N-NO formation in 2-mercaptobenzothiazole

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Dear All,

I have one query . 2-mercaptobenzothiazole can exist in tautomerism . In tautomerism stage, can its NH form N-No , As per literature, i understand that due to presence of Sulfur, it will form S-No and then proceed for S-S (Sulfide) dimer .Can you please check and share your comment on it .

Thanks ,

Amit

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2‑Mercaptobenzothiazole (MBT) undergoes thione–thiol tautomerism, i think this does not generate a reactive secondary amine capable of forming an N‑nitrosamine. The nitrogen present in the thione form is part of an aromatic heterocycle and is strongly deactivated toward nitrosation, meaning N‑nitrosamine formation is not chemically feasible. At most, the thiol tautomer could undergo S‑nitrosation, which may produces S‑nitrosothiol - not an N‑nitrosamine and not classified as a nitrosamine impurity!

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Dear Umesh ,

Thanks for your explanation and help on it .

Amit

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