Water → 2-propylthio-4-(3-trifluoromethyl-1H-triazolyl)benzonitrile

HRID 25285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25285
[F:1][C:2]([F:9])([F:8])[N:3]1[CH:7]=[CH:6][NH:5][NH:4]1.Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([S:19][CH2:20][CH2:21][CH3:22])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:20]([S:19][C:13]1[CH:12]=[C:11]([N:5]2[CH:6]=[CH:7][N:3]([C:2]([F:9])([F:8])[F:1])[NH:4]2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16])[CH2:21][CH3:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221709334-Chloro-2-n-propylthiobenzonitrileHCID 221709533-trifluoromethyl-1H-triazol

Produkt 1

HCID 221709562-propylthio-4-(3-trifluoromethyl-1H-triazolyl)benzonitrileAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.06 g (7.7 mmol) of 3-trifluoromethyl-1H-triazol, 1.38 g (6.5 mmol) of 4-chloro-2-n-propylthiobenzonitrile and 1.07 g (7.7 mmol) of potassium carbonate were stirred in 10 ml of N,N-dimethylformamide at 150° C. for 2 hours. The resulting reaction mixture was cooled to the room temperature and poured into 100 ml of water, and the organic matters were extracted with 50 ml of ethyl acetate twice. The ethyl acetate layers were combined, then washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.78 g of 2-propylthio-4-(3-trifluoromethyl-1H-triazolyl)benzonitrile. (yield 38.2%) as a milk-white powder (m.p. 143-144° C.).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionthe organic matters were extracted with 50 ml of ethyl acetate twice
  3. washwashed with 50 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customPurification of the residue by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-02522ae7d61640e1a8c8d31caf6319fd
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858639B2

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