Reacción #63090

Ecuación de reacción

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

Disolventes

methanol

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was then evaporated to dryness
2. 2
   Otropurified by preparative thin layer chromatography
3. 3
   ExtracciónThe appropriate band was extracted with chloroform/ethanol 1:1 v/v (200 ml.)
4. 4
   Otrothe resulting solution evaporated
5. 5
   Otroto give a brown gum

Procedimiento

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).

Fuente