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

HRID 34908

Reaction equation

HRID 34908 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 13853984N-(2,6-dimethylphenyl)-2-(4-oxo-3-thiazolidinyl)propionamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6a9aab5ee7f74d7c9c9deececbc2446a
Source dataset
uspto-grants-1988_08
Patent number
US04764514

Linked notes

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