• Archives of Pharmacal Research
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• v.17 no.4
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• pp.281-283
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• 1994

5-sec-butylthiomethyl-5-alkyl (methyl or phenyl) hydantoins (3-x) were prepared by the reaction of sec-buylthiomethyl alkyl (methyl or phenyl) ketone (1-2), potassium cyanide and ammonium carbonate. 3-(2-Bromoethyl) hydantoins (5-6) were the reaction products of 5-sec-buythiomethyl-5-alkyl (methyl or phenyl) hydantoin and 1, 2-dibromothane in the presence of potassium hydroxide. Alkylation of 5 and 6 with an excess of alkyl (methyl or ethyl iodide in THF with sodium hydride as base gave three 1-alkyl (methyl or ethyl)-3-(2-bromoethyl) hydantoins (7-9). Treatment of the 2-bromothyl group with potassium thioacelate and triethylamine gave three 1-alkyl (methyl or ethyl)-3-92-acetylthioethyl) hydantoins (10-12). Hydrolysis of the 2-acetylthiuoethyl group with sodium hydroxide in methanol afforded the three 1-alkyl (methyl or ethyl)-3-(2-mercaptorthyl) hydantoins.