Reaktion #2028892

ord-6f1cf560ed8e450d9d3713ae1c50e0ce

Reaktionsgleichung

NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(CBr)c2-c2ccccc2)cc1
compound
NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(CBr)c2-c2ccccc2)cc1
4-[4-bromomethyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
Cc1cc(C)nc(C)c1
collidine
CS(C)=O
dimethyl sulfoxide
NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(C=O)c2-c2ccccc2)cc1
desired product
Ausbeute 66.0%
NS(=O)(=O)c1ccc(-n2nc(C(F)(F)F)c(C=O)c2-c2ccccc2)cc1
4-[4-formyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
Ausbeute 66.0%

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction solution was partitioned between ethyl acetate and water
  2. 2
    Waschenthe organic solution was washed with water
  3. 3
    Sonstigedried
  4. 4
    Einengenconcentrated
  5. 5
    SonstigeThe residue was chromatographed (1:1 hexane:ethyl acetate)

Vorschrift

To a solution of the compound prepared in Step 1 (362 mg, 0.79 mmol) in dimethyl sulfoxide (7 mL) was added collidine (0.14 mL, 1.0 mmol). The solution was heated at 120° C. for 3 hours and then kept at overnight at room temperature. The reaction solution was partitioned between ethyl acetate and water and the organic solution was washed with water, dried and concentrated. The residue was chromatographed (1:1 hexane:ethyl acetate) to give the desired product (205 mg, 66%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE044048E1uspto-grants-2013_03