Preparation of N'-(4--2,5-dimethylphenyl)-N- ethyl-N-methylimidoformamide

Process for the preparation of N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide comprising at least one of the following steps (a) to (j):

• (a) reaction of nitrobenzene derivatives of the formula (III) with a thiadiazolyl alcohol of the formula (II) according to the following reaction scheme:
• (b) reaction of the nitrophenol derivative of the formula (V) with thiadiazolyl derivatives of the formula (IV) according to the following reaction scheme:
• (c) reaction of anilines of the formula (VII) with a thiadiazolyl alcohol of the formula (II) according to the following reaction scheme:
• (d) reaction of an aminophenol of the formula (XII) with thiadiazolyl derivatives of the formula (IV) according to the following reaction scheme:
• (e) reduction of the nitrophenoxy ether of the formula (VI) to give the aniline ether of the formula (VIII) according to the following reaction scheme:
• (f) reaction of the aniline ether of the formula (VIII) with
• (i) aminoacetals of the formula (XII) or
• (ii) an amide of the formula (XIV) or
• (iii) an amine of the formula (XV) in the presence of ortho esters of the formula (XVI)
• (iv) ortho esters of the formula (XVI) to give imidoformates of the formula (XVIII) and in a second step with methylethylamine (XV)
• according to the following reaction scheme:
• (g) reaction of an aminophenol of the formula (XII) with
• (i) aminoacetals of the formula (XIII) or
• (ii) an amide of the formula (XIV) or
• (iii) an amine of the formula (XV) in the presence of ortho esters of the formula (XVI)
• (iv) ortho esters of the formula (XVI) to give imidoformates of the formula (XIX) and in a second step with methylethylamine (XV)
• according to the following reaction scheme:
• (h) reaction of the aminophenols of the formula (VII) with
• (i) aminoacetals of the formula (XIII) or
• (ii) an amide of the formula (XIV) or
• (iii) an amine of the formula (XV) in the presence of ortho esters of the formula (XVI)
• (iv) ortho esters of the formula (XVI) to give imidoformates of the formula (XX) and in a second step with methylethylamine (XV)
• according to the following reaction scheme:
• (i) reaction of amidines of the formula (XI) with a thiadiazolyl alcohol of the formula (II) according to the following reaction scheme:
• (j) reaction of an amidine of the formula (X) with thiadiazolyl derivatives of the formula (IV) according to the following reaction scheme:
• where, in the above schemes,
• Z is a leaving group;
• and
• R8 to R10 independently of one another, are selected from the group consisting of hydrogen, C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl, C5-18-aryl, C7-19-arylalkyl or C7-19-alkylaryl groups and in each case R8 with R9, R8 with R10 or R9 with R10, together with the atoms to which they are bonded and optionally with further C, N, O or S atoms, can form a five-, six- or seven-membered ring;
• R11 and R12 independently of one another, are selected from the group consisting of hydrogen, C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl, C5-18-aryl or C7-19-arylalkyl groups and, together with the atoms to which they are bonded, can form a five-, six- or seven-membered ring.