KR800000486B1 - Process for the preparation of n-(diethylamino-ethyl)2-methoxy-4-amino 5-chlorobenzamide - Google Patents

Abstract

N-(diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide(I) was prepd. by the teatment of benzoyl chloride(II) with N, N-diethylaminoethlamine, which II was obtained from 2-methoxy-4-acetamido-5-chlorobenzoic acid and triphenyltrichloromethylphosphonium chloride. Thus, 180 ml dioxane, 60ml carbon tetrachloride and 15.8 g triphenylphosphine were heated at 70≰C for 1 hr cooled to 5010≰C, and added 7.3 g 2-methoxy-4-acetamido-5-chlorobenzoic acid. Obtained bezoic acid was treated with 21 g N,N-diethylaminoethylamine at 70≰C for 1 hr to give I.

Description

Method for preparing N- (diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide

The present invention relates to a method for producing N- (diethylanimoethyl) 2-methoxy 4-amino 5-chlorobenzamide of the following general formula (3).

In the preparation method of the present invention, triphenylphosphine (C ₆ H ₅ ) ₃ P is used as a starting material, and reacted with carbon tetrachloride to triphenyl trichloromethylphosphonium chloride (C ₆ H ₅ ) ₃ P + CCl ₃ (Cl-) was obtained, followed by reaction of this compound with 2-methoxy 4-acetamino 5-chloro benzoic acid, and then triaryl acyloxyphosphonium chloride of formula (1) was converted to triphenylphosphine oxide PO ( With the formation of C ₆ H ₅ ) _{3 it} is converted to the corresponding acid chloride of the following general formula (2), and this benzoyl chloride (2) is reacted with N, N-diethylaminoethylamine to give the following general formula (3) It is composed of preparing the desired benzamide.

When the present invention is represented by the reaction scheme as follows.

Benzamide of the present invention has the pharmacological properties described in French Patent No. 1,525M, filed July 25, 1961.

2-methoxy 4-acetamido 5-chlorobenzoic acid used as a starting material is described in British Patent No. 1,136,333, issued July 23, 1969, and US Patent No. 3,342,826, issued September 19, 1967. It is.

Hereinafter, the present invention will be described in detail with reference to Examples.

EXAMPLE

N- (diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide

180 ml of dioxane, 60 ml of carbon tetrachloride and 15.8 g (0.06 mol) of triphenylphosphine were placed in a 500 ml flask equipped with a stirrer, a cooler and a thermometer, and the contents of the flask were heated at 70 ° C. for 1 hour. After cooling to 5-10 ° C., 7.3 g (0.03 mol) of 2-methoxy 4-acetamido 5-chlorobenzoic acid was added thereto. The liquid was stirred at this temperature for 1/2 hour before almost all of the acid became a solution. 21 g (0.18 mol) of N, N-diethyl aminoethylamine were added, and the mixture was heated at 70 ° C. for 1 hour and then cooled. The solvent was evaporated in vacuo, the residue was poured into water, acidified with concentrated hydrochloric acid and the precipitate was filtered off.

The filtrate was made alkaline using soda to pH 10, filtered and the crystals were reacted by boiling with 5N soda for 1/2 hour, the reaction mixture was cooled, filtered and dried in a drier at 50 ° C. The product was finally recrystallized in benzene to give 2.9 g of N- (diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide. Yield: 33%, Melting point: 143 ° C

Claims (1)

As described above in this text, the compound obtained by reacting triphenylphosphine (C ₆ H ₅ ) ₃ P with carbon tetrachloride is reacted with 2-methoxy 4-acetamino 5-chlorobenzoic acid and then the compound obtained as described above. Of N- (diethyl amino ethyl) 2-methoxy 4-amino 5-chloro benzamide of formula (3) consisting of treating N with N, N-diethylamino ethyl amine to give the desired benzamide Manufacturing method.