Methane → HCID 22447446, compound

Temperature

80 °C

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 is warmed 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 filtrate is fractionally distilled to give pure glycine methyl ester isocyanate in about 70% yield (b.p. 60° C., 13 mm Hg).

1. temperatureThe reaction mixture is then heated
2. temperatureat reflux for 21/2 hours
3. temperatureThe reaction mixture is then cooled
4. filtrationfiltered
5. concentrationconcentrated to dryness by rotary evaporator
6. dissolutionThe crude product is re-dissolved in 100 mL THF
7. additionthe pH of the solution is adjusted to 5.5-6.0 by addition of pyridine
8. filtrationThe product mixture is again filtered
9. distillationthe filtrate is fractionally distilled

ORD record

ord-7d5b7d97b18b4306b389d63a0028eb90

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04705864