Methyl iodide → Methyl 4-((1-Methyl-1H-benzimidazol-2-yl)methyl)benzoate

HRID 1163087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1163087
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:21][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59468704methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate

Produkt 1

HCID 59468706Methyl 4-((1-Methyl-1H-benzimidazol-2-yl)methyl)benzoateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate (0.2 g, 0.75 mmol) in acetone was treated with potassium carbonate (0.31 g, 2.2 mmol), cooled to 0° C., treated dropwise with and methyl iodide (0.070 mL, 1.1 mmol), heated at 40° C. for 12 h, cooled to room temperature, and filtered. The filtrate was evaporated under reduced pressure. Purification of the resultant residue by column chromatography (silica, chloroform) afforded the title product (28%). 1H NMR (400 MHz, CDCl3): 7.98 (d, J=8.4 Hz, 2H), 7.7 (m, 1H), 7.37 (m,5H), 4.38 (s, 2H), 3.9 (s, 3H), 3.5 (s, 3H). [M+H] 281.

Aufarbeitung

  1. temperatureheated at 40° C. for 12 h
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customPurification of the resultant residue by column chromatography (silica, chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-42c45dc29a8646809c544ccce74584c4
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820825B2

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