Ethanol → (2-Chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamino)-acetic acid ethyl ester

HRID 2250469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250469
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)=[CH:4][C:3]=1[NH2:19].[CH2:20]([OH:22])[CH3:21].C([CH2:25][C:26](OBr)=[O:27])C.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:20]([O:22][C:26](=[O:27])[CH2:25][NH:19][C:3]1[CH:4]=[C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)[CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:21]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 99956372-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamineHCID 23177133Bromo ethylacetate

Produkt 1

HCID 16222810(2-Chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamino)-acetic acid ethyl esterAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 10 mL microwave reaction flask reaction charged with a magnetic stir bar, was added 2-chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine (0.100 g, 0.320 mmol), anhydrous ethanol (1.3 mL), bromo ethylacetate (0.241 g, 1.44 mmol) and triethylamine (67 μL, 0.48 mmol). The suspension was reacted at 120° C., for 15 min in a microwave set at 70 watts. The resulting yellow suspension was diluted with ethyl acetate (50 mL) and the organic layer was then washed with H2O (2×15 mL), brine (10 mL), dried over MgSO4, and the solvent was removed by evaporation. The white solid was then purified by flash column chromatography (silica gel, elution with EtOAc:hexanes, 1:5) to yield 0.119 g (94%) of the title compound as a white solid. 1H NMR (CDCl3): 7.59 (dd, 1H, J=5.2 and 1.4 Hz), 7.47 (dd, 1H, J=8.3 and 1.7 Hz), 7.38 (dd, 1H, J=8.3 and 1.1 Hz), 7.27 (d, 1H, J=1.7 Hz), 7.10 (dd, 1H, J=5.2 and 1.4 Hz), 5.11 (t, 1H, J=5.0 Hz), 4.29 (q, 2H, J=7.1 Hz), 4.05 (d, 2H, J=5.2 Hz), 1.33 (t, 3H, J=7.1 Hz).

Aufarbeitung

  1. customTo a 10 mL microwave reaction flask reaction
  2. additioncharged with a magnetic stir bar
  3. customThe suspension was reacted at 120° C., for 15 min in a microwave
  4. washthe organic layer was then washed with H2O (2×15 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed by evaporation
  7. customThe white solid was then purified by flash column chromatography (silica gel, elution with EtOAc:hexanes, 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-deac228e14694970ae8235d4d3513bf9
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317029B2

Notizen zur Reaktion

Wird geladen…