Synthesis of O-Benzoylthiamine Disulfide

In the course of studies on thiamine disulfide, a new compound, O-benzoylthiamine disulfide was synthesized by the oxidation of O-benzoylthiamine in alkaline solution or by the benzoylation of thiamine disulfide in pyridine. O-Benzoylthiamine disulfide occurs odorless, colorless prisms, m.p. 146-147°. Its infrared and ultraviolet spectra are shown in Chart I. On hydrolysis of O-benzoylthiamine disulfide with 10% hydrochloric acid, 4-amino-5-aminomethyl-4-methylpyrimidine, bis (1-acetyl-3-hydroxypropyl) disulfide, benzoic acid, and formic acid were formed.