Water → HCID 22629657, compound

HRID 277037Notes

Reaction equation

HRID 277037 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([CH2:12][C:13]#[N:14])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Br[C:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:22][C:23]#[N:24].O>O1CCCC1>[NH2:24][C:23]1[N:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[C:9]2[C:12]([C:13]#[N:14])=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4493413HCID 4493413, compoundHCID 178418339ButyllithiumHCID 178510899HCID 178510899, compound

Product 1

HCID 22629657HCID 22629657, compoundYield 1.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.18 g (0.001 mol) 5-phenyl-1H-1,2,4-triazole-3-acetonitrile in 7 ml tetrahydrofuran was treated at −70° C. with 1.56 ml (0.0025 mol) butyllithium (1.6 M in hexane). After one hour 0.21 g (0.001 mol) 3-bromo-3-phenyl-2-propenenitrile was added, stirring was continued for one hour, the mixture warmed to room temperature over night and water was added. Extraction with diethylether, chromatography on silicagel with dichloromethane/methanol 99/1 and crystallisation from diethylether gave 3.6 mg 5-amino-2,7-diphenyl-[1,2,4]triazolo[1,5-a]pyridine-8-carbonitril as white cystals. MS m/e (%): 312 (M+H+, 100).

Workup

  1. extractionExtraction with diethylether, chromatography on silicagel
  2. customwith dichloromethane/methanol 99/1 and crystallisation from diethylether

Sources & evidence

ORD record
ord-75734ec9a40f4d3f95d1eed13f84c796
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

Loading…