Sodium Carbonate → HCID 22915473, compound

HRID 1377925Notes

Reaction equation

HRID 1377925 reaction equation
[I:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[C:15]([O:19][NH2:20])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[Na+].[Na+]>S(Cl)(Cl)=O.C(OCC)C.O>[C:15]([O:19][NH:20][C:9](=[O:11])[CH2:8][CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:13][CH:12]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 12412295HCID 12412295, compound

Product 1

HCID 22915473HCID 22915473, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 3-(4-iodophenoxy)propanoic acid (1.00 g, 3.42 mmol) in thionyl chloride (6.0 mL) was heated at reflux for 30 minutes. The reaction mixture was cooled to ambient temperature, diluted with ethyl ether, and concentrated in vacuo. The residue was azeotroped three times with ethyl ether, dried under high vacuum, and taken up in dichloromethane (7 mL) under N2. To the solution was added a solution in dichloromethane of O-tert-butylhydroxylamine (8.60 mmol; prepared by dissolving O-tert-butylhydroxylamine hydrochloride in water, making the free base with aqueous 10% Na2CO3, and extracting the solution with dichloromethane, and drying the organic solution over MgSO4), and the reaction mixture was stirred for two hours. The reaction mixture was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow oil which crystallized on standing to give O-tert-butyl 3-(4-iodophenoxy)propanohydroxamic acid (1.22 g, 98%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. concentrationconcentrated in vacuo
  4. customThe residue was azeotroped three times with ethyl ether
  5. customdried under high vacuum
  6. additionTo the solution was added a solution in dichloromethane of O-tert-butylhydroxylamine (8.60 mmol
  7. customprepared
  8. extractionextracting the solution with dichloromethane
  9. dry with materialdrying the organic solution over MgSO4), and the reaction mixture
  10. washThe reaction mixture was washed with saturated aqueous NaHCO3 and brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customto give a yellow oil which
  15. customcrystallized

Sources & evidence

ORD record
ord-9fd05fb35ff14733aaa9e82f818de036
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

Loading…