IL42610A - The preparation of n-(diethylaminoethyl)2-methoxy-4-amino-5-chlorobenzamide - Google Patents

Description

The preparation of ET 40735 present invention concerns a novel method of preparing its of addition with pharmaceutically acceptable mineral or organic and the quaternary ammonium salts produced by reacting the benzamide vith an alkylating Israel Patent Specification 17500 discloses a method for the preparation of substituted in which the amidification is effected by reacting a benzoic acid chloride with an and British patent specification another herein a benzoic acid ester is reacted with an amine and the chlorination carried out with Another method in which the amidification is effected by reacting a benzoic acid ester with an amine is described in The benzamide of the present invention is produced by treating benzoic acid by in the presence of ethyl chloroformiate to produce benzamide and chlorinating said compound by an alkaline chlorate to produce The reaction dia ram is as STAGE 110 g of 2 litres of dioxan and 92 ml of triethylamine are introduced into a 4 litre balloon flask provided a mechanical a a cooler and a dropping The mixture is agitated for 10 minutes and then g of ethyl is poured in at ambient The mixture is agitated for a further minutes and 90 g mole of N diethylaminoethylenediamine is vith the temperature being maintained at ambient The mixture is then agitated for 3 followed by and the solvent is evaporated under 200 ml of water is added to the and ml of sodium and the solution is extracted vith 150 ml of methylene The organic solution is dried on magnesium filtered and evaporated to dryness under g of 27 C is produced in the form of a thick STAGE 16 g of round and 60 ml of acetic are introduced into a 500 flask provided vith an a a thermometer and a dropping and heated to 45 of acetic anhydride is then poured The mixture is agitated for 15 minutes at 45 followed by and 18 ml of hydrochloric acid is then the temperature being at ambient A solution of of sodium chlorate in 15 of water is then added with the temperature being maintained at from 20 to 25 the solution is then agitated for 40 followed by the addition of 100 ml of and sodium hydroxide in an amount sufficient to and Ileating under reflux is then effected for 2 followed by vatcr and drying in a drying oven at g of is 9 insufficientOCRQuality

Claims (4)

1. A method of preparing N- 2-(N' , '-diethylamino) ethyl/ 2-methoxy-4-araino-5-chlorobenzamide, which has the formula: and its acid-addition salts with pharmaceutically acceptable mineral or organic acids and quaternary ammonium salts, that comprises reacting Ν,Ν-diethylethylenediamine with 2- ethoxy-4~aminobenzoic acid in the presence of ethyl chloroformate to produce N-diethylaminoethyl-2-methoxy-4- in the presence of HCl aminobenzamide and reacting the latter compound/with an alkali metal chlorate to produce N- 2-(N' ,N'-diethylamino)ethyl7- 2-methoxy-4-amino-5-chlorobenzamide, and optionally reacting the latter with an acid or a quaternizing agent to form a salt.

2. A method according to claim 1 in which the alkali metal chlorate is sodium chlorate.

3. A method according to claim 1 substantially as hereinbefore described in the foregoing Example *

4. N- 2- (N ' , N · -diethylamino ) ethyl7-2-methoxy-4-amino-5-chlorobenzamide when prepared by a method as claimed in any one of the preceding claims. •