Sodium Hydroxide → HCID 178527212, compound

HRID 728643Notes

Reaction equation

HRID 728643 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([S:9][CH2:10][C:11]3[CH:16]=[C:15]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)[CH:14]=[CH:13][N:12]=3)=[N:8][C:4]=2[CH:3]=1.C([O-])(O)=[O:25].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([S:9]([CH2:10][C:11]3[CH:16]=[C:15]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)[CH:14]=[CH:13][N:12]=3)=[O:25])=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178505473HCID 178505473, compound

Product 1

HCID 178527212HCID 178527212, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

5- Fluoro-2-[[(4-cyclopropylmethoxy-2-pyridinyl)methyl]thio]-1H-benz-imidazole (1.25 g, 0.0036 mol) was dissolved in CH2Cl2 (40 ml). NaHCO3 (0.6 g, 0.0072 mol) dissolved in H2O (20 ml) was added and the mixture was cooled to +2° C. m-Chloroperbenzoic acid, 84% (0.73 g, 0.0036 mol) dissolved in CH2Cl2 (5 ml) was added under stirring. Stirring was continued at room temperature for 15 min. The two phases were separated and NaOH (0.29 g, 0.0072 mol) dissolved in H2O (25 ml) was added to the organic phase. The mixture was stirred, the phases were separated and the H2O phase was treated with Norite and filtered. Methylformiate (0.45 ml, 0.0073 mol) dissolved in H2O (5 ml) was added dropwise under stirring. After extraction with CH2Cl2 and drying with Na2SO4 the solvent was evaporated. In this way the title compound was obtained [0.93 g, 69%). NMR data for the final product is given below. NMR data for the intermediates are given below.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringStirring
  4. customThe two phases were separated
  5. additionwas added to the organic phase
  6. stirringThe mixture was stirred
  7. customthe phases were separated
  8. additionthe H2O phase was treated with Norite and
  9. filtrationfiltered
  10. dissolutionMethylformiate (0.45 ml, 0.0073 mol) dissolved in H2O (5 ml)
  11. additionwas added dropwise
  12. stirringunder stirring
  13. extractionAfter extraction with CH2Cl2
  14. dry with materialdrying with Na2SO4 the solvent
  15. customwas evaporated

Sources & evidence

ORD record
ord-5c532a7b6b60420f96b48b1fb54df108
Source dataset
uspto-grants-1991_09
Patent number
US05049674

Reaction notes

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