Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-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 71759-89-2, Computed Properties of C3H3IN2

General procedure: Method A: In a20 mL microwave Biotage tube, a mixture of 4-iodo-1H-imidazole(1a) (0.194 g, 1.0 mmol), a boronic acid 2(2.0 mmol), CsF (0.456 g,3.0 mmol), PdCl2(dppf)(0.041 g, 0.05 mmol) and BnEt3NCl(0.011 g, 0.05 mmol) in toluene(7 mL) and water (7 mL)was purged with argon andheated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3a-3i and 3k-3o in yields ranging from 40 to 91%. Time and temperaturereactions were collected in Table 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Iodo-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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. Safety of 2-Imidazolecarboxylic acid

Example 45 lambda/-[6-(1H-lndol-4-yl)-1H-indazol-4-yl]-1H-imidazole-2-carboxamide 1H-lmidazole-2-carboxylic acid (17mg) (available from Maybridge), HATU (63mg) and 6- (1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2/-/-indazol-4-amine (50mg) were dissolved in anhydrous DMF (3ml) and then treated with DIPEA (0.052ml) and stirred at RT for 15h. The mixture was treated with methanol (3ml) and then macroporous-tosic acid resin (170mg; 4.4mmol/g) then stirred for 15h. The mixture was then treated with 0.88 ammonia solution (0.600ml), stirred for 10min, then filtered and solvent blown off under a stream of nitrogen. The crude residue was purified by mass directed preparative HPLC (Method A) to give the title compound. LC/MS R1 0.87min m/z 343 [MH+]. Method B

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16042-25-4, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 693-98-1, name is 2-Methyl-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 693-98-1, Quality Control of 2-Methyl-1H-imidazole

10 mmol of 2-methyl-1H-imidazole was added to a suspensionof potassium carbonate (10 mmol) in acetonitrile (10 mL), and then stirred for 15 min at r.t. 10 mmol of1-(chloromethyl)benzene was added to the reaction mixture and the mixture was heated to 70C and kept for 72 h. After completion of the reaction, the solvent was removed and the residue was dissolved in EtOAc (20 mL), washed with H2O(2¡Á10 mL) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: CHCl3)to afford the desired product. Yield 38%; yellow oil; UV-Vis (chloroform, lambda, nm): 290; IR spectrum (KBr, nu, cm-1): 2939,1712, 1508, 1434, 1365, 1272, 1118, 983, 721; 1H NMR (250.13 MHz, CDCl3) delta: 7.43-7.32 (m, 5H), 7.17-7.14 (m, 2H), 6.99(d, J = 1.3 Hz, 1H), 6.84 (d, J = 1.2 Hz, 1H), 5.11 (s, 2H), 2.27 (s, 3H); 13C NMR (62.9 MHz, CDCl3) delta: 144.3, 138.0, 129.3,128.1, 127.5, 127.1, 120.9, 49.2, 13.4.

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; Bouchouit; Bouraiou; Bouacida; Belfaitah; Merazig; Journal of Structural Chemistry; vol. 57; 4; (2016); p. 835 – 839; Zh. Strukt. Kim.; vol. 57; 4; (2016); p. 873 – 876,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 144690-33-5, The chemical industry reduces the impact on the environment during synthesis 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

Example 6; Preparation of 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic Acid DihydrateEthyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methyl imidazole-5-carboxylate (100 g) was dissolved in isopropyl alcohol (500 ml). Separately prepared solution of potassium hydroxide (32 g) in IPA (1.0 L) was added slowly to above solution at room temperature. Reaction mass was stir for 2-4 hrs at 30-40 C. Isopropyl alcohol was distilled under reduced pressure. Water (400 mL), sodium chloride (40 g) & ethyl acetate (1.0 L) was added to the residue. Separate the two layers & aqueous layer was extracted with ethyl acetate (3¡Á500 ml). Combined ethyl acetate layer was washed with sodium bicarbonate solution (3¡Á500 mL) & dried (Na2SO4). Distilled off ethyl acetate under reduced pressure completely & residue thus obtained was recrystallized from acetonitrile to get 4-(1-hydroxy-1-methylethyl)-2 propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic acid dihydrate (95 g).HPLC purity=99.0%Moisture Content5.0%.

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 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ramanjaneyulu, Gorantla Seeta; Mohan, Bandari; Ray, Purna Chandra; Sethi, Madhuresh Kumar; Rawat, Vijendra Singh; Krishna, Yerramalla Raja; Lakshminarayana, Vemula; Srinivas, Mamidi; US2009/281327; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 1450-93-7

EXAMPLE 2 5-(4-Pyridyl)imidazo[1,2-a]pyrimidine A mixture of 5.29 g of 2-aminoimidazole hemisulfate, 3.28 g of anhydrous sodium acetate and 7.04 g of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one (prepared according to the procedure of Example 63 in U.S. Pat. No. 4,281,000) in 100 ml of glacial acetic acid was heated under reflux for 16 hours. The procedure of the above Example 1 was followed and the title compound was obtained as pale yellow needles, mp 244-245 C.

