Sodium hydride (0.6 g, 57% mineral oil), washed free of mineral oil with hexane under a nitrogen atmosphere, is slurried in 25 ml of anhydrous tetrahydrofuran and cooled to 0°. A solution of 2-chloro-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-benzenamine (4.3 g, 0.010 mole) in 25 ml of anhydrous tetrahydrofuran is then added dropwise with stirring at 0°. When the addition is complete, the solution is allowed to warm to ambient temperature and stirred for one hour. Perchloromethyl mercaptan (1.9 g, 0.010 mole) is then added and stirring is continued for two hours. The reaction mixture is then poured into water, extracted with methylene chloride, dried over anhydrous magnesium sulfate and stripped under vacuum to afford an orange resin. Chromatography on silica gel utilizing 1-chlorobutane/hexane (1:1 by vol) as the eluent affords 3.5 g of 1,1,1-trichloro-N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]methanesulfenamide as a yellow oil which crystallizes on standing, m.p. 134°-137°.
