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

HRID 224369Notes

Reaction equation

HRID 224369 reaction equation
Br[CH:2]([F:21])[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].[NH2:22]C1C=CC(Cl)=CC=1C(C1C=CC=CC=1)=O.BrC(F)C(Br)=O.N>CCOCC>[F:21][CH:2]1[N:22]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:6]=2[NH:5][C:3]1=[O:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 128702-Amino-5-chlorobenzophenoneHCID 233325972-(alpha-Bromo-alpha-fluoroacetamido)-5-chlorobenzophenoneHCID 23332663alpha-Bromo-alpha-fluoroacetyl bromide

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.71 g. of 2-(α-bromo-α-fluoro-acetamido)-5-chlorobenzophenone, obtainable from 2-amino-5-chlorobenzophenone and α-bromo-α-fluoroacetyl bromide, in 100 ml. of ether and 60 ml. of 13% methanolic NH3 is allowed to stand for 18 hours at 20° and is evaporated. Working up in the customary manner, using water/methylene chloride, gives 3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one.

Workup

  1. customis evaporated

Sources & evidence

ORD record
ord-3be39c3562a64b79b714987da623365c
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Reaction notes

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