Methyl iodide → HCID 15111353, compound

HRID 604472Notes

Reaction equation

HRID 604472 reaction equation
[C:1]1([C:7](=[O:14])[CH2:8][C:9]2[N:10]=[N:11][NH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15]I>CC(C)=O>[CH3:15][N:10]1[C:9]([CH2:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:14])=[N:13][N:12]=[N:11]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 10487846HCID 10487846, compound

Product 1

HCID 15111353HCID 15111353, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Phenyl-2-(2H-tetrazol-5-yl)-ethanone (13.24 g, 70.4 mmol) was dissolved in acetone (300 mL). MeI (4.6 mL, 73.9 mmol) and KCO3 (10.68 g, 77.4 mmol) were added and the reaction mixture was heated to reflux for 30 min. The reaction mixture was filtered and the solvent was removed in vacuo. The crude product contains a mixture of 2-(1-methyl-1H-tetrazol-5-yl)-1-phenyl-ethanone and 2-(2-methyl-2H-tetrazol-5-yl)-1-phenyl-ethanone. The two compounds were separated by flash column chromatography using ethyl acetate/hexane (6/4) as eluent. 2-(1-Methyl-1H-tetrazol-5-yl)-1-phenyl-ethanone was obtained as a white solid. Yield: 34%.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent was removed in vacuo
  5. additiona mixture of 2-(1-methyl-1H-tetrazol-5-yl)-1-phenyl-ethanone and 2-(2-methyl-2H-tetrazol-5-yl)-1-phenyl-ethanone
  6. customThe two compounds were separated by flash column chromatography

Sources & evidence

ORD record
ord-e91ea74788274f6fae9e2c19acc912df
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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