Methane → N-(6-methylergolin-8beta-ylmethyl)succinimide

HRID 986530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986530
[H-].[Na+].[C:3]1(=[O:9])[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.S(C1C=CC(C)=CC=1)(O[CH2:14][C@@H:15]1[CH2:29][C@H:28]2[C@@H:18]([CH2:19][C:20]3[C:30]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]2=4)[NH:22][CH:21]=3)[N:17]([CH3:31])[CH2:16]1)(=O)=O.C>C(O)C.CN(C)C=O>[CH3:31][N:17]1[C@H:18]2[C@@H:28]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:30]=3[C:20]([CH2:19]2)=[CH:21][NH:22]4)[CH2:29][C@@H:15]([CH2:14][N:7]2[C:6](=[O:8])[CH2:5][CH2:4][C:3]2=[O:9])[CH2:16]1

Komponenten

7

Edukt 4

HCID 297MethaneHCID 11439SuccinimideHCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Produkt 1

HCID 10246462N-(6-methylergolin-8beta-ylmethyl)succinimideAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.8 g of 50% sodium hydride in an oil was added in small portions to a mixture of 3.4 g of succinimide and 50 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 30 minutes. The solvent was distilled off under reduced pressure, and water was added to the residue. The precipitated crystals were separated by filtration, and washed with water. The crystals thus obtained were treated with charcoal in ethanol and recrystallized from ethanol to obtain 0.9 g of the titled compound as colorless needles having a melting point of 233°-238° C. (with decomposition).

Aufarbeitung

  1. temperaturewas then heated on a water bath for 30 minutes
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. customThe precipitated crystals were separated by filtration
  5. washwashed with water
  6. customThe crystals thus obtained
  7. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ea454ccb77b3439989efa0917448d450
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04713457

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