Trityl chloride → methyl N-triphenylmethyl-5-benzimidazolecarboxylate

HRID 352843

Reaktionsgleichung

Reaktionsgleichung von HRID 352843
Cl.[N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:5]=2[NH:4][CH:3]=1.C(N(CC)CC)C.[C:22]1([C:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[C:22]1([C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:2]2[C:6]3[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:5]=3[N:4]=[CH:3]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 22710297methyl 1H-benzimidazole-5-carboxylate hydrochloride

Produkt 1

HCID 22710354methyl N-triphenylmethyl-5-benzimidazolecarboxylateAusbeute 106,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In dichloromethane (15 ml), methyl 5-benzimidazolecarboxylate hydrochloride (1.00 g) was suspended. To the resulting suspension, triethylamine (1.50 ml) and triphenylmethyl chloride (1.50 g) were added, followed by stirring at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1), whereby title compound (2.10 g, quant.) was obtained as a yellow solid.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under reduced pressure
  5. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-af0bf4a0bddb49e6b50c4a70c60ee1ea
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747023B1

Verknüpfte Notizen

Wird geladen…