4-(Hydroxymethyl)benzenesulfonamide → 4-Sulfamoylbenzaldehyde

HRID 1585070Notes

Reaction equation

HRID 1585070 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>CC(C)=O.C(Cl)Cl.CCOCC>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:7][CH:8]=1)=[O:1]

Participants

6

Reactant 2

HCID 100811624-(Hydroxymethyl)benzenesulfonamideHCID 178418287HCID 178418287, compound

Product 1

HCID 1510884-SulfamoylbenzaldehydeYield 54%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(hydroxymethyl)benzenesulfonamide (Step 3) (3.75 g, 20 mmol) in a mixture of acetone (250 ml) and methylene chloride (250 ml), pyridinium chlorochromate (6.47 g, 30 mmol) was added. After stirring at room temperature for 5 hours, the reaction mixture was diluted with ether and filtered through a short silica gel column. The column was eluted with hexane/ethyl acetate, (1/1). The fractions containing the desired material were combined and concentrated to give a white solid (2.0 g, 53%): mp 104-106° C. Anal Calc'd. for C7H7NSO3 : C, 45.40; H, 3.81; N, 7.56; S, 17.31. Found: C, 45.61; H, 3.59; N, 7.18; S, 16.27.

Workup

  1. additionwas added
  2. filtrationfiltered through a short silica gel column
  3. washThe column was eluted with hexane/ethyl acetate, (1/1)
  4. additionThe fractions containing the desired material
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-04a0b2320ff04e379c1f97909d564837
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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