Reaction #1135799

Reaction equation

1-chloro-3-isocyanato-2-methylbenzene

aluminium chloride

sodium azide

hydrochloric acid

sodium nitrite

→

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

Solvents

tetrahydrofuran

tetrahydrofuran

water

Conditions

Workup

1. 1
   Temperaturewith heating
2. 2
   Temperatureunder reflux for one hour
3. 3
   OtherAfter the reaction mixtures
4. 4
   Temperaturewere cooled under ice-
5. 5
   Temperaturecooling
6. 6
   workup.ADDITIONwere added
7. 7
   workup.STIRRINGthe resulting mixtures were stirred
8. 8
   Temperaturewith heating
9. 9
   Temperatureunder reflux for five hours
10. 10
    TemperatureAfter cooling the mixtures
11. 11
    workup.ADDITIONwas added
12. 12
    Otherthe reaction mixtures
13. 13
    workup.STIRRINGwith stirring
14. 14
    Extractionwere extracted with ethyl acetate
15. 15
    DryingThe organic layers were dried over anhydrous sodium sulfate
16. 16
    Concentrationwere then concentrated under reduced pressure

Procedure

A mixture of aluminium chloride 4.71 g, sodium azide 6.89 g and tetrahydrofuran 100 mL was stirred with heating under reflux for one hour. After the reaction mixtures were cooled under ice-cooling, thereto were added a mixture of the above-mentioned 1-chloro-3-isocyanato-2-methylbenzene and tetrahydrofuran 10 mL and the resulting mixtures were stirred with heating under reflux for five hours. After cooling the mixtures, to a mixture of sodium nitrite 10.59 g and water 300 mL was added the reaction mixtures with stirring. The mixtures were acidified with concentrated hydrochloric acid and were extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and were then concentrated under reduced pressure to give 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazole-5-one.

Source