Butylamine → HCID 14329784, compound

(E,E)-4-Ethyl-2,4-hexadienoic acid (5 g) was dissolved in tetrahydrofuran (300 ml) and triethylamine (5 ml) was added to the solution. The mixture was stirred at room temperature for 30 minutes and then ethyl chloroformate (3.4 ml) was added dropwise thereto at -20° C. with stirring. The resulting mixture was stirred at the same temperature for 60 minutes. n-Butylamine (3.6 ml) was added to the reaction mixture at -20° C. The resulting mixture was stirred at the same temperature for 60 minutes. The reaction mixture was concentrated and the concentrate was diluted with water, and then extracted with two portions of ethyl acetate (100 ml×2). The combined extracts were washed with successively an aqueous sodium carbonate solution and brine, dried over magnesium sulfate and then evaporated to dryness to given an oil (6.5 g) which was subjected to column chromatography on silicagel, eluting with chloroform containing 2% methanol, to give (E,E)-N-n-butyl-4-ethyl-2,4-hexadienamide (5.8 g).

1. stirringat -20° C. with stirring
2. stirringThe resulting mixture was stirred at the same temperature for 60 minutes
3. stirringThe resulting mixture was stirred at the same temperature for 60 minutes
4. concentrationThe reaction mixture was concentrated
5. additionthe concentrate was diluted with water
6. extractionextracted with two portions of ethyl acetate (100 ml×2)
7. washThe combined extracts were washed with successively an aqueous sodium carbonate solution and brine
8. dry with materialdried over magnesium sulfate
9. customevaporated to dryness
10. washeluting with chloroform containing 2% methanol

ORD record

ord-40b253fdc12f4361a38d76212e390c00

Source dataset

uspto-grants-1988_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04767768