Hydrochloric Acid → HCID 12723322, compound

A vigorously stirred solution of 4.5 grams (0.027 mole) of 2-bromopropenoyl chloride (Step B product) in 150 ml of dried methylene chloride was cooled to 5°±5°. To this was added dropwise 4.0 grams (0.027 mole) of N,N-diethylaniline at such a rate that the reaction mixture temperature did not exceed 10°. Upon completion of addition, 2.5 grams (0.027 mole) of aniline was added dropwise while continuing to maintain the reaction mixture temperature below 10°. The reaction mixture was allowed to warm to ambient temperature where it was stirred for two hours. After dilution with 100 ml of aqueous 1N hydrochloric acid, the reaction mixture was poured into a separatory funnel. The organic layer was separated and extracted with 50 ml of aqueous 1N hydrochloric acid, then with 100 ml of an aqueous solution saturated with sodium bicarbonate. The organic layer was dried with magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to a residual solid. The solid was dissolved in methylene chloride and decolorized with silica gel. The mixture was filtered and the filtrate concentrated under reduced pressure to a residual solid. The solid was recrystallized from hexane to give 4.0 grams of 2-bromo-N-phenyl-2-propenamide; mp 90.5°-92.5°.

1. customdid not exceed 10°
2. additionwas added dropwise
3. temperatureto maintain the reaction mixture temperature below 10°
4. customThe organic layer was separated
5. extractionextracted with 50 ml of aqueous 1N hydrochloric acid
6. dry with materialThe organic layer was dried with magnesium sulfate
7. filtrationThe mixture was filtered
8. concentrationthe filtrate concentrated under reduced pressure to a residual solid
9. dissolutionThe solid was dissolved in methylene chloride
10. filtrationThe mixture was filtered
11. concentrationthe filtrate concentrated under reduced pressure to a residual solid
12. customThe solid was recrystallized from hexane

ORD record

ord-487d02a6e6664130a6d2a3d2b8331585

Source dataset

uspto-grants-1987_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USH0000327