Hydrochloric Acid → 2-Amino-5H-s-triazolo[5,1-a]isoindole

HRID 436193Notes

Reaction equation

HRID 436193 reaction equation
Cl.[N:2]#[C:3][NH2:4].[NH2:5][C:6]([NH2:8])=N.[H-].[Na+].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[NH2:2][C:3]1[N:8]=[C:6]2[C:12]3[C:11]([CH2:17][N:5]2[N:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 1140TolueneHCID 3520GuanidineHCID 9864CyanamideHCID 24758Sodium hydride

Product 1

HCID 214553042-Amino-5H-s-triazolo[5,1-a]isoindoleYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26.2 g of N-aminophthalimidine hydrochloride (0.142 mole) and 6.25 g of cyanamide (0.149 mole) in 270 ml of anhydrous toluene are refluxed for two hours then, after cooling, the resulting solid precipitate is recovered by filtration. Yield, 31 g of the hydrochloride of 1-(2-phthalimidinyl)- guanidine. M.p. 269-70°C. An amount of 7.6 g (0.033 mole) of this latter compound is added to a solution of 1.5 g of 80% sodium hydride (0.05 mole) in 90 ml of ethanol and the mixture is refluxed for five hours. The solvent is distilled off in vacuo and the solid residue is taken up with water and the pH of the mixture is brought to 7 by addition of acetic acid. Extraction with dichloromethane and evaporation of the organic phase yields 4.5 g (78%) of the title product. M.p. 193-4°C (from ethanol).

Workup

  1. temperatureare refluxed for two hours
  2. temperatureafter cooling
  3. filtrationthe resulting solid precipitate is recovered by filtration
  4. customYield
  5. temperaturethe mixture is refluxed for five hours
  6. distillationThe solvent is distilled off in vacuo
  7. additionthe pH of the mixture is brought to 7 by addition of acetic acid
  8. extractionExtraction
  9. customwith dichloromethane and evaporation of the organic phase

Sources & evidence

ORD record
ord-eb795b68a19648d68ddfe2e39676f75f
Source dataset
uspto-grants-1977_02
Patent number
US04007276

Reaction notes

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