Triethylamine → N-(2-Nitrooxyethyl)-5,5-dimethyl-2-oxothiazolidine-4-carboxamide

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Reaction Steps

1.38 ml of triethylamine and 0.37 ml of diethyl cyanophosphonate were added, whilst ice-cooling and stirring, to a suspension of 360 mg of 5,5-dimethyl-2-oxothiazolidine-4-carboxylic acid and 417 mg of N-(2-nitrooxyethyl)amine nitrate in 50 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 4 hours, after which the solvent was removed by distillation under reduced pressure. The residue was mixed with ethyl acetate, and the resulting mixture was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residual pale yellow oil was purified by column chromatography through silica gel, using a 50:1 by volume mixture of methylene chloride and methanol as the eluent. The crystals thus obtained were recrystallized from diethyl ether, to give 180 mg of the title compound as colorless crystals, melting at 98°-100° C.

Provenance & Evidence