Triethylamine → Cyanomethylcarbamic acid allyl ester

Temperature

20 °C

To a suspension of 110 g of aminoacetonitrile hydrochloride in 1.2 l of acetonitrile were added at 20° C. 121.5 g of triethylamine. The mixture was cooled in an acetone-ice bath and 144.7 g of allyl chloroformate were added slowly, the temperature being maintained below 20° C. Subsequently, 121.5 g of triethylamine were added at such a rate that the temperature did not rise above 20° C. The mixture was stirred at 20° C. for 2 h and then, the solids were removed by filtration. The mother liquor was concentrated in vacuo and the oily residue was partitioned between ethyl acetate and water. The organic layer was washed successively with saturated potassium hydrogen sulfate solution, saturated potassium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The residual oil was distilled in vacuo to yield 132.6 g of cyanomethylcarbamic acid allyl ester as a colorless oil, b.p. 100° C./0.07 mbar.

1. additionwere added at 20° C
2. temperatureThe mixture was cooled in an acetone-ice bath
3. temperaturethe temperature being maintained below 20° C
4. customdid not rise above 20° C
5. customthe solids were removed by filtration
6. concentrationThe mother liquor was concentrated in vacuo
7. customthe oily residue was partitioned between ethyl acetate and water
8. washThe organic layer was washed successively with saturated potassium hydrogen sulfate solution, saturated potassium hydrogen carbonate solution and brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated in vacuo
11. distillationThe residual oil was distilled in vacuo

ORD record

ord-61a8c25045174218bb54d5481b07aedc

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05594135