2,6-Dimethylaniline → 3-Isoxazolecarboxamide, N-(2,6-dimethylphenyl)-5-ethyl-

HRID 345777Notes

Reaction equation

HRID 345777 reaction equation
[CH2:1]([C:3]1[O:7][N:6]=[C:5]([C:8]([OH:10])=O)[CH:4]=1)[CH3:2].C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:23][C:24]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:25]=1[NH2:26]>CN(C=O)C>[CH3:23][C:24]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:25]=1[NH:26][C:8]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[O:7][N:6]=1)=[O:10]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 64838115-Ethyl-isoxazole-3-carboxylic acid

Product 1

HCID 30761703-Isoxazolecarboxamide, N-(2,6-dimethylphenyl)-5-ethyl-Yield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.1 g (0.04 mole) of 5-ethyl isoxazole 3-carboxylic acid are dissolved in 100 ml of DMF under nitrogen, 13 g (0.08 mole) of carbonyl diimidazole are added and the mixture is stirred for 2 h at room temperature. 9.7 g (0.08 mole) of 2,6-dimethyl aniline are added and the mixture is stirred again for 48 h. After removal of the precipitate formed by filtration and evaporation of the solvent, the residue is crystallized from petroleum ether. M.p.=82°. The yield is 73%.

Workup

  1. stirringthe mixture is stirred again for 48 h
  2. customAfter removal of the precipitate
  3. customformed by filtration and evaporation of the solvent
  4. customthe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-a13ecd5d9bab466db49b7ae7b1e99f2d
Source dataset
uspto-grants-1991_10
Patent number
US05059614

Reaction notes

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