Category: imidazoles-derivatives

33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 33543-78-1

the solution of 5.3 g of ethyl imidazole-2-carboxylate in 20 ml of anhydrous dimethylformamide is added dropwise over 30 minutes at a temperature close to 20° C. to a suspension of 2.43 g of 50percent sodium hydride in 60 ml of anhydrous dimethylformamide kept under a nitrogen atmosphere. After stirring for 15 minutes, a solution of 9.26 g of 2-bromo-4-fluoro-1-indanone in 25 ml of anhydrous dimethylformamide is added dropwise over 30 minutes at a temperature close to 20° C. The mixture is stirred for 18 hours, and then after slowly adding 30 ml of water, poured into 200 ml of distilled water and extracted four times with 100 ml of dichloromethane. The organic phases are pooled, washed with 600 ml of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 45° C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar) with ethyl acetate as eluent. 1.2 g of ethyl 1-(4-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 145° C.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 693-98-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 693-98-1 name is 2-Methyl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: In a typical experiment, imidazole (1.2 mmol), aryl halide (1.0 mmol), catalyst, and base (2.0 mmol) were added to a hydrothermal reactor (20 mL). The mixture was heated to the desired temperature with stirring. After the completion of the reaction and cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (3 × 15mL). The combined organic extracts were dried with anhydrous Na2SO4 and the obtained product was purified by column chromatography on silica gel using dichloromethane: methanol (100:1, v/v) as the eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Huang, Qiang; Zhou, Limei; Jiang, Xiaohui; Qi, Xiaolong; Wang, Zhonghua; Lang, Wencheng; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 11; (2014); p. 1818 – 1824;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5805-57-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of C-(1H-benzoimidazol-2-yl)-methylamine (200 mg, 1.0 mmol) and triethylamine (139 muL, 1 mmol) in CH2Cl2 (5 mL) (Boc)2O (420 mg, 2 mmol) is added, and the reaction mixture is stirred at r.t. for 1 h. After solvent evaporation, the crude product is purified by flash chromatography (1:1 EtOAc-Et.petr., Rf=0.5), to give 2-(tert-butoxycarbonylamino-methyl)-benzoimidazole-1-carboxylic acid t-butyl ester as a yellow oil (246 mg, 0.71 mmol) in 71.% yield. 1H NMR (CDCl3, 200 MHz) epsilon 7.96-7.91 (m, 1H), 7.72-7.67 (m, 1H), 7.35-7.26 (m, 2H), 5.85 (br, 1H), 4.80 (d, 2H), 1.71 (s, 9H), 1.48 (s, 9H) ppm. This intermediate (175 mg, 0.5 mmol) is dissolved in anhydrous THF (10 mL) and PPh3 (330 mg, 0.5 mmol) and 4-pentynol (46 muL, 0.5 mmol) are added. Then, after cooling to 0 C., DIAD (100 muL, 0.5 mmol) is slowly added, and after 15 min at 0 C., the mixture is heated under microwave irradiation at 110 C. for 1 h. Following flash chromatography purification (5:1 EtOAc-petr. et.), compound 10 is obtained in 64% yield. 1H NMR (CDCl3, 200 MHz) delta 7.95-7.90 (m, 1H), 7.71-7.67 (m, 1H), 7.34-7.26 (m, 2H), 5.79 (d, 2H), 2.30-2.20 (m, 2H), 2.03 (s, 1H), 1.95-1.92 (m, 2H), 1.80 (t, 2H), 1.71 (s, 9H), 1.47 (s, 9H) ppm.

The chemical industry reduces the impact on the environment during synthesis (1H-Benzo[d]imidazol-2-yl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITA’ DEGLI STUDI DI FIRENZE; Guarna, Antonio; Menchi, Gloria; Cini, Nicoletta; Trabocchi, Andrea; Pupi, Alberto; Bottoncetti, Anna; Raspanti, Silvia; Calorini, Lido; US2013/40964; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

PREPARATION 321H-imidazole-2-carboxylic acid21.75 mL (43.5 mmol) of a 2M solution of lithium hydroxide in water were added to a solution of 1.22 g (8.71 mmol) of ethyl 1H-imidazole-2-carboxylate (ref) in a mixture of tetrahydrofurane (20 mL) and water (20 mL).The reaction mixture was warmed up to reflux, and stirred for 1.5 hours.The reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum.The crude residue (3.0 g) was used in next step without further purification.LRMS (m/z): 113 (M+1)+.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; EP2518070; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(iii) (1-trityl-1H-imidazol-4-yl)methanol Trityl chloride (2.1 g) was added to a mixture of 4-hydroxymethyl imidazole hydrochloride (1.0 g) and triethylamine (3.1 ml) in DCM (25 ml) at RT. Further DCM (20 ml) was added and the mixture stirred for 18 h. The precipitate was filtered, washed with water and then ether to give the subtitle compound (2.0 g). 1H NMR DMSO-d6: delta 7.44-7.36 (9H, m), 7.29 (1H, s), 7.10-7.08 (6H, m), 6.72 (1H, s), 4.87 (1H, t), 4.33 (2H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Imidazolemethanol hydrochloride, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2008/293775; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 96797-15-8

Compound 1 (2.2 g, 5.0mmol), o-formylphenylboronic acid(1.2 g, 7.5mmol), K3PO4 (3.2 g, 15mmol), Pd (PPh3)4 (0.6 g, 1.0mmol) is dissolved in DMF/H20 (30mL/6mL). The system is replaced with nitrogen and warmed at 90C, the reaction is stirred overnight. The reaction solution is diluted with ethyl acetate (50mL), wash with saturated brine (25mL X 3), dry over anhydrous sodium sulfate, and dry under reduced pressure. Crude column chromatography (PE: EA = 5:1), and then obtained brown solid compound 2 (810 mg, 39%).

