Methylamine → 2-(2,5-Dimethylthien-3-yl)-N-methylimidazo[2,1-b]-benzothiazole-3-acetamide

HRID 36912

Reaktionsgleichung

[CH3:1][C:2]1[S:3][C:4]([CH3:23])=[CH:5][C:6]=1[C:7]1[N:8]=[C:9]2[N:13]([C:14]=1[CH2:15][C:16]([OH:18])=O)[C:12]1[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=1[S:10]2.[CH3:24][NH2:25]>O1CCCC1>[CH3:1][C:2]1[S:3][C:4]([CH3:23])=[CH:5][C:6]=1[C:7]1[N:8]=[C:9]2[N:13]([C:14]=1[CH2:15][C:16]([NH:25][CH3:24])=[O:18])[C:12]1[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=1[S:10]2

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of 1.5 g (0.0044 mole) of 2-(2,5-dimethylthien-3-yl)imidazo[2,1-b]benzothiazole-3-acetic acid in 30 ml of anhydrous tetrahydrofuran is treated, at room temperature, with 0.85 g (0.005 mole) of N,N'-carbonyldiimidazole for 30 minutes. The solution which has become clear is cooled to 0° C. and a stream of methylamine is passed through it for 30 minutes. The mixture is allowed to return to room temperature, the stirring is continued for 3 h, the solvent is evaporated under reduced pressure, the residue is taken up in 10 ml of water, it is extracted with dichloromethane, the organic phase is separated, it is washed with water, it is dried over sodium sulphate, the solvent is evaporated under reduced pressure, and the residue is crystallized from ethyl acetate. 1 g of pale yellow crystals is finally obtained. Melting point: 238°-239° C.

Aufarbeitung

customto return to room temperature
customthe solvent is evaporated under reduced pressure
extractionit is extracted with dichloromethane
customthe organic phase is separated
washit is washed with water, it
dry with materialis dried over sodium sulphate
customthe solvent is evaporated under reduced pressure
customthe residue is crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-7156c0337bdd40d492d7eeed097f1fac
Quelldatensatz: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05418248

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