2-Formylfuran-5-sulfonate → N-n-Hexyl-alpha-(2-sulfofuran-5-yl)nitrone

Reaction equation

[CH:1]([C:3]1[O:7][C:6]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:5][CH:4]=1)=O.[Na].[CH2:13]([NH:19][OH:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>>[CH2:13]([N+:19]([O-:20])=[CH:1][C:3]1[O:7][C:6]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:5][CH:4]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 3

HCID 27240012-Formylfuran-5-sulfonate

HCID 5360545Sodium2×

HCID 10329276N-n-hexylhydroxylamine

Product 1

HCID 85044882N-n-Hexyl-alpha-(2-sulfofuran-5-yl)nitroneYield 76%

Procedure

Following the procedure of Example 1 above and using 5-formylfuran-2-sulfonic acid, sodium salt hydrate and N-n-hexylhydroxylamine, the title compound was prepared in 76% yield as the sodium salt, m.p. 225.5° C. (dec.).

Sources & evidence

ORD record: ord-95af23860cc847f094f4ad666dfca112
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376540B1

Reaction notes

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