Hypofluorous acid, trifluoromethyl ester → 3-Fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 2058291Notes

Reaction equation

HRID 2058291 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10]([O:13][Si](C)(C)C)=[CH:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1.[F:25]OC(F)(F)F>ClC(Cl)(Cl)F>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([F:25])[N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 126021197-chloro-1-methyl-5-phenyl-2-trimethylsiloxy-1H-1,4-benzodiazepine

Product 1

HCID 126021203-Fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-oneYield 108.8%

Reagents, catalysts & solvents 1

HCID 6389TrichlorofluoromethaneSolvent

Procedure

A solution of 8.52 g of the aforesaid 7-chloro-1-methyl-5-phenyl-2-trimethylsiloxy-1H-1,4-benzodiazepine in 150 ml of trichlorofluoromethane was cooled to -70° C. and 2.4 g of trifluoromethyl hypofluorite were passed into the solution over a period of 3 hours. The reaction mixture then was warmed to room temperature and evaporated to dryness under reduced pressure to give 7.60 g of crude 7-chloro-3-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one as a light tan powder: mp 130°-140° C.; 19F NMR (CCl3D) δ-161.7 ppm (d,J=57 Hz).

Workup

  1. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2445a71980a3476da449af51d24cc182
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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