Formaldehyde → N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

HRID 1846834Notes

Reaction equation

HRID 1846834 reaction equation
[OH:1][C:2]1[C:3](=[O:19])[CH:4]=[C:5]([CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[O:6][CH:7]=1.[CH2:20]=[O:21].[OH-].[Na+]>O1CCOCC1>[OH:1][C:2]1[C:3](=[O:19])[CH:4]=[C:5]([CH2:8][NH:9][S:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:12])=[O:11])[O:6][C:7]=1[CH2:20][OH:21]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 86725691N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Product 1

HCID 86725692N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideYield 38.57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (8-01) (1.1 g, 3.92 mmol) in dioxane (20 mL) were added 37% formaldehyde solution (0.47 mL, 4.69 mmol) and aqueous NaOH (1.95 mL, 3.92 mmol, 2M) and the mixture was stirred for 6 h at room temperature. After completion of the reaction, it was concentrated under vacuum to get a crude compound. It was then purified using normal column chromatography to get N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (9-01) (470.0 mg, 38.57%) as a white solid.

Workup

  1. customAfter completion of the reaction, it
  2. concentrationwas concentrated under vacuum
  3. customto get a crude compound
  4. customIt was then purified

Sources & evidence

ORD record
ord-52d879cb17ca43eea604cc474bcd5d63
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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