2-chloro-5-(hydroxymethyl)Benzenesulfonamide → 2-Chloro-5-formylbenzene-1-sulfonamide

HRID 734735Notes

Reaction equation

HRID 734735 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11]>CC(C)=O.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11]

Participants

4

Reactant 1

HCID 183743812-chloro-5-(hydroxymethyl)Benzenesulfonamide

Product 1

HCID 146546022-Chloro-5-formylbenzene-1-sulfonamideYield 64.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

A solution of 2-chloro-5-(hydroxymethyl)benzenesulfonamide (696 mg, 3.14 mmol) in acetone (30 mL) was added to a round bottom flask containing MnO2 (2.73 g, 31.4 mmol). The mixture was stirred for 50 hours until the starting material was consumed, then filtered though a pad of celite. The filtrate was evaporated to afford the product (444 mg, 64%) as a white solid. MS (ES+) m/z 220 [M+H]+.

Workup

  1. customwas consumed
  2. filtrationfiltered though a pad of celite
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f1ea02839c7a4730a98c838a195cd9c9
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

Loading…