Reaction #1135790

Reaction equation

sodium nitrite

hydrochloric acid

aluminum chloride

sodium azide

1-isocyanato-2-methylbenzene

→

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

Yield 104.3%

Solvents

water

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting mixtures were stirred for fifteen minutes
2. 2
   workup.ADDITIONwas added the reaction solutions
3. 3
   workup.STIRRINGwith stirring
4. 4
   Extractionwere extracted with ethyl acetate
5. 5
   WashThe organic layers were washed with water and saturated saline
6. 6
   Dryingwere dried over anhydrous magnesium sulfate
7. 7
   Concentrationwere then concentrated under reduced pressure

Procedure

Under ice-cooling, to N,N-dimethylformamide 500 mL was added anhydrous aluminum chloride 55.1 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 26.9 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-isocyanato-2-methylbenzene 50.6 g and the resulting mixtures were heated at 70° C. for four hours. After cooling, to a mixture of sodium nitrite 51.8 g, water 2 L and ice 500 g was added the reaction solutions with stirring. The mixtures were acidified with 10% hydrochloric acid and were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure to give 1-(2-methylphenyl)-1,4-dihydrotetrazole-5-one 69.8 g.

Source