Potassium Carbonate → Methyl 2-methoxy-5-(2-methyl-2H-tetrazol-5-yl)benzoate

HRID 391403Notes

Reaction equation

HRID 391403 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]2[NH:17][N:16]=[N:15][N:14]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:18](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[N:15][N:16]([CH3:18])[N:17]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178497409HCID 178497409, compound

Product 1

HCID 58993674Methyl 2-methoxy-5-(2-methyl-2H-tetrazol-5-yl)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 2-methoxy-5-(1H-tetrazol-5-yl)benzoate (0.78 g, 3.33 mmol) methyl iodide (0.21 mL, 3.33 mmol) and potassium carbonate (0.46 g, 3.33 mmol) were combined in acetone (8 mL) and heated at reflux overnight. After cooling to room temperature, the mixture was filtered and concentrated. Flash chromatography on silica gel afforded 170 mg (21%). LC/MS (HPLC method 3): tR=2.01 min, 249.09 (MH)+

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customFlash chromatography on silica gel afforded 170 mg (21%)

Sources & evidence

ORD record
ord-d38f2962d03e4af6b0d5ab65b7066d6f
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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