Reaction #1135796

Reaction equation

sodium nitrite

aluminium chloride

sodium azide

tetrahydrofuran

3-chloro-2-methylbenzoic acid chloride

tetrahydrofuran

hydrochloric acid

→

1-(2-methyl-3-chlorophenyl)-1.4-dihydrotetrazole-5-one

Solvents

water

Conditions

Workup

1. 1
   Temperaturewith heating
2. 2
   Temperatureunder reflux for two hours
3. 3
   OtherAfter the reaction mixtures
4. 4
   Temperaturewere cooled under ice-
5. 5
   Temperaturecooling
6. 6
   workup.ADDITIONwas added
7. 7
   workup.STIRRINGthe resulting mixtures were stirred
8. 8
   Temperaturewith heating
9. 9
   Temperatureunder reflux for ten 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 then 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 33.6 g, sodium azide 49.2 g and tetrahydrofuran 100 mL was stirred with heating under reflux for two hours. After the reaction mixtures were cooled under ice-cooling, and thereto was added a mixture of the above-mentioned 3-chloro-2-methylbenzoic acid chloride and tetrahydrofuran 100 mL and the resulting mixtures were stirred with heating under reflux for ten hours. After cooling the mixtures, to a mixture of sodium nitrite 75.6 g and water 500 mL was added the reaction mixtures with stirring. The mixtures were acidified with concentrated hydrochloric acid and were then 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