Triethylamine → 4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamide

HRID 1181361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181361
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[NH2:6].C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1>C(Cl)Cl>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:31])=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 117365033-Methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

Produkt 1

HCID 589808694-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]aniline (43 mmol, 10.0 g) in DCM was added triethylamine (52 mmol, 5.2 g) and 4-chloro-2-nitrobenzoyl chloride (9.5 g, 43 mmol). The solution was stirred overnight. The reaction mixture was extracted with 2N HCl. The resulting acidic aqueous solution was made basic by adding 2N NaOH. The combined basic aqueous solution was extracted with DCM. The organic phase was washed with brine, dried and concentrated giving the title compound (11.5 g, 69%). 1H NMR (DMSO-D6): δ 1.66 (4H, m), 2.49 (4H, m), 2.75 (2H, t, J=6.0 Hz), 3.72 (3H, s), 4.00 (2H, t, J=6.0 Hz), 6.94 (1H, d, J=8.6 Hz), 7.14 (1H, d, J=8.6 Hz), 7.79 (1H, d, J=8.1 Hz), 7.94 (1H, d, J=8.1 Hz), 8.23 (1H, s), 10.55 (1H, s). LCMS m/z=420 (m+H+).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with 2N HCl
  2. additionby adding 2N NaOH
  3. extractionThe combined basic aqueous solution was extracted with DCM
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a822c74cca6540a7be14b399ff1e7a18
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285557B2

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