Tag: M.W=100-200

583-39-1, A common compound: 583-39-1, name is 2-Mercaptobenzimidazole, 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.

A mixture of 1H-benzo[d]imidazole-2(3H)-thione (III, 21 mg, 0.2 mmol) and [RuII(eta6-p-cymene)(PPh3)(CH3CN)Cl]PF6 (5, 144 mg, 0.2 mmol) in CH2Cl2 (20 mL) was stirred for 3 h at room temperature. The solvent was concentrated to a small amount (ca. 3 mL) and the product was precipitated by addition of pentane (ca. 20 mL). The orange yellow powder was filtered, washed with pentane (2 ¡Á 5 mL) and dried in vacuo. Yield: 146 mg (88%), m.p. 200 C (decomp.). Elemental analysis (%) calcd. for C35H35ClF6N2P2RuS*0.5CH2Cl2: C 48.97, H 4.17, N 3.22, S 3.68, found: C 49.02, H 4.38, N 3.29, S 3.74. 1H-NMR (CDCl3): delta = 11.46 (s, 2H, NH),7.58-7.62 (m, 6 H, PPh3), 7.34-7.37 (m, 10H, PPh3/Ar-thione), 7.24-7.27 (m, 3H, PPh3), 5.47 (d, J = 6 Hz, 1 H, H-Ar), 5.31 (d, J = 6 Hz, 1 H, H-Ar), 5.21 (d, J = 6 Hz, 1 H, H-Ar), 5.06 (d, J = 6 Hz, 1 H, H-Ar), 2.81-2.89 (m, 1 H,CH(CH3)2), 1.90 (s, 3 H, CH3), 1.18 (d, J = 7 Hz, 3H, CH(CH3)2), 1.16 (d, J = 7 Hz, 3H, CH(CH3)2) ppm. 13C{1H}-NMR (CDCl3): delta = 163.8 (C=S), 134.1 (C-PPh3), 132.0 (C-PPh3), 131.6 (C-Arthione), 131.1 (C-Arthione), 130.8 (C-PPh3), 128.4 (C-PPh3), 124.6 (C-Arthione), 116.5 (C-Ar), 111.7 (C-Arthione), 101.1 (C-Ar), 92.0 (d, J = 2 Hz, C-Ar), 91.3 (d, J = 4 Hz, C-Ar), 90.0 (d, J = 2 Hz, C-Ar), 89.0 (d,J = 4 Hz, C-Ar), 30.5 (CH(CH3)2), 22.5(CH(CH3)2), 21.4 (CH(CH3)2), 17.6 (CH3) ppm. 31P{1H}-NMR(CDCl3): delta = 29.5 (s, PPh3), -144.2 (sept, PF6) ppm.

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, 2-Mercaptobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hanif, Muhammad; Nawaz, Muhammad Azhar Hayat; Babak, Maria V.; Iqbal, Jamshed; Roller, Alexander; Keppler, Bernhard K.; Hartinger, Christian G.; Molecules; vol. 19; 6; (2014); p. 8080 – 8092;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 3314-30-5.

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(5-methylpyrimidin-2-yl)methyl]- 1 ,3-thiazole-4-carboxamide dihydrochloride (197) (223 mg, 0.52 mmol), 1 H-benzimidazole-2-carbaldehyde (99 mg, 0.68 mmol), DIPEA (0.363 ml, 2.09 mmol) and MgSQ (400 mg) in MeOH (6 ml) at room temperature for 24 h, followed by addition of NaBH4 (30 mg, 0.78 mmol) gave the title compound (120 mg, 52percent) as a white solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.21 (s, 1 H), 8.72 (t, J = 5.8 Hz, 1 H), 8.63 – 8.57 (m, 2H), 7.50 (s, 1 H), 7.14 (dd, J = 6.0, 2.7 Hz, 2H), 4.61 – 4.56 (m, 2H), 3.98 (s, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.95 (t, J = 6.3 Hz, 2H), 2.75 (s, 1 H), 2.26 (s, 3H) HPLCMS (Method C): [m/z]: 442 [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; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, Adding some certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0.

