2,6-Dimethoxybenzoyl chloride → Isoxaben

HRID 980097Notes

Reaction equation

HRID 980097 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 91.8%

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 4.0015 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-f6cc9a1c74ed464bb538bf40012bc248
Source dataset
uspto-grants-1987_01
Patent number
US04636243

Reaction notes

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