Dimethylamine → Cyclohexanamine, N-cyclohexyl-N-[[(dimethylamino)thioxomethyl]thio]-

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Reaction Conditions

Reaction Steps

N,N-dimethylthiocarbamyl-N',N'-dicyclohexylsulfenamide was prepared. 100 milliliters of carbon tetrachloride, 39.6 grams of a solution of dimethylamine at 25% by weight in water (0.22 mole) and 36.2 grams (0.2 mole) of dicyclohexylamine were placed in a reactor vessel and the mixture cooled to 10° C. 114 milliliters of a solution of NaOCl at 14% by weight in water (0.23 mole) was added and the mixture stirred for 15 minutes at 10° to 15° C. 200 milliliters of water containing 25 grams of NaHCO3 and 11 grams of Na2CO3 was then added as a buffer solution. The mixture was warmed to 20° C. and 15.2 grams (0.2 mole) of carbon disulfide was added while stirring. The mix was stirred for 40 minutes at a temperature of about 32°-35° C. The mixture was allowed to settle and the non-aqueous phase separated out and filtered. The carbon tetrachloride was then evaporated off, leaving 61 grams of a thick liquid. 150 milliliters of methanol was added and the liquid first dissolved, then a solid precipitated out. The methanol slurry was cooled to -10° C. and filtered. The solids isolated were dried, and 44.1 grams of a white crystalline solid having a melting point of 85°-87° C. was obtained. The yield was 77% by weight based upon the weight of carbon disulfide used. The N,N-dimethylthiocarbamyl-N',N'-dicyclohexylsulfenamide was identified by its Infra-red spectrum. The calculated element weights for the formula C15H28N2S2 were 9.32% nitrogen, 60.0% carbon, and 9.32% hydrogen. Analytical values were 9.34% nitrogen, 59.8% carbon, and 9.60% hydrogen respectively.

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