Ammonia → HCID 178512619, compound

Participants

Reaction Steps

To a solution of 2-guanidino-4-(3-aminocyclohexyl)thiazole (0.3 g.) in ethanol (30 ml.) was added 2-methyl-1-nitroisothiourea (0.2 g.) and the mixture allowed to stand overnight at room temperature. The residue, obtained on evaporation of the reaction mixture, was subjected to preparative thin layer chromatography on silica gel GF plates (Uniplate, Analtech Inc. Delaware, USA) using chloroform:methanol:ammonia (s.g. 0.88) 80:20:0.5 v/v/v for development. Elution of the appropriate region of the chromatogram with hot ethanol and evaporation of the solvent gave a glass-like material. This was dissolved in a small volume of ethanol and the solution treated with a solution of maleic acid in acetone. The resulting solution was diluted with ether to give 2-guanidino-4-[3-(2-nitroguanidino)cyclohexyl] thiazole maleate hemihydrate (0.12 g.) which was obtained as an amorphous solid. The n.m.r. spectrum in d6 dimethylsulphoxide included resonances at 1.2 (brm), 1.8 (brm), 2.7 (m) 3.5(m) 6.11(s-maleic acid olefinic protons), 6.9(s), 8.05 (m) and 8.14 (brs).

Provenance & Evidence