DE2125449A1 - N phenetyl 5 chlorine 2 methoxybenzamide - Google Patents

Description

DR.-ING. DIPL-ING. G. RIEBLING My sign

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J.

899 Lindau (Bodensee) Your message from My message from Rennerle 10 PO Box 365

May 19, 1971

Frank W. Horner Limited

5485 Ferrier Street, Town of Mount Royal, Quebec / Canada

N-Ph enetyl-5-Ch Io r-2-iyieth oxy benzamide

This invention relates to a method of manufacture of N-phenethyl-5-chloro-2-hilethoxybenzamide.

In a pending application there is a method for Production of p- (2- "f 5-chloro-2-lethoxybenzamide J ethyl) Benzenesulfonamide described which from the treatment

- 2 109851/1819

of 5-chlorosalicylic acid or its ester IIIethyl-5-chlorosalicylate by fflethylation and aminolysis consists in order l \ l-Phenetyl-5-chloro-2-IYiethoxybenzamid to form, whereupon Sulphochlorination and aminolysis follows.

It has now surprisingly been found that the murder Ester fflethyl-5-chlorosalicylate can be treated, around l-phenethyl-5-chloro-2-fflethoxybenzainide in crude yields to form, uienn the steps of lYlethylating and the Reverse aminolysis. Thus, the aminolysis produces of the ester I-methyl-5-chlorosalicylate is a new dimethylated one Amide N-phenetyl-B-chlorosalicylamide, which is used in Hflethylation gives the above-mentioned methylated amide N-phenetyl-5-chloro-2- (¥ lethoxybenzamide.

The reactions described above are used in the following Scheme illustrates:

CO ₂ CH ₃

JiCH ₂ CH ₂ NH

f Op ₃

^ 0NHCH ₂ CH

iyiethyl-5-chlorosalicylate

N-phenetyl-5- N-phenetyl-5-

ChIo rs alicyl amide Chlor-2-IKIethoxybenzamid

10 9 8 51 / 1819-

The aminolysis of the ester IKlethyl-5-Chlorsalizylat executed iuird by treatment with phenetylamine, preferably between about 60-82 ⁰ C (14o to 18o ⁰ F), mährend the lYlethylierung is carried out in a conventional Uleise by treatment with dimethyl sulfate in an aqueous by heating to Solution of sodium hydroxide (or, alternatively, in an anhydrous solution using potassium carbonate).

The invention will now be illustrated by the following examples;

illustrates:

example 1

N-phenetyl-5-chlorosalicylamide

A mixture of 100 g of methyl 5-chlorosalicylate and 120 g of phenethylamine was heated to 155 ° for 5 hours.

The excess amine uiurde and distilled in vacuo the remainder was recrystallized from ether to obtain 100 g with a melting point of 117 to 119 °.

The ether was evaporated from the anger fluid and f

the remainder was distilled to obtain a further 17.5 g of the amide (boiling point 195 at 0.1 mm). The overall yield was 117.5 g (79 %) .

109851/1819

Example 2

N-phenetyl-5-chloro-2-bethoxybenzamide To a solution of 22 g of N-phenetyl-5-chlorosalicylamide in 168 ml of acetone, 53 ml of 2-N-sodium hydroxide and 12 g of dimethyl sulfate were added. After stirring the mixture for 10 minutes, another 27 ml of sodium hydroxide and 12 g of dimethyl sulfate were added. The mixture was allowed to reflux for 45 minutes and the acetone was evaporated. After extraction of the residue with ether and evaporation of the ether, the residue was distilled. After crystallization of the product from a little ether, 16 g with a melting point of 61 to 64 ° (75 %) were obtained.

Claims

10 9 8 51/1819

Claims (2)

Claims. 1. Process for the preparation of N — Phenetyl — 5— Chloro-2-iyiethoxybenzamide by treating hilethyl-5-chlorosalicylate with phenetylamine to make N-phenetyl-5-chlorosalicylamide and then lYlethylating the latter. 2. compound, characterized in that it is selected from the group _? which contains l \ l-phenetyl-5-chloro-2-iyiethoxybenzaniid and N-phenetyl-5-chlorosalicylamide. 10 9 8 5 1/18 19