Tag: M.W=100-200

1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

Intermediate 14: step b (1-methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone A solution of EtMgBr (3.0 M in diethylether, 15.1 niL, 45.2 mmol) was added dropwise, to a solution of 5-bromo-l -methyl- 1H- imidazole (7.28 g, 45.2 mmol) in dry DCM (40 ml.) at 0 C and stirred for 10 minutes. The mixture was then stirred at room temperature for 30 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (8.45 g, 37.7 mmol, Intermediate 14: step a) dissolved in 22 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 18 hours. Water was added to the suspension followed by 6 M aqueous HC1 slowly to neutralize the mixture (pH = 6-7). More DCM was added and layers separated. The organic layer was dried over MgSC>4, filtered and concentrated. Et20 was added, the slurry sonicated, and precipitates were filtered and dried to provide the title compound.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Complexes 1-4 were prepared in a Schlenk tubecontaining 30 mL of CH2Cl2 (deaerated previously).Then, 0.24 mmol of the ligand and 32 muL of triethylaminewas added to the Schlenk. Afterwards, 0.11 mmol of theprecursor [RuCl2(dppb)(PPh3)] was added and the solutionwas stirred for 12 h under Ar atmosphere. The final yellowsolutions were concentrated to about 2 mL and diethyl etherwas added, to obtain yellow precipitates. The solids werefltered off, well rinsed with water (5 ¡Á 5 mL) and diethylether (3 ¡Á 5 mL) and dried in vacuo.

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:
Article; Batista, Alzir A.; Castellano, Eduardo E.; Castelli, Silvia; Cominetti, Marcia R.; Deflon, Victor M.; Desideri, Alessandro; da Silva, Monize M.; de Camargo, Mariana S.; de Grandis, Rone A.; Journal of the Brazilian Chemical Society; vol. 31; 3; (2020); p. 536 – 549;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

570-22-9, 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of imidazole-4,5-dicarboxylic acid (400 mg, 2.56 mmol) in 5 mL of toluene was added 1.12 mL of thionyl chloride (15.38 mmol) and 0.1 mL of DMF at rt. The reaction mixture was stirred at 90 C for 16 h. Then 5 mL of DCM was added to the suspension and the solvent was removed by evaporation. This process was repeated twice. The resulting acid chloride was dissolved in 10 mL of DCM and cooled to 0 C. Phenol (2.82 mmol) in 5 mL of DCM was added and the resulting solution was stirred at 0 C for 1 h. Then the solid product was collected by vacuum filtration, washed with 10 mL of DCM twice, and dried under vacuum to yield 0.632 g of crude product 17 (83.6 % over two steps) as a tan solid. 1H NMR (300Hz, DMSO) delta 9.12 (s, 2H), 7.52-7.56 (m, 4H), 7.34-7.40 (m, 6H); ESI-MS: 429 [M+1]+

The synthetic route of 1H-Imidazole-4,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Serrao, Erik; Xu, Zhong-Liang; Debnath, Bikash; Christ, Frauke; Debyser, Zeger; Long, Ya-Qiu; Neamati, Nouri; Bioorganic and Medicinal Chemistry; vol. 21; 19; (2013); p. 5963 – 5972;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4857-06-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4857-06-1 name is 2-Chloro-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The N-methyl-1H-benzo[d]imidazol-2-amine, used as starting material, can be prepared as follows:2-Chloro-1H-benzo[d]imidazole (20 g, 131.08 mmol) was charged to high pressure autoclave PV10832 (Hastelloy 450 ml) with methylamine (260 mL, 131.08 mmol) and sealed on its trolley and the resulting solution heated to 160 C. in high pressure blast cell 60 for 16 hours. The pressure in the autoclave reached 11 bar. The solvent was removed under reduced pressure to afford a brown oil. EtOH was added and the solvent again removed to afford a brown foam. The foam was dissolved in a minimum of hot acetone. This was then allowed to cool. The resultant solid was filtered affording N-methyl-1H-benzo[d]imidazol-2-amine (9.91 g, 51%); 1H NMR (400 MHz, DMSO-d6) 2.83 (3H, s), 6.87-7.00 (2H, m), 7.05-7.25 (2H, m), 7.49 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 98873-55-3

A 10 mL schienk tube was charged with powdered KOH (116 mg, 2.07 mmol), DMSO (1 mL), purged with Argon and cooled at 18CC with a water bath. A solution of 2-imidazol-1- ylacetonitrile (104 mg, 0.97 mmol) and CS2 (117 pL, 1.9408 mmol) in DMSO (500 pL) is then added slowly to give an orange mixture. The cooling bath is removed and the reaction is stirred at room temperature for 30 minutes. Then a solution of freshly prepared (2-bromo-5-fluoro-indan-1-yl)methanesulfonate (step 3) in DMSO is added dropwise. After 30 minutes stirring at room temperature, the reaction is poured into H20 (20 mL). The aqueous phase is extracted with AcOEt (3 x 5 mL), the combined organic phases were washed with H20 (10 mL), brine (10 mL), dried with Mg504, filtered and evaporated to give a crude pale yellow residue. Purification by chromatography on silica gel (heptanes/ethylacetate 2:1-1:3) afford2-(6-fluoro-4,8b-dihydro-3aH-indeno[1 ,2-d][1 ,3]dithiol-2-ylidene)-2-imidazol-1 -yl-acetonitrile as an inseparable (2:1) mixture of E/Z-isomers.

