m-Chloroperbenzoic acid → HCID 66801535, compound

HRID 2366269Notes

Reaction equation

HRID 2366269 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[S:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([F:18])[C:16]=2[N:17]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[S:10][C:11]2[CH:12]=[N+:13]([O-:27])[CH:14]=[C:15]([F:18])[C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66801575HCID 66801575, compound

Product 1

HCID 66801535HCID 66801535, compoundYield 120.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 2-(2,6-dichlorophenyl)-7-fluorothiazolo[5,4-c]pyridine (5.1 g, 17.1 mmol) in DCM (70 mL), was added m-CPBA (11.77 g, 68.2 mmol) over 3 minutes, at 0° C. under argon. The reaction mixture was slowly warmed to room temperature over 1 hour and then stirred at room temperature for 4 hours. The resultant mixture was diluted with DCM (150 mL) and washed with a saturated solution of potassium carbonate (100 mL). Additional amounts of DCM and water were added, followed by MeOH (50 mL). The organic layer was separated, washed with water (300 mL), dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was triturated with water, dried under reduced pressure to afford the title compound as a white solid (6.50 g, quantitative). LCMS (Method F): RT=2.76 min, m/z: 315 [M+H+].

Workup

  1. customat 0° C.
  2. washwashed with a saturated solution of potassium carbonate (100 mL)
  3. additionAdditional amounts of DCM and water were added
  4. customThe organic layer was separated
  5. washwashed with water (300 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was triturated with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-7b37fc467be14777aa649514a7a7a3ff
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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