Sodium Azide → HCID 178440676, compound

HRID 1112526Notes

Reaction equation

HRID 1112526 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[C:9]([C:11](=[CH:17][NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH3:28])=[CH:21][N:20]=1)[C:12](OCC)=[O:13])#[N:10]>O1CCCC1>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]2[N:20]([CH:21]=1)[C:12](=[O:13])[C:11]([C:9]1[NH:10][N:7]=[N:6][N:5]=1)=[CH:17][N:18]=2)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 70514903Ethyl 2-cyano-3-(5-n-butyl-2-pyridylamino)acrylate

Product 1

HCID 178440676HCID 178440676, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (0.89 g., 6.67 mmoles was carefully added to cold (-30°) tetrahydrofuran (42 ml.). Sodium azide (1.3 g., 20.0 mmoles was then added and the mixture heated at reflux for 40 minutes. Ethyl 2-cyano-3-(5-n-butyl-2-pyridylamino)acrylate (1.50 g., 5.49 mmoles) was added and the mixture heated under reflux for 18 hours. The cooled mixture was concentrated and the residue treated with ice water (50 ml.). The mixture was acidified to pH 3 with 6N hydrochloric acid. The mixture was filtered and the collected solid treated with boiling 3% aqueous sodium bicarbonate for 10 minutes. The mixture was filtered and the filtrate acidified to pH 4 with 6N hydrochloric acid. The precipitate was recrystallized from N,N-dimethylformamide to give the title compound (0.45 g., 30.4%), m.p. 284°-285° (decomp).

Workup

  1. addition, 20.0 mmoles was then added
  2. temperaturethe mixture heated
  3. temperatureat reflux for 40 minutes
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 18 hours
  6. concentrationThe cooled mixture was concentrated
  7. additionthe residue treated with ice water (50 ml.)
  8. filtrationThe mixture was filtered
  9. additionthe collected solid treated
  10. customfor 10 minutes
  11. filtrationThe mixture was filtered
  12. customThe precipitate was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-6ac368ac13af45489119d558d1b2b79a
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

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