Water → HCID 10750107, compound

HRID 1068920Notes

Reaction equation

HRID 1068920 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=[O:10])=[N:4][N:3]=[N:2]1.[C:14](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C.O1CCOCC1>[CH3:14][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=[O:10])=[N:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178519552HCID 178519552, compound

Product 1

HCID 10750107HCID 10750107, compound

Reagents, catalysts & solvents 1

HCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

With the exclusion of air, 10.0 g (57.4 mmol) of 3-(tetrazol-5-yl)-benzaldehyde are added to 23.7 g (172 mmol) of potassium carbonate in 120 ml of DMF/dioxane (1:1) in an ice bath. 5.37 ml (86 mmol) of methyl iodide are added dropwise thereto and the reaction mixture is stirred for 2 hours in the ice bath and for 1 hour at RT. The reaction mixture is stirred into 0.5 liter of water, and the crude product is filtered off with suction and washed with water. Dissolution in 0.3 liter of ethyl acetate, washing with brine, drying (Na2SO4), concentration by evaporation and stirring in diethyl ether yield 3-(2-methyl-tetrazol-5-yl)-benzaldehyde; TLC: Rf=0.47 (hexanelethyl acetate=3:1).

Workup

  1. filtrationthe crude product is filtered off with suction
  2. washwashed with water
  3. dissolutionDissolution in 0.3 liter of ethyl acetate
  4. washwashing with brine
  5. customdrying
  6. concentration(Na2SO4), concentration
  7. customby evaporation

Sources & evidence

ORD record
ord-7fc3457a2e8544d984b7c81863718cf5
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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