Hydrochloric Acid → HCID 178515421, compound

HRID 1112528Notes

Reaction equation

HRID 1112528 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:22]=1)[C:15](=[O:21])[C:16]([C:19]#[N:20])=[CH:17][N:18]=2.Cl>O1CCCC1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:22]=1)[C:15](=[O:21])[C:16]([C:19]1[NH:20][N:7]=[N:6][N:5]=1)=[CH:17][N:18]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 22764385HCID 22764385, compound

Product 1

HCID 178515421HCID 178515421, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (0.72 g., 5.45 mmoles) was carefully added to cold (-30°) tetrahydrofuran (29 ml.). Sodium azide (1.06 g., 16.27 mmoles) was then added and the mixture heated under reflux for 30 minutes. 7-Chloro-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbonitrile (1.0 g., 4.47 mmoles) was added and the mixture heated under reflux for 18 hours. The cooled mixture was poured onto 500 ml. of ice water and the resulting mixture acidified to pH 2 with 6N hydrochloric acid. The precipitate was collected and recrystallized from N,N-dimethylformamide to give the title compound (0.55 g., 49.5%), m.p. 300°-301° (decomp).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 18 hours
  5. additionThe cooled mixture was poured onto 500 ml
  6. customThe precipitate was collected
  7. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-d923efc0411c49499711f381e42511e5
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

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