Acetone → HCID 22621002, compound

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

Reactant 4

HCID 180Acetone

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 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.