Cesium carbonate → N-(4-Acetyl-2-methylphenyl)methanesulfonamide

HRID 1350844Notes

Reaction equation

HRID 1350844 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=1[CH3:16])(=O)=O.[CH3:19][S:20]([NH2:23])(=[O:22])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C(OCC)(=O)C>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[C:8]([CH3:16])[CH:9]=1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 72879MethanesulfonamideHCID 213024274-Acetyl-2-methylphenyl trifluoromethanesulfonate

Product 1

HCID 19873430N-(4-Acetyl-2-methylphenyl)methanesulfonamideYield 34.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A test tube for microwave was charged with tris(dibenzylidenacetone)dipalladium (0) chloroform adduct (205 mg, 0.20 mmol), 9,9-dimethyl-9H-xanthene-4,5-diyl)bis[diphenylphosphine] (345 mg, 0.60 mmol), 4-acetyl-2-methylphenyl trifluoromethanesulfonate (1.41 g, 5.0 mmol), methanesulfonamide (570 mg, 6.0 mmol), cesium carbonate (1.63 g, 7.0 mmol) and 1,4-dioxane (5 ml). The mixture was subjected to microwave irradiation at 120° C. with stirring for 10 minutes. Then, it was filterd off and the filtrate was concentrated under reduced pressure to furnish the crude residue which was applied to a silica gel chromatography column and eluted with a volume mixture of hexane:ethyl acetate (2/1) to give 390 mg (34% yield) of the title compound as a yellow solid.

Workup

  1. customirradiation at 120° C.
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto furnish the crude residue which
  4. washeluted with a volume mixture of hexane

Sources & evidence

ORD record
ord-39aa9f0c3dd24fdc96718daa7b282b3f
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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