1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)benzamide

HRID 330414Notes

Reaction equation

HRID 330414 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 650524-Hydroxybenzamide

Product 1

HCID 144071764-(3-Chloropropoxy)benzamideYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 50 g (0.365 mole) of 4-hydroxybenzamide, 114.8 g (0.729 mole) of 1-bromo-3-chloropropane and 151.3 g (1.1 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 20 hr. The mixture was concentrated under reduced pressure and the rsidue was stirred with 1.2 liter of water to remove inorganic solids. The mixture was filtered and the filter cake was washed with water and petroleum ether and dried to yield 75.5 g (97%) of the title compound as a white solid. An analytical sample was recrystallized from ethyl acetate, m.p. 142°-143° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto remove inorganic solids
  5. filtrationThe mixture was filtered
  6. washthe filter cake was washed with water and petroleum ether
  7. customdried

Sources & evidence

ORD record
ord-047718a7b25e48d0a72aac785f2c69f1
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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