Benzoyl Peroxide → HCID 59184674, compound

HRID 426110Notes

Reaction equation

HRID 426110 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:3]=1.[Cl:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:20][CH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 110649002-(4,6-Dimethyl-pyridin-2-yl)-isoindole-1,3-dione

Product 1

HCID 59184674HCID 59184674, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of (29) (2.52 g, 10 mmol)), N-chlorosuccinimide (1.6 g, 12 mmol), and benzoyl peroxide (1.21 g, 5 mmol) in carbon tetrachloride (50 ml) was refluxed for 2 hr. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, dichloromethane:EA (95:5)) to afford 493 mg (17%) of a yellow solid; 1H NMR (200 MHz, CDCl3) δ 2.63 (3H, s), 4.48 (2H, s), 7.27 (1H, s), 7.28 (1H, s), 7.76-7.98 (4H, m); m/z (EI) 286 (M+).

Workup

  1. temperaturewas refluxed for 2 hr
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluent, dichloromethane:EA (95:5))

Sources & evidence

ORD record
ord-f9e02db415ef41dd9e3ee4c561839cbc
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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