2,6-Dimethoxybenzoyl chloride → Isoxaben

HRID 462355Notes

Reaction equation

HRID 462355 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]([CH2:11][CH3:12])([CH3:10])[CH2:8][CH3:9])[CH:3]=1.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:16]=1[C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[CH2:8]([C:7]([C:4]1[CH:3]=[C:2]([NH:1][C:17](=[O:18])[C:16]2[C:20]([O:24][CH3:25])=[CH:21][CH:22]=[CH:23][C:15]=2[O:14][CH3:13])[O:6][N:5]=1)([CH3:10])[CH2:11][CH3:12])[CH3:9]

Participants

4

Reactant 2

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 924023-(1-Ethyl-1-methylpropyl)-5-isoxazolamine

Product 1

HCID 73672IsoxabenYield 91.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 3.36 Kg of 5-amino-3-(1-ethyl-1-methylpropyl)isoxazole in 65 liters of toluene was added portion-wise over thirty minutes 4.015 Kg of 2,6-dimethoxybenzoyl chloride. The reaction mixture was heated to reflux and stirred for forty-eight hours. It was then cooled to room temperature and concentrated to a volume of about 25 liters by evaporation of the solvent under reduced pressure. The product precipitated and was collected by filtration, washed with fresh toluene, and air dried to provide 6.084 Kg of N-[3-(1-ethyl-1-methylpropyl]-5-isoxazolyl]-2,6-dimethoxybenzamide. M.P. 172°-174° C. Yield 91%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated to a volume of about 25 liters by evaporation of the solvent under reduced pressure
  4. customThe product precipitated
  5. filtrationwas collected by filtration
  6. washwashed with fresh toluene, and air
  7. customdried

Sources & evidence

ORD record
ord-0b6113d9039843879736aa74515af55d
Source dataset
uspto-grants-1985_05
Patent number
US04515625

Reaction notes

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