m-Chloroperbenzoic acid → HCID 69309553, compound

HRID 1947035Notes

Reaction equation

HRID 1947035 reaction equation
[CH2:1]([N:3]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=1)[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH2:1]([N:3]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:23]([CH3:24])=[O:33])[N:18]=1)[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69307229HCID 69307229, compound

Product 1

HCID 69309553HCID 69309553, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

N-ethyl-N-[1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indol-4-yl]-methanesulfonamide (0.4 g) in CHCl3 (60 mL) was cooled to 0° C. and MCPBA (0.247 g) added and stirred at 0° C. for 5 h before quenching with 10% sodium thiosulfate solution. The organic layer was separated, dried over sodium sulfate, filtered, concentrated and purified on a column using 100% DCM to 15% MeOH/DCM to yield N-ethyl-N-[1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-indol-4-yl]-methanesulfonamide (0.386 g).

Workup

  1. custombefore quenching with 10% sodium thiosulfate solution
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on a column

Sources & evidence

ORD record
ord-deca4d7fa4674e068be8c1189a7efa21
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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