The synthetic route of 4-Iodo-1-trityl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zhang Guimin; Guan Yongxia; Li Xin; (15 pag.)CN107556315; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, These common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 15(6-{[4-(1-Butylcyclopropyl)benzyl](1-methyl-1H-imidazol-4-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetic acid (Exemplary compound No. 1138)15-(a): tert-Butyl [tert-butoxycarbonyl(6-{[4-(1-butylcyclopropyl)benzyl](1-methyl-1H-imidazol-4-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetateTo 6 ml of a methylene chloride solution containing 307 mg (0.586 mmol) of tert-butyl [tert-butoxycarbonyl(6-{[4-(1-butylcyclopropyl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate obtained in Reference example 13 were added uncer ice-cooling 163 mul (1.17 mmol) of triethylamine and 127 mg (0.703 mmol) of 1-methyl-1H-imidazol-4-ylsulfonyl chloride, and the mixture was stirred at the same temperature for 2.5 hours and at room temperature for 6 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=3:7?1:3 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 293 mg of the title compound as colorless oily product. (Yield: 75%)Mass Spectrum (CI, m/z): 668 (M++1).1H-NMR Spectrum (CDCl3, delta ppm): 7.65 (d, J=8.2 Hz, 1H), 7.46 (dd, J=8.2, 7.4 Hz, 1H), 7.38 (d, J=1.2 Hz, 1H), 7.18 (d, J=1.2 Hz, 1H), 7.15 (s, 4H), 6.96 (d, J=7.4 Hz, 1H), 4.58 (s, 2H), 4.50 (s, 2H), 4.38 (s, 2H), 3.67 (s, 3H), 1.55-1.47 (m, 2H), 1.52 (s, 9H), 1.43 (s, 9H), 1.26-1.15 (m, 4H), 0.83 (t, J=6.8 Hz, 3H), 0.74-0.68 (m, 2H), 0.66-0.59 (m, 2H).

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE INDUSTRIES, LTD.; US2012/259123; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 53484-18-7, name is 1-Methyl-1H-benzo[d]imidazole-6-carboxylic acid, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 53484-18-7, Computed Properties of C9H8N2O2

Oxalyl chloride (42 mu, 0.47 mmol, 1.7 eq) was added dropwise to a mixture of 1- methyl-lH-benzo[d]imidazole-6-carboxylic acid (50 mg, 0.28 mmol, 1.0 eq) and DMF (2 mu, 0.03 mmol, 0.1 eq) in DCM (0.8 mL). The reaction was stirred at rt for 2 hrs. The reaction was concentrated under reduced pressure to give crude l-methyl-lH-benzo[d]imidazole-6- carbonyl chloride as a yellow residue that was used without further purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Methyl-1H-benzo[d]imidazole-6-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENANTA PHARMACEUTICALS INC; GRANGER, Brett; WANG, Gouqiang; SHEN, Ruichao; MA, Jun; XING, Xuechao; HE, Jing; HE, Yong; LONG, Jiang; WANG, Bin; OR, Yat, Sun; (108 pag.)WO2018/218044; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 21252-69-7 as follows. Recommanded Product: 21252-69-7

General procedure: To a screw capped tube flask,chloroalkylated quaternary ammonium salt 2 and 5 equivalents of alkyl imidazole 3 were added with acetonitrile (5 ml). The sealed flask was heated at 100 for 24h. After the solvent was removed by evaporation, the residue was dissolved in a small amount of dichloromethane. The solution was poured into ethyl acetate, anoily imidazolium salt was separated from an organic phase. In case of 4ao, it was recrystallized in ethylacetate. Salt 4 was also moisture-sensitive as 2.

According to the analysis of related databases, 21252-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cho, Beom Shin; Jung, Il Gu; Chung, Young Keun; Han, Jin Wook; Bulletin of the Korean Chemical Society; vol. 36; 2; (2015); p. 451 – 452;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, A new synthetic method of this compound is introduced below., Formula: C10H8N2O

A mixture of 4-(1H-imidazol-1-yl)benzaldehyde (0.025mol) and thiosemicarbazide (0.025 mol) in ethanol (40 mL)was refluxed for 12 h. The reaction mixture was cooled andfiltered. The product was crystallized from ethanol.M.p. 250.1 C.IR numax (cm-1): 3352.28 (N-H stretching), 3113.11 (AromaticC-H stretching), 2981.95 (Aliphatic C-H stretching), 1633.71,1608.63, 1533.41, 1517.98, 1473.62 (C=N, C=C stretchingand N-H bending), 1359.82 (C-H bending), 1300.02,1236.37, 1180.44, 1089.78, 1060.85 (C-N, C=S stretchingand aromatic C-H in plane bending), 960.55, 939.33, 914.26,835.18, 812.03, 767.67, 632.65, 617.22 (Aromatic C-H outof plane bending).1H NMR (400 MHz, DMSO-d6) delta (ppm): 7.11 (s, 1H),7.69 (d, J= 8.8 Hz, 2H), 7.82 (s, 1H), 7.93 (d, J= 8.4 Hz,2H), 8.05 (s, 1H), 8.09 (s, 1H), 8.24 (s, 1H), 8.34 (s, 1H,CH=N), 11.49 (s, 1H).MS (ESI) (m/z): (M+H)+ 246Anal. Calcd for C11H11N5S: C, 53.86; H, 4.52; N, 28.55.Found: C, 53.85; H, 4.54; N, 28.52.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Ciftci, Guel?en Akalin; Altintop, Mehlika Dilek; Temel, Halide Edip; Oezdemir, Ahmet; Kaplancikli, Zafer Asim; Letters in drug design and discovery; vol. 14; 5; (2017); p. 554 – 566;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem