Hydrochloric Acid → HCID 178440798, Verbindung

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Reaktionsgleichung

C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:10]=[CH:9]2)C=CC=CC=1.Cl>C(O)C>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[N:10]=[CH:9]1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

1-[1-Triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne (0.30 gram, 0.64 mmol) was dissolved in ethanol (10 ml). 2N HCl (20 ml) was added, and the mixture heated at 90° C. for 1 hour. The reaction mixture was cooled, filtered, and the filtrate neutralized with 10% NAOH solution and then partitioned between chloroform and water. The chloroform layer was separated, dried over Na2SO4, filtered and evaporated in vacuo to obtain the crude oil. The crude product was purified using column chromatography using MeOH/CHCl3, 10:90 to afford 155 mgs of 1-[1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne (23). ##STR54## 4-(6-Cyclohexylhex-3-ynyl)imidazole (23) 1H-NMR (300 MHz, CDCl3): δ7.05 (s, 1H), 6.83 (s, 1H), 2.80 (m, 2H), 2.45 (m, 2H), 2.15 (m, 2H), 1.68 (m, 5H), 1.4-1.1 (m, 6H), 0.86 (m, 2H); Mass Spectrum: (DCl/NH3): 231 (M+1)+, MW=230.3434, C15H22N2. CHN Analysis: Calc.: C: 78.26, H: 9.56, N: 12.17; Found: C: 77.79, H: 9.51, N: 11.86.

Aufarbeitung

temperatureThe reaction mixture was cooled
filtrationfiltered
custompartitioned between chloroform and water
customThe chloroform layer was separated
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated in vacuo
customto obtain the crude oil
customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag: ord-3eba276ccca14acdbaeae2d625291ec3
Quelldatensatz: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06166060

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