m-Chloroperbenzoic acid → HCID 22258920, compound

HRID 412315Notes

Reaction equation

HRID 412315 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-chloroperbenzoic 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-72b4249a5e06426db35f6552cda6cb60
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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