Sodium Bicarbonate → HCID 59682298, compound

HRID 2043275Notes

Reaction equation

HRID 2043275 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[C:7]([O-])(O)=O.[Na+].[Cl:12][C:13]1[C:29]([Cl:30])=[CH:28][C:16]2[N:17]([CH2:25]SC)[C:18]([CH2:20][C:21]([F:24])([F:23])[F:22])=[N:19][C:15]=2[CH:14]=1>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[Cl:12][C:13]1[C:29]([Cl:30])=[CH:28][C:16]2[N:17]([CH2:25][S:3]([CH3:7])(=[O:5])=[O:2])[C:18]([CH2:20][C:21]([F:24])([F:22])[F:23])=[N:19][C:15]=2[CH:14]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite2×HCID 59682313HCID 59682313, compound

Product 1

HCID 59682298HCID 59682298, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Oxone® (614.8 mg, 1 mmol) was dissolved in water (10 ml) and the pH was adjusted to pH7 with NaHCO3. To the solution was then added tetrabutylammonium hydrogen sulfate (20 mg). The resulting solution was added at room temperature to a solution of 5,6-dichloro-1-methylsulfanylmethyl-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole, prepared as in Example 47, (109.6 mg, 0.33 mmol) in EtOAc (4 mL). The Oxone® solution (608.87 mg) was added until the reaction completed. The resulting mixture was washed with 1N NaOH, then extracted with EtOAc. The organic layer was washed with 15% NaCl, dried over MgSO4 and the solvent was distilled under reduced pressure to yield the title compound as a yellow solid.

Workup

  1. washThe resulting mixture was washed with 1N NaOH
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with 15% NaCl
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-e6a8e5663b0e4ed59a71f2f7fc9a7383
Source dataset
uspto-grants-2013_11
Patent number
US08586616B2

Reaction notes

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