Water → 1-(3-Cyclopentyl-propyl)-3-(4-nitro-phenyl)-1,3-dihydro-imidazol-2-one

HRID 1071166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071166
[CH:1]1([CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11](OC)OC)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1)([O-:18])=[O:17].FC(F)(F)C(O)=O.O>C(Cl)Cl>[CH:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH:10]=[CH:11][N:25]([C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=3)[C:26]2=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 187930233-Cyclopentyl-propyl (2,2-dimethoxy-ethyl)-amine

Produkt 1

HCID 224717321-(3-Cyclopentyl-propyl)-3-(4-nitro-phenyl)-1,3-dihydro-imidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The product from Example 48 (2.6 g, 12.1 mmol) was dissolved in CH2Cl2 (30 mL) and cooled to 0° C. 4-Nitrophenylisocyanate (1.98 g, 12.1 mmol) was added, and the mixture was allowed to warm to 23° C. The reaction was diluted with additional CH2Cl2 (30 mL) and cooled to 0° C. before a 1:1 solution of trifluoroacetic acid and water was added. The biphasic solution was vigorously stirred for 18 hours at ambient temperature. The layers were separated, and the aqueous layer was extracted with CHCl3. The combined organic layers were washed with saturated NaHCO3, brine, dried (MgSO4), and concentrated to a yellow solid. Mp 105-107° C. Rf=0.4 (2:1 hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.30 (d, 2H), 8.11 (d, 2H), 7.26 (d, 1H), 6.91 (d, 1H), 3.57 (t, 2H), 1.71 (m, 3H), 1.63 (m, 2H), 1.47 (m, 4H), 1.24 (m, 2H), 1.03 (m, 2H); MS (CI) m/z 316 (MH+).

Aufarbeitung

  1. temperatureto warm to 23° C
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CHCl3
  5. washThe combined organic layers were washed with saturated NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-74d6fcc8e0594cda80551e6173ffc366
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903218B2

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