N-bromobutanimide → HCID 14835340, compound

HRID 1198976Notes

Reaction equation

HRID 1198976 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][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:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13113647HCID 13113647, compound

Product 1

HCID 14835340HCID 14835340, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 14.9 g (0.071 mole) of 3-(4'-methylphenyl)-2,1-benzisoxazole, 12.7 g (0.071 mole) of N-bromosuccinimide, 0.1 g of dibenzoyl peroxide and 200 ml of carbon tetrachloride was heated at reflux under illumination by a flood lamp for 20 hr. The mixture was filtered while hot and the filtrate was washed twice with 5% aqueous sodium hydroxide, dried over sodium sulfate and concentrated. The residue was dissolved in acetonitrile and filtered to remove insoluble material. The filtrate was concentrated and the residue was recrystallized twice from ethanol and once from 2-propanol (charcoal) to yield 12.1 g (59%) of solid, m.p. 146°-147° C. with decomposition.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under illumination by a flood lamp for 20 hr
  3. filtrationThe mixture was filtered while hot and the filtrate
  4. washwas washed twice with 5% aqueous sodium hydroxide
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in acetonitrile
  8. filtrationfiltered
  9. customto remove insoluble material
  10. concentrationThe filtrate was concentrated
  11. customthe residue was recrystallized twice from ethanol and once from 2-propanol (charcoal)

Sources & evidence

ORD record
ord-562240c7aace4162aa1aac44daba38be
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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