N-bromobutanimide → HCID 14835370, compound

HRID 1199000Notes

Reaction equation

HRID 1199000 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][N:11]=[C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=12.[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:17]1[C:12]2[C:13](=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[O:10][N:11]=2)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14835369HCID 14835369, compound

Product 1

HCID 14835370HCID 14835370, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 10.9 g (0.039 mole) of 3-(2,4-dichlorophenyl)-7-methyl-2,1-benzisoxazole, 7.1 g (0.040 mole) of N-bromosuccinimide, 0.1 g of dibenzoylperoxide and 200 ml of carbon tetrachloride was heated at reflux under illumination of a flood lamp for 2 hr. The mixture was filtered and the filtrate was washed once with a saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated to give a solid as residue. The solid was recrystallized from 2-propanol to yield 10.0 g (71%) of tan solid, m.p. 108°-110° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under illumination of a flood lamp for 2 hr
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed once with a saturated sodium bicarbonate solution
  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-70d470ea95644d95ad0f882f4f698cfc
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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