4-Butylphenyl isocyanate → Ethyl 3-{3'-[3-(4-butylphenyl)-1-methylureido]biphenyl-4-yl}propanoate

HRID 250839

Reaktionsgleichung

Reaktionsgleichung von HRID 250839
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[O:13])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:14][NH:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:13])[N:15]([C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)[CH3:14])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

3

Edukt 2

HCID 27963134-Butylphenyl isocyanateHCID 67271940Ethyl 3-(3'-methylaminobiphenyl-4-yl)propanoate

Produkt 1

HCID 67272240Ethyl 3-{3'-[3-(4-butylphenyl)-1-methylureido]biphenyl-4-yl}propanoateAusbeute 96,4 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

345 mg (1.5 mmol, 1.5 eq) of 1-butyl-4-isocyanatobenzene are added to 283 mg (1.0 mmol, 1 eq) of ethyl 3-(3′-methylaminobiphenyl-4-yl)propanoate (prepared in Example 7c). The reaction mixture is heated at 100° C. by microwave for 30 minutes. The mixture is chromatographed on silica gel (15 g FlashSmart column) eluted with 80/20 heptane/ethyl acetate. 442 mg of ethyl 3-{3′-[3-(4-butylphenyl)-1-methylureido]biphenyl-4-yl}propanoate are obtained in the form of a yellow oil that crystallizes. Yield=96%

Aufarbeitung

  1. customThe mixture is chromatographed on silica gel (15 g FlashSmart column)
  2. washeluted with 80/20 heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-95696888d2934723bb1606af10b17b30
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863332B2

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