Dimethylformamide → HCID 19936722, Verbindung

HRID 36913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 36913
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3=[N:10][C:11]([C:20]4[CH:24]=[C:23]([CH3:25])[S:22][C:21]=4[CH3:26])=[C:12]([CH:13](O)[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[N:7]3[C:6]=2[CH:27]=1.S(Cl)([Cl:30])=O.CN(C)C=O>ClCCl>[ClH:1].[Cl:30][CH:13]([C:12]1[N:7]2[C:8]([S:9][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][C:6]=32)=[N:10][C:11]=1[C:20]1[CH:24]=[C:23]([CH3:25])[S:22][C:21]=1[CH3:26])[C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 199367056-chloro-alpha-hydroxy-N,N-dimethyl-2-(2,5-dimethylthien-3-yl)imidazo[2,1-b]benzothiazole-3-acetamide

Produkt 1

HCID 19936722HCID 19936722, VerbindungAusbeute 205,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

18 g (0.0431 mole) of 6-chloro-α-hydroxy-N,N-dimethyl-2-(2,5-dimethylthien-3-yl)imidazo[2,1-b]benzothiazole-3-acetamide are treated with 31 ml (0.43 mole) of thionyl chloride, 2 ml of N,N-dimethyl formamide and 100 ml of dichloromethane at the reflux temperature for 6 h. The solvent and the excess thionyl chloride are removed under reduced pressure, the residue is taken up in diethyl ether, the solid is washed with diethyl ether and it is dried. 21 g of α,6-dichloro-N,N-dimethyl-2-(2,5-dimethylthien-3-yl)imidazo[2,1-b]benzothiazole-3-acetamide hydrochloride are obtained which are reduced with 21 g (0.136 mole) of Rongalite® in 300 ml of dichloromethane at room temperature for 24 h. The solution is separated after settling has taken place, the solid is washed with dichloromethane, the organic phase is washed with a saturated sodium hydrogen carbonate solution and then with water, it is dried over sodium sulphate and the solvent is evaporated under reduced pressure. An oil is obtained which crystallizes and which is recrystallized from acetonitrile. 14.4 g of yellow needles are finally isolated. Melting point: 202°-203° C.

Aufarbeitung

  1. customThe solvent and the excess thionyl chloride are removed under reduced pressure
  2. washthe solid is washed with diethyl ether and it
  3. customis dried

Quellen und Nachweise

ORD-Eintrag
ord-b5cf16699b15485896e46c2aceaeb875
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418248

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