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

HRID 54754

Reaktionsgleichung

Reaktionsgleichung von HRID 54754
[CH3:1][N:2]=[C:3]=[S:4].[NH2:5][CH2:6][CH2:7][O:8][CH:9]1[C:15]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:24][C:23]=2[O:38][CH3:39])[CH2:12][CH2:11][CH2:10]1>C(O)C>[CH3:1][NH:2][C:3]([NH:5][CH2:6][CH2:7][O:8][CH:9]1[C:15]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:24][C:23]=2[O:38][CH3:39])[CH2:12][CH2:11][CH2:10]1)=[S:4]

Komponenten

4

Edukt 2

HCID 11167Methyl isothiocyanateHCID 189172105-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Produkt 1

HCID 220716315-(2-methylaminothiocarbonylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 hours
  2. distillationThe reaction mixture was subjected to vacuum distillation
  3. customto remove ethanol
  4. additionThe residue was mixed with a saturated aqueous sodium hydrogencarbonate solution
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationsubjected to vacuum distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol =50/1)

Quellen und Nachweise

ORD-Eintrag
ord-b9068a8af0c245a297d2885f8bb587b9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622947

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