Methyl iodide → HCID 4249922, Verbindung

HRID 1379798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379798
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH3:25]I>CN(C)C=O.Cl>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]=[C:10]2[N:14]([CH3:25])[C:13]([CH3:15])=[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[S:11]2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 748006HCID 748006, Verbindung

Produkt 1

HCID 4249922HCID 4249922, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

Ethyl 2-(4-cyanobenzoylamino)-4-methylthiazole-5-carboxylate (22.07 g) was added to a suspension of 60% oily sodium hydride (3.08 g) in N,N-dimethylformamide (hereinafter referred to as DMF) (300 ml) under ice-cooling, followed by stirring at room temperature for an hour. A solution of methyl iodide (4.8 ml) in DMF (50 ml) was added dropwise to the reaction mixture, followed by further stirring at room temperature for an hour. The reaction mixture was taken up in 3% hydrochloric acid, and the precipitated crystals were collected by filtration, and the resulting crude crystals were recrystallized from a mixture of methylene chloride and methanol to give ethyl 2-(4-cyanobenzoylimino)-3,4-dimethylthiazoline-5-carboxylate (15.97 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringby further stirring at room temperature for an hour
  3. filtrationthe precipitated crystals were collected by filtration
  4. customthe resulting crude crystals were recrystallized from a mixture of methylene chloride and methanol

Quellen und Nachweise

ORD-Eintrag
ord-3c8b8831815542e88df04da1e28fbbc0
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672712

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