Benzoyl Peroxide → HCID 22116003, compound

HRID 1885633Notes

Reaction equation

HRID 1885633 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH:10]([CH2:12][O:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)[CH2:9][C:8]2=[O:24])=[CH:3][CH:2]=1.[Br:26]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:25][C:1]1[CH:2]=[CH:3][C:4]([N:7]2[CH2:11][CH:10]([CH2:12][O:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=3)[CH2:9][C:8]2=[O:24])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10382557HCID 10382557, compound

Product 1

HCID 22116003HCID 22116003, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 4-[1-(4-tolyl)-2-pyrrolidon-4-yl]methoxybenzoate (3.00 g) and N-bromosuccinimide (1.81 g) are suspended in carbon tetrachloride (50 ml), and thereto is added benzoyl peroxide (0.21 g) and the mixture is stirred under refluxing for 5 hours. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethyl acetate (60 ml), washed successively with aqueous sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily product is subjected to silica gel column chromatography and eluted with a mixed solvent of chloroform/n-hexane [1:1 (v/v)]to give the desired product (2.10 g).

Workup

  1. temperatureunder refluxing for 5 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in ethyl acetate (60 ml)
  5. washwashed successively with aqueous sodium hydrogen carbonate solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted with a mixed solvent of chloroform/n-hexane [1:1 (v/v)]to

Sources & evidence

ORD record
ord-eb4f5d0355a14ca4bef9c0913030ec79
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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