Water → HCID 67172008, compound

HRID 1256148Notes

Reaction equation

HRID 1256148 reaction equation
[CH2:1]([S:3][CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:23])C=1.[OH2:26]>C(Cl)Cl>[CH2:1]([S:3]([CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)(=[O:23])=[O:26])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 67172733HCID 67172733, compound

Product 1

HCID 67172008HCID 67172008, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-(3-(ethylthiomethyl)phenyl)acetamide (1 g, 5 mmol) in DCM (10 mL) was added mCPBA (2.4 g, 14 mol). The reaction mixture was stirred at 40° C. overnight. Then water was added, the organic layer was separated and washed with an aqueous of NaHCO3, dried over Na2SO4, concentrated and purified by silica gel chromatography (petroleum ether:EtOAc=1:0 to 5:1) to give N-(3-(ethylsulfonylmethyl)phenyl)acetamide (1 g, 87% yield) as a white solid. 1H NMR: (400 MHz, CDCl3) δ 7.84 (s, 1H), 7.61 (s, 1H), 7.41 (d, 1H), 7.24 (t, 1H), 7.14 (d, 1H), 4.14 (s, 2H), 2.90-2.85 (m, 2H), 2.12 (s, 3H), 1.34 (t, 3H).

Workup

  1. customthe organic layer was separated
  2. washwashed with an aqueous of NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (petroleum ether:EtOAc=1:0 to 5:1)

Sources & evidence

ORD record
ord-7fc3d25744d0461880f60bcf4a4cdf2e
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…