Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 10111-08-7, name is Imidazole-2-carboxaldehyde, 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 10111-08-7, COA of Formula: C4H4N2O

To a mixture of sodium hydride (500 mg, 12.5 mmol) in N,N-dimethylformamide (10 mL) was added lH-imidazole-2-carbaldehyde (1.00 g, 10.4 mmol). The reaction mixture was stirred at rt for 1.5 hrs. Then 2-(chloromethoxy)ethyl-trimethyl-silane (2.08 g, 12.5 mmol) was added at 0 C. The reaction mixture was stirred at rt for 16 hrs. On completion, the mixture was quenched by water (50 mL) and extracted with ethyl acetate (3 X 100 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (petroleum ether: ethyl acetate = 5: 1) to give the title compound. LH MR (400 MHz, CDC13) delta = 9.85 (s, 1H), 7.39 (s, 1H), 7.35 (s, 1H), 5.80 (s, 2H), 3.59 (t, J = 8.4 Hz, 2H), 0.92 – 1.00 (m, 2H), 0.003 (s, 9H).

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

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (358 pag.)WO2017/156165; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, 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 137049-00-4 as follows.

5. SYNTHESIS OF (-)-2,4-DICHLORO-7V-(1 ‘-(l-METHYL-li-iMiDAzoL-4-YLSULFONYL)-2,3-DIHYDRO [INDENE- 1 ,4 ‘-PIPERIDINE] -2-YL)BENZAMIDE, 7B; [00235] To a solution of 6b (440 mg, 1.07 mmol) and DIPEA (384 muL, 2.14 mmol) in CH2Cl2 (12 mL) was added 1 -methyl- lH-imidazole-4-sulfonyl chloride (194 mg, 1.07 mmol). The reaction was stirred for 18 h. To the reaction mixture was added hexanes (4 mL) and isolated the white ppt by vacuum filtration to afford 7b (501 mg, 92%); Eta-nmr (400 MHz, CDCl3) delta 7.53 (s, IH), 7.46-7.44 (m, 2H), 7.37 (d, J= 2.0 Hz, IH), 7.30-7.18 (m, 5H), 6.06 (d, J= 10.0 Hz, IH), 4.91 (dd, J= 9.0, 6.0 Hz, IH), 3.88-3.72 (m, 5H), 3.43 (dd, J= 17.0, 6.0 Hz, IH), 3.14 (d, J = 12.5, 5.0 Hz, IH), 3.03 (td, J= 12.0, 3.0 Hz, IH), 2.81 (d, J= 16.0 Hz, IH), 2.27-2.21 (m, IH), 1.94 (d, J= 13.5 Hz, IH), 1.81-1.71 (m, 2H), 1.49 (dd, J= 35.0, 6.5 Hz, IH); m/z 519.1.

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; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; CONN, Jeffrey, P.; WILLIAMS, Richard; JONES, Carrie, K.; SHEFFLER, Douglas, J.; WO2010/102003; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20075-26-7, A common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, molecular formula is C5H8N2O, 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.

