DE505321C - Process for the production of naphthostyrils monochlorinated in the core - Google Patents

Description

Process for the preparation of naphthostyriles monochlorinated in the core It has been found that the in patent [; i 269 described, in the core monochlorinated napthostyrile can advantageously be obtained in one operation if one treats N aplithostvril or its derivatives with chlorine or chlorine-releasing agents, such as sulfur chloride or chlorate and hydrochloric acid, in sufficient quantities to form a monochlorine derivative.

The uniform formation of a monochloro derivative in this procedure is surprising, since Eckstrand was only able to obtain a dichloronaphthostyril when chlorine acted directly on naphthostyril (cf. J. pr. Ch. [21 38, pp. I; 8).

EXAMPLE I 109 parts of naphthostyril are dissolved in 220 parts of concentrated sulfuric acid, 3 parts of iodine are added and chlorine is now slowly passed in at 15 to 20 ° until a weight increase corresponding to the uptake of 1 atom of chlorine and until a sample has a melting point of about 266 ° decomposed. The mass is then poured onto ice, the precipitated chloronaphthostyril is filtered off and, if necessary, recrystallized from glacial acetic acid. This gives yellow to greenish yellow needles which melt at 266 °. The connection turns out to be identical to the chloronaphthostvril described by Eckstrand in a complicated way (J. pr. Ch. [2J 38, pp. 172 and 181). Example 2 169 parts of naphthostyril are in; Ooo parts of crude hydrochloric acid dissolved while hot, then the solution was cooled, whereby the naphthostate precipitated as the hydrochloric acid salt. For this purpose, an aqueous solution of 1 part sodium dichlorate is allowed to run in with stirring over the course of one hour, the temperature being expediently kept at 15 to 20 °. The mixture is stirred for some time, the precipitate is filtered off, washed out and dried. The chloronaphthostyril thus obtained in almost theoretical yield is identical to the compound obtained according to Example i. Example 3 To a solution of 17 parts of naphtliostyril in 2.0 parts of tetrachloroethane, 15 parts of sulfuryl chloride are slowly run in at 50 to 60 °. When the temperature rises, the chloronaphthostyril formed separates out in the form of yellow needles. It is held at 50 to 60 ° for some time, and after cooling, the reaction product is filtered off and dried. This gives a product which, without further purification, has a melting point of 265 °. Instead of tetrachloroethane, other suitable solvents or suspending agents, such as. B. glacial acetic acid, nitrobenzene or trichlorobenzene, use; Find. Example: To a solution of ro parts 5-ÄthOxynaphthostyril, which according to the method according to patent Sod. 342 can be obtained, in zoo parts glacial acetic acid is added a small amount of death and then allowed to run in at 50 to 60 ° S parts sulfuryl chloride. Even in the warmth, the chlorine-5-ethoxynaphthostyril separates in pale yellow, coarse needles. After obtaining, it is filtered with glacial acetic acid and then washed with water and dried. For cleaning, the product can be dissolved in warm glacial acetic acid and precipitated with water. It melts at around 25o °.

Claims (1)

PATENT CLAIM: Modification of patent 4 .; 1 269 protected process for producing fully monochlorinated in the core Naphthostyrilen, consisting in N treating aplitliostyril or derivatives thereof with chlorine or chlorine-releasing agents in an amount sufficient to form a mono-chloro derivative amount here.