Author: Jessica.F

Related Products of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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 tert-butyl (6-(3-((6-amino-,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate (67 mg, 0.12 mmol) in DCM (2 ml) were added 1-methyl-1H-imidazole-4-sulfonyl chloride (46 mg, 0.26 mmol) and pyridine (100 muL, 1.24 mmol), the sulfonyl chloride was not fully soluble, so dioxanes (2 mL) was added and the resulting mixture was stirred at 60 C. for 21 h. The resulting suspension was concentrated, then purified by silica-gel chromatography (1:5-1:1 EtOAc/hexanes then 100% EtOAc) and dried to give tert-butyl (6-(3-((1,3-dimethyl-6-(1-methyl-1H-imidazole-4-sulfonamido)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate as a red-colored amorphous solid (58 mg, 68%). MS (ES+) C33H46N6O8S requires: 686. found 687 [M+H]+. 1H NMR (600 MHz, CDCl3) delta: 7.97 (br-s, 1H), 7.60 (s, 1H, overlapped with CHCl3), 7.35 (s, 1H), 7.31 (s, 1H), 7.20 (s, 1H), 6.57 (s, 1H), 6.14 (s, 1H), 5.77 (br-s, 1H), 5.72 (br-s, 1H), 3.86 (t, J=6.4 Hz, 2H), 3.83 (t, J=6.5 Hz, 2H), 3.62 (s, 3H), 3.45 (s, 3H), 3.31 (s, 3H), 3.12 (br-t, J=6.3 Hz, 2H), 1.76 (m, 4H), 1.51 (m, 2H), 1.46 (m, 2H), 1.44 (s, 9H), 1.37 (m, 2H), 1.01 (t, J=7.3 Hz, 3H).

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; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of cucurbiturils was prepared by preparing a solution of glycoluril (111 g, 0.781 moles) in water (123 ml, 6.833 moles) under stirring. Sulphuric acid (125 mL, 2.34 moles) and formalin (116 mL, 1.56 moles) were added to the solution of glycoluril and the mixture heated to 100C and held under stirring for 14 hours. The reaction mixture was then cooled to room temperature over a 3 hour time period and the cooled reaction mixture precipitated into methanol (1000 ml). The precipitate was filtered, slurried with methanol (1000 ml), filtered again and dried. (0047) The mixture was determined using nuclear magnetic resonance (1H NMR) imaging to be 20- 25 percent by weight CB[5], 45-55 percent by weight CB[6], 20-25 percent by weight of CB[7], 5-8 percent by weight of CB[8], and less than 1 percent by weight CB[9] and higher cucurbiturils, based on the total weight of cucurbituril in the mixture

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, Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; CHEESMAN, Ben; ZHANG, Jing; (20 pag.)WO2018/178647; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 60-56-0,Some common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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 mixing of thiols (1 mmol), sodium hydroxide(1.1 mmol), water (0.5 mL) and methanol (3 mL) were stirred in room temperature. After 30 min,compound 2 (1.1 mmol) in 5 mL CH2Cl2 was added dropwise to the mixture for 36 h-42 h. The mixturewas concentrated in vacuo. The residue was dissolved by CH2Cl2. The solution was extracted threetimes with water. The organic phase was dried overnight with anhydrous sodium sulfate. The solventwas concentrated in vacuo to give crude products. The crude product was purified by silica gelcolumn chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2(3H)-thione, its application will become more common.

Reference:
Article; Yi, Yunpeng; Fu, Yunxing; Dong, Pengcheng; Qin, Wenwen; Liu, Yu; Liang, Jiangping; Shang, Ruofeng; Molecules; vol. 22; 6; (2017);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

4-(Trifluoromethyl)-1 /-/-imidazole (640 mg, 4.7 mmol) was stirred in dry THF (30 ml_) at room temperature under nitrogen. Lithium hexamethyldisilazide (1 M in THF, 4.2 ml_, 4.2 mmol) was added. After 45 minutes, a solution of Intermediate (1-13b) (1.42 g, 4.7 mmol) in dry THF (20 ml_) was added. The reaction was stirred for 12 hours. The reaction was quenched with saturated ammonium chloride and diluted with brine and ethyl acetate. Enough water was added to dissolve the precipitated salts. The aqueous layer was extracted with ethyl acetate, and the combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 100% heptane gradient to 80% ethyl acetate/heptane. The appropriate fractions were combined, evaporated, and dried under high vacuum to afford (1-13c) as a yellow oil (689 mg, 2.39 mmol, 57%). m/z 289.2 (M+H)+.

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

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/29461; (2010); 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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 38993-84-9

Add thionyl chloride (4.00 ml, 53.8 mmol) to a solution of (3-methyl-3H- imidazol-4-yl)-methanol (4.0 g, 35.7 mmol) in dichloroethane (30 mL) and stir at room temperature for 18 h. Concentrate the reaction mixture and add ether to the residue. Sonicate for 5 min, filter, and dry to give the title compound (5.8 g, 98percent). MS (ES+) 131 (M+l)+. 1H NMR (400 MHz, DMSO-d6): delta 14.99 (s, 1H), 9.18 (s, 1H), 7.75 (s, 1H), 5.00 (s, 2H), 3.85 (s, 3H).

