Tag: M.W=100-200

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. 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, A new synthetic method of this compound is introduced below., Safety of 5-Amino-1H-imidazole-4-carboxamide hydrochloride

AIL round-bottom flask (three neck) containing 340 g of trifluoroacetamide was heated in an oil bath at [110 C.] After the trifluoroacetamide melted, 50 g of 5- [AMINOIMIDAZOLE-4-CARBOXAMIDE-HCL] was added. The mixture was warmed to reflux (bath temp 160 to [165 C)] for 4 hours, cooled to room temperature, and the rocky solid was triturated with [1] L of ether. The ether was decanted off and the remaining solid was warmed until melted and 200 mL of ether was introduced by a dropping-funnel through a water-cooled condenser. The mixture was cooled to room temperature and an additional 200 mL of ether was added with stirring. The solid was removed by filtration, triturated with 3 x 500 mL of ether, washed with 200 mL of H20, and filtered to provide 89 g of crude product. The product was treated with 3 L [OF MEOH] and 9 g of activated carbon, warmed to reflux for 20 minutes, filtered through a pad of celite, and concentrated to a volume of 2.5 L. The material was warmed to dissolve all the precipitate that formed and then cooled slowly to room temperature. The crystalline material was isolated by filtration and dried in vacuo to provide 41 g of the desired hypoxanthine as a white solid. [‘H] NMR (DMSO-d6) [S] 8. 34 (s, 1H), 7.18 (bs, 2H). MS (ES+), 205.0 (100%, M + H).

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; MEMORY PHARMACEUTICALS CORPORATION; WO2004/14913; (2004); 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 496-46-8 as follows. Quality Control of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Synthesis of cucurbit[n]urils in methanesulphonic acid (MSA) using paraformaldehydeUnsubstituted glycoluril (20 g) and methanesulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 90 C. Paraformaldehyde (8.45 g) was added in portion-wise and the reaction mixture was then heated to 100 C (internal) for 18 hours. The reaction mixture was cooled and added to methanol (410 ml) to produce a brown powder which was analysed by1H NMR.Approximate Yields by1H NMR (% of recovered product) cucurbit[5]uril 0%, cucurbit[6]uril 63%, cucurbit[7]uril 35%, cucurbit[8]uril 0%, cucurbit[9]uril 0%, cucurbit[10]uril 0% cucurbit[11]uril 0%.Residual formaldehyde by HPLC method was 1621 ppm.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
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These common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. HPLC of Formula: C4H6N2S

EXAMPLE 28 A mixture consisting of 2.85 g (25 mmoles) of 1-methyl-2-mercaptoimidazole, 22 mg (0.12 mmoles) of saccharin, 20 ml of toluene and 5.2 ml (25 mmoles) of hexamethyldisilazane was refluxed for 1 hour and after cooling to room temperature, 5.40 g (25 mmoles) of 4-nitrobenzyl bromide and then 5 ml of hexamethylphosphoric triamide were added to the mixture which contained 1-methyl-2-(trimethylsilylthio)-imidazole. After stirring for 2 hours at room temperature, the mixture was diluted to 150 ml with ethyl acetate and the solution thus obtained was washed three times with 50 ml of a saturated sodium bicarbonate solution and then twice with 20 ml of water. The organic layer was dried, filtered and evaporated to dryness and the crystalline residue was washed with 100 ml of petroleum ether (boiling range 60-80 C.) and then vacuum dried to obtain 5.54 g (89% yield) of 1-methyl-2-(4-nitrobenzylthio)-imidazole melting to 74-77 C. Crystallization of a sample from ethanol raised the melting point to 77.5-78.0 C.

