Sodium Thiosulfate → 2-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]sulfinyl}-1H-benzimidazole

HRID 1081681Notes

Reaction equation

HRID 1081681 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[C:9]=1[CH3:25].[O:26]1CCOCC1.[OH-].[Na+].Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15]([C:16]2[NH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[O:26])[C:9]=1[CH3:25]

Participants

5

Reactant 4

HCID 24477Sodium ThiosulfateHCID 97993662-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazoleHCID 18323598NaOH dioxaneHCID 23665760Sodium Hypochlorite

Product 1

HCID 233630272-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]sulfinyl}-1H-benzimidazoleYield 80%

Procedure

2-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole (2 mmol) are dissolved in 15 ml of dioxane + NaOH (6 mmol; 2N), and the solution is treated with 2.5 mmol of 7 percent strength sodium hypochlorite solution at 20° C. Sodium thiosulfate is added, dioxane is distilled off, the pH is brought to 9, the mixture is extracted using dichloromethane, and the product is crystallized from dichloromethane/diisopropyl ether. This gives the title compound (yield 80%) of m.p. 173° C. (decomp.) as a colorless solid.

Workup

  1. distillationdioxane is distilled off
  2. extractionthe mixture is extracted
  3. customthe product is crystallized from dichloromethane/diisopropyl ether

Sources & evidence

ORD record
ord-09a92c57475041feb85166973aedb692
Source dataset
uspto-grants-1996_12
Patent number
US05587389

Reaction notes

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