Reaction #74648

Reaction equation

HCl

2-iodo-4-(trifluoromethoxy)phenol

potassium carbonate

3-cyano-4-fluoro-N-[1,2,4]thiadiazol-5-yl-benzenesulfonamide

→

title compound

3-cyano-N-(1,2,4-thiadiazol-5-yl)-4-[2-iodo-4-(trifluoromethoxy)phenoxy]benzenesulfonamide

Solvents

ethyl acetate

Dimethylsulfoxide

Conditions

Workup

1. 1
   OtherThe organic layer was collected
2. 2
   Washwashed with brine (20 mL)
3. 3
   Dryingdried over sodium sulphate
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe residue was triturated in dichloromethane
6. 6
   Filtrationfiltered

Procedure

To a suspension of 2-iodo-4-(trifluoromethoxy)phenol (Preparation 226, 600 mg, 1.97 mmol) and potassium carbonate (1125 mg, 8.14 mmol) in Dimethylsulfoxide (10 mL) was added 3-cyano-4-fluoro-N-[1,2,4]thiadiazol-5-yl-benzenesulfonamide (Preparation 65). The reaction was heated to 80° C. under N2 for 7 hours before the addition of ethyl acetate (20 mL) and 3M aqueous HCl solution (30 mL). The organic layer was collected, washed with brine (20 mL), dried over sodium sulphate and concentrated in vacuo. The residue was triturated in dichloromethane and filtered to afford 965 mg of the title compound.

Source