Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1995-11-08
1998-05-12
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
568 65, 568 67, C07C32128
Patent
active
057507635
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to processes for producing alkoxycarbonylalkylthioaryl compounds useful as an intermediate for herbicide synthesis, and related compounds thereof.
BACKGROUND ART
A process for production of an arylmercaptan compound is known which comprises reducing an aryl disulfide compound with an iron powder or a zinc powder. This process, however, is troublesome in the disposal of the iron powder or zinc powder used. A process for production of an aryl mercaptan compound from a disulfide compound using an alkali hydroxide, is advantageous in that the process can be carried out under relatively mild reaction conditions. The process, however, has a drawback in that the yield of arylmercaptan compound (an intended product) is low because the product is partially oxidized to generate by-products such as arylsulfinic acid and the like; thus, the process has been unsuitable as an intermediate step for production of an alkoxycarbonylalkylthioaryl compound.
A 2,4-dihalo-5-methoxycarbonylthioaniline derivative obtained from 5,5'-(2,4-dihalogenoaniline) disulfide (which is an aryl disulfide compound above mentioned) represented by the following general formula: ##STR4## is unstable and cannot be isolated at a high yield. Thus, it has been difficult to produce, in industry, an intended alkoxycarbonylalkylthioaryl compound from a substituted aryldisulfide compound which is an expensive raw material.
The task to be achieved by the present invention is to provide industrial processes for producing a metal salt of an arylmercaptan compound and an alkoxycarbonylalkylthioaryl compound in an easy operation at a high yield.
In order to achieve the above task, the present inventors made a study hardly on a process for producing an alkoxycarbonylalkylthioaryl compound. As a result, the present inventors unexpectedly found out that by allowing a sulfur compound to be present in the reaction of an aryl disulfide compound with an alkali metal hydroxide, the aryl disulfide compound can be converted into an alkali metal salt of a corresponding arylmercaptan compound at a high yield, that by reacting said alkali metal salt with a halogenofatty acid ester compound at pH 7-10, said alkali metal salt can be converted into an alkoxycarbonylalkylthioaryl compound easily at a high yield, and that these reactions can be carried out continuously in the same reactor. The present invention has been completed based on the above findings.
DISCLOSURE OF THE INVENTION
The present invention provides:
a process for producing an alkali metal salt of an arylmercaptan compound, represented by general formula (3): ##STR5## (wherein R.sup.1 s are each a hydrogen atom, a halogen atom, an amino group, an acylamino group, an alkyl group, an alkoxy group, a phenyl group, an alkylamino group, a dialkylamino group, a benzyl group or an acyl group; n is an integer of 1-5; when n is 2 or more, R.sup.1 s may be the same or different; M.sup.1 is an alkali metal), which process comprises reacting a disulfide compound represented by general formula (1): ##STR6## wherein R.sup.1 s and n have the same definitions as given above) with a hydroxide of an alkali metal M.sup.1 in the presence of a sulfur compound represented by general formula (2): integer of 1 or 2);
a process for producing an alkoxycarbonylalkylthioaryl compound represented by general formula (5): ##STR7## (wherein R.sup.1 s and n have the same definitions as given above; R.sup.2 is an alkylene group; R.sup.3 is an alkyl group), which process comprises reacting an alkali metal salt of an arylmercaptan compound, represented by general formula (3): ##STR8## (wherein R.sup.1 s, n and M.sup.1 have the same definitions as given above) with a halogenofatty acid ester compound represented by general formula (4): X.sup.1 is a halogen atom) at pH 7-10; and
a process for producing an alkoxycarbonylalkylthioaryl compound represented by general formula (5): ##STR9## (wherein R.sup.1 s, n, R.sup.2 and R.sup.3 have the same definitions as given above), which process comprises
REFERENCES:
patent: 3116321 (1963-12-01), Horn
CA: 112:206573 Abst 1990 oxidation of thiots to disulfides.
Aldrich 1996 p. 1415 & p. 1436 Catalogue.
"Synthetic Methods of Organic Chemistry" (W-Theilheimer) W Theilheimer vol. 6 660-(1952).
"Synthetic Methods of Organic Chemistry" vol. 8 38-39 (1954).
Aldrich Catalog 1996-1997-p. 1418.
Nakayama Tadashi
Sugiyama Tatsuo
Ihara Chemical Industry Co. Ltd.
Ivy C. Warren
Vollano Jean F.
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