Triethylamine → N-Des(isobutyraldehyde) Pyflubumide

HRID 1952265

Reaktionsgleichung

Reaktionsgleichung von HRID 1952265
[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[C:23]([O:32][CH3:33])([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[C:23]([O:32][CH3:33])([C:24]([F:27])([F:25])[F:26])[C:28]([F:29])([F:30])[F:31])[CH:13]([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 13637622trimethyl-1H-pyrazole-4-carbonyl chlorideHCID 866190033-Isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

Produkt 1

HCID 86629858N-Des(isobutyraldehyde) PyflubumideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1,3,5-trimethylpyrazole-4-carbonyl chloride (3.93 g, 22.8 mmol), 3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (5.0 g, 15.2 mmol), and triethylamine (3.07 g, 30.4 mmol) were dissolved in tetrahydrofuran (100 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. The obtained crude crystals were washed with ether to give the desired compound (5.62 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 crude crystals
  7. washwere washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-fc21d52197af4bf697b743186097cfcb
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404861B2

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