Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1996-12-13
1998-09-22
Lambkin, Deborah C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
C07C25510
Patent
active
058115714
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This application is a 371 of PCT/JP 95/02675 filed on Dec. 12, 1995.
The present invention relates to a novel process for preparing aromatic or heteroaromatic sulfonyl halides. Aromatic or heteroaromatic sulfonyl halides are useful compounds which are used in various applications as pharmaceuticals, agricultural chemicals, functional materials or the like.
BACKGROUND ART
Many processes have been known for preparing aromatic sulfonyl halides. These processes are classified as follows.
(A) Process involving sulfonation Synth., I,84 (1941) ##STR1## Sulfonation with chlorosulfuric acid or the like M. S. Morgan, L. H. Cretcher, J. Am. Chem. Soc., 70.375 (1948) ##STR2##
(B) Process involving formation of diazonium salt ##STR3##
(C) Process utilizing metallization reaction ##STR4##
(D) Process involving chlorination of thiol derivative ##STR5##
However, these known processes entail the following drawbacks when industrially carried out.
In the process (A), it is difficult to conduct a reaction in case of an aromatic ring having a nitro group, a cyano group, a carboxyl group or the like attached thereto or in case of a pyridine ring. In this process, generally at least two halogenated sulfonyl groups can not be easily introduced into one aromatic ring.
The process (B) tends to involve a lengthy procedure and poses a problem about the disposal of waste water which arises from the use of a large amount of copper salt. Thus the process is undesirable from the viewpoints of economy and protection of environment. Further, a diazonium salt itself is far from being stable and problematic as to safe operation.
The process (C) if industrially practiced does not economically pay in many instances because of a low yield and an expensive reagent used.
In the process (D), an aromatic substituted thiol derivative to be used as the raw material is often difficult to obtain at low costs on an industrial scale.
As described above, conventional processes for preparing aromatic sulfonyl halides are uneconomical and are not easy to industrially carry out in most cases. Consequently there has been a demand for processes capable of industrially manufacturing various aromatic sulfonyl halide derivatives at low costs.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to provide a process for preparing an aromatic or heteroaromatic sulfonyl halide industrially at low costs and with ease.
The present inventors conducted extensive research to overcome the foregoing prior art drawbacks and to provide a process for preparing an aromatic or heteroaromatic sulfonyl halide industrially at low costs and with ease.
The finding was that the contemplated aromatic or heteroaromatic sulfonyl halides can be produced in high yields when using an aromatic or heteroaromatic sulfide or an aromatic or heteroaromatic sulfoxide as the raw material and halogenating said compound in the presence of water. The present invention was completed based on this novel finding.
While the reaction mechanism remains to be clarified, it is presumed that a bond between the sulfur atom and the carbon atom of methyl group in the aromatic or heteroaromatic methyl sulfide or the aromatic or heteroaromatic methyl sulfoxide used as the raw material is selectively and easily split, and the oxidation or halogenation of the sulfur atom occurs substantially coincidentally.
The first invention of the present application provides a novel process for preparing an aromatic or heteroaromatic sulfonyl halide represented by the formula (3), the process comprising halogenating an aromatic or heteroaromatic methyl sulfide represented by the formula (1) shown below with a halogenating agent in the presence of water unsubstituted or which has an optional substituent or substituents, X and Y are halogen atoms, m is an integer of 0 to 3 and n is 1 or 2.
The second invention of the present application provides a novel process for preparing an aromatic or heteroaromatic sulfonyl halide represented by the formula (3), the process comprising halogenatin
REFERENCES:
Oxidative Chlorination of --Halogenosulphides as a Synthetic Route to --Halogenosulphoxides, Sulphinyl Chlorides, and Sulphonyl Chlorides by J.S. Grossert, et al. J. Chem. Soc., Chem. Commun. 1973, No. 2, p.50.
Goda Hiroshi
Karino Hitoshi
Nishiguchi Hideaki
Sakamoto Jun-ichi
Yoshida Katsuhiko
Lambkin Deborah C.
Sackey Ebenezer O.
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