Water → HCID 86711882, compound

HRID 1475191Notes

Reaction equation

HRID 1475191 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([NH:14][NH2:15])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:17](N)(=[NH:19])[CH3:18].[OH-].[Na+].O>C1COCC1>[CH3:18][C:17]1[NH:15][N:14]=[C:12]([C:10]2[O:11][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=2)[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 5149609HCID 5149609, compound

Product 1

HCID 86711882HCID 86711882, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-phenylfuran-2-carbohydrazide (100 mg, 0.5 mmol) and acetamidine hydrochloride (141 mg, 1.49 mmol) in THF (20 mL), NaOH (59 mg, 1.49 mmol) was added. The mixture was refluxed overnight, cooled, then treated with H2O (30 ml) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with H2O (1×10 mL) and brine (1×10 mL), dried over Na2SO4, filtered, concentrated under reduced pressure and purified by silica gel column chromatography (EtOAc:Petroleum ether=1:1) to afford 5-methyl-3-(5-phenylfuran-2-yl)-1H-1,2,4-triazole as a white solid (15 mg, 13%). MS (ES+) C13H11N3O requires: 225. found: 226 [M+H]+.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed overnight
  3. temperaturecooled
  4. extractionextracted with EtOAc (3×20 mL)
  5. washThe combined organic layers were washed with H2O (1×10 mL) and brine (1×10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. custompurified by silica gel column chromatography (EtOAc:Petroleum ether=1:1)

Sources & evidence

ORD record
ord-27e41cac0b4a4809b3ddf3047417fb0d
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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