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1H-1,2,4-Triazole → HCID 23039725, Verbindung

HRID 2166413
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2166413
S([O-])(=O)(=O)C.CS(O[CH2:11][C:12]([O:24][CH2:25][CH3:26])([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[CH2:13][CH2:14][CH3:15])(=O)=O.[Na].[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CO>[N:28]1([CH2:11][C:12]([O:24][CH2:25][CH3:26])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[CH2:13][CH2:14][CH3:15])[CH:32]=[N:31][CH:30]=[N:29]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 92571H-1,2,4-Triazole2×HCID 85257MethanesulfonateHCID 5360545Sodium2×HCID 23039727HCID 23039727, Verbindung

Produkt 1

HCID 23039725HCID 23039725, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The mesylate prepared in accordance with (a) is reacted with the sodium salt of 1,2,4-triazole. This is effected by dissolving 0.83 g of sodium in 30 ml of methanol, adding 2.5 g of 1,2,4-triazole and removing the solvent in vacuo. A solution of 8.55 g of the mesylate in 30 ml of dimethyl sulfoxide is added to the residual sodium salt. After being heated for 5 hours on a bath at 120° C., the mixture is cooled to room temperature and extracted with diethyl ether. The combined extracts are washed with water, dried over sodium sulfate and concentrated in vacuo. Yield of crude product 7.6 g. The crude product is purified by column chromatography (silica gel; 1:4 ethyl acetate/petroleum ether) and affords a colourless oil, which crystallises after a few days. Recrystallisation from 16 ml of petroleum ether gives 3.7 g of the end product. Melting point 67° C. 100 MHz-1H-NMR (CDCl3): δ=7.63 and 7.72 ppm (s, 2H of triazole); 7.0-7.4 ppm (m, 3H, aromatic); 4.8 ppm (m, 2H, --CH2N); 3.2-3.8 ppm (m, 2H, --OCH2 --CH3); 1.7-2.4 ppm (m, 2H, --CH2CH2CH3); 1.3 ppm (t, 3H, --OCH2CH3); 0.7-1.4 ppm (m, 5H, --CH2CH2CH3).

Aufarbeitung

  1. customremoving the solvent in vacuo
  2. additionA solution of 8.55 g of the mesylate in 30 ml of dimethyl sulfoxide is added to the residual sodium salt
  3. temperaturethe mixture is cooled to room temperature
  4. extractionextracted with diethyl ether
  5. washThe combined extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by column chromatography (silica gel; 1:4 ethyl acetate/petroleum ether)
  9. customaffords a colourless oil, which
  10. customcrystallises after a few days
  11. customRecrystallisation from 16 ml of petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-f1c1c9340a824b388f3bae5f1ca5112f
Quelldatensatz
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04945100

Notizen zur Reaktion

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