Sodium Tetrafluoroborate → HCID 178448617, compound

The complex 1-(butyl)-3-(3-triethoxysilylpropyl)-4,5-dihydroimidazolium chloride (2) (10 g, 28.0 mmol) was dissolved in acetonitrile (200 ml) and treated with one equivalent of sodium tetrafluoroborate (3.1 g, 28.0 mmol). The resulting slurry was stirred for 5 days at room temperature. After the removal of the precipitate by filtration the volatiles were evaporated under reduced pressure (10−2 torr) to give a brown liquid of complex (3) in 99% yield. 1H NMR (CD3CN) 0.50 (m, 2H, 3J=7.0, CH2—CH2—Si), 0.86 (tr, 3H, 3J=7.4, —CH2—CH2—CH3), 1.11 (tr, 9H, 3J=7.0, CH3—CH2—O), 1.26 (six, 2H, 3J=7.4, —CH2—CH2—CH3), 1.54 (m, 2H, Si—CH2—CH2—), 1.62 (m, 2H, —CH2—CH2—CH3), 3.38 (m, 4H, Si—CH2—CH2—CH2—N and —N—CH2—CH2—N—Bu), 3.72 (qr, 6H, CH3—CH2—O), 4.84 (m, 4H, —N—CH2—CH2—CH2—CH3 and —N—CH2—CH2—N—Bu), 8.20 (s, 1H, N—CH—N) ppm; 13C NMR (CD3CN) 8.47 (1C, Si—CH2—CH2—)−, 14.81 (1C, —CH2—CH2—CH3), 19.53 (3C, CH3—CH2—O—), 20.98 (1C, —CH2—CH2—CH3), 22.44 (1C, Si—CH2—CH2—), 30.54 (1C, —CH2—CH2—CH3), 49.09, 49.73, 49.89, 51.58 (4C, —CH2—N—CH2—CH2—N—CH2—), 59.90 (3C, CH3—CH2—O—), 159.09 (1C, N—CH—N) ppm; FT-IR (KBr) 3087 w, 2973 s, 2929 s, 2880 s, 1658 s, 1524 m, 1449 m, 1388 s, 1303 m, 1255 m, 1080 br, 957 m, 787 s cm−1; MS/ES+ (m/e) 331 [M+]. Anal. Calcd. for C16H35N2BF4O3Si: C, 45.94; H, 8.43; N, 6.70; B, 2.58; F, 18.16. Found: C, 45.95; H, 8.52; N, 7.34; B, 2.24; F, 17.86.

1. customAfter the removal of the precipitate
2. filtrationby filtration the volatiles
3. customwere evaporated under reduced pressure (10−2 torr)

ORD record

ord-7c08782c3a664e84bf24a333394f064e

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06673737B2