Dimethyl Sulfate → HCID 13885835, compound

HRID 653155Notes

Reaction equation

HRID 653155 reaction equation
[C:1]([CH2:3][N:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])#[N:2].[C:22](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[CH3:22][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:5]=1[N:4]([CH2:3][C:1]#[N:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 132203752-[(Cyanomethyl)(phenyl)amino]-5-methoxybenzoic acid

Product 1

HCID 13885835HCID 13885835, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7.1 g (0.025 mole) of 2-[(cyanomethyl)phenylamino]-5-methoxybenzoic acid [P. C. Unangst and M. E. Carethers, J. Heterocyclic Chem., 21, 709 (1974)], 4.0 g (0.029 mole) of anhydrous potassium carbonate, and 3.0 ml (4.0 g; 0.032 mole) of dimethyl sulfate in 200 ml of acetonitrile was stirred at reflux for 24 hours. The mixture was cooled and filtered, and the filter cake was washed several times with fresh acetonitrile. The combined filtrates were evaporated to an oil, which crystallized upon standing at room temperature. Recrystallization from aqueous methanol yielded 5.1 g (68% yield) of the ester product. A sample recrystallized again as above was analytically pure, mp 107°-109° C.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe filter cake was washed several times with fresh acetonitrile
  5. customThe combined filtrates were evaporated to an oil, which
  6. customcrystallized
  7. customupon standing at room temperature
  8. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-a5fef822a61c45699d6045006759df31
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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