Beruflich Dokumente
Kultur Dokumente
A mixture of 4-methylquinoline (25.0 ml, 189 mmol, 1.0 equiv.) and iodomethane (25.0
ml, 402 mmol, 2.1 equiv.) in 1,4-dioxane (375 ml) was heated at reflux for 1 hr. On cooling to
ambient temperature the precipitate was collected by filtration and was washed with diethyl ether
(3 30 ml), hexanes (3 30 ml) and dried in vacuo to afford the title compound (51.3 g, 95%) as
a yellow solid. 1H NMR (400 MHz, DMSO-d6) 3.01 (s, 3H), 4.58 (s, 3H), 7.91 8.14 (m, 2H),
8.16 8.35 (m, 1H), 8.49 (d, J = 8.9 Hz, 1H), 8.54 (d, J = 8.5 Hz, 1H), 9.36 (d, J = 6.0 Hz, 1H).
A mixture of 1,4-methylquinolinium iodide (40.0 g, 140 mmol, 1.0 equiv.) and N,Ndiphenylformamidine (55.1 g, 281 mmol, 2.0 equiv.) in ethanol (225 ml) was heated at reflux for
1 hr. On cooling to room temperature the precipitate was collected by filtration and was washed
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with ethanol (3 70 ml) and then dried in vacuo to afford the title compound (29.3 g, 54%) as a
dark red/brown solid. This material was used in the next step without further purification.
4-[(E)-2-(Acetylphenylamino)ethenyl]-1-methylquinolinium iodide (6)
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TO3-Acetate (6)
Triethylamine (2.20 ml, 15.8 mmol, 0.5 equiv.) was added to a stirred solution of 2-(2methylbenzo[d]thiazol-3-ium-3-yl)acetate (11.5 g, 34.9 mmol, 1.0 equiv.) and 4-[(E)-2(acetylphenylamino)ethenyl]-1-methylquinolinium iodide (15.0 g, 34.9 mmol, 1.0 equiv.) in
dichloromethane (200 ml). After 14 hrs the reaction mixture was concentrated in vacuo and the
resultant residue was suspended in dichloromethane (800 ml). The precipitate was collected by
filtration and was washed with acetone (3 80 ml) and then dried in vacuo to afford the title
compound (7.7 g, 59%) as a dark blue solid. Exact mass calculated for [M+H+, C22H19N2O2S2+]
requires m/z 375.1162. Found 375.1156. HPLC: tR = 19.4 min.
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TO3-Biotin
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