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4551530; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C5H7BrN2

General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

The synthetic route of 24134-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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. Quality Control of 2-(1H-Imidazol-1-yl)ethanol

2-(1H-benzo[d]imidazol-1-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide-HCl (EDC-HCl) (2.20 g, 11.5 mmol) was added solid all at once to a magnetically stirred solution of naproxen (2.30 g, 10.0 mmol), 1-(2-hydroxyethyl)imidazole (1.12 g, 10.0 mmol) and 4-Dimethylaminopyridine (61 mg, 0.5 mmol) in dry tetrahydrofuran (50 mL) cooled in an ice bath and kept under nitrogen. The reaction mixture was stirred in an ice bath for 30 min and at ambient temperature. More EDC-HCl (400 mg, 2 mmol) was added after 13 hrs, 17 hrs. After stirring for 22 hrs at room temperature the mixture was concentrated and the residue partitioned between water (50 mL), saturated NH4Cl (20 mL) and EtOAc (120 mL). The organic layer was washed with 50% saturated NH4Cl (2*50 mL), 50% saturated NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried and concentrated. The oily residue was purified by Flash Chromatography using ethyl acetate and heptanes as eluent afforded a colourless oil (2.74 g, 84%) after drying in high vacuum. The oil was crystallised from ether and recrystallised from Tert-butylmethylether (?20 mL, seeded) to afford the title compound as a colourless solid (2.21 g, 68.3%). Mp. 60.6-61.3 C. 1H NMR (400 MHz, DMSO) delta 7.80 (d, J=9.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.68 (d, J=1 Hz, 1H), 7.51 (s, 1H), 7.33 (dt, J=5.5, 3 Hz, 1H), 7.30 (d, J=2.5 Hz, 1H), 7.17 (dd, J=9, 2.5 Hz, 1H), 6.98 (t, J=1 Hz, 1H), 6.78 (t, J=1 Hz, 1H), 4.34-4.12 (m, 4H), 3.92 (q, J=7 Hz, 1H), 3.88 (s, 3H), 1.45 (d, J=7 Hz, 3H). 13C NMR (101 MHz, DMSO) delta 173.52, 157.19, 137.40, 135.30, 133.33, 129.15, 128.37, 128.25, 126.99, 126.20, 125.63, 119.46, 118.73, 105.69, 63.74, 55.15, 44.94, 44.35, 18.19.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1615-14-1, its application will become more common.

Reference:
Patent; Larsen, Claus Selch; Larsen, Susan Weng; Thing, Mette Agergaard; Kristensen, Jesper Langgaard; Jensen, Henrik; ?stergaard, Jesper; US2014/315960; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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. SDS of cas: 7189-69-7

N,N? – sulfuryldiimidazole (5.00 g, 25.2 mmol, 1.0 eq) was then suspended in 50 mL of anhydrous dichloromethane at 0C under N2. Methyltrifluoromethanesulfonate (2.56 mL, 22.7 mmol, 0.9 eq) was added dropwise over 15 minutes at 0C. The reaction stirred at 0C for 2 hours. The solvent was decanted off and 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate was isolated as a white solid was washed three times each with 50 mL of cold dichloromethane and dried under high vacuum for 10 minutes and immediately used in the next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7189-69-7, its application will become more common.

Reference:
Patent; UNIVERSITY OF DELAWARE; GRIMES, Catherine, Leimkuhler; MELNYK, James, E.; LIANG, Hai; DEMEESTER, Kristen, E.; (65 pag.)WO2016/172615; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

Example 18 preparation of 6 – (4-iodo -1H-imidazol-1-yl) pyrimidin-4-amine (intermediate II-18)

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; East China University of Technology; Mao, Fei; Wang, Huan; Li, Xiaokang; Zhang, Haiyan; Lu, Zhengyu; Li, Jian; (43 pag.)CN105418592; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 1-Decyl-1H-imidazole

Equipped with a stirrer, a thermometer, a three-necked flask was added 1.67 g (8.0 mmol) N- decyl-imidazole, 0.56 g (4.4 mmol) 1,3- dichloro-2-propanol, at 115 ~ 125 C The reaction was stirred after, TLC tracking progress of the reaction, the reaction of about 8 ~ 12 h, the crude product was mixed with chloroform and ethyl acetate solvent was recrystallized to give a white powdery solid 1,1′-didecyl-3,3 ‘- (2- hydroxy-1,3-propylene) imidazole hydrochloride 1.42 g, yield 65.2%.

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; Qiqihar university; Wang, LiYan; Deng, QiGang; Zheng, YongJie; Huo, shichao; Liu, Jia; Sun, zhu; (10 pag.)CN103951702; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem