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

HRID 854679Notes

Reaction equation

HRID 854679 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)[S: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[S: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 25176564-(Chloromethyl)-2-(4-methoxyphenyl)-1,3-thiazoleHCID 178418936HCID 178418936, compound

Product 1

HCID 694293601-[2-(4-methoxy-phenyl)-thiazol-4-ylmethyl]-1H-[1,2,3]triazoleYield 82%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 1.50 g (6.3 mmol) 4-chloromethyl-2-(4-methoxy-phenyl)-thiazole, 0.65 g (9.4 mmol) 1H-[1,2,3]triazole, 0.11 g (0.63 mmol) potassium iodide and 0.37 g (9.4 mmol) sodium hydroxide in 20 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 and concentrated to yield 1.4 g (82%) 1-[2-(4-methoxy-phenyl)-thiazol-4-ylmethyl]-1H-[1,2,3]triazole as beige crystals, melting at 89-94° C.

Workup

  1. customAfter evaporation
  2. customthe residue was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54afda2f32ad4501acfee0d22229f4a2
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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