Benzoyl Peroxide → HCID 14835355, compound

HRID 1198988Notes

Reaction equation

HRID 1198988 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]2=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:8][N:9]=[C:5]2[CH:4]=1)[CH3:2].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH:1]([C:3]1[CH:17]=[CH:16][C:6]2=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:8][N:9]=[C:5]2[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14835354HCID 14835354, compound

Product 1

HCID 14835355HCID 14835355, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1.9 g (0.0085 mole) of 6-ethyl-3-phenyl-2,1-benzisoxazole, 1.5 g (0.0087 mole) of N-bromosuccinimide and a few crystals of dibenzoyl peroxide in 100 ml of carbon tetrachloride was heated at reflux for 2 hr under floodlight illumination and under an argon atmosphere. The cooled reaction mixture was filtered, and the filtrate was washed twice with 100 ml portions of 10% sodium bicarbonate solution, once with water (100 ml) and dried over sodium sulfate. The sodium sulfate was removed by filtration and the filtrate was concentrated to a dark brown oil which solidified upon standing. The solid was purified by chromatography (3.5×60 cm glass column; 180 g of silica gel; benzene). Fractions containing the title compound were combined and the solvent was evaporated under reduced pressure to give a viscous oil which solidified upon standing. The solid was recrystallized from diethyl ether-petroleum ether (30°-60° C.) to give 1.7 g (65%) of mustard yellow crystals, m.p. 99°-102° C.

Workup

  1. temperatureat reflux for 2 hr under floodlight illumination and under an argon atmosphere
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. washthe filtrate was washed twice with 100 ml portions of 10% sodium bicarbonate solution, once with water (100 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe sodium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated to a dark brown oil which
  8. customThe solid was purified by chromatography (3.5×60 cm glass column; 180 g of silica gel; benzene)
  9. additionFractions containing the title compound
  10. customthe solvent was evaporated under reduced pressure
  11. customto give a viscous oil which
  12. customThe solid was recrystallized from diethyl ether-petroleum ether (30°-60° C.)
  13. customto give 1.7 g (65%) of mustard yellow crystals, m.p. 99°-102° C.

Sources & evidence

ORD record
ord-de9bb01876c6456c852773c4c57af8ea
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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