Dimethyl Sulfone → HCID 20290391, compound

HRID 441322Notes

Reaction equation

HRID 441322 reaction equation
[H-].[Na+].[CH3:3][S:4]([CH3:7])(=[O:6])=[O:5].[CH3:8][N:9]([CH3:28])[C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([N:25]([CH3:27])[CH3:26])[C:19]=1[N:20]([CH3:24])[C:21](=[O:23])[CH3:22])[C:13](OC)=[O:14]>CS(C)=O>[CH3:27][N:25]([CH3:26])[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]([CH3:28])[CH3:8])[C:19]=1[N:20]([CH3:24])[C:21](=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 20290411HCID 20290411, compound

Product 1

HCID 20290391HCID 20290391, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 0.77 g. of sodium hydride (50% suspension in oil) and 2.28 g. of dimethylsulfone in 28 ml. of dimethylsulfoxide was stirred with the exclusion of moisture and under nitrogen for 2 hours at 50° C. 2 G. of methyl 3,5-bis(dimethylamino)-4-(N-methylacetamido)benzoate were then added, the mixture heated to 70° C. for a short time and stirred for a further 2 hours without heating. The solution was diluted with 100 ml. of ice water, washed with 100 ml. of low-boiling petroleum ether, the product extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and evaporated. After purification of the residue over aluminum oxide with benzene and recrystallization from ethyl acetate/petroleum ether, there was obtained 2'.6'-bis(dimethylamino)-N-methyl-4'-[(methylsulfonyl)acetyl]acetanilide having a melting point of 130° C.

Workup

  1. additionA suspension of 0.77 g
  2. temperaturewithout heating
  3. additionThe solution was diluted with 100 ml
  4. washof ice water, washed with 100 ml
  5. extractionof low-boiling petroleum ether, the product extracted with ethyl acetate
  6. dry with materialthe ethyl acetate solution dried over sodium sulfate
  7. customevaporated
  8. customAfter purification of the residue over aluminum oxide
  9. customwith benzene and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-b4a5538c6bbb43fdb151c1338a2add99
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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