Acetaminophen → n-[4-(4-Bromobutoxy)phenyl]acetamide

HRID 222421Notes

Reaction equation

HRID 222421 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)[CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][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

5

Reactant 3

HCID 1983AcetaminophenHCID 78891,3-DibromobutaneHCID 11430Potassium Carbonate

Product 1

HCID 21781339n-[4-(4-Bromobutoxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(4-hydroxyphenyl)acetamide (Paracetamol) (1) (1.50 g) and 1,3-dibromobutane (15) (10.0 ml) in acetonitrile (25.0 ml) containing potassium carbonate (5.0 g) was refluxed for 8 hrs. at room temperature. The reaction mixture was filtered and the filtrate was poured into ice cold water. The residue was filtered and 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-(4-bromobutoxy)phenyl]acetamide (17) (2.15 g, 77.06), mp 119-124° C.

Workup

  1. temperaturewas refluxed for 8 hrs
  2. customat room temperature
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate was poured into ice cold water
  5. filtrationThe residue was filtered
  6. washwashed with 5% NaOH solution (3×100 ml), water (3×50 ml)
  7. customdried
  8. filtrationfiltered
  9. customcrystallized from methanol

Sources & evidence

ORD record
ord-9d5a32fed7234197b7a542dfdc635f73
Source dataset
uspto-grants-2012_06
Patent number
US08207222B2

Reaction notes

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