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Methanol → 1-(beta-Hydroxy-ethyl)-5-phenyl-7-chloro-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione

HRID 1283338
Notes
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Reaction equation

HRID 1283338 reaction equation
[C:1]1([N:7]2[C:13]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:19])[CH2:9][C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[CH2:23]1[O:25][CH2:24]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O>[OH:25][CH2:24][CH2:23][N:11]1[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:20])[CH2:9][C:10]1=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 6354Ethylene OxideHCID 66854Benzyltrimethylammonium hydroxideHCID 89657Desmethylclobazam

Product 1

HCID 215171751-(beta-Hydroxy-ethyl)-5-phenyl-7-chloro-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture consisting of 28.6 gm (0.1 mol) of 5-phenyl-7-chloro-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione, 500 ml of methanol, 25 ml of water, 10-15 ml of ethyleneoxide and 1 ml of Triton B (methanolic 35% solution of benzyl trimethylammonium hydroxide) was stirred at room temperature for about eight hours. Thereafter, the clear solution formed thereby was evaporated, the residue was taken up in methylene chloride, and the resulting solution was extracted with water, dried and evaporated. The residue was recrystallized from ethanol, yielding 25.6 gm (78% of theory) of the colorless crystalline compound of the formula ##SPC6##

Workup

  1. customThereafter, the clear solution formed
  2. customthereby was evaporated
  3. extractionthe resulting solution was extracted with water
  4. customdried
  5. customevaporated
  6. customThe residue was recrystallized from ethanol
  7. customyielding 25.6 gm (78% of theory) of the colorless crystalline compound of the formula

Sources & evidence

ORD record
ord-52a45b361d134fbdbe957583f0861db4
Source dataset
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE028935

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes