Dimethylformamide → Methyl 2-phenylsulphenyl-4-trifluoromethylbenzoate

HRID 2380201Notes

Reaction equation

HRID 2380201 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 filtrate was evaporated to dryness and the residue was triturated with cyclohexane and filtered to give methyl 2-(phenylsulphenyl)-4-trifluoromethylbenzoate (10.5 g) 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 filtrate was evaporated to dryness
  13. customthe residue was triturated with cyclohexane
  14. filtrationfiltered

Sources & evidence

ORD record
ord-08670a4638c34cd8a1229228e657cb2f
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Reaction notes

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