Methanesulfonic Acid → 4-[2-(1-Methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-benzaldehyde

HRID 1458467Notes

Reaction equation

HRID 1458467 reaction equation
[C:1]1([C:7]([CH3:9])=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]1[C:14]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)=[N:13][N:12]=[N:11]1.CS(O)(=O)=O>C1(C)C=CC=CC=1>[CH3:8][C:7]([N:11]1[N:12]=[N:13][C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH:19]=[O:20])=[CH:21][CH:22]=2)=[N:10]1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 7407Alpha-MethylstyreneHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Product 1

HCID 183691004-[2-(1-Methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 6.9 g (58 mmol) of 2-phenyl-propene (Fluka, Buchs, Switzerland) and 22 ml of toluene is added dropwise to 10 g (57 mmol) of 4-(tetrazol-5-yl)-benzaldehyde and 1 g (5.7 mmol) of methanesulfonic acid in 44 ml of boiling toluene and the mixture is then stirred under reflux conditions for 1 hour. The cooled reaction mixture is washed 2× with sat. NaHCO3 solution, water and brine, dried (Na2SO4) and concentrated by evaporation to form the title compound: 1H-NMR (DMSO-d6) δ 10.09 (s, HCO), 8.29 and 8.08 (2d, J=8, each 2H), 7.33 and 7.17 (2m, 5H), 2.17 (s, 6H).

Workup

  1. customThe cooled reaction mixture
  2. washis washed 2× with sat. NaHCO3 solution, water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ffa544561f864163a48aecabefd3c10e
Source dataset
uspto-grants-1998_12
Patent number
US05849911

Reaction notes

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