Process for removing sulfonyl groups from benzimidazole isomers

Details Process for removing sulfonyl groups from benzimidazole isomers Process for removing sulfonyl groups from benzimidazole isomers

1983-03-21

1984-07-31

Ramsuer, Robert W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D23530

Patent

active

044631812

ABSTRACT:
This invention discloses a process for removing a sulfonyl group from the 1-position of a benzimidazole to allow conversion of 2-amino-1,5-substituted-benzimidazole compounds into 2-amino-1,6-substituted-benzimidazole compounds. The 5-isomer is reacted with an alkali metal hydroxide or carbonate in an inert aqueous organic solvent system. The reaction is acidified to precipitate the base and form the intermediate benzimidazole tautomer. The intermediate is then reacted with a sulfonyl acylating agent or a haloalkyl isothiocyanate to form a mixture of 2-amino-1,5(6)-substituted-benzimidazole compounds. This invention also discloses the same process for removing a sulfonyl group from the 1-position of a benzimidazole to allow conversion of 2-amino-1,6-substituted-benzimidazole compounds into 2-amino-1,5-substituted-benzimidazole compounds.

REFERENCES:
patent: 3825537 (1974-07-01), Haugwitz et al.
patent: 4008243 (1977-02-01), Wikel et al.
patent: 4018790 (1977-04-01), Paget et al.
patent: 4118573 (1978-10-01), Paget et al.
patent: 4118742 (1978-10-01), Paget et al.
patent: 4150028 (1979-04-01), Paget et al.
patent: 4174454 (1979-11-01), Paget et al.
patent: 4196125 (1980-04-01), Paget et al.
patent: 4216313 (1980-08-01), Paget et al.
patent: 4230868 (1980-10-01), Paget et al.
Sidgwick, The Organic Chemistry of Nitrogen, (1966) p. 251.
Smith, The Chemistry of Open-Chain Organic Nitrogen Compounds, vol. I, (1965) pp. 188-189.
Wright, Chem. Reviews, 48, 486-487 (1951).
Price, et al. "Some Sulfonamide Derivatives of 2-Aminobenzimidazole." J. Org. Chem. 12, 269-274 (1947).

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