HCID 21491294, compound → HCID 178422305, compound

HRID 1973368Notes

Reaction equation

HRID 1973368 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([OH:16])=O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([CH3:12])=[C:7]([CH3:13])[CH:6]=2.[NH2:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1>O1CCCC1.CN(C)C=O>[Cl:1][C:2]1[C:3]([C:14]([NH:17][C:18]2[NH:22][N:21]=[N:20][N:19]=2)=[O:16])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([CH3:12])=[C:7]([CH3:13])[CH:6]=2

Participants

5

Reactant 2

HCID 21491294HCID 21491294, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178422305HCID 178422305, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-6,7-dimethyl-2quinoxalinecarboxylic acid (10.5 g) and N,N'-carbonyldiimidazole (7.35 g) in tetrahydrofuran (350 ml) were heated under reflux for 1 hour. 5-Amino-1H-tetrazole (4.3 g) in dimethylformamide (10 ml) was added and the mixture was heated under reflux for a further hour and cooled. The solid was collected and dissolved in aqueous dimethylaminoethanol. Dilute hydrochloric acid was added to the solution and the solid was collected and crystallised from dimethylformamide. The product decomposed at 360° (39%).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for a further hour
  4. temperaturecooled
  5. customThe solid was collected
  6. dissolutiondissolved in aqueous dimethylaminoethanol
  7. additionDilute hydrochloric acid was added to the solution
  8. customthe solid was collected
  9. customcrystallised from dimethylformamide
  10. customdecomposed at 360°

Sources & evidence

ORD record
ord-af24bc21495a4f8fa8a9d2b67293a793
Source dataset
uspto-grants-1976_12
Patent number
US03997535

Reaction notes

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