2,6-Dimethylaniline → N-(2,6-dimethylphenyl)-2-(4-oxo-3-thiazolidinyl)propionamide

HRID 34908

Reaktionsgleichung

Reaktionsgleichung von HRID 34908
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][N:3]1[CH:7]([CH3:11])[C:8]([OH:10])=O.[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:14]=1[NH2:15].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:14]=1[NH:15][C:8](=[O:10])[CH:7]([N:3]1[C:2](=[O:1])[CH2:6][S:5][CH2:4]1)[CH3:11]

Komponenten

5

Edukt 3

HCID 68962,6-DimethylanilineHCID 10868DicyclohexylcarbodiimideHCID 232453502-(4-Oxo-3-thiazolidinyl)propionic acid

Produkt 1

HCID 13853984N-(2,6-dimethylphenyl)-2-(4-oxo-3-thiazolidinyl)propionamideAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-oxo-3-thiazolidinyl)propionic acid (2.00 g), 2.6-dimethylaniline (1.38 g), and dicyclohexylcarbodiimide (2.35 g) in chloroform (15 ml) was refluxed for 48 hours. The resultant precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with diethyl ether and recrystallized from ethanol to give N-(2,6-dimethylphenyl)-2-(4-oxo-3-thiazolidinyl)propionamide (1.45 g) as colorless prisms.

Aufarbeitung

  1. temperaturewas refluxed for 48 hours
  2. customThe resultant precipitate was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was triturated with diethyl ether
  5. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6a9aab5ee7f74d7c9c9deececbc2446a
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764514

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