Tag: M.W=100-200

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. 50995-95-4, name is 2-Propylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 50995-95-4

Preparation of 6-(2-propylimidazol-l -vDpurine. A suspension of 2′,3′,5′-tri-O-acetylinosine (1.58 g, 4.0 mmol), 2- propylimidazole (1.60 g, 14.4 mmol), Ph3P (2.58 g, 9.6 mmol), I2 (2.14 g, 8.32 mmol), and EtN(Z-Pr)2 (3.6 mL, 2.67 g, 20.2 mmol) in dried toluene (40 mL) was stirred at 95 C for 4 h. Volatiles were evaporated in vacuo, and the residue was extracted with boiling EtOAc. The combined extracts were evaporated to dryness, and the residue was chromatographed (CH2Cl2ZMeOH, 1 :40) to give a solid contaminated with Ph3PO. This material was dissolved in AcOH (160 mL), and AcCl (2.2 mL, 2.43 g, 31 mmol) was added. The solution was stirred at 65 C overnight, and volatiles were evaporated in vacuo. The residue was dissolved in CH2Cl2 and extracted with 0.1 N NaOHZH2O. The aqueous layer was washed (CH2Cl2), and precipitation with CO2 followed by filtration and thorough washing (H2O) gave a solid (0.66 g, 72%). This material was dissolved in MeOH and decolorized with charcoal. Recrystallization (MeOH) gave 6-(2-propylimidazol-l- yl)purine as a colorless solid: mp 242.5-243.5 C; UV (MeOH) max 278 nm (epsilon 13 700), min 235 nm (epsilon 5000); 1H NMR (300 MHz5 DMSO-^6) delta 13.90 (br s, IH), 8.86 (s, IH), 8.69 (s, IH), 8.36 (s, IH), 7.07 (d, J= 1.5 Hz, IH), 3.18 (t, J= 7.3 Hz, 2H), 1.72 (sext, J= 7.3 Hz, 2H), 0.93 (t, J= 7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3) delta 155.5, 152.0, 149.8, 146.9, 145.8, 128.5, 123.6, 121.4, 32.2, 21.5, 14.5; HRMS m/z 228.1109 (M+ [C11H12N6] = 228.1123). Anal. Calcd for CnH12N6: C, 57.88; H, 5.30; N, 36.82. Found: C, 58.09; H, 5.19; N, 37.00.

The synthetic route of 50995-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRIGHAM YOUNG UNIVERSITY, TRANSFER TECHNOLOGY OFFICE; WO2006/138396; (2006); A2;,
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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H5ClN2O2S

To a precooled (0 C) solution of intermediate 2.66 (18 mg, 0.074 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) was added 1-methyl-1H- imidazole-4-sulfonyl chloride (20. mg, 0.11 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 18 h, then diluted with wet DMSO (1 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (6.3 mg, 22% yield).1H NMR (500 MHz, Acetonitrile-d3) d 8.56 (s, 1H), 7.69 (s, 1H), 7.66 (dd, J = 11.8, 2.4 Hz, 1H), 7.59 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.21 (dd, J = 8.7, 2.1 Hz, 1H), 3.72 (s, 3H), 3.63 (dd, J = 10.4, 7.9 Hz, 1H), 3.50- 3.40 (m, 2H), 3.40- 3.32 (m, 1H), 3.00 (p, J = 7.6 Hz, 1H), 2.14- 1.96 (m, 2H); AMM 409.0521 (ESI) m/z [calc for C15H16ClFN4O3SNa (M+Na)+ 409.0513].

