Benzocaine → Ethyl 4-amino-3-chlorobenzoate

HRID 3584

Reaktionsgleichung

Reaktionsgleichung von HRID 3584
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Cl:13]N1C(=O)CCC1=O>ClCCl>[Cl:13][C:12]1[CH:11]=[C:5]([CH:4]=[CH:3][C:2]=1[NH2:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

4

Edukt 2

HCID 2337BenzocaineHCID 31398Chlorosuccinimide

Produkt 1

HCID 1515285Ethyl 4-amino-3-chlorobenzoateAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 8.26 g of ethyl 4-aminobenzoate, 8.26 g of N-chlorosuccinimide in 50 ml of dichloromethane is refluxed overnight. The mixture is washed with saturated NaHCO3 solution and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated and hexane added. Chilling gives 7.38 g of ethyl 3-chloro-4-aminobenzoate, m.p. 82°-83° C.

Aufarbeitung

  1. temperatureis refluxed overnight
  2. washThe mixture is washed with saturated NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. washthe filter cake washed with dichloromethane
  5. concentrationThe filtrate is concentrated
  6. additionhexane added
  7. temperatureChilling

Quellen und Nachweise

ORD-Eintrag
ord-ad9d485deb4a410790b440b0d8fd2a4a
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

Verknüpfte Notizen

Wird geladen…