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

HRID 1035325노트

반응식

HRID 1035325 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bb1064eb59af499cb731c9669596a6a9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546385B2

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