N-(2-(hydroxymethyl)phenyl)methanesulfonamide → 2-(Methylsulfonamido)benzaldehyde

HRID 1776175Notes

Reaction equation

HRID 1776175 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:1]

Participants

4

Reactant 1

HCID 22955815N-(2-(hydroxymethyl)phenyl)methanesulfonamide

Product 1

HCID 115793042-(Methylsulfonamido)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized according to the method described in WO 2008/073956 A2. To a solution of N-(2-(hydroxymethyl)phenyl)methanesulfonamide (3.44 g, 17.1 mmol) in anhydrous methylene chloride (68 mL) was added manganese dioxide (85% Aldrich, 17 g) and the mixture was stirred at ambient temperature overnight. Additional manganese dioxide (1.6 g) was added and the mixture stirred at 30° C. for 8 hours. The mixture was filtered through Celite, washing with methylene chloride, and the organic solution concentrated. The crude residue was purified by silica gel column chromatography (40-60% ethyl acetate in hexanes) to give a white solid (2.1 g, 62%). 1H NMR (CDCl3, 300 MHz) δ 10.59 (br s, 1H), 9.91 (s, 1H), 7.75-7.59 (m, 3H) 7.28-7.23 (t, 1H, J=7.5 Hz), 3.12 (s, 3H).

Workup

  1. stirringthe mixture stirred at 30° C. for 8 hours
  2. filtrationThe mixture was filtered through Celite
  3. washwashing with methylene chloride
  4. concentrationthe organic solution concentrated
  5. customThe crude residue was purified by silica gel column chromatography (40-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0bc6a7ed187344eabab9d5f92a5e1981
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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