Sodium Carbonate → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

HRID 1384491Notes

Reaction equation

HRID 1384491 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[C:15]([CH2:18][C:19]#[N:20])[C:16]#[N:17].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[NH2:20][C:19]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:5][C:4]=2[Cl:12])[N:14]=[C:15]([C:16]#[N:17])[CH:18]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 853091952-(2,6-Dichloro-4-trifluoromethylphenylhydrazono)succinonitrile

Product 1

HCID 33039135-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)succinonitrile (1.0 g) and sodium bicarbonate (40 ml of a saturated aqueous solution) and dichloromethane (915 ml) was stirred at 20° C. for 3 hours at pH 9. Sodium carbonate solution was then added until the pH was 11 and the stirring continued overnight. A small amount of sodium hydroxide solution was added to give a pH of 12, followed three hours later by a small quantity of Aliquat 336 (trademark, tricaprylylmethylammonium chloride), and after 2 hours the reaction was complete. A dichloromethane extract was washed (water and brine), dried (sodium sulfate) and evaporated to give the title compound.

Workup

  1. customthe stirring continued overnight
  2. customto give a pH of 12
  3. extractionA dichloromethane extract
  4. washwas washed (water and brine)
  5. dry with materialdried (sodium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-5d7966dbaaea4fff9089e5c6dc7ddaf1
Source dataset
uspto-grants-2001_07
Patent number
US06258973B1

Reaction notes

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