1-Bromo-3-chloropropane → N-[3-(3-Chloropropoxy)phenyl]urea

HRID 1193659

Reaction equation

HRID 1193659 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 12796m-Hydroxyphenylurea

Product 1

HCID 14407185N-[3-(3-Chloropropoxy)phenyl]ureaYield 83.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 45.6 g (0.3 mole) of 1-(3-hydroxyphenyl)urea, 94.5 g (0.6 mole) of 1-bromo-3-chloropropane, 124.4 g (0.9 mole) of anhydrous potassium carbonate and 1 liter of acetone was heated at reflux with mechanical stirring for 20 hr. The mixture was concentrated and the residue was slurried with 1.5 liters of water. The mixture was filtered and the filter cake was recrystallized from isopropanol to yield 57.0 g (83%) of off-white solid, m.p. 141°-143° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationThe mixture was concentrated
  4. filtrationThe mixture was filtered
  5. customthe filter cake was recrystallized from isopropanol

Sources & evidence

ORD record
ord-58d5f522eb864f38ac8325b0bf7b2394
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Linked notes

Loading…