Sodium hydride → 5H-s-Triazolo(5,1-a)isoindole, 2-phenyl-

HRID 436201Notes

Reaction equation

HRID 436201 reaction equation
Br.[C:2]1([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:19]Br)[NH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>C(O)C>[C:2]1([C:8]2[N:12]=[C:11]3[C:13]4[C:14]([CH2:19][N:10]3[N:9]=2)=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86734484HCID 86734484, compound

Product 1

HCID 1344495H-s-Triazolo(5,1-a)isoindole, 2-phenyl-Yield 76.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Phenyl-5-(o-bromomethylphenyl)-s-triazole hydrobromide (41 g) is added to a solution of 6.55 g of 80% sodium hydride in 525 ml of ethanol at about 20° C. The obtained mixture is refluxed for about two hours, then the solvent is distilled off. The crude residue is extracted with 620 ml of benzene and the organic phase is evaporated, yielding 18.6 g of 2-phenyl-5H-s-triazolo[5,1-a]isoindole, which is purified by crystallization from ethanol. M.p. 156°-8° C. The starting compound 3-phenyl-5-(o-bromomethylphenyl)-s-triazole hydrobromide is obtained by evaporation of a solution of 3-phenyl-5-(o-hydroxymethylphenyl)-s-triazole in acetic acid saturated with hydrogen bromide. M.p. 193°-5° C.

Workup

  1. temperatureThe obtained mixture is refluxed for about two hours
  2. distillationthe solvent is distilled off
  3. extractionThe crude residue is extracted with 620 ml of benzene
  4. customthe organic phase is evaporated

Sources & evidence

ORD record
ord-642555fdac244434ab020d5af9678fed
Source dataset
uspto-grants-1977_02
Patent number
US04007276

Reaction notes

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