Reaktion #94862

Reaktionsgleichung

maleic acid

2-guanidino-4-{3-[3-cyano-2-(2-aminoethyl)guanidino]cyclohexyl}thiazole

o-chlorobenzoyl chloride

→

2-guanidino-4-{ 3-[3-cyano-2-(2-(2-chlorobenzoylamino)ethyl)guanidino]cyclohexyl}thiazole hydrogen maleate

Lösungsmittel

ether

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe residue obtained by evaporation of the solvent
2. 2
   Sonstigewas partitioned between ethyl acetate (100 ml.) and water (20 ml.) The organic layer
3. 3
   Sonstigewas isolated
4. 4
   Waschenwashed with water (20 ml)
5. 5
   Trocknendried (magnesium sulphate)
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe appropriate zone of the chromatogram was isolated
8. 8
   Extraktionextracted with hot ethanol/chloroform 50:50 v/v (200 ml.)
9. 9
   Sonstigethe residue obtained on evaporation of the solvents
10. 10
    Sonstigefollowed by a further amount of ether until precipitation
11. 11
    WaschenThe white powder precipitate (0.2 g.) was washed with ether

Vorschrift

To a solution of 2-guanidino-4-{3-[3-cyano-2-(2-aminoethyl)guanidino]cyclohexyl}thiazole (0.5 g.) in methanol (30 ml.) was added o-chlorobenzoyl chloride (0.4 g.) and the mixture allowed to stand at room temperature for 16 hours. The residue obtained by evaporation of the solvent was partitioned between ethyl acetate (100 ml.) and water (20 ml.) The organic layer was isolated, washed with water (20 ml), dried (magnesium sulphate) and evaporated. The residue was subjected to preparative thin layer chromatography on Merck 60 F-254 plates using chloroform/methanol/aqueous ammonia (s.g. 0.88) 80:20:0.1 v/v/v for development. The appropriate zone of the chromatogram was isolated and extracted with hot ethanol/chloroform 50:50 v/v (200 ml.) and the residue obtained on evaporation of the solvents was dissolved in methanol. To this solution was added an excess of maleic acid in ether followed by a further amount of ether until precipitation began. The white powder precipitate (0.2 g.) was washed with ether to give 2-guanidino-4-{ 3-[3-cyano-2-(2-(2-chlorobenzoylamino)ethyl)guanidino]cyclohexyl}thiazole hydrogen maleate, m.p. 158°-165° (decomp.).

Quelle