5-chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzophenone synthesis

Yield:38150-27-5 72.8%

Reaction Conditions:

with paraformaldehyde in 5,5-dimethyl-1,3-cyclohexadiene;

Steps:

7 5-Chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl] benzophenone

PREPARATION 7 5-Chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl] benzophenone A stirred mixture of 5-chloro-2-(3-methyl-4H-1,2,4-triazolo-4 -yl)benzophenone, (2.98 g., 0.01 mole) paraformaldehyde (3 g.) and xylene (100 ml.) was warmed under nitrogen, in a bath maintained at 125° C. for 7 hours. The mixture was then concentrated in vacuo. The residue was chromatographed on silica gel (150 g.) with 3% methanol-97% chloroform. Fifty-ml. fractions were collected. The product was eluted in fractions 20-44. The fractions were concentrated and the residue was crystallized from ethanol-ethyl acetate to give: 1.64 g. of 5-chloro-2-[3-(hydroxymethyl)-5-methyl-4H-1,2,4-triazol-4-yl] benzophenone, of melting point 138°-142° C.; 0.316 g. of melting point 138.5°-141° C.; and 0.431 g. of melting point 139°-141° C., (72.8% yield). The analytical sample had a melting point of 138°-139° C. Anal. calcd. for C₁₇ H₁₄ ClN₃ O₂: C, 62.30; H, 4.30; Cl, 10.81; N, 12.82. Found: C, 62.23; H, 4.22; Cl, 10.82; N, 11.73.

References:

US3993660,1976,A