Nitric Acid → HCID 178526563, compound

HRID 1733155Notes

Reaction equation

HRID 1733155 reaction equation
[N+:1]([O-:4])(O)=[O:2].[NH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.O>S(=O)(=O)(O)O>[N+:1]([C:13]1[C:8]2[N:7]=[N:6][NH:5][C:9]=2[CH:10]=[CH:11][CH:12]=1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 178418385HCID 178418385, compound

Product 1

HCID 178526563HCID 178526563, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a cooled solution (20° C.) of 1,060 milliliters of 20% fuming sulfuric acid and 265 milliliters of 90% nitric acid is added in a dropwise fashion a solution of 537 grams of benzotriazole in 1000 milliliters of concentrated sulfuric acid. The temperature is not allowed to exceed 50° C. At the end of the addition, the reaction mixture is allowed to stand at room temperature overnight. The reaction mixture is then poured over 9 liters of ice and water and a heavy yellow precipitate forms. The solid is collected by filtration, washed with water and dried. The solid, which is a mixture of the 4-nitro (90%) and the 5-nitro (10%) isomers, is then slurried with 7.5 liters of refluxing acetonitrile, the mixture cooled and 537 grams (73%) of pure 4-nitrobenzotriazole is collected by filtration, m.p. 228°-231° C.

Workup

  1. customto exceed 50° C
  2. additionAt the end of the addition
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried
  6. additiona mixture of the 4-nitro (90%)
  7. temperaturethe mixture cooled
  8. filtration537 grams (73%) of pure 4-nitrobenzotriazole is collected by filtration, m.p. 228°-231° C.

Sources & evidence

ORD record
ord-e084add1154247c1bcfa598995a63f6e
Source dataset
uspto-grants-1980_12
Patent number
US04240822

Reaction notes

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