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

HRID 745965Notes

Reaction equation

HRID 745965 reaction equation
N#N.[OH-].[Na+].[C:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)(=[O:7])[CH3:6].Br[CH2:17][CH2:18][CH2:19][Cl:20]>C(O)C>[C:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:17][CH2:18][CH2:19][Cl:20])=[CH:11][CH:10]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 947NitrogenHCID 1983AcetaminophenHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide

Product 1

HCID 5147668N-[4-(3-chloropropoxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round bottomed flask equipped with magnetic stirring, reflux condenser, and N2 atmosphere was placed ethanol (500 ml), sodium hydroxide (15.0 g), 4-acetamidophenol of Formula XXIII (30.0 g), and 1-bromo-3-chloropropane of Formula XXII (47.0 g) and the mixture was refluxed overnight. Upon cooling off-white crystals were deposited and then collected. The mother liquor was evaporated to dryness and dissolved in CH2Cl2 then washed with H2O, dried, and concentrated to 50 ml. A second crop of crystals were deposited. These were combined with the first crop of crystals and recrystallized from ethanol to give colorless crystals (20.3 g), mp 128°-130° C.

Workup

  1. customIn a round bottomed flask equipped with magnetic stirring
  2. temperaturereflux condenser
  3. temperaturethe mixture was refluxed overnight
  4. temperatureUpon cooling off-white crystals
  5. customcollected
  6. customThe mother liquor was evaporated to dryness
  7. dissolutiondissolved in CH2Cl2
  8. washthen washed with H2O
  9. customdried
  10. concentrationconcentrated to 50 ml
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-241cae55cea641908ff6b4613311ee1d
Source dataset
uspto-grants-1986_07
Patent number
US04602023

Reaction notes

Loading…