The title compound was prepared as follows. To a solution of 1-methoxymethyl- imidazole (216 mg, 1. 95 MMOL) in dry THF (20 mi) AT-78 C was added slowly a solution of t- butyllithium (2. 4 ml of 1. 7 M in THF). After 20 minutes, ZNCI2 (663 mg, 4. 86 MMOL) was added, the mixture was allowed to warm to room temperature and stirred for another 60 min. 1- 4-AMINO-2- [1- (6-CHLORO-PYRIDINE-3-SULFONYL)-PIPERIDIN-4-YLAMINO]-THIAZOL-5-YL}-1-PHENYL- methanone (Example F21 ; 200 mg, 0. 390 MMOL) AND TETRAKIS (TRIPHENYLPHOSPHINO) PALLADIUM (0) (Pd (Ph3P) 4 ; 12 mg, 0. 013 MMOL) were added and the mixture REFLUXED under argon for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with 0. 1 NAOH, dried over MGS04, filtered, and concentrated. The resultant solid was dissolved in a solution of 38% HCI (10 ML), ethanol (15 MI), and H20 (15 ml) and REFLUXED for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with sat. NaHCO3, dried over MGS04, filtered, concentrated, and purified via preparative HPLC. The concentrate from fractions was dissolved in EtOAc, washed with sat NAHC03, dried over MGS04, filtered, and concentrated. The resultant solid was placed in acetonitrile (30 ML), water (90 ML), and 38% HCI (0. 5 mL) and evaporated to give 26 mg of white powder in 11 % yield. ‘H NMR (CD30D) : 8 9. 13 (d1H, J=2. 5 Hz), 8. 44 (dd, 1H, J=2. 5, 8. 3 Hz), 8. 23 (d, 1H, J=8. 3 Hz), 7. 78 (s, 2H), 7. 50-7. 40 (m, 1H), 7. 08-6. 97 (m, 2H), 4. 02-3. 90 (m, 3H), 2. 98-2. 87 (m, 2H), 2. 37-2. 13 (m, 2H), 1. 96-1. 78 (m, 2H). ESIMS (MH+) : 546. Anal. Calcd for C23H2, F2N703S2 O 2. 4 HCI * 1. 0 H2O # 0. 5 EtOAc : C, 43. 19 ; H, 4. 26 ; N, 14. 10 ; S, 9. 23. Found : C, 42. 85 ; H, 4. 67 ; N, 14. 50 ; S, 9. 27.

The synthetic route of 20075-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/74283; (2004); 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 17289-20-2 as follows. Computed Properties of C6H8N2O2

EXAMPLE 8 Preparation of 1-methyl-5-hydroxymethylimidazole To a suspension of 1.4 g (0.01 mol) of 1-methyl-5-carbmethoxyimidazole in 5 ml of water is added 0.8 g (0.02 mol) of sodium hydroxide, and the mixture was heated to reflux for 2 hours. To the mixture is added 4 ml of ~37percent aqueous formaldehyde solution, and the resultant mixture is heated at 80-90 for 2 hours. After completion of the reaction, the solvent is stripped off and the residue is extracted with ethyl acetate. The ethyl acetate extract was concentrated to give 1-methyl-5-hydroxymethylimidazole as a solid, m.p. 112¡ã-114¡ã C.

According to the analysis of related databases, 17289-20-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Institute of Science and Technology; US4292431; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1219741-19-1, 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. 1219741-19-1, name is 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-chloro- 5 -iodo-2-methanesulfonyl-l H-benzoimidazole (1.53g, 4.3 mmol) in DMF (21 ml) at 0C was added sodium hydride (60% dispersion in mineral oil, 190 mg, 4.7 mmol). After 15 minutes, the reaction was warmed to rt and stirred for 1 hour. The mixture was then cooled to 0 0C and 4-bromomethyl-birhohenyl (1.2 g, 4.7 mmol) was slowly added. The mixture was then warmed to rt and stirred overnight. The volatiles were removed on a rotary evaporator and the residue was partitioned between EtOAc and half-saturated ammonium chloride. The aqueous layer was extracted a second time and the organic extracts were combined. The combined EtOAc extracts were washed with H2O5 brine, and then dried with MgSO4. The crude oil obtained upon rotary evaporation was triturated in Et2O and filtered to yield the title compound as a beige solid.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 930-62-1,Some common heterocyclic compound, 930-62-1, name is 2,4-Dimethylimidazole, molecular formula is C5H8N2, 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 of 2,4-dimethylimidazole (8-40 g; 87.38 mmol) in dry DMF (250 mL) was treated with potassium tert-butoxide (9.806 g; 87.38 mmol). The mixture was stirred at ambient temperature until homogenous. tert-Butyl bromoacetate (15.29 mL; 104.9 mmol) was added dropwise. The solution was stirred for 15 min, then diluted with isopropyl acetate (400 mL) and washed with pH7 phosphate buffer (3¡Á250 mL). The organic was dried over MgSO4, filtered and evaporated to an oil. The crude product (consisting of the two title compounds) was chromatographed over silica gel (0% to 10% MeOH/CH2Cl2; linear gradient). All fractions containing the two products were combined. The residue was rechromatographed on Chiralcel OD stationary phase (Daicel Chemical Industries Ltd., Chiralcel Technologies Inc.; 10% ethanol/heptane; lambda=220 nM). The more mobile 2,5 isomer and less mobile 2,4 isomer were obtained.500 MHz 1H NMR (CDCl3): (2,4 isomer) delta 6.49 (s, 1H), 4.39 (s, 2H), 2.24 (s, 3H), 2.17 (s, 3H), 1.42 (s, 9H); (2,5 isomer) delta 6.67 (s, 1H), 4.41 (s, 2H), 2.35 (s, 3H), 2.15 (s, 3H), 1.48 (s, 9H).

