Ammonia → 7-Chloro-3-fluoro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 224370Notes

Reaction equation

HRID 224370 reaction equation
N.Cl[CH:3]([F:22])[C:4]([NH:6][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)=[O:5].[NH2:23]C1C=CC(Cl)=CC=1C(C1C=CC=CC=1)=O.ClC(F)C(Cl)=O>CS(C)=O>[F:22][CH:3]1[N:23]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:7]=2[NH:6][C:4]1=[O:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 128702-Amino-5-chlorobenzophenoneHCID 30138612-Chloro-2-fluoroacetyl chlorideHCID 233326282-(alpha-Chloro-alpha-fluoro-acetamido)-5-chloro-benzophenone

Product 1

HCID 131259877-Chloro-3-fluoro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

NH3 is passed into a solution of 3.26 g. of 2-(α-chloro-α-fluoro-acetamido)-5-chloro-benzophenone, obtainable from 2-amino-5-chlorobenzophenone and α-chloro-α-fluoroacetyl chloride, in 15 ml. of DMSO at 50° for one hour. After stirring for 16 hours, the mixture is evaporated; 35 ml. of chloroform and 35 ml. of 13% NHO3 are added and the resulting salt is filtered off. The product is suspended in ethanol and neutralized with ammonia. Dilution with water gives 3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, m.p. 235° (decomposition).

Workup

  1. customthe mixture is evaporated
  2. additionof 13% NHO3 are added
  3. filtrationthe resulting salt is filtered off

Sources & evidence

ORD record
ord-fa087ebf51fe4e8b97e36821ee796f99
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Reaction notes

Loading…