Process for the synthesis of 3-chlorobenzo[b]thiophene-2-carbony

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549 58, 549 56, C07D33356, C07D33322

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054261910

ABSTRACT:
An improved process for the preparation of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides is described where a cinnamic acid is converted in the presence of thionyl chloride and a 4-N,N'-disubstituted aminopyridine in one step to the desired product.

REFERENCES:
patent: 4530929 (1985-07-01), Butler et al.
patent: 5210205 (1993-05-01), Hubele
Higa et al, Oxidation by Thionyl Chloride. VI. Mechanism of Reaction with Cinnamic Acids, J. Org. Chem., vol. 40, No. 21, 1975 (3037-3045).
Haslam, Recent Developments in Methods for the Esterification and Protection of the Carboxyl Group, Tetrahedron, vol. 36, pp. 2409-2433, 1980.
J. of Medicinal Chemistry, 35:958-965 (1992) D. T. Connor, et al.
J. of Heterocyclic Chemistry, 8:711-714 (1971) Wright, W. B., Jr., and Brabander, H. J.
J. of Heterocyclic Chemistry, 23:1571-1577 (1986) Pakray, S. and Castle, R. N.

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