Benzyl Chloride → 1-Benzyl-5-phenyl-1H-tetraazole

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Reaction Steps

Benzyl chloride (0.15 mole; 19.0 g), sodium 5-phenyltetrazole (0.165 mole; 27.4 g) and 2-methoxyethanol (100 ml) were heated at 100° C. for 3.5 hours). The mixture was cooled to precipitate NaCl. Water (250 ml) was added to the filtrate to precipitate a product which was filtered, washed with H2O (50 ml) and dried in-vacuo at 60° C. for four hours. The product weight was 32.8 g. (92.5 percent yield), m.p. 54°-67° C. Reported; 2-benzyl-5-phenyltetrazole, m.p. 65.5°-66° C. 1-benzyl-5-phenyltetrazole, m.p. 92.5°-93° C. Elemental analysis found: C, 71.57; H, 5.30; N, 21.39. Calculation for C14H 12N4 : C, 71.17; H, 5.12; N, 23.71. 13C NMR established a 3/1 isomer ratio for the 2-benzyl/1 -benzyl substitution products, respectively. The isomers are represented by the following structures; ##STR6##

Provenance & Evidence