Hydrochloric Acid → HCID 19815176, compound

Participants

Reaction Conditions

Reaction Steps

Meclomen (5.92 g; 0.02 mol) is suspended in CH2Cl2 (150 ml) containing DMF (1.46 g, 0.02 mol) and cooled to 0° C. Oxalyl chloride is added to the solution over 30 minutes and the resulting yellow solution is stirred at 24° C. for 20 hours and then added to a cold solution of N-benzylhydroxylamine (2.46 g; 0.02 mol) in THF (60 ml)--H2O (15 ml)--Et3N (20 ml) mixture. The solution is allowed to come to 24° C. and treated with 2N HCl (160 ml). The product is extracted with CH2Cl2. The extracts are dried over sodium sulfate and evaporated to dryness. The residue is flash chromatographed through SiO2 gel eluting with CH2Cl2. The fractions containing the product are evaporated and the solid residue is recrystallized from isopropylether/n-hexane yielding white crystals. Yield 1.45 g (18.6%); mp 133°-135° C.

Provenance & Evidence