Reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5][CH:4]([OH:20])[C:3]1=[O:21].N1C=CC=CC=1.[CH2:28]([CH:31]([CH2:35][CH2:36][CH3:37])[C:32](Cl)=[O:33])[CH2:29][CH3:30]>CN(C)C=O>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5][CH:4]([O:20][C:32](=[O:33])[CH:31]([CH2:35][CH2:36][CH3:37])[CH2:28][CH2:29][CH3:30])[C:3]1=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 15 g of 1-methyl-7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-2-one (Temazepam) and 5 g of absolute pyridine is cooled in 40 ml of freshly distilled dimethyl formamide to -5° and is mixed drop by drop with 10.5 g of dipropyl acetic acid chloride with the exclusion of atmospheric moisture. The mixture is stirred for an additional 4 hours at -5° and is allowed to stand over night at 0°, and then the mixture is poured on ice. The separated oil crystallizes while rubbed on with ethanol. By recrystallization from petroleum ether or isopropanol using activated charcoal, one will obtain the 1-methyl-7-chloro-3-dipropylacetoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-2-one as a colorless powder with a melting point of 134°-136°.
Workup
- waitto stand over night at 0°
- additionthe mixture is poured on ice
- customThe separated oil crystallizes
- customBy recrystallization from petroleum ether or isopropanol using activated charcoal, one
Sources & evidence
- ORD record
- ord-b58383cd293c40228718e3d99a150283
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04261987
Linked notes
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