Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1998-12-23
2000-11-14
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 13, C07C30340, C07C31118
Patent
active
061472484
DESCRIPTION:
BRIEF SUMMARY
The invention relates to the technical field of the intermediates for the preparation of active compounds, in particular of herbicidal sulfonylureas.
It is known that ureas of the formula aryl-SO.sub.2 --NH--CO--NH--R, where aryl is an aryl radical with or without substitution and R is an alkyl radical, can in principle be reacted with phosgene to give the corresponding isocyanates of the formula aryl-SO.sub.2 --NCO which in turn can be employed for preparing herbicidally active sulfonylureas (EP-A-0584043; U.S. Pat. No. 4,566,898). To be able to apply the general method to the preparation of sulfonylureas of the series aryl=2-carbomethoxy-5-iodophen-1-yl, which are useful herbicidal sulfonylureas (WO-A-92/13845), it was the object to provide compounds of the formula (I) ##STR5## in which R is alkyl or cycloalkyl, each of the last two radicals being unsubstituted or substituted. Preferably, the object was to provide an effective process for preparing compounds of the formula (I).
Surprisingly, it is possible, as discussed in more detail below, to obtain the compounds of the formula (I) starting from compounds of the formula (II) via the intermediates (III) and (IV) in very good yields. The invention thus permits an effective preparation of herbicidal sulfonylureas and other active compounds.
The invention relates to a process for preparing N-substituted methyl 4-iodo-2-[N-(aminocarbonyl)aminosulfonyl]benzoates of the formula (I) ##STR6## in which R is alkyl or cycloalkyl, each of the last two radicals being unsubstituted or substituted, and substituted by one or more radicals selected from the group consisting of halogen, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.6)haloalkoxy and phenyl with or without substitution, or is (C.sub.3 -C.sub.12)cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)haloalkoxy and (C.sub.1 -C.sub.6)alkylthio, which comprises ##STR7## in the presence of an acid H.sup.+ X.sup.- where X.sup.31 is an equivalent of an anion, for example X.sup.- =Cl.sup.-, I.sup.- or HSO.sub.4.sup.-, to give a compound (diazonium salt) of the formula (III) ##STR8## in which X.sup.- has the same meaning as in the acid H.sup.+ X.sup.-, and (b) reacting the compound of the formula (III), after its isolation or, preferably, without isolation, in the presence of iodide ions to give a compound of the formula (IV) ##STR9## and c) reacting the compound of the formula (IV) with an isocyanate of the formula (V) formula (I).
The invention furthermore provides individual steps of the process.
In the formula (I) and in the formulae used hereinbelow, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy and alkylthio and the corresponding substituted radicals may in each case be straight-chain or branched in the carbon skeleton. Unless specifically mentioned, the lower carbon skeletons, for example those having 1 to 4 carbon atoms, are preferred for these radicals. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyls, 1-methylhexyl and 1,4-dimethylpentyl. Cycloalkyl is a carbocyclic saturated ring system, for example having 3 to 8 ring atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example CF.sub.3, CHF.sub.2, CH.sub.2 F, CF.sub.3 CF.sub.2, CH.sub.2 FCHCl.sub.2, CCl.sub.3, CHCl.sub.2, CH.sub.2 CH.sub.2 Cl; haloalkoxy is, for example, OCF.sub.3, OCHF.sub.2, OCH.sub.2 F, CF.sub.3 CF.sub.2 O, OCH.sub.2 CF.sub.3 and OCH.sub.2 CH.sub.2
REFERENCES:
patent: 4383113 (1983-05-01), Levitt
patent: 4566898 (1986-01-01), Reap
patent: 5463081 (1995-10-01), Ort et al.
The Journal of the American Chemical Society, vol. 55, (1933), pp. 1649-1654.
Knorr Harald
Willms Lothar
Hoechst Schering AgrEvo GmbH
O'Sullivan Peter
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