Methyl iodide → HCID 58577771, compound

HRID 587530Notes

Reaction equation

HRID 587530 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[NH:11][C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[N:8]=1)(=[O:6])=[O:5].[CH3:16]I.[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH3:16][N:11]1[C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[N:8]=[C:7]1[S:4]([CH3:3])(=[O:5])=[O:6]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 585774122-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-benzimidazole

Product 1

HCID 58577771HCID 58577771, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (55.8 mg) (60% in mineral oil) was added to a solution of 2-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-benzimidazole (233 mg) and MeI (0.080 mL) in DMF (dry) (10 mL) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The reaction mixture was diluted with MeOH (2 mL), and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane) to give 1-methyl-2-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-benzimidazole (200 mg) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-0fbc63aa96c44d32b3b2c63cae2cb6b1
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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