Ethanol → HCID 15290905, compound
Reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:30]3[CH:31]=[C:32]4[O:37][CH2:36][O:35][C:33]4=[CH:34][C:29]=3[CH2:28][C:27]([CH3:38])=[N:26][N:25]=2)=[CH:20][CH:19]=1.C(O)C>ClCCl>[C:1]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:30]3[CH:31]=[C:32]4[O:37][CH2:36][O:35][C:33]4=[CH:34][C:29]=3[CH2:28][C:27]([CH3:38])=[N:26][N:25]=2)=[CH:20][CH:19]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 25 °C
Procedure
1.0 ml (15 mmol) of benzoyl chloride and 2.1 ml (15 mmol) of triethylamine were added to a solution of 4 g (13.6 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine in dichloromethane and the reaction mixture was stirred at 25 ° C. for 24 hours. The solution was extracted with 3×30 ml of water, 3×20 ml of a 4% aqueous sodium hydroxide solution and finally with 2×30 ml of distilled water. The organic layer was dried, evaporated under reduced pressure, then the crystalline residue was treated with 20 ml of hot ethanol to obtain 3.97 g of raw product, m.p. 242°-243° C. This raw product was repeatedly treated with 20 ml of hot ethanol, next day it was filtered at 0°-5° C., washed with 3×3 ml of ethanol and dried at 100° C. to yield 3.85 g (71.3%) of the pure aimed product, m.p. 246°-247° C. (decomp.).
Workup
- extractionThe solution was extracted with 3×30 ml of water, 3×20 ml of a 4% aqueous sodium hydroxide solution and finally with 2×30 ml of distilled water
- customThe organic layer was dried
- customevaporated under reduced pressure
- additionthe crystalline residue was treated with 20 ml of hot ethanol
- customto obtain 3.97 g of raw product, m.p. 242°-243° C
- filtrationwas filtered at 0°-5° C.
- washwashed with 3×3 ml of ethanol
- customdried at 100° C.
Sources & evidence
- ORD record
- ord-b2c5ebef00ec405eaf253b6494c614e7
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05604223
Reaction notes
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