The molecule itself is 5-Amino-2-Mercaptobenzimidazole. I want to do subsequent chemistry through Thiol group but I want to protect the amine group before.
I recommend you read the following article
Krzysztof Jarowicki and Philip Kocieński
, Protecting groups, Journal of the Chemical Society, Perkin Transactions 1, 1999, Issue 24, Page 3537 to 3733
Aniline or phenylamine is a primary amine which is usually protected by acetylation reaction whereby aniline acts as the nuclepohile and acyl (CH3CO-) group from acetic anhydride acts as the electrophile. Here, the hydrogen atom of –NH2 group is replaced by the acyl group as this equation shows for aniline “Ph-NH2”:
Ph-NH2 + CH3-CO-O-CO-CH3 → Ph-NH-CO-CH3 + CH3COOH
The main product is acetanilide “which is a solid that has a melting point around 114 oC”.
After the chemist does work on the molecules containing the “-NH-CO-CH3” group, the NH2 group can be regenerated by acidic hydrolysis of the former group into the latter.
2 Amino - 2 mercapto benzimidazole has primary secondary , and tertiary amino groups .
Perchloric acid adsorbed on silica-gel (HClO4–SiO2) was found to be a new, highly efficient, inexpensive and reusable catalyst for chemoselective N-tert-butoxycarbonylation of amines at room temperature and under solvent-free conditions.
A. K. Chakraborti, S. V. Chankeshwara, Org. Biomol. Chem., 2006, 4, 2769-2771.
An efficient and practical protocol allows the protection of various aryl and aliphatic amines using (Boc)2O in the presence of a catalytic amount of iodine under solvent-free conditions at ambient temperature.
R. Varala, S. Nuvula, S. R. Adapa, J. Org. Chem., 2006, 71, 8283-8286
This method is generally used for secondary amine's .
A catalyst-free N-tert-butyloxycarbonylation of amines in water gives N-t-Boc derivatives chemoselectively without any side products (such as isocyanate, urea, N,N-di-t-Boc). Chiral amines and esters of α-amino acids afforded optically pure N-t-Boc derivatives. Amino alcohols and 2-aminophenol afforded N-t-Boc protected derivatives without oxazolidinone formation.
S. V. Chankeshwara, A. K. Chakraborti, Org. Lett., 2006, 8, 3259-3262.
The amine is retrived back by acid hydrolysis
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