Month: May 2021

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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Methyl-5-nitro-1H-benzo[d]imidazole

To a solution of 2-methyl-5-nitro-1H-benzimidazole (2) (9.0 g,0.05 mol) in ethanol (50 mL), K2CO3 (6.98 g, 0.075 mol) and benzylchloride (9.63 g, 0.075 mol) were refluxed for 8 h. After the completionof the reaction (monitored by TLC), the reaction mixturewas filtered and concentrated to give yellow solid. The residualmass was crystallized from ethanol to give mixture of 1-benzyl-2-methyl-5-nitro-1H-benzimidazole and 3-benzyl-2-methyl-5-nitro-3H-benzimidazole (3) in 75% yield. To a suspension of SnCl2 2H2O (15.45 g, 0.067 mol) in 2 N HCl (47.6 mL), 1/3-benzyl-2-methyl-5-nitro-1H/3H-benzimidazole (3) (4.25 g, 0.019 mol)was heated at 110 C for 7 h. After completion of the reaction,the suspension was neutralized with 2 N NaOH and diluted withethanol. Filtered the solid product and extracted the filtrate with chloroform, dried over Na2SO4, filtered and concentrated to getmixture of products which were separated through column chromatographyusing ethyl acetate/methanol (19:1) as eluent to getsolid compounds 4a and 4b.

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; Singla, Prinka; Luxami, Vijay; Paul, Kamaldeep; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1691 – 1700;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Application In Synthesis of Ethyl 1H-imidazole-2-carboxylate

Description 43; Lambda/-(3-Fluorophenyl)-1-(1W-imidazol-2-ylcarbonyl)-4-piperidinamine (D43); Ethyl imidazole-2-carboxylate (701 mg, 5.0mmol) and D12 (971 mg, 5.0mmol) were dissolved in toluene (25ml) and flushed with argon. This solution was cooled to 00C and treated with trimethylaluminium (7.5ml, 2M solution in hexanes, 15mmol). The mixture was then warmed to 250C and stirred for 16h. The temperature was raised to 500C and the mixture stirred for 4h. The mixture was cooled to 250C and stirred for 3days then treated with Rochelle’s salt (20ml) and stirred for 1h. The resultant solution was poured into water (30ml) and extracted with EtOAc (3x40ml). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography on silica eluting with a 0-10percent MeOH/DCM gradient gave the title compound as a pale yellow solid (775mg). deltaH (CDCI3, 400MHz) 1.50 (2H, m), 2.21 (2H, d), 3.09 (1H, t), 3.58 (2H, m), 3.68 (1H, m), 4.51 (1H1 d), 5.80 (1 H, d), 6.25-6.40 (3H, m), 7.09 (1H, q), 7.12 (1H, s), 7.20 (1H, s), 10.72 (1H, br s). MS (ES): MH+ 289, (M-H+) 287.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33543-78-1, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/7018; (2007); 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. 17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: (1-Methyl-1H-imidazol-4-yl)methanol

To a solution of intermediate 1 (5g, 44.64 [MMOL)] in CH2CI2 [(10 MI)] at [0C] was added dropwise thionyl chloride (50 [ML)] and then the mixture was stirred at room temperature overnight and then under reflux for 3 hours and then concentrated under reduced pressure. The residue was treated with diethyl oxide and the resulting precipitate was filtered and dried. The title compound was obtained as a brown solid [(4G,] 53. 80%); 1HNMR (300 MHz, [DS-DMSO, PPM). S] : 9.25 (s , 1H), 7.8 (s, 1H), 4.95 (s, 2H), 3.9 (s, 3H).

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 17289-25-7.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13134; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1739-84-0, A common heterocyclic compound, 1739-84-0, name is 1,2-Dimethyl-1H-imidazole, molecular formula is C5H8N2, 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.

