4'-Chloro-5-ethyl-2-hydroxybenzophenone-oxime → 3-(4-Chlorophenyl)5-ethyl-1,2-benzisoxazole

HRID 1606016Notes

Reaction equation

HRID 1606016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:18][OH:19])[C:9]2[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=2O)=[CH:4][CH:3]=1>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]3[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=3[O:19][N:18]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 1362714664'-Chloro-5-ethyl-2-hydroxybenzophenone-oxime

Product 1

HCID 125626723-(4-Chlorophenyl)5-ethyl-1,2-benzisoxazoleYield 7.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

4'-Chloro-5-ethyl-2-hydroxybenzophenone-oxime (22.0g) was dissolved in hot acetic anhydride (45ml) and immediately cooled, causing the oxime mono-acetate to crystallise. This was filtered and dried (19.7g) m.p. 105°C. The oxime mono-acetate (19.0g) and sodium carbonate (13.3g) were heated together in triglyme, under reflux, for 30 minutes. On cooling, the mixture was poured into water (1.0l.) this was extracted with ether (3×250ml). The combined ether extracts were washed with water (3×250ml) and evaporated to dryness to give a yellow oil which crystallised at room temperature (16.4G). A sample (3.0g) this solid was recrystallised from methanol/water to give a white solid (1.5g) m.p. 42°-45°C

Workup

  1. temperatureimmediately cooled
  2. customto crystallise
  3. filtrationThis was filtered
  4. customdried (19.7g) m.p. 105°C
  5. temperatureThe oxime mono-acetate (19.0g) and sodium carbonate (13.3g) were heated together in triglyme
  6. temperatureunder reflux, for 30 minutes
  7. temperatureOn cooling
  8. additionthe mixture was poured into water (1.0l.)
  9. extractionthis was extracted with ether (3×250ml)
  10. washThe combined ether extracts were washed with water (3×250ml)
  11. customevaporated to dryness
  12. customto give a yellow oil which
  13. customcrystallised at room temperature (16.4G)
  14. customA sample (3.0g) this solid was recrystallised from methanol/water

Sources & evidence

ORD record
ord-78f7748384dc4c2194e6c06ac5103875
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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