Dimethyl Sulfoxide → HCID 54501125, compound

HRID 904825Notes

Reaction equation

HRID 904825 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](=[CH:23][C:24]([OH:26])=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:27])(=[O:6])=[O:5])([CH3:3])[CH3:2].[CH3:28]S(C)=O.[H-].[Na+].CI>O>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](=[CH:23][C:24]([O:26][CH3:28])=[O:25])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:27])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54254101HCID 54254101, compound

Product 1

HCID 54501125HCID 54501125, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 0.77 g. of 1-isopropylsulfonyl-2-amino-6-(α-hydroxycarbonylmethylenebenzyl)benzimidazole (from Example 17) in 10 ml. of dimethylsulfoxide containing 0.1 g. of a fifty percent suspension of sodium hydride in mineral oil was added in one portion 0.3 g. of methyl iodide. The reaction mixture was stirred at room temperature for fifteen minutes, and then was diluted by the addition of 50 ml. of water. The aqueous mixture was extracted several times with ethyl acetate. The extracts were combined, washed with water, dried, and the solvent was removed by evaporation under reduced pressure to provide 1-isopropylsulfonyl-2-amino-6-(α-methoxycarbonylmethylenebenzyl)benzimidazole as a yellow solid.

Workup

  1. additionwas diluted by the addition of 50 ml
  2. extractionThe aqueous mixture was extracted several times with ethyl acetate
  3. washwashed with water
  4. customdried
  5. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-de102f9bbf61456c8f46ac1006a30328
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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