Sulfuric Acid → HCID 45790758, compound

HRID 233579Notes

Reaction equation

HRID 233579 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:3]=1[C:20]#[N:21].S(=O)(=O)(O)[OH:23].[OH-].[NH4+]>>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:3]=1[C:20]([NH2:21])=[O:23]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 39103164HCID 39103164, compound

Product 1

HCID 45790758HCID 45790758, compound

Conditions

Temperature
50 °C

Procedure

While maintaining an internal reaction temperature of 10°-15° C., 5-amino-4-cyano-3-(4'-methylphenyl)-1-phenylpyrazole (3.4 g, 12 mmol) was added in a portionwise manner to concentrated sulfuric acid (15 mL). After the addition was complete, the reaction mixture was heated at 50° C. for 4 hours. The reaction was cooled, poured over ice, neutralized with concentrated ammonium hydroxide and extracted with EtOAc. The organic layer was washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The resulting solids were recrystallized from MeOH/H2O to afford 3.0 g of the title compound; m.p. 190°-191° C.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was cooled
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solids were recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-2b2e198a701c42fdab9f3e5d16cd6695
Source dataset
uspto-grants-1997_01
Patent number
US05593997

Reaction notes

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