Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 50995-95-4, name is 2-Propylimidazole, 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 50995-95-4, Application In Synthesis of 2-Propylimidazole

Example 30 Methyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionate (1.50 g) and 2-propylimidazole (0.66 g) were dissolved in N,N-dimethylformamide (10 ml), and sodium hydride (60% dispersion in oil, 0.30 g) was gradually added to the resulting solution at room temperature. After this was stirred at room temperature for 3.5 hours, an aqueous solution of 2 N sodium hydroxide (50 ml) was added thereto and stirred for an additional 30 minutes. Water was added to the reaction mixture, and the pH was then adjusted to 6 with 2 N hydrochloric acid. The crystals thus precipitated were collected by filtration, and recrystallized from ethanol to obtain 4-(4-chlorophenyl)-2-(2-propyl-1-imidazolyl)-5-oxazolepropionic acid (1.25 g, 69%) as pale brown needles. mp 174-175 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Propylimidazole, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6177452; (2001); B1;,
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, Computed Properties of C5H8N2O

Thionyl chloride (3.88mL, 53.5mmol) was added dropwise to 3-methyl-3H-imidazol-4- yl)-methanol (o.3g, 2.68mmol). The reaction was sonicated briefly, treated with DMF (1 drop) and allowed to stir at ambident temperature for 1 h. The volatiles were removed and the residue treated with diethyl ether. The diethyl ether was decanted and the procedure repeated 3 times. The semi-solid residue was treated with dimethylamine in THF (6.69mL, 13.38mmol) followed DMF (1 mL). The reaction was heated in a CEM microwave reactor at 8O0C for 30 minutes, treated with acetic acid (1 ml_) and purified by SCX cartridge to give the title compound (0.18g, 1.22mmol). LC-MS (method 1): R, 2.9 min, m/z 140 [MH]+.

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, (1-Methyl-1H-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2008/23157; (2008); 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C5H6N2O

COMPOUND 12. 1.21 : N, N-DIETHYL-4-E1, 2, 3, 4-TETRAHYDRO-6-METHOXY-2- [ 4-METHYL-lH-IMIDAZOL-5-YL) METHYLI-1-ISOOUINOLINYLI- BENZAMIDE; INTERMEDIATE 5.1. 8 (1.1 g, 3.25 mmol) was dissolved in 1,2-dichloroethane (70 mL), 4-methyl-imidazole-5-carboxaldehyde (716 mg, 6.5 mmol) was added and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (2. 1 g, 9.8 mmol) was added and the reaction mixture stirred for a further 16 h. MeOH (5 mL) was added and the reaction mixture concentrated to dryness. The resulting residue was partitioned between EtOAc (50 mL) and NaOH (1N, 30 mL), the aqueous phase washed with EtOAc (2 x 50 mL), dried (MgS04), filtered and concentrated to dryness. The resulting residue was purified by flash chromatography on silica gel (10: 1, DCM: MeOH) to afford COMPOUND 12.1. 21 (736 mg, 54%) as a colourless oil. 1H NMR (500 MHz, CDC) : 8 1. 13,1. 24 (br s, 6H), 2.09 (s), 2.53 (td, J4, 13 Hz, ), 2.76 (br d, J 17 Hz, 1H, ), 2.98 (m, 1H), 3.09 (m, 1H), 3. 28 (br s, 2H), 3.55 (br s, 2H), 3.33 (d, J2 Hz, 1H), 3.60 (d, J2Hz, 1H), 3.76 (s, 3H), 4.56 (s, 1H), 6.58 (s, 1H), 6.64 (br s, 1H), 7.29-7. 30 (m, 5H), 8.30 (s, 1H). 13C NMR (125 MHz, CDC13) : 5 11.2, 13.1, 14.5, 29.2, 39.6, 43.7, 47.0, 49.6, 55.4, 68.0, 112.6, 113.0, 126.5, 127.0, 129.9, 130.0, 130.1, 133.2, 136.1, 136.2, 145.9, 158.1, 171.6. (+) LRESIMS m/z 433 [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; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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.

