Dimethyl Sulfoxide → HCID 21280950, compound

HRID 542983Notes

Reaction equation

HRID 542983 reaction equation
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].CS(C)=O.C[O:13][C:14](=O)[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([N:22]([CH3:24])[CH3:23])=[C:17]([CH3:25])[CH:16]=1>C(O)(=O)C.O>[CH3:24][N:22]([CH3:23])[C:18]1[C:17]([CH3:25])=[CH:16][C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])=[CH:20][C:19]=1[CH3:21]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 143324N,N,2,6-Tetramethylaniline-4-carboxylic acid, methyl ester

Product 1

HCID 21280950HCID 21280950, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 24.5 g. of dimethylsulfone and 9.1 g. of sodium hydride (50% dispersion in oil) in 50 ml. of absolute dimethylsulfoxide was stirred at 50° C. under an atmosphere of nitrogen and the exclusion of moisture for 3 hours. Then, it was treated with 16 g. of 4-(dimethylamino)-3,5-dimethyl-benzoic acid methyl ester. The mixture was stirred at 80° C. for 45 minutes, cooled and dissolved in 300 ml. of water. The solution was neutralized with glacial acetic acid. The precipitate was removed by filtration with suction, washed with water and recrystallized from alcohol, whereby there was obtained 4'-(dimethylamino) 3',5'-dimethyl-2-(methylsulfonyl)-acetophenone having a melting point of 132°-133° C.

Workup

  1. additionA suspension of 24.5 g
  2. additionThen, it was treated with 16 g
  3. temperaturecooled
  4. dissolutiondissolved in 300 ml
  5. customThe precipitate was removed by filtration with suction
  6. washwashed with water
  7. customrecrystallized from alcohol

Sources & evidence

ORD record
ord-15aeb318295643d59de68a3946609e9d
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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