Water → HCID 19866664, compound

HRID 232079Notes

Reaction equation

HRID 232079 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])=[O:11].CI.[C:21](=O)([O-])[O-].[K+].[K+].O>CN(C)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[S:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 198667142-(1H-Benzimidazol-2-yl sulphinyl)benzenamine

Product 1

HCID 19866664HCID 19866664, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1H-Benzimidazol-2-yl sulphinyl)benzenamine (850 mg, 3.31 mmole) in dimethylformamide (16 ml) and methyl iodide (515 mg, 3.63 mmole) were stirred at room temperature for 6 hours in a stoppered flask in the presence of potassium carbonate (1.66 g, 12 mmole). The mixture was poured into water and extracted with ethyl acetate (3×). The combined extracts were washed with water (3×), dried (anhydrous sodium sulphate) and evaporated to give a pale grey solid which was triturated with ether to give the title compound as an off-white solid (0.78 g; 87%), mp 146°-8° (dec).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with water (3×)
  3. dry with materialdried (anhydrous sodium sulphate)
  4. customevaporated
  5. customto give a pale grey solid which
  6. customwas triturated with ether

Sources & evidence

ORD record
ord-3a275b3d54734455afdc292ba5bbfab8
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Reaction notes

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