Benzoyl Peroxide → HCID 53875814, compound

HRID 981892Notes

Reaction equation

HRID 981892 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][N:28]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[C:29](=[O:42])[C:30]([CH3:41])=[CH:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1>C(Cl)(Cl)(Cl)Cl>[CH3:27][N:28]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[C:29](=[O:42])[C:30]([CH2:41][Br:1])=[CH:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 54009953HCID 54009953, compound

Product 1

HCID 53875814HCID 53875814, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

18 g of N-bromosuccinic acid imide and 0.5 g of benzoyl peroxide were added to a solution of 47 g of N-methyl-N-octadecyl-α-methyl-4-nitrocinnamic acid amide in 400 ml of carbon tetrachloride. The mixture was gradually heated from room temperature under reflux for about 1 hour. The mixture was heated under reflux for 10 hours while being irradiated with light from an incandescent lamp, and then allowed to cool. After the solvent was distilled off under reduced pressure, the residue was then subjected to silica gel column chromatography. The desired substance was obtained from a fraction extracted with a 1:2 mixture of hexane and ethyl acetate. (Yield: 23 g (42%))

Workup

  1. temperatureunder reflux for about 1 hour
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 10 hours
  4. customwhile being irradiated with light from an incandescent lamp
  5. temperatureto cool
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. customThe desired substance was obtained from a fraction
  8. extractionextracted with a 1:2 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-5e30e744c4094f60999fdf4c15370b6e
Source dataset
uspto-grants-1991_02
Patent number
US04994363

Reaction notes

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