Sodium → Methyl N-hydroxyethanimidothioate

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A solution of 0.8 g of N-hydroxy-ethanimidothioic acid, methyl ester in 5 ml methanol and 10 toluene was prepared, 0.4 g of sodium methoxide was added in one portion, and the mixture was stirred until dissolution was complete. The solution of the sodium salt of N-hydroxy-ethanimidothioic acid was added dropwise at 0° C. to a solution of 3.0 L g of 2-(dimethylamino)-N-[[[N-[[2-[N-(fluorocarbonyl)-N-methylaminothio]ethylthio]]-N-methylaminocarbonyloxy]]]-2-oxoethanimidothioic acid, methyl ester in 100 ml toluene. The resulting turbid reaction mixture was allowed to warm to ambient temperature and stirred 18 hrs. The reaction mixture was washed with two 100 ml portions of water, 100 ml of saturated sodium chloride solution, and dried over magnesium sulfate. Distillation of the solvent under reduced pressure gave a pale yellow viscous oil. The title compound was isolated from the crude reaction product by chromatography on silica gel employing ethyl acetate to elute the product. Using this procedure there was obtained 1.4 g of an oil that partially solidified. Suspension of the oily solid in a mixture of ether and hexanes gave 1.3 g of substantially pure 2-(dimethylamino)-N-[[[[N-methyl-N-[[[2-[[-N-methyl-N-[(1-methylthioethylidene)aminooxycarbonyl]aminothio]]ethylthio]]]aminocarbonyloxy]]]]-2-oxoethanimidothioic acid, methyl ester, m.p. 102°-106° C.

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