To a solution of 1,2-dimethyl-1H-imidazole (1a) (96 mg, 1 mmol) in DMF (5 mL), was added NBS (169 mg, 0,95 mmol) and the resulting reaction mixture was stirred in the dark at room temperature for 3 h. The orange-yellowish solution thus obtained was diluted with EtOAc (50 mL), washed with a 10% aqueous solution of NaOH (2 x 50 mL), water (50 mL) and brine (50 mL). The aqueous phases were back-extracted with EtOAc (50 mL) and the combined organic phases dried over Na2SO4 and filtered. The solvent was removed at reduced pressure, affording the title compound as colorless crystals (3.78 g, 76%).

The synthetic route of 1739-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 93-84-5, A common heterocyclic compound, 93-84-5, name is 5-Nitro-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5N3O3, 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.

Concentrated hydrochloric acid (5 drops) was added to a suspension of 5-nitro-1, 3-dihydrobenzimidazol-2-one (intermediate 10,0. 96g) in phosphorus oxychloride (25ml) and the mixture was stirred and heated at reflux for 7h. The cooled mixture was poured into a mixture of ice and water and the precipitated product was extracted into ethyl acetate. The organic phase was dried (MgSO4), filtered and the filtrate was evaporated to give 2-chloro-5-nitrobenzimidazole as a tan coloured solid (0.9g). ‘H NMR (DMSO-d6) d 14.0 (brs, 1H) 8.45 (brs, 1H) 8.15 (d, 1H) 7.7 (d, 1H)

The synthetic route of 93-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LTD.; WO2005/35526; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1546-79-8,Some common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, molecular formula is C5H3F3N2O, 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 22b (racemic mixture)Ethylmagnesium bromide (3M in ethyl ether, 3.95 ml, 11.84 mmol) is added dropwise to example 21a (1.6 g, 5.92 mmol) dissolved in anhydrous THF (20 mL) cooled to 0C. Stirring is continued at 0C for 15 min then overnight at room temperature. The reaction mixture is cooled to 0C and methylmagnesium bromide (3M in ethyl ether, 1.97 ml, 5.92 mmol) is added dropwise. Stirring is continued at 0C for 15 min followed by 2h at room temperature. The reaction mixture is cooled to 0C, aqueous NH4C1 is added dropwise and stirring is continued for 5 min. EtOAc is added, the organic layer separated, washed with brine, dried over Na2SC”4 and concentrated under reduced pressure to furnish 1.37 g of crude ketone. Lithium bis(trimethylsilyl)amide (1,8M, 1.03 mL, 1.86 mmol) is added dropwise to the crude ketone (370 mg, 1.55 mmol) dissolved in anhydrous THF (10 mL) and cooled to -78C. Stirring is continued at -20C for lh. The reaction mixture is cooled to -78C and l-(trifluoroacetyl)imidazole (0.70 ml, 6.18 mmol) is added. Stirring is continued 3 h at room temperature. Aqueous NH4C1 solution and EtOAc are added, the organic layer is separated, dried over a phase-separator cartridge and concentrated under reduced pressure to furnish a residue that is purified by Si flash chromatography (5-40% EtOAc/Hexane as eluent) to obatain 190 mg of intermediate. Hydro xylamine hydrochloride (512 mg, 7.37 mmol) is added to such product dissolved in MeOH (20 mL) and the reaction mixture refluxed for 2h. Volatiles are evaporated under reduced pressure, the residue is partitioned between EtOAc and saturated NaHCC>3, the organic layer is separated, washed with saturated NaHCC>3, dried over phase separator cartridge and concentrated under reduced pressure to furnish a 90mg of residue. TEA (50 mu, 0.36 mmol) followed by methanesulfonyl chloride (26 mu, 0.33 mmol) are added to such residue dissolved in DCM (10 mL) and cooled to 0C. Stirring is continued at room temperature then further TEA (50 mu, 0.36 mmol) and methanesulfonyl chloride (26 mu,, 0.33 mmol) are added and stirring is continued for 2h. Water and DCM are added, the aqueous layer is further extracted with DCM, the organic layers are combined, dried over a phase-separator cartridge and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (eluent 0-10% EtOAc/hexane) to furnish the title compound (20 mg, 23% on the last step).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; WO2013/17657; (2013); A1;,
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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 71759-89-2

