Acetic Acid → 5-Ethoxy-3-(3-iodophenyl)-1H-1,2,4-triazole

HRID 1372475Notes

Reaction equation

HRID 1372475 reaction equation
[NH2:1][N:2]1[CH2:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=2)O1.[OH-].[K+].[C:16](O)(=[O:18])[CH3:17]>C(O)C>[CH2:16]([O:18][C:6]1[NH:2][N:1]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=2)[N:5]=1)[CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 69373404HCID 69373404, compound

Product 1

HCID 1784673965-Ethoxy-3-(3-iodophenyl)-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product (1.00 g, 3.48 mmol) from Step A was added to a solution of potassium hydroxide (1.0 g) in 30 mL of absolute ethanol. The mixture was warmed to reflux and, after 5 h, cooled to room temperature. The solution was then acidified with glacial acetic acid, and concentrated under reduced pressure. The product was extracted into ethyl acetate, and the combined ethyl acetate extracts were washed sequentially with water and saturated aqueous brine, dried (magnesium sulfate) and concentrated to give the crude product as an orange semisolid. Purification by flash chromatography (silica gel, 15% ethyl acetate-hexanes) afforded the product as an off-white, sticky foam. LC/MS 316.0 (M+1).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux and, after 5 h
  3. concentrationconcentrated under reduced pressure
  4. extractionThe product was extracted into ethyl acetate
  5. washthe combined ethyl acetate extracts were washed sequentially with water and saturated aqueous brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e78a9204f96c43e3ae9dbd94741185ab
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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