2,6-Di-t-butyl-p-benzoquinone → 2,6-Di-tertiary-butyl-4-(4'-cyanomethylphenylimino)-2,5-cyclohexadiene-1-one
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[C:11]([C:15]1[C:16](=[O:26])[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][C:19](=O)[CH:20]=1)([CH3:14])([CH3:13])[CH3:12]>>[C:22]([C:17]1[C:16](=[O:26])[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:20][C:19](=[N:1][C:2]2[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=2)[CH:18]=1)([CH3:25])([CH3:24])[CH3:23]Participants
3
Procedure
Using the method of Example 1, 4-aminobenzylcyanide was reacted with 2,6-di-tertiary-butyl-p-benzoquinone to give 2,6-di-tertiary-butyl-4-(4'-cyanomethylphenylimino)-2,5-cyclohexadiene-1-one, m.p. 126.5°-127.5° C. Following the reduction method of Example 1, Step B, the corresponding anilino phenylacetonitrile, m.p. 146°-147° C., was obtained. This was converted to 5-[4-(3,5-di-t-butyl-4-hydroxyanilino)benzyl]tetrazole, m.p. 212°-214° C. (dec), following the method of Example 30, but carried out at 110° C. for 48 hours.
Sources & evidence
- ORD record
- ord-0667c16ef61a44ee8420eb89fd26b0da