Thionyl Chloride → 2-Chloronicotinoyl chloride

1.891 g (12.0 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride and two droplets of DMF were heated under reflux for 2 hours. The reaction mixture was allowed to cool, and then concentrated under reduced pressure. 2-Chloronicotinoyl chloride thus obtained was then dissolved in 10 ml of acetone. 770 mg of ammonium thiocyanate was it then dissolved in 15 ml of acetone with stirring. To the solution thus obtained was then added dropwise the acetone solution of 2-chloronicotinoyl chloride in 5 minutes. The mixture was then stirred. The mixture was then stirred over a 40° C. oil bath for 5 minutes. The insoluble matters thus precipitated were then removed by filtration to obtain an acetone solution of 2-chloronicotinoyl isothiocyanate. To the solution thus obtained was then added dropwise a mixture of 2.151 g of N-ethyl-3,4-ethylenedioxyaniline and 10 ml of acetone with stirring at room temperature in 5 minutes. The reaction mixture was stirred at room temperature for 16 hours, and then poured into about 1,000 ml of ice-water. The resulting crystal was collected by filtration, washed with water, and then dried under reduced pressure. The resulting product was then recrystallized from ethanol to obtain 2.18 g of 2-[N-(2,3-dihydro-1,4-benzodioxan-6-yl]-N-ethylamino-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

1. temperatureunder reflux for 2 hours
2. temperatureto cool
3. concentrationconcentrated under reduced pressure

ORD record

ord-2f728472ee574234b8bafca73f4d6136

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133258