Ammonium Hydroxide → Nordiazepam

HRID 1973071Notes

Reaction equation

HRID 1973071 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O)=[O:4].[OH-].[NH4+:22]>C(O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:22]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]=2[CH:16]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 776355-Chloro-2-(chloroacetamido)benzophenone

Product 1

HCID 2997Nordiazepam

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a one liter, stirred flask equipped with a reflux condenser was placed 89.7 gms. of ##STR8## 61.6 gms. of 2-chloroacetamido-5-chlorobenzophenone, 22.4 mls. of 26% ammonium hydroxide and 425 mls. of ethanol. Ammonia was bubbled into the reaction mixture while it was stirred and heated to reflux. Refluxing was continued for 5 hrs. thereafter with stirring. The reaction mixture was distilled to dryness in a Swissco evaporator. The residue was then heated at reflux for one hour in a mixture of 100 mls. of toluene and 100 mls. of water and cooled to room temperature yielding 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one. The product was filtered, washed with 20 mls. of water and 20 mls. of toluene and dried. It weighed 92.5 gms. or 85.4%. The crude product melted at 210°-213° C.

Workup

  1. customequipped with a reflux condenser
  2. customAmmonia was bubbled into the reaction mixture while it
  3. stirringwas stirred
  4. temperatureheated to reflux
  5. temperatureRefluxing
  6. stirringthereafter with stirring
  7. distillationThe reaction mixture was distilled to dryness in a Swissco evaporator
  8. temperatureThe residue was then heated
  9. temperatureat reflux for one hour in a mixture of 100 mls

Sources & evidence

ORD record
ord-2930eaee533f480b87383b226a590fbe
Source dataset
uspto-grants-1976_12
Patent number
US03996209

Reaction notes

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