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

HRID 735348Notes

Reaction equation

HRID 735348 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[I:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]Br.C1CCN2C(=NCCC2)CC1>C1COCC1>[I:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 114264722-Iodobenzyl Bromide

Product 1

HCID 185258171-(2-Iodobenzyl)-1H-1,2,4-triazoleYield 34.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of 1,2,4-triazole (1.02 g, 14.8 mmol) and 2-iodobenzyl bromide (6.05 g, 20.3 mmol) in THF (10 mL) was added a solution of DBU (2.65 g, 17.4 mmol) in THF (2 mL) dropwise over a 1 hour period. The mixture was stirred at ambient temperature for 12 hours after which it was filtered. The filtrate was concentrated in vacuo and the resultant residue was dissolved in ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 50-60% ethyl acetate/isohexane to give the title compound as a white solid (1.45 g). 1H NMR (360 MHz, CDCl3): δ 8.15 (1H, s), 8.00 (1H, s), 7.89 (1H, d, J=7.9 Hz), 7.36 (1H, t, J=7.6 Hz), 7.13 (1H, d, J=7.7 Hz), 7.08-7.04 (1H, m), 5.43 (2H, s).

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe resultant residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with 50-60% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-d72e8f7f85484a4ea444c76be209ba12
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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