Triethylamine → HCID 178509528, Verbindung

HRID 574731

Reaktionsgleichung

Reaktionsgleichung von HRID 574731
Cl.[NH:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH2:12])=[CH:10][C:5]=2[N:4]=[CH:3]1.[N:13]([C:16]1[S:20][C:19]2[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=2[C:17]=1[C:25]([O:27]CC)=O)=[C:14]=[S:15].C([N:32](CC)CC)C>CN(C=O)C.ClCCl>[NH:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH2:12])=[CH:10][C:5]=2[N:4]=[CH:3]1.[S:15]=[C:14]1[NH:13][C:16]2[S:20][C:19]3[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=3[C:17]=2[C:25](=[O:27])[NH:32]1

Komponenten

6

Edukt 3

HCID 8471Triethylamine2×HCID 2779675Ethyl 2-isothiocyanato-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylateHCID 178479175(1H-Benzo[d]imidazol-5-yl)methanamine hydrochloride

Produkt 1

HCID 178509528HCID 178509528, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(1H-benzo[d]imidazol-5-yl)methanamine (14) (0.08 g, 0.46 mmol) and ethyl 4,5,6,7-tetrahydro-2-isothiocyanatobenzo[b]thiophene-3-carboxylate (0.12 g, 0.46 mmol) were dissolved in 1mL DMF and dichloromethane. Triethylamine (128 μL, 0.92 mmol) was added to the mixture. The mixture was stirred for 12 hours at ambient temperature. The solvent was removed and the resulted residue was dissolved in ethanol. Triethylamine (128 μL, 0.92 mmol) was added and the mixture was heated under reflux for 12 hours. The solvent was removed and the resulted residue was dissolved in ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over sodium sulfate, filtrated and the solvent was removed. The product was purified by means of flash-chromatographie using silica gel and a CHCl3/MeOH-gradient.

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionthe resulted residue was dissolved in ethanol
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 12 hours
  5. customThe solvent was removed
  6. dissolutionthe resulted residue was dissolved in ethyl acetate
  7. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltrated
  10. customthe solvent was removed
  11. customThe product was purified by means of flash-chromatographie

Quellen und Nachweise

ORD-Eintrag
ord-09452a8fcc0b42bc833f7e806cad2b12
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034907B2

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