3-tert-Butylbenzene-1-sulfonyl chloride → 3-(1,1-dimethylethyl)-N-(2-iodo-6-trifluoromethylpyridin-3-yl)benzenesulfonamide

HRID 1035325Notes

Reaction equation

HRID 1035325 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:11](Cl)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[I:15][C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([C:23]([F:26])([F:25])[F:24])[N:17]=1>N1C=CC=CC=1.O>[CH3:2][C:1]([C:5]1[CH:6]=[C:7]([S:11]([NH:22][C:21]2[C:16]([I:15])=[N:17][C:18]([C:23]([F:25])([F:24])[F:26])=[CH:19][CH:20]=2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 27572473-tert-Butylbenzene-1-sulfonyl chlorideHCID 534254792-Iodo-6-(trifluoromethyl)pyridin-3-amine

Product 1

HCID 866741283-(1,1-dimethylethyl)-N-(2-iodo-6-trifluoromethylpyridin-3-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

9.07 g (38.96 mM) of 3-tert-butylbenzenesulfonyl chloride were added to a solution of 6.60 g (22.92 mM) of 2-iodo-6-trifluoromethylpyridin-3-ylamine in 10.0 mL of pyridine. This reaction mixture was stirred at room temperature overnight. The medium was diluted with water and then extracted with ethyl acetate. The organic phase was washed with 1N hydrochloric acid solution and then dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 14.40 g of the evaporation residue were dissolved in 50.0 mL of 1,4-dioxane, 56.4 mL (169.28 mM) of 3M potassium hydroxide were added, and the reaction mixture was then refluxed for 1 hour. The medium was concentrated under reduced pressure. The residue was dissolved in water, and the solution was acidified with concentrated hydrochloric acid and then extracted twice with DCM. The organic phase was dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was washed with petroleum ether and then filtered on a Büchner funnel. The title product was obtained in the form of a white solid (8.80 g, yield=86%). m.p.=125° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with 1N hydrochloric acid solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolution14.40 g of the evaporation residue were dissolved in 50.0 mL of 1,4-dioxane
  7. addition56.4 mL (169.28 mM) of 3M potassium hydroxide were added
  8. temperaturethe reaction mixture was then refluxed for 1 hour
  9. concentrationThe medium was concentrated under reduced pressure
  10. dissolutionThe residue was dissolved in water
  11. extractionextracted twice with DCM
  12. dry with materialThe organic phase was dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. washThe residue was washed with petroleum ether
  16. filtrationfiltered on a Büchner funnel

Sources & evidence

ORD record
ord-bb1064eb59af499cb731c9669596a6a9
Source dataset
uspto-grants-2013_10
Patent number
US08546385B2

Reaction notes

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