Hydroxylamine → 6-Benzenesulfonyl-hexa-2,4-dienoic acid hydroxyamide

HRID 2245770Notes

Reaction equation

HRID 2245770 reaction equation
[C:1]1([S:7]([CH2:10][CH:11]=[CH:12][CH:13]=[CH:14][C:15]([OH:17])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH2:24][OH:25]>ClCCl.O1CCCC1>[OH:25][NH:24][C:15](=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH2:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 65578Oxalyl chlorideHCID 850932106-Benzenesulfonyl-hexa-2,4-dienoic acid

Product 1

HCID 850788096-Benzenesulfonyl-hexa-2,4-dienoic acid hydroxyamideYield 31%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-benzenesulfonyl-hexa-2,4-dienoic acid (0.292 g, 1.15 mmol) in dry dichloromethane (5 mL) was added dropwise oxalyl chloride, at 0° C. under an atmosphere of argon. One drop on dimethylformamide was then added. After stirring at 2020 C. for one hour, a solution of aqueous hydroxylamine (50%, 0.17 mL, 2.5 mmol) in tetrahydrofuran (5 mL) was added. The mixture was stirred for an additional hour and concentrated under reduced pressure to give a yellow foam that was purified by column chromatography (8:2 ethyl acetate:40-60° C. petroleum to 100% ethyl acetate). The title compound (91 mg, 31%) was obtained as a white foam.

Workup

  1. customat 0° C.
  2. additionOne drop on dimethylformamide was then added
  3. stirringThe mixture was stirred for an additional hour
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow foam that
  6. customwas purified by column chromatography (8:2 ethyl acetate:40-60° C. petroleum to 100% ethyl acetate)

Sources & evidence

ORD record
ord-a64460d40b9942278d1bca8fcc184529
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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