Tag: M.W=100-200

Electric Literature of 1615-14-1, A common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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.

Into a round bottom flask was added 057 (2.331 g, 0.003345 mol), triphenylphosphine (1.14 g, 0.00435 mol) and tetrahydrofuran (13.6 mL, 0.167 mol). The mixture was cooled to O0C under a nitrogen atmosphere. Imidazole ethanol fragment (0.450 g, 0.00401 mol) was added, followed by addition on diethyl azodicarboxylate (0.685 mL, 0.00435 mol). The reaction was allowed to warm slowly to room temperature while stirring. A TLC test revealed an intense product spot together with some unreacted starting material. The reaction was cooled to O0C and an additional 0.2eq of the amine, triphenylphosphine, and DEAD were added. The ice bath was removed and reaction was allowed to warm to room temperature. After 30min, TLC showed the reaction was complete and all starting material was consumed. All solvent was removed under high vacuum. The residue was dissolved in MTBE, the mixture was cooled in an ice bath and some of the triphenyl phosphate was filtered off. The residue was purified on 4Og column, using 0-5%MeOH/DCM. Product fractions containing compound 066 were combined and concentrated down to a residue. Yield: 3.65g(100%).

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; EISAI R & D MANAGEMENT CO., LTD.; WO2009/15368; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 150 mL round-bottomed flask, the benzimidazole compound represented by Formula III (R1 is methyl, R2 is H, R3 is nitro) (0.361 g, 2.04 mmol) was added, and potassium carbonate was used as a base (0.324 g, 2.35 mmol) of acetonitrile as solvent. After stirring at 70C for 30 minutes, the mixture was cooled to room temperature and Compound II (0.400 g, 1.57 mmol) was added to continue the reaction and the temperature was raised to 70C. TLC followed the reaction to completion. After concentration, extraction, column chromatography, drying and other post-treatments, compound IV-3 (0.449 g) was obtained with a yield of 66.1%.

The synthetic route of 2-Methyl-5-nitro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei·lamohan·laao·yadafu; Ge Pala·lawaya; Wang Yanan; Fang Xuejie; (27 pag.)CN107721933; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]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 3752-24-7, name: 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole

A mixture of 4,5,6,7-tetrahydro-1H-benzo[d]imidazole (5.00 g, 40.9 mmol), 90% KOH (3.74 g, 60 mmol) and DMSO (70 mL) was stirred under argon and heated at 40 C for 2 h. After cooling to 10 C, 1-bromohexane (6.3 mL, 45 mmol) was addedin one portion, and the resulting mixture was stirred and heated at 40 C for 4 days.The reaction mixture was poured into ice/water (600 mL), treated with 5 N NaOH(100 mL) and extracted with DCM (2 x 400 mL). The extract was washed with water(300 mL), dried over Na2SO4, and the solvent was removed under reduced pressureto give a residue. Column chromatography of the residue (silica gel, ethylacetate/methanol, 97:3) afforded pure 1-hexyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole (6.54 g, 77% yield).

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; NITTO DENKO CORPORATION; STANISLAW, Rachwal; HU, Yufen; ZHANG, Hongxi; WANG, Peng; (42 pag.)WO2018/191238; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 29043-48-9, A common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, molecular formula is C8H9N3, 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 mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2·2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 × 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3×10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 46006-36-4, 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 46006-36-4 as follows.

3H-Benzoimidazole-4-carboxylic acid[3-(1H-tetrazol-5-yl)-phenyl]-amide (16) 3-(1H-Tetrazol-5-yl)aniline (75 mg, 0.47 mmol), 1H-benzimidazole-4-carboxylic acid (76 mg, 0.47 mmol), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (135 mg, 0.7 mmol), 1-hydroxybenzotriazole (95 mg, 0.7 mmol) and N,N’-diisopropylethylamine (0.17 mL, 0.94 mmol) was stirred in DMF (0.5 mL) at room temperature for 24 h. The reaction mixture is diluted with water (2 mL) and after approximately adjusting the pH to 4 with 1N HCl, the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC to afford the product as a trifluoroacetic acid salt in 5% yield. 1H NMR (DMSO-d6) delta 8.62 (s, 1H), 8.53 (s, 1H), 7.99-8.02 (m, 3H), 7.86 (d, J=8 Hz, 1H), 7.77 (d, J=4 Hz, 1H), 7.62 (t, J=8 Hz, 1H), 7.43 (t, J=8 Hz, 1H), 7.04 (s, 1H); LCMS (ESI) m/z 306 (MH+).

According to the analysis of related databases, 46006-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Chen, Yu; Nichols, Derek; Renslo, Adam R.; Jaishankar, Priyadarshini; Lauterwasser, Erica M. W.; (29 pag.)US9556131; (2017); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2, Computed Properties of C3H3BrN2

(i) Production of (1H-Imidazol-4-yl)-(naphthalen-2-yl)ketone 4-Bromo-1H-imidazole (1.95 g) was dissolved in THF (30 ml), and the solution was cooled to -78 C. To the solution was added a solution of t-butyllithium in pentane (1.7 M; 20 ml). The mixture was stirred at 0 C. for 1.5 h. The mixture was again cooled to -78 C., and a solution of 2-formylnaphthalene (3.32 g) in THF (20 ml) was added. After the temperature was elevated from -78 C. to room temperature, the mixture was stirred at room temperature for 16 h. To the mixture was added an aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography,(eluent, dichloromethane_methanol=10:1). Recrystallization from dichloromethane-methanol gave the titled compound (1.00 g) as a colorless solid. 1H-NMR (CDCl3) delta: 7.53-7.70 (2H, m), 7.84-8.40 (6H, m), 8.53 (1H, s), 10.82 (1H, brs). IR (KBr): 2592, 1640, 1127, 779 cm-1.

