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

HRID 1193646Notes

Reaction equation

HRID 1193646 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 refluxed 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. customwhite crystals formed
  2. filtrationThis white solid was filtered
  3. washwashed with acetone
  4. dissolutionthe residue was dissolved in chloroform
  5. extractionextracted with 5% sodium hydroxide
  6. customRemoval of chloroform
  7. customgave an oil
  8. extractionextracted with 5% sodium hydroxide
  9. customRemoval of chloroform
  10. customgave a white solid
  11. customwhite crystals were obtained
  12. customThe white crystals were recrystallized twice from acetone
  13. customA 5 g sample of the white crystals was recrystallized from acetone
  14. dry with materialThis furnished 1.76 g (after drying in vacuo overnight at 80° C.) (23%) of white crystalline product

Sources & evidence

ORD record
ord-9dac05e5d95a44108ef799edafcaa265
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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