Azobenzene → 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide

HRID 257653

Reaktionsgleichung

Reaktionsgleichung von HRID 257653
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[N:13]=[N:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:16]=1[OH:26])([O-])=O.ClC1C(=O)C2C(C(=[O:39])C=1Cl)=CC=CC=2.C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.N(C1C=CC=CC=1)=NC1C=CC=CC=1>CO.O>[OH:26][C:16]1[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=1[N:14]1[N+:13]([O-:39])=[C:7]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:6]2=[N:3]1

Komponenten

9

Edukt 6

HCID 2272AzobenzeneHCID 8342DichloneHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 89771Phenol, 2-[2-(4-chloro-2-nitrophenyl)diazenyl]-6-(1,1-dimethylethyl)-4-methyl-HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Produkt 1

HCID 141494702-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Example 4 from U.S. Pat. No. 4,835,284 is duplicated. 97% sodium hydroxide (8.2 g) is added and dissolved in a mixture of methanol (60 ml) and water (20 ml). 2-nitro-4-chloro-2'-hydroxy-3'-t-butyl-5'-methylazobenzene (11.6 g) is then added to the resultant solution at 50° to 60° C. over 30 minutes while stirring, and thereafter 2,3-dichloro-1,4-naphthoquinone (0.3 g) and 9-fluorenone (0.4 g) are added to the solution. Glucose (8 g) is then added to the resultant mixture at 40° to 50° C. over two hours, and the mixture is stirred for one hour at the same temperature. As this result, almost all of the azobenzene disappears to produce 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide. The system is heated, and is stirred at 66° to 68° C. (boiling point) for 5 hours. As this result, the N-oxide disappears. Thereafter, water (50 ml) is added to the reaction liquor, and the resultant reaction liquor is neutralized with 62% sulfuric acid (10 g) to precipitate a crystal. The precipitated crystal is separated by filtration, and the separated crystal is fully washed with hot water of 60° to 70° C. and further with a small amount of methanol. The washed crystal is then dried, thus obtaining 8.7 g of 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotriazole having a melting point of 138° to 140° C. at the yield of 82.9%. One can see that the reaction using an aromatic ketone takes over 71/2 hours.

Aufarbeitung

  1. stirringthe mixture is stirred for one hour at the same temperature

Quellen und Nachweise

ORD-Eintrag
ord-4d37aaee6eb049deb4127a6ebb65ef38
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262541

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