Pyridine → Methyl [3-(3-bromopropoxy)anilino](oxo)acetate

HRID 620310

Reaktionsgleichung

Reaktionsgleichung von HRID 620310
[Cl-].[CH3:2][O:3][C:4](=[O:8])[C:5]([OH:7])=O.[Br:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].N1C=CC=CC=1>C(Cl)Cl>[Br:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([NH:17][C:5](=[O:7])[C:4]([O:3][CH3:2])=[O:8])[CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 4592563-(3-Bromopropoxy)-anilineHCID 86640482Oxalic acid monomethyl ester chloride

Produkt 1

HCID 19818630Methyl [3-(3-bromopropoxy)anilino](oxo)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1.5 ml of oxalic acid monomethyl ester chloride in 10 ml of methylene chloride is added dropwise to a solution of 3.5 g of 3-(3-bromopropoxy)-aniline and 1.3 ml of pyridine in 40 ml of methylene chloride in the course of 10 minutes. After stirring at room temperature for 2 hours, the mixture is poured onto water and extracted with methylene chloride. The combined extracts are evaporated and the residue is chromatographed on silica gel with methylene chloride/ethyl acetate (10:1). The eluate is evaporated and the residue is crystallised from ether/hexane. Methyl N-[3-(3-bromopropoxy)-phenyl]-oxamate of melting point 90°-91° is obtained.

Aufarbeitung

  1. additionthe mixture is poured onto water
  2. extractionextracted with methylene chloride
  3. customThe combined extracts are evaporated
  4. customthe residue is chromatographed on silica gel with methylene chloride/ethyl acetate (10:1)
  5. customThe eluate is evaporated
  6. customthe residue is crystallised from ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a0f471a770e345c8971c3ad1d2d29996
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04820726

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