3-(1,2,3-THIADIAZOL-4-YL)BENZENOL synthesis

Yield:303149-00-0 71%

Reaction Conditions:

with thionyl chloride at 20;

Steps:

36

3-(1,2,3-Thiadiazol-4-yl)phenol (36b). Hydrazone 36a (3.5 g, 15.7 mmol, 1 equiv.) was stirred overnight with an excess amount of thionyl chloride (35 ml_, 30 equiv.) at room temperature. The remaining thionyl chloride was evaporated under reduced pressure. The reaction crude was filtered trough a plug of silica (PE/EtOAc 1 :1 ) and then recrystallized from CHCI₃ giving 2.0 g (71 %) of product as pale yellow solid. ¹H NMR (DMSO-d₆, 500.1 MHz) 9.76 (bs, 1 H), 9.59 (s, 1 H), 7.60-7.57 (m, 2H), 7.38 (dd, J = 7.9, 7.9 Hz, 1 H) ppm; ¹³C NMR (DMSO-d₆, 125.1 MHz): 162.9, 158.9, 134.0, 132.8, 131.3, 118.9, 117.3, 114.8 ppm; Anal, calcd for C₈H₆N₂O₁S: C, 53.92; H, 3.39; N, 15.72; found: C, 53.45; H, 3.42; N, 15.41 ; MS (ES⁺) calcd. for C₈H₆N₂OS 178.21 , found: [M + H]⁺ 179.28.

References:

WO2008/129129,2008,A1 Location in patent:Page/Page column 56