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

HRID 1451642Notes

Reaction equation

HRID 1451642 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.C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20][CH2:21]Br>CN(C=O)C>[Br:18][CH2:19][CH2:20][CH2:21][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 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 10849771N-[4-(3-bromopropoxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-hydroxyphenyl)acetamide (10 g) and potassium carbonate (11 g) in DMF (200 ml) was stirred for 20 min at room temperature. 1,3-Dibromopropane (35 ml) was then added and stirring was continued for 4 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was treated with water and extracted with dichloromethane. The organic phase was washed first with dilute sodium hydroxide, then with water, dried and concentrated to give a solid which was triturated with hexane to give the title compound (14 g), MP: 120°.

Workup

  1. stirringstirring
  2. waitwas continued for 4 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was treated with water
  6. extractionextracted with dichloromethane
  7. washThe organic phase was washed first with dilute sodium hydroxide
  8. dry with materialwith water, dried
  9. concentrationconcentrated
  10. customto give a solid which
  11. customwas triturated with hexane

Sources & evidence

ORD record
ord-764df50af8924601b61364ae28220610
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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