Dimethyl Sulfone → 1-[3,5-Bis(dimethylamino)-4-methylphenyl]-2-(methanesulfonyl)ethan-1-one

HRID 441300Notes

Reaction equation

HRID 441300 reaction equation
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].[CH3:8][N:9]([CH3:24])[C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([N:21]([CH3:23])[CH3:22])[C:19]=1[CH3:20])[C:13](OC)=[O:14]>CS(C)=O>[CH3:23][N:21]([CH3:22])[C:18]1[CH:17]=[C:12]([C:13](=[O:14])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])[CH:11]=[C:10]([N:9]([CH3:24])[CH3:8])[C:19]=1[CH3:20]

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 20290395Methyl 3,5-bis(dimethylamino)-4-methylbenzoate

Product 1

HCID 202903891-[3,5-Bis(dimethylamino)-4-methylphenyl]-2-(methanesulfonyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 18.8 g. of dimethylsulfone and 3.6 g. of sodium hydride (50% dispersion in oil) in 80 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 2 hours at 50° C. Thereupon, 23.6 g. of methyl 3,5-bis(dimethylamino)-4-methylbenzoate were added and the mixture was stirred at room temperature for 1.5 hours. The solution was diluted with 400 ml. of water and extracted twice with ethyl acetate. The ethyl acetate phases were combined, washed with water, dried over sodium sulfate and evaporated to dryness in vacuo. After recrystallization of the residue from methanol, there was obtained 3',5' -bis(dimethylamino)-4'-methyl-2-methylsulfonylacetophenone, having a melting point of 161°-163° C.

Workup

  1. additionA suspension of 18.8 g
  2. additionThe solution was diluted with 400 ml
  3. extractionof water and extracted twice with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness in vacuo
  7. customAfter recrystallization of the residue from methanol

Sources & evidence

ORD record
ord-b35146af9b4147958c8613a2feacb9d9
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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