A mixture comprising compound 158B (350 mg; 0.88 mmol) and 1-trityl-1H-imidazole-4-carboxaldehyde (352 mg; 1.00 mmol) dissolved in 1,2-dichloroethane (DCE) (4.5 ml) in the presence of acetic acid (0.3 ml) is stirred for 5 minutes at room temperature and sodium triacetoxyborohydride (233 mg; 1.10 mmol) is then added. The mixture is stirred overnight at room temperature and is then diluted with ethyl acetate and washed successively with saturated NaHCO3 solution, with water, and with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated. This crude reaction, product is then purified by flash chromatography (gradient: 4/1 and then 2/1 CH2Cl2/acetone) to give the desired product (304 mg; 48%). [0268] 1H NMR, DMSO-d6 (ppm): 1.88 (m, 2H); 2.00 (s, 3H); 2.33 (m, 2H); 3.63 (s, 3H); 4.03 (d, 2H, 5.2 Hz); 4.50 (m, 1H); 5.45 (t, 1H, 5.6 Hz); 6.55 (s, 1H); 6.70 (s, 1H); 6.76 (d, 1H, 8.7 Hz); 7.01 (m, 6H); 7.21 (d, 1H, 8.7 Hz); 7.25 (s, 1H); 7.31-7.41 (m, 13H); 7.55 (d, 1H, 7.4 Hz); 7.73 (d, 3H, 9.4 Hz); 11.35 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Trityl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Perez, Michel; Lamothe, Marie; Hill, Bridget; Etievant, Chantal; US2004/204417; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, These common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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.

Phenstatin (0.500 g, 1.57 mmol), (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (0.296 g, 1.89 mmol), and DIAD (0.40 mL, 2.04 mmol) were dissolved in CH2Cl2. Triphenylphosphine (0.825 g, 3.14 mmol) was added to the mixture, and the reaction mixture was stirred for 24 h. The reaction mixture was then evaporated under reduced pressure. Flash chromatography of the crude product using a prepacked 100 g silica column [eluents: solvent A: EtOAc; solvent B: hexanes; gradient, 17%A/83%B over 1.19 min (1 CV), 17%A/83%B 100%A/0%B over 8.33 min (7 CV), 100%A / 0%B over 5.95 min (5 CV); flow rate 100 mL/min; monitored at 254 and 280 nm] yielded (4-methoxy-3-((1-methyl-2-nitro-1H-imidazol-5-yl)methoxy)phenyl)(3,4,5-trimethoxyphenyl)methanone (31) as a pale yellow-white solid (0.346 g, 0.757 mmol, 48%) [0.284 g, 0.621 mmol, 39%, corrected for EtOAc].1H NMR (600 MHz, CDCl3) delta 7.62 (1H, d, J = 1.7 Hz), 7.52 (1H, dd, J = 8.3, 1.7 Hz), 7.24 (1H, s), 7.04 (2H, s), 6.97 (1H, d, J = 8.4 Hz), 5.18 (2H, s), 4.16 (3H, s), 3.97 (3H, s), 3.96 (3H, s), 3.91 (6H, s).13C NMR (151 MHz, CDCl3) delta 194.16, 153.97, 152.91, 146.74, 141.88, 132.92, 132.30, 130.43, 129.31, 127.00, 116.43, 110.61, 107.52, 99.98, 61.24, 61.01, 56.39, 56.05, 34.54.HRMS [M+Na]+: 480.1376 (calcd for [C22H23N3NaO8]+,480.1377).HPLC retention time (Method B): 4.66 min [100% at 254 nm].

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Winn, Blake A.; Shi, Zhe; Carlson, Graham J.; Wang, Yifan; Nguyen, Benson L.; Kelly, Evan M.; Ross, R. David; Hamel, Ernest; Chaplin, David J.; Trawick, Mary L.; Pinney, Kevin G.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 636 – 641;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 19225-92-4, 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. 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 50; N-{5-amino-3-cyano-1- [2, 6-dichloro-4-pentafluorothiophenyl]-1 H-pyrazol-4-yl}-N [ (1- methyl-1 H-imidazol-2-yl) methyl] methanesulfonamide; To a mixture of Example 38 (200 mg, 0.42 mmol) and 1- (N-methyl)-2- chloromethylimidazole (106 mg, 0.64 mmol) in acetonitrile (12 ml) was added potassium carbonate (116 mg, 0.84 mmol). The reaction mixture was then stirred at 40C for 18 h. To the reaction mixture was added water (6 mi) and ethyl acetate (10 ml). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2 x 5 ml). The combined organic phases were then dried (MgS04) and concentrated in vacuo. The residue was dissolved in acetonitrile/water (3 mi) and the solution was purified by automated preparative liquid chromatography (Gilson system, 150 x 50 mm, LUNA II C18 10 zm column) using an acetonitrile : water gradient [45: 55 to 95: 5]. The appropriate fractions were concentrated to give the titled compound (98 mg). Experimental MH+ 565.9 ; expected 566.0 ‘H-NMR (CDC13) : 2.88-2. 91 (3H), 3.70-3. 74 (3H), 4.80-5. 03 (2H), 6.09-6. 18 (2H), 6.87-6. 89 (1 H), 6.92-6. 95 (1 H), 7.87-7. 90 (2H)

