N-bromobutanimide → HCID 14098280, compound

HRID 648452Notes

Reaction equation

HRID 648452 reaction equation
[CH3:1][C:2]1[C:7]2=[CH:8][O:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:1][C:2]1[C:7]2=[CH:8][O:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 140982794-Methyl-2,1-benzisoxazole

Product 1

HCID 14098280HCID 14098280, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5.99 g (45.0 mmoles) (1) in 135 ml carbon tetrachloride was added 8.81 g (49.5 mmoles) N-bromosuccinimide and 100 mg benzoyl peroxide. The mixture was refluxed while illuminated by a 250 watt sunlamp for 18 hours. The mixture was cooled and filtered, and the filtrate concentrated to give 9.9 g of a dark red oil. The oil was extracted with 500 ml hot hexane. The hexane solution was evaporated to 150 ml and cooled to give 6.60 g (69%) of crystalline (2), m.p. 51.0°-52.5°; nmr (deuteriochloroform): 4.6 (s, 2H), 7.2 (m, 3H), 9.3 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed
  2. customwhile illuminated by a 250 watt sunlamp for 18 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-9d1f1dedd6d04defa980660a38e4c218
Source dataset
uspto-grants-1988_04
Patent number
US04735956

Reaction notes

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