Sodium Carbonate → HCID 22915484, compound

HRID 1377907Notes

Reaction equation

HRID 1377907 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O.C(Cl)(=O)C(Cl)=O.[CH2:21]([O:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.CN(C=O)C>[CH2:21]([O:28][NH:29][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][O:5][C:4]1[CH:12]=[CH:13][CH:14]=[C:2]([I:1])[CH:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 102313O-BenzylhydroxylamineHCID 22915471HCID 22915471, compound

Product 1

HCID 22915484HCID 22915484, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution in dichloromethane (20 mL) containing a few drops of DMF of 4-(3-iodophenoxy)butanoic acid (2.26 g, 7.38 mmol) was added oxalyl chloride (0.60 mL, 6.9 mmol) slowly via syringe. The reaction mixture was stirred for 30 minutes at ambient temperature, and then was decanted into a dichloromethane solution of O-benzylhydroxylamine (3.5 g, 22 mmol; prepared by shaking O-benzylhydroxylamine in a mixture of dichloromethane and saturated aqueous Na2CO3, separating the layers, and drying the organic phase over MgSO4). The reaction mixture was stirred for 3.5 hours at ambient temperature and then was extracted with water and saturated aqueous Na2CO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give a white solid. The solid was dissolved in dichloromethane and the organic solution was washed with aqueous 1M HCl, dried over MgSO4, filtered, and concentrated in vacuo to give O-benzyl-4-(3-iodophenoxy)butanohydroxamic acid (3.12 g) as a fluffy white solid.

Workup

  1. customwas decanted into a dichloromethane solution of O-benzylhydroxylamine (3.5 g, 22 mmol
  2. customprepared
  3. customseparating the layers
  4. dry with materialdrying the organic phase over MgSO4)
  5. stirringThe reaction mixture was stirred for 3.5 hours at ambient temperature
  6. extractionwas extracted with water and saturated aqueous Na2CO3
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a white solid
  11. washthe organic solution was washed with aqueous 1M HCl
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9b2e3c9ef7845bba52e0dbd13a5f0f7
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

Loading…