Process for the preparation of 2-chlorosulfinylazetidinone

Details Process for the preparation of 2-chlorosulfinylazetidinone Process for the preparation of 2-chlorosulfinylazetidinone

1993-04-21

1994-09-13

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540359, C07D205095, C07D50102

Patent

active

053470001

ABSTRACT:
A process for preparing a 2-chlorosulfinylazetidinone comprises heating in an inert organic solvent a penicillin sulfoxide ester, at a temperature between about 75.degree. C. and 140.degree. C., with an N-chlorohalogenating agent in the presence of a weakly basic N-alkali metal salt of a cyclic imide. The weakly basic N-alkali metal salt of a cyclic imide acts as an acid scavenger to bind the hydrogen chloride which is produced as a byproduct of the reaction. Preferably, the N-chlorohalogenating agent is N-chlorosuccinimide or N-chlorophthalimide, and the weakly basic N-alkali metal salt of a cyclic imide is the sodium or potassium salt of succinimide or phthalimide.

REFERENCES:
patent: 4052387 (1977-10-01), Kukolja
patent: 4075203 (1978-02-01), Chou
patent: 4081440 (1978-03-01), Kukolja
patent: 4165315 (1979-08-01), Kukolja
patent: 4165316 (1979-08-01), Chou
patent: 4289695 (1981-09-01), Chou
patent: 5053501 (1991-10-01), Kapur
patent: 5070195 (1991-12-01), Khanna et al.

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