N-bromobutanimide → HCID 15634755, compound

HRID 1198990Notes

Reaction equation

HRID 1198990 reaction equation
[CH3:1][C:2]1[C:10]2[C:6](=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[C:10]2[C:6](=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15634753HCID 15634753, compound

Product 1

HCID 15634755HCID 15634755, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 23.5 g (0.112 mole) of 7-methyl-3-phenyl-2,1-benzisoxazole in 400 ml of carbon tetrachloride was treated with 20.0 g (0.112 mole) of N-bromosuccinimide and the mixture was heated at reflux with a white light lamp until all solid floated in the solvent. The mixture was filtered and the filtrate deposited a 15 g crop of reasonably pure product. This 15 g of material was dissolved in methylene chloride and washed with diluted sodium hydroxide to remove succinimide. The organic solution was concentrated and the residue was crystallized from isopropanol to give 25.2 g (77%) of yellow needles, m.p. 125.0°-125.5° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux with a white light lamp until all solid
  3. filtrationThe mixture was filtered
  4. dissolutionThis 15 g of material was dissolved in methylene chloride
  5. washwashed with diluted sodium hydroxide
  6. customto remove succinimide
  7. concentrationThe organic solution was concentrated
  8. customthe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-406c1f508c884f3db9ff796767ede73a
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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