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

HRID 252823

Reaktionsgleichung

Reaktionsgleichung von HRID 252823
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3599de0a3f5041768cb7f49e8f53149f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868205B2

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