2,4-Dichlorobenzoyl chloride → HCID 13423444, compound

HRID 2164404Notes

Reaction equation

HRID 2164404 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:12][C:13]1[NH:14][O:15][C:16](=[O:18])[CH:17]=1>C(=O)(O)[O-].[Na+]>[CH3:12][C:13]1[N:14]([C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=2[Cl:1])[O:15][C:16](=[O:18])[CH:17]=1

Participants

4

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 1530003-Methylisoxazol-5-one

Product 1

HCID 13423444HCID 13423444, compoundYield 237.4%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
150 °C

Procedure

20.9 gm of 2,4-dichlorobenzoyl chloride was added to 5 gm of 3-methyl-3-isoxazolin-5-one. The reaction mixture was heated at 150° C. for 3 hours. The reaction was neutralized with 100 ml of saturated sodium bicarbonate solution and extracted with methylene chloride. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate and filtered. The solvent was stripped to yield 32.6 gm of the crude product. The product was recrystallized from methylene chloride-hexane yielding 6.4 gm, m.p. 137°-139° C.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5cca9d0e665b427eb50ebb4285378fc0
Source dataset
uspto-grants-1985_03
Patent number
US04504486

Reaction notes

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