Methyl iodide → HCID 19866681, compound

HRID 1199464Notes

Reaction equation

HRID 1199464 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1.CI.[C:20](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[CH3:20][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[S:2][CH3:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 123160831H-Benzimidazole, 2-[2-(methylthio)phenyl]-

Product 1

HCID 19866681HCID 19866681, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The product of step (a) above (3.25 g), methyl iodide (1.92 g) and potassium carbonate (5.2 g) were stirred together in dry dimethylformamide (50 ml) at room temperature for 24 hours. The reaction mixture was poured into brine and extracted into ethyl acetate, the extract was washed with excess brine, dried over magnesium sulphate and evaporated to dryness in vacuo and the residue was purified by flash chromatography (SiO2 /CH2Cl2 9:1 ethyl acetate) to afford the sub-title compound as yellow solid, MS MW 254 bp 239.

Workup

  1. extractionextracted into ethyl acetate
  2. washthe extract was washed with excess brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness in vacuo
  5. customthe residue was purified by flash chromatography (SiO2 /CH2Cl2 9:1 ethyl acetate)

Sources & evidence

ORD record
ord-42976fe0c28b40e28a0f396355ff0402
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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