Ammonium Chloride → HCID 178441187, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.68 g (5 mmole) of 2,6-di-t-butyl-4-[(4-cyanophenyl)methoxy]phenol (from Example 1) 0.97 g (15 mmole) of sodium azide, 0.30 g (15 mmole) of ammonium chloride, 0.21 g (5 mmole) of lithium chloride and 25 ml of N,N-dimethylformamide was heated in a stoppered flask at 100° C. for 16 hours. The reaction mixture was poured into a mixture of ice and water, and was then extracted with chloroform. The chloroform extract was washed with water, dried and evaporated to give the crude product as an oil. The oil was triturated with water to give a solid. The solid was purified by silica gel chromatography eluting with a mixture of methanol/chloroform/acetic acid in a ratio of 5/94.5/0.5 followed by two recrystallizations from a mixture of methanol, chloroform and hexane to give 0.22 g of white 5-[4-(3,5-di-t-butyl-4-hydroxyphenoxymethyl)phenyl]tetrazole, m.p. 235°-237° C. Analysis: Calculated for C22H28N4O2 : %C, 69.4; %H. 7.4; %M, 14 7; Found: %C, 69.0; %H, 7.6; %N, 14.6.

Provenance & Evidence