To 10 mL of Acetonitrile were added 3 mmol (1.05 g) of methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate (WO 2012/018635) 3.3 mmol (376 mg) of 2-mercapto-1-methylimidazole and 6.6 mmol (910 mg) of K2C03. The solution was stirred at room temperature overnight. When TLC showed no remaining methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate the reaction mixture was diluted with 10 mL of water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried with Na2S04 and evaporated under reduced pressure. The crude product was then purified by recrystallization from ethanol to yield 1.04 g of yellow crystals (81 % yield). 1H NMR (200 MHz, DMSO-cf6) d 8.66 (d, J = 1.9 Hz, 1 H), d 8.34 (d, J = 1.8 Hz, 2H), d 7.28 (s, 1 H), d 6.87 (s, 1 H), d 3.91 (s, 3H), 3.51 (s, 3H), d 3.10 (s, 3H), d 2.92 (s, 3H). MS m/z: not found

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 60-56-0.

Reference:
Patent; UNIVERSITAeT WIEN; ERKER, Thomas; SCHREPPEL, Philipp; (235 pag.)WO2019/193159; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below.

To awarm solution of [(eta6-p-cymene)RuI2]2 (49 mg, 0.05 mmol)in ethanol (2.5 mL) a warm solution of HL (16 mg, 0.1 mmol) inethanol (2.5 mL) and triethylamine (13.92 mL), were added. Themixture was stirred at room temperature for 4 h. The orange-redproduct was filtered off, washed with ethanol (4 mL), diethylether and dried in vacuo. Yield: 35.7 mg, 68.4%. Anal. Calcd forC18H19IN2O2Ru, %: C, 41.31; H, 3.66; N, 5.35. Found, %: C, 41.27; H,3.75; N, 5.22. IR (ATR, cm1): 3070(m), 2962(s), 2754(m), 1637(s),1590(m), 1527(s), 1474(s), 1329(s), 1228(m). 1H NMR (199.97 MHz,DMSO-d6, delta, ppm): 14.06 (s, 1H, NH), 7.98 (dd, 1H, JHeH 2.7 and6.5, Hz, CHL), 7.63e7.56 (m, 1H, CHL), 7.55e7.45 (m, 2H, CHL), 5.99(d, 1H, JHeH 5.9 Hz, CHcymene), 5.90 (q, 2H, JHeH 6.3 Hz, CHcymene),5.80 (d, 1H, JHeH 5.9 Hz, CHcymene), 2.81 (m, 1H,JHeH 6.9 Hz, eCH(CH3)2), 2.33 (s, 3H,eCH3), 1.14 (dd, 6H,JHeH 2.8 and 6.9 Hz, eCH(CH3)2). 13C NMR (50.28 MHz, DMSO-d6 ,delta, ppm): 20.27 (eCH3), 22.15 (eCH(CH3)2), 31.55 (eCH(CH3)2),79.05, 80.18, 80.88, 81.08, 86.17 (CHcymene), 96.76 (CeCH3), 103.30(CeCH(CH3)2), 114.12, 118.40, 124.42, 125.69 (CHL), 134.02, 140.90(CeCHL), 145.11 (CeCOO), 163.65 (eCOO). ESI-MS (MeOH): m/z397.049 [M-I]+, 353.059 [M-I-CO2]+.

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:
Article; Panti?, Darko N.; Arancrossed D Signelovi?, Sandra; Radulovi?, Sini?a; Roller, Alexander; Arion, Vladimir B.; Grguri?-?ipka, Sanja; Journal of Organometallic Chemistry; vol. 819; (2016); p. 61 – 68;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1849-01-0 name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. 1849-01-0

Example 7 Preparation of 1,3-dihydro-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-2H-benzimidazol-2-one (Compound 159) A mixture of 3-[4-(chloromethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (i.e. the product of Example 1, Step B) (0.3 g, 1.1 mmol), 1,3-dihydro-1-methyl-2H-benzimidazol-2-one (0.17 g, 1.1 mmol) and cesium carbonate (0.56 g, 1.7 mmol) in N,N-dimethylformamide (2.5 ml) was stirred at room temperature for 12 h. The reaction mixture was partitioned between ethyl acetate (25 ml) and water (5 ml). The organic layer was separated and washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (eluting with a gradient of 0 to 50% ethyl acetate in hexanes) to provide the title compound, a compound of the present invention, as a solid (0.095 g). 1H NMR (CDCl3): delta 3.49 (s, 3H), 5.16 (s, 2H), 6.81-6.90 (m, 1H), 6.97-7.06 (m, 2H), 7.06-7.18 (m, 1H), 7.47 (d, 2H), 8.07 (d, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; FMC Corporation; PASTERIS, Robert James; CHITTABOINA, Srinivas; MCMAHON, Travis Chandler; KAMIREDDY, Balreddy; REDDY, Ravisekhara Pochimireddy; (121 pag.)US2020/148672; (2020); 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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 46006-36-4

