Hydrochloric Acid → 1-(2-Methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one

HRID 1048614Notes

Reaction equation

HRID 1048614 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Cl:9][C:10]1[C:11]([CH3:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)C(Cl)=O.[N:20]([O-])=O.[Na+].Cl.[O:25]1[CH2:29]CCC1>O>[CH3:19][C:11]1[C:10]([Cl:9])=[CH:18][CH:17]=[CH:16][C:12]=1[N:5]1[C:29](=[O:25])[NH:20][N:7]=[N:6]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 193677723-Chloro-2-methylbenzoyl chlorideHCID 23668193Sodium Nitrite

Product 1

HCID 1366461851-(2-Methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for two hours
  3. customAfter the reaction mixtures
  4. temperaturewere cooled under ice-
  5. temperaturecooling
  6. additionwas added
  7. stirringthe resulting mixtures were stirred
  8. temperaturewith heating
  9. temperatureunder reflux for ten hours
  10. temperatureAfter cooling the mixtures
  11. additionwas added
  12. customthe reaction mixtures
  13. stirringwith stirring
  14. extractionwere then extracted with ethyl acetate
  15. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  16. concentrationwere then concentrated under reduced pressure

Sources & evidence

ORD record
ord-0cbabd7d0a7f4b7983de1f60ec35d596
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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