N,N-Dimethylaniline → N-(2,4-dichloro-6-methylpyridin-3-yl)-2-bromoacetamide

3-Amino-2,4-dichloro-6-methylpyridine (48.0 g, 271.1 mmol) was dissolved in chloroform (384 mL), and N,N-dimethylaniline (39.4 g, 325.1 mmol) was added to the solution. A solution of bromoacetyl bromide (65.7 g, 325.5 mmol) in chloroform (96 mL) was added dropwise to the mixture under stirring and under cooling with ice. The resultant mixture was stirred for 1 hour at the same temperature and for 1 hour at room temperature. Subsequently, under cooling with ice, a solution of bromoacetyl bromide (27.4 g, 135.7 mmol) in chloroform (48 mL) was further added to the resultant mixture, followed by stirring for 1 hour at room temperature. Water (288 mL) was added to the reaction mixture, and the resultant mixture was stirred for 12 hours at room temperature. The reaction mixture was stirred for 2 hours under cooling with ice, and the precipitated crystals were collected through filtration. The crystals were washed with cold ethanol (96 mL) and dried at 50° C. by use of a blower, to thereby yield 58.81 g of N-(2,4-dichloro-6-methylpyridin-3-yl)-2-bromoacetamide (yield: 73%) as colorless crystals.

1. temperatureunder cooling with ice
2. temperatureSubsequently, under cooling with ice
3. stirringby stirring for 1 hour at room temperature
4. stirringThe reaction mixture was stirred for 2 hours
5. temperatureunder cooling with ice
6. filtrationthe precipitated crystals were collected through filtration
7. washThe crystals were washed with cold ethanol (96 mL)
8. customdried at 50° C. by use of a blower

ORD record

ord-7fa5d074498a4920b1fb2df5fc8d9078

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560547B2