Ortho-[(alkylthio)(aminocarbonyl)methyl]anilines

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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26029373, 26032647, 260465D, 260559T, 544106, C07C10328

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active

040565696

ABSTRACT:
Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with .beta.-thio esters or .beta.-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho-[thioether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thioether (aminocarbonyl) alkyl]aniline, reacting the orthosubstituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.

REFERENCES:
patent: 3157650 (1964-11-01), Habicht
patent: 3825587 (1974-07-01), Diamond et al.
patent: 3897451 (1975-07-01), Gassman
patent: 3972894 (1976-08-01), Gassman
patent: 3985756 (1976-10-01), Gassman et al.
Gassman et al., J.A.C.S., 95:2, pp. 588-592 (Jan. 24, 1973).
Gassman et al., J.A.C.S., 95:8, pp. 2718-2719 (Apr. 18, 1973).
Gassman et al., J.A.C.S., 96:17, pp. 5508-5512 (Aug. 21, 1974).

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