N,N-Dimethylaniline → N-[2,4-dibromo-6-methylpyridin-3-yl]-2-bromoacetamide

3-Amino-2,4-dibromo-6-methylpyridine (1.16 g, 4.38 mmol) was dissolved in methylene chloride (10 mL). N,N-dimethylaniline (0.77 g, 6.35 mmol) was added to the solution and then a solution of bromoacetyl bromide (1.03 g, 5.12 mmol) in dichloromethane (2 mL) was added dropwise thereto over 5 minutes with stirring and cooling with ice. After completion of addition, the temperature of the mixture was elevated to room temperature and stirred for 12 hours. The resultant mixture was washed sequentially with water, an aqueous saturated sodium hydrogencarbonate solution, and saturated brine. Subsequently, the mixture was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The residue was crystallized from hexane-acetone, to thereby yield 1.44 g of N-[2,4-dibromo-6-methylpyridin-3-yl]-2-bromoacetamide as colorless crystals (yield 85.3%).

1. temperaturecooling with ice
2. additionAfter completion of addition
3. customwas elevated to room temperature
4. stirringstirred for 12 hours
5. washThe resultant mixture was washed sequentially with water
6. dry with materialSubsequently, the mixture was dried over sodium sulfate anhydrate
7. concentrationconcentrated under reduced pressure
8. customThe residue was crystallized from hexane-acetone

ORD record

ord-e10d395fd8334f6f9e4c64dd0960b3fe

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560547B2