Nitric Acid → HCID 178526563, compound

HRID 2083627Notes

Reaction equation

HRID 2083627 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[N:11]1>O>[N+:6]([C:18]1[C:13]2[N:12]=[N:11][NH:10][C:14]=2[CH:15]=[CH:16][CH:17]=1)([O-:9])=[O:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 178418385HCID 178418385, compound

Product 1

HCID 178526563HCID 178526563, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled solution (20° C.) of 1,060 ml. of 23% fuming sulfuric acid and 265 ml. of 90% nitric acid is added in a dropwise fashion a solution of 537 g. of benzotriazole in 1000 ml. of concentrated sulfuric acid. The temperature is not allowed to go above 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 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%) products, is then slurried with 7.5 l. of hot acetonitrile cooled and 537 g. (73%) of 4-nitrobenzotriazole is collected by filtration, m.p. 228°-231° C.

Workup

  1. customTo a cooled solution (20° C.) of 1,060 ml
  2. customto go above 50° C
  3. additionAt the end of the addition
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried
  7. additiona mixture of the 4-nitro (90%)
  8. temperatureof hot acetonitrile cooled
  9. filtration(73%) of 4-nitrobenzotriazole is collected by filtration, m.p. 228°-231° C.

Sources & evidence

ORD record
ord-0ecd70779bfc4d1a88f7abfd15bbeaab
Source dataset
uspto-grants-1978_04
Patent number
US04086242

Reaction notes

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