Pyridine → HCID 9880724, compound

HRID 584740Notes

Reaction equation

HRID 584740 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=[N:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[NH2:4].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=O)=[CH:20][CH:19]=1.N1C=CC=CC=1>O1CCOCC1>[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]2[N:6]([C:7]3[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=3)[N:5]=[C:3]([C:2]([F:14])([F:15])[F:1])[N:4]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 67119946HCID 67119946, compound

Product 1

HCID 9880724HCID 9880724, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,2,2-trifluoro-N′-(4-methylphenyl)ethanehydrazonamide (0.62 g, 2.85 mmol), 4-methoxybenzoyl chloride (584 mg, 3.43 mmol), and pyridine (0.277 mL, 3.43 mmol) in dioxane (6 mL) was refluxed with stirring for 1 hour. After cooling, the solvent was removed under reduced pressure. ethyl acetate-tetrahydrofuran (9:1) and water was poured into the residue and the organic layer was separated, washed with 0.1 N hydrochloric acid, water, and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane-ethyl acetate 8:1-1:1). The desired product was recrystallized from hexane and dried in vacuo to give 5-(4-methoxyphenyl)-1-(4-methylphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (370 mg, 38.9% yield).

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. customthe solvent was removed under reduced pressure
  4. additionethyl acetate-tetrahydrofuran (9:1) and water was poured into the residue
  5. customthe organic layer was separated
  6. washwashed with 0.1 N hydrochloric acid, water, and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography (hexane-ethyl acetate 8:1-1:1)
  10. customThe desired product was recrystallized from hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-7ffb63e602cc4fd3b92f758b100126a3
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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