Production method for producing N-benzyl-2-(2-nitro-1H-imidazol-1-yl) acetamide

Abstract

The invention relates to the synthesis of a therapeutic agent which is effective against American trypanosomiasis (Chagas disease) caused by the protozoa Tripanosoma cruzi and transmitted by blood-sucking insects of the genera Triatoma or Rhodnius. This synthesis method is carried out in one step, in a solid state. It is a clean, simple, economical, rapid, easily implemented method, does not involve acid or base catalysts in the synthesis process, and is also environmentally friendly. It is a synthesis method for producing N-benzyl-2-(2-nitro-1-H-imidazol-1-yl)acetamide from the N-benzyl-2-hydroxyacetamide and 2-nitro-1H-imidazol reaction mixture, using microwave irradiation as an activation source in order to produce the N-benzyl-2-(2-nitro-1H-imidazol-1-yl)acetamide.

Claims

1. A process for preparation of N-benzyl-2(2-nitro-1H-imidazol-1-yl)acetamide of formula (I): ##STR00001## comprising reacting N-benzyl-2-hydroxyacetamide (II) and 2-nitro-1H-imidazol (III) ##STR00002## using microwave irradiation.

2. The process according to claim 1, without an excess of any of the reactants.

3. The process according to claim 1, where the reaction is made in solid phase, in absence of a solvent.

4. The process according to claim 1, where the reaction is carried out in absence of a catalyst.

5. The process according to claim 1, wherein the microwave irradiation is at 100 watts.

Description

DESCRIPTION OF THE INVENTION

(1) The present invention is related to the synthesis of an imidazolic derivative with tripanocide activity. The synthesis procedure takes place in a dry medium; it is a simple, economical, and environmently friendly. The synthesis consists in the PRODUCTION METHOD FOR PRODUCING N-BENZYL-2-(2-NITRO-1H-IMIDAZOL-1-YL)ACETAMIDE. N-benzyl-2-(2-nitro-1H-imidazol-1-yl)acetamide is prepared using as initial materials N-benzyl-2-hydroxyacetamide and 2-nitroimidazole, adding each one of the initial materials in an equimolar relation. The procedure is clean, it happens by mixing both initial materials and activating the mixture by microwaves irradiation to form the N-benzyl-2-(2 nitro-1H-imidazole-1-yl)acetamide. The microwave irradiation can be at 100 watts. The synthesis is rapid and easy to execute. The reaction mixture is purified using a chromatography column, using as a stationary base alumina and as a mobile phase ethyl acetate. The method does not require acid catalysts or bases in the synthesis process.

(2) The procedure in this invention can be used to obtain other imidazolic derivatives such as N-benzyl-2-(1H-imidazol-1-yl) acetamide using as initial materials 1H-imidazol and N-benzyl-2-hydroxyacetamide or 1H-imidazol and N-benzyl-2-chlorinacetamide.

EXECUTION EXAMPLE

(3) In the practice this reaction happens as follow: i. Mix the N-benzyl-2-hydroxyacetamide with the 2-nitromidazole in equimolar relation. Mix the initial materials in solid state, in absence of an organic or inorganic solvent, put them in a transparent receptable in a microwave oven, in a bath of silica and irradiate it with microwaves (700 W), level 4 to 7 in the oven, for approximately 10 minutes. The reaction mixture is purified through the chromography column, using alumina as a stationary phase and as a mobile phase ethyl acetate. TLC analysis is realized to the result product by infrared spectroscopy and spectrometry of mass.
IR=1156 and 1145 cm.sup.−1 (N—C, amina terciaria), 1539.3 and 1367 cms.sup.−1 (C—N, nitro group), 1660.3 cm.sup.−1 (CO—NH amide), 3275.3 cm.sup.−1 (NH-amide)
MS=260M.sup.+