Potassium Hydroxide → 2,6-Dichloro-3-nitrobenzene-1-sulfonyl chloride

HRID 396276Notes

Reaction equation

HRID 396276 reaction equation
[OH-].[K+].O.O.[Cl:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[S:16]([OH:19])(=O)=[O:17].P(Cl)(Cl)(Cl)(Cl)[Cl:21].O=P(Cl)(Cl)Cl>CO>[Cl:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[S:16]([Cl:21])(=[O:19])=[O:17]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 86587416HCID 86587416, compound

Product 1

HCID 234477722,6-Dichloro-3-nitrobenzene-1-sulfonyl chlorideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (12.07 g, 0.215 mol) was added to a solution of 2,6-dichloro-3-nitrobenzenesulfonic acid dihydrate (44.35 g, 0.144 mol) in MeOH (850 mL) and the reaction was allowed to stir at room temperature for 14 hr. The reaction mixture was concentrated and the resulting solid was dried in vacu overnight. To this was added PCl5 (30.00 g, 0.144 mol) followed by POCl3 (475 mL) and the mixture was refluxed overnight. The reaction was then cooled to room temperature and concentrated. The resulting mixture was taken up in EtOAc and chilled in an ice bath. Ice chunks were slowly added to the reaction mixture to quench any leftover PCl5. When bubbling ceased, water was added and the reaction mix was extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated to yield 2,6-Dichloro-3-nitrobenzenesulfonyl chloride (40.42 g, 97%). 1H NMR (DMSO-d6); 7.88 (d, 1H), 7.75 (d, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting solid was dried in vacu overnight
  3. temperaturethe mixture was refluxed overnight
  4. temperatureThe reaction was then cooled to room temperature
  5. concentrationconcentrated
  6. temperaturechilled in an ice bath
  7. additionIce chunks were slowly added to the reaction mixture
  8. customto quench any leftover PCl5
  9. customWhen bubbling
  10. additionwater was added
  11. additionthe reaction mix
  12. extractionwas extracted with EtOAc
  13. dry with materialThe organic layer was dried (MgSO4)
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-f11c1180041944a986378dfed3417666
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

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