1-Chloroethyl chloroformate → HCID 54399635, compound

Temperature

0 °C

α-(Methoxyimino)-α-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)acetonitrile (D7) (0. 047 g, 0.00026 moles) was dissolved in dry dichloromethane (1 ml) and cooled to 0° C. under a nitrogen atmosphere. α-Chloroethyl chloroformate (0.041 g, 0.00029 moles) was added with stirring and the mixture allowed to warm to room temperature. The mixture was stirred for a further 4 h and then evaporated to dryness. Methanol (5 ml) was added and the mixture was heated under reflux for 1 h. Evaporation of the solvent gave an oil which was partitioned between saturated aqueous potassium carbonate and chloroform. The organic phase was separated and dried (Na2SO4) then evaporated to dryness. Column chromatography on silica-gel eluting with 0-2% methanol/chloroform gave the title compound (D8) as a crystallising oil (0.03 g, 69%). Treatment with anhydrous oxalic acid afforded a white crystalline solid m.p. 180°-190° C.

1. temperatureto warm to room temperature
2. stirringThe mixture was stirred for a further 4 h
3. customevaporated to dryness
4. additionMethanol (5 ml) was added
5. temperaturethe mixture was heated
6. temperatureunder reflux for 1 h
7. customEvaporation of the solvent
8. customgave an oil which
9. customwas partitioned between saturated aqueous potassium carbonate and chloroform
10. customThe organic phase was separated
11. dry with materialdried (Na2SO4)
12. customthen evaporated to dryness
13. washColumn chromatography on silica-gel eluting with 0-2% methanol/chloroform

ORD record

ord-726396f7d227437d97892882fdf88eea

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05356914