Cysteamine Hydrochloride → 2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

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Reaction Steps

To the solution from Example 13 above was added 56.7 g. of 2-aminoethanethiol, hydrochloride. The mixture was then heated and stirred, and distilled. The distillation was stopped when the pot temperature reached 133°, after 22 ml. of organic and 115 ml. of aqueous distillate had been received. To the residue remaining in the distillation flask was added 100 ml. of deionized water, 100 ml. of dichloromethane, and 100 ml. of 50% aqueous sodium hydroxide, dropwise with ice bath cooling. The mixture was then filtered, and the filter cake was washed with dichloromethane. The aqueous layer of the filtrate was extracted twice with 100 ml. portions of dichloromethane, and then the organic layers were combined, dried over sodium sulfate and filtered. The filtrate was evaporated to dryness under vacuum to obtain 97.7 g. of the desired product, which was identified as being 79.8% pure by gas chromatography, using a 2 mm. by 6-foot column of Gaschrom-Q (Applied Science Co.) containing 10% of OV-210 (Ohio Valley Chemical Co.) using 25 ml./min. of helium as the carrier at 170° isothermal.

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