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Imidazole → HCID 70104971, Verbindung

HRID 1533750
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1533750
[OH:1][CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:5]=2[N:4]=1.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1.O>CN(C)C=O>[O:1]([CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:5]=2[N:4]=1)[Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
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Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 18355048Methyl 2-(hydroxymethyl)-1H-benzimidazole-7-carboxylate

Produkt 1

HCID 70104971HCID 70104971, VerbindungAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of methyl 2-hydroxymethyl-1 H-benzimidazole-4-carboxylate (1.0 g) in N,N-dimethylformamide (10 ml) were added tert-butylchlorodiphenylsilane (1.87 g) and imidazole (495 mg) at ambient temperature and the mixture was stirred at the same temperature for 28 hours. The reaction mixture was poured into water and the aqueous solution was extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (10:1) to give methyl 2-tert-butyldiphenylsiloxymethyl-1 H-benzimidazole-4-carboxylate (1.45 g) as an oil.

Aufarbeitung

  1. extractionthe aqueous solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-aec23a1734844b7fa4fcbd9722506271
Quelldatensatz
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06207693B1

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