Methyl iodide → HCID 45077823, compound

HRID 1176566Notes

Reaction equation

HRID 1176566 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[NH:3][CH:2]=1.[H-].[Na+].CI.[C:18](=O)([O-])O.[Na+]>CN(C)C=O>[CH3:18][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178497584HCID 178497584, compound

Product 1

HCID 45077823HCID 45077823, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.39 g of methyl 3H-benzimidazole-4-carboxylate are dissolved under argon in 20 ml of N,N-dimethylformamide. The solution is cooled to 0° C. in an ice bath and admixed in portions with 0.299 g of sodium hydride (60% dispersion). 0.744 ml of methyl iodide is added and the reaction mixture is heated to 45° C. over 17 hours. The reaction mixture is subsequently poured onto 50 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with 2:1 tetrahydrofuran/tert-butyl methyl ether (2×150 ml). The combined organic phases are washed with 50 ml each of saturated aqueous sodium hydrogencarbonate solution and water, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F). Rt=1.95.

Workup

  1. temperaturethe reaction mixture is heated to 45° C. over 17 hours
  2. extractionextracted with 2:1 tetrahydrofuran/tert-butyl methyl ether (2×150 ml)
  3. washThe combined organic phases are washed with 50 ml each of saturated aqueous sodium hydrogencarbonate solution and water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ad1f053afca946a58d97208a0f3b9af3
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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