Isopropanol → Diazepam

HRID 262941

Reaction equation

HRID 262941 reaction equation
Br[CH2:2][C:3]([N:5]([C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)[CH3:6])=[O:4].C1N2CN3CN(C2)C[N:23]1C3.[Br-].[NH4+].C(O)(C)C>O>[Cl:21][C:18]1[CH:19]=[CH:20][C:7]2[N:5]([CH3:6])[C:3](=[O:4])[CH2:2][N:23]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]=2[CH:17]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 4101HexamethylenetetramineHCID 25514Ammonium BromideHCID 76099N-(2-benzoyl-4-chlorophenyl)-2-bromo-N-methylacetamide

Product 1

HCID 3016Diazepam

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux 1.8 g. (0.005 moles) of 2-(2-bromo-N-methylacetamido)-5-chlorobenzophenone, 2.8 g. (0.020 moles) of hexamethylenetetramine and 1.96 g. (0.020 moles) of ammonium bromide together for 2 hours in 14 ml. of 85% (v/v) aqueous isopropyl alcohol. Pour the reaction mixture into water and extract the product with benzene. Wash the benzene solution with water, dry over anhydrous sodium sulfate, filter and evaporate to dryness. After recrystallization, 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one is obtained. The material gives a single spot by thin layer chromatography, and after drying under vacuum at 110° C., shows no depression on mixed melting point with an authentic sample (M.P. 129.5°-130.5° C.).

Workup

  1. temperatureReflux 1.8 g
  2. extractionextract the product with benzene
  3. washWash the benzene solution with water
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. customevaporate to dryness
  7. customAfter recrystallization

Sources & evidence

ORD record
ord-6b061085fce449f7b748aa91c5b9620d
Source dataset
uspto-grants-1979_05
Patent number
US04155904

Linked notes

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