Réaction #83032

Équation de réaction

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

Solvants

ethanol

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source