Triethylamine → N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide

HRID 1952268

Reaktionsgleichung

Reaktionsgleichung von HRID 1952268
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](Cl)=[O:9])[C:4]([CH3:11])=[N:3]1.[CH2:12]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[CH:23]([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])[NH2:19])[CH:13]([CH3:15])[CH3:14].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH2:12]([C:16]1[CH:17]=[C:18]([NH:19][C:8]([C:5]2[C:4]([CH3:11])=[N:3][N:2]([CH3:1])[C:6]=2[CH3:7])=[O:9])[CH:20]=[CH:21][C:22]=1[CH:23]([C:28]([F:29])([F:30])[F:31])[C:24]([F:25])([F:26])[F:27])[CH:13]([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 13637622trimethyl-1H-pyrazole-4-carbonyl chlorideHCID 866190043-Isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

Produkt 1

HCID 86629861N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamideAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1,3,5-Trimethylpyrazole-4-carbonyl chloride (2.09 g, 10.0 mmol), 3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (2.0 g, 6.69 mmol), and triethylamine (1.35 g, 13.4 mmol) were dissolved in tetrahydrofuran (60 ml), and the mixture was heated under reflux for 5 hr. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3) to give the desired compound (2.41 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-7845337b972042fba4c5c1690ae49722
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404861B2

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