According to the analysis of related databases, 137049-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-89-2, These common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, 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 4-iomethyl-1H-imidazole (970 mg, 545 mmoles) in DMF (10 mL) is added NaH 60% dispersion inmineral oil (220 mg, 5.5 mmoles). The reaction mixture isheated at 50 C. for 1 h, then 2-bromoethylbenzene (781 f.LL,5.5 mmoles) and a catalytic quantity oftetrabutylammoniumbromide are added to the mixture. The reaction mixture is50 then heated at 80 C. for 5 hours. Half-saturated ammoniumchloride solution is added, and the aqueous phase is extractedthree times with Et20. The organic phase is washed withwater, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (heptane:AcOEt)as eluentwithagradientfrom (95:5)to (60:40)to give4-iodo-1-phenethyl-imidazole and 5-iodo-1-phenethyl-imidazole.4-iodo-1-phenethy 1-imidazole1H NMR: 7.38-7.15 (m, 4H), 7.10-6.96 (m, 2H), 6.93 (s,lH), 4.14 (t, J=8.5 Hz, 2H), 3.04 (t, J=8.5 Hz, 2H).5-iodo-1-phenethyl-imidazole1H NMR: 7.41 (s, lH), 7.36-7.18 (m, 3H), 7.15-7.00 (m,3H), 4.15 (t, J=8.6 Hz, 2H), 3.04 (t, J=8.6 Hz, 2H).

Statistics shows that 5-Iodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-89-2.

Reference:
Patent; BIOPROJET; Berrebi-Bertrand, Isabelle; Billot, Xavier; Calmels, Thierry; Capet, Marc; Krief, Stephane; Labeeuw, Olivier; Lecomte, Jeanne-Marie; Levoin, Nicolas; Ligneau, Xavier; Robert, Philippe; Schwartz, Jean-Charles; (73 pag.)US9255101; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Imidazole-2-carboxylic acid ethyl ester 1 (100 mg, 0.71 mmol) was dissolved in 10 ml of THF, sodium hydride (43 mg, 1.78 mmol) was slowly added under an ice bath for activation for 1 h, and iodomethane (507 mg, 3.57 mmol) was added,After the addition, the reaction was performed at room temperature for 1h. TLC detection reaction is complete,Stop the reaction,Concentrate under reduced pressure to remove the solvent,Add water to dissolve,Ethyl acetate extraction (3×20ml),Combine organic layers,Wash with saturated saline,Dry over anhydrous sodium sulfate and filter,Concentrate to get crude product.Purified by column chromatography (PE:EA=1:1) to obtain yellow oily liquid,Compound 1-methyl-1H-imidazole-2-carboxylic acid ethyl ester 1b(98 mg, yield 89%).

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 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan University; Li Guobo; Wang Zhenling; (40 pag.)CN111187218; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-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 89830-98-8, Quality Control of 5-Cyclopropyl-1H-imidazole

[00400] A mixture of Example 61f (300 mg, 0.63 mmol), Example 61g (204 mg, 1.89 mmol), 8- quinoline (36 mg, 0.25 mmol), Cs2C03(411 mg, 1.26 mmol) and Cu20 (36 mg, 0.25 mmol)in BuCN (5 mL) was stirred at 120°C for 16 h under N2. Then the solution was filtrated and purified by Prep-HPLC, followed by Prep-TLC (DCM/MeOH= 20/1) to give thedesired product Example 61 (6.6 mg, yield 2percent) as a white solid. LCMS [M+l] + = 456.0. NMR (400 MHz, DMSO- 6) delta 11.25 (s, 1H), 8.67 (s, 1H), 8.04 (t, J= 7.9 Hz, 1H), 7.85 (t, J= 7.0 Hz, 2H), 7.76 (s, 1H), 7.62 (s, 1H), 7.34 (s, 1H), 7.10 (s, 1H), 4.37 (m, 2H), 4.25 (t, J= 8.5 Hz, 2H), 2.47 (m, 2H), 2.19 (s, 3H), 1.96 (m, 2H), 1.82 (m, 1H), 0.82-0.73 (m, 2H), 0.69 (d, J= 4.4 Hz, 2H).

