1-[(4-Methylphenyl)sulfonyl]-1H-imidazole

Chemical Properties

white to slightly yellow crystals

Uses

1-(p-Toluenesulfonyl)imidazole was used in the synthesis of cationic water soluble cyclodextrin, mono-6^A-(1-butyl-3-imidazolium)-6^A-deoxy-β-cyclodextrin chloride (BIMCD), useful in chiral separation of amino acids and anionic pharmaceuticals by capillary electrophoresis.

Uses

Alcohols to azides in one step.1

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 547, 1980 DOI: 10.1021/jo01291a044

General Description

1-(p-Toluenesulfonyl)imidazole converts alcohols to azides in one step.

Synthesis

(a) In a three-necked round-bottomed flask equipped with a charging funnel, oil collector, magnetic stirring bar and protected by argon, imidazole (5.502 g, 0.081 mol) was dissolved in 25 mL of anhydrous dichloromethane. After cooling the solution to 0°C, p-toluenesulfonyl chloride (6.78 g, 0.036 mol) dissolved in 25 mL of anhydrous dichloromethane was added slowly and dropwise. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was subsequently filtered through silica gel and the residual solid was washed with 50 mL hexane/ethyl acetate (1:1, v/v). The filtrate was concentrated in a rotary evaporator, redissolved in 6 mL of ethyl acetate and precipitation was induced by the addition of 60 mL of hexane. The resulting white solid was filtered and dried to give 7.12 g of 1-tosylimidazole (0.032 mol, 89% yield).

References

[1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2209 - 2218
[2] Organic Syntheses, 2000, vol. 77, p. 225 - 225
[3] Tetrahedron, 2016, vol. 72, # 3, p. 379 - 391
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1855 - 1858
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 9, p. 1867 - 1875