ChemicalBook CAS DataBase List 2-Chloro-4-nitroimidazole

2-Chloro-4-nitroimidazole synthesis

5synthesis methods

Product Name:2-Chloro-4-nitroimidazole
CAS Number:57531-37-0
Molecular formula:C3H2ClN3O2
Molecular Weight:147.52

683276-67-7

57531-37-0

Example 9 Preparation of 2-chloro-4-nitroimidazole: 2-chloro-5-iodo-4-nitroimidazole (273 mg, 1.0 mmol) was dissolved in anhydrous ethanol (5 mL), followed by sequential addition of triethylamine (420 μL, 3.0 mmol) and 10% palladium-carbon catalyst (27 mg) to the solution. The reaction mixture was hydrogenated by stirring for 3 hours at room temperature and under an atmosphere of hydrogen at atmospheric pressure. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford the colorless solid product 2-chloro-4-nitroimidazole (124 mg, 84.1% yield). The product was characterized by 1H-NMR (DMSO-d6): δ 8.44 (1H, s), 14.19 (1H, bs). Example 11 Preparation of 2-chloro-4-nitroimidazole: 2-chloro-5-iodo-4-nitroimidazole (545 mg, 2.0 mmol) was dissolved in anhydrous ethanol (10 mL), followed by sequential addition of triethylamine (840 μL, 6.0 mmol) and 10% palladium-carbon catalyst (54 mg) to the solution. The reaction mixture was hydrogenated under hydrogen pressure of 4 kg/cm2 in a pearl reduction apparatus. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give the colorless solid product 2-chloro-4-nitroimidazole (246 mg, 83.4% yield). The product was characterized by 1H-NMR (DMSO-d6): δ 8.44 (1H, s), 14.19 (1H, bs).

16265-04-6 Synthesis

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Yield:57531-37-0 87.3%

Reaction Conditions:

Stage #1:2-chloro-1H-imidazole with sulfuric acid at 20; for 0.5 h;
Stage #2: with sulfuric acid;nitric acid at 45 - 110; for 1 h;

Steps:

1
4 g of 98% sulfuric acid, 2.04 g of 2-chloroimidazole ((? 02 mol) was added to the three-necked flask, and the mixture was stirred at room temperature (? 5h,And then heated to 45 ~ 55 ° C, slowly dropping from 1. 9g95% fuming nitric acid (0. 03mol) and 5g 20% fuming sulfuric acid composition of the mixed acid, after dropping, the temperature to 110 ° C reaction lh, the end After the reaction solution was poured into ice water, the pH was adjusted to 3 to 4 with aqueous ammonia, filtered and the cake was dried to give a white powdery solid 2-chloro-4-nitroimidazole, 56 mg, yield 87.3% HPLC purity 99. 4%, melting point 218. 6 ~ 219.5 ° C.

References:

Yancheng Institute Of Technology;Zhao, LingLing;Dai, Yong;Qi, gang CN103396369, 2016, B Location in patent:Paragraph 0020; 0023

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References