Acetic Acid → 7-(Methylthio)-1H-benzo[d]imidazole

HRID 657521

Reaktionsgleichung

Reaktionsgleichung von HRID 657521
[CH3:1][S:2][C:3]1[C:4]([N+:10]([O-])=O)=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[C:13](O)(=O)C>C(OC)(OC)OC.[Zn]>[CH3:1][S:2][C:3]1[C:4]2[N:10]=[CH:13][NH:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 109761553-(Methylthio)-2-nitroaniline

Produkt 1

HCID 251423217-(Methylthio)-1H-benzo[d]imidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 9005Trimethyl orthoformateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6 g of 3-methylsulfanyl-2-nitrophenylamine were dissolved in 150 ml of glacial acetic acid and 60 ml of trimethyl orthoformate. Zinc powder (7 g) was added and the mixture was stirred for 2 h at 60° C. The solids were removed by filtration, the solvent was evaporated in vacuo and the residue was taken up in water and EA (200 ml each) and made basic with potassium carbonate. The precipitate was filtered off and the filtrate was extracted with EA, the combined organic phases were washed with brine, dried over sodium sulfate and the solvent removed in vacuo. The crude product was purified by flash chromatography (200 g silica gel; DCM/MOH, gradient from 100:0 to 90:10). 2 g of the title compound were obtained as an off-white solid.

Aufarbeitung

  1. customThe solids were removed by filtration
  2. customthe solvent was evaporated in vacuo
  3. filtrationThe precipitate was filtered off
  4. extractionthe filtrate was extracted with EA
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed in vacuo
  8. customThe crude product was purified by flash chromatography (200 g silica gel; DCM/MOH, gradient from 100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-520035295497457c85d084cf43b836ce
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076324B2

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