Dimethylformamide → 1-(6-Methylergolin-8beta-ylmethyl)-1,2,4-triazole

HRID 986528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986528
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.CN(C)C=O.S(C1C=CC(C)=CC=1)(O[CH2:17][C@@H:18]1[CH2:32][C@H:31]2[C@@H:21]([CH2:22][C:23]3[C:33]4[C:26](=[CH:27][CH:28]=[CH:29][C:30]2=4)[NH:25][CH:24]=3)[N:20]([CH3:34])[CH2:19]1)(=O)=O>O>[CH3:34][N:20]1[C@H:21]2[C@@H:31]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:33]=3[C:23]([CH2:22]2)=[CH:24][NH:25]4)[CH2:32][C@@H:18]([CH2:17][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)[CH2:19]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Produkt 1

HCID 98885351-(6-Methylergolin-8beta-ylmethyl)-1,2,4-triazoleAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

0.4 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.0 g of 1,2,4-triazole and 20 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 1 hour. After allowing the mixture to cool, water was added to the reaction mixture, and the precipitated crystals were separated by filtration, washed with water and purified by alumina column chromatography (eluted with dichloromethane). The product was recrystallized from methanol to obtain 0.8 g of the titled compound as colorless needles having a melting point of 245°-253° C.

Aufarbeitung

  1. temperaturewas then heated on a water bath for 1 hour
  2. temperatureto cool
  3. customthe precipitated crystals were separated by filtration
  4. washwashed with water
  5. custompurified by alumina column chromatography (eluted with dichloromethane)
  6. customThe product was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-d6f5eb6e92eb44df8d9baf2b6f9cc0cc
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04713457

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