4-Bromo-2-fluoroaniline → N-(4-bromo-2-fluorophenyl)-N-(6-trifluoromethoxy-1,3-benzothiazol-2-yl)amine

HRID 907724

반응식

HRID 907724 반응식
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([F:24])[CH:18]=1>C(O)CCC.O1CCOCC1>[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[C:19]([F:24])[CH:18]=1

참가 물질

5

반응물 2

HCID 1230504-Bromo-2-fluoroanilineHCID 100379242-Chloro-6-(trifluoromethoxy)-1,3-benzothiazole

생성물 1

HCID 21985778N-(4-bromo-2-fluorophenyl)-N-(6-trifluoromethoxy-1,3-benzothiazol-2-yl)amine수율 58.1%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

In a 250-mL round-bottom flask, 2-chloro-6-trifluoromethoxy-1,3-benzothiazole (5.36 g, 21.14 mmol) and 4-bromo-2-fluoroaniline (4.82 g, 25.36 mmol) were combined in 100 mL n-butanol containing 1% 4.0 M HCl in dioxane, and heated at 90° C. overnight. The mixture was cooled to rt and the solvent was removed under reduced pressure. Ethyl acetate (50 mL) was added, and the mixture was ultrasonicated by suspending the flask in an ultrasonication bath for 30 minutes. The mixture was filtered, and the filtrate was concentrated under reduced pressure. Acetonitrile (50 mL) was added to the mixture, which was then ultrasonicated for 30 minutes and then filtered to provide the product as a white solid (5 g, 58%). LC-MS m/z 409.1 (MH+), ret. time 4.02 min.

후처리

  1. temperatureThe mixture was cooled to rt
  2. customthe solvent was removed under reduced pressure
  3. additionEthyl acetate (50 mL) was added
  4. customthe mixture was ultrasonicated
  5. customfor 30 minutes
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionAcetonitrile (50 mL) was added to the mixture, which
  9. customwas then ultrasonicated for 30 minutes
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-ded41b34f3ca41bbba251b8c3e706c5f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013166B2

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