According to the analysis of related databases, 38993-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/66174; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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. COA of Formula: C5H6N2O

A mixture of i-methyMH-imidazole-4-carbaldehyde (0.50 g), N- bromosuccinimide (0.89 g) and chloroform (7.0 ml_) was heated at reflux for 2 hours. The mixture was cooled to O0C, diluted with saturated aqueous sodium carbonate solution (10 ml_) and extracted with dichloromethane. The combined organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 7:10 by volume) to afford the title compound as a white solid (0.37 g).1H NMR (CDCl3): delta 3.70 (s, 3H), 7.66 (s, 1 H), 9.89 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17289-26-8, its application will become more common.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2009/77728; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, molecular formula is C8H12N2O2, 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 3-(1H-imidazol-2-yl)propanoate

(ii) Production of ethyl 3-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]propionate A suspension of 4-[[4-(4-iodobutyl)phenoxy]methyl]-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (6.00 g), ethyl 3-(1H-imidazol-2-yl)propionate (3.83 g) and potassium carbonate (1.58 g) in DMF (100 ml) was stirred at 70C for 23 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with water and saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate) and washed with diethyl ether-hexane to give the titled compound (3.69 g) as a colorless amorphous form.1H-NMR (CDCl3) delta: 1.25 (3H, t, J = 7.2 Hz), 1.59-1.79 (4H, m), 2.59 (2H, t, J = 7.0 Hz), 2.88-2.91 (4H, m), 3.87 (2H, t, J = 7.0 Hz), 4.14 (2H, q, J = 7.2 Hz), 5.02 (2H, d, J = 0.8 Hz), 6.79 (1H, d, J = 1.4 Hz), 6.90-7.06 (6H, m), 7.10 (1H, s), 7.52-7.69 (5H, m). IR (KBr): 1732, 1510, 1325, 1167, 1123, 1067 cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 172499-76-2, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1439178; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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 33543-78-1, Safety of Ethyl 1H-imidazole-2-carboxylate

Ethyl 1H-imidazole-2-carboxylate at 0 C(40.01 g, 285.5 mmol) in a dry THF (600 mL) suspension Sodium hydride (13.82 g, 345.5 mmol, mass fraction 60%) was added.The reaction mixture was stirred at room temperature for 1 hour and then cooled to 0 C.O-(2,4-dinitrophenyl)hydroxylamine (80.00 g, 401.8 mmol) was added portionwise.The reaction system was stirred at room temperature overnight and then diluted in water (600 mL).The resulting mixture was extracted with EA (600 mL×10).The separated organic phase was dried over anhydrous sodium sulfate, filtered and evaporated.The residue obtained is purified by silica gel column chromatography (EA/PE (v/v) = 1/2 to 1/1 to 2/1).The title compound is a brown solid(37.6 g, yield 85%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Xiaobo; Li Minxiong; Zhang Tao; Hu Haiyang; Wu Yanjun; (102 pag.)CN108570048; (2018); A;,
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. 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-5-methoxy-1H-benzo[d]imidazole

Preparation 21 tert-Butyl 2-chloro-5-methoxy-1H-1,3-benzimidazole-1-carboxylate STR66 Di-tert-butyldicarbonate (523 mg) was added to a solution of 2-chloro-5-methoxy-1H-1,3-benzimidazole (364 mg) and dimethylaminopyridine (24 mg) in acetonitrile (4 ml). The reaction mixture was stirred at room temperature for 30 minutes, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluding with a solvent gradient of 90:10 changing to 85:15, by volume, hexane:ethyl acetate to afford tert-butyl 2-chloro-5-methoxy-1H-1,3-benzimidazole-1-carboxylate (470 mg) as an off-white solid, as a 1:1 mixture of regioisomers. 1 H-NMR (CDCl3)delta: 7.80 (0.5H, d), 7.55 (0.5H, d), 7.50 (0.5H, s), 7.15 (0.5H, s), 7.00 (1H, t), 3.85 (3H, s), 1.70 (9H, s).

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 15965-54-5.

Reference:
Patent; Pfizer Inc; US6166011; (2000); A;,
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 7189-69-7 as follows. Recommanded Product: 7189-69-7

To a solution of phenethylamine (34, 0.15mmol) in THF (5mL), triethylamine (0.15mmol) was added. To this mixture, 1,1′-sulfonyldiimidazole (0.15mmol) was added and the reaction mixture was stirred at 60C for 2h. After the completion of the reaction monitored by TLC, water was added and the reaction mixture was extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The obtained intermediate 36 was used for next step without further purification. In the next step, 3-phenylpropylamine (0.15mmol) was dissolved in THF and triethylamine (0.15mmol) was added. To this mixture, 36 was added. The reaction was stirred at 60C for 3h. The reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was quenched with water and the whole mixture was extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was purified by column chromatography to afford the pure product 3. Yield 72%, Pale yellow solid. Rf 0.30 (2: 1 Ethylacetate: Hexane), mp. 135-137C; IR (neat): 3362, 2950, 2822, 1560, 1523, 1345, 1170, 945cm-1. 1H NMR (CDCl3) delta 1.79-1.87 (m, 2H), 2.64 (t, J=8.00Hz, 2H), 2.85 (t, J=7.20Hz, 2H), 2.92-2.97 (m, 2H), 3.28-3.33 (m, 2H), 4.07-4.13 (m, 2H), 7.15-7.33 (m, 10H); 13C NMR (CDCl3) delta 31.13, 32.94, 35.81, 42.68, 44.31, 126.35, 127.04, 128.50, 128.71, 128.97, 128.98, 138.10, 141.04. HRMS Calcd for C17H22N2O2S m/z [M+H] 319.1481, found 319.1507.

According to the analysis of related databases, 7189-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Sharma, Niti; Boggu, Pulla Reddy; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 379 – 391;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem