Acetone → 3'-[1-Hydroxy-2-(2-imino-3-thiazolidinyl)ethyl]acetanilide hydrochloride

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Reaction Steps

To a stirred slurry of 63.47 g. (0.177 mole) of 3'-[(2-imino-3-thiazolidinyl)acetyl]acetanilide hydrobromide (Example 3) in 1 liter of 95% ethanol, maintained at 5° C., is added 5.70 g. (0.15 mole) of sodium borohydride. After stirring 40 minutes an additional 4.10 g. of sodium borohydride is added and the mixture is acidified with hydrochloric acid and evaporated under reduced pressure. The residue is partitioned between chloroform and dilute aqueous ammonium hydroxide. Two further chloroform extracts are combined with the original, washed with brine, dried (sodium sulfate) and evaporated to give an oil. Treatment with acetone gives 26.77 g. (48%) of white crystalline hydrochloride, which has melting point 235°-237° C. Anal: Calcd. for C13H18CIN3O2S:x Calcd: C, 49.44; H, 5.74; Cl, 11.23; N, 13.31; S, 10.15. Found: C, 49.87; H, 5.27; Cl, 11.51; N, 13.25; S, 10.40.

Provenance & Evidence