Реакция #94862

Уравнение реакции

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

Растворители

ether

methanol

methanol

Условия реакции

Обработка

1. 1
   ДругоеThe residue obtained by evaporation of the solvent
2. 2
   Другоеwas partitioned between ethyl acetate (100 ml.) and water (20 ml.) The organic layer
3. 3
   Другоеwas isolated
4. 4
   Промывкаwashed with water (20 ml)
5. 5
   Сушкаdried (magnesium sulphate)
6. 6
   Другоеevaporated
7. 7
   ДругоеThe appropriate zone of the chromatogram was isolated
8. 8
   Экстракцияextracted with hot ethanol/chloroform 50:50 v/v (200 ml.)
9. 9
   Другоеthe residue obtained on evaporation of the solvents
10. 10
    Другоеfollowed by a further amount of ether until precipitation
11. 11
    ПромывкаThe white powder precipitate (0.2 g.) was washed with ether

Методика

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.).

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