Month: March 2021

Application of 2466-76-4, 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. 2466-76-4 name is 1-(1H-Imidazol-1-yl)ethanone, 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: To a solution of N -acetylimidazole 7a (1 mmol) and a suitable Baylis-Hillman acetate 1 (1 mmol) in DMF (1 mL), K2CO3 (1 mmol) was added and the resulting mixture was stirred at room temperature until complete consumption of N -acetylimidazole 7a. The reaction mixture was then diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4 . After removal of the solvent under reduced pressure, the residue was puried by flash chromatography over silica gel with EtOAc and hexane (1:1).

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

Reference:
Article; Koeseceli Oezenc, Ay?en; Celik, Ilhami; Koekten, ?ule; Turkish Journal of Chemistry; vol. 41; 3; (2017); p. 323 – 334;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 641571-13-3, These common heterocyclic compound, 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, 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.

General procedure: A solution of 5 compound (10 mg, 0.028 mmol), substituted benzoic acid (0.028 mmol), HOBt (6.8 mg, 0.05 mmol), EDCI (8.05 mg, 0.04 mmol) and TEA (10 muL, 0.07 mmol) in DMF (0.5 mL) was stirred at room temperature for overnight. The reaction mixture was dilluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic layer dried over Na2SO4. Purification of column chromatography with Hexane/ethyl acetate = 1:1 to afford compound 6 as a white solid.

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid is playing an increasingly important role. we look forward to future research findings about 641571-13-3.

Reference:
Article; Kim, Mi-Hyun; Kim, Minjung; Yu, Hana; Kim, Hwan; Yoo, Kyung Ho; Sim, Taebo; Hah, Jung-Mi; Bioorganic and Medicinal Chemistry; vol. 19; 6; (2011); p. 1915 – 1923;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 98873-55-3, The chemical industry reduces the impact on the environment during synthesis 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, I believe this compound will play a more active role in future production and life.

10.9 g of potassium hydroxide was added to 200 ml of dimethylsulfoxide,A solution prepared by dissolving 7.5 g of 1-cyanomethylimidazole and 5.2 g of carbon disulfide in 100 mL of dimethyl sulfoxide under cooling in a water bath was added dropwise thereto,And stirred at room temperature for 1 hour to prepare a dithiolate solution.Subsequently, under cooling in a water bath, the resultant dithiolate solution was added to 200 mL of dimethylsulfoxide, 26.1 g of the crude product (S) -1- (2,4-dichlorophenyl) -ethan-1,2-bismethanesulfonate Was added dropwise to the solution.After stirring at room temperature for 2 hours, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water,After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography (ethyl acetate / hexane = 2/1).The resulting crystals were dissolved in ethyl acetate,Hexane mixed solvent to obtain 5.1 g (the yield: 21%) of the desired product.The purity of the product is 99.66%.

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-(1H-Imidazol-1-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyongbo Pharmaceutical Co., Ltd.; Son, Hwe Joo; Kim, Young Taek; Oh, Do Yeon; Kim, Sung Ho; (9 pag.)KR2016/61542; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, 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. 57090-88-7 name is 1H-Imidazole-4-carbonitrile, 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: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
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. Computed Properties of C4H6N4O2

Preparation tetranitro glycoluril: equipped with a reflux condenser, a thermometer, a stirrer, pressure-equalizing dropping funnel, the reaction 3000ml four-necked round flask, 500ml of fuming nitric acid.When the temperature to about 10 , 20g glycoluril added rapidly, stirred to dissolution, to give glycoluril – fuming nitric acid solution; the glycoluril – nitric acid solution is sent down to the temperature of the smoke 0 ~ 5 , 250ml of acetic anhydride was added dropwise, drops added maintaining the temperature at 0 ~ 5 ; acetic anhydride addition was completed, the nitration temperature is maintained at 0 ~ 5 , nitration reaction after 4h, the temperature raised to nitration 5 ~ 10 , 3H continued nitration; nitrated using a temperature gradient to gradually warm ,, 5 gradient for 2 hours and then raised 5 , nitration began maintaining the temperature at 0 deg.] C, nitration reaction 2h, 5 increased, i.e., the temperature was raised 5 nitration, nitration continued 2h, then increased 5 , i.e. nitration temperature was raised to 10 , maintained for 3 hours.10min nitration reaction bottle with a precipitate beginning, gradually warming nitration temperature gradient, the amount of precipitation as the reaction temperature, the reaction time increased, the precipitation was complete, the reaction mixture was lowered vial -10 ~ 0 , the reaction was stopped, the bottle within fritted funnel mixture was filtered, the white solid was washed with tetranitromethane glycoluril dichloromethane to large neutral stand soaked in dichloromethane

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; Hubei Aerospace Institute of Chemical Technology, CASC; Ha, HengXin; (8 pag.)CN105777575; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, molecular formula is C9H7N3O2, 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: C9H7N3O2

Step 5 4-(Imidazol-1-yl)aniline, dihydrochloride A mixture of 4-(imidazol-1-yl)nitrobenzene (89.60 g, 0.474 mol) and 10% palladium on carbon (4.50 g) in ethanol (1200 ml) and 5N HCl (189 ml) was hydrogenated in two batches at 40 psi for 80 minutes. Water (450 ml) was then added to dissolve the product and the catalyst was removed by filtration, washing with more water, and the combined filtrates were evaporated in vacuo, using finally a freeze drier, to give 105.4 g (96%) of the title compound as a cream solid. deltaH (250 MHz, D2 O) 7.22 (2H, d, J=8.8 Hz), 7.35 (1H, t, J=2.1 Hz), 7.44 (2H, d, J=9.0 Hz), 7.59 (1H, t, J=1.8 Hz), 8.89 (1H, t, J=1.5 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2301-25-9, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US6150391; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 5-methyl-1H-imidazole-4-carboxylate

