Phosphorus oxychloride → 2-chloro-4-methoxy-1H-Benzimidazole

HRID 555872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555872
[CH3:1][O:2][C:3]1[C:11]2[NH:10][C:9](=O)[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:9]1[NH:10][C:11]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 129266284-methoxy-1H-benzo[d]imidazol-2(3H)-one

Produkt 1

HCID 1784889662-chloro-4-methoxy-1H-Benzimidazole

Versuchsvorschrift

To a round bottomed flask was added 4-methoxy-1H-benzo[d]imidazol-2(3H)-one (1.8163 g, 11.06 mmol). POCl3 (1.031 mL, 11.06 mmol) was added and the reaction was brought to reflux. Upon completion, POCL3 was evaporated off. The residue was taken up in DCM. The reaction mixture was diluted with water and saturated sodium bicarbonate and extracted with DCM. The organic extract was washed with sat. sodium bicarbonate solution, water, brine, dried with, magnesium sulfate, filtered, and concentrated to provide 2-Chloro-7-methoxy-1H-benzo[d]imidazole. [M+H]=182.9.

Aufarbeitung

  1. temperatureto reflux
  2. customUpon completion, POCL3 was evaporated off
  3. additionThe reaction mixture was diluted with water and saturated sodium bicarbonate
  4. extractionextracted with DCM
  5. extractionThe organic extract
  6. washwas washed with sat. sodium bicarbonate solution, water, brine
  7. dry with materialdried with, magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-96bc57a28b6a45ba83148f29132557f6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053438B2

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