Hydrochloric Acid → HCID 21280953, compound

HRID 542941Notes

Reaction equation

HRID 542941 reaction equation
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].C[O:9][C:10](=O)[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([N:19]([CH3:23])[C:20](=[O:22])[CH3:21])=[C:13]([O:24][CH3:25])[CH:12]=1.Cl>O.CS(C)=O>[CH3:18][O:17][C:15]1[CH:16]=[C:11]([C:10](=[O:9])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])[CH:12]=[C:13]([O:24][CH3:25])[C:14]=1[N:19]([CH3:23])[C:20](=[O:22])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 54289209HCID 54289209, compound

Product 1

HCID 21280953HCID 21280953, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A suspension of 35.7 g. of dimethylsulfone and 12.0 g. of sodium hydride (50% dispersion in oil) in 100 ml. of absolute dimethylsulfoxide was stirred at 50° C. for 3 hours with the exclusion of moisture and subsequently treated with 34.0 g. of 3,5-dimethoxy-4-(N-methyl-acetamido)-benzoic acid methyl ester. After stirring at room temperature for 2.25 hours, the mixture was diluted with 1 liter of water. The resulting solution was made acidic with 3N hydrochloric acid and extracted with two 1 liter portions of ethyl acetate. The ethyl acetate extracts were washed with two 200 ml. portions of water, combined, dried over magnesium sulfate and evaporated in vacuo. Recrystallization of the residue from ethyl acetate gave 2',6'-dimethoxy-N-methyl-4'-[(methylsulfonyl)-acetyl]-acetanilide having a melting point of 141°-142° C.

Workup

  1. additionA suspension of 35.7 g
  2. additionsubsequently treated with 34.0 g
  3. extractionextracted with two 1 liter portions of ethyl acetate
  4. washThe ethyl acetate extracts were washed with two 200 ml
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-92af8d0525a94f41aa38abb9e25ed10e
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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