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-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); A1;,
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 51605-32-4 as follows. COA of Formula: C7H10N2O2

(5-Methylimidazol-4-yl)methylchloride hydrochloride (14) A paste of ethyl 4-methyl-5-imidazolecarboxylate (37.5 g, 0.243 mol) and a little dry THF was added in portions to a stirred suspension of LiAlH4 (12.0 g, 0.316 mol) in 1.0 L of dry THF under a flow of nitrogen. After refluxing for 4 h, the suspension was cooled in an ice-water bath and the excess LiAlH4 destroyed with successive additions of 12 mL of H2 O, 12 mL of 15percent NaOH, and 45 mL of H2 O. The white suspension was brought to room temperature (2 h) and filtered. After collecting the precipitate, it was digested in hot THF (500 mL), cooled, and filtered again. The total THF filtrate was concentrated in vacuo, the residual orange oil was dissolved in a minimum amount of EtOH, and 500 mL of hot EtOAc:Et2 O (3:2) was added. The solution was chilled yielding 15.0 g (55percent) of (5-methylimidazol-4-yl)methanol as white prisms: mp 138° (lit. 138°). This material (9.6 g, 0.086 mol) was dissolved in 50 mL of conc HCl and heated on a steam bath for 30 min. The acidic mixture was concentrated in vacuo to dryness and the solid dissolved in a minimum amount of EtOH. With the addition of a little dry Et2 O, 14 (8.5 g, 67percent) precipitated as a white powder: mp 236°-237° (lit. 222°).

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Research Corporation; US4432983; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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.

(1) 0.84 g (5 mmol) of 2-difluoromethylbenzimidazole dissolved in DMF (25 ml) was added and reacted with 60% sodium hydride (0.24 g, 6 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 2,4,6-trichloropyrimidine (0.92 g, 5 mmol) dissolved in DMF (25 ml) and stirred at room temperature for 1.5 hours. The reaction solution was poured into water and the resulting precipitates were recrystallized from methanol to obtain 0.98 g (yield: 62%) of 4,6-dichloro-2-(2-difluoromethylbenzimidazol-1-yl)pyrimidine.

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; ZENYAKU KOGYO KABUSHIKI KAISHA; EP1389617; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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 solution containing the product from step 1 (8.36g, 54.2 mmol) and 2-amino-4- nitrophenol (8.74g, 54.2 mmol) in anhydrous THF (200 mL) was allowed to reflux under N2 for 14 hours. The mixture was cooled to RT, filtered, and the precipitate was washed with THF (cold) then dried in vacuo to afford the desired product (9.Og), as a yellow solid. MS (ESI) m/e (M+H4): 180. 1H NMR (DMSO) delta: 7.85 ~ 7.96(m, 3 H), 7.52(d, J = 8.8 Hz, 1H).

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; COBURN, Craig, A.; MCCAULEY, John, A.; LUDMERER, Steven, W.; LIU, Kun; VACCA, Joseph, P.; WU, Hao; HU, Bin; SOLL, Richard; SUN, Fei; WANG, Xinghai; YAN, Man; ZHANG, Chengren; ZHENG, Mingwei; ZHONG, Bin; ZHU, Jian; WO2010/111483; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 51605-32-4,Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

and also, starting from 4-methylimidazole-5-carboxylic acid ethyl ester, 1-(2,6-difluorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 59°-61° (from hexane) and 1-(2,6-difluorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 107°-108° (from toluene/ether), 1-(o-chlorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 74°-76°, and 1-(o-chlorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 100°-104°; and also, starting from imidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 71°-73° (from petroleum ether), 1-(o-chlorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 69°-70° (from ether/hexane) and 1-(o-methylbenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester (oil); and also, starting from 2-methylimidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-2-methylimidazole-4,5-dicarboxylic acid diethyl ester, m.p. 63°-64° (from ether/hexane).

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

Reference:
Patent; Ciba-Geigy Corporation; US4851424; (1989); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8, 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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

A 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- 1 -yl]pyridin-4-yl } -5 -(trifluoromethyl)benzoxazole hereinafter, referred to as “active compound 57”).Active compound 57-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)

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49221; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem