Methyl iodide → HCID 18696007, compound

HRID 1870233Notes

Reaction equation

HRID 1870233 reaction equation
CI.[C:3](=O)([O-])O.[Na+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[N:19][N:18]=[N:17]2)=[CH:12][C:11]=1[C:21](=[O:25])[C:22]([OH:24])=[O:23]>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[N:19][N:18]=[N:17]2)=[CH:12][C:11]=1[C:21](=[O:25])[C:22]([O:24][CH3:3])=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 18696015HCID 18696015, compound

Product 1

HCID 18696007HCID 18696007, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (1.87 ml, 4.26 g, 30 mmol) was added to a mixture of sodium hydrogen carbonate (2.52 g, 30 mmol), and 2-[2-methoxy-5-(1H-tetrazol-1-yl)phenyl]-2-oxoethanoic acid (3.37 g, 13.6 mmol) in dimethylformamide (120 ml) and the mixture was stirred at room temperature for 6 hours. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate (100 ml) and water (50 ml) were added and mixture was extracted with ethyl acetate (4×100 ml). The combined organic fractions were washed with saturated aqueous sodium hydrogen carbonate (4×100 ml), dried (MgSO4) and evaporated under reduced pressure to give methyl 2-[2-methoxy-5-(1H-tetrazol-1-yl)phenyl]-2-oxoethanoate as an orange solid (3.36 g, 94%), 1H NMR (CDCl3) δ 9.02 (1H, s), 8.11 (1H, d, J=2.8 Hz), 8.03 (1H, dd, J=9.0, 2.8 Hz), 7.23 (1H, d, J=9.0 Hz), 3.99 (3H, s), and 3.96 (3H, s).

Workup

  1. customThe solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate (100 ml) and water (50 ml)
  2. additionwere added
  3. extractionmixture was extracted with ethyl acetate (4×100 ml)
  4. washThe combined organic fractions were washed with saturated aqueous sodium hydrogen carbonate (4×100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-34808de1b0ec4911a39a7509317d829b
Source dataset
uspto-grants-2000_08
Patent number
US06096766

Reaction notes

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