Methyl iodide → Benzaldehyde, 2-methoxy-5-(2H-tetrazol-2-yl)-

HRID 1941512Notes

Reaction equation

HRID 1941512 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[OH:9][C:10]1[CH:17]=[CH:16][C:15]([N:18]2[N:22]=[N:21][CH:20]=[N:19]2)=[CH:14][C:11]=1[CH:12]=[O:13]>CN(C)C=O.O>[CH3:1][O:9][C:10]1[CH:17]=[CH:16][C:15]([N:18]2[N:22]=[N:21][CH:20]=[N:19]2)=[CH:14][C:11]=1[CH:12]=[O:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 104879002-Hydroxy-5-tetrazol-2-yl-benzaldehyde

Product 1

HCID 10584328Benzaldehyde, 2-methoxy-5-(2H-tetrazol-2-yl)-Yield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.06 g) and methyl iodide (0.5 ml) were added to a solution of 2-hydroxy-5-tetrazol-2-yl-benzaldehyde (930 mg) in dimethylformamide (6 ml) at room temperature. The mixture was stirred for 2 h then evaporated to give an orange solid. This was dissolved in water (40 ml), extracted with dichloromethane (3×30 ml), dried (Na2 SO4) and evaporated. The residue was purified by FCC (dichloromethane) to give the title compound as a yellow solid (423 mg). T.l.c. (Ethyl acetate/cyclohexane(1:1)), Rf 0.44.

Workup

  1. customthen evaporated
  2. customto give an orange solid
  3. extractionextracted with dichloromethane (3×30 ml)
  4. customdried (Na2 SO4)
  5. customevaporated
  6. customThe residue was purified by FCC (dichloromethane)

Sources & evidence

ORD record
ord-716168c6d6e34b3c817545c40bcaff1a
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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