Nitric Acid → HCID 20300406, compound

HRID 2083626Notes

Reaction equation

HRID 2083626 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 3

HCID 944Nitric AcidHCID 24681Fuming sulfuric acidHCID 3699437HCID 3699437, compound

Product 1

HCID 20300406HCID 20300406, compound

Procedure

Over a 21/2 hour period, 210 g. of the 1-(1-ethylpropyl)benzotriazole is added to a mixture of 100 ml. of 90% nitric acid and 400 ml. 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 g. 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 ml. of 95% ethanol and then a second time with an additional 400 ml. of hot 95% ethanol. The slurry is cooled and product is collected by filtration and dried to yield 108.5 g. (45%) of brown solid, m.p. 129°-132° C. The analytical sample is recrystallized from chloroform-petroleum ether to give m.p. 132°-134° C.

Workup

  1. custom2 hour period, 210 g
  2. temperatureThe mixed acid solution is cooled in an ice-salt bath
  3. customis such that a temperature of between 5°-10° C.
  4. temperatureis maintained
  5. temperatureThe reaction mixture is maintained at 5°-10° C. for an additional 11/2 hours
  6. customat 25° C.
  7. additionThe reaction mixture is then poured over 2500 g
  8. stirringAfter 15 minutes of stirring
  9. filtrationthe brown precipitate is collected by filtration
  10. washwashed with additional water and air
  11. customdried
  12. temperatureThe slurry is cooled
  13. filtrationproduct is collected by filtration
  14. customdried
  15. customto yield 108.5 g
  16. customThe analytical sample is recrystallized from chloroform-petroleum ether
  17. customto give m.p. 132°-134° C.

Sources & evidence

ORD record
ord-2c0b203cbfa944ff82f36c5a795dafa3
Source dataset
uspto-grants-1978_04
Patent number
US04086242

Reaction notes

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