1H-1,2,4-Triazole → 1-(4-Nitrobenzyl)-1H-1,2,4-triazole

HRID 1446133Notes

Reaction equation

HRID 1446133 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 660114-Nitrobenzyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 64820001-(4-Nitrobenzyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 g (4.63 mmol) of 4-nitrobenzyl bromide (Fluka, Buchs, Switzerland), 799 mg (11.6 mmol) of 1,2,4-triazole and 0.692 mL (4.63 mmol) of 1,5-diazabicyclo[5.4.0]-5-undecene (Fluka, Buchs, Switzerland) in 10 ml of CH2Cl2 are stirred at rt for 1.5 h. The reaction mixture is quenched with sat. aqueous NaHCO3 and extracted with CH2Cl2 (2×). The organic layers are washed with brine, dried over MgSO4, filtered and evaporated. The residue is purified by flash chromatography (CH2Cl2-MeOH 49:1 to 19:1) to provide the title compound as a pale yellow solid. ES-MS: 205 (M+H)+; analytical HPLC: tret=2.54 minutes (Grad 1).

Workup

  1. customThe reaction mixture is quenched with sat. aqueous NaHCO3
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by flash chromatography (CH2Cl2-MeOH 49:1 to 19:1)

Sources & evidence

ORD record
ord-f598c16cae3d4e53b2a5f30c8a6929dd
Source dataset
uspto-grants-2010_02
Patent number
US07667039B2

Reaction notes

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