Isopropylhydroxylamine → N-Isopropyl-alpha-(2sulfofuran-5-yl)nitrone

HRID 1004555Notes

Reaction equation

HRID 1004555 reaction equation
[CH:1]([NH:4][OH:5])([CH3:3])[CH3:2].[CH:6]([C:8]1[O:12][C:11]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:10][CH:9]=1)=O.[Na]>CO>[CH:1]([N+:4]([O-:5])=[CH:6][C:8]1[O:12][C:11]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:10][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 78763Isopropylhydroxylamine2×HCID 27240012-Formylfuran-5-sulfonateHCID 5360545Sodium

Product 1

HCID 73460764N-Isopropyl-alpha-(2sulfofuran-5-yl)nitroneYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Isopropylhydroxylamine (from Example A above) and 5-formylfuran-2-sulfonic acid, sodium salt hydrate (5.94 g) were refluxed in methanol (200 mL) for 24 hours. Another portion of N-isopropylhydroxylamine was added and the reaction stirred for 24 hours. The solvent was stripped to provide a pale yellow solid which was recrystallized from ethyl acetate to afford 5.72 g (75% yield) of the title compound, m.p.=230° C. (decomposed). HPLC analysis showed a major product of 88% by area. Depending upon the pH, the title compound was present as the free acid, or, if in the presence of sodium cations and a higher pH, as the sodium salt. Other salt forms can be prepared by changing the cation.

Workup

  1. customto provide a pale yellow solid which
  2. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fa149e51036448489211b774b6d5518e
Source dataset
uspto-grants-2000_04
Patent number
US06051571

Reaction notes

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