Hydrochloric Acid → HCID 136646196, compound

HRID 1048625Notes

Reaction equation

HRID 1048625 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]=[C:18]=[O:19])[C:12]=1[CH3:20].N([O-])=O.[Na+].Cl>O.CN(C)C=O>[CH3:20][C:12]1[C:11]([O:10][CH3:9])=[CH:16][CH:15]=[CH:14][C:13]=1[N:17]1[C:18](=[O:19])[NH:7][N:6]=[N:5]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium NitriteHCID 602087991261682-57-8

Product 1

HCID 136646196HCID 136646196, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, to N,N-dimethylformamide 180 mL was added anhydrous aluminum chloride 16.0 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 7.8 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-methoxy-3-isocyanato-2-methylbenzene 17.0 g and the resulting mixtures were heated at 80° C. for four and a half hours. After cooling the mixtures, to a mixture of sodium nitrite 25 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-methyl-3-methoxyphenyl)-1,4-dihydrotetrazole-5-one 16.2 g.

Workup

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

Sources & evidence

ORD record
ord-c17ba9c97c674a27b8788e2bc5c14839
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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