Hydrochloric Acid → 3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile

Sodium hydride (60% dispersion in mineral oil, 0.6 g, 15 mmol) was charged and washed with hexane twice. Into this flask, 1,3-dimethyl-2-imidazolydinone (20 ml) was added and a solution prepared by dissolving 4-amino-1,1,1-trifluoro-3-buten-2-one (2.1 g, 15 mmol) and 3-methoxyacrylonitrile (1.2 g, 15 mmol) in 1,3-dimethyl-2-imidazolydinone (5 ml) was added dropwise under ice-cooling. After stirring the mixture at room temperature for 3 hours, the reaction mixture was poured into water (200 ml). This mixture was acidified with concentrated hydrochloric acid under ice-cooling and then extracted with ethyl acetate. The obtained organic layers were washed with saturated brine, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (a eluting solvent: hexane/ethyl acetate=3/1 to 2/1) to obtain 2.60 g (yield 92.0%) of a mixture of title compounds (IIa) and (IIb).

1. washwashed with hexane twice
2. additionInto this flask, 1,3-dimethyl-2-imidazolydinone (20 ml) was added
3. customa solution prepared
4. additionwas added dropwise under ice-
5. temperaturecooling
6. temperaturecooling
7. extractionextracted with ethyl acetate
8. washThe obtained organic layers were washed with saturated brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue was purified by silica gel column chromatography (a eluting solvent

ORD record

ord-cca0103f3cab4ce08f48a04afb8f56c4

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07015236B2