Chemistry of sulfonyl isocyanates and sulfonyl isothiocyanates. X. Possible routes to substituted imidazolidinethiones and hexahydropyrimidinethiones

4‐Toluenesulfonyl isocyanate (I) reacted with 2‐aminoethanol and 3‐amino‐l‐propanol to give 2:1 isocyanate/amino alcohol addition products. 1‐Amino‐2‐propanol and I gave 1:1 and 2:1 adducts while 2‐amino‐2‐methyl‐l‐propanol afforded only a 1:1 adduct. 4‐Toluenesulfonyl isothio‐cyanate (III) gave 1:1 adducts with 2‐aminoethanol, l‐amino‐2‐propanol and 3‐amino‐l‐propanol, the first two of which were cyclized by concentrated sulfuric acid to 1‐(4‐toluenesulfonyl)‐imidazoline‐2‐thiones and the third to 1‐(4‐toluenesulfonyl)hexahydropyrimidine‐2‐thione. A 1:2 adduct was obtained from III and 2‐amino‐2‐methyl‐l‐propanol. Amino acids reacted with I and with 4‐chlorobenzenesulfonyl isocyanate (II) to give N ‐(arylsulfonyl)‐ N 1 ‐(carboxylic acid)‐ureas. N ‐(4‐Toluenesulfonyl)‐ N 1 ‐(acetic acid)‐urea (XVI) was converted to the methyl ester (XIX) by concentrated sulfuric acid and methanol and to water‐soluble unrecoverable products by sulfuric acid alone. Glycine and III gave N ‐(4‐toluenesulfonyl)‐N 1 ‐(acetic acid)‐thiourea (XX) which was converted to the methyl ester (XXII) by concentrated sulfuric acid/methanol and to the cyclic 1‐(4‐toluenesulfonyl)imidazolin‐5‐one‐2‐thione (XXI) by sulfuric acid alone.