Dipropylamine → Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

HRID 348794

Reaktionsgleichung

Reaktionsgleichung von HRID 348794
C(C1NC=CN=1)(C1NC=CN=1)=O.[N+:13]([C:16]1[CH:17]=[C:18]([C:26]([O-:28])=O)[CH:19]=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22])([O-:15])=[O:14].[CH2:29]([NH:32][CH2:33][CH2:34][CH3:35])[CH2:30][CH3:31]>C1COCC1>[CH2:29]([N:32]([CH2:33][CH2:34][CH3:35])[C:26]([C:18]1[CH:19]=[C:20]([CH:25]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:28])[CH2:30][CH3:31]

Komponenten

5

Edukt 3

HCID 8902DipropylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 6931682Monomethyl-5-nitroisophthalate

Produkt 1

HCID 690570Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Carbonyl diimidazole (3.90 g, 24.0 mmol) is added to a mixture of mono-methyl 5-nitro-isophthalate (XXVIII, 4.50 g, 20.0 mmol) in dry THF (50 mL). The mixture is stirred for 0.5 hours. Dipropylamine (3.28 mL, 24.0 mmol) is added slowly to the mixture. The reaction mixture is then stirred for 4 hours. The solvent is removed under reduced pressure and the mixture is partitioned between ethyl acetate and water. The organic phase is separated and washed with saline, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (silica gel; ethyl acetate/hexanes, 15/85) gives the title compound, NMR (300 MHz, CDCl3) delta 8.88, 8.41, 8.35, 4.00, 3.48, 3.15, 1.72, 1.57, 1.00 and 0.77; MS (ESI+) for C15H20N2O5 m/z (M+H)+=309.2.

Aufarbeitung

  1. stirringThe reaction mixture is then stirred for 4 hours
  2. customThe solvent is removed under reduced pressure
  3. customthe mixture is partitioned between ethyl acetate and water
  4. customThe organic phase is separated
  5. washwashed with saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2c320c1b0ac14ca2b2414b9460eeea0c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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