1 H-Benzoimidazole-4-carboxylic acid (7.3 g) was suspended in 350 ml of tetrahydrofuran and cooled with dry ice-acetone bath. Lithium aluminium hydride (4M, 21 ml) was slowly added. The reaction wasstirred and allowed to warm up to room temperature overnight. The reaction was quenched with 5 ml methanol and extracted with 800 ml of 20% methanol and 80% ethyl acetate. After filtration, solid was discarded. Evaporation of filtrate under reduced pressure resulted in 7 g crude (1H-Benzoimidazol-4-yl)methanol (M+1=149.1,) to be used for next step

The synthetic route of 46006-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; ZHOU, Qun-Yong; (93 pag.)WO2017/177026; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, A common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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.

Figure 1 shows the structures and synthetic pathways of methimazole derivatives. Briefly, compound 3 (3) was prepared through the reaction of an MMI (compound 2; 2) (400 mg, 3.5 mmol) and potassium carbonate (968 mg, 7 mmol) in 7 mL of N,N-dimethylformamide and the subsequently di-tert-butyl dicarbonate (1.1 mL, 5.2 mmol) was added. The reaction mixture was stirred at 60 C for 30 min in an N2 atmosphere. The resulting mixture was partitioned between ethyl acetate (40 mL) and H2O (20 mL). The organic layer was washed with brine (20 mL), dried over MgSO4, and then concentrated in vacuo. The residue was separated by chromatography over silica gel and eluted with hexane/ethyl acetate (1:1) to afford 665 mg (89% yield) of 3.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chan, Chin-Feng; Lai, Shih-Ting; Guo, Yi-Cin; Chen, Ming-Jen; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2809 – 2815;,
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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., 570-22-9

In a dried flask, to 1H-imidazole-4,5-dicarboxylic acid (25 g, 157 mmol) in toluene (334 ml), DMF (12.1 ml) and thionyl chloride (94 ml, 1.29 mol) were added. The mixture was stirred for24 h at 80G. The mixture was concentrated under reduced pressure. Toluene (100 ml) was added and the mixture was concentrated under reduced pressure to give 35.5 g of the title compound as crude material which was used at the same day without further purification for subsequent steps.

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; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-80-3, 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. 4887-80-3, name is 5-Methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: PhI(OAc)2 (0.5 mmol) was added to a mixture of 1H-benzimidazole(1a; 0.5 mmol), isochroman (2a; 2.0 mmol), and DCE (2.0mL) in a Schlenk tube at r.t. The mixture was stirred at 80 C for6 h then cooled. H2O (10 mL) was added, and the mixture wasextracted with CH2Cl2 (3 ¡Á 10 mL). The combined organic layerwas dried (Na2SO4) and concentrated under reduced pressure.The residues were purified by flash column chromatography(silica gel, hexane-EtOAc) to give a colorless oil; yield: 115 mg(92%).

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; Sun, Bin; Yan, Zhiyang; Jin, Can; Su, Weike; Synlett; vol. 29; 18; (2018); p. 2432 – 2436;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

150 g of (3-mercaptopropyl) triethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.), 85.7 g of limonene (manufactured by Tokyo Chemical Industry Co., Ltd.), 2 g of 2,2′-azobis (isobutyronitrile ) (Manufactured by Wako Pure Chemical Industries, Ltd.) and 300 ml of ethanol were mixed in a recovery flask, bubbled with nitrogen gas for 30 minutes, and reacted at 70 C. for 6 hours.After that, the reaction solution was concentrated to obtain 227 g of a colorless liquid (yield: 97%).To 150 g of the obtained compound, 45.7 g of 1-methylimidazole-2-thiol (manufactured by Wako Pure Chemical Industries, Ltd.), 2 g of 2,2′-azobis (isobutyronitrile) (manufactured by Wako Pure Chemical Industries, ) And 300 ml of ethanol were mixed in a recovery flask, bubbled with nitrogen gas for 30 minutes, and reacted at 70 C. for 6 hours.After that, the reaction solution was concentrated to obtain 185 g of a white solid (yield: 95%).The reaction formula is as follows, and 1-methyl-2-((2-methyl-5-(2-((3-(triethoxysilyl)propyl)thio)propan-2-yl)cyclohexyl)thio)-1H-imidazole.

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 60-56-0.

Reference:
Patent; TOYO TIRE & RUBBER COMPANY LIMITED; YURI, TAKASHI; (21 pag.)JP6047434; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem