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

HRID 224371Notes

Reaction equation

HRID 224371 reaction equation
[NH2:1][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].BrC(F)C(NC1C=CC(Cl)=CC=1C(C1C=CC=CC=1)=O)=O.N>N1C=CC=CC=1>[F:21][CH:2]1[N:1]=[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

5

Reactant 3

HCID 222AmmoniaHCID 233325972-(alpha-Bromo-alpha-fluoroacetamido)-5-chlorobenzophenoneHCID 233327012-(alpha-Amino-alpha-fluoroacetamido)-5-chlorobenzophenone

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3.07 g. of 2-(α-amino-α-fluoroacetamido)-5-chlorobenzophenone, obtainable from 2-(α-bromo-α-fluoroacetamido)-5-chlorobenzophenone and liquid NH3, in 35 ml. of pyridine is boiled for 2 hours and evaporated. Working up in the customary manner gives 3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, m.p. 235° (decomposition).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-3252695280144913a9261ccc2e671eb9
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Reaction notes

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