Tag: M.W=100-200

33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below.

Synthesis of Ethyl 1~((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2- carboxylate (lnt~1a) ciInMa2-(Trimethylsilyl)ethoxymethyi chloride (12.8 g, 0.077 mol) was added to a stirred solution of ethyl imidazole-2-carboxylate (9.0 g, 0.064 mol) and potassium carbonate (17.7 g, 0.128 mol) in NtN-dimethylformamide (50 mL) at 0 ¡ãC. The mixture was allowed to stir from 0 ¡ãC to r.t. overnight. Water and ethyl acetate were added and the layers were separated. The separated aqueous layer was extracted with ethyl acetate (X2). The combined organic layers were washed with water (X2). The separated organic layer was dried (MgS04) and filtered. The solvents were removed in vacuo andchromatographic purification (ethyl acetate – hexane) of the residue gave imidazole InMa (12 g, 70percent) as a colorless oil. LCMS m/e (M + H+) – 271.1.

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; SCHERING CORPORATION; TSUI, Hon-Chung; PALIWAL, Sunil; KIM, Hyunjin, M.; KEREKES, Angela, D.; CAPLEN, Mary Ann; ESPOSITE, Sara, J.; MCKITTRICK, Brian, A.; FISCHMANN, Thierry Olivier; DOLL, Ronald, J.; RAINKA, Matthew Paul; LI, Ang; WO2011/149874; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

32673-41-9, A common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

1. Methyl 5-tert-butyl-2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate hydrochloride. 50 g of 1H-imidazole-4-methanol hydrochloride are reacted with 60 g of methyl 5-tert-butyl-2-hydroxybenzoate in 150 ml of concentrated sulfuric acid at 20 C. for 21 hours. The reaction mixture is then cautiously decomposed on ice. The solid product is filtered off, purified by chromatography and then converted into its hydrochloride. 1.1 g of methyl 5-tert-butyl-2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate hydrochloride is obtained. Yield: 2.8%. M.P.: 185-186 C. NMR (DMSO): delta 1.3(9H,s), 3.45(3H,s), 4.1(2H,s), 7.3(1H,s), 7.75(2H,m), 9.0(1H,s), 10.5 to 13,0 (3H).

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; U C B Societe Anonyme; US4923865; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

35203-44-2, 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 35203-44-2 as follows.

General procedure: A mixture of 9-bromo-10-(bromomethyl)anthracene (2) (1 mmol) and the relevant N-alkyl imidazoles(4a-f) or N-benzyl benzimidazoles (7a-e) in THF (15 ml)was refluxed at open condition for 24 h. By this time the products8a-f and 9a-e appeared as yellow precipitates which were isolatedby filtration, washed with little THF, then with ether and were airdried.Yield: 85-89percent (imidazolium salts) and 80-87percent (benzimidazoliumsalts).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 35203-44-2, and friends who are interested can also refer to it.

Reference:
Article; Chatterjee, Tanmay; Kumar, N. Tanmaya; Das, Samar K.; Polyhedron; vol. 127; (2017); p. 68 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. 60-56-0

[Cu(MeimzH)2(phen)(H2O)2]Cl2 (Cu-Met-phen) a solution was prepared by mixing 1 mmol (0.1142 g) of methimazole dissolved in 5 mL of water with 1 mmol (0.1802 g) of o-phenanthroline dissolved in 5 mL of ethanol. To this solution, 1 mmol (0.1705 g) of solid copper(II) chloride dihydrate was slowly added under continuous stirring. The resulting mixture was stirred at room temperature for 2 h. After that, a light green precipitate was formed which was separated, filtered and washed several times with ethanol. After this procedure it was dried in an oven at 60 C. Anal. Calc. for C20H24N6O2S2Cl2Cu: C, 41.48; H, 4.15; N, 14.52; S, 11.06. Found: C, 41.15; H, 4.27; N, 14.78; S, 11.38 %. Yield: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, 60-56-0, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Urquiza, Nora M.; Islas, M. Soledad; Dittler, Maria Laura; Moyano, Maria A.; Manca, Silvia G.; Lezama, Luis; Rojo, Teofilo; Medina, Juan J. Martinez; Diez, Maximiliano; Tevez, Leonor Lopez; Williams, Patricia A.M.; Ferrer, Evelina G.; Inorganica Chimica Acta; vol. 405; (2013); p. 243 – 251;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, The chemical industry reduces the impact on the environment during synthesis 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, I believe this compound will play a more active role in future production and life.

To a solution of 1 -methyl- lH-imidazole-5-carbaldehyde (2.9 g, 26.3 mmol) in toluene (20 mL) was added propane- 1 , 3 -diol (4.01 g, 52.7 mmol) and CSA (0.306g, 1.317 mmol) and the reaction mixture was heated to reflux with azeotropic removal of the evolved water for 24 hours. The reaction mixture was cooled to RT, diluted with DCM and washed with NaHCO3 solution. It was then dried over Na2SO4, filtered and concentrated. Purification by column chromatography (80% EtOAc in Hexane to EtOAc) afforded 38 (2.53 g, 57% yield) as a yellow oil which solidified on standing to a yellow solid. MS (m/z): 169.2 (M+H)

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-5-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; METHYLGENE INC.; WO2009/109035; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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 synthesis method is as follows: In a 100 ml single-mouth flask, add 2.85g (10mmol) dehydroabietylamine, 1.87g (12mmol) imidazol-4,5-dicarboxylic acid (molar ratio of 1:1.2) and 50 ml of toluene. 110 C reflux condenser reaction 8h. After the reaction heat filter, steaming and obtaining white solid, quality is 2.0329g, yield of 46.1%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4,5-dicarboxylic acid, its application will become more common.

