Methylamine → 4-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzene

HRID 898948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898948
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(O)=[O:2].O=S(Cl)Cl.[CH3:26][NH2:27].[OH-].[Na+]>C(Cl)Cl>[CH3:26][NH:27][C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:2]

Komponenten

6

Edukt 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 230230632-Methoxy-5-(4-nitrophenoxy)benzoic acid

Produkt 1

HCID 206091394-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzeneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(3-carboxy-4-methoxyphenoxy)-1-nitrobenzene (0.50 g, 1.75 mmol) in CH2Cl2 (12 mL) was added SOCl2 (0.64 mL, 8.77 mmol) in portions. The resulting solution was heated at the reflux temp. for 18 h, cooled to room temp., and concentrated under reduced pressure. The resulting yellow solids were dissolved in CH2Cl2 (3 mL) then the resulting solution was treated with a methylamine solution (2.0 M in THF, 3.5 mL, 7.02 mmol) in portions (CAUTION: gas evolution), and stirred at room temp. for 4 h. The resulting mixture was treated with a 1N NaOH solution, then extracted with CH2Cl2 (25 mL). The organic layer was dried (Na2SO4) and concentrated) under reduced pressure to give 4-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzene as a yellow solid (0.50 g, 95%).

Aufarbeitung

  1. temperatureThe resulting solution was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting yellow solids were dissolved in CH2Cl2 (3 mL)
  5. extractionextracted with CH2Cl2 (25 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated) under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9c905e2a9a41401a82f108db32da6e45
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351834B1

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