Hexane → 3-(3-Benzyloxy-benzyl)-1,2,4-triazole

HRID 902606

Reaction equation

HRID 902606 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[CH:18]([NH:20][NH2:21])=O.C(=O)([O-])[O-].[K+].[K+].[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][C:16]1[N:17]=[CH:18][NH:20][N:21]=1)[C:30]1[CH:29]=[CH:28][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 12229HydrazinecarboxaldehydeHCID 5198313-Benzyloxyphenylacetonitrile

Product 1

HCID 1784203933-(3-Benzyloxy-benzyl)-1,2,4-triazoleYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 3-benzyloxyphenylacetonitrile (5.0 g, 0.022 mole) in methanol (100 mL) was added formic hydrazide (2.69 g, 0.060 mole) and solid potassium carbonate (9.9 g, 0.027 mole). The reaction was heated at reflux and stirred overnight. The mixture was cooled to RT, filtered, and the filtrate was concentrated. The crude product was purified by column chromatography over silica gel (silica gel 60, EM Science) using 75% ethyl acetate:hexane as eluent to afford 1.8 g (30% yield) of the title compound as an oil: MS (ESI) 266.0 (M+H+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by column chromatography over silica gel (silica gel 60, EM Science)

Sources & evidence

ORD record
ord-d6d702fabbfb4a7ea1cf73e72427808a
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Linked notes

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