Ethanol → 4-Nitro-2-phenyl-2H-benzotriazole

HRID 1733157Notes

Reaction equation

HRID 1733157 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1Cl)([O-])=O.[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)C>C(O)(=O)C>[N+:10]([C:6]1[C:5]2[C:4](=[N:1][N:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:21]=2)[CH:9]=[CH:8][CH:7]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 7516PhenylhydrazineHCID 118141-Chloro-2,6-dinitrobenzene

Product 1

HCID 36983024-Nitro-2-phenyl-2H-benzotriazoleYield 18%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 40.6 grams of 2,6-dinitrochlorobenzene, 21.6 grams phenylhydrazine and 350 milliliters of 95% ethanol is heated at the reflux temperature for 22 hours. Then the solvent is evaporated to yield a dark oil. To the oil is added 70 milliliters of acetic acid and the mixture is heated to reflux for 6 hours. After cooling to room temperature, the crude product is collected by filtration, washed with petroleum ether and then washed with hot methanol to yield 8.5 grams (18%) of product m.p. 155°-156° C. The analytical sample is recrystallized from methanol, m.p. 155°-156° C.

Workup

  1. customThen the solvent is evaporated
  2. customto yield a dark oil
  3. temperaturethe mixture is heated
  4. temperatureto reflux for 6 hours
  5. filtrationthe crude product is collected by filtration
  6. washwashed with petroleum ether
  7. washwashed with hot methanol

Sources & evidence

ORD record
ord-7e4606a4e9ae4fa5ab4cd5d441101185
Source dataset
uspto-grants-1980_12
Patent number
US04240822

Reaction notes

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