Dimethylformamide → Methyl 2-phenylsulphenyl-4-trifluoromethylbenzoate

HRID 21454Notes

Reaction equation

HRID 21454 reaction equation
[C:1]1([S:7][C:8]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:25]N(C=O)C>ClC(Cl)C>[C:1]1([S:7][C:8]2[CH:16]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:14]=[CH:13][C:9]=2[C:10]([O:12][CH3:25])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 189779402-Phenylsulphenyl-4-trifluoromethylbenzoic acid

Product 1

HCID 18977929Methyl 2-phenylsulphenyl-4-trifluoromethylbenzoate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneCatalyst

Procedure

A solution of 2-(phenylsulphenyl)-4-trifluoromethylbenzoic acid (11.5 g) and thionyl chloride (11.4 g) in dichloroethane containing a few drops of DMF was heated at reflux for 1.5 hours. The mixture was evaporated to dryness and methanol was added. The mixture was heated at reflux for 1 hour and evaporated to dryness. It was treated with water and extracted with ether, washed with sodium carbonate solution (2M), water, dried (Na2SO4) and filtered. The flitrate was evaporated to dryness and the residue was triturated with cyclohexane and filtered to give methyl 2-(phenylsulphenyl)-4-trifluoromethylbenzoate (10.5g) as a white solid, m.p. 55°-60° C.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe mixture was evaporated to dryness and methanol
  3. additionwas added
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 1 hour
  6. customevaporated to dryness
  7. additionIt was treated with water
  8. extractionextracted with ether
  9. washwashed with sodium carbonate solution (2M), water
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customThe flitrate was evaporated to dryness
  13. customthe residue was triturated with cyclohexane
  14. filtrationfiltered

Sources & evidence

ORD record
ord-8f4a28a368f347f9ba098d35902c4585
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Reaction notes

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