Sodium Methoxide → HCID 15840176, compound

HRID 1900701Notes

Reaction equation

HRID 1900701 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:7](C=S(=O)=O)=[N:8][C:4]=2[CH:3]=1.ClC1C=CC2N=C(C=S(=O)=O)N(CC3C=C[C:42]4[O:45]COC=4C=3)C=2C=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:7]([O:45][CH3:42])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 18980310HCID 18980310, compoundHCID 18980327HCID 18980327, compound

Product 1

HCID 15840176HCID 15840176, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

448 mg of a mixture comprising 5-chloro-2-sulfonylmethyl-1-(3,4-methylenedioxybenzyl)benzimidazole and 6-chloro-2-sulfonylmethyl-1-(3,4-methylenedioxybenzyl)benzimidazole was dissolved in 20 ml of methanol, followed by the addition of 10 ml of 28% sodium methoxide. The obtained mixture was heated under reflux for 1.5 hours, cooled with ice, neutralized with 104 aqueous hydrochlic acid, and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated in a vacuum. The residue was subjected to silica gel column chromatography to give the title compound.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled with ice
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-dac3dd3e0dea4e518cf280ab06f8bd16
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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