Abstract
This method of synthesis appears to be the more desirable because of the ease of purification of the product. 1-Naphthalenethiol(3) was converted to 2-(1-naphthylthio)ethyl acetate(5) via 2-(1-naphthylthio)ethanol(4) in an overall yield of 75%. Sulfonation of the ester 5 was carried out using 1 equiv of chlorosulfonic acid in dry chloroform to produce the 4-(2-acetoxyethylthio)-1-naphthalenesulfonic acid(6) which was isolated as the sodium salt(7) in 68% yield. The acetoxy acid chloride (8) was prepared from 7 in 68% yield. The reaction of 8 with excess ammonia in acetonitrile afforded an 89% yield of the desired sulfonamide(9), which was readily oxidized with m-chloroperoxybenzoic acid to the sulfone(10) in 84% yield. Hydrolysis of 10 with dilute hydrochloric acid in aqueous ethanol at 60/sup 0/C readily afforded pure HO--ENS in 95% yield. The compound was subjected to /sup 13/C NMR studies and thin-layer chromatographic analysis. 2 figures.
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