Acetaminophen → N-[4-(3-chloropropoxy)phenyl]acetamide

HRID 1709824Notes

Reaction equation

HRID 1709824 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Br[CH:13]([Cl:16])[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(Cl)(Cl)Cl>[Cl:16][CH2:13][CH2:14][CH2:15][O:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-

Product 1

HCID 5147668N-[4-(3-chloropropoxy)phenyl]acetamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 6212ChloroformSolvent

Procedure

A mixture of 4-acetamidophenol, 182.2 g (1.2 mole), bromochloropropane, 157.4 g (1.0 mole), and potassium carbonate, 145.0 g (1.05 mole) was heated at reflux overnight in 700 ml of acetone. The acetone solution was refrigerated overnight and white crystals formed. This white solid was filtered and washed with acetone. The filtrate was stripped to dryness and the residue was dissolved in chloroform and extracted with 5% sodium hydroxide. Removal of chloroform gave an oil. The white solid was also dissolved in chloroform and extracted with 5% sodium hydroxide. Removal of chloroform gave a white solid. The white solid and oil were combined and placed in acetone in the refrigerator; white crystals were obtained. The white crystals were recrystallized twice from acetone. A 5 g-sample of the white crystals was recrystallized from acetone. This furnished 1.76 g (after drying in vacuo overnight at 80° C. (23%) of white, crystalline product; m.p. 125°-127° C.

Workup

  1. temperaturewas heated
  2. customwhite crystals formed
  3. filtrationThis white solid was filtered
  4. washwashed with acetone
  5. dissolutionthe residue was dissolved in chloroform
  6. extractionextracted with 5% sodium hydroxide
  7. customRemoval of chloroform
  8. customgave an oil
  9. extractionextracted with 5% sodium hydroxide
  10. customRemoval of chloroform
  11. customgave a white solid
  12. customwhite crystals were obtained
  13. customThe white crystals were recrystallized twice from acetone
  14. customA 5 g-sample of the white crystals was recrystallized from acetone
  15. customThis furnished 1.76 g (after drying in vacuo overnight at 80° C. (23%) of white, crystalline product

Sources & evidence

ORD record
ord-c357f0d5bff643cbb6276e2c7e312ed9
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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