Dimethyl Sulfoxide → HCID 86737702, compound

HRID 444184Notes

Reaction equation

HRID 444184 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:5])[CH3:4].C[C:15]1[CH:24]=[CH:23][C:18]([C:19](=[O:22])[CH2:20]Br)=[CH:17][CH:16]=1.[CH3:25]S(C)=O>O>[CH3:25][C:7]1([NH:6][C:3](=[O:5])[CH3:4])[CH:12]=[CH:11][C:10]([O:13][CH2:20][C:19]([C:18]2[CH:23]=[CH:24][CH:15]=[CH:16][CH:17]=2)=[O:22])=[CH:9][CH2:8]1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide3×HCID 1983AcetaminophenHCID 24758Sodium hydrideHCID 692722-Bromo-4'-methylacetophenone

Product 1

HCID 86737702HCID 86737702, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

65% Sodium hydride (2.2 g, 0.06 mole) was added to dimethylsulfoxide (60 ml), and a solution of 4-acetamidophenol (XV: R=CH3) (7.6 g, 0.05 mole) in dimethylsulfoxide (20 ml) was dropwise added thereto. After cooling to 5° to 10° C., a solution of 4-methylphenacyl chloride (XVI: X=Cl) (8.4 g, 0.05 mole) in dimethylsulfoxide (20 ml) was added dropwise thereto over 1 hour. Thereafter the reaction was carried out at 15° C. for 8 hours. The reaction mixture was diluted with water, and the precipitated crystals were filtered and recrystallized from acetone to obtain 7.9 g of 4-methyl-α-(4-acetamidophenoxy)acetophenone (XIII: R=CH3) as white crystals (yield, 55.8%).

Workup

  1. temperatureAfter cooling to 5° to 10° C.
  2. waitThereafter the reaction was carried out at 15° C. for 8 hours
  3. filtrationthe precipitated crystals were filtered
  4. customrecrystallized from acetone
  5. customto obtain

Sources & evidence

ORD record
ord-be154883230f4f4382378c532bebaa6d
Source dataset
uspto-grants-1981_04
Patent number
US04263219

Reaction notes

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