Chloroform → Methyl 3-(1H-1,2,4-triazol-1-YL)benzoate

HRID 962776Notes

Reaction equation

HRID 962776 reaction equation
[N:1]1[CH:6]=[N:5][CH:4]=[N:3][CH:2]=1.Cl.N([C:10]1[CH:11]=[C:12]([CH:17]=C[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])N.C(Cl)(Cl)Cl>C(O)C>[N:5]1([C:6]2[CH:17]=[C:12]([CH:11]=[CH:10][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:4]=[N:3][CH:2]=[N:1]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 92621,3,5-TriazineHCID 23285088Methyl 3-hydrazinylbenzoate hydrochloride

Product 1

HCID 22224836Methyl 3-(1H-1,2,4-triazol-1-YL)benzoateYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.04 g of 1,3,5-triazine was added to a solution of 3.7 g of methyl 3-hydrazinobenzoate hydrochloride in 20 ml of ethanol. The mixture was refluxed by heating, for 3 hours. The reaction mixture was allowed to cool and mixed with chloroform. The resulting insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: methylene chloride/methanol=100/0 to 100/1) and then subjected to crystallization from diisopropyl ether. The crystals were collected by filtration to obtain 2.0 g of methyl 3-(1,2,4-triazol-1-yl)benzoate as colorless needle-like crystals.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureby heating, for 3 hours
  3. temperatureto cool
  4. customThe resulting insolubles were removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluant: methylene chloride/methanol=100/0 to 100/1)
  7. customsubjected to crystallization from diisopropyl ether
  8. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-1867c2fd8a834a69885de7915d0307c5
Source dataset
uspto-grants-1998_06
Patent number
US05760058

Reaction notes

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