5-(4-HYDROXY-PHENYL)-3H-[1,2,3]TRIAZOLE-4-CARBONITRILE synthesis

Yield:39807-61-9 76%

Reaction Conditions:

with sodium azide in N,N-dimethyl-formamide; for 2 h;Heating / reflux;

Steps:

948

A mixture of 2-benzenesulfonyl-3-(4-hydroxyphenyl)acrylonitrile (2.08 g, 7.3 mmol) and so- dium azide (0.47g,7.3 mmol) in DMF (50 ml_) was heated at reflux temperature 2 hours. After cooling, the mixture was poured on ice. The mixture was evaporated in vacuo to almost dryness and toluene was added. After filtration, the organic phase was evaporated in vacuo. The residue was purified by silicagel chromatography eluting with a mixture of ethyl acetate and heptane (1 :2). This afforded 1 .2 g (76%) of the title compound.1 H NMR (DMSO-dβ): 10.2 (broad, 1 H); 7.74 (d,2H); 6.99 (d,2H); 3.6-3.2 (broad, 1 H). HPLC-MS (Method C) m/z: = 187 (M+1 ); Rt. = 1.93 min

References:

WO2006/82245,2006,A1 Location in patent:Page/Page column 362-363