Dimethyl Sulfoxide → HCID 21280984, compound

HRID 542937Notes

Reaction equation

HRID 542937 reaction equation
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].CS(C)=O.C[O:13][C:14](=O)[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([NH:23][C:24](=[O:26])[CH3:25])=[C:17]([O:27][CH3:28])[CH:16]=1>O>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])[CH:16]=[C:17]([O:27][CH3:28])[C:18]=1[NH:23][C:24](=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 54250227HCID 54250227, compound

Product 1

HCID 21280984HCID 21280984, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 30.1 g. of dimethylsulfone and 11.5 g. of sodium hydride (50% dispersion in oil) in 80 ml. of dimethylsulfoxide was stirred at 50° C. for 3 hours with the exclusion of moisture. Then, 20.3 g. of 4-acetamido-3,5-dimethoxy-benzoic acid methyl ester were added and the mixture was stirred at room temperature for an additional 20 hours. Thereafter, the solution was diluted with 1 liter of water and extracted with three 1 liter portions of ethyl acetate. The ethyl acetate extracts were washed with two 300 ml. portions of water, combined, dried over magnesium sulfate and evaporated to dryness under vacuum. Recrystallization of the residue from ethyl acetate gave 2',6'-dimethoxy-4'-[(methylsulfonyl-acetyl)]-acetanilide having a melting point of 206°-207° C.

Workup

  1. additionA suspension of 30.1 g
  2. extractionextracted with three 1 liter portions of ethyl acetate
  3. washThe ethyl acetate extracts were washed with two 300 ml
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under vacuum
  6. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-38c50955e89344e08c9420463807afb3
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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