Azobisisobutyronitrile → HCID 18412419, compound

HRID 2227679Notes

Reaction equation

HRID 2227679 reaction equation
[C:1]1([N:7]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](C(OC(C)(C)C)=O)[C:14]([CH3:26])=[CH:13]3)=[O:9])[CH:6]=CC=[CH:3][CH:2]=1.BrN1C(=O)C[CH2:36][C:35]1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[NH2:53][C:54]1[CH:61]=[CH:60][C:57]([C:58]#[N:59])=[CH:56][CH:55]=1>C(Cl)(Cl)(Cl)Cl>[C:1]1([N:7]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH2:26][NH:53][C:54]2[CH:61]=[CH:60][C:57]([C:58]#[N:59])=[CH:56][CH:55]=2)=[CH:13]3)=[O:9])[CH:2]=[CH:3][CH:36]=[CH:35][CH:6]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 133964-AminobenzonitrileHCID 67184N-bromobutanimideHCID 18412597HCID 18412597, compound

Product 1

HCID 18412419HCID 18412419, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3.5 g (8 mmol) of 1-tert-butoxycarbonyl-2-methylindol-5-yl-carboxylic acid-N-phenyl-N-(2-methoxycarbonylethyl)amide were dissolved in 80 ml of carbon tetrachloride, mixed with 1.5 g (8.4 mmol) of N-bromosuccinimide and 20 mg of azobisisobutyronitrile and refluxed for 2.5 hours. Then the still warm solution was filtered, the filtrate obtained was washed with saturated sodium hydrogen carbonate solution and dried with sodium sulfate. After distillation of the solvent, the crude product was dissolved in 30 ml of N-ethyldiisopropylamine, mixed with 1.0 g (8 mmol) of 4-aminobenzonitrile and refluxed for 2.5 hours. The solvent was distilled off in vacuo and the residue obtained was purified by chromatography (silica gel; ethyl acetate/petroleum ether=1:4 to

Workup

  1. temperaturerefluxed for 2.5 hours
  2. filtrationThen the still warm solution was filtered
  3. customthe filtrate obtained
  4. washwas washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried with sodium sulfate
  6. distillationAfter distillation of the solvent
  7. dissolutionthe crude product was dissolved in 30 ml of N-ethyldiisopropylamine
  8. temperaturerefluxed for 2.5 hours
  9. distillationThe solvent was distilled off in vacuo
  10. customthe residue obtained
  11. customwas purified by chromatography (silica gel

Sources & evidence

ORD record
ord-daae511aa360464dadf4ec6d0779abb2
Source dataset
uspto-grants-2002_07
Patent number
US06414008B1

Reaction notes

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