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

HRID 1952264

Reaktionsgleichung

Reaktionsgleichung von HRID 1952264
[H-].[Na+].[CH3:3][O:4][C:5]([C:14]1[C:19]([CH2:20][CH2:21][CH3:22])=[CH:18][C:17]([NH:23][C:24]([C:26]2[C:27]([CH3:33])=[N:28][N:29]([CH3:32])[C:30]=2[CH3:31])=[O:25])=[C:16]([CH3:34])[CH:15]=1)([C:10]([F:13])([F:12])[F:11])[C:6]([F:9])([F:8])[F:7].[C:35](OC(=O)C)(=[O:37])[CH3:36].Cl>O1CCCC1>[C:35]([N:23]([C:17]1[CH:18]=[C:19]([CH2:20][CH2:21][CH3:22])[C:14]([C:5]([O:4][CH3:3])([C:6]([F:9])([F:8])[F:7])[C:10]([F:13])([F:11])[F:12])=[CH:15][C:16]=1[CH3:34])[C:24]([C:26]1[C:27]([CH3:33])=[N:28][N:29]([CH3:32])[C:30]=1[CH3:31])=[O:25])(=[O:37])[CH3:36]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 23628207N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide

Produkt 1

HCID 86629857N-acetyl-N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (250 mg, 0.53 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of acetic anhydride (80 mg, 0.78 mmol) in tetrahydrofuran (2 ml) was added, and the mixture was stirred for one day. The reaction mixture was poured into diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over 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 (139 mg).

Aufarbeitung

  1. stirringthe mixture was stirred for one day
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over 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-0b048ce72b2a45008068e2adbcd3194e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404861B2

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