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

HRID 1810142Notes

Reaction equation

HRID 1810142 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

HCID 183743812-chloro-5-(hydroxymethyl)Benzenesulfonamide

Product 1

HCID 146546022-Chloro-5-formylbenzene-1-sulfonamideYield 80%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

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

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered through Celite
  4. filtrationthrough a 0.4 μM Teflon filter
  5. concentrationthe filtrate is concentrated in vacuo
  6. customto remove the tetrahydrofuran

Sources & evidence

ORD record
ord-8ce38f1657754729a5893384d7fb0de5
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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