Reaktion #586466

Reaktionsgleichung

water

N,N-Dimethylthiocarbamoyl chloride

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

Methyl 4-methylsalicylate

DMF

→

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

Ausbeute 55.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 20 hrs
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe extract was washed with water
4. 4
   Sonstigedried
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   Wascheneluted with hexane-ethyl acetate (3:1
7. 7
   Sonstigev/v), recrystallized from ethyl acetate-hexane

Vorschrift

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.).

Quelle