Réaction #63090

Équation de réaction

2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)thiazole

2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[4-isothiocyanatobutyl]thiazole

maleic acid

→

1,3-di[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)butylamino]thiourea

maleic acid

Solvants

methanol

acetone

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was then evaporated to dryness
2. 2
   Autrepurified by preparative thin layer chromatography
3. 3
   ExtractionThe appropriate band was extracted with chloroform/ethanol 1:1 v/v (200 ml.)
4. 4
   Autrethe resulting solution evaporated
5. 5
   Autreto give a brown gum

Mode opératoire

A mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)thiazole (0.12 g.) and 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[4-isothiocyanatobutyl]thiazole (0.12 g.) in methanol (3 ml.) was allowed to stand at room temperature overnight. The mixture was then evaporated to dryness and purified by preparative thin layer chromatography using methanol/chloroform/ammonia 85:15:1 v/v/v as developing solvent. The appropriate band was extracted with chloroform/ethanol 1:1 v/v (200 ml.) and the resulting solution evaporated to give a brown gum. This was treated in acetone with excess maleic acid to give 1,3-di[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)butylamino]thiourea containing 2.25 equivalents of maleic acid. The n.m.r. spectrum in d6 dimethylsulphoxide containing tetramethylsilane as internal standard (δ=0) included the following resonances (δ): 1.5 (multiplet, 8H); 3.3 (multiplet, 4H); 4.1 (quartet, 4H); 6.5 (singlet, 2H).

Source