Potassium Iodide → 1-[2-(4-methoxy-phenyl)-oxazol-4-ylmethyl]-1H-[1,2,3]triazole

HRID 854677Notes

Reaction equation

HRID 854677 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[O:6][CH:7]=1.[NH:16]1[CH:20]=[CH:19][N:18]=[N:17]1.[I-].[K+].[OH-].[Na+]>CC(O)(CC)C>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[O:6][CH:7]=[C:3]([CH2:2][N:16]3[CH:20]=[CH:19][N:18]=[N:17]3)[N:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 199587944-(Chloromethyl)-2-(4-methoxyphenyl)-1,3-oxazoleHCID 178418936HCID 178418936, compound

Product 1

HCID 694249801-[2-(4-methoxy-phenyl)-oxazol-4-ylmethyl]-1H-[1,2,3]triazoleYield 64%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 5.59 g (25 mmol) 4-chloromethyl-2-(4-methoxy-phenyl)-oxazole, 2.59 g (37.5 mmol) 1H-[1,2,3]triazole, 0.41 g (2.5 mmol) potassium iodide and 1.5 g (37.5 mmol) sodium hydroxide (NaOH) in 50 ml 2-methyl-2-butanol was stirred at 120° C. for 5 h. After evaporation, the residue was quenched with water and extracted with ethyl acetate. The extract was dried, concentrated and purified on silica. Elution with ethyl acetate yielded 4.1 g (64%) 1-[2-(4-methoxy-phenyl)-oxazol-4-ylmethyl]-1H-[1,2,3]triazole as white crystals, melting at 126-127° C.

Workup

  1. customAfter evaporation
  2. customthe residue was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified on silica
  7. washElution with ethyl acetate

Sources & evidence

ORD record
ord-659cccd970954677ac22b9dd361dfb45
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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