Thionyl Chloride → 2-Chloronicotinoyl chloride

1.757 g (11.2 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride and two droplets of DMF were heated under reflux for 2 hours. The resulting reaction solution was allowed to cool, and then concentrated under reduced pressure. 2-chloronicotinoyl chloride thus obtained was dissolved in 10 ml of acetone, and then packed into a dropping funnel. 891 mg of ammonium thiocyanate was then dissolved in 15 ml of acetone. The aforementioned acetone solution of acid chloride was then added dropwise to the ammonium thiocyanate solution with stirring in 5 minutes. The reaction solution was then heated to a temperature of 40° C. for 5 minutes. The resulting insoluble matters were then removed by filtration. To the acetone solution of 2-chloronicotinoyl isothiocyanate was then added dropwise a mixture of 1.66 g of 4-chloro-N-methylaniline and 10 ml of acetone with stirring in 5 minutes. After the termination of dropwise addition, the reaction mixture was further stirred for 15 hours. The resulting reaction mixture was poured into an about 1,000 ml of ice-water. The compound thus precipitated was collected by filtration, washed with water, and then dried under reduced pressure. The resulting crude product was then recrystallized from ethanol to obtain 2.95 g of 2-[N-(4-chlorophenyl)-N-methylamino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

1. temperatureunder reflux for 2 hours
2. customThe resulting reaction solution
3. temperatureto cool
4. concentrationconcentrated under reduced pressure

ORD record

ord-03e16e31b9bd480a8802d4f9927eec64

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133258