Hydrochloric Acid → N-(4-Ethylphenyl)acetamide

HRID 1976517Notes

Reaction equation

HRID 1976517 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].Cl.[C:11](OC(=O)C)(=[O:13])[CH3:12].C([O-])(=O)C.[Na+]>O>[CH3:2][CH2:1][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11]([CH3:12])=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 115044-EthylanilineHCID 517045Sodium Acetate

Product 1

HCID 72893N-(4-Ethylphenyl)acetamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a 10-liter reaction flask were introduced 243.8 g (2.01 mol) of 4-ethylaniline, 2 liters of water, 230 g of concentrated hydrochloric acid, and 250 g of acetic anhydride. A solution prepared by dissolving 200 g of sodium acetate in 800 ml of water was added dropwise thereto at 10 to 20° C. This mixture was stirred overnight at room temperature, and the resultant precipitate was taken out by filtration. The crystals were washed with water and recrystallized from methanol (200 ml) to obtain 150 g of the target compound.

Workup

  1. customInto a 10-liter reaction flask
  2. customA solution prepared
  3. additionwas added dropwise
  4. customat 10 to 20° C
  5. filtrationthe resultant precipitate was taken out by filtration
  6. washThe crystals were washed with water
  7. customrecrystallized from methanol (200 ml)

Sources & evidence

ORD record
ord-1ee0bd23594c4dd99c28b7996828e482
Source dataset
uspto-grants-2001_05
Patent number
US06228547B1

Reaction notes

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