Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1999-06-09
2000-10-24
McKane, Joseph K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
558 44, 558418, C07D23902, C07C25500
Patent
active
061369756
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a novel process for preparing trifluoroacetoacid-anilides which can be used as intermediates for preparing herbicidally active uracil derivatives.
BACKGROUND OF THE INVENTION
It is already known that N-aryl-trifluoroacetoacet-amides can be prepared by reacting trifluoroacetoacetic ester with aryl amines (cf. DE-A 42 18 159, EP-A 0 598 436 and J. Het. Chem. 2 (1965), 124). However, this process has the disadvantages that it is not widely applicable and that the desired products are only obtained in relatively low yields owing to interfering side reactions. Thus, to a considerable extent, the aryl amine attacks the carbonyl group which is adjacent to the trifluoromethyl group. The resulting enamine readily reacts with a further arylamine molecule, giving bis-adducts. This reaction can be illustrated by the following equation: ##STR3## Furthermore, it is known that N-aryl-trifluoroacetoacet-amides can be prepared by eliminating one molecule of aryl amine from the bis-adducts of the abovementioned structure (cf. DE-A 42 18 159). It is a disadvantage of this process that it requires one step more than the method described above. Moreover, even here the yields are unsatisfactory for realizing the reaction on an industrial scale.
DETAILED DESCRIPTION OF THE INVENTION
It has now been found that trifluoroacetoacid-anilides of the formula ##STR4## in which R.sup.1 represents halogen or a radical of the formula ##STR5## in which R.sup.2 represents hydrogen or optionally substituted alkyl and cycloalkyl or represents optionally substituted aryl, ##STR6## is reacted with anilines of the formula ##STR7## in which R.sup.1 is as defined above, presence of a diluent, at temperatures between -20.degree. C. and +40.degree. C.
It is very surprising that trifluoroacetoacet-anilides of the formula (I) can be prepared by the process according to the invention in a smooth reaction with high yields. Such a reaction was unforeseeable, in particular because the trifluoroacetoacetyl chloride required as starting material is, even at low temperatures, only stable for a short period of time (cf. Chem. Abstr. 1964, 2788 f and GB-A 931 689). It is also surprising that those anilines of the formula (III) in which R.sup.1 represents a radical of the formula --NH--SO.sub.2 --R.sup.3 do not show any reaction worth mentioning of the trifluoroacetoacetyl chloride with the sulphonylamino group.
The process according to the invention has a number of advantages. Thus, the required starting materials are accessible in a simple manner and even in larger amounts. Furthermore, there are not any problems associated with the practice of the reaction and the isolation of the desired substances. It is particularly favourable that the trifluoroacetoacid-anilides are obtained in high yield and high purity. Furthermore, the process is widely applicable.
Using trifluoroacetoacetyl chloride and 4-cyano-2-fluoro-5-methylsulphonylamino-aniline as starting materials, the course of the process according to the invention can be illustrated by the following equation: ##STR8##
The trifluoroacetoacetyl chloride of the formula (II) required as starting material for carrying out the process according to the invention is known (cf. GB-A 931 689).
The formula (III) provides a general definition of the anilines furthermore required as starting materials for carrying out the process according to the invention. Preference is given to using compounds of the formula (III) in which ##STR9## in which R.sup.2 represents hydrogen or represents alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl group or alkylaminocarbonyl having 1 to 4 carbon atoms in the alkyl moiety and substituted by cyano, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylaminoca
REFERENCES:
patent: 5127935 (1992-07-01), Satow et al.
patent: 5593945 (1997-01-01), Andree et al.
patent: 5681794 (1997-10-01), Andree et al.
J. Heterocyc. Chem., Jun. 2, 1965, pp. 120-125, Dey et al, Synthesis and Properties of Fluorine-Containing Heterocyclic Compounds. II. Trifluoromethyl Benzo[h]quinolines, Benzo[h]-1,6-napthyridines, 1,7- and 1,10-Phenanthrolines (1).
Kampfen Ulrich
Lantzsch Reinhard
Steinbeck Karl
Bayer Aktiengesellschaft
Gil Joseph C.
McKane Joseph K.
Murray Joseph
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