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Diisopropylethylamine → 5-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-[1,2,4]oxadiazole

HRID 732082
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 732082
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([CH3:11])[C:9](=O)[CH2:8][N:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1.CCN(C(C)C)C(C)C.Cl[CH2:45][C:46]1[N:50]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([Cl:57])[CH:52]=2)[O:48][N:47]=1>O1CCOCC1.C(OCC)(=O)C>[Cl:57][C:53]1[CH:52]=[C:51]([C:49]2[O:48][N:47]=[C:46]([CH2:45][S:22][C:9]3[N:10]([CH3:11])[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[N:7][CH:8]=3)[N:50]=2)[CH:56]=[CH:55][CH:54]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 87949Lawesson's reagentHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 670708452-Furan-2-yl-3-methyl-3,5-dihydro-imidazol-4-one

Produkt 1

HCID 670709295-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-[1,2,4]oxadiazoleAusbeute 11,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Furan-2-yl-3-methyl-3,5-dihydro-imidazol-4-one (described in Takeuchi, H., Hagiwara, S., Eguchi, S., Tetrahedron (1989) 6375-6386) (50 mg, 0.30 mmol) was dissolved in dioxane (3 ml) and Lawesson reagent (136 mg, 0.34 mmol) was added. The reaction mixture was heated to reflux over night and then allowed to room temperature at which time DIPEA (212 ml, 1.22 mmol) and 3-chloromethyl-5-(3-chloro-phenyl)-[1,2,4]oxadiazole (140 mg, 0.61 mmol) was added. The resulting mixture was heated to reflux for 5 h and then kept at room temperature over night. Ethyl acetate was added and the reaction mixture was washed with water followed by brine. The organic phase was dried over MgSO4 and evaporated. The title compound (13 mg, 11%) was obtained by flash chromatography using 1% methanol in chloroform. 1H NMR (CD3OD) d (ppm): 7.96 (m, 1 H), 7.90 (m, 1H), 7.60 (dd, 1H), 7.57 (ddd, 1H), 7.46 (t, 1H), 7.09 (s, 1H), 6.86 (dd, 1H), 6.52 (dd, 1H), 3.95 (s, 2H), 3.74 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux over night
  3. additionwas added
  4. temperatureThe resulting mixture was heated
  5. temperatureto reflux for 5 h
  6. waitkept at room temperature over night
  7. washthe reaction mixture was washed with water
  8. dry with materialThe organic phase was dried over MgSO4
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-09adfff7319d4eb6b352a4ce549e69f7
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07585881B2

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