Dimethyl Sulfoxide → HCID 21280980, compound

HRID 462543Notes

Reaction equation

HRID 462543 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]([O:21][CH3:22])[C:18]([N:23]([CH3:25])[CH3:24])=[C:17]([O:26][CH3:27])[CH:16]=1>C(O)(=O)C.O>[CH3:25][N:23]([CH3:24])[C:18]1[C:17]([O:26][CH3:27])=[CH:16][C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])=[CH:20][C:19]=1[O:21][CH3:22]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 11708520Benzoic acid, 4-(dimethylamino)-3,5-dimethoxy-, methyl ester

Product 1

HCID 21280980HCID 21280980, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of 21.6 g. of dimethylsulfone and 7.7 g. of sodium hydride (50% dispersion in oil) in 80 ml. of absolute dimethylsulfoxide was stirred at 50° C. for 3 hours under an atmosphere of nitrogen and the exclusion of moisture. The mixture was cooled to 30° C. and 15.6 g. of 4-(dimethylamino)-3,5-dimethoxybenzoic acid methyl ester were added. After stirring at room temperature for 4 hours, 500 ml. of water were added and the solution was made neutral with glacial acetic acid. The precipitate was removed by filtration with suction, washed with water, dried, recrystallized from ethyl acetate/cyclohexane, whereby there was obtained 4'-(dimethylamino)-3',5'-dimethoxy-2-(methylsulfonyl)-acetophenone having a melting point of 111°-112° C.

Workup

  1. additionA suspension of 21.6 g
  2. customThe precipitate was removed by filtration with suction
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-423c68092abc4589896127800c04e37f
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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