Sodium Azide → HCID 178426257, compound

HRID 1112529Notes

Reaction equation

HRID 1112529 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[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=1)[C:12](OCC)=[O:13])#[N:10]>O1CCCC1>[CH3:25][C:24]1[C:19]2=[N:18][CH:17]=[C:11]([C:9]3[NH:10][N:7]=[N:6][N:5]=3)[C:12](=[O:13])[N:20]2[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 3673519HCID 3673519, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178426257HCID 178426257, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (3.51 g., 0.0263 mole) was added to cold (-30°) tetrahydrofuran (180 ml.). Sodium azide (5.12 g., 0.0788 mole) was added and the mixture heated under reflux for 30 minutes. The mixture was cooled to 5°. Ethyl 2-cyano-3-(3-methyl-2-pyridylamino)acrylate (5.0 g., 0.0216 mole) was added and the mixture heated under reflux for 18 hours. The tetrahydrofuran was removed under reduced pressure. The residue was treated with ice water (100 ml.) and acidified to pH 3 with 6N hydrochloric acid. The mixture was filtered and the collected solid recrystallized from N,N-dimethylformamide to give the title compound (2.5 g., 50.7%), m.p. 310°-311° (decomp).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureThe mixture was cooled to 5°
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 18 hours
  6. customThe tetrahydrofuran was removed under reduced pressure
  7. additionThe residue was treated with ice water (100 ml.)
  8. filtrationThe mixture was filtered
  9. customthe collected solid recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-dafe21e0e1504e22a940172d35ad4154
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

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