Hydrochloric Acid → N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine

HRID 30900

反応式

HRID 30900 の反応式
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[N:6]=1.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1.Cl>CCCCO>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=3[N:6]=2)=[C:15]([F:20])[CH:14]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 1230504-Bromo-2-fluoroanilineHCID 20498602-Chloro-4-methylbenzothiazole

生成物 1

HCID 23549342N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine収率 89.4%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2-chloro-4-methyl-1,3-benzothiazole (0.25 g, 1.36 mmol) in n-BuOH (8 mL was added 4-bromo-2-fluoroaniline (0.52 g, 2.72 mmol) and HCl (4.0 M in dioxane, 0.5 mL). The reaction was heated at 90° C. overnight. Solvent was removed by rotary evaporation and 1 N aqueous HCl was added. The aqueous layer was separated and extracted with EtOAc. The combined organic phases were washed with 1 N aqueous HCl and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was brought up in MeOH and the precipitate was collected by filtration, washed with MeOH, and dried in a vacuum oven to give N-(4-bromo-2-fluorophenyl)-4methyl-1,3-benzothiazol-2-amine (0.41 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ 2.62 (s, 3H), 7.07 (t, 1H), 7.15 (d, 1H), 7.36 (m, 2H), 7.51 (d, 1H), 8.72 (t, 1H).

後処理

  1. customSolvent was removed by rotary evaporation and 1 N aqueous HCl
  2. additionwas added
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. washThe combined organic phases were washed with 1 N aqueous HCl and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with MeOH
  11. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-e9c8bbd57b9f4ea3a1fdab40f2315ebb
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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