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

HRID 30901

反応式

HRID 30901 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-90ba5aab8e7741e6b17339b8382e4634
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

関連ノート

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