N-bromobutanimide → HCID 14835378, compound

HRID 1199005Notes

Reaction equation

HRID 1199005 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]2[C:6]([CH:17]=1)=[C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[O:8][N:9]=2.[Br:19]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:18][C:4]1[C:5]2[C:6](=[C:7]([C:10]3[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=3)[O:8][N:9]=2)[CH:17]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14835377HCID 14835377, compound

Product 1

HCID 14835378HCID 14835378, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 12.2 g (0.044 mole) of 5-chloro-3-(4-chlorophenyl)-7-methyl-2,1-benzisoxazole, 8.0 g (0.045 mole) of N-bromosuccinimide, 0.1 g of dibenzoylperoxide and 500 ml of carbon tetrachloride was heated at reflux under white light illumination for 2 hr. The hot mixture was filtered and the filtrate was washed once with sodium bicarbonate solution, dried (sodium sulfate) and concentrated to give a solid as residue. The solid was recrystallized from acetonitrile to give 12.8 g (81%) of crude product. A portion of the solid was chromatographed on silica gel. The purified product was recrystallized from acetonitrile to yield an analytical sample of pale yellow solid, m.p. 145°-147° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under white light illumination for 2 hr
  3. filtrationThe hot mixture was filtered
  4. washthe filtrate was washed once with sodium bicarbonate solution
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customto give a solid as residue
  8. customThe solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5c5a7eaaab35425499f045edc68211dd
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

Loading…