Tetrahydrofuran → Ethyl 4-(4H-1,2,4-triazol-4-yl)benzoate

HRID 278559Notes

Reaction equation

HRID 278559 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=2)[CH:5]=1.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1.[OH-:22].[Na+]>C(O)C>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[CH:8][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=2)[CH:5]=1.[NH:4]1[CH:6]=[C:7]([C:8]2[CH:9]=[CH:15][C:18]([C:19]([OH:22])=[O:20])=[CH:17][CH:21]=2)[N:1]=[CH:5]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22627983Ethyl 4-(4H-1,2,4-triazol-4-yl)benzoate

Product 2

HCID 22627983Ethyl 4-(4H-1,2,4-triazol-4-yl)benzoateHCID 178524222HCID 178524222, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the obtained ethyl 4-(1,2,4-triazol-4-yl)benzoate (365 mg) in ethanol (4 ml)-THF (4 ml) was added 1 N sodium hydroxide solution (4 ml), and the solution was stirred at room temperature for 2 hours. The reaction solution was concentrated and the residue was dissolved in water, to which was added 1 N hydrochloric acid (4 ml). The precipitate was filtered, washed with water and dried to give the title compound, 4-(1H-imidazol-4-yl)benzoic acid (275 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in water, to which
  3. additionwas added 1 N hydrochloric acid (4 ml)
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-88c28893c9594e7a9782997779a71a98
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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