The synthetic route of 1-Methyl-1H-imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gist-Brocades N.V.; US4496720; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 705-09-9,Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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: Example 2: General procedure for the preparation of compounds (IB 1-20): Cynuric chloride (1) (lOg, 54.2 mmol, 1.0 eq) was substituted by morpholine (7) (4.72 ml, 5.42 mmol, 1.0 eq) in methylene chloride (60 ml), at -50 C for 20 min to obtain intermediate (3). The intermediate (3) (5 g, 1.0 eq) on further treatment with di-substitued benzimidazole (7) (1.4 eq) in presence of K2C03 (1.44 eq) in DMF (20 ml) , at -5 C for 30 min and then at room temperature for 4 h led to intermediate (8) . To the solution of intermediate (8) (100 mg, 1.0 eq) in DMF (3 ml) are added K2C03 (1.4 eq) and substituted aryloxy piperidines (6) (1.44 eq).This resulting reaction mixture was stirred at room temperature for 24 h. The thus-obtained mixture was poured into water (30 ml) and extracted with ethyl acetate twice washed with 2N HC1 solution and dried under vacuo. This crude product was purified by silica gel column chromatography using an ethyl acetate and hexane mixture as solvent to obtained the compounds formula (1B1-20).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Difluoromethyl)-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; THATIKONDA, Thanusha; KUMAR, Suresh; SINGH, Umed; MAHAJAN, Priya; MAHAJAN, Girish; NARGOTRA, Amit; MALIK, Fayaz; MONDHE, Dilip Manikrao; VISHWAKARMA, Ram Asrey; SINGH, Parvinder Pal; (60 pag.)WO2016/79760; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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. Recommanded Product: 1,1′-Thiocarbonyldiimidazole

To a stirred solution of 6.8 g (35.0 mmol) of (5) in 150 mL of CH2Cl2 at RT was added 6.4 g (35 mmol) of 1,1?-thiocarbonyldiimidazole. The mixture was stirred at room temperature for 15 minutes and then evaporated under reduced pressure and the residue was passed through a short pad of silica gel, eluting with a gradient of hexane/EtOAc, which gave (5-Isothiocyanato-2-methoxy-phenyl)-methyl-propyl-amine (6) (7.85 g, 95%) as a colorless oil.

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

Reference:
Patent; Synta Pharmaceuticals Corp.; Du, Zhenjian; Foley, Kevin Paul; US9108933; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

(95a) Using conditions analogous to (1f), 2-methyl-5-nitro-benzimidazole (101 mg, 0.568 mmol) was reacted with methyl 4-(bromomethyl)-benzoate to provide the desired ester (71 mg, 40%). MS found: (M+H)+=326.

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-5-nitro-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ott, Gregory R.; Chen, Xiao-Tao; Duan, Jingwu; Lu, Zhonghui; US2003/139388; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 714273-83-3, These common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, 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.

5 g (32.85 mmol) of 5-(tert-butyl)-1H-imidazole-4-carbaldehyde was added to 35 mL of DMF,An additional 13.02 g (65.7 mmol) of N,N’-diacetylpiperazine-2,5-dione nitrogen was added to protect the exhaust, and 16.05 g (49.28 mmol) of cesium carbonate was added to protect the exhaustThe reaction was stirred at room temperature in the dark for 20 h. The reaction solution was poured into 500 mL of ice water and suction filtered.The filter cake was washed with water (100 mL * 2), petroleum ether: ethyl acetate = 8: 1 (400 mL),The filter cake was dispersed ultrasonically with ethanol and dichloromethane, insoluble matter was filtered off, and concentrated under reduced pressure.Anhydrous ethanol with water. It was further slurried with ethyl acetate (200 mL) to obtain a brown-yellow solid. Get 4.05 g of (Z)-1-acetyl-3-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)piperazine-2,5-dione, Yield: 42%.

The synthetic route of 714273-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Li Wenbao; Fu Zhangyu; Hou Yingwei; Ji Cunpeng; Wang Shixiao; Ma Mingxu; Guan Huashi; (21 pag.)CN110240592; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1457-58-5, name is 2-Methyl-1H-imidazole-5-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 1457-58-5, Safety of 2-Methyl-1H-imidazole-5-carboxylic acid

Intermediate 661 -(2-Fluoro-4-methanesulfonylphenyl)-2-methyl-1 H-imidazole-4-carboxylic acidA mixture of 2-methyl-1 H-imidazole-4-carboxylic acid (500 mg), N,N-diisopropyl- ethyl-amine (4 mL), and 1 ,2-difluoro-4-methanesulfonylbenzene (1 .2 g), in N,N- dimethylformamide (6 mL) is heated to 120 C overnight. The crude product is purified by HPLC. LC (method 20): tR = 0.90 min; Mass spectrum (APCI): m/z = 299 [M+H]+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); 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. 53981-69-4, name is 1-(1H-Imidazol-2-yl)ethanone, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(1H-Imidazol-2-yl)ethanone

