Methyl iodide → 4-(2-Methyl-2H-tetrazol-5-yl)-benzaldehyde

HRID 1068902Notes

Reaction equation

HRID 1068902 reaction equation
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)=[N:4][N:3]=[N:2]1.[C:14]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O1CCOCC1>[CH3:14][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH:10]=[O:11])=[CH:12][CH:13]=2)=[N:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Product 1

HCID 104878484-(2-Methyl-2H-tetrazol-5-yl)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 217120691,4-dioxane N,N-dimethylformamideSolvent2×

Procedure

With ice-cooling, a solution of 75.5 g (0.434 mol) of 4-(tetrazol-5-yl)-benzaldehyde (Step 35.1) in 550 ml of DMF/dioxane (1:1) is added dropwise to 179.7 g (1.30 mol) of K2CO3 in 200 ml of DMF/dioxane (1:1); stirring is carried out for 30 min and then 40 ml (0.64 mol) of methyl iodide are added dropwise. The reaction mixture is stirred for 3 hours in an ice bath and finally for 15 hours at RT, poured into 2.8 liters of ice-water and stirred for 10 min, and the compound is filtered off and washed with water, yielding 4-(2-methyl-2H-tetrazol-5-yl)-benzaldehyde; m.p. 137-139° C.

Workup

  1. temperatureWith ice-cooling
  2. stirringThe reaction mixture is stirred for 3 hours in an ice bath and finally for 15 hours at RT
  3. stirringstirred for 10 min
  4. filtrationthe compound is filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-f2e9d3180b19415a99c72c9bd1e4882f
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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