Hydrochloric Acid → 2-[(4-Hydroxyphenyl)thio]ethylamine hydrochloride

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A mixture of 4-hydroxythiophenol (2.48 g, 19.7 mmol) and 2-methyl-2-oxazoline (1.67 g, 1.69 mL, 19.7 mmol) were refluxed (neat) under argon for two hours. Upon cooling, the crude sticky solid was re-suspended in concentrated hydrochloric acid (aq) and refluxed for 12 hours. The mixture was then poured into water (20 mL) and extracted with diethyl ether (2×20 mL). The aqueous liquors were concentrated to dryness and twice re-dissolved in water and re-concentrated. Re-crystallisation of the resultant solid (ethanolidiethyl ether) gave the product as a cream solid (0.45 g, 11%); m.p. 130–31 ° C. (lit.11 128–29° C.); 1H (400 MHz, D2O) δ 3.07 (4H, br s, 2×CH2), 6.87 (2H, d, J 11.9 Hz, Ar), 7.41 (2H, d, J 11.9 Hz, Ar)

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