Reaktion #83032

Reaktionsgleichung

methyl isothiocyanate

5-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

→

5-(2-methylaminothiocarbonylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 3 hours
2. 2
   workup.DISTILLATIONThe reaction mixture was subjected to vacuum distillation
3. 3
   Sonstigeto remove ethanol
4. 4
   workup.ADDITIONThe residue was mixed with a saturated aqueous sodium hydrogencarbonate solution
5. 5
   Extraktionfollowed by extraction with ethyl acetate
6. 6
   TrocknenThe organic layer was dried over magnesium sulfate
7. 7
   workup.DISTILLATIONsubjected to vacuum distillation
8. 8
   Sonstigeto remove the solvent
9. 9
   SonstigeThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol =50/1)

Vorschrift

0.13 ml of methyl isothiocyanate was added to 20 ml of a suspension of 0.5 g of 5-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine in ethanol. The mixture was refluxed for 3 hours. The reaction mixture was subjected to vacuum distillation to remove ethanol. The residue was mixed with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and then subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol =50/1) to obtain 0.46 g of 5-(2-methylaminothiocarbonylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Quelle