Sulfuric Acid → HCID 19432808, compound

HRID 487250Notes

Reaction equation

HRID 487250 reaction equation
S(=O)(=O)(O)[OH:2].[CH:6]1([N:12]2[C:16]([NH2:17])=[C:15]([C:18]#[N:19])[C:14]([CH3:20])=[N:13]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C(O)(=O)C>[CH:6]1([N:12]2[C:16]([NH2:17])=[C:15]([C:18]([NH2:19])=[O:2])[C:14]([CH3:20])=[N:13]2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 799242HCID 799242, compound

Product 1

HCID 19432808HCID 19432808, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To concentrated sulfuric acid (50 ml) at 0° C. was added 1-cyclohexyl-3-methyl-4-cyano-5-amino-1H-pyrazole (2.2 g, 10.8 mmol). The reaction mixture was warmed to room temperature and stirred for 24 hours. The solution was poured into ice/concentrated ammonium hydroxide, the solution was then neutralized with acetic acid and extracted with dichloromethane (2×400 ml). The solvent was removed in vacuo, the residue was extracted with ethyl acetate (75 ml) and treated with DARCO. The solution was filtered, the solvent was removed in vacuo and the residue was dissolved in ether and cooled. A precipitate was obtained which was collected by filtration, washed with ether and dried at 50° C. in high vacuum for 60 hours to afford 1.83 g (76%) of 1-cyclohexyl-3-methyl-5-amino-1H-pyrazole-4-carboxamide as yellow needles, m.p. 181°-182° C.

Workup

  1. additionThe solution was poured into ice/concentrated ammonium hydroxide
  2. extractionextracted with dichloromethane (2×400 ml)
  3. customThe solvent was removed in vacuo
  4. extractionthe residue was extracted with ethyl acetate (75 ml)
  5. additiontreated with DARCO
  6. filtrationThe solution was filtered
  7. customthe solvent was removed in vacuo
  8. dissolutionthe residue was dissolved in ether
  9. temperaturecooled
  10. customA precipitate was obtained which
  11. filtrationwas collected by filtration
  12. washwashed with ether
  13. customdried at 50° C. in high vacuum for 60 hours

Sources & evidence

ORD record
ord-e2bca75553404ef78ffe0771258c5f94
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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