2-(alpha-Azido-alpha-fluoro-acetamido)-5-chlorobenzophenone → 7-Chloro-3-fluoro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 224372Notes

Reaction equation

HRID 224372 reaction equation
[H][H].[N:3]([CH:6]([F:25])[C:7]([NH:9][C:10]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)=[O:8])=[N+]=[N-]>[Pd].C(OCC)(=O)C>[F:25][CH:6]1[N:3]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:10]=2[NH:9][C:7]1=[O:8]

Participants

5

Reactant 2

HCID 233326312-(alpha-Azido-alpha-fluoro-acetamido)-5-chlorobenzophenoneHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen is passed into a solution of 3.33 g. of 2-(α-azido-α-fluoro-acetamido)-5-chlorobenzophenone in 100 ml. of ethyl acetate in the presence of 0.3 g. of 5% palladium-on-charcoal for 4 hours. After filtering off the catalyst, evaporation and working up in the customary manner, there is obtained 3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, m.p. 235° (decomposition).

Workup

  1. filtrationAfter filtering off
  2. customthe catalyst, evaporation

Sources & evidence

ORD record
ord-12d75dc30d30432189f4df5d313eb1eb
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Reaction notes

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