2-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzene → 2,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenol

HRID 441512

Reaction equation

HRID 441512 reaction equation
OC1C(C(CC)(C)C)=CC(C(CC)(C)C)=CC=1N=NC1C=CC=CC=1[N+]([O-])=O.[OH:29][C:30]1[C:35]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:34][C:33]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:32][C:31]=1[N:44]=[N:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[N+:53]([O-])=O>>[Cl:52][C:50]1[CH:49]=[CH:48][C:47]2=[N:53][N:44]([C:31]3[CH:32]=[C:33]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:34]=[C:35]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:30]=3[OH:29])[N:45]=[C:46]2[CH:51]=1

Participants

3

Reactant 2

HCID 1041112-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzeneHCID 1355451802,4-Di-tert-butyl-6-[2-(5-chloro-2-nitrophenyl)hydrazinylidene]cyclohexa-2,4-dien-1-one

Product 1

HCID 774702,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenolYield 80.4%

Procedure

When in Example 1, the 2'-hydroxy-3',5'-di-tert-amyl-2-nitroazobenzene was replaced by an equivalent amount of 2'-hydroxy-3',5'-di-tert-butyl-5-chloro-2-nitroazobenzene, the product 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole was obtained after a reaction time of 5 hours in a yield of 80.4% of theory as an isolated product of melting point 151°-154° C. An additional 4.5% yield was present in the mother liquor for an overall yield of 84.9% of theory.

Sources & evidence

ORD record
ord-a902cf19898e4feeb799c17d21b3124a
Source dataset
uspto-grants-1977_08
Patent number
US04041044

Linked notes

Loading…