N. Akhtar, N. Badami, R. Cremlyn
Sep 1, 1977
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Journal
Phosphorus Sulfur and Silicon and The Related Elements
Abstract
Abstract o-Methoxyphenyl-, N-phenyl-N′,N′-dimethyl, and N-3-acetylphenyl-urea with chlorosulfonic acid gave 4-methoxy-3-ureido, 4-(N′,N′-dimethylureido)-, and N-3-acetylureido-benzenesulfonyl chlorides respectively. However, attempts to chlorosulfonate phenylthiourea were unsuccessful; the product was the zwitterionic sulfonic acid which did not give the sulfonyl chloride with phosphorus pentachloride. N-Phenyl-N′-p-tolyl urea by reaction with chlorosulfonic acid afforded the corresponding 4-sulfonyl chloride. N-Phenyl-N′-2-pyridyl- and N-phenyl-N′-2-thiazolyl thioureas reacted similarly. In contrast, N-phenyl-N′-2′-pyridylurea only gave the bis-sulfonyl chloride. Selected ureido-sulfonyl chlorides have been condensed with hydrazine and sodium azide and some reactions of the sulfonyl azides examined. Acetylation of phenylurea gave only the N-(3-acetyl)- or the S-acetyl derivative depending on the conditions. Contrary to previous work, it is not considered that the N-(l-acetyl) phenylthiourea is formed.