Azobisisobutyronitrile → HCID 66639400, compound

HRID 1094458Notes

Reaction equation

HRID 1094458 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[CH3:19])[CH3:10].CC(N=NC(C#N)(C)C)(C#N)C.C(=O)(O)[O-].[Na+].[C:38]1([P:44]([C:51]2C=CC=CC=2)[C:45]2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Br-:1].[CH2:9]([O:11][C:12]([C:13]1[C:14]([CH2:19][P+:44]([CH3:51])([CH3:45])[CH3:38])=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:20])[CH3:10]

Participants

8

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 74401Ethyl 2-methylnicotinateHCID 516892Sodium Bicarbonate

Product 1

HCID 66639400HCID 66639400, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred mixture of N-bromosuccinimide (5.6 g, 31 mmol), 2-Methyl-nicotinic acid ethyl ester (4.1 g, 24 mmol), AIBN (0.05 g, 0.3 mmol) in 50 mL of carbon tetrachloride at 50° C. is irradiated with a 250 Watt heat lamp for 45 minutes. The reaction was cooled to room temperature and is poured into saturated sodium bicarbonate. The products are extracted into dichloromethane and the combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a residue which is immediately dissolved in 100 mL of toluene. To the solution is added triphenyl phosphine (8.1 g, 31 mmol) and the reaction is heated at reflux for 2 hours. The heat source is removed and filtration gives the title compound.

Workup

  1. customis irradiated with a 250 Watt
  2. temperatureheat lamp for 45 minutes
  3. extractionThe products are extracted into dichloromethane
  4. dry with materialthe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a residue which
  8. temperaturethe reaction is heated
  9. temperatureat reflux for 2 hours
  10. customThe heat source is removed
  11. filtrationfiltration

Sources & evidence

ORD record
ord-ad3b1dd3751946059368b868493bf04b
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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