Benzoyl chloride → N-Methyl-N-(3-buten-1-yl)benzamide

Temperatur

0 °C

Under a nitrogen atmosphere, a solution of N-methyl-3-buten-1-amine (6.86 g, 80.6 mmol) in dichloromethane (100 mL) was cooled to 0° C., and triethylamine (17.93 g, 177.2 mmol) and 4-(N,N-dimethylamino)pyridine (207 mg) were added. A solution of benzoyl chloride (11.89 g, 84.6 mmol) in dichloromethane (60 mL) was added dropwise via addition funnel over 1 h at 0-5° C. The resulting turbid mixture was stirred 3 h at 0° C. The mixture was then washed in succession with 1 M HCl solution (3×75 mL), 5% NaHCO3 solution (3×100 mL), and water (100 mL). The organic phase was dried (Na2SO4), filtered, and concentrated on a rotary evaporator to a yellow oil (12.66 g). Vacuum distillation using a 6 in. Vigreaux column and a short path distillation apparatus afforded 8.58 g (56.3%) of a colorless oil, bp 100-103° C. at 0.1 mm Hg.

1. washThe mixture was then washed in succession with 1 M HCl solution (3×75 mL), 5% NaHCO3 solution (3×100 mL), and water (100 mL)
2. dry with materialThe organic phase was dried (Na2SO4)
3. filtrationfiltered
4. concentrationconcentrated on a rotary evaporator to a yellow oil (12.66 g)
5. distillationVacuum distillation
6. distillationVigreaux column and a short path distillation apparatus

ORD-Eintrag

ord-38aca0e850d34625a06d8bb6cae66180

Quelldatensatz

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06310102B1