Triethylamine → N-(2-Cyclohexylphenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide

HRID 1588786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588786
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](Cl)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[CH:14]1([C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH2:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[CH:14]1([C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH:22][C:7]([C:5]2[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=2)=[O:8])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 4078992-CyclohexylbenzenamineHCID 27945811-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride

Produkt 1

HCID 19754740N-(2-Cyclohexylphenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamideAusbeute 111,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid chloride (1.6 g) in CH2Cl12 (25 mL) at 0° C. was added dropwise a solution of 2-cyclohexylaniline (1.3 g) and triethylamine (1.0 mL) in CH2Cl2 (25 mL). The contents were stirred overnight, coming to RT. The contents were washed with water, 2N HCl (2×100 mL), dried (MgSO4) and concentrated in vacuo leaving an amber foam (2.9 g). Crystallization from EtOAc/hexane gave the desired amide as white crystals (1.2 g). Most of the compounds of the present invention were made via this coupling procedure.

Aufarbeitung

  1. customcoming to RT
  2. washThe contents were washed with water, 2N HCl (2×100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11d9c13f5ebf4b6a92dc2e9a0a23d981
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223526

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