p-Aminoacetophenone → N-(p-acetylphenyl)acetamide

HRID 654827Notes

Reaction equation

HRID 654827 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>[OH-].[K+]>[C:11]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7468p-AminoacetophenoneHCID 7918Acetic Anhydride

Product 1

HCID 75937N-(p-acetylphenyl)acetamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

To 250 ml of KOH dried pyridine was added 50 g (0.37 mole) of p-aminoacetophenone and 39.6 g of acetic anhydride. After one and a half hours of stirring at room temperature, the solution had become a thick suspension of a white solid. Filtration and drying gave 44 g of p-acetamidoacetophenone. This solid (44 g, 0.25 mole) was then suspended in 500 ml methylene chloride and treated with 44 g Br2 (0.275 mole). The reaction was allowed to proceed overnight whereupon it was stripped and dried under high vacuum, then suspended in 200 ml absolute EtOH and treated with 60 g 2-amino-2-thiazoline (0.59 mole). The reaction was stirred for 2 days then stripped, taken up in water and extracted with methylene chloride. The organic phase was washed with water, brine and was dried with sodium sulfate. Flash column chromatography with 2% MeOH/98% CH2Cl2 gave 10.2 g (0.039 mole) of the Formula (III) compound, 6-acetamidophenyl-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. additiona thick suspension of a white solid
  2. filtrationFiltration
  3. customdrying

Sources & evidence

ORD record
ord-5a61f12c9d98480c9f0e8fc6381b4f6c
Source dataset
uspto-grants-1992_07
Patent number
US05134150

Reaction notes

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