YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
スルホニル尿素関連化合物の研究 (第4報)
1-Arylsulfonyl-3-(2-bromoethyl) ureaの閉環について
安藤 憲章
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ジャーナル フリー

1962 年 82 巻 11 号 p. 1542-1546

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1-Arylsulfonyl-3-(2-bromoethyl)urea (III) was, in the presence of base, cyclized very easily to 2-arylsulfonamido-2-oxazoline (IV) and 1-arylsulfonyl-2-imidazolidinone (V), simultaneously. The ratio of the production, IV/V, decreased in the following order of water and alkaline solution, and (V) was dominantly produced in either dehydrated pyridine or NaOEt (in dehydrated EtOH), (IV) being scarcely produced.
(V) is also obtainable by reacting 2-imidazolidinone with arylsulfonyl chloride in pyridine. (V) was easily hydrolyzed to arylsulfonylethylenediamine when it was kept standing at room temperature in strong alkali.
A part of (IV) was converted to (V) by fusion. (III) was prepared from arylsulfonylurea and 2-bromoethylamine⋅HBr easily, and its cyclization mechanism is also reported.

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