Methyl iodide → 2-Amino-4-[4-(2-diethylaminoethoxy)phenyl]imino-8-methoxy-4H-1,3,5-triazino[2,1-b]benzothiazole

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Reaction Steps

6-Methoxybenzothiazol-2-ylguanidine (0.2 g) was added to a suspension of sodium hydride (0.022 g=0.044 g of 50% dispersion in oil) in anhydrous dimethylformamide (20 mls) and the resulting mixture was stirred at room temperature for 15 mins. 4-(2-Diethylaminoethoxy)phenylisothiocyanate (0.23 g) was added followed, after 2.5 hrs, by methyl iodide (0.14 g) and the mixture stirred for a further 18 hrs. Water was added to precipitate a yellow solid which was collected by filtration, washed with ethanol and dissolved in ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulphate and evaporated to give a yellow solid (0.33 g). Recrystallisation of the residue from ethyl acetate gave the desired product as pale yellow crystals (0.08 g) mp 189.5°-191°.

Provenance & Evidence