3-Iodoaniline → N-(3-iodophenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 607434

Reaction equation

HRID 607434 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][N:10]1[C:14]([C:15](Cl)=[O:16])=[CH:13][C:12]([CH3:18])=[N:11]1>N1C=CC=CC=1.ClCCCl>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:15]([C:14]2[N:10]([CH3:9])[N:11]=[C:12]([CH3:18])[CH:13]=2)=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 122713-IodoanilineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chloride

Product 1

HCID 57657852N-(3-iodophenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1049PyridineSolvent

Procedure

To a solution of 3-iodoaniline (131 mg, 0.60 mmol) in 1.5 ml pyridine at room temperature was added over 2 minutes a solution of 1,3-dimethylpyrazole-5-carbonyl chloride (79 mg, 0.50 mmol) in 0.3 ml 1,2-dichloroethane. The reaction was stirred at room temperature for 30 minutes, quenched into a NaHCO3 solution, and extracted into EtOAc. The EtOAc solution was washed with NaHCO3 solution, brine, dried with anhydrous Na2SO4 and rotary evaporated. The resultant gummy solid was recrystallized from hexane/EtOAc to give the title compound as solid white needles (135 mg, 80%).

Workup

  1. customquenched into a NaHCO3 solution
  2. extractionextracted into EtOAc
  3. washThe EtOAc solution was washed with NaHCO3 solution, brine
  4. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  5. customThe resultant gummy solid was recrystallized from hexane/EtOAc

Sources & evidence

ORD record
ord-fc3eeb39e5c74fe9904d292d1624b60f
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Linked notes

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