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Triethylamine → HCID 12115480, Verbindung

HRID 2373331
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2373331
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([OH:10])=O)[C:4]([CH3:11])=[N:3]1.[CH3:12][CH:13]([C:18]1[CH:24]=[C:23]([C:25]([O:34][CH3:35])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])[CH:22]=[CH:21][C:19]=1[NH2:20])[CH2:14][CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C>S(Cl)(Cl)=O.O1CCCC1.C(OCC)(=O)C>[CH3:12][CH:13]([C:18]1[CH:24]=[C:23]([C:25]([O:34][CH3:35])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])[CH:22]=[CH:21][C:19]=1[NH:20][C:8]([C:5]1[C:4]([CH3:11])=[N:3][N:2]([CH3:1])[C:6]=1[CH3:7])=[O:10])[CH2:14][CH:15]([CH3:16])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 7365141,3,5-trimethyl-1H-pyrazole-4-carboxylic acidHCID 12115479HCID 12115479, Verbindung

Produkt 1

HCID 12115480HCID 12115480, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel
HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

1,3,5-Trimethylpyrazole-4-carboxylic acid (154 mg, 1 mmol) was dissolved in thionyl chloride (5 ml), and the solution was heated under reflux for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting acid chloride was added to a solution of 2-(1,3-dimethylbutyl)-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-aniline (345 mg, 1 mmol) and triethylamine (150 mg, 1.5 mmol) in tetrahydrofuran (10 ml) under ice-cooling, after which the resulting mixture was heated under reflux for 2 hours. The reaction mixture was diluted with ethyl acetate and then washed with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel column chromatography. (hexane:ethyl acetate 1:2) to obtain 200 mg of the desired compound.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. temperaturecooling
  5. temperatureafter which the resulting mixture was heated
  6. temperatureunder reflux for 2 hours
  7. washwashed with water
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe resulting residue was separated
  11. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b6c3f9bb0a3949b5ae6bd8dd67d58466
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07459477B2

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