Methyl iodide → 2-(2-Methyl-tetrazol-5-yl)-benzaldehyde

HRID 1068924Notes

Reaction equation

HRID 1068924 reaction equation
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:4][N:3]=[N:2]1.[C:14](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C=O)C.O1CCOCC1>[CH3:14][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:4]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178519511HCID 178519511, compound

Product 1

HCID 211906432-(2-Methyl-tetrazol-5-yl)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

With the exclusion of air, 8.0 g (45.9 mmol) of 2-(tetrazol-5-yl)-benzaldehyde are added to 19 g (138 mmol) of potassium carbonate in 100 ml of DMF/dioxane (1:1) in an ice bath. 4.25 ml (68 mmol) of methyl iodide are added dropwise thereto and the reaction mixture is stirred in the ice bath for 1 hour and at RT for 1.5 hours. The mixture is stirred into 1 liter of icewater and 0.6 liter of ethyl acetate and the aqueous phase is separated off and extracted twice more with ethyl acetate. The organic phases are washed four times with water and with brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/ethyl acetate=3:1) and stirring in hexane yield 2-(2-methyl-tetrazol-5-yl)-benzaldehyde; TLC: Rf=0.41 (hexanelethyl acetate=3:1); FAB-MS: (M+H)+=189.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted twice more with ethyl acetate
  3. washThe organic phases are washed four times with water
  4. dry with materialwith brine, dried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c66045a00d1d4b41948a33c2604e5812
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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