4'-Hydroxyacetophenone → HCID 28096015, compound

HRID 1914606Notes

Reaction equation

HRID 1914606 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([NH:10][CH3:11])=[O:9])=[O:4].[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:2][C:3]([NH:5][C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]([NH:10][CH3:11])=[O:9])=[O:4])=[CH:18][CH:19]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 43578842HCID 43578842, compound

Product 1

HCID 28096015HCID 28096015, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 2-(2-chloroacetamido)-N-methylbenzamide 22.65 g (0.1 mol) and p-hydroxyacetophenone 16.32 g (0.12 mol) in 200 mL of butanone was added 27.60 g (0.2 mol) potassium carbonate. The mixture was stirred and heated to reflux for 4-5 hours, and monitored by TLC until the reaction was over, the reaction mixture was concentrated under reduced pressure and extracted with 300 mL of ethyl acetate to separate the organic phase, the organic phase was washed with 50 ml of 5% sodium hydroxide aqueous solution and 50 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, and the residual was purified via silica gel column chromatography to obtain 27.50 g 2-(2-(4-acetylphenoxy)acetamido)-N-methylbenzamide as white solid with yield of 84.4%, m.p. 252-253° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4-5 hours
  3. concentrationwas concentrated under reduced pressure
  4. extractionextracted with 300 mL of ethyl acetate
  5. customto separate the organic phase
  6. washthe organic phase was washed with 50 ml of 5% sodium hydroxide aqueous solution and 50 ml of brine successively
  7. dry with materialdried via anhydrous magnesium sulfate
  8. customevaporated
  9. customthe residual was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-4f4f053f951b47d181655c645b146c92
Source dataset
uspto-grants-2013_12
Patent number
US08614214B2

Reaction notes

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