Month: September 2021

Synthetic Route of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

General procedure: In a 100 mL round bottom flask, Cu-grafted catalyst (0.05 g), aryl-boronic acid (1 mmol), N-H heterocycles (1.2 mmol), and 10 mLmethanol were stirred under nitrogen atmosphere, at 40C. Thereaction mixtures were collected at different time interval and identified by GC-MS and quantified by GC analysis. After the com-pletion of the reaction, the catalyst was filtered off and washedwith water followed by acetone and dried in oven. The filtrate wasextracted with ethyl acetate (3 × 20 mL) and the combined organiclayers were dried with anhydrous Na2SO4by vacuum. The filtratewas concentrated by vacuum and the resulting residue was puri-fied by column chromatography on silica gel to provide the desiredproduct.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole, its application will become more common.

Reference:
Article; Islam, Sk.Manirul; Salam, Noor; Mondal, Paramita; Roy, Anupam Singha; Ghosh, Kajari; Tuhina; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 7 – 19;,
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. 162356-38-9, name is 2-(2-Bromophenyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Bromophenyl)-1H-imidazole

Step K 1-(4-Toluenesulfonyl)-2-(2-bromophenyl) imidazole A solution of 2.50 g (11.6 mmol) of 2-(2-bromophenyl)imidazole in 10 mL of methylene chloride was treated with 1.9 mL of triethylamine (13.8 mmol), 2.64 g (13.8 mmol) of p-toluenesulfonyl chloride and 100 mg of 4-dimethylaminopyridine. The reaction mixture was stirred at room temperature for 15 minutes then transferred to a separatory funnel and washed with water, 5percent aqueous citric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic layer was removed, dried over magnesium sulfate, filtered and solvents removed under vacuum. The crude product was chromatographed on silica, eluding with hexane/ethyl acetate (1:1), to give 4.16 g (11.0 mmol 95percent) of the product which was recrystallized from hexane. FAB-MS: calculated for C16 H13 BrN2 O2 S 376,378; found 377,379 (M+H, 50percent). 1 H NMR (200 MHz, CDCl3): 2.32 (s, 3H), 7.09 (d, 2 Hz, 1H), 7.12 (d, 8 Hz, 2H), 7.28 (m, 5H), 7.46 (m, 1H), 7.57 (d, 2 Hz, 1H).

The synthetic route of 162356-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5583130; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 95470-42-1, 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. 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

(1) Ethyl 2-bromo-4-methyl-1 H-imidazole-5-carboxylate (2.75 g, 11.81 mmol) described in Example 1(1) was dissolved in DMF (20 mE), potassium carbonate (3.26 g, 23.62 mmol) and 2,5-dichlorobenzyl bromide (3.4 g, 14.17 mmol) were added thereto, and the mixture was stirred at 90° C. for 3 hours. Afier the reaction, water (50 mE) was added and the mixture was extracted twice with ethyl acetate (50 mE). The organic layer was washed with saturated aqueous sodium chloride and subsequently dried over sodium sulfate. After concentrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-1 -(2,5- dichlorobenzyl)-4 -methyl-i H-imidazole-5-carboxylate(1.72 g):10160] ?H-NMR (CDC13) oe: 7.34 (1H, d, J=8.8 Hz), 7.20(1H, dd, J=8.8, 2.4 Hz), 6.40 (1H, d, J=2.4 Hz), 5.60 (2H, s),4.25 (2H, q, J=7.2 Hz), 2.56 (3H, s), 1.27 (3H, t, J=7.1 Hz);10161] ESI-MS mlz=391 (M+H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., name: (1-Methyl-1H-imidazol-2-yl)methanamine

Method B. A solution of 8 (0.247 g, 1.17 mmol) in MeOH (20 mL) was treated sequentially with 2-aminomethyl-1-methylimidazole (0.059 g, 0.53 mmol) and NaBH3CN (0.07 g, 1 mmol). The reaction mixture was stirred at room temperature overnight and the solvent was removed under vacuum yielding L2 a yellow oil. The crude product was purified as described in method A with similar isolated yields. IR (KBr) 3052 cm-1 (amide-NH), 1667 cm-1 (amide-C=O); 1H NMR CD2Cl2 delta 7.81 (s, AmIm(N-H)), 7.09 (s, 2, AmIm(H-5)), 6.80 (s, 1, Im(H-5)), 6.75 (s, 1, Im(H-4)), 3.60 (s, 2, Im(-CH2)), 3.57 (s, 4, AmIm(CH2)), 3.07 (s, 3, Im(-CH3)), 3.02 (s, 6, AmIm(-CH3)), 1.18 (s, 18, AmIm(-C(CH3)3)). 13C NMR delta 174.1, 169.7 (s, AmIm(-C=O)), 145.4 (s,Im(C2)), 141.2 (s, AmIm(C2)), 135.5 (s, AmIm(C4)), 126.4 (s,Im(C5)), 120.8 (s, Im(C4)), 107.9 (s, AmIm(C-5)), 47.8 (s, Im(-CH2-), AmIm(-CH2-)), 38.0 (s, AmIm(C(CH3)3), 31.1 (s, Im(CH3)), 28.9 (s, AmIm(C(CH3)3); HRMS calcd for C25H40N9O2, 498.3305 [M+H+], found 498.3311.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 124312-73-8.

Reference:
Article; Cheruzel, Lionel E.; Cui, Jinlan; Mashuta, Mark S.; Grapperhaus, Craig A.; Buchanan, Robert M.; Tetrahedron Letters; vol. 52; 37; (2011); p. 4771 – 4774;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 68282-47-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

COMPOUND 12.1.58: N,N-DIETHYL-4-{5,6,7-TRIMETHOXY-2-[(2-PHENYL- 1H-IMIDAZOL-5-YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1- YLIBENZAMIDE; 2-Phenyl-imidazole-4-carboxyaldehyde (92.6 mg, 0.54 mmol) was added to a solution of INTERMEDIATE 5.1. 16 (107.7 mg, 0.27 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (400 mg, 1.89 mmol) was added followed by N-methyl-2- pyrrolidinone (350 pL) and the reaction mixture stirred at RT for 16 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on SiOx column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 58 as an oil (33 mg, 22%). lH NMR (500 MHz, CDC13) : 8 1.10 (br s, 3H), 1.24 (br s, 3H), 2.63 (m, 1H), 2.76 (m, 2H), 3. 10 (m, 1H), 3.26 (br s, 2H), 3.57 (s, 3H), 3.51-3. 62 (m, 4H), 3.84 (s, 3H), 3. 88 (s, 3H), 4.65 (s, 1H), 5.98 (s, 1H), 6.91 (s, 1H), 7.25-7. 35 (m, 7H), 7.87 (d, J 8.5 Hz, 2H) ; 13C NMR (125 MHz, CDCl3) : 6 13.12, 14.45, 22. 51, 39.70, 43.67, 46.18, 49.68, 56.09, 60.70, 61.03, 66. 58, 107.94, 121.56, 125.43, 126.50, 128.46, 128.90, 129.91, 130. 76, 132. 78,136. 08,140. 72,144. 76, 146.76, 147.07, 150. 89, 151. 73, 171.64 ; (+) LRESIMS m/z 555.25 [M+H]+.

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, 2-Phenyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 492-98-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 492-98-8, name is 1H,1’H-2,2′-Biimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 16: Synthesis of (tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(ppy)2BIm]2) [0307] [0308] Under argon atmosphere, into a 100 mL Schlenk flask equipped with a stirrer were placed 322 mg (0.30 mmol) of di-mu-chloro-tetrakis(2-phenylpyridinato) diiridium(III), 40 mg (0.30 mmol) of 2,2′-biimidazole and 60 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 13 hours. Subsequently, 83 mg (0.63 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 24 hours. After the completion of the reaction, tetrahydrofuran was distilled off under reduced pressure, and then methylene chloride was added to the residue, and the insoluble substance was removed by filtration. The filtrate was concentrated under reduced pressure. The resultant crude reaction product was subjected to column chromatography with alumina (developing solvent: methylene chloride / hexane (volume ratio; 3/1) : 0.5 % triethylamine) for purification, to provide 113 mg of the desired compound as a yellow solid. (Yield: 33 %) The desired compound obtained was a mixture of isomers, and the product ratio was Isomer 1 (main product) : Isomer 2 = 61:39. [0309] Additionally, tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III) was a novel compound, which had the following properties: [0310] 1H-NMR (400MHz, C4D8O, delta (ppm)) Isomer 1; 8.18 (dd, 4H), 7.86 (d, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.38 (dd, 4H), 6.11 (s, 4H) Isomer 2; 7.92 (d, 4H), 7.78 (dd, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.32 (dd, 4H), 6.13 (s, 4H) FD-MS (M/Z): 1132 M+

