Propyl isocyanate → N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptyl-N'-propylurea

HRID 1109060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109060
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:32]([N:35]=[C:36]=[O:37])[CH2:33][CH3:34]>CCCCCC>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:36]([NH:35][CH2:32][CH2:33][CH3:34])=[O:37])[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 61033Propyl isocyanate2×HCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

Produkt 1

HCID 10436714N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptyl-N'-propylureaAusbeute 18,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (0.36 g, 0.0008 mol) in hexane (15 mL) was added propylisocyanate (0.094 mL, 0.085 g, 0.001 mol), and the reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was then treated with additional propylisocyanate (0.094 mL, 0.085 g, 0.001 mol) and stirred at ambient temperature overnight and then at reflux for 72 hours. The reaction mixture was concentrated under vacuum and the residue was chromatographed using 2:8 hexane-ethyl acetate. The resulting oil was triturated with hexane to give the title compound (0.8 g, 0.00015 mol) as a white solid, mp 78°-80°. 1H NMR (CDCl3) δ 7.6-7.2(m, 10H), 4.4(t,1H,J=7 Hz), 3.4-2.9 (m, 8H), I.9-1.1 (m, 19H), 1.0-0.75 (m, 6H).

Aufarbeitung

  1. stirringstirred at ambient temperature overnight
  2. temperatureat reflux for 72 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customthe residue was chromatographed
  5. customThe resulting oil was triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-9cecdf66479b48cba71885114db32231
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05318984

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