Hydrochloric Acid → HCID 178515422, compound

HRID 1112521Notes

Reaction equation

HRID 1112521 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][CH:22]=[CH:21][N:20]=1)[C:12](OCC)=[O:13])#[N:10].Cl>O.O1CCCC1>[NH:5]1[C:9]([C:11]2[C:12](=[O:13])[N:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][CH:17]=2)=[N:10][N:7]=[N:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 728730Ethyl 2-cyano-3-(2-pyridylamino)acrylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178515422HCID 178515422, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (0.74 g., 5.56 mmoles) was carefully added to tetrahydrofuran (33 ml.) at -20°. Sodium azide (1.08 g., 16.6 mmoles) was then added and the mixture heated under reflux for 30 minutes. After the addition of ethyl 2-cyano-3-(2-pyridylamino)acrylate (1.0 g., 4.6 mmoles) the mixture was again heated under reflux for 18 hours. The mixture was cooled in an ice bath, treated with water (170 ml.) and acidified to pH 2 with 6N hydrochloric acid. The resulting suspension was stirred with cooling for 2 hours and then filtered. The collected solid was recrystallized from N,N-dimethylformamide to give the title compound (0.38 g., 38.5%), m.p. 308°-309° (decomp).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturewas again heated
  4. temperatureunder reflux for 18 hours
  5. temperatureThe mixture was cooled in an ice bath
  6. temperaturewith cooling for 2 hours
  7. filtrationfiltered
  8. customThe collected solid was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-bc6aa2ef044b43d298d8ab06fb3b7b6c
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

Loading…