Nitric Acid → HCID 20300406, compound

HRID 1733154Notes

Reaction equation

HRID 1733154 reaction equation
[CH2:1]([CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1)[CH2:4][CH3:5])[CH3:2].[N+:15]([O-])([OH:17])=[O:16]>OS(O)(=O)=O.O=S(=O)=O>[CH2:1]([CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:9]=2[N:8]=[N:7]1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 3699437HCID 3699437, compound

Product 1

HCID 20300406HCID 20300406, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

Over a 21/2 hour period, 210 grams of the 1-(1-ethylpropyl)benzotriazole is added to a mixture of 100 milliliters of 90% nitric acid and 400 milliliters of 23% oleum with stirring. The mixed acid solution is cooled in an ice-salt bath and the addition rate is such that a temperature of between 5°-10° C. is maintained. The reaction mixture is maintained at 5°-10° C. for an additional 11/2 hours and then at 25° C. for one more hour. The reaction mixture is then poured over 2500 grams of ice with stirring. After 15 minutes of stirring, the brown precipitate is collected by filtration, washed with additional water and air dried. The crude product is then slurried with 500 milliliters of 95% ethanol and then a second time with an additional 400 milliliter of hot 95% ethanol. The slurry is cooled and the product is collected by filtration and dried to yield 108.5 grams (45%) of brown solid, m.p. 129°-132° C. The analytical sample is recrystallized from chloroform-petroleum ether to give a m.p. 132°-134° C.

Workup

  1. temperatureThe mixed acid solution is cooled in an ice-salt bath
  2. customis such that a temperature of between 5°-10° C.
  3. temperatureis maintained
  4. temperatureThe reaction mixture is maintained at 5°-10° C. for an additional 11/2 hours
  5. customat 25° C.
  6. stirringwith stirring
  7. stirringAfter 15 minutes of stirring
  8. filtrationthe brown precipitate is collected by filtration
  9. washwashed with additional water and air
  10. customdried
  11. temperatureThe slurry is cooled
  12. filtrationthe product is collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-6c9dde9fba544e8b816727d7b0fb564b
Source dataset
uspto-grants-1980_12
Patent number
US04240822

Reaction notes

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