To a mixture of l-(l /-imidazol-2-yl) ethan-l-one (32 mg, 0.290 mmol) and 2-(4- formylphenyl)-N-(perfluorophenyl) acetamide (124 mg, 0.377 mmol, 1.3 eq) in a microwave vial under nitrogen were added piperidine (61 mu, 0.726 mmol, 2.5 eq) and anhydrous methanol (5.0 mL) via syringe. The reaction mixture was heated in the microwave synthesizer for 5 h and it was monitored by TLC (50% ethyl acetate/hexanes). Methanol was removed on a rotary evaporator to obtain a brown oil. It was chromatographed by preparative TLC in 50-75% ethyl acetate /hexanes to obtain (£)-2-(4-(3-(l /-imidazol-2-yl)-3-oxoprop- l-en-l-yl) phenyl)-N-(perfluorophenyl) acetamide 35 as a brown solid (16 mg, 13.07%). TLC R/ = 0.5 (50% ethyl acetate/hexanes), mp 235 C. NMR (600 MHz, CD3OD) delta 7.94 (s, 1H), 7.92 (s, 2H), 7.89 (s, 2H), 7.86 (s, 1H), 7.75 (d, J = 8.1 Hz, 6H), 7.46 (d, J = 8.0 Hz, 6H), 7.41 (s, 3H), 7.29 (s, 3H), 3.83 (s, 7H). 13C NMR (151 MHz, MeOD) delta 178.61, 170.86, 166.79, 145.98, 140.81, 137.75, 133.73,130.15,129.59,128.66 ,121.42120.82,41.70 ppm. HRMS calcd for C20H14F5N3O2 :423.10 found: 423.1146

The synthetic route of 53981-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF TOLEDO; TILLEKERATNE, Viranga; AL-HAMASHI, Ayad; DLAMINI, Samkeliso; ALQAHTANI, Abdulateef, Saeed; KARAJ, Endri; (69 pag.)WO2019/36607; (2019); 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. 92507-97-6, name is 1-ethyl-2,3-dimethylimidazolium chloride, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-ethyl-2,3-dimethylimidazolium chloride

Example 181-Ethyl-2,3-dimethylimidazolium cyanodifluoropentafluoroethylborate-[C7H13N2][C2F5BF2(CN)] Potassium cyanodifluoropentafluoroethylborate K[C2F5BF2(CN)] (4.2 g, 18.0 mmol) is taken up in deionised water (2 ml), and a solution of 1-ethyl-2,3-dimethylimidazolium chloride [EDMIM]CI (3.2 g, 19.9 mmol) in 3 ml of deionised water is added. The ionic liquid obtained is washed with deionised water (4×2 ml), separated off and dried at 50 C. in vacuo. The yield of 1-ethyl-2,3-dimethylimidazolium cyanodifluoropentafluoroethylborate, which is liquid at room temperature, is 5.1 g (15.9 mmol), 88%, based on the potassium cyanodifluoropentafluoroethylborate K[C2F5BF2(CN)] employed. The product is analysed by means of ion chromatography and has low levels of contamination with halide; chloride: 7 ppm, bromide: 16 ppm, fluoride: 14 ppm. Water content (Karl Fischer titration): 161 ppm. Dynamic viscosity (20 C.): 47.2 mPa·s.Raman spectroscopy: v (CN)=2209 cm-1 1H-NMR: delta, ppm=7.60 d (CH, 1H), 3JH,H=2.15 Hz; 7.55 d (CH, 1H), 3JH,H=2.15 Hz; 4.32 q (CH2, 2H), 3JH,H=7.30 Hz; 3.90 s (CH3, 3H); 2.75 s (CH3, 3H); 1.46 t (CH3, 3H), 3JH,H=7.30 Hz.13C{1H}-NMR (cation): delta, ppm=145.32 s (Ctert, 1C); 123.30 s (CH, 1C); 121.19 s (CH, 1C); 44.20 s (CH2, 1C); 35.35 s (CH3, 1C); 15.07 s (CH3, 1C); 9.46 s (CH3, 1C).11B-NMR: delta, ppm=-2.7 tt (1B), 1JF,B=51.0 Hz, 2JF,B=25.3 Hz.19F-NMR: delta, ppm=-83.3 t (CF3, 3F), 4JF,F=5.2 Hz; -136.3 q (CF2, 2F), 2JF,B=23.3 Hz; -167.2 qq (BF2, 2F), 1JF,B=51.1 Hz, 4JF,F=5.1 HzElemental analysis: found, %, C, 37.57; H, 3.84; N, 13.10; calculated for C10H13BF7N3, %, C, 37.65; H, 4.11; N, 13.17.

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 92507-97-6.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2012/309981; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem