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

HRID 1665913Notes

Reaction equation

HRID 1665913 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-408f2e47c43e4d1c9daab3045811d9f5
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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