The synthetic route of 930-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
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. 10111-08-7, name is Imidazole-2-carboxaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: Imidazole-2-carboxaldehyde

General Procedure E; (according literature reference Bioorg. Med. Chem. 2005, 13 , 363-386) [00126] l-ethyl-lH-imidazole-2-carbaldehyde[00127] To a heterogeneous mixture of imidazole-2-carboxaldehyde (500 mg, 5.20 mmol, 1 eq) and potassium carbonate (863 mg, 6.24 mmol, 1.2 eq) in N,N-dimethylformamide (5.0 mL) was added iodoethane (0.499 mL, 6.24 mmol, 1.2 eq). The reaction mixture was heated to 50 0C for 5 hours then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated and washed successively with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give crude l-ethyl-lH-imidazole-2-carbaldehyde as a mixture with N,N- dimethylformamide (-1: 1) which was used without further purification. [00128]

The synthetic route of 10111-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2009/67233; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. COA of Formula: C8H6F2N2

A mixture of 2-difluoromethyl-lH-benzimidazole (2.22 g), 2,4-dichloro- 6-morpholinopyrimidine (2.81 g), potassium carbonate (6.63 g) and DMF (50 ml) was stirred under nitrogen and heated to 90C for 16 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1 : 1 mixture of isohexane and diethyl ether. There was thus obtained 4-chloro-2-(2-difiuoromethylbenzimidazol- 1 -yl)-6-morpholinopyrimidine (3.17 g); NMR Spectrum: (DMSOd6) 3.75 (s, 8eta), 7.09 (s, IH), 7.45-7.47 (m, IH), 7.50-7.54 (m, IH), 7.57-7.83 (t, IH), 7.87 (d, IH), 8.31 (d, IH); Mass Spectrum: M+H+ 366.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 705-09-9, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32072; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

The synthetic route of 1H-Benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1632-83-3, The chemical industry reduces the impact on the environment during synthesis 1632-83-3, name is 1-Methylbenzimidazole, I believe this compound will play a more active role in future production and life.

General procedure: A solution of copper(II) acetate (7.3 mg, 0.04 mmol), triphenylphosphine (21 mg, 0.08 mmol), benzothiazole (1, 22 muL, 0.2 mmol), N-methylaniline 2a (0.088 mL, 0.8 mmol) and NaOAc (66 mg, 0.8 mmol) in 1.0 mL of xylene was stirred at 140 C for 20 h under O2. After cooling to room temperature, the mixture was passed through a Celite pad, which was washed with chloroform repeatedly. The filtrate was washed with water three times. The organic layer was concentrated under reduced pressure to leave a crude oil, which was purified by column chromatography on silica gel to afford 39 mg of 3a as a colourless oil (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, 1-Methylbenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mitsuda, Shinobu; Fujiwara, Taiki; Kimigafukuro, Katsuyoshi; Monguchi, Daiki; Mori, Atsunori; Tetrahedron; vol. 68; 18; (2012); p. 3585 – 3590;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem