Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-12-15
2000-07-18
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D26344
Patent
active
060909463
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for preparing a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative having a strong herbicidal effect.
BACKGROUND ART
As a process for preparing a 3-(substituted phenyl)-1,3-oxazolidine-2,4-dione derivative, the process which comprises reaction of an N-arylcarbamate with a 2-hydroxyalkanoate, if necessary, in the presence of a catalyst under heating [EP-A-0004582 (U.S. Pat. No. 4,220,787)] has been known so far. However, compounds having an alkylidene group at the 5-position can not be prepared by the process.
As a process for preparing a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative, the process which comprises reaction of a (substituted phenyl) isocyanate with a 2-hydroxy-3-alkenoate in the presence of a base followed by cyclization and isomerization of the double bond [WO 87/02357 (EP-A-0241559, U.S. Pat. No. 4,818,272, U.S. Pat. No. 4983751)] is known. However, the process is not thoroughly satisfactory as an industrial process because it is necessary to use phosgene or phosgene dimer, which is extremely dangerous to handle, for preparation of the isocyanate used as a starting material in this process.
DISCLOSURE OF INVENTION
The present inventors conducted extensive research in search of a process for efficiently preparing a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative having an alkylidene group at the 5-position without using dangerous phosgene or phosgene dimer, and have found that a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative can be prepared in a good yield by reaction of an N-(substituted phenyl)carbamate with a 2-hydroxy-3-butenoate under heating, if necessary, in the presence of a catalyst, that likewise, a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative can be prepared directly by reaction of an N-(substituted phenyl)carbamate with a 3-alkoxy-2-hydroxyalkanoate in the presence of a metallic compound as a catalyst under heating, and that the starting material, a 3-alkoxy-2-hydroxyalkanoate can be prepared by reaction of a glycidic ester with an alcohol in the presence of an acid catalyst. The present invention is accomplished on the basis of these discoveries.
The present invention provides a process for preparing a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative represented by general formula (III): ##STR2## (wherein Ar is a substituted phenyl group, and R.sup.2 and R.sup.3 are independently hydrogen atoms or alkyl groups having carbon numbers of from 1 to 12), which comprises reaction of an N-(substituted phenyl)carbamate represented by general formula (I): ##STR3## (wherein Ar is a substituted phenyl group, and R.sup.1 is an alkyl group having a carbon number of from 1 to 6 or a benzyl group) with a 2-hydroxy-3-alkenoate represented by general formula (II): ##STR4## (wherein R.sup.2 and R.sup.3 are independently hydrogen atoms or alkyl groups having carbon numbers of from 1 to 12, and R4 is an alkyl group having a carbon number of from 1 to 6) under heating.
The present invention also provides a process for preparing a 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivative represented by general formula (III): ##STR5## (wherein Ar is a substituted phenyl group, and R.sup.2 and R.sup.3 are independently hydrogen atoms or alkyl groups having carbon numbers of from 1 to 12), which comprises reaction of an N-(substituted phenyl)carbamate represented by general formula (I): ##STR6## (wherein Ar is the same as defined above, and R.sup.1 is an alkyl group having a carbon number of from 1 to 6 or a benzyl group) with a 3-alkoxy-2-hydroxyalkanoate represented by general formula (IV): ##STR7## (wherein R.sup.2 and R.sup.3 are the same as defined above, and R.sup.4 and R.sup.5 are independently alkyl groups having carbon numbers of from 1 to 6) in the presence of a metallic compound as a catalyst under heating.
Further, the present invention provides a process for prep
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patent: 4983751 (1991-01-01), Hirai et al.
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Juan Riego, Antonio Costa, and Jose Manuel, "Regioselective A1P0.sub.4 -A1.sub.2 0.sub.3 Promoted Ring-Opening of 2, 3-Epoxy Esters," Chemistry Letters, pp. 1565-1568, 1986 The Chemical Society of Japan.
Hirai Kenji
Imai Kiyomi
Masuda Katsuyuki
Matsukawa Tomoko
Mouri Takehito
Kaken Pharmaceutical Co., Ltd
Raymond Richard L.
Sagami Chemical Research Center
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