반응 #835288

반응 방정식

water

N,N-Dimethylthiocarbamoyl chloride

1,4-diazabicyclo[2,2,2]octane

Methyl 4-methylsalicylate

DMF

→

methyl 2-(N,N-dimethylaminothiocarbamoyl)oxy-4-methylbenzoate

수율 55.0%

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 20 hrs
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The extract was washed with water
4. 4
   기타dried
5. 5
   기타the solvent was evaporated under reduced pressure
6. 6
   세척eluted with hexane-ethyl acetate (3:1
7. 7
   기타v/v), recrystallized from ethyl acetate-hexane

실험 절차

Methyl 4-methylsalicylate (10.7 g, 64 mmol) was dissolved in DMF (100 ml). N,N-Dimethylthiocarbamoyl chloride (8.0 g, 65 mmol) and 1,4-diazabicyclo[2,2,2]octane (7.2 g, 65 mmol) were added thereto with the mixture stirring. The reaction mixture was stirred at room temperature for 20 hrs, poured into water and extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (3:1, v/v), recrystallized from ethyl acetate-hexane to give methyl 2-(N,N-dimethylaminothiocarbamoyl)oxy-4-methylbenzoate (9.1 g, 55%) as crystals (mp. 99.9-100.2° C.).

출처