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

HRID 1193659

Reaktionsgleichung

Reaktionsgleichung von HRID 1193659
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 14407185N-[3-(3-Chloropropoxy)phenyl]ureaAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-58d5f522eb864f38ac8325b0bf7b2394
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810713

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