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; Takeda Chemical Industries, Ltd.; US6573289; (2003); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

A 20 mL vial was charged with a 1.5 mL of ammonium acetate/acetic acid buffer solution (pH 4) in methanol. To this Example 87D (35.24 mg, 0.109 mmol) was added to form a suspension. lH-benzo[d]imidazole-2-carbaldehyde (23.89 mg, 1.5 eq, 0.164 mmol) and Si-BH3CN (from Silicycle, 0.88mmol/g loading, 371.49 mg) were then added. The vial was capped and placed to stir at 40°C overnight. Upon completion, the crude mixture was filtered, concentrated, and purified by HPLC (see Example 360 for protocols) to provide the title compound as a trifluoroacetic acid salt. lH NMR (400 MHz, pyridine-d5) delta ppm 2.57 (q, J = 4.1, 3.2 Hz, 2H), 2.83 (t, J = 5.7 Hz, 2H), 3.39 (q, J = 2.8 Hz, 2H), 3.71 (s, 3H), 4.17 (s, 2H), 6.61 (s, 1H), 6.64 – 6.67 (m, 1H), 7.09 (dd, J = 9.1, 4.5 Hz, 1H), 7.26 (ddd, J = 9.1, 7.9, 3.2 Hz, 1H), 7.32 (d, J = 4.9 Hz, 1H), 7.34 – 7.39 (m, 2H), 7.49 (dd, J = 8.9, 3.2 Hz, 1H), 7.89 (dd, J = 6.0, 3.2 Hz, 2H), 8.58 (d, J = 5.0 Hz, 1H). MS (ESI+) m/z 454.2 (M+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, 1H-Benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); 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 78581-99-4 as follows. Recommanded Product: 78581-99-4

Step 3: To a stirred mixture of sodium hydride (60% dispersion in mineral oil, 0.144 g, 3.0 mmol) in anhydrousDMF (10 mL) at 0 C under a nitrogen atmosphere was added portionwise 6-difluoro-1H-benzo[d]imidazole (0.475 g,2.0 mmol) from the previous step. The mixture was stirred at 0 C for 5 min. To the mixture was added dropwise asolution of 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (0.32 g, 2.0 mmol) from Step 4 of Example 36 in anhydrousDMF (2 mL). The reaction mixture was allowed to warm to rt and stir for 1 h. The mixture was poured into ice-water andextracted with EtOAc (100 mL 3 2). The combined organic layers were further washed with water (20 mL) then brine(20 mL). The organic layer was separated and dried over Na2SO4, filtered, and concentrated under reduced pressureto afford 6-((5,6-difluoro-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (0.55 g, 76%) as a yellow solid,which was not purified further. 1H NMR (300 MHz, CDCl3) delta 7.97 (s, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.59 (m, 1H), 7.50(s, 1H), 7.24 (m, 1H), 7.02 (m, 1H), 5.40 (s, 2H), 2.78 (s, 3H); LCMS (ESI) m/z 348 (M + H)+.

According to the analysis of related databases, 78581-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6160-65-2, A common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.

Step A: N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide To thiazol-2-amine (2.12 g, 21.17 mmol) in acetonitrile (30 mL) and tetrahydrofuran (5 mL) was added di(lH-imidazol-l-yl)methanethione (4.90 g, 27.5 mmol). The reaction was stirred at 60 C for 5 hours. The reaction was cooled to room temperature and the precipitate was filtered and washed with cold acetonitrile (2 x 15 mL) to afford an orange-brown powder. The product, N-(thiazol-2-yl)-lH- imidazole- l-carbothioamide (3.70 g, 17.60 mmol, 83 % yield), was taken directly to the next step without any further characterization.

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; MCDONALD, Ivar, M.; KING, Dalton; OLSON, Richard, E.; WANG, Nenghui; IWUAGWU, Christiana, I.; ZUSI, Christopher, F.; MACOR, John, E.; WO2011/53292; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 alcohol18(1.0 g, 6.36 mmol) in chloroform (70 mL) was added MnO2(2.76 g, 31.8 mmol) and the mixture was heated to reflux overnight. After cooling, the resulting slurry was filtered through diatomaceous earth and solvent removed in vacuo to yield19(1.5 g, 76%) as a pale yellow solid, mp 112-114 C (lit. [62] mp 114-115 C). deltaH(CDCl3) 9.93 (1H, s, CHO), 7.81 (1H, s, H-4), 4.36 (3H, s, CH3). deltaC(CDCl3) 180.4 (C = O), 148.3 (C-NO2), 139.4 (CH), 132.4 (CH), 35.6 (CH3). LRMS 188.1 (100%, M + CH3OH). These data are in good agreement with literature values [35].

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-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Article; Dickson, Benjamin D.; Wong, Way Wua; Wilson, William R.; Hay, Michael P.; Molecules; vol. 24; 8; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem