Hypofluorous acid, trifluoromethyl ester → 3-fluoro-1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 224366

Reaction equation

HRID 224366 reaction equation
[F:1][CH:2]1[N:8](S(C2C=CC(C)=CC=2)(=O)=O)[CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]2[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[CH:27]=[CH:28][C:5]=2[NH:4][C:3]1=[O:32].C1(C)C=CC(S(N2C(C3C=CC=CC=3)C3C=C([N+]([O-])=O)C=CC=3NC(=O)C2)(=O)=O)=CC=1.C(OF)(F)(F)F>CN(C=O)C>[F:1][CH:2]1[N:8]=[C:7]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:6]2[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[CH:27]=[CH:28][C:5]=2[NH:4][C:3]1=[O:32]

Participants

5

Reactant 3

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 233326554-p-toluenesulfonyl-5-phenyl-7-nitro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-oneHCID 233326753-fluoro-4-p-toluenesulfonyl-5-phenyl-7-nitro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one

Product 1

HCID 131259943-fluoro-1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.35 g. of sublimed potassium tert.-butylate are added at 5° to a solution of 4.55 g. of 3-fluoro-4-p-toluenesulfonyl-5-phenyl-7-nitro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one, obtainable from 4-p-toluenesulfonyl-5-phenyl-7-nitro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one and CF3OF, in 50 ml. of DMF. After stirring for 1 hour, the temperature is allowed to rise to 20° and the mixture is stirred for 48 hours more. The mixture is poured onto ice and worked up in the customary manner to give 3-fluoro-5-phenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one.

Workup

  1. customto rise to 20°
  2. stirringthe mixture is stirred for 48 hours more
  3. additionThe mixture is poured onto ice

Sources & evidence

ORD record
ord-930db9717e944bd3a8b5d05a3ffb243a
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Linked notes

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