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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 21, Number 9
BKCSDE 21(9)
September 20, 2000 

Ring Closure of N-(2-Hydroxyethyl) -N'-phenylthioureas: One-Pot Synthesis of 2-Phenylaminothiazolines
Taek Hyeon Kim,* Jung Ki Min, Gue-Jae Lee
The cyclization reaction of N-(2-hydroxyethyl)-N'-phenylthioureas 2 containingambident nucleophile was ex-amined in the combination of a variety ofbases and p-toluenesulfonyl chloride (TsCl).N-(2-Hydroxyeth-yl) thioureas 2 were readily obtained in high yields from the reaction of the corresponding 1,2-aminoalcohols with phenyl isothiocyanate, avoiding the need for O-protection.The use of a one-pot reaction (NaOH/TsCl) was found to be most effective in producing the requisite 2-phenylaminothiazolines (S-cyclization) 3 in the case ofthioureas 2a-2e derived from N-unsubstituted aminoalcohols,while in the thioureas 2f and 2g prepared from N-substituted aminoalcohols the combination of Et3N and TsCl led to the S-cyclization products.
919 - 922
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