Réaction #63084

Équation de réaction

2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-phthalimidobutyl)-5-methylthiazole hydrochloride

sodium hydroxide

hydrochloric acid

→

2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)-5-methylthiazole dihydrochloride

Rendement 128.6%

Solvants

water

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting yellow solution was heated on a steam bath for 10 minutes
2. 2
   TempératureAfter cooling to ambient temperature the mixture
3. 3
   Extractionwas extracted three times with equal volumes of ethyl acetate
4. 4
   AutreThe aqueous layer was evaporated to dryness
5. 5
   Autreazeotroped twice with toluene
6. 6
   workup.DISSOLUTIONthe residue dissolved in methanol (10 ml.)
7. 7
   Filtrationthe solution filtered
8. 8
   AutreThe filtrate was evaporated to dryness

Mode opératoire

To a mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-phthalimidobutyl)-5-methylthiazole hydrochloride (0.60 g.) in water (2 ml.) and ethanol (2 ml.) was added sodium hydroxide pellets (0.2 g.). The resulting yellow solution was heated on a steam bath for 10 minutes and then allowed to cool to ambient temperature. The reaction mixture was adjusted to pH3 by addition of 2N hydrochloric acid and then reheated on a steam bath for 1 hour. After cooling to ambient temperature the mixture was extracted three times with equal volumes of ethyl acetate. The aqueous layer was evaporated to dryness, azeotroped twice with toluene, the residue dissolved in methanol (10 ml.) and the solution filtered. The filtrate was evaporated to dryness to give 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)-5-methylthiazole dihydrochloride (0.31 g.) as an oil which was used without further purification.

Source