Hydrochloric Acid → HCID 178436511, compound

HRID 1112530Notes

Reaction equation

HRID 1112530 reaction equation
[C:1]([C:3](=[CH:9][NH:10][C:11]1[C:16]([CH2:17][CH3:18])=[CH:15][CH:14]=[CH:13][N:12]=1)[C:4](OCC)=[O:5])#[N:2].[N-:19]=[N+:20]=[N-:21].[Al+3].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[Cl-].[Al+3].[Cl-].[Cl-].[N-]=[N+]=[N-].[Na+].Cl>O1CCCC1.O>[CH2:17]([C:16]1[C:11]2=[N:10][CH:9]=[C:3]([C:1]3[NH:2][N:21]=[N:20][N:19]=3)[C:4](=[O:5])[N:12]2[CH:13]=[CH:14][CH:15]=1)[CH3:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 21652180Aluminum azide2×HCID 70593218Ethyl 2-cyano-3-(3-ethyl-2-pyridylamino)acrylate

Product 1

HCID 178436511HCID 178436511, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 2-cyano-3-(3-ethyl-2-pyridylamino)acrylate (10.0 g., 0.0408 mole) was added to a stirred mixture of aluminum azide in tetrahydrofuran at 0°. The aluminum azide had been prepared in situ in the usual manner from aluminum chloride (6.5 g., 0.0488 mole) and sodium azide (9.5 g., 0.1464 mole) in tetrahydrofuran (100 ml.). The mixture was stirred at 0° for 15 minutes and then heated under reflux for 19 hours. The mixture was cooled, diluted with water, and acidified with concentrated hydrochloric acid (20 ml.). The mixture was filtered to give the title compound (2.7 g., 27%), m.p. 285°-288°. The product was recrystallized from N,N-dimethylformamide with charcoal treatment to give analytical material, m.p. 288°-290° (decomp).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 19 hours
  3. temperatureThe mixture was cooled
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-35feb3a5bedd4e79bc4aedfc2667e69b
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

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