hydroxyphenyl)thiazolidine-3-carboxamide, 1.38 g of potassium carbonate, 0.7 g of sodium iodide, 3.36 g of 1-(2-chloroethyl)-4-phenylpiperazine and 25 ml of dimethylformamide is stirred at 90° C. for 24 hours. The mixture is concentrated under reduced pressure to remove dimethylform... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | CN(C=O)C | 90 | 24 | CNC(=O)N1CCSC1c1ccccc1O.ClCCN1CCN(c2ccccc2)CC1>CN(C=O)C>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f623d20928e343859a3d62540c8f1e03 | CNC(=O)N1CCSC1c1ccccc1OCCCl.c1ccc(N2CCNCC2)cc1>>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCCl.C1(=CC=CC=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>>CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1 | Cl[CH2:18][CH2:17][O:16][c:15]1[c:10]([CH:9]2[N:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][CH2:7][S:8]2)[cH:11][cH:12][cH:13][cH:14]1.[NH:19]1[CH2:20][CH2:21][N:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][NH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:1... | CNC(=O)N1CCSC1c1ccccc1OCCCl.c1ccc(N2CCNCC2)cc1 | CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 58 | [{"value": 57.8, "product": "CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 18 | HOUR | A mixture of 1.81 g of N-methyl-2-{2-(2-chloroethyloxy)phenyl]thiazolidine-3-carboxamide, 0.97 g of N-phenylpiperazine, 0.83 g of potassium carbonate, 0.90 g of sodium iodide and 25 ml of dimethylformamide is stirred at 90° C. for 18 hours. The mixture is concentrated under reduced pressure to remove solvent. Water is ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | CN(C=O)C | 90 | 18 | CNC(=O)N1CCSC1c1ccccc1OCCCl.c1ccc(N2CCNCC2)cc1>CN(C=O)C>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f3e68c165c3c48f0b4660070a759059b | CNC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1.COC(=O)[C@H]1O[C@@H]1c1ccc(OC)cc1>>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | CNC(=S)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1.COC1=CC=C(C=C1)[C@@H]2[C@H](O2)C(=O)OC.COC1=CC=C(C=C1)[C@@H]2[C@H](O2)C(=O)OC>>CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1 | S=[C:3]([NH:2][CH3:1])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH2:30]1.COC([C@H]1O[C@@H]1c1ccc(OC)cc1)=[O:4]>>[CH3:1][NH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11... | CNC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1.COC(=O)[C@H]1O[C@@H]1c1ccc(OC)cc1 | CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | C(C)O | Miscellaneous | OtherReaction | 336ac7092eb2088a653e8f2f07c652f8606135a93855cd31fb8751c41c63aede | 02dbdc14ebc1cca2a06979873dd0f117095d62f57d7908b3f192606f48396214 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | C-O-C(=[O;H0;D1;+0:1])-[C@@H]1-O-[C@H]-1-c1:c:c:c(-O-C):c:c:1.S=[C;H0;D3;+0:2](-[#7:3]-[C;D1;H3:4])-[#7:5](-[C:6])-[C:7]-[#16:8]>>[#16:8]-[C:7]-[#7:5](-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[#7:3]-[C;D1;H3:4])-[C:6] | 75.7 | [{"value": 75.7, "product": "CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 480 mg of (+)-N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide and 339 mg of methyl trans-3-(4-methoxyphenyl)glycidate are dissolved in 40 ml of ethanol, and the solution is refluxed for 11 hours under heating. 339 mg of methyl trans-3-(4-methoxyphenyl)glycidate are added to the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Thiourea | Urea | C1CO1.c1ccccc1 | null | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | C(C)O | null | null | CNC(=S)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1.COC(=O)[C@H]1O[C@@H]1c1ccc(OC)cc1>C(C)O>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cf2b730c091b4f5fb5ea937a4065d490 | CN=C=O.c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1>>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | C1(=CC=CC=C1)N1CCN(CC1)CCOC1=C(C=CC=C1)C1SCCN1.CN=C=O>>CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1 | [CH3:1][N:2]=[C:3]=[O:4].[NH:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][NH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][S:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16... | CN=C=O.c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 | null | null | O1CCCC1 | Acylation | Urea synthesis via isocyanate and secondary amine | 882e32adae6bbfd8ff7df315e2e3a40dc1b0c23d2df706d43c8afd6621de63fa | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[c:5]-[C:6]1-[#16:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#16:7]-[C:6]-1-[c:5] | 89.7 | [{"value": 89.7, "product": "CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.7, "product": "CNC(=O)N1C(SCC1)C1=C(C=CC=C1)OCCN1CCN(CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3.69 g of 2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine are dissolved in 40 ml of tetrahydrofuran, and 0.62 g of methyl isocyanate is added thereto at room temperature. The mixture is stirred at the same temperature for 2 hours. The mixture is concentrated under reduced pressure to remove solvent. Water ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CSCN1 | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | O1CCCC1 | null | 2 | CN=C=O.c1ccc(N2CCN(CCOc3ccccc3C3NCCS3)CC2)cc1>O1CCCC1>CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2ccccc2)CC1 |
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