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

HRID 1413742Notes

Reaction equation

HRID 1413742 reaction equation
[H-].[Na+].[CH3:3][S:4]([CH3:7])(=[O:6])=[O:5].CS(C)=O.[CH3:12][N:13]([C:17]1[CH:18]=[C:19]([CH:24]=[C:25]([N:27](C)[C:28](=O)C)[CH:26]=1)[C:20](OC)=[O:21])C(=O)C>O.C(O)(=O)C>[CH3:28][NH:27][C:25]1[CH:24]=[C:19]([C:20](=[O:21])[CH2:3][S:4]([CH3:7])(=[O:6])=[O:5])[CH:18]=[C:17]([NH:13][CH3:12])[CH:26]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 20290399HCID 20290399, compound

Product 1

HCID 202903761-[3,5-Bis(methylamino)phenyl]-2-(methanesulfonyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 19.2 g. of sodium hydride (50% dispersion in oil) and 56.1 g. of dimethylsulfone in 200 ml. of absolute dimethylsulfoxide was stirred with the exclusion of moisture for 3 hours at 50° C. and then treated at 25° C. with 41.8 g. of methyl 3,5-bis-(N-methylacetamido)benzoate. The mixture was stirred for 18 hours at 25° C., diluted with 2 liters of water, adjusted to pH 7 with glacial acetic acid and extracted with 9 liters of ethyl acetate. The ethyl acetate solution was washed with 3 liters of water, dried over magnesium sulfate and evaporated in vacuo. Recrystallization of the residue from ethanol yielded 3',5'-bis(methylamino)-2-methylsulfonylacetophenone, having a melting point of 144°-146° C.

Workup

  1. additionA suspension of 19.2 g
  2. additiontreated at 25° C. with 41.8 g
  3. extractionextracted with 9 liters of ethyl acetate
  4. washThe ethyl acetate solution was washed with 3 liters of water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-f69371df6143454cb148c11e50ed0270
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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