- One Synthetic Approach of ICI 195739
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ICI 195739 (CAS NO.: 103961-78-0), with its systematic name of 1H-1,2,4-Triazole-1-ethanol, alpha-(2,4-difluorophenyl)-3-(2-(4-(2,2,3,3-tetrafluoropropoxy)phenyl)ethenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl)-, could be produced through many synthetic methods.
Following is one of the synthesis routes:
4-(2,2,3,3-Tetrafluoropropoxy)benzaldehyde (I) is condensed with refluxing acetic anhydride to produce 3-[4-(2,2,3,3-tetrafluoropropoxy) phenyl]acrylic acid (II), which is treated with refluxing SOCl2 to afford the corresponding acid chloride (III). Next, the reaction of (III) with thiosemicarbazide in toluene affords 3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]acryloylthiosemicarbazide (IV), which is cyclized by means of NaNO2 and HNO3 in water to give 3-[4-(2,2,3,3-tetrafluoropropoxy) styryl]-1,2,4-triazole (V). Finally, this compound is condensed with 2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)-1,2-epoxypropane (VI) by means of NaH in hot DMF.
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