Ammonium Chloride → HCID 178441222, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.0g (0.011 mole) of 2,6-di-t-butyl-4-[(4-cyanophenyl)methylthio]phenol, 1.1 g (0.034 mole) of sodium azide, 0.6 g (0.034 mole) of ammonium chloride, 0.24 g (0.011 mole) of lithium chloride and 20 ml of N,N-dimethylformamide was heated at 115° C. in a stoppered flask for 120 hours. The N,N-dimethylformamide was evaporated and the residual material partitioned between water and chloroform. The chloroform layer was dried with magnesium sulfate, and was then evaporated to give the crude product as a brown oil. This oil was purified by silica gel chromatography eluting with a mixture of chloroform/methanol/acetic acid in a ratio of 98/2/0.25 followed by two recrystallizations from a mixture of chloroform and hexane to give 0.92 g of 5-{4-[(3,5-di-t-butylphenylthio)methyl]phenyl}tetrazole as a cream-colored solid, m.p. 187°-189° C. Analysis: Calculated for C22H28N4OS: %C, 66.6; %H, 7.1; %N, 14.1; Found: %C, 66.6; %H, 7.3; %N, 14.3.

Provenance & Evidence