Hydrochloric Acid → 4-fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 1493874Notes

Reaction equation

HRID 1493874 reaction equation
[F:1][C:2]1[C:10]2[N:9]=[C:8]([S:11][CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:22].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+].Cl>C(Cl)Cl.O>[F:1][C:2]1[C:10]2[N:9]=[C:8]([S:11]([CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=3)=[O:22])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 156624884-Fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

Product 1

HCID 156624894-fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

4-Fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole (1.31 g, 0.0045 mol) was dissolved in methylene chloride (60 ml). NaHCO3 (0.76 g, 0.0090 mol) dissolved in water (10 ml) was added and the mixture was cooled to +2° C. m-Chloroperbenzoic acid, 84% (1.64 g, 0.0045 mol) dissolved in methylene chloride (10 ml) was added dropwise with stirring. Stirring was continued at +2° C. for 15 min. After separation the organic layer was extracted with an aqueous 0.20M NaOH solution (2×25 ml, 0.010 mol). The combined aqueous solutions were neutralized to pH 7-8 with 0.1M HCl in the presence of methylene chloride (100 ml). After separation the aqueous layer was extracted with methylene chloride and the combined organic solutions were dried over MgSO4. The solution was evaporated and the title compound was obtained (1.06 g, 77%). NMR data for the final product is given below.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. stirringStirring
  4. customAfter separation the organic layer
  5. customAfter separation the aqueous layer
  6. extractionwas extracted with methylene chloride
  7. dry with materialthe combined organic solutions were dried over MgSO4
  8. customThe solution was evaporated

Sources & evidence

ORD record
ord-f6bbf8e35c9d4119a9d1632b67d26793
Source dataset
uspto-grants-1991_06
Patent number
US05025024

Reaction notes

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