Sodium Azide → 5-Chloromethyl-1-(4-methoxy-benzyl)-1H-tetrazole

Participants

Reaction Conditions

Reaction Steps

A solution of 9.55 g (48.6 mmol) 2-chloro-1,1,1-triethoxyethane and 3.9 ml (30 mmol) 4-methoxybenzylamine were heated at 40° C. for 15 min. Then a solution of 2.92 g (45 mmol) sodium azide in 60 ml acetic acid was added at RT and heated at 60° C. over night, 20h at 80° C. and 1h at 100° C. The reaction was neutralized with aqueous and solid NaHCO3/EtOAc (3×), washed with aqueous 10% NaCl. The organic phase was dried over Na2SO4, evaporated and purified by flash-chromatography on silicagel (hexane/EtOAc 1:1) to give 3.36 g (47%) 5-Chloromethyl-1-(4-methoxy-benzyl)-1H-tetrazole, MS: 238 (M). [Y. Satoh, S. De Lombaert, N. Marcopulos, J. Moliterni, M. Moskal, J. Tan, E. Wallace, Synthesis of tetrazole analogs of alpha-amino acids by alkylation of a Schiff base of alpha-aminomethyltetrazole. Tetrahedron Lett. (1998), 39(21), 3367-3370].

Provenance & Evidence