* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
5.18 g (60.2 mmol) of 2-imidazolidone and 50 mL of acetic anhydride were added to a 100 mL recovery flask, and the mixture was stirred at an oil bath temperature of 150 ° C. for 1 hour. After cooling to room temperature, the precipitated solid was collected by filtration and washed with a small amount of cold ethanol to obtain 4.94 g (yield: 64.1percent) of colorless solid 1-acetyl-2-imidazolidone.
63%
for 0.5 h; Reflux
A solution of imidazolidin-2-one 1a (0.47 g, 5.3 mmol) inAc2O (4.5 mL) was refluxed for 30 min. The reaction mixture was allowed to cool down to roomtemperature, and a white precipitate was formed. The precipitate was collected by vacuumfiltration, and the filtrate was concentrated in vacuo. The combined solids obtained were purifiedby flash column chromatography (silicagel, AcOEt) to obtain 1b, as a white solid (0.43 g, 63percent)mp (EtOH) 180-181 C (Lit.41 177-178 C); IR (KBr): νmax 1654, 1725, 3259 cm-1; 1H NMR (300MHz) δ 2.47 (s, 3H), 3.47 (t, J 8.1 Hz, 2H), 3.92 (t, J 8.1 Hz, 2H), 5.87 (broad s, 1H); 13C NMR(75.5 MHz) δ 23.3, 36.4, 42.1, 157.2, 170.8; MS (CI, 230 eV) m/z (percent) 129 [MH+], 128 [M+], 85(100), 70 (10).
Reference：
[1] Chemistry - A European Journal, 2002, vol. 8, # 11, p. 2464 - 2475
[2] Patent: JP2016/145198, 2016, A, . Location in patent: Paragraph 0087-0089
[3] Arkivoc, 2014, vol. 2014, # 2, p. 44 - 56
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 6409,6412
2
[ 65118-65-2 ]
[ 75-36-5 ]
[ 5391-39-9 ]
Reference：
[1] Patent: US3972869, 1976, A,
[2] Patent: US3972870, 1976, A,
[3] Patent: US3983105, 1976, A,
[4] Patent: US3974141, 1976, A,
[5] Patent: US3974142, 1976, A,
[6] Patent: US3978056, 1976, A,
Stage #1: at 60 - 65℃; for 36 h; Stage #2: for 4 h; Reflux Stage #3: With hydrogenchloride In ethanol at 20℃; for 1 h;
Weigh 18.6 g of 4-amino-5-chloro-2,1,3-benzothiadiazole and 15.4 g 1-Acetyl imidazolin-2-one, added to 120 mL of phosphorus oxychloride,Warm up to 60-65°C for 36 hours.The solvent is distilled off under reduced pressureAdd 160 mL of methanol to the resulting oil.The reaction was heated at reflux for 4 hours.Cold to room temperature,The reaction solution was poured into 160 mL of ice water.The aqueous sodium hydroxide solution adjusts the pH to 9-10.filter,dry.Trizanidol powdered solid 18g, yield 71percent.The resulting tizanidine is added to 100 mL of saturated hydrogen chloride ethanol solution,Stir for 1 hour at room temperature. Filtration, no filter cakeAfter washing with ethanol and drying, ethanol was recrystallized to obtain solid tizanidine hydrochloride 17.5g, the yield was 85.0percent, and the purity was 99.25percent.
Reference：
[1] Patent: CN107759582, 2018, A, . Location in patent: Paragraph 0049-0051
5-chloro-2-benzyl-3-(4,5-dihydroimidazol-2-yl)-1H-indole hydrochloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Step 3: A mixture of 2.42 g (10 mmol) 5-chloro-2-benzylindole and 1.28g (10 mmol) 1-acetyl-imidazolidine-2-one (0.1 mol) is added to phosphorus oxychloride (10 ml) and heated to 60 C. for 5 hours. After evaporation of phosphorus oxychloride the residue is treated with ethanol (14 ml) and heated to reflux for 3.5 hours. Ethanol is evaporated. The residue is purified by chromatography to obtain the hydrochloride. The base is obtainable by treatment with 2N sodium hydroxide to pH 11. The solid is filtered off and dried in vacuo. Hydrochloride, m.p. 299-300 C., M.S. (Ei 70 ev) m/Z M=309.
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