Potassium Iodide → HCID 178521931, compound

HRID 1624969Notes

Reaction equation

HRID 1624969 reaction equation
N([O-])=O.[Na+].[C:5]1([NH:11][C:12]([C:14]2[C:18](N)=[CH:17][NH:16][N:15]=2)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[I-:20].[K+]>O.Cl.CC(C)=O.[Cl-].[Na+].O.C(OCC)(=O)C.[Cu]I>[C:5]1([NH:11][C:12]([C:14]2[C:18]([I:20])=[CH:17][NH:16][N:15]=2)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

10

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 178508055HCID 178508055, compound

Product 1

HCID 178521931HCID 178521931, compoundYield 21.7%

Reagents, catalysts & solvents 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

An aqueous solution of sodium nitrite (760 mg) in 2 ml of water was added drop wise to a stirred suspension of 4-amino-1H-pyrazole-3-carboxylic acid phenylamide (2 g; 10 mmol) in concentrated hydrochloric acid (20 ml) at 0° C., then stirred at 0° C. for a further 60 minutes. The reaction mixture was diluted with acetone (10 ml) then treated with potassium iodide (1.8 g) and copper (I) iodide (2.1 g) and stirred at room temperature for 90 minutes. The reaction mixture was diluted with brine and ethyl acetate then washed with saturated sodium thiosulphate solution. The ethyl acetate layer was separated, dried (MgSO4), filtered and evaporated to give 680 mg of 4-iodo-1H-pyrazole-3-carboxylic acid phenylamide.

Workup

  1. stirringstirred at room temperature for 90 minutes
  2. washthen washed with saturated sodium thiosulphate solution
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-44c8257191814cddaefed0b2f3d1bb54
Source dataset
uspto-grants-2014_07
Patent number
US08779147B2

Reaction notes

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