Category: 15965-31-8

Electric Literature of 15965-31-8, 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. 15965-31-8, name is 5-Chloro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-chloro- 1 H-imidazole (5.0 g, 48.8 mmol), l-chloro-2-methoxy-4- nitrobenzene (9.15 g, 48.8 mmol), and potassium hydroxide flakes (2.74 g, 48.8 mmol) in anhydrous DMSO (50 mL) was heated at 80 0C for 20 h. The reaction mixture was allowed to cool to rt and was poured into 800 mL of water with vigorous stirring. The resulting yellow-orange precipitate was collected by vacuum filtration using a coarse sintered glass funnel. The crude wet solid was transferred to a 1 L Erlenmeyer flask. Absolute ethanol (250 mL) was added to the flask and the resulting suspension was heated until all of the solids dissolved. The clear solution was cooled to rt and the desired product slowly crystallized. After 2 h, the crystalline solid was collected by vacuum filtration and rinsed with 100 mL of fresh ethanol. The solid was dried under high vacuum to afford 4-chloro- l-(2-methoxy-4-nitrophenyl)-l H-imidazole (5.2 g, 42 % yield) as an off-white crystalline solid. LC-MS (M+H)+ = 254.0. 1H NMR (500 MHz, CDCl3) delta ppm 7.94 – 8.01 (m, 2 H) 7.76 (d, J=I.53 Hz, 1 H) 7.45 (d, J=8.55 Hz, 1 H) 7.21 (d, ./=1.53 Hz, 1 H) 4.02 (s, 3 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, 5-Chloro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 15965-31-8, 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. 15965-31-8, name is 5-Chloro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-chloro-l-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (550 mg; 1.74 mmol) and 4- chloroimidazole (214 mg; 2.09 mmol; 1.20 eq) in dry acetonitrile (5.0 mL) was stirred at 80C for 20 h, then at 130C for 1 h under microwave irradiation. Thereafter the reaction mixture was allowed to cool down to room temperature, diluted with water, the organic layer was washed with saturated aqueous sodium bicarbonate, dried (MgSO i) and concentrated to dryness in vacuo. The oily residue was purified by chromatography over silica gel, eluted with a mixture of w-heptane/ethyl acetate (100:0 to 0: 100). After evaporation of the solvents, a second purification by preparative HPLC was performed. Evaporation of the solvents in vacuo afforded 141 mg (21%) of l-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(5-chloroimidazol- l-yl)ethanone as a colourless solid. MS (ESI): 381.0 ([M+H]+)

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

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; GENIX, Pierre; MILLER, Ricarda; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; GOeRTZ, Andreas; (104 pag.)WO2018/60088; (2018); 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. COA of Formula: C3H3ClN2

Example 11 : Preparation of 3-f5-(4-chloroimidazol-1-yl)-2-ethylphenyllbicvclo[3.2.1loctane-2.4- dione and 3-f5-(5-chloroimidazol-1-yl)-2-ethylphenyllbicvclor3.2,Hoctane-2,4-dione3-(5-Bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione (100mg, 0.31 mmol), 4-chloroimidazole (47mg, 0.46mmol), potassium phosphate (264mg, 1.24mmol), L-proline (36mg, 0.31 mmol) and copper (I) iodide (60mg, 0.31 mmol) are combined in a microwave vial, suspended in DMSO and heated under microwave irradiation at 1600C for 45 minutes. The mixture is filtered and purified by preparative reverse-phase HPLC to give a mixture of 3-[5-(4-chloroimidazol-1-yl)-2- ethylphenyl]bicyclo[3.2.1]octane-2,4-dione and 3-[5-(5-chloroimidazol-1-yl)-2-ethylphenyl]- bicyclo[3.2.1 ]octane-2,4-dione.

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

Reference:
Patent; SYNGENTA LIMITED; WO2008/145336; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15965-31-8,Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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.

Intermediate 27: Methyl {2-[(5-chloro-1 H-imidazol-1-yl)methyl1phenyl)acetateMethyl [2-(bromomethyl)phenyl]acetate (Intermediate 1 , 3 g, 12.34 mmol) and 4-chloro- 1 H-imidazole (Intermediate 26, 3.80 g, 37.0 mmol) were dissolved in dry DMF (100 ml) and stirred at room temperature for 16 hours. After dilution with water the mixture was extracted with DCM, the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (5Og) eluting with a gradient of MeOH in DCM from 0 to 5% to afford the title compound (1.6 g, 6.04 mmol) contaminated with -10% of the regioisomer methyl {2-[(4-chloro-1 H-imidazol- 1-yl)methyl]phenyl}acetate, which was used in the next step without further purification; UPLC/MS Rt=0.50 min; m/z (ES): 265 and 267 [M+H]+ ; 1H NMR (CDCI3) only signals relating to the title compound: delta 3.71 (s, 2H), 3.72 (s, 3H), 5.21 (s, 2H), 6.92 (d, 1 H), 7.05 (d, 1 H), 7.28-7.42 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-1H-imidazole, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; GIANOTTI, Massimo; LESLIE, Colin Philip; STASI, Luigi Piero; WO2010/142652; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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 5-Chloro-1H-imidazole

2.2. Synthesis of 1-[(4-chloro-lH-imidazol-1-yl) methyl]-4-(3, 4, 5-trifluorophenyl)- pyrrolidin-2-one 72 using thionyl chloride. Alternatively to method 2.1, 1-imidazol-1-ylmethyl-pyrrolidin-2-ones derivatives can also be obtained by a similar reaction of the hydroxymethyl derivative with successively thionyl choride in toluene for 16 h at room temperature followed by quenching of the chloromethyl derivative with an imidazole in the presence of Et3N at room temperature. For example, 1-hydroxymethyl-4- (3, 4,5-trifluoro-phenyl)- pyrrolidin-2-one reacts with thionyl chloride and 4-chloroimidazole to afford 1- [ (4- chloro-lH-imidazol-1-yl) methyl]-4- (3, 4,5-trifluorophenyl)-pyrrolidin-2-one 72 LC/MS (MH+): 330/332.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15965-31-8, its application will become more common.

Reference:
Patent; UCB, S.A.; WO2005/54188; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem