2-chloro-5-(hydroxymethyl)Benzenesulfonamide → 2-Chloro-5-formylbenzene-1-sulfonamide
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]>O1CCCC1.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
Product 1
Reagents, catalysts & solvents 2
Procedure
To a well stirred solution of 2-chloro-5-hydroxymethyl-benzenesulfonamide (31.6 g, 143 mmol) in 300 mL tetrahydrofuran is added 62.0 g (713 mmol) of MnO2. The resulting solution is heated at reflux for 16 h, filtered through Celite then through a 0.4 μM Teflon filter and the filtrate is concentrated in vacuo to remove the tetrahydrofuran. Trituration with hexanes provided 25 g (80%) of the title compound as a grey solid.
Workup
- temperatureThe resulting solution is heated
- temperatureat reflux for 16 h
- filtrationfiltered through Celite
- filtrationthrough a 0.4 μM Teflon filter
- concentrationthe filtrate is concentrated in vacuo
- customto remove the tetrahydrofuran
Sources & evidence
- ORD record
- ord-97c2879080eb4127ae7ed3fae861aa0f
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222424B2
Reaction notes
Loading…