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

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 drop-wise via addition funnel over 1 h at 0-5° C. The resulting turbid mixture was stirred 3h at 0° C. The mixture was then washed in succession with 1M 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. additionvia addition funnel over 1 h at 0-5° C
2. washThe mixture was then washed in succession with 1M HCl solution (3×75 mL), 5% NaHCO3 solution (3×100 mL), and water (100 mL)
3. dry with materialThe organic phase was dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated on a rotary evaporator to a yellow oil (12.66 g)
6. distillationVacuum distillation
7. distillationVigreaux column and a short path distillation apparatus

ORD record

ord-d8256880c118465b89f80368b1468674

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06492399B1