Reaction #1135794

Reaction equation

aluminum chloride

1-chloro-3-isocyanato-2-methylbenzene

sodium nitrite

hydrochloric acid

sodium azide

→

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

Yield 54.1%

Solvents

N,N-dimethylformamide

water

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting mixtures were stirred for fifteen minutes
2. 2
   TemperatureAfter cooling the mixtures
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 250 mL was added anhydrous aluminum chloride 21.9 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 10.7 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-chloro-3-isocyanato-2-methylbenzene 25.0 g and the resulting mixtures were heated at 80° C. for five hours. After cooling the mixtures, to a mixture of sodium nitrite 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-methyl-3-chlorophenyl)-1,4-dihydrotetrazole-5-one 17.0 g.

Source