反応 #94862

反応方程式

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

溶媒

ether

methanol

methanol

反応条件

後処理

1. 1
   その他The residue obtained by evaporation of the solvent
2. 2
   その他was partitioned between ethyl acetate (100 ml.) and water (20 ml.) The organic layer
3. 3
   その他was isolated
4. 4
   洗浄washed with water (20 ml)
5. 5
   乾燥dried (magnesium sulphate)
6. 6
   その他evaporated
7. 7
   その他The appropriate zone of the chromatogram was isolated
8. 8
   抽出extracted with hot ethanol/chloroform 50:50 v/v (200 ml.)
9. 9
   その他the residue obtained on evaporation of the solvents
10. 10
    その他followed by a further amount of ether until precipitation
11. 11
    洗浄The white powder precipitate (0.2 g.) was washed with ether

実験手順

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.).

出典