m-Chloroperbenzoic acid → HCID 22258920, compound

HRID 1767399Notes

Reaction equation

HRID 1767399 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[NH:16][C:17](=[O:25])[C:18](=[C:21]([S:23][CH3:24])[CH:22]=1)[C:19]#[N:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[NH:16][C:17](=[O:25])[C:18](=[C:21]([S:23]([CH3:24])=[O:34])[CH:22]=1)[C:19]#[N:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22258959HCID 22258959, compound

Product 1

HCID 22258920HCID 22258920, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 6-[2-(benzyloxy)phenyl]-4-(methylthio)-2-oxo-1,2-dihydro-nicotinonitrile (4.00 g, 11.5 mmol) in CH2Cl2 was added m-chloroper-benzoic acid (mCPBA) (69%, 3.45 g, 13.8 mmol) in one portion. The reaction mixture was stirred at 0° C. to room temperature for 1 hr, quenched with saturated NaHCO3 solution (80 mL) including Na2S2O3.5H2O (5 g), and diluted with CH2Cl2. The separated organic phase was washed with saturated NaHCO3 solution, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residual solid was triturated with diisopropyl ether to give 6-[2-(benzyloxy)phenyl]-4-(methylsulfinyl)-2-oxo-1,2-dihydro-nicotinonitrile as a yellow solid (4.00 g, yield; 96%).

Workup

  1. customquenched with saturated NaHCO3 solution (80 mL)
  2. additiondiluted with CH2Cl2
  3. washThe separated organic phase was washed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residual solid was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-3ac8a960338e4ca180220bc9784dfb27
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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