Azobisisobutyronitrile → HCID 59296122, compound

HRID 2263385Notes

Reaction equation

HRID 2263385 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:32]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH2:19][Br:32])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59296132HCID 59296132, compound

Product 1

HCID 59296122HCID 59296122, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a boiling solution of 23.5 g 2-(4-methoxy-phenyl)-4-methyl-oxazole-5-carboxylic acid ethyl ester in 250 ml tetrachloro-methane were added portionwise a mixture of 5.92 g 2,2′-azobis(2-methylpropionitrile) and 19.3 g N-bromosuccinimide. The reaction mixture was refluxed for seven hours. The cooled reaction mixture was filtered over a celite pad and the solvent removed in vacuo to obtain 30.7 g of crude 4-bromomethyl-2-(4-methoxy-phenyl)-oxazole-5-carboxylic acid ethyl ester. The material was used without further purification in the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for seven hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered over a celite pad
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-fb22e8f7342b40719f2fe435c50f7ecd
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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