Dimethylformamide → HCID 54414738, compound

HRID 1090867Notes

Reaction equation

HRID 1090867 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CN(C)[CH:23]=[O:24].P(Cl)(Cl)([Cl:28])=O>C(Cl)(Cl)Cl>[Cl:28][C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[C:9]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1)[CH:23]=[O:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 112433011-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone

Product 1

HCID 54414738HCID 54414738, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A 54 g quantity (0.18 mole) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone was suspended in a mixture of 500 ml of chloroform and 57 ml (0.74 mole) of N,N-dimethylformamide. To the suspension was added dropwise with stirring 60 ml (0.64 mole) of phosphorus oxychloride over a period of 30 minutes with cooling in an ice-saline solution bath. After the addition, the resulting mixture was further stirred at 20° C. for 2 hours and refluxed with heating for 18 hours. After being cooled to room temperature, the reaction mixture was poured into ice water and extracted with chloroform. The organic layer was washed sequentially with water and a saturated saline solution, dried over magnesium sulfate and concentrated. The resulting crystals were washed with a 1:2 mixture of diethyl ether and n-hexane, giving 54 g (86%) of the desired product in the form of a mixture of E- and Z-isomers as light brown solids.

Workup

  1. additionTo the suspension was added dropwise
  2. temperaturewith cooling in an ice-saline solution bath
  3. additionAfter the addition
  4. temperaturerefluxed
  5. temperaturewith heating for 18 hours
  6. temperatureAfter being cooled to room temperature
  7. extractionextracted with chloroform
  8. washThe organic layer was washed sequentially with water
  9. dry with materiala saturated saline solution, dried over magnesium sulfate
  10. concentrationconcentrated
  11. washThe resulting crystals were washed with a 1:2 mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-cbbb4bc5b94344b2a74a5a14bde823b0
Source dataset
uspto-grants-1992_01
Patent number
US05082974

Reaction notes

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