Sodium Hydroxide → Ethyl 4,5-dihydro-8-methylthio-2-phenylthieno(3,4-e]benzimidazole-6-carboxylate

HRID 1108343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108343
[OH-].[Na+].Cl.[C:4]([NH2:12])(=[NH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH:14]1[CH2:29][CH2:28][C:17]2=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:19][C:20]([S:21][CH3:22])=[C:16]2[C:15]1=O>O.C(Cl)(Cl)Cl>[CH3:22][S:21][C:20]1[S:19][C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]2[CH2:28][CH2:29][C:14]3[N:11]=[C:4]([C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[NH:12][C:15]=3[C:16]=12

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 80289Benzamidine, hydrochlorideHCID 15885619Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

Produkt 1

HCID 178470566Ethyl 4,5-dihydro-8-methylthio-2-phenylthieno(3,4-e]benzimidazole-6-carboxylateAusbeute 13,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of sodium hydroxide (1.65 g) in water (3 ml) was added to a solution of benzamidine hydrochloride (5.38 g) in water (2 ml) at room temperature; a solution of ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.00 g) in chloroform (30 ml) was further added. The reaction mixture was refluxed under heating for 3 days, after which it was poured over water and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2, v/v) to yield ethyl 4,5-dihydro-8-methylthio-2-phenylthieno[3,4-e]benzimidazole-6-carboxylate (0.28 g, 13.2%), which was then recrystallized from ethyl acetate-ethanol. Brown prisms. Melting point 218-219° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed
  2. temperatureunder heating for 3 days
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationafter which the solvent was distilled off
  7. washeluted with ethyl acetate-hexane (1:2

Quellen und Nachweise

ORD-Eintrag
ord-34579df7752549729c93e6c5309a120c
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066658

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