Butyl Chloride → HCID 178448616, compound

Temperature

78 °C

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.

1. temperatureThe reaction mixture was cooled to room temperature
2. customthe volatiles evaporated under reduced pressure (10−2 torr)
3. washwas washed with pentane (3×100 ml)
4. dry with materialAfter drying the residue under reduced pressure (10−2 torr) a yellow solid of complex (2)
5. customwas obtained in 99% yield

ORD record

ord-3c72e708e3764b5b8ef229fed296168d

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06673737B2