7-Chloro-1,3-dihydro-1-methyl-3-hydroxy-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one → HCID 13125990, compound

Participants

Reaction Steps

A solution of 1.4 g of 3-hydroxy-1,3-dihydro-1-methyl-7-chloro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one in 10 ml of methylene chloride was added dropwise to a stirred solution of 1.5 ml of diethylaminosulfur trifluoride in 50 ml methylene chloride cooled to -70°. The reaction mixture was allowed to warm slowly to 5° and then poured into 100 ml of ice water. The lower organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The residue was recrystallized from heptane to give 1.17 g of 3-fluoro-1,3-dihydro-1-methyl-7-chloro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one as cream-colored crystals: mp 91°-95°; 1H nmr (CCl3D) δ 3.51 ppm (s, 3H), 5.66 ppm (d, J=57 Hz, 1H) and 7.5 ppm (m, 7H).

Provenance & Evidence