Reaction #1135818

Reaction equation

sodium nitrite

aluminium chloride

sodium azide

tetrahydrofuran

3-trifluoromethyl-2-methylbenzoic acid chloride

tetrahydrofuran

hydrochloric acid

→

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

Solvents

water

Conditions

Workup

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

Procedure

A mixture of aluminium chloride 6.53 g, sodium azide 9.55 g and tetrahydrofuran 100 mL was stirred with heating under reflux for two hours. The reaction mixtures were cooled under ice-cooling and thereto were added 3-trifluoromethyl-2-methylbenzoic acid chloride and tetrahydrofuran 100 mL and the mixtures were stirred with heating under reflux for ten hours. After cooling the mixtures, to a mixture of sodium nitrite 14.7 g and water 200 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 the resulting mixtures were then concentrated under reduced pressure to give 1-(2-methyl-3-trifluoromethylphenyl)-1,4-dihydrotetrazole-5-one.

Source