Process for producing 5-substituted oxazole compounds and...

Details Process for producing 5-substituted oxazole compounds and... Process for producing 5-substituted oxazole compounds and...

2002-03-20

2009-06-23

Seaman, D. Margaret (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S335100, C548S235000

Reissue Patent

active

RE040795

ABSTRACT:
A process for producing heterocyclic compounds which are useful as pesticides, drugs, fungicidal materials or intermediates thereof. TosMIC is reacted with an aldehyde or an imino compound: 1) in a solvent mixture of an aprotic solvent with a protic solvent in the presence of a base, 2) in the presence of a phase-transfer catalyst and an inorganic base, or 3) in the presence of an inorganic base. Thus, a desired product can be efficiently obtained using a solution without isolating TosMIC which is irritating and unstable, has a low decomposition point and shows explosivity.

REFERENCES:
patent: 4812473 (1989-03-01), Kuwano et al.
patent: 0 776 894 (1997-06-01), None
patent: 02-202871 (1990-08-01), None
Aldrich Chemical Catalogue, pertinent page listing Tosmic and references, p. 2351, Year 2007-2008. This NPL was filed Feb. 1, 2008.
Aldrich Chemical Catalogue, pertinent page listing Tosmic and references.
Bheemashankar A. Kulkarini and A. Ganesan, “Solution-phase Parallel Oxazole Synthesis with TosMIC,” Tetrahedron Letters, Institute of Moleular and Cell Biology, National University of Singapore (Singapore), p. 5637-5638.
UNK, “Synthesis of tosmic from sodium-p-toluene sulfinale by onc pot method,” p. 15-16, (Jan. 18, 1999).
B.A. Kulkami, A. Ganesan, “Solution-phase parallel oxazole synthesis with tosmic” Tetrahedron Letters, XP004171530, Nlelsevier Science Publishers (Amsterdam), vol. 40 (No. 30), p. 5637-5638 (1999).
Van Leusden, “Base-induced cycloaddition of sulfonylmethyl isocyanides to c,n double bonds,” Journal of Organic Chemistry XP-002322151, USAmerican Chemical Society (Easton), vol. 42 (No. 7), p. 1153-1159, (1977).

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