Ammonium Chloride → HCID 178441195, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.0 g (12.1 mmole) of 7-(3,5-di-t-butyl-4-hydroxyphenoxy)heptanenitrile (from Example 3), 2.35 g (36.2 mmole) sodium azide, 1.94 g (36.2 mmole) of ammonium chloride, 0.51 g (12.1 mmole) of lithium chloride and 50 ml of N,N-dimethylformamide was heated in a stoppered flask at 120° C. for 48 hours. To this mixture was added 2.35 g (36.2 mmole) of sodium azide and 1.94 g (36.2 mmole) of ammonium chloride, and heating was continued for an additional 48 hours. The reaction mixture was poured into water and extracted twice with chloroform. The chloroform extracts were combined, washed with water, dried with magnesium sulfate and evaporated to give the crude product as a dark oil. This oil was purified by four recrystallizations from a mixture of ethyl acetate and hexane, followed by silica gel chromatography eluting with a mixture of chloroform/methanol/acetic acid in a ratio of 98/2/0.25. After three further recrystallizations, 0.92 g of 5-[6-(3,5-di-t-butyl-4-hydroxyphenoxy)hexyl]-tetrazole, m.p. 128°-131° C., was obtained as a white solid. Analysis: Calculated for: C21H34N4O2 : %C, 67.4; %H, 9.2; %N, I5.0; Found %C, 67.4; %H, 9.3; %N, 15.2.

Provenance & Evidence