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

HRID 222420Notes

Reaction equation

HRID 222420 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][CH:15](Br)C.C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O.C(Cl)(Cl)Cl>[Br:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1983AcetaminophenHCID 78891,3-DibromobutaneHCID 11430Potassium Carbonate

Product 1

HCID 10849771N-[4-(3-bromopropoxy)phenyl]acetamideYield 75.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of N-(4-hydroxyphenyl)acetamide (paracetamol) (1) (1.50 g) and 1,3-dibromobutane (14) (10.0 ml) in ethyl methyl ketone (25.0 ml) containing potassium carbonate (5.0 g) was stirred overnight at room temperature. The reaction mixture was filtered, residue washed with ethyl methyl ketone and solvent evaporated under reduced pressure to get the residue. The residue was dissolved in chloroform (200.0 ml), washed with 5% NaOH solution (3×100 ml), water (3×50 ml), dried, filtered and crystallized from methanol to get the desired product N-[4-(3-Bromo-propoxy)-phenyl]-acetamide (16) (2.01 g, 75.8%), mp 115-118° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washresidue washed with ethyl methyl ketone and solvent
  3. customevaporated under reduced pressure
  4. customto get the residue
  5. washwashed with 5% NaOH solution (3×100 ml), water (3×50 ml)
  6. customdried
  7. filtrationfiltered
  8. customcrystallized from methanol

Sources & evidence

ORD record
ord-6a4785e6ef5844c69e7b5a35e512d58b
Source dataset
uspto-grants-2012_06
Patent number
US08207222B2

Reaction notes

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