p-Anisoyl chloride → N-(2-Amino-5-bromo-phenyl)-4-methoxy-benzamide

HRID 252823

反応式

HRID 252823 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([NH2:8])[CH:7]=1.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.O.O.Cl[Sn]Cl>C1COCC1>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[NH:8][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 7477p-Anisoyl chlorideHCID 61436Stannous chloride dihydrateHCID 53147665-Bromo-2-nitroaniline

生成物 1

HCID 59736778N-(2-Amino-5-bromo-phenyl)-4-methoxy-benzamide収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

In aflame dried, round bottom flask, 5-bromo-2-nitro-aniline (2) (10.66 g, 49.09 mmol), (scheme 1, Example 1), and 4-methoxybenzoyl chloride (8.37 g, 49.09 mmol) were added. The mixture was heated to 90° C. The melted solids were stirred overnight to give a yellow-brown solid. THF (250 mL) was then added and the solution was treated with SnCl2.2H2O (55.38 g, 245.45 mmol, 5.0 eq) and stirred at room temperature for 2 hrs. Approx. half of the THF was evaporated then 200 mL of EtOAc and 100 mL sat. NaHCO3 were added. The precipitated tin salt was taken out by filtration and a work-up was done on the filtrate with EtOAc. The combined organic layers were washed with water and brine and dried over MgSO4. Most of the EtOAc was evaporated then hexane was added and the precipitate was collected by filtration to give the title compound 114 as a beige powder (13.40 g, 85% yield). 1H NMR (DMSO-d6) δ(ppm): 9.52 (s, 1H), 7.93 (d, J=9.0 Hz, 2H), 7.34 (d, J=2.3 Hz, 1H), 7.08 (dd. J=8.6, 2.3 Hz, 1H), 7.02 (d, J=9.0 Hz, 2H), 6.71 (d, J=8.6 Hz, 1H) 5.10 (s, 2H), 3.82 (s, 3H).

後処理

  1. customto give a yellow-brown solid
  2. stirringstirred at room temperature for 2 hrs
  3. customApprox. half of the THF was evaporated
  4. addition200 mL of EtOAc and 100 mL sat. NaHCO3 were added
  5. filtrationThe precipitated tin salt was taken out by filtration
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over MgSO4
  8. customMost of the EtOAc was evaporated
  9. additionhexane was added
  10. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-3599de0a3f5041768cb7f49e8f53149f
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

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