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, 98873-55-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien, Daniel; BONVALOT, Damien; JEANMART, Stephane, Andre, Marie; WO2015/11194; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below.

l-Beiuothiazol-6->l-imidazolidm-2-one lL-_84b: 15Umg, 0.6849mmol) was reacted with 5>br¡ãnkappa>-. -methyl- U l-imidazole (12l.3mg, O.753mmol).1.4’diox?nie (SmL). copper iodide ( 12.99mg, 0.0684mmol). trans N.N’-diim’th^l-cyclohexane- 1 ,2-diamine (2l>.176mg.0.20Smiotanol) and potassium phosphate (435.0 ling, 2.05mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOl ) in CIlCI.? ) afforded 85mg of the product (4l.o4% >ield).1I I NMR (300 MH/. CDCh): o 8.9 (?, HIV 8.35 (d.1 M).8. l(d. III).7.7 (dd. III). 7.5-7.4(brs, IH),7.0(brs, HH.4.1 (t, 211), 3.9 (t.211), 3.6 (s.311).I CMS: 100%,inV 299.8 (M+ 1)HPLC: 98.52%

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; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; SENGUPTA, Saumitra; WO2010/149755; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, A common compound: 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

:[0172]A suspension of aminoguanidinium nitrate (150 mg, 1.09 mmol) and K2CO3(150 mg, 1.09 mmol) in N, N-dimethylformamide (DMF) (3 mL) was stirred at room temperature for 1 h. A solution of 1H-benzo [d] imidazole-2-carboxylic acid (162 mg, 1.0mmol) in N, N-dimethylformamide (DMF) (5 mL) was treated with N, N’-carbonyldiimidazole (CDI) (180 mg, 1.1 mmol) at 0. The solution was stirred at room temperature for 1 h. Then it was added to the suspension. The resulting mixture was stirred at room temperature for 3 h , then it was heated to 100 for 3 h. The mixture was cooled to room temperature, filtered and concentrated to give crude 3- (1H-benzo [d] imidazol-2-yl) -1H-1, 2, 4-triazol-5-amine (Intermediate 1) as white solid (290mg, 40purity) which was used in next step directly. Mass spectrum (ESI) m/z calc. for C9H8N6[M+H]+201.08, found 201.20.

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-Benzimidazole-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; HUANG, Niu; QI, Xiangbing; WANG, Yanli; SUN, Yuze; (56 pag.)WO2017/152842; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, The chemical industry reduces the impact on the environment during synthesis 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-benzo[d]imidazol-2(3H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, A common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

A solution of 2-(3 ,4-dimethoxyphenyl)-3 -i sopropyl -5 -(piperidin-4-yl)- 1 H-indole, HC1 (25 mg, 0.060 mmol) in DCM (0.5 mL) was neutralized by adding triethylamine drop wise (checked by pH paper). The solution was added to a vial containing i-methyliH-imidazole-5-carbaldehyde (9.95 mg, 0.090 mmol), acetic acid (0.01 ml, 0.175 mmol) at room temperature. The mixture was stirred at room temperature for 16 h. Sodium triacetoxyborohydride (19.15 mg, 0.090 mmol) was added to the reaction mixture and the mixture was stirred for another 6 h at room temperature. The reaction mixture was purified by reverse phase prep LCMS to provide 2-(3,4-dimethoxyphenyl)-3-isopropyl-5-(1 -((1 -methyl- 1H-imidazol-5-yl)methyl)piperidin-4-yl)- 1H-indole (1.27 mg, 4.34% yield,97.2% purity) as a pale solid. LC retention time = 1.734 mm [E]. MS (E) m/z: 473.2 (M+H).

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; HAQUE, Tasir S.; POSS, Michael A.; LOMBARDO, Louis J.; MACOR, John E.; PASUNOORI, Laxman; KUMAR, Sreekantha Ratna; (296 pag.)WO2018/26620; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

492-98-8, These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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.

Synthetic example 7: yl)pyridin-2-amine)7A mixture of 1H,17-/-2,2′-biimidazole (840 mg, 6.3 mmol), A/-(4-bromophenyl)-A/- (pyridin-2-yl)pyridin-2-amine (6.59 g, 20.3 mmol) and Cs2C03 (10.14 g, 31.2 mmol) in DMF (70 mL) was degassed (N2 bubbling, 15 min). Cu20 (360 mg, 2.5 mmol) was added and the mixture was heated (140 “C, 72h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H20 and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc/CH2CI2/MeOH 35:60:5 then 32:60:8 then 28:60:12) to give Lambda/,Lambda ¡¤(4,4′-(1Eta, 1 “H^’-biimidazoie-l , 1 ‘-diyl)bis(4, 1 -phenylene))bis(A/-(pyridin- 2-yl)pyridin-2-amine) (1.36 g, 35%) as a colourless solid. A portion of this material was further purified firstly, by recrystallisation (CH2CI2/EtOAc/petrol) and then by distillation (sublimation apparatus 260 C, 10~6 mBar): m.p. 218 – 222 C (DSC); ‘H NMR (CDCI3l 400 MHz) delta 6.75 – 6.80 (m, 4H), 6.90 (ddd, J 0.8, 4.9, 7.3 Hz, 4H), 6.93 – 7.00 (m, 8H), 7.09 (d, J 1.0 Hz, 2H), 7.26 (s, 2H), 7.52 (ddd, J 2.0, 7.3, 8.3 Hz, 4H), 8.24 (ddd, J 0.7, 1.9, 4.9 Hz, 4H); 13C NMR (CDCI3, 100 MHz) delta 117.0, 118.6, 121.1 , 125.2, 127.5, 130.0, 133.7, 137.6, 144.3, 148.6, 157.7; HRMS (El) m/z 623.2420 C38H27 10 [M – H]+’ requires 623.2415.

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 492-98-8.

Reference:
Patent; COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; MACDONALD, James Matthew; BOWN, Mark; UENO, Kazunori; WEBER, Karl Peter; O’CONNELL, Jenny Lee; HIRAI, Tadahiko; WO2012/51666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem