m-Chloroperbenzoic acid → 2-(3,5-dichlorophenoxy)-N-(6-methyl-1-methylsulfonyl-hept-4-yn-6-yl) butyramide

HRID 29223Notes

Reaction equation

HRID 29223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[O:5][CH:6]([CH2:21][CH3:22])[C:7]([NH:9][C:10]([CH3:20])([CH3:19])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][S:16]([CH3:18])=[O:17])=[O:8].ClC1C=CC=C(C(OO)=[O:35])C=1.CCCCCC.C(OCC)(=O)C>ClCCl>[Cl:26][C:24]1[CH:23]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:25]=1)[O:5][CH:6]([CH2:21][CH3:22])[C:7]([NH:9][C:10]([CH3:19])([CH3:20])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][S:16]([CH3:18])(=[O:35])=[O:17])=[O:8]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 21226206Ethyl acetate hexaneHCID 68849826HCID 68849826, compound

Product 1

HCID 688479402-(3,5-dichlorophenoxy)-N-(6-methyl-1-methylsulfonyl-hept-4-yn-6-yl) butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(3,5-dichlorophenoxy)-N-(6-methyl-1-methylsulphinyl-hept-4-yn-6-yl) butyramide (0.10 g) in dichloromethane (5 ml) at 0° C. was added 3-chloroperbenzoic acid (0.060 g, 70%, stabilised with water). The mixture was stirred for 0.5 hours at 0° C., then for 1 hour at ambient temperature and stored for 18 hours. The solvent was evaporated under reduced pressure and the residue dissolved in diethyl ether, washed with a saturated aqueous solution of sodium hydrogen carbonate (three times) and water (twice), dried over magnesium sulphate and then evaporated under reduced pressure to give a colourless oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 2:1 by volume) to give the required product as a pale yellow oil, 0.040 g, 1H NMR (CDCl3) δ: 0.98-1.02(3H, t); 1.56(3H, s); 1.58(3H, s); 1.92-2.00(4H, m); 2.36-2.40((2H, t); 2.96(3H, s); 3.22-3.26(2H, m); 4.38-4.42(1H, t); 6.26(1H, s); 6.84(2H, s); 7.02(1H, s).

Workup

  1. waitfor 1 hour at ambient temperature
  2. waitstored for 18 hours
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue dissolved in diethyl ether
  5. washwashed with a saturated aqueous solution of sodium hydrogen carbonate (three times) and water (twice),
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customto give a colourless oil

Sources & evidence

ORD record
ord-7c04e26cbb2a432ea4a154f264a4d2c5
Source dataset
uspto-grants-2008_09
Patent number
US07420090B2

Reaction notes

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