Azobenzene → 2-(2-hydroxy-5-methylphenyl)benztriazole N-oxide

HRID 1763185Notes

Reaction equation

HRID 1763185 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[OH:19])([O-])=[O: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>O.CO>[OH:19][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[N:11]1[N+:1]([O-:2])=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:10]1

Participants

7

Reactant 4

HCID 2272AzobenzeneHCID 10241FluorenoneHCID 740294-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenolHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 132146462-(2-hydroxy-5-methylphenyl)benztriazole N-oxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methanol 60 ml, water 30 ml, 97% sodium hydroxide 12.4 g and 2-nitro-2'-hydroxy-5'-methylazobenzene 12.9 g was heated and stirred at 45°~50° C. 9-fluorenone 1.0 g and then glucose 5.5 g were added to the resultant mixture over 30 minutes while stirring. The mixture was further stirred at 75° C. (boiling point) for 7 hours. As this result, the azobenzene disappeared to produce 2-(2'-hydroxy-5'-methylphenyl)benzotriazole-N-oxide.

Workup

  1. temperaturewas heated
  2. stirringwhile stirring
  3. stirringThe mixture was further stirred at 75° C. (boiling point) for 7 hours

Sources & evidence

ORD record
ord-98ca9fc5c6bc42c0b11710e27228be5e
Source dataset
uspto-grants-1989_05
Patent number
US04835284

Reaction notes

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