DE1420969A1 - Process for the preparation of 4,5-dihalopyridazones - Google Patents

Description

Process for the production of 4,5 - D.ihalogenpyr # ldazonen- (6) The subject of the main patent ... ... (Application B 53 704 IVb / 12p) is a process for the production of halopyridazonen- (6) of the general formula in which R 1 is a substituted aliphatic or aromatic radical and X and Y are halogen atoms, by reacting mucohalogenic acids in an aqueous mineral acid solution at room temperature with - optionally substituted in the alkyl or aryl radical - alkyl or aryl hydrazines and treating the resulting product with concentrated sulfuric acid or by directly heating mucohalogenic acids together with alkyl or aryl hydrazines optionally substituted in the alkyl or aryl radical in aqueous mineral acid solution to about 70 to 100 ° C. As radicals through which the alkyl and aryl hydrazines in the alkyl or. Aryl radicals that can be substituted are sulfonic acid, sulfonic acid amide, alkyl, alcohol, xy, acylamino and / or nitro groups.

It has been found that in the preparation of 495-dihalopyridazones- (6) of the general formula in which R 1 is a substituted aliphatic or aromatic one The remainder and X and Y are halogen atoms, by reacting yon Mucohalogenic acids in mineral acidic # aqueous solution for space-- temperature with substituted in the alkyl or aryl radical6n alkyl or arylhydrazines and treatment of the resulting product, .. with concentrated sulfuric acid or by direct Heating of mucohalogenic acids together with im * alkyl - or. Arylreg-V-substituted alkyl or aryl hydrazines in mineral 0 acid-aqueous solution to about 70 to 100 0 also alkyl and arylhydrazines can be used by carboxyl, carbo- alkoxyl, 7, carbonamide, cyano, amino groups or through Alkyl or aryl, r-este bearing - amidocarbonyl, sulfonyl amino-i Carb onylamino, CarboAyl and sulfonyl groups substituted tu # ext 'are called alkyl or aryl radicals Groups can also be sub- gave In ubr-'x'.j # en the 'Naßnahm, An ej1, jee .1-Iguptpa cast parts ze 1) le #n degn an, and 2 percent alil a zin4 Example # 1 , wel, e. # q 3.-M '- # ". - 69 T become a f xual e: # e d # azotiert and -with 230 Te-il, # @, n TeJUZJ »ext #, Man j 5 # a, -. t -b to the Gemjech, 85 T911e rUh-rt-dge whole U Z ounce 20 -hours at room temperature and f ilt, rz »ert -dgz meet- Product. Ngot the door step mä. a-ez Unter Ruhren in 500 parts concentrated one. Kan is still turning, 12 for 15 3 hours and then pours the odor in bit water "- whereby. 4;, elbeo powder of melting point - 314 big 31-6'-C- in e '# ine- x -, yield- of 136 places is # 41-t ". Example 2 8.5 parts that you go through from - With -Alet # YIXitril is obtained leaves inane with stirring in 500 parts e %, x more influence -, - Ueser 141, schung f, ii, et- man # 170 Tall down. and- # exWarms the whole thing 1 $ tu-ad-e - aut - 90 received-t-man, 21 0- parts 1- (2- # cyanoethyl) -4,5-dichloropyridazon- (6) as-colorless ver-- bond from melting point 85 Example 3 20 parts of 3-aminophenylhydrazine dihydrochloride by diazotizing 3-aminoacet, anilide, reducing the diaz # o-- Connection to hydrazine and hydrolysis of acetaminophenyl hydrazines with 8 % hydrochloric acid are mixed with 17 parts of chloric acid in 200 parts of 8 % hydrochloric acid for one hour 90 0 C heated. By cooling down, 32 parts of 1- (3-amino- phenyl) -4,5-dichloropyrid'äton- (6) -hydräc'hlorid.-Same-Viar-- ' biz # dung 'is obtained in a yield of -15 parts, -weÜn-man the above mixture is stirred at 4.0 ° C. for 48 hours. The free 1 - (- 3 # -aminophenyl) -495-dichloronyridazon- (6) is obtained 0 .man in the form of pale yellow crystals with a melting point of 132 ° C by neutralizing the aqueous solution of the hydrochloride with sodium bicarbonate solution-, Dieselbe- Verbindu n g is also obtained, transit Re-duk '# ion of, IM "- (3- Nitrophenyl) -4, - # 5-'dichloropyridazoh # (6). or by Verseifexi d-es- 1- (3-Ac: etamino) "4,5" di ..- chldrpyrldazon "(6), J. Example 4 20 parts of i3, kminoäthylhy.drazine and 45 parts of mucochloric acid it is heated in 300 parts of 8 % hydrochloric acid to 90 ° C. for 2 hours. * By cooling, 32 parts of 1-βLAniinoethyl-4,5-dichloropyrfdazon- (6) hydrochloride are obtained in the form of a colorless crystalline product which- -melts at 264 to 2660C, -0 6 'L7 0 N 3 c12 HCl, (24495) Ber. C 29.46. H 3.30 0 6-? 54- N 17.16. 01 43.5 Found 2996 35.4 79.0. 1793 4320

Claims (1)

Patent claim Expansion of the process according to patent ... ... (patent application B 53 704 IVb / 12p) for the preparation of 4,5-dihalogenpyridazones- (6) of the general formula in which R is a substituted aliphatic or aromatic radical and X and Y are halogen atoms, by reacting nuaohalogenic acids in mineral acidic aqueous solution at room temperature with alkyl or aryihydrazines substituted in the alkyl or aryl radical, treatment of the reaction products with concentrated sulfuric acid or immediate heating of mucohaloenoic acids together with alkyl or aryl hydrazines substituted in the alkyl or aryl radical in aqueous mineral acid solution, characterized in that alkyl or "Ary1- h-vdrazine used by carboxyl, carboalkoxyl .. Carbonamide, cyano, amino groups or by - alkyl or Aryl radicals - amidocarbonyl, sulfonylamino, carbonyl amino, carbonyl and sulfonyl groups are substituted.