Acetyl chloride → Phenacetin

HRID 481779Notes

Reaction equation

HRID 481779 reaction equation
[C:1]1([NH2:10])[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH3:9])=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl>[C:18]([NH:10][C:1]1[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH3:9])=[CH:3][CH:2]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 90764-Ethoxyaniline

Product 1

HCID 4754Phenacetin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g of phenetylamine was dissolved in 50 ml of methylene chloride, and 7.0 ml of triethylamine and 3.6 ml of acetyl chloride were added to the solution at 0° C. The solution was stirred at room temperature for 2 hours, washed with water, aqueous solution of citric acid, and saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate. After separating the desiccant by filtration, the solution was purified by silica gel column chromatography to obtain 5.52 g of N-acetylphenetylamine, which was white crystal (yield: 82%).

Workup

  1. washwashed with water, aqueous solution of citric acid, and saturated aqueous solution of sodium chloride
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customAfter separating the desiccant
  4. filtrationby filtration
  5. customthe solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f7bcce2edc34872a1bb84c1a451e865
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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