Benzoyl Peroxide → HCID 14835351, compound

HRID 1198985Notes

Reaction equation

HRID 1198985 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]2=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:7][N:8]=[C:4]2[CH:3]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:16]=[CH:15][C:5]2=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:7][N:8]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 610558HCID 610558, compound

Product 1

HCID 14835351HCID 14835351, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 13.3 g (0.064 mole) of 6-methyl-3-phenyl-2,1-benzisoxazole, 11.3 g (0.064 mole) of N-bromosuccinimide, 0.1 g of dibenzoylperoxide and 225 ml of carbon tetrachloride was heated at reflux under illumination by a flood lamp for 2.5 hr. The mixture was filtered and the filtrate was washed with 100 ml of 5% sodium bicarbonate, dried over sodium sulfate, and concentrated to give a solid as residue. The solid was recrystallized from 2-propanol to give 12.9 g (71%) predominantly the title compound as a tan solid. A reference sample, m.p. 127°-128° C. was recrystallized thrice from 2-propanol, but a satisfactory analysis could not be obtained. A TLC of the solid showed one spot and the H1 and C13NMR and mass spectrum were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under illumination by a flood lamp for 2.5 hr
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with 100 ml of 5% sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a solid as residue
  8. customThe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-7f720911e7f646e4a4a57b5efd422c17
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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