EXAMPLE 47 Benzo[1,3]dioxol-5-ylmethyl-(3-[3-(4-iodo-imidazol-1-yl)-[1,2,4]thiadiazol-5-yl]-methyl-amino}-propyl)-carbamic Acid tert-butyl Ester Example 47 was prepared following the procedures described in the preparation of Example 1 using 4-iodo-1H-imidazole. [M+H]+598.90.

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; KALYPSYS, INC.; US2007/123572; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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. Quality Control of (1H-Benzo[d]imidazol-2-yl)methanamine

The solution of Boc-( )-3-amino-4-(2,4-dichlorphenyl)butyric acid (30 mg , 0,086 mmoL 1 ,0 equiv), DIPEA ( 3 equiv), EDC HCi ( 1.5 equiv) and DMAP (1.0 equiv) in DCM (20 mL) was stirred for 1 Grain. To this reaction mixture ( 1 H-benzo[d]imidazol-2- yljmethanamine (1 .0 equiv) was added. The reaction mixture was stirred at room temperature overnight. The organic layer was washed with aq NaHC03 and brine. It was then dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography. The above purified compound was dissolved in 3 ml of DCM, To the solution, 1 ml of TFA was added dropwise. The solution was stirred for 40 min at room temperature. The reaction mixture was evaporated under vacuum, neutralized with aq aHC03 and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concen (M – i i , 378.3.

The synthetic route of (1H-Benzo[d]imidazol-2-yl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5955-72-6, A common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, molecular formula is C7H4ClN3O2, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil. Step 4. To a solution of methyl glycolate in dry THF (8 ml) cooled at 0 C was added NaH (60%) in mineral oil. The reaction was stirred at room temperature for 2h. The suspension was cooled at 0 C and a solution of A/1482/82/1 was added dropwise. The reaction mixture was stirred at room temperature for 16h. UPLC showed ~70% reaction completion, and another 1.1 eq of NaH was added. After stirring for 16h, UPLC showed formation of side products. The reaction was stopped, and S. NH4C1 and EtOAC were added. The organic phase was separated, dried and evaporated to give a crude product, which was then purified by silica column (CyHex to CyHex: EtOAc= 85:15). The product named A/1482/83/1 was recovered with a 50% of purity grade (by NMR), with the UPLC retention time of the impurity that same as that of the desired product.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 870837-18-6, Safety of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

To a solution of the thus obtained 3-methoxy-4-(4-methylimidazol-1-yl)benzaldehyde (4.00 g) in tetrahydrofuran (40 mL), diethylphosphonoacetic acid ethyl ester (4.00 mL) and lithium hydroxide monohydrate (932 mg) were added sequentially, and the reaction mixture was stirred overnight. After confirming the disappearance of the starting materials, 2N aqueous sodium hydroxide (30 mL) and ethanol (5 mL) were added to the reaction mixture, which was then stirred overnight at room temperature. The reaction mixture was cooled to 0 C., followed by addition of 2N hydrochloric acid (30 mL). The resulting precipitates were collected using a Kiriyama funnel and washed with water and ethyl acetate to give (E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid (4.61 g). The physical property data of the resulting compound are as shown below. 1H-NMR (DMSO-d6) delta (ppm): 7.81 (s,1H), 7.60 (d,J=16 Hz,1H), 7.56 (s,1H), 7.39 (d,J=8.0 Hz,1H), 7.35 (d,J=8.0 Hz,1H), 7.16 (s,IH), 6.66 (d,J=16 Hz,1H), 3.88 (s,3H), 2.15 (s,3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Eisai Co., Ltd.; US2006/241038; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem