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

HRID 1709835

Reaction equation

HRID 1709835 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 2-propanol 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 2-propanol

Sources & evidence

ORD record
ord-1630cbfc37ce4f36940b1fad5cd4f519
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Linked notes

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