Reaction #1135791

Reaction equation

methyl iodide

1-(2-methylphenyl)-1,4-dihydrotetrazole-5-one

N,N-dimethylformamide

sodium hydride

→

1-(2-methylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one

Solvents

water

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   workup.STIRRINGwere stirred for two and a half hours
3. 3
   OtherTo the reaction mixtures
4. 4
   Extractionthe mixtures were extracted with methyl tert-butyl ether
5. 5
   WashThe organic layers were washed with 10% hydrochloric acid, water and saturated saline
6. 6
   Dryingwere dried over anhydrous magnesium sulfate
7. 7
   Concentrationwere then concentrated under reduced pressure

Procedure

To a mixture of the above-mentioned 1-(2-methylphenyl)-1,4-dihydrotetrazole-5-one 69.8 g and N,N-dimethylformamide 380 mL was added 55% sodium hydride 18.2 g under ice-cooling. After stirring the resulting mixture for twenty minutes, thereto was added methyl iodide 59.4 g. The mixtures were raised to room temperature and were stirred for two and a half hours. To the reaction mixtures was added water and the mixtures were extracted with methyl tert-butyl ether. The organic layers were washed with 10% hydrochloric acid, 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-methylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 52.5 g.

Source