Chloroform → N-[4-(4-pyridinyl)phenyl]-2-butenamide

A mixture containing 6.8 g. of 4-(4-pyridinyl)benzeneamine, 17.8 ml. of crotonic anhydride and 200 ml. of chloroform was stirred at room temperature for 2 hours and then under reflux for 16 hours. The suspension was filtered and the filtercake was suspended in water plus ammonium hydroxide solution and was refiltered to give 3.86 g. of light tan solid after air-drying on the funnel. The chloroform filtrate was concentrated in vacuo and the tan residue was suspended in a mixture of water and ammonium hydroxide and the mixture filtered to give more tan solid. The combined tan solids were taken up in dimethylformamide, the hot solution filtered and the filtrate concentrated to less than 300 ml. and then treated with a slight excess of methanesulfonic acid in ethanol. The resulting mixture was diluted with ether and the separated product was collected and dried in vacuo at 125° C. for 14 hours to yield 4.31 g. of N-[4-(4-pyridinyl)phenyl]-2-butenamide methanesulfonate, m.p. 247°-249° C.

1. additionA mixture containing 6.8 g
2. temperatureunder reflux for 16 hours
3. filtrationThe suspension was filtered
4. customto give 3.86 g
5. customof light tan solid after air-drying on the funnel
6. concentrationThe chloroform filtrate was concentrated in vacuo
7. additionthe tan residue was suspended in a mixture of water and ammonium hydroxide
8. filtrationthe mixture filtered
9. customto give more tan solid
10. filtrationthe hot solution filtered
11. concentrationthe filtrate concentrated to less than 300 ml
12. additionand then treated with a slight excess of methanesulfonic acid in ethanol
13. additionThe resulting mixture was diluted with ether
14. customthe separated product was collected
15. customdried in vacuo at 125° C. for 14 hours
16. customto yield 4.31 g

ORD record

ord-52efe3b405e9423abe39205f6c0af158

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04377585