تفاعل #65006

معادلة التفاعل

lithium chloride

3-(3,5-di-t-butyl-4-hydroxyanilino)benzonitrile

sodium azide

hydrochloric acid

ammonium chloride

→

5-[3-(3,5-di-t-butyl-4-hydroxyanilino)phenyl]tetrazole

المردود 65.3%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىa gummy solid precipitated out
2. 2
   أخرىThe supernatant was decanted off
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethanol
4. 4
   workup.ADDITIONThe ethanol solution was diluted with water
5. 5
   أخرىa pink solid was collected
6. 6
   أخرىThis material was recrystallized from a mixture of ethanol and water

الإجراء التجريبي

Eight g (0.025 mole) of 3-(3,5-di-t-butyl-4-hydroxyanilino)benzonitrile (from Example 27), 4.9 g (0.075 mole) of sodium azide, 4.0 g (0.075 mole) of ammonium chloride, 1.06 g (0.025 mole) of lithium chloride and 60 ml of N,N-dimethylformamide were combined under a nitrogen atmosphere and heated at 110° C. for 48 hours. The reaction mixture was poured into cold 6N hydrochloric acid and a gummy solid precipitated out. The supernatant was decanted off and the residue dissolved in ethanol. The ethanol solution was diluted with water and a pink solid was collected. This material was recrystallized from a mixture of ethanol and water to give 5.97 g of 5-[3-(3,5-di-t-butyl-4-hydroxyanilino)phenyl]tetrazole, m.p. 231°-233° C. Analysis: Calculated for C21H27N5O: % C, 69.0; % H, 7.4; % N, 19.2; Found: % C, 68.4; % H, 7.6; % N, 18.8.

المصدر