Acetone → HCID 22621002, compound

HRID 430429Notes

Reaction equation

HRID 430429 reaction equation
[CH3:1]I.[CH3:3][C:4]1[CH:12]=[CH:11]C(C(O)=O)=[C:6]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:5]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].C[C:25]([CH3:27])=[O:26]>>[CH3:3][C:4]1[CH:12]=[CH:11][C:27]([C:25]([O:21][CH3:18])=[O:26])=[C:6]([N:13]([CH3:1])[S:14]([CH3:17])(=[O:15])=[O:16])[CH:5]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22620944HCID 22620944, compound

Product 1

HCID 22621002HCID 22621002, compound

Procedure

Methyl iodide (22.0 ml) was added to a stirred suspension of 4-methyl-2-(N-methylsulphonylamino)benzoic acid (8.0 g) and anhydrous potassium carbonate (24.2 g) in acetone and the mixture was stirred and heated at reflux overnight. The mixture was cooled and filtered and the filtrate was evaporated to dryness. The residue was dissolved in dichloromethane and washed with aqueous sodium bicarbonate solution, water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give methyl 4-methyl-2-(N-methyl-N-methylsulphonylamino)benzoate (8.36 g) as a cream solid, m.p. 100-103° C.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with aqueous sodium bicarbonate solution, water
  8. dry with materialdried (magnesium sulphate)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9bea601e4f6d4f1cae3f909694faf4ac
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

Loading…