N-[2-chloro-5-(1-hydroxy-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide → N-(5-acetyl-2-chloro-phenyl)-3,4-dimethoxy-benzenesulfonamide

HRID 1674630Notes

Reaction equation

HRID 1674630 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)(=[O:14])=[O:13]>C(Cl)Cl.C1COCC1.O=[Mn]=O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)(=[O:14])=[O:13])[CH:4]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 1

HCID 57511305N-[2-chloro-5-(1-hydroxy-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide

Product 1

HCID 57511306N-(5-acetyl-2-chloro-phenyl)-3,4-dimethoxy-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution of N-[2-chloro-5-(1-hydroxy-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide (1.85 g, 5 mmol) in DCM/THF (1:1, 10 mL) was treated with MnO2 (10.8 g, 25 eq). The mixture was stirred at RT for 7 h, filtered over Celite and concentrated. The residue was purified by chromatography on SiO2 (hex/EA 1:1). The product was recovered as a colourless foam (1.58 g, 86%).

Workup

  1. filtrationfiltered over Celite
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on SiO2 (hex/EA 1:1)
  4. customThe product was recovered as a colourless foam (1.58 g, 86%)

Sources & evidence

ORD record
ord-db8faeb86a3c4583963aa6d9f2509fbe
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

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