Reaction #640582

Reaction equation

water

5,5-dimethyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-thione

sodium hydrogen carbonate

methyl chloroformate

→

5,5-dimethyl-3-(2-[N-(methoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinane-2-thione

Yield 46.6%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for three hours
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe solvent was evaporated under reduced pressure after the organic layer
5. 5
   Dryingwas dried over anhydrous sodium sulfate
6. 6
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:l)

Procedure

5,5-dimethyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-thione (0.15 g, 0.39 mmol) and sodium hydrogen carbonate (0.05 g, 0.60 mmol) were suspended in acetonitrile (10 ml), added with methyl chloroformate (0.06 g, 0.60 mmol) and heated to reflux for three hours. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The solvent was evaporated under reduced pressure after the organic layer was dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:l) to obtain 5,5-dimethyl-3-(2-[N-(methoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinane-2-thione (0.08 g).

Source