Hydrochloric Acid → HCID 178418664, compound

Participants

Reaction Steps

In Scheme (3), 3-aminopyridine is acylated with di-t-butyldicarbonate to introduce the t-butoxycarbonyl (t-BOC) protecting group. (It will be appreciated that two other pyridinothiazolothio mercaptans may be prepared by known methodology using other amino pyridine isomers.) The t-BOC protected 3-aminopyridine is then treated with n-butyllithium in tetrahydrofuran followed by elemental sulfur (S8), followed by treatment with saturated ammonium chloride. The resulting 3-t-butoxycarbonylamino-4-thia-pyridine is treated with a mixture of acetic acid and HCl to provide 3-amino-4-mercaptopyridine hydrochloride. The desired 5-pyridinothiazolo thiomercaptan can then be prepared by treating this compound with carbon disulfide under basic conditions.

Provenance & Evidence