Reaction #1135802

Reaction equation

methyl iodide

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

N,N-dimethylformamide

sodium hydride

→

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

Solvents

water

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   OtherTo the reaction mixtures
3. 3
   Temperaturecooling
4. 4
   TemperatureThe mixtures were raised to room temperature
5. 5
   workup.STIRRINGwere stirred for fourteen hours
6. 6
   OtherTo the reaction mixtures
7. 7
   Extractionthe mixtures were extracted with ethyl acetate
8. 8
   WashThe organic layers were washed with 10% hydrochloric acid, water and saturated saline
9. 9
   Dryingwere dried over anhydrous magnesium sulfate
10. 10
    Concentrationwere then concentrated under reduced pressure

Procedure

To a mixture of the above-mentioned 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazole-5-one 31.40 g and N,N-dimethylformamide 250 mL was added 60% sodium hydride 5.90 g under ice-cooling. The mixtures were raised to room temperature and were stirred for one hour. To the reaction mixtures was added methyl iodide 8.4 mL under ice-cooling. The mixtures were raised to room temperature and were stirred for fourteen hours. To the reaction mixtures was added water and the mixtures were extracted with ethyl acetate. 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-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Intermediate (PRB-P)”) 8.47 g.

Source