Sodium Hydroxide → HCID 13035549, compound

HRID 2059230Notes

Reaction equation

HRID 2059230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([NH2:13])[O:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17](Cl)=[O:18].[OH-].[Na+]>C(O)C>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17]([NH:13][C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:12]=1)=[O:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 783922,6-Dichlorobenzoyl chlorideHCID 21040623-(4-chlorophenyl)isoxazol-5-amine

Product 1

HCID 13035549HCID 13035549, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Chlorophenyl)-5-aminoisoxazole (1 gram) and 2,6-dichlorobenzoylchloride (5 grams) were placed in a 100 ml. reaction vessel and heated to near reflux for 11/2 hours. The mixture was then cooled to room temperature and treated with 25 ml. of 2 N NaOH and 25 ml. ethanol. After refluxing for 2 hours, the ethanol was slowly removed at reduced pressure. A solid precipitate was collected by filtration. The remaining solution was treated with activated charcoal, filtered, and cooled to room temperature. The aqueous solution was extracted with chloroform. The chloroform was washed with water and dried (Na2SO4). Removal of the solvent afforded an oily product which was recrystallized from ether/hexane, m.p. 208°-209° C.

Workup

  1. customreaction vessel
  2. temperatureheated
  3. temperatureto near reflux for 11/2 hours
  4. additiontreated with 25 ml
  5. temperatureAfter refluxing for 2 hours
  6. customthe ethanol was slowly removed at reduced pressure
  7. filtrationA solid precipitate was collected by filtration
  8. additionThe remaining solution was treated with activated charcoal
  9. filtrationfiltered
  10. temperaturecooled to room temperature
  11. extractionThe aqueous solution was extracted with chloroform
  12. washThe chloroform was washed with water
  13. dry with materialdried (Na2SO4)
  14. customRemoval of the solvent
  15. customafforded an oily product which
  16. customwas recrystallized from ether/hexane, m.p. 208°-209° C.

Sources & evidence

ORD record
ord-855d4be5f4ae4026bd008b459ef3fed2
Source dataset
uspto-grants-1982_03
Patent number
US04322429

Reaction notes

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