Ammonia → 2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-(4-hydroxyphenyl)-

HRID 2083002Notes

Reaction equation

HRID 2083002 reaction equation
[NH3:1].Br[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:5]>>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:1]=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[C:8]=2[CH:9]=1

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 125173062-Bromo-N-[4-chloro-2-(4-hydroxybenzoyl)phenyl]acetamide

Product 1

HCID 870252H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-(4-hydroxyphenyl)-Yield 67%

Procedure

To 350 ml of liquid ammonia was added 60 g (0.163 mole) of 2-bromo-4'-chloro-2'-(4-hydroxybenzoyl)acetanilide. After refluxing for 3 hr, the ammonia was allowed to evaporate. The residue was heated to reflux in 400 ml of ethanol for 3 hr. Ethanol was evaproated, and 800 ml of acetone was added. This suspension was heated and filtered to remove inorganic salts. Concentration of acetone filtrate gave 31.5 g (67%) of product, mp 271°-272°.

Workup

  1. temperatureAfter refluxing for 3 hr
  2. customto evaporate
  3. temperatureThe residue was heated
  4. temperatureto reflux in 400 ml of ethanol for 3 hr
  5. addition800 ml of acetone was added
  6. temperatureThis suspension was heated
  7. filtrationfiltered
  8. customto remove inorganic salts

Sources & evidence

ORD record
ord-ffac12770dee4bc481c57ae4d9485ee4
Source dataset
uspto-grants-1978_04
Patent number
US04083948

Reaction notes

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