Acetaminophen → N-{4-[(5-Bromopentyl)oxy]phenyl}acetamide

HRID 222419Notes

Reaction equation

HRID 222419 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][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O.C(Cl)(Cl)Cl>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][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 81001,5-DibromopentaneHCID 11430Potassium Carbonate

Product 1

HCID 12355860N-{4-[(5-Bromopentyl)oxy]phenyl}acetamideYield 72.15%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of N-(4-hydroxyphenyl)-acetamide (paracetamol) (1) (1.50 g, 0.01 mol) and 1,5-dibromopentane (9) (10.0 ml) in ethyl methyl ketone (25.0 ml) containing potassium carbonate (5.0 g) was stirred for 8 hr 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% sodium hydroxide solution (3×100 ml), water (3×50 ml), dried, filtered and crystallized from methanol to get the desired product N-[4-(5-bromo-pentoxy)-phenyl]-acetamide (11) (2.15 g, 72.15%), mp 110-111° 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% sodium hydroxide solution (3×100 ml), water (3×50 ml)
  6. customdried
  7. filtrationfiltered
  8. customcrystallized from methanol

Sources & evidence

ORD record
ord-c5d8c8f81a9045f3802240306d1ccb34
Source dataset
uspto-grants-2012_06
Patent number
US08207222B2

Reaction notes

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