Azobisisobutyronitrile → HCID 68497857, compound

HRID 1712288Notes

Reaction equation

HRID 1712288 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])C.[Br:19]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:18][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([O:7][CH2:6][CH2:5][CH2:4][O:3][CH3:1])[CH:17]=1

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 68504307HCID 68504307, compound

Product 1

HCID 68497857HCID 68497857, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 25.0 g of methyl 2-(3-ethoxypropoxy)-4-methylbenzoate, 18.4 g of N-bromo-succinimide, 1.65 g of 2,2′-azobis(2-methylpropionitrile) and 2.46 g of dibenzoyl peroxide in 1.2 l of carbon tetrachloride is heated to reflux with stirring and stirred over 3 hours (succinimide crystallizes out). The reaction mixture is cooled and clarified by filtration, and the filtrate is concentrated by evaporation. The title compound is obtained as a slightly orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.30 (1:1 EtOAc-heptane); Rt=17.10 (II).

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. customcrystallizes out)
  4. temperatureThe reaction mixture is cooled
  5. filtrationclarified by filtration
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-e879852ef40e479181c76b619a719e1d
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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