N-bromobutanimide → HCID 12562677, compound

HRID 1606012Notes

Reaction equation

HRID 1606012 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12562671HCID 12562671, compound

Product 1

HCID 12562677HCID 12562677, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-(4-Chlorophenyl)-5-methyl-1,2-benzisoxazole (12.2g.) and N-bromosuccinimide (9.6g.) were mixed in carbon tetrachloride (200ml.) and heated under reflux in the presence of UV light. (Hanovia medium pressure lamp 125 watts, emitting at 254,265,297,313,366 mp). On cooling, the mixture was filtered and the filtrate evaporated to dryness. The resulting solid was recrystallized from 33% toluene/60-80 petrol ether (150 ml.) to give the title compound as a white crystalline solid (10.0g) m.p. 142°C

Workup

  1. temperatureheated
  2. temperatureunder reflux in the presence of UV light
  3. temperatureOn cooling
  4. filtrationthe mixture was filtered
  5. customthe filtrate evaporated to dryness
  6. customThe resulting solid was recrystallized from 33% toluene/60-80 petrol ether (150 ml.)

Sources & evidence

ORD record
ord-d80fd0338cb04cbaa27ddab8fa560e9c
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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