Benzenesulfonamide, 4-(hydroxymethyl)-N-methyl- → 4-Formyl-N-methylbenzenesulfonamide

HRID 2240775Notes

Reaction equation

HRID 2240775 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 17981768Benzenesulfonamide, 4-(hydroxymethyl)-N-methyl-

Product 1

HCID 143271774-Formyl-N-methylbenzenesulfonamideYield 40.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-hydroxymethyl-N-methyl-benzenesulfonamide (1.61 g, 8.0 mmol) in DCM (50 mL) is added to a mixture of MnO2 (16.1 g, 167 mmol) in DCM (65 mL). The mixture is stirred at rt for 15 min, filtered over celite and the solvent of the filtrate is evaporated to give 4-formyl-N-methyl-benzenesulfonamide (651 mg) as a white solid; LC-MS: tR=0.68 min; 1H NMR (D6-DMSO): δ 10.08 (s, 1H), 8.12-8.07 (m, 2H), 7.98-7.94 (m, 2H), 7.68 (s br, 1H), 2.42 (s, 3H).

Workup

  1. filtrationfiltered over celite
  2. customthe solvent of the filtrate is evaporated

Sources & evidence

ORD record
ord-1074e1bb5cb842f8870e4570d2372693
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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