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2-Mercaptothiazoline, is used in the chain-lengthening of alkyl halides by trans-iodopropenylenation. 2-Mercaptothiazoline is an antithyroid agent that strongly reduces thyroid hormone levels. 2-Mercaptothiazoline is also used as an intermediate in the preparation of biologically active compounds. It is also used as a tool for highly selective chiral synthesis of penam- and carbapenam-type β-lactam antibiotics.
Lei Tao et. al. Synthesis and bioactivity of poly(HPMA)-lysozyme conjugates: the use of novel thiazolidine-2-thione coupling chemistry. Organic & Biomolecular Chemistry. span>2009, 7,(17), 3481-3485 .
Newton L Dias Filho et. al. Preparation of a clay-modified carbon paste electrode based on 2-thiazoline-2-thiol-hexadecylammonium sorption for the sensitive determination of mercury. Analytical Sciences. span>2005, 21,(11), 1309-1316 .
Used in the chain-lengthening of alkyl halides by trans-iodopropenylenation: Org. Synth. Coll., 6, 704 (1988):
Reaction with ɑ-bromo esters gives the S-alkoxycarbonylmethyl derivatives, which can be C-alkylated by alkyl halides, using NaH as base. Sulfur-free products can be obtained by reduction (Zn/AcOH) to give the substituted acetic acid, or by reaction with iodidomethane to give the corresponding ɑ-iodo ester: Tetrahedron Lett., 2677 (1977).
Gefahrenhinweise (EU): H301
Toxic if swallowed.
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