Phenylacetic Acid → N-butyl-2-phenylacetamide

HRID 70077Notes

Reaction equation

HRID 70077 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14]>S(=O)(=O)(O)O.CO>[CH2:11]([NH:15][C:8](=[O:10])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 999Phenylacetic AcidHCID 8007Butylamine

Product 1

HCID 221447N-butyl-2-phenylacetamideYield 70.7%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

Phenylacetic acid (16 g, 117.6 mmol) and methanol (60 ml) were added to a 250 ml three-necked flask, followed by addition of 5 drops of concentrated sulphuric acid. The resulting solution was heated to reflux for 6 hours. Then, the mixture was cooled to room temperature, followed by adding n-butylamine (12 ml, 121.4 mmol), and heated to reflux for another 3 hours. After the reaction was completed, it was cooled to room temperature. Most of the solvent was removed by rotary vacuum evaporation, 30 ml of water was added thereinto, and the mixture was extracted with ethyl acetate (3×80 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to yield 15.9 g of N-n-butylphenylacetamide (white solid, yield: 70.4%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 6 hours
  3. temperatureheated
  4. temperatureto reflux for another 3 hours
  5. temperatureit was cooled to room temperature
  6. customMost of the solvent was removed by rotary vacuum evaporation, 30 ml of water
  7. additionwas added
  8. extractionthe mixture was extracted with ethyl acetate (3×80 ml)
  9. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a2e6e511c55421aa16f0a2d192fcf97
Source dataset
uspto-grants-2014_09
Patent number
US08822519B2

Reaction notes

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