Ammonium thiocyanate → 1-Methyl-1-(1-isothiocyanato-2,2,2-trichloroethyl)-3-(3,4-dichlorophenyl)urea

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Reaction Steps

1-methyl-1-(1,2,2,2-tetrachloroethyl)-3-(3,4-dichlorophenyl)urea (7.7 g, 0.02 mol) was dissolved in 200 ml dimethoxyethane, followed by addition of 1.5 g (0.02 mol) of ammonium thiocyanate. The mixture was stirred for 2 hours, filtered and stripped of solvent. Ether was added to the residue, which was again filtered to remove a small amount of solid. The remaining solvent was then removed, leaving a dark oil which solidified upon standing. This material had a melting point of 142°-146° C. The infrared spectrum of the material showed a broad absorption band at 4.9 micron (for the --N=C=S group). Elemental analysis showed: %Cl, calc., 43.6, found 36.7; %S, calc. 7.9, found 6.3.

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