Add DIAD (2.01 g, 9.74 mmol) dropwise at 0-5 ¡ãC under nitrogen followed by 2,2-difluoroethanol (0.64 g, 7.79 mmol) to a stirring solution of ethyl 4-methyl-1H-imidazole-5-carboxylate (1.00 g, 6.49 mmol) and triphenylphosphine (2.60 g, 9.71 mmol)THF (20 mL). Stir the mixture at 10-15 ¡ãC for 16 hrs. Concentrate the mixture and purify by silica gel combi-flash chromatography eluting with EtOAc in PE from 10percent to 35percent to give the title compound (0. 47 g, 33.2percent) as yellow oil. LC/MS (mlz): 219 (M+H).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; HU, Zhilong; LIU, Lianzhu; MA, Tianwei; ZENG, Mi; ZHANG, Haizhen; (37 pag.)WO2018/14800; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 360-97-4, These common heterocyclic compound, 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, 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.

(b) tert-Butyl {2-[(5-carbamoyl-lH-irnidazol-4-yl)amno]-l-methylethyl}comega’bamate; To a stirred solution tert-butyl (l-methyl-2-oxoethyl-carbamate (0.82 g, 4.8 mmol, obtained from Example 29(a)) in ethanol (10 mL) was added 5-aminoimidazole-4- carboxamide (9.4 mL, 67 mmol). After 1 h, glacial acetic acid (0.28 mL, 4.0 mmol) was added. After another 1 h, sodium cyanoborohydride (0.48 g, 4.0 mmol) was added. After 20 h, the solvent was removed in vacuo. The product was purified by silica gel column chromatography (dichloromethane / methanol, 95:5 then 90:10) to give the title compound (0.95 g, 66% yield) as a solid.1H NMR (CDCl3) delta ppm 7.17 (IH), 6.51 (IH), 4.71 (IH), 3.57-3.46 (IH), 3.40 (IH)5 3.06- 2.96 (IH)5 1.48 (9H)5 1.25 (3H); MS (ESI) m/z 284 (M+l).

Statistics shows that 4-Amino-1H-imidazole-5-carboxamide is playing an increasingly important role. we look forward to future research findings about 360-97-4.

Reference:
Patent; ASTRAZENECA AB; WO2007/120098; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33468-69-8, The chemical industry reduces the impact on the environment during synthesis 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

Example 35 Synthesis of 1- [l-(4-fluorophenyl)-5-isopropylpyrazol-4-yl] -3- [4- [0190] A mixture of 3-bromo-l-[l-(4-fluorophenyl)-5-isopropyl-pyrazol-4-yl]pyrrolidin-2- one (0.020 g, 0.055 mmol), 4-(trifluoromethyl)- lH-imidazole (0.024 g, 0.17 mmol) and K2C03 (0.030 g, 0.22 mmol) in DMF (0.6 mL) was stirred at 60 C for 1 hr. The mixture was then cooled to room temperature, quenched with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by reverse phase HPLC (CI 8 column, acetonitrile-H20 with 0.1% TFA as eluent) to yield the title compound (0.022 g, TFA salt, 75%); XH NMR (TFA salt) (400 MHz, CDC13) delta 7.98 (s, 1 H), 7.59 (s, 1 H), 7.51 (s, 1 H), 7.39 (dd, J= 8.4, 4.8 Hz, 2 H), 7.20 (dd, J= 8.6, 8.6 Hz, 2 H), 5.06 (dd, J= 10.8, 8.8 Hz, 1 H), 3.90 (m, 1 H), 3.83 (m, 1 H), 2.98 (m, 2 H), 2.54 (m, 1 H), 1.21 (d, J= 7.2 Hz, 3 H), 1.20 (d, J= 7.2 Hz, 3 H); MS: (ES) m/z calculated for (free form) [M + H]+ 422.1, found 422.1.

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, 4-(Trifluoromethyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Pingchen; LI, Yandong; POWERS, Jay P.; MALATHONG, Viengkham; PUNNA, Sreenivas; TANAKA, Hiroko; ZHANG, Penglie; WO2014/89495; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-31-8, name is 5-Chloro-1H-imidazole, 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. HPLC of Formula: C3H3ClN2

To a solution of 4-chloro-1H-imidazole (180g, 1.76 mol, 1.00 eq) in dry dichloromethane (3.0 L) at 0C wasadded aq. NaOH (1 M, 2.11 L, 2.11 mmol, 1.20 eq) followed by tetra-n-butylammonium bromide (56.6 g, 0.176 mol, 0.10 eq). To this biphasic solution was added dropwise allyl bromide (167 mL, 1.93 mol, 1.10 eq) and the resulting mixture was stirred at room temperature for 20h. Thereafter the reaction mixture was diluted withwater (1 L), extracted with dichloromethane (2 x 1 L), the combined organic layers were dried (Mg504) and concentrated in vacuo, to provide 290 g of a mixture of regioisomers (80% purity, 93% yield), which were separated by distillation at reduced pressure (0.1 mbar). MS (El): 142.1 ([M])

The synthetic route of 15965-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; WACHENDORFF-NEUMANN, Ulrike; GOeRTZ, Andreas; DAHMEN, Peter; DUCROT, Virginie Pascale; (195 pag.)WO2018/50456; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem