Hydrochloric Acid → 1-(2-Methylphenyl)-1,2-dihydro-5H-tetrazol-5-one

HRID 1048608Notes

Reaction equation

HRID 1048608 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[N:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=[C:10]=[O:11].N([O-])=O.[Na+].Cl>O.CN(C)C=O>[CH3:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:9]1[C:10](=[O:11])[NH:7][N:6]=[N:5]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 691942-Tolyl isocyanateHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 1361865751-(2-Methylphenyl)-1,2-dihydro-5H-tetrazol-5-oneYield 104.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, to N,N-dimethylformamide 500 mL was added anhydrous aluminum chloride 55.1 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 26.9 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-isocyanato-2-methylbenzene 50.6 g and the resulting mixtures were heated at 70° C. for four hours. After cooling, to a mixture of sodium nitrite 51.8 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-methylphenyl)-1,4-dihydrotetrazole-5-one 69.8 g.

Workup

  1. stirringthe resulting mixtures were stirred for fifteen minutes
  2. additionwas added the reaction solutions
  3. stirringwith stirring
  4. extractionwere extracted with ethyl acetate
  5. washThe organic layers were washed with water and saturated saline
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. concentrationwere then concentrated under reduced pressure

Sources & evidence

ORD record
ord-98a53c5312c24f17bf83052acf7df3ba
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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