Hydrochloric Acid → HCID 178518585, compound

HRID 261214Notes

Reaction equation

HRID 261214 reaction equation
[O:1]=[C:2]1[N:11]2[N:12]=[C:13]([C:15]#[N:16])[CH:14]=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O.O>[NH:17]1[C:15]([C:13]2[CH:14]=[C:10]3[N:11]([C:2](=[O:1])[NH:3][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=43)[N:12]=2)=[N:16][N:19]=[N:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 1357356215,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carbonitrile

Product 1

HCID 178518585HCID 178518585, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.6 g (0.0076 mole) of 5,6-dihydro-5-oxopyrazolo[1,5-c]-quinazoline-2-carbonitrile (prepared as described in Example 2), 546 mg of sodium azide (0.0084 mole or 1.1 equivalent) and 449 mg (1.1 equivalent) of ammonium chloride are suspended in dimethylformamide (30 ml) and the mixture is heated at 100° under N2 for 29 hours with stirring. The reaction mixture is cooled and stripped to dryness. The crude product is suspended in water (75 ml) and treated with concentrated HCl (1.5 ml) to pH 2. The mixture is stirred for ~15 minutes and filtered; the precipitates obtained are washed well with water and air-dried to yield: 2.17 g, quantitative crude yield, m.p. 287°-289°.

Workup

  1. temperaturethe mixture is heated at 100° under N2 for 29 hours
  2. temperatureThe reaction mixture is cooled
  3. stirringThe mixture is stirred for ~15 minutes
  4. filtrationfiltered
  5. customthe precipitates obtained
  6. washare washed well with water
  7. customair-dried to yield: 2.17 g, quantitative crude
  8. customyield

Sources & evidence

ORD record
ord-6a4937bd568c401cbf4d765320664d61
Source dataset
uspto-grants-1979_08
Patent number
US04164578

Reaction notes

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