Sulfuric Acid → 5-Amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

HRID 1860548Notes

Reaction equation

HRID 1860548 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]#[N:20].[OH:21]S(O)(=O)=O.[OH-].[Na+]>>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]([NH2:20])=[O:21]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 185406775-Amino-4-cyano-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole

Product 1

HCID 185406305-Amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamideYield 92%

Procedure

Part B: Thirty grams (91.0 mmol) of 5-amino-4-cyano-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole was dissolved in 80 mL of con. H2SO4 and stirred 24 h at RT. The solution was added to cold aqueous NaOH, and the resulting precipitate was filtered, washed with water, and dried under vacuum to give 29.1 g (92%) of 5-amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide as a white solid. 1H NMR (CDCl3, 300 MHz) δ 7.49(s, 2H); 5.06-5.63(m, 4 H); 3.06(septet, 1H, J=6.8 Hz); 1.39(d, 6H, J=6.9 Hz).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4e8c5d7178b2441a88b4670d6849927a
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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