Reaktion #1925225

Reaktionsgleichung

N-(3-triethoxysilylpropyl)-4,5-dihydroimidazol

1-chlorobutane

→

1-(butyl)-3-(3-triethoxysilylpropyl)-4,5-dihydroimidazolium chloride

Ausbeute 99.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Sonstigethe volatiles evaporated under reduced pressure (10−2 torr)
3. 3
   Waschenwas washed with pentane (3×100 ml)
4. 4
   TrocknenAfter drying the residue under reduced pressure (10−2 torr) a yellow solid of complex (2)
5. 5
   Sonstigewas obtained in 99% yield

Vorschrift

A mixture of N-(3-triethoxysilylpropyl)-4,5-dihydroimidazol (13.7 g, 0.05 mol) and 1-chlorobutane (13.9 g, 0.15 mol) were refluxed at 78° C. for 21 hrs. The reaction mixture was cooled to room temperature and the volatiles evaporated under reduced pressure (10−2 torr). The resulting material consisted of a brown colored paste, which was washed with pentane (3×100 ml). After drying the residue under reduced pressure (10−2 torr) a yellow solid of complex (2) was obtained in 99% yield. 1H NMR (CDCl3) 0.60 (m, 2H, 3J=7.0, CH2—CH2—Si), 0.96 (tr, 3H, 3J=7.4, —CH2—CH2—CH3), 1.22 (tr, 9H, 3J=7.0, CH3—CH2—O), 1.38 (six, 2H, 3J=7.4, —CH2—CH2—CH3), 1.68 (m, 2H, Si—CH2—CH2—), 1.76 (m, 2H, —CH2—CH2—CH3), 3.65 (m, 4H, Si—CH2—CH2—CH2—N and —N—CH2—CH2—N—Bu), 3.82 (qr, 6H, CH3—CH2—O), 4.04 (m, 4H, —N—CH2—CH2—CH2—CH3 and —N—CH2—CH2—N—Bu), 10.01 (s, 1H, N—CH—N) ppm; 13C NMR (CDCl3) 7.32 (1C, Si—CH2—CH2—), 13.58 (1C, —CH2—CH2—CH3), 18.33 (3C, CH3—CH2—O—), 19.63 (1C, —CH2—CH2—CH3), 21.27 (1C, Si—CH2—CH2—), 29.36 (1C, —CH2—CH2—CH3), 48.01, 48.21, 48.51, 50.37 (4C, —CH2—N—CH2—CH2—N—CH2—), 58.53 (3C, CH3—CH2—O—), 158.87 (1C, N—CH—N) ppm; MS/ES+ (m/e) 331 [M+], Anal. Calcd for C16H35N2ClO3Si: C, 52.37; H, 9.61; N, 7.63; Cl, 9.66; Si, 7.65. Found: C, 51.64; H, 9.94; N, 7.60; Cl, 13.61; Si, 7.65.

Quelle