Methyl iodide → HCID 22621194, compound

HRID 2257499Notes

Reaction equation

HRID 2257499 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:9]=1.CI>CC(C)=O>[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([N:18]([CH3:1])[S:19]([CH3:22])(=[O:20])=[O:21])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2799819HCID 2799819, compound

Product 1

HCID 22621194HCID 22621194, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (12.5 g) was added to a stirred solution of methyl 4-chloro-2-(N-methylsulphonylamino)benzoate (7.5 g) in acetone. The mixture was stirred for 15 minutes and methyl iodide (8.0 g) was added. The resultant mixture was stirred at room temperature for 1 hour and left to stand overnight. The mixture was evaporated to dryness and the residue was dissolved in ethyl acetate and washed with sodium hydroxide solution (2M) and water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give methyl 4-chloro-2-(N-methyl-N-methylsulphonylamino)benzoate (4.9g) as a white solid, m.p. 73°-75° C.

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe mixture was evaporated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with sodium hydroxide solution (2M) and water
  6. dry with materialdried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-78c32c59da8f4ea990a3c69006d547ba
Source dataset
uspto-grants-1997_08
Patent number
US05658858

Reaction notes

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