반응 #1161329

반응 방정식

2,6-dimethylaniline

ethyl chloroformate

6-chloronicotinic acid

triethylamine

→

solid

수율 73.7%

6-Chloro-N-(2,6-dimethylphenyl)-3-pyridinecarboxamide

수율 73.7%

용매

water

acetone

acetone

acetone

반응 조건

후처리

1. 1
   온도to maintain the temperature below 0° C
2. 2
   온도while maintaining the temperature below 0° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   온도to warm to room temperature overnight
5. 5
   추출extracted into ethyl acetate
6. 6
   세척The organic layer was washed with water, dilute hydrochloric acid, water
7. 7
   건조The organic solution was dried over sodium sulfate
8. 8
   농축concentrated in vacuo

실험 절차

A slurry of 25 g of 6-chloronicotinic acid in approximately 300 ml of acetone was treated with 22.6 ml of triethylamine. The reaction mixture was cooled to approximately -10° C. by means of an external ice/methanol bath. A solution of 15.5 ml of ethyl chloroformate in acetone was added to the mixture at a rate to maintain the temperature below 0° C. After stirring with the cold bath for 2 hours, a solution of 38.5 g of 2,6-dimethylaniline in approximately 150 ml of acetone was added while maintaining the temperature below 0° C. After the addition was complete, the mixture was allowed to warm to room temperature overnight. The mixture was poured into water and extracted into ethyl acetate. The organic layer was washed with water, dilute hydrochloric acid, water, a dilute sodium bicarbonate solution, water (twice), and a saturated sodium chloride solution. The organic solution was dried over sodium sulfate and concentrated in vacuo to provide 30.5 g of a solid. Crystallization from methanol/water provided 14.6 g of the desired title product, m.p. 165°-166° C.

출처