Process for preparing substituted aryluracils

Details Process for preparing substituted aryluracils Process for preparing substituted aryluracils

1997-10-27

1998-12-08

Ford, John M.

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544312, C07D23954

Patent

active

058471375

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/EP96/01669, filed Apr. 22, 1996. The invention relates to a novel process for preparing substituted aryluracils known as herbicidally active compounds.
It is known that certain substituted aryluracils such as, for example, 1-(4-cyano-2-fluoro-5-ethylsulfonylamino-phenyl)-3,6-dihydro-2,6-dioxo-4-t rifluoromethyl-1 (2H)-pyrimidine are obtained when ethyl 3-amino-4,4,4-trifluoro-crotonates are reacted with sodium hydride in dimethylformamide/toluene and then with 4-cyano-2,5-difluorophenyl isocyanate and the thus-obtained 1-(4-cyano-2,5-difluoro-phenyl)-3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1( 2H)-pyrimidine is reacted with ethanesulfonamide (cf. DE 4412079).
In this preparation, sodium hydride, which is not very suitable for industrial processes, is employed as acid acceptor, and the reaction is carried out as a multi-step reaction.
It has now been found that substituted aryluracils of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or halogen, alkyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, the general formula (II) ##STR2## in which R.sup.4 and R.sup.5 are each as defined above and (III) ##STR3## in which R.sup.1 and R.sup.2 are each as defined above, in the presence of an aprotic polar solvent at temperatures between -20.degree. C. and +150.degree. C. ("step one") ##STR4## in which R.sup.1, R.sup.2, R.sup.4, R.sup.5 and X are each as defined above, are then--if appropriate after intermediary isolation--reacted with sulfonamides of the general formula (IV) an aprotic polar solvent at temperatures between 20.degree. C. and 200.degree. C., if appropriate under an atmosphere of inert gas ("step 2").
Surprisingly, the substituted aryluracils of the general formula (I) can be prepared by the process according to the invention in good yields and in high purity in a simpler manner than by the known prior art.
The process according to the invention thus represents a valuable advance on the prior art.
The process according to the invention preferably relates to the preparation of compounds of the formula (I) in which optionally fluorine- and/or chlorine-substituted alkyl having 1 to 4 carbon atoms, bromine- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkenyl or alkinyl having in each case up to 6 carbon atoms, represents respectively optionally cyano-, fluorine-, chlorine-, bromine- or C.sub.1 -C.sub.4 -alkyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety and optionally 1 to 4 carbon atoms in the alkyl moiety, represents aryl or arylalkyl having 6 or 10 carbon atoms in the aryl moiety and optionally 1 to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, by respectively optionally fluorine- and/or chlorine-substituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfinyl or C.sub.1 -C.sub.4 -alkylsulfonyl, by dimethylaminosulfonyl or diethylaminosulfonyl, by optionally fluorine-, chlorine-, bromine-, cyano-, methoxy- or ethoxy-substituted C.sub.1 -C.sub.4 -alkoxy-carbonyl, or by respectively optionally fluorine-, chlorine-, bromine-, cyano-, methyl-, methoxy-, trifluoromethyl- and/or trifluoromethoxy-substituted phenyl, phenyloxy or phenylthio, fluorine- and/or chlorine-substituted alkyl having 1 to 6 carbon atoms and ethoxy-substituted alkyl having 1 to 6 carbon atoms.
The process according to the invention in particular relates to the preparation of compounds of the formula (I) in which methyl or trifluoromethyl, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethenyl, propenyl, butenyl, ethinyl, propinyl or butinyl, represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents phenyl, naphthyl, benzyl or phenyleth

REFERENCES:
Valkanas et al, J. Amer. Chem. Soc. pp. 1123, 1124, & 1125 (1963).

Affiliated with

Also associated with

Rating

Process for preparing substituted aryluracils does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing substituted aryluracils, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing substituted aryluracils will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-178734