2,4-Dichlorobenzoyl chloride → HCID 13423445, compound

HRID 2164405Notes

Reaction equation

HRID 2164405 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].[CH2:12]([C:15]1[NH:16][O:17][C:18](=[O:20])[CH:19]=1)[CH2:13][CH3:14]>C(=O)(O)[O-].[Na+]>[CH2:12]([C:15]1[N:16]([C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=2[Cl:1])[O:17][C:18](=[O:20])[CH:19]=1)[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 13423442HCID 13423442, compound

Product 1

HCID 13423445HCID 13423445, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

20.9 gm of 2,4-dichlorobenzoyl chloride was added to 8 gm of 3-n-propyl-3-isoxazolin-5-one. The system was heated at 100° C. for 3 hours. Afterwards, the system was neutralized with 150 ml of saturated sodium bicarbonate solution. The product was extracted with methylene chloride. The organic solution was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and filtered. The organic solution was stripped to yield 28.8 gm of the crude product as a brown oil. The product was purified by HPLC using 1:3 tetrahydrofuran/hexane as the eluant to yield the title compound as a brown solid, m.p. 63°-65.5° C.

Workup

  1. extractionThe product was extracted with methylene chloride
  2. washThe organic solution was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customto yield 28.8 gm of the crude product as a brown oil
  6. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-df7a85e36bde448db604946bad088132
Source dataset
uspto-grants-1985_03
Patent number
US04504486

Reaction notes

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