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, 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 38993-84-9, Formula: C5H8N2O

A mixture of 4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine (100 mg, 0.33 mmol), 1-methyl-1H-imidazol-5-yl)methanol (73 mg, 0.65 mmol), diethyl azodicarboxylate (114 mg, 0.65 mmol) and triphenyl phosphine (171 mg, 0.65 mmol) in 1,4-dioxane (2 mL) was heated using microwave irradiation to 100° C. for 30 min. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC to provide Compound IIa (46 mg). 1H NMR delta (ppm) (CHCl3-d): 7.77-7.70 (4H, m), 7.56-7.46 (7H, m), 7.37 (1H, s), 5.97 (2H, s), 3.91 (3H, s). LCMS (10 cm_ESCI_Bicarb_MeCN) Rt 3.88 min; m/z 401 [M+H] 94.62percent purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1-Methyl-1H-imidazol-5-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BUeRLI, Roland Werner; ESMIEU, William Rameshchandra Krishna; LOCK, Christopher James; MALAGU, Karine Fabienne; OWENS, Andrew Pate; HARTE, William E.; US2014/121197; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

705-09-9, Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, 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 705-09-9.

Step 2: NaH (60%, l . lg, 45.8mmol, 1.5eq) was added protion-wise to a solution of compound Id (3.4g, 20.1mmol, l .leq) in DMF(50mL) at 0C and the mixture was stirred at r.t for 45min. Compound 5a (5.0g, 18.3mmol, leq) was added to the mixture. The mixture was stirred at r.t over weekend. Water was added and the mixture was extracted with ethyl acetate, the organic layer was washed with water for 3 times, dried, concentrated and purified by column chromatography to give 5b (3.4g, yield: 45.8%) as a white solid.’H NMR(CDC13, 300MHZ, ppm): delta 10.23(s, 1H), 7.72(d, 1H), 7.54(d, 1H)ES-MS m/z: 321(M+H+).

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TYROGENEX, INC.; LIANG, Congxin; WO2011/41399; (2011); A2;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 16681-59-7

Step 2 To a 500 mL round flask was added N-methyl-2-bromoimidazole (6.50 g, 40 mmol),2,4-diflurophenylboronic acid (7.89g, 50 mmol), palladium(II) acetate (0.28 g, 1.25 mmol), triphenylphosphine (1.31 g, 5 mmol), sodium carbonate (14.31 g, 135 mmol), and 200 mL of DME and 100 mL of water. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 12 hours. The mixture was extracted with ethyl acetate and further purified by a silica gel column. Distillation of the product at 150 C. gave N-methyl-2-(2,4-difluorophenyl)imidazole as a colorless oil (6.60 g, 85% yield), characterized by 1H-NMR and MS.

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:
Patent; Lin, Chun; Ma, Bin; Knowles, David B.; Brooks, Jason; Kwong, Raymond; US2006/8670; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 124750-92-1, 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 124750-92-1 as follows.

Step 3:; A solution of dicyclohexylcarbodiimide (DCC) (267.4 mg; 1.3 eq.) in anhydrous THF (10 ml) was added dropwise to a stirred solution of losartan acid (472 mg; 1.08 mmol) prepared as described in step 2, 5-(4-hydroxyphenyl)-3H-1,2-dithiol-3-thione (244.5 mg; 1.08 mmol) prepared as above described (step 1) and dimethylaminopyridine (DMAP, 7 mg) in 15 ml of tetrahydrofurane (THF). The reaction is performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction the dicyclohexylurea (DCC) is removed by filtration. The solution is evaporated to dryness and the crude product was purified by column chromatography (on silica gel) eluting with CH2C12-methanol (97:3) to give an orange solid with melting point 180-185 C.

According to the analysis of related databases, 124750-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTG Pharma S.r.l.; EP1980559; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem