Reaction #1135816

Reaction equation

dimethyl sulfate

1-(2-methyl-3-ethoxyphenyl)-1,4-dihydrotetrazole-5-one

potassium carbonate

N,N-dimethylformamide

→

1-(2-methyl-3-ethoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one

Yield 92.1%

Solvents

water

Conditions

Workup

1. 1
   Extractionthe mixtures were extracted with ethyl acetate
2. 2
   Washthe organic layers were washed with water and saturated saline
3. 3
   Dryingwere dried over anhydrous magnesium sulfate
4. 4
   Concentrationwere then concentrated under reduced pressure

Procedure

Under ice-cooling, to a mixture of 1-(2-methyl-3-ethoxyphenyl)-1,4-dihydrotetrazole-5-one 39.0 g, potassium carbonate 36.7 g and N,N-dimethylformamide 400 mL was added dimethyl sulfate 44.7 g and the resulting mixtures were raised to room temperature and were stirred for seven hours. Thereto was added water and the mixtures were extracted with ethyl acetate and the organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give 1-(2-methyl-3-ethoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 38.2 g.

Source