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

HRID 1716843Notes

Reaction equation

HRID 1716843 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 4-((1H-benzimidazol-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.

Workup

  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)

Sources & evidence

ORD record
ord-86ed945bd34c4312a35736767fe9c231
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

Loading…