Reacción #835288

Ecuación de reacción

water

N,N-Dimethylthiocarbamoyl chloride

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

Methyl 4-methylsalicylate

DMF

→

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

Rendimiento 55.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 20 hrs
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe extract was washed with water
4. 4
   Otrodried
5. 5
   Otrothe solvent was evaporated under reduced pressure
6. 6
   Lavadoeluted with hexane-ethyl acetate (3:1
7. 7
   Otrov/v), recrystallized from ethyl acetate-hexane

Procedimiento

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.).

Fuente