1H-1,2,4-Triazole → 1-[2-(3-thienyl)ethyl]-1H-1,2,4-triazole

HRID 234612Notes

Reaction equation

HRID 234612 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)(=O)=O.[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[S:10]1[CH:11]=[CH:12][C:8]([CH2:7][CH2:6][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)=[CH:9]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 144229343-Thiopheneethanol methanesulfonate

Product 1

HCID 233550351-[2-(3-thienyl)ethyl]-1H-1,2,4-triazoleYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-thiopheneethanol methanesulfonate (ester) (0.286 mol), 1,2,4-triazole (0.571 mol) and potassium carbonate (39.47 g) in acetonitrile (1100 ml) was refluxed overnight. The mixture was filtered off and the filtrate was evaporated. The residue was taken up in water and extracted with dichloromethane. The organic layer was dried (MgSO4), filtered off and evaporated. The residue (49.08 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 99/1/0.1 to 97/3/0.1) (35-70 μm). The pure fractions were collected and evaporated, yielding 42.4 g (83%) of 1-[2-(3-thienyl)ethyl]-1H-1,2,4-triazole (interm. 1).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture was filtered off
  3. customthe filtrate was evaporated
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered off
  7. customevaporated
  8. customThe residue (49.08 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 99/1/0.1 to 97/3/0.1) (35-70 μm)
  9. customThe pure fractions were collected
  10. customevaporated

Sources & evidence

ORD record
ord-9e44bb29f7de428c9f6309dca0040faf
Source dataset
uspto-grants-1997_01
Patent number
US05595988

Reaction notes

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