Dimethyl Sulfoxide → 4'-Amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone

HRID 542980Notes

Reaction equation

HRID 542980 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]([NH2:22])=[C:17]([CH3:23])[CH:16]=1>C(O)(=O)C.O>[NH2:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])=[CH:16][C:17]=1[CH3:23]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

Product 1

HCID 212810124'-Amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 33 g. of dimethylsulfone and 11 g. of sodium hydride (50% dispersion in oil) in 160 ml. of absolute dimethylsulfoxide was stirred at 50° C. under an atmosphere of nitrogen and the exclusion of moisture for 3 hours. Then, 18 g. of 4-amino-3,5-dimethyl-benzoic acid methyl ester were added. The mixture was stirred at 80° C. for 30 minutes and at room temperature for 1 hour and then dissolved in 400 ml. of water. The solution was neutralized with glacial acetic acid. The precipitate which formed was removed by filtration with suction, washed with water, dried and recrystallized from ethyl acetate, whereby there was obtained 4'-amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone having a melting point of 179°-180° C.

Workup

  1. additionA suspension of 33 g
  2. dissolutiondissolved in 400 ml
  3. customThe precipitate which formed
  4. customwas removed by filtration with suction
  5. washwashed with water
  6. customdried
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-362444d035bd437ca374ada6b24e4d72
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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