Azobisisobutyronitrile → HCID 131720860, compound

HRID 399000Notes

Reaction equation

HRID 399000 reaction equation
[CH3:1][O:2][N:3]=[C:4]([O:13][CH3:14])[C:5](=[O:12])[C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH3:11].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]([O:13][CH3:14])[C:5](=[O:12])[C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH2:11][Br:15]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 131720861HCID 131720861, compound

Product 1

HCID 131720860HCID 131720860, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 106 g (0.5 mol) of the methylthiazol (cis-isomer from Example 3 c), 100 g (0.56 mol) of N-bromosuccinimide and 1 g of azobisisobutyronitrile in 1 l of carbon tetrachloride is refluxed for 3 hours. 20 g (0.11 mol) of N-bromosuccinimide are also added and heating is carried out for a further 2 hours. The reaction mixture is cooled to room temperature and the precipitated succinimide is filtered off under suction. The filtrate is extracted with water, dried over MgSO4 and evaporated down. The residue is purified by column chromatography using hexane/ethyl acetate mixtures. The products brominated in the nucleus and polybrominated products are obtained in the first fraction, followed by 58 g of the cis-isomer (about 90% purity; 0.18 mol, 36%) and 11 g of the trans-isomer (about 90% purity, 34 mmol, 7%) of the title compound as yellow oils.

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureheating
  3. filtrationthe precipitated succinimide is filtered off under suction
  4. extractionThe filtrate is extracted with water
  5. dry with materialdried over MgSO4
  6. customevaporated down
  7. customThe residue is purified by column chromatography
  8. customare obtained in the first fraction

Sources & evidence

ORD record
ord-afd89a0430a0411eab1146de3ef0083c
Source dataset
uspto-grants-1998_10
Patent number
US05817682

Reaction notes

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