Process to prepare sulfonamides

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S085000, C564S086000, C564S087000, C564S088000, C564S089000, C564S090000, C564S091000, C564S092000, C564S093000, C564S094000, C564S095000, C564S096000, C564S097000, C564S098000, C564S099000

Reexamination Certificate

active

10296727

ABSTRACT:
A process for the preparation of a sulfonamide of formula (II), comprising reacting at elevated temperature an aniline of formula (I), with a sulfonating agent A of the formula R1—SO2-Z in the presence of a catalytic amount of either: (i) an amide B-1, other than N,N-dimethylformamide, or (ii) a high boiling tertiary amine B-2. Also provided in accordance with the present invention are processes for preparing sulfonamides of formula (II) by reacting an aniline of formula (I) with sulfanating agent A of the formula R1—SO2-Z in the presence of N,N-dimethylformamide, at a temperature in the range of about 120° C. to about 160° C. for about three to about seven hours. X, Y, Z, R and R1are defined herein

REFERENCES:
patent: 4818275 (1989-04-01), Theodoridis
patent: 5990315 (1999-11-01), Dumas
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Baltas, “Aminolysis of Sulphinamoyl-esters, -sulphonamides and -sulphones. Thiooxamate and thiourea formation via a sulphine intermediate. Thiophilic or carbophilic reaction?,” Elsevier Science Publishers (Amsterdam, NL), vol. 52 (No. 47), p. 14865-14876, (Nov. 18, 1996).
Ramon, “Camphorsulphonamide derivatives: a new class of chiral catalysts for the titanium alkoxide-promoted addition of dialkylzinc to aldehydes,” Elsevier Science Publshers (Amsterdam, NL), vol. 8 (No. 14), p. 2479-2496, (Jul. 24, 1997).

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