Reference:
Patent; Nanjing Forestry University; Xu, Li; Zhao, Fengyi; Xu, Yuanyuan; Yang, Shilong; Sun, Li; Wang, Luna; Wang, Weifan; (9 pag.)CN105037191; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 16042-25-4, name is 2-Imidazolecarboxylic acid, I believe this compound will play a more active role in future production and life. 16042-25-4

5 (1.00 g, 3.30 mmol) and 1H-imidazole-2-carboxylic acid(0.40 g, 3.60 mmol) were dissolved in 3 mL sulfolane, and 12 mLPOCl3 was added. The reaction mixturewas stirred at 85 C for 18 h,then cooled to room temperature, poured into 200 mL ice water.NaOH was added to adjust the PH to 7. The mixturewas filtered anddried in vacuo to give 92 mg of 11-3 as gray solid: 7% yield. 1H NMR(300 MHz, DMSO-d6) delta 13.83 (s, 1H), 8.77 (d, J = 5.4 Hz, 1H), 8.01 (d,J = 9.0 Hz, 1H), 7.52 (s, 1H), 7.36 (d, J = 2.5 Hz, 1H), 7.28 (d, J =5.2 Hz,2H), 7.18 (dd, J= 9.2, 2.6 Hz, 1H), 5.82 (s, 2H), 3.90 (s, 3H); m.p.:205-207 C; HRMS (ESI+) m/z 380.0914 (380.0924 calcd forC17H14N7O2S+, [M+H]+).

The chemical industry reduces the impact on the environment during synthesis 16042-25-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuan, Haoliang; Liu, Qiufeng; Zhang, Li; Hu, Shihe; Chen, Tiantian; Li, Huifang; Chen, Yadong; Xu, Yechun; Lu, Tao; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 491 – 502;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

570-22-9, The chemical industry reduces the impact on the environment during synthesis 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, I believe this compound will play a more active role in future production and life.

A mixture of CaCl2 (0.012 g, 0.1 mmol), H3imdc (0.039 g,0.25 mmol), Zn(Ac)2?2H2O (0.022 g, 0.1 mmol) and a buffer solution of HAc-NaAc (pH = 5.7, 2 mL) was put into 25 mL Teflon-lined stainless steel autoclave and heated at 180 C for 3 days, then cooled to room temperature. Dark yellow block crystals were obtained by filtration to give a yield of 32.7% (0.010 g). Elemental Anal. Calc. for C12H8Ca2N4O12Zn2: C, 23.58; H, 1.32; N, 9.17. Found: C, 23.22; H, 1.37; N, 8.95%. IR (KBr, cm-1): 3448 s, 1600 s, 1482 vs 1400 s, 1252 m, 1105 m, 804 m, 664 m.

The chemical industry reduces the impact on the environment during synthesis 1H-Imidazole-4,5-dicarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ablet, Ayjamal; Li, Shu-Mu; Cao, Wei; Zheng, Xiang-Jun; Jin, Lin-Pei; Polyhedron; vol. 83; (2014); p. 122 – 129;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 19 Synthesis of 2-benzimidazolecarbaldehyde-(5-nitro-2-pyridyl)hydrazone (compound 19) A desired product was obtained in the same manner as in Example 1 by using 3.20 g (20.8 mmol) of 5-nitro-2-pyridylhydrazine and 2.90 g (19.8 mmol) of 2-benzimidazolecarbaldehyde. Yield: 4.80 g (17.0 mmol) [yield rate: 86percent] Melting point: 310¡ã to 311¡ã C.

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; Kabushiki Kaisha Toshiba; US5569763; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 13750-62-4, name is 1-Benzyl-2-methyl-1H-imidazole, molecular formula is C11H12N2, 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. 13750-62-4.

The 1-benzyl-2-methylimidazole (0.64 cm3, ?4 mmol) was added to the solution of NiCl2¡¤6H2O (0.24 g, ?1 mmol) and NH4SCN (0.15 g, 2 mmol) in methanol (50 cm3). The mixture was refluxed for about 2 h and after the time the reaction solution was filtered and blue single crystals were obtained by slow evaporation of the solvent.(0013)(3): IR (KBr): 3119, 3030 nuArH; 2954 nuCH; 2094 nu(CN from SCN); 1537 nuCN, 1495 nuC=C; 1451, 1415 1351 delta(C-CH in the plane); 1280, 1140 delta(N-CH in the plane); 988 delta(CH3); 726 nu(SC from SCN).(0014)UV-Vis (methanol, lambda (nm): 1069.7, 647.8, 414.5, 267.6, 264.3, 258.2, 252.2, 247.2, 211.4.

The synthetic route of 1-Benzyl-2-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma?ecki; Maro?; Polyhedron; vol. 50; 1; (2013); p. 452 – 460;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem