N-(2-chloro-5-hydroxymethyl-phenyl)-3,4-dimethoxy-benzenesulfonamide → N-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamide

HRID 1674628Notes

Reaction equation

HRID 1674628 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12]>C(Cl)Cl.C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12]

Participants

4

Reactant 1

HCID 57511303N-(2-chloro-5-hydroxymethyl-phenyl)-3,4-dimethoxy-benzenesulfonamide

Product 1

HCID 57511304N-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution of N-(2-chloro-5-hydroxymethyl-phenyl)-3,4-dimethoxy-benzenesulfonamide (2.53 g, 7 mmol) in DCM/THF (1:1, 16 mL) was treated with MnO2 (12.3 g, 20 eq). The mixture was stirred at RT for 6 h, filtered over Celite and concentrated. The residue purified by chromatography on SiO2 (hex/EA 1:1, EA). The product was recovered as a pinkish oil (1.95 g, 77%).

Workup

  1. filtrationfiltered over Celite
  2. concentrationconcentrated
  3. customThe residue purified by chromatography on SiO2 (hex/EA 1:1, EA)
  4. customThe product was recovered as a pinkish oil (1.95 g, 77%)

Sources & evidence

ORD record
ord-e31127aa21334784ac5ee4eb675673f3
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

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