Ammonia → Nordiazepam

HRID 1973066Notes

Reaction equation

HRID 1973066 reaction equation
C1N2CN3CN(C2)C[N:2]1C3.Cl[CH2:12][C:13]([NH:15][C:16]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:17]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)=[O:14].N>CO>[Cl:30][C:27]1[CH:28]=[CH:29][C:16]2[NH:15][C:13](=[O:14])[CH2:12][N:2]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:17]=2[CH:26]=1

Participants

5

Reactant 3

HCID 222Ammonia3×HCID 4101HexamethylenetetramineHCID 776355-Chloro-2-(chloroacetamido)benzophenone

Product 1

HCID 2997NordiazepamYield 624.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methanol (550 mls), hexamethylenetetramine (14.1 g., 0.1 mol) and 2-chloroacetamido-5-chlorobenzophenone (308.2 g., 1.0 mol) was stirred and saturated with ammonia at room temperature. The mixture was heated slowly to reflux with a steady stream of ammonia bubbling through the solution. Refluxing was continued for 24 hours. The flow of ammonia was interrupted and the crystal slurry obtained was cooled to room temperature. The product, filtered, washed with methanol (2 × 125 ml) and hot water (4 × 500 ml), and dried gave 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (169 g., 62.3%) melting at 213° to 215° C.

Workup

  1. temperatureThe mixture was heated slowly
  2. temperatureRefluxing
  3. customthe crystal slurry obtained
  4. filtrationThe product, filtered
  5. washwashed with methanol (2 × 125 ml) and hot water (4 × 500 ml)
  6. customdried

Sources & evidence

ORD record
ord-57f62855293a4e2eb21841d79ab5dc2c
Source dataset
uspto-grants-1976_12
Patent number
US03996209

Reaction notes

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