Triethylamine → N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide

HRID 1952263

Reaktionsgleichung

Reaktionsgleichung von HRID 1952263
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](Cl)=[O:9])[C:4]([CH3:11])=[N:3]1.[CH3:12][O:13][C:14]([C:23]1[C:29]([CH2:30][CH2:31][CH3:32])=[CH:28][C:26]([NH2:27])=[C:25]([CH3:33])[CH:24]=1)([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH3:12][O:13][C:14]([C:23]1[C:29]([CH2:30][CH2:31][CH3:32])=[CH:28][C:26]([NH:27][C:8]([C:5]2[C:4]([CH3:11])=[N:3][N:2]([CH3:1])[C:6]=2[CH3:7])=[O:9])=[C:25]([CH3:33])[CH:24]=1)([C:15]([F:16])([F:17])[F:18])[C:19]([F:20])([F:22])[F:21]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 13637622trimethyl-1H-pyrazole-4-carbonyl chlorideHCID 866298554-[1-Methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline

Produkt 1

HCID 23628207N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamideAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1,3,5-Trimethylpyrazole-4-carbonyl chloride (172 mg, 1 mmol), 4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline (329 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 ml), and the mixture was heated under reflux for 3 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. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2) to give the desired compound (360 mg).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 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=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-48a8c79875874ec7b35cc85610a1210d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404861B2

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