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Phosphorus oxychloride → Methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

HRID 1698591
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1698591
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=O)[NH:14][C:10]=2[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][C:13]1[N:12]([CH3:16])[C:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]=2[N:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 67271829methyl 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

Produkt 1

HCID 67273217Methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (1.30 g, 4.70 mmol) and phosphoryl chloride (10 ml) was heated at 100° C. for 3 h. The mixture was diluted with toluene and concentrated in vacuo to remove excess reagent. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on column silica gel with a 10% ethyl acetate/n-hexane to give 1.18 g (4.00 mmol, 85%) of the title compound as a colorless oil.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto remove excess reagent
  3. additionThe residue was diluted with aqueous saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on column silica gel with a 10% ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-703d12d38d9b4302aa5220d221c67258
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163935B2

Notizen zur Reaktion

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