1-Bromo-3-chloropropane → N-[4-(3-Chloropropoxy)phenyl]carbamic acid ethyl ester

HRID 1709836Notes

Reaction equation

HRID 1709836 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].Br[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:15][CH2:16][CH2:17][Cl:18])=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 602288ethyl N-(4-hydroxyphenyl)carbamate

Product 1

HCID 14407186N-[4-(3-Chloropropoxy)phenyl]carbamic acid ethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.6 g (0.036 mole) of (4-hydroxyphenyl)carbamic acid ethyl ester, 11.5 g (0.072 mole) of 1-bromo-3-chloropropane, 13.8 g (0.10 mole) of anhydrous potassium carbonate and 150 ml of acetone was heated at reflux for 21 hr. The mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to give a solid residue. The solid was triturated with petroleum ether (30°-60° C.) collected by filtration and recrystallized from isopropanol to yield 7.7 g (83%) of white solid, m.p. 91°-93° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a solid residue
  7. customThe solid was triturated with petroleum ether (30°-60° C.)
  8. filtrationcollected by filtration
  9. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-1bc8098ad72d4006a7b30420c98e5bf0
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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