N-bromobutanimide → HCID 14835344, compound

HRID 1198979Notes

Reaction equation

HRID 1198979 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)=[CH:5][CH:4]=1)[CH3:2].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14835343HCID 14835343, compound

Product 1

HCID 14835344HCID 14835344, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 24.5 g (0.11 mole) of 3-(4-ethylphenyl)-2,1-benzisoxazole in 330 ml of carbon tetrachloride was heated to reflux and treated with 19.6 g (0.11 mole) of N-bromosuccinimide and 10 mg of benzoyl peroxide. The mixture was maintained at reflux by illumination with a floodlamp for 20 min, at which time all insoluble material was floating. The mixture was cooled and filtered. The filtrate was washed with dilute sodium bicarbonate solution and the organic fraction was concentrated to a yellow solid. The solid was recrystallized from 200 ml of isopropanol to give 29.0 g (87%) of yellow crystals, m.p. 105.5°-8.0° C.

Workup

  1. temperatureto reflux
  2. temperatureThe mixture was maintained
  3. temperatureat reflux by illumination with a floodlamp for 20 min, at which time all insoluble material
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washThe filtrate was washed with dilute sodium bicarbonate solution
  7. concentrationthe organic fraction was concentrated to a yellow solid
  8. customThe solid was recrystallized from 200 ml of isopropanol

Sources & evidence

ORD record
ord-8a85fa80c2db4eaaa1afb8213627fd44
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

Loading…