Iodine → 3-(3-iodo-4-methoxybenzyl)-1H-1,2,4-triazole

HRID 1508549Notes

Reaction equation

HRID 1508549 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[CH:5][CH:4]=1.[I:15]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:15][C:14]1[CH:13]=[C:6]([CH:5]=[CH:4][C:3]=1[O:2][CH3:1])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][N:9]=1

Participants

5

Reactant 2

HCID 807IodineHCID 178489902HCID 178489902, compound

Product 1

HCID 1784899043-(3-iodo-4-methoxybenzyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-methoxybenzyl)-1H-1,2,4-triazole (335 mg, 1.770 mmol) in MeOH (5 ml) under nitrogen at RT was added silver sulfate (552 mg, 1.770 mmol) followed by iodine (449 mg, 1.770 mmol). Added a second equivalent of silver sulfate and stirred for 3 days. The reaction did not go to completion. The solids were filtered washing with MeOH, the filtrate was concentrated, and the residue was purified by flash column chromatography on silica gel, eluting with MeOH in DCM to afford the title compound contaminated with ca. 20% of starting material. Mass spectrum (ESI) 316.1 (M+1).

Workup

  1. filtrationThe solids were filtered
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by flash column chromatography on silica gel
  5. washeluting with MeOH in DCM

Sources & evidence

ORD record
ord-cfaa3d88e7654d019e04623a8f363db9
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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