Triethylamine → N-methyl-N-[4-(tert-butyl)phenylthio]carbamoyl fluoride

Participants

Reaction Conditions

Reaction Steps

To 1200 L ml of toluene at (-40°)-(20° C) in a one-gallon polypropylene bottle containing a stirrer, was added with stirring 37.4 grams (1.87 moles) of liquid hydrogen fluoride. The reaction mixture was raised to -10° C and 107 grams (1.87 moles) of methyl isocyanate was added with stirring and cooling. The reaction mixture was stirred for 1 hour at 0° C after the methyl isocyanate addition. To this mixture was then added 375 grams (1.87 moles) of 4-(tert-butyl) phenylsulfenyl chloride at 0° C over a 2 minute period. After the 4-(tert-butyl) phenylsulfenyl chloride addition, 189 grams (1.87 moles) of triethylamine was added slowly, with cooling and stirring. The reaction mixture was then warmed to 25° C and stirred overnight when it was added to 1000 ml of water. The toluene layer was washed four times with water and dried with magnesium sulfate after which it was distilled through a 1-foot packed column to give 275 grams of N-methyl-N-[4-(tert-butyl)phenylthio]carbamoyl fluoride, b.p. 122°/1.0 mm (yield 61%). The nmr spectrum agreed with the proposed structure.

Provenance & Evidence