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

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/90313; (2005); 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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: To a well-stirred solution of compound 1 (10mmol) and triethylamine (0.5mL) in acetone, benzenesulfonyl chloride, 4-toluenesulfonyl chloride or 2-nitrobenzenesulfonyl chloride (10mmol) was added dropwise. The reaction mixture was stirred for 2h at room temperature and left overnight. The solvent was evaporated under reduced pressure. The solid was collected, washed with water, dried. Purification by column chromatography was achieved using ethyl acetate/pet. ether (3:1 ratio) as the mobile phase.4.1.3.2 N-(4-(1H-Benzo[d]imidazol-2-yl)phenyl)-4-methylbenzenesulfonamide (8) Yield: 82%. Mp: 230-232 C, Rf = 0.60 (ethylacetate/pet. ether, 2:1). IR (KBr) numax/cm-1: 3373 (NH aminophenyl); 3061 (CH arom); 2922 (CH aliph); 1610 (C=N); 1596 (C=C arom); 1438 (nuas SO2), 1375 (nus SO2). 1H NMR (DMSO-d6, 500 MHz, delta ppm): 2.30 (s, 3H, CH3); 7.07 (d, 2H, J = 9.2 Hz, H2′, H6′ aminophenyl); 7.34 (m, 2H, H3and H5 tosyl); 7.43 (m, 2H, H2 and H6 tosyl); 7.71 (m, 2H, H5, H6 benzimidazole); 7.84 (m, 2H, H4, H7 benzimidazole); 8.01 (d, 2H, J = 9.2 Hz, H3′, H5′ aminophenyl); 10.91 (s, 1H, NH sulfonamide, D2O exchangeable). 12.75, (s, 1H, NH, benzimidazole, D2O exchangeable). MS, m/z (%):363 (M+, 14%); 347 (50%); 208 (100%). Anal. Calcd for C20H17N3O2S (FW: 363): C, 66.10; H, 4.71; N, 11.56; S, 8.82. Found: C, 66.42; H, 4.95; N, 11.14; S, 8.33.

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 2963-77-1.

Reference:
Article; Galal, Shadia A.; Khattab, Muhammad; Andreadaki, Fotini; Chrysina, Evangelia D.; Praly, Jean-Pierre; Ragab, Fatma A.F.; El Diwani, Hoda I.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5423 – 5430;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144690-33-5, 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. 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 236.0 g (50.3 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)-phenyl]phenyl}-methyl imidazole-5-carboxylate (Va) and 3.0 g (75.4 mmol) of NaOH were suspended in 413 ml dimethylacetamide. The suspension was then stirred at room temperature for 20 h and after that 6.9 g (50.3 mmol) of K2CO3, were added. The mixture was cooled to 0 C. and solution of 15.4 g (70.4 mmol) 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolene in 39 ml of dimethylacetamide were slowly added. The mixture was slowly heated to 50 C. and stirred at this temperature for 2 h. After esterification was completed, the mixture was cooled to 10 C. and poured into a mixture of 625 ml of ethyl acetate and 625 ml of 10% NaCl, and stirred at 25 C. for 15 min. The phases were separated and organic phase was washed 2× with 500 ml of 10% NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated up to ½ (approximately 270 g) at reduced pressure.To the resulting solution, 80 ml of ethanol and 8.3 ml (100 mmol) of conc. HCl were added and stirred at 24-26 C. for 3 h. To the cooled mixture 600 ml of water was added and pH of the suspension was estimated to 5 by addition of 5 M NaOH. The phases were stirred for 15 min and separated. Water phase was reextracted with 150 ml of ethyl acetate. Collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. 560 ml of ethyl acetate were added and the mixture was evaporated again. After that, 300 ml of ethyl acetate were added and the mixture was cooled to 20 C. and stirred for 1 h, filtered off and washed with 20 ml of fresh ethyl acetate. The yield of the product (I) was 21 g (75%).

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, Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KRKA; US2009/131680; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-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 33468-69-8, Recommanded Product: 33468-69-8

Production Example 58A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.18 g of 4-(trifluoromethyl)-lH-imidazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.40 g of 2-{3-[4-(trifluoromethyl)imidazole-l-yl]pyridin-4-yl}-5-(trifluoromethyl)benzoxazole hereinafter, referred to as “active compound 57”).Active compound 571H-NMR (CDC13) delta: 9.00 (d, J=5.2 Hz, 1H), 8.84 (s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8.06-8.04 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.70 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.52-7.50 (m, 1H)

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; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49222; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

The synthetic route of 7189-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem