Dimethyl Sulfone → 1-[3,5-Bis(dimethylamino)phenyl]-2-(methanesulfonyl)ethan-1-one

HRID 441309Notes

Reaction equation

HRID 441309 reaction equation
[H-].[Na+].[CH3:3][S:4]([CH3:7])(=[O:6])=[O:5].[CH3:8][N:9]([CH3:23])[C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([N:20]([CH3:22])[CH3:21])[CH:19]=1)[C:13](OC)=[O:14]>CS(C)=O>[CH3:21][N:20]([CH3:22])[C:18]1[CH:17]=[C:12]([C:13](=[O:14])[CH2:3][S:4]([CH3:7])(=[O:6])=[O:5])[CH:11]=[C:10]([N:9]([CH3:8])[CH3:23])[CH:19]=1

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 20290435Methyl 3,5-bis(dimethylamino)benzoate

Product 1

HCID 202903961-[3,5-Bis(dimethylamino)phenyl]-2-(methanesulfonyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 3.6 g. of sodium hydride (50% dispersion in oil) and 9.4 g. of dimethylsulfone in 50 ml. of absolute dimethylsulfoxide was stirred with the exclusion of moisture for 2.5 hours at 50° C. and then treated with 11.1 g. of methyl 3,5-bis(dimethylamino)benzoate. The mixture was stirred for 18 hours at room temperature, diluted with 500 ml. of water and extracted with 600 ml. of ethyl acetate. The ethyl acetate phases were washed with 300 ml. of water, dried over magnesium sulfate and evaporated to dryness in vacuo. Recrystallization of the residue from ethyl acetate yielded 3',5'-bis-(dimethylamino)-2-methylsulfonylacetophenone, having a melting point of 151°-153° C.

Workup

  1. additionA suspension of 3.6 g
  2. additiontreated with 11.1 g
  3. additiondiluted with 500 ml
  4. extractionof water and extracted with 600 ml
  5. washThe ethyl acetate phases were washed with 300 ml
  6. dry with materialof water, dried over magnesium sulfate
  7. customevaporated to dryness in vacuo
  8. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-09084edea3f2412298bdddb2156a796e
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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