Sulfuric Acid → HCID 18540656, compound

HRID 411586Notes

Reaction equation

HRID 411586 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:14])[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[C:3]=1[C:18]#[N:19].[OH:20]S(O)(=O)=O>>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:14])[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[C:3]=1[C:18]([NH2:19])=[O:20]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 18540689HCID 18540689, compound

Product 1

HCID 18540656HCID 18540656, compoundYield 53%

Procedure

Part C: A mixture of 1.5 g (5.5 mmol) of 5-amino-4-cyano-3-isopropyl-1-(2-chloro-6-methylphenyl)pyrazole in 5 mL conc. H2SO4 was stirred at room temperature for 24 hours. The reaction was slowly quenched with ice and then diluted with water. The solution was made basic with saturated Na2CO3, stirred 2 h and filtered. The solid was recrystallized from hexanes/EtOAc to afford 847 mg (53%) of 5-amino-3-isopropyl-1-(2-chloro-6-methylphenyl) pyrazole-4-carboxamide, mp 72-74° C. Mass Spec. (ES−): 291 (M−H)−.

Workup

  1. customThe reaction was slowly quenched with ice
  2. additiondiluted with water
  3. stirringstirred 2 h
  4. filtrationfiltered
  5. customThe solid was recrystallized from hexanes/EtOAc

Sources & evidence

ORD record
ord-e33f4775fec54d7e8b69d27bcd7a8b3e
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

Loading…