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CAS 1077-93-6
InChIKey
InChIKey=DUOHVNSMLSPTMI-UHFFFAOYSA-N
SMILES
C(CCO)N1C(N(=O)=O)=CN=C1C
Canonical SMILES
O=N(=O)C1=CN=C(N1CCCO)C

[mishka]

из 2-methyl-5-nitro-1H-imidazole и 1-chloro-3-hydroxypropane


With copper (I) iodide; toluene-4-sulfonic acid; sodium iodide at 165℃; for 3h; Temperature; Reagent/catalyst;


67%
Current Patent Assignee: WEIFANG FUBANG PHARMACEUTICAL - CN114605332, 2022, A
Location in patent: Paragraph 0022-0026

Experimental Procedure
1-3 Example 3
Reaction with sodium iodide and cuprous iodide as catalysts and pH reduction with p-toluenesulfonic acidCombine 12.7 g 2-methyl-5-nitroimidazole (0.1 mol), 50 g 3-chloropropanol (0.52 mol), 3 g p-toluenesulfonic acid, 1 g cuprous iodide (0.005 mol) and 3 g Sodium iodide (0.02 mol) was heated to 165°C, then refluxed at 165°C for 3 hours to obtain a reaction mixture, then most of the excess 3-chloropropanol in the reaction mixture was distilled off under reduced pressure, and the residue was taken up with 20 ml of water Stir, then filter, the filtrate is adjusted to pH 9 with saturated aqueous sodium bicarbonate solution, and then extracted with ethyl acetate twice, 100 ml each time, the organic layers are combined, dried over anhydrous sodium sulfate, and concentrated to obtain the isomeric ternidazole. 1.3 g of body, the aqueous layer was continuously extracted three times with 100 ml of ethyl acetate each time, the organic layers were combined, dried and concentrated to 50 ml, a small amount of solid was precipitated (0.5 g), filtered, and the mother liquor was left overnight. Nitazole is 12.5 g, the yield is 67%, and the purity is 99.3%.






In lithium hydroxide monohydrate


Current Patent Assignee: SUTTER WEST BAY HOSPITALS - US6423707, 2002, B1

Experimental Procedure
A.1 1.
1. Synthesis of 1-(3-Hydroxypropyl)-2-methyl-5-nitro-1H-imidazole and its Ester The reaction mixture of 2-methyl-5-nitroimidazole (127 g, 1.0 mol) and 1-chloro-3-hydroxypropane (500 g, 5.3 mol) will be refluxed for 24 h. Then, the excessive amount of 1-chloro-3-hydroxypropane will be removed via evaporation under a condition of 2660 Pa. To the residue, 200 ml of water will be added. The mixture will be filtered. The filtrate will be collected. The filter residue will be then rinsed with water. The water phases will be combined and alkalified with saturated sodium bicarbonate aqueous solution up to pH 9. The solution will be placed in the cold room overnight for crystallization. The crystals will be filtered, washed with water, and then dried. The crude product will be recrystallized from ethyl acetate to give 1-(3-hydroxypropyl)-2-methyl-5-nitro-1H-imidazole.
======================
из 1,3-bis(2-methyl-5-nitro-1H-imidazol-1-yl)propane

In ethyl acetate


81 %
Current Patent Assignee: WEIFANG FUBANG PHARMACEUTICAL - CN115417820, 2022, A
Location in patent: Paragraph 0029-332

Experimental Procedure
1-2
After filtering out the reaction by-products, the remaining mother liquor was concentrated twice to obtain a second concentrate, and ethyl acetate (100 mL) was added to the second concentrate,Put it into the freezer of the refrigerator to crystallize, and filter to obtain 1.3 g of ternidazole, with a yield of 70% and a purity of 99%.
==========================
1-(3-Hydroxy-propyl)-2-methyl-5-nitro-imidazol, Toluol-4-sulfonsaeure;
Current Patent Assignee: RHONE POULENC UNCLEAR - FRM3601, 1964, M[Chem.Abstr., 1966, vol. 64, # 8192]



Trimethylenoxym, 2-Methyl-5-nitro-imidazol in HCO2H;
Current Patent Assignee: RHONE POULENC UNCLEAR - FR1379787, 1963, A[Chem.Abstr., 1965, vol. 62, # 7768]


2-Methyl-4(5)-nitro-imidazol , 3-Chlorpropanol;
Cosar et al.
[Arzneimittel-Forschung/Drug Research, 1966, vol. 16, p. 23,25]


aus d.Komponenten;
Current Patent Assignee: RHONE POULENC UNCLEAR - FRM3342, 1965, M[Chem.Abstr., 1965, vol. 63, # 11571c]

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