Hydrochloric Acid → HCID 13732530, compound

HRID 1731283Notes

Reaction equation

HRID 1731283 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:14])CS(C)(=O)=O.ClN1C(=O)CC[C:17]1=O.Cl.[S:24](=[O:28])(=O)(O)[O-:25].[Na+].[C:30]([Cl:34])(Cl)(Cl)[Cl:31]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:14])[C:30]([Cl:34])([Cl:31])[S:24]([CH3:17])(=[O:28])=[O:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 2604211-(2-chlorophenyl)-2-(methylsulfonyl)ethanoneHCID 516919Sodium Bisulfate

Product 1

HCID 13732530HCID 13732530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred mixture of 1-(2-chlorophenyl)-2-methylsulfonylethanone (3.7 g, 0.016 mole) and N-chlorosuccinimide (5.0 g, 0.036 mole) in 20 ml of carbon tetrachloride and 10 ml of methylene chloride was heated until all reactants were in solution. This solution was allowed to cool to room temperature, and 0.2 ml of concentrated hydrochloric acid was added. The reaction flask was irradiated with a 100 watt incandescent lamp for two hours. The resultant mixture was filtered and the filtrate rinsed with methylene chloride. The filtrate was evaporated under reduced pressure to leave an oil. This oil was dissolved in a small amount of methylene chloride and the resultant solution was stirred with 80 ml of saturated aqueous sodium bisulfate for five minutes. This mixture was extracted with methylene chloride and the extract washed in succession with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 3.0 g of 1-(2-chlorophenyl)-2,2-dichloro-2-methylsulfonylethanone as a solid (mp 81°-82° C.).

Workup

  1. temperaturewas heated until all reactants
  2. customThe reaction flask was irradiated with a 100 watt incandescent lamp for two hours
  3. filtrationThe resultant mixture was filtered
  4. washthe filtrate rinsed with methylene chloride
  5. customThe filtrate was evaporated under reduced pressure
  6. customto leave an oil
  7. extractionThis mixture was extracted with methylene chloride
  8. washthe extract washed in succession with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  9. extractionThe washed extract
  10. dry with materialwas dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d92c2c8cf62b4ac0aacbb8a1bd984476
Source dataset
uspto-grants-1986_11
Patent number
US04621078

Reaction notes

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