Sodium periodate → HCID 68849826, compound

HRID 29222Notes

Reaction equation

HRID 29222 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:5][CH:6]([CH2:20][CH3:21])[C:7]([NH:9][C:10]([CH3:19])([CH3:18])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][S:16][CH3:17])=[O:8].I([O-])(=O)(=O)=[O:27].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:5][CH:6]([CH2:20][CH3:21])[C:7]([NH:9][C:10]([CH3:19])([CH3:18])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][S:16]([CH3:17])=[O:27])=[O:8]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 688471872-(3,5-dichlorophenoxy)-N-(6-methyl-1-methylthio-hept-4-yn-6-yl) butyramide

Product 1

HCID 68849826HCID 68849826, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-(3,5-dichlorophenoxy)-N-(6-methyl-1-methylthio-hept-4-yn-6-yl) butyramide (0.21 g) in ethanol (2.5 ml) at ambient temperature was added dropwise a solution of sodium periodate (0.13 g) in water (2.5 ml). The mixture was stirred for 2.5 hours, stored for 18 hours then evaporated under reduced pressure. The residue was extracted with dichloromethane and the organic phase filtered then evaporated under reduced pressure to give the required product as a colourless oil, 0.18 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); 2.34-2.42((2H, m); 2.62(3H, s); 2.76-2.84(1H, m); 2.90-2.96(1H, m); 4.34-4.38(1H, m); 6.26(1H, s); 6.82(2H, s); 7.02(1H, s).

Workup

  1. waitstored for 18 hours
  2. customthen evaporated under reduced pressure
  3. extractionThe residue was extracted with dichloromethane
  4. filtrationthe organic phase filtered
  5. customthen evaporated under reduced pressure

Sources & evidence

ORD record
ord-6d81d35f5a974d9d99072eb165a3b2d5
Source dataset
uspto-grants-2008_09
Patent number
US07420090B2

Reaction notes

Loading…