Methane → HCID 22447446, compound

Participants

Reaction Steps

38.8 mL diphosgene is added dropwise over 1 hour to a mixture of 35 g glycine methyl ester hydrochloride and 0.4 g activated charcoal In 400 ml dioxane under N2. The reaction mixture warms to 80° C. during this time. The reaction mixture is then heated and stirred at reflux for 21/2 hours. The reaction mixture is then cooled, filtered, and concentrated to dryness by rotary evaporator, keeping exposure to moisture to a minimum. The crude product is re-dissolved in 100 mL THF, and the pH of the solution is adjusted to 5.5-6.0 by addition of pyridine. The product mixture is again filtered, and the product is purified by fractional distillation to give pure glycine methyl ester isocyanate in ~70% yield (bp 60° C., 13 mm Hg).

Provenance & Evidence