m-Chloroperbenzoic acid → HCID 59392350, compound

HRID 908091Notes

Reaction equation

HRID 908091 reaction equation
[CH2:1]([NH:3][C:4]1[C:8]2[C:9]([O:13][CH3:14])=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][N:5]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:23])C=1>ClCCl>[CH2:1]([NH:3][C:4]1[C:8]2[C:9]([O:13][CH3:14])=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:23])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57425208HCID 57425208, compound

Product 1

HCID 59392350HCID 59392350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg (0.43 mmol) Ethyl-(4-Methoxy-benzo[d]isothiazol-3-yl)-amine, prepared in analogy to compound example 32, was dissolved in 10 ml dichloromethane. The solution was cooled to 0 C and 100 mg of a 70% m-chlor-perbenzoic acid was added portion wise. The cooling bath was removed and stirring was continued for 30 min at room temperature. The solution was poured into Na2CO3-solution. The layers were separated and the organic layer was washed with Na2CO3-solution and water. The organic layer was dried over NaSO4 and concentrated. The crude product was purified by reverse-phase HPLC (eluent acetonitrile/water) to yield 40 mg (0.18 mmol) of the title product.

Workup

  1. additionwas added portion wise
  2. customThe cooling bath was removed
  3. additionThe solution was poured into Na2CO3-solution
  4. customThe layers were separated
  5. washthe organic layer was washed with Na2CO3-solution and water
  6. dry with materialThe organic layer was dried over NaSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by reverse-phase HPLC (eluent acetonitrile/water)

Sources & evidence

ORD record
ord-d65641090e8b46dfb4e1f54ef5706b4f
Source dataset
uspto-grants-2011_09
Patent number
US08017554B2

Reaction notes

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