Benzene → 1161945-63-6

HRID 2283363Notes

Reaction equation

HRID 2283363 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][S:15]([O-:18])(=O)=[O:16])[CH:9]=[CH:10][C:11]=1[Cl:12].[Na+].C1C=CC=CC=1>CN(C)C=O>[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][S:15]([Cl:3])(=[O:18])=[O:16])[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 86632009HCID 86632009, compound

Product 1

HCID 577509391161945-63-6Yield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (1.15 mL, 15.83 mmol) was added dropwise to a suspension of sodium 2-(3,4-dichloro-phenyl)-ethanesulfonate (3.17 g, 11.47 mmol) in a mixture of anhydrous benzene (50 mL) and anhydrous N,N-dimethylformamide (1 mL) at 0° C. The reaction mixture was allowed to warm slowly to room temperature and was then heated at 80° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through a pad of Celite. The solids were washed with benzene and the combined filtrates were concentrated in vacuo. The residue was taken up in hexane and the resulting suspension was heated at 50° C. for 30 min. After cooling to room temperature, a solid was collected by filtration to give 2.20 g (70% yield) of the title compound.

Workup

  1. temperaturewas then heated at 80° C. for 18 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through a pad of Celite
  4. washThe solids were washed with benzene
  5. concentrationthe combined filtrates were concentrated in vacuo
  6. temperaturethe resulting suspension was heated at 50° C. for 30 min
  7. temperatureAfter cooling to room temperature
  8. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-c4a2dc4d11c446efa6f9621cde3c2629
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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