Water → HCID 14371286, compound

HRID 476892Notes

Reaction equation

HRID 476892 reaction equation
[CH3:1][N:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:3]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4].[H-].[Na+].[CH3:22]I.O>CS(C)=O>[CH3:22][N:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=[C:5]1[C:3]([N:2]([CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14371283HCID 14371283, compound

Product 1

HCID 14371286HCID 14371286, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-Methyl-N-(2-pyridyl)benzimidazole-2-carboxamide (1.0 g) prepared in Example 5 was suspended in dry DMSO (20 ml), sodium hydride (0.16 g) was added in an argon atmosphere and stirred at room temperature for 1 hr. Methyl iodide (0.62 g) was added and stirred at room temperature for 2 hrs. The mixture was poured into water and extracted with chloroform. The chloroform layer was dried over anhydrous Na2SO4, and the solvent was distilled off to obtain the residue. Purification of the residue by column chromatography on silica gel gave the title compound (0.99 g).

Workup

  1. stirringstirred at room temperature for 2 hrs
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous Na2SO4
  4. distillationthe solvent was distilled off
  5. customto obtain the residue
  6. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-2e2be06aad1248ce9bd003dd75aa265a
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Reaction notes

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