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

HRID 1099681

Reaktionsgleichung

Reaktionsgleichung von HRID 1099681
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d3f52e943fbc4d4e9dbc829739279d92
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143410B2

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