Month: April 2021

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 22884-10-2 as follows. COA of Formula: C5H6N2O2

PREPARALION OF ZLD-AC CRYSTAL FORM XNII; Example 18 :; A 3L reactor equipped with A mechanical stirrer, a thermometer, a reflux condenser and a dropping funnel, was loaded with 1-IMIDAZOLEACETIC acid (70. OG, 0. 56MOLE), Phosphorous acid (136. 7g, 1.67mole) and Silicon oil (M-350) (490ML). The suspension was heated to 80C and Phosphorous oxychloride (194. 4ML, 2.08mole) was added drop-wise during 4 hours. The reaction mixture was stirred at 80C for 22 hours. Then water (490ML) was added slowly at 80C. The mixture was stirred vigorously for about 30 minutes. Then the silicon oil phase and the aqueous phase were separated. The aqueous phase was put in a clean reactor and heated to 97C for 17.5 hours. Then absolute Ethanol (490ML) was added and the solution was stirred at reflux (87C) for 2 hours. The solution was then cooled to 70C-72C during about 1 hour and was kept at this temperature for 1 hour. After cooling to 25C during 2.5 hours and stirring at this temperature for 1 hour, half of the product was filtered, washed with small amount of cold water and dried in a vacuum oven at 50C for 20 hours to obtain 50.8g of Zoledronic acid crystal form XVIII (MS- 507-CROP I, LOD by TGA=1.9%). The rest of the suspension was cooled to 0C during 2 hours and was stirred at this temperature for about 16 hours. Then the product was filtered and dried in a vacuum oven at 50C for 24 hours to obtain 26g of Zoledronic acid crystal form XVIII (MS-507-CROP II, LOD by TGA=1. 0%). The overall yield of the process is 50% purity by HPLC 97.7%.

According to the analysis of related databases, 22884-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/5447; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H5BrN2

Preparation 14 Methyl-3-(1-methyl-imidazol-5-yl)-2-naphthoate To a mixture of methyl-3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate (Preparation 13) (15.37 g, 49.3 mmol) and 5-bromo-1-methyl-1H-imidazole (9.06 g, 49.3 mmol) in toluene/EtOH (350 mL/36 mL) were added Pd(PPh3)4 (11.37 g, 9.84 mmol), Na2CO3 (20.9 g, 197.2 mmol) and water (106 mL). The mixture was degassed, purged with N2, and heated to reflux for 20 hours. It was then cooled to RT, neutralized with HCl (1.0 N, 100 mL), and concentrated in vacuo. The residue was partitioned between water (300 mL) and EtOAc (1 L). The organic layer was washed with water (2 L) and brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting crude material was submitted to flash chromatography (1.5% MeOH/CHCl3), furnishing the title compound as a light-yellow solid (9.5 g, 72%).

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 1003-21-0.

Reference:
Patent; Burke, James R.; Townsend, Robert M.; Qiu, Yuping; Zusi, Fred Christopher; Nadler, Steven G.; US2003/22898; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5805-57-2, 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 5805-57-2 as follows.

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 3287-79-4, name is 5,6-Dimethyl-1H-benzo[d]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. Recommanded Product: 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione

Example 13. 2-[2-(Pyrrolidino)ethylthio]-5,6-dimethylbenzimidazole (XIII) and its dihydrochloride were synthesised as described above. The compound XIII was obtained from 2,67 g (0,015 mol) 2-mercapto-5,6-dimethylbenzimidazole and 2,9 g (0,017 mol) 2-(pyrrolidino)ethylchloridehydrochloride in the presence 1,35 g (0,034 mol) sodium hydroxide in 90% yield (4,0 g, counting on monohydrate), m.p. 115-116 C. (with decomp., from ethanol with water). 1H NMR (CDCl3), delta: 1,97 (4H, m, beta-H of pyrrolidine); 2,34 (6H, s, 2CH3); 2,72 (4H, m, -H of pyrrolidine); 3,02 (2H, m, CH2S); 3,19 (2H, m, CH2N); 7,18 (2H, broad s, ArH). Calcd for C15H21N3S*H2O: C 61,4; H 7,8; N 14,3; S 10,9; Found: C 61,4; H 7,8; N 14,5; S 10,9.

The synthetic route of 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nauchno-Issledovatelsky Institut Farmakologii Rossiiskoi Akademii Meditsinskikh Nauk; US6376666; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2,Some common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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.

2,4,5-Tribromo-1H-imidazole (1a) (98.7 g, 324 mmol, 1.0 eq) was dissolved into 1.20 L of DCM and cooled to 0 C. To this was added DIPEA (62 mL, 360 mmol, 1.1 eq) followed by the slow addition of [beta-(trimethylsilyl)ethoxy]methyl chloride (60.2 mL, 340 mmol, 1.05 eq). The solution was slowly warmed to room temperature. After 2 hours the mixture was washed with 1M H3PO4/saturated aqueous NaCl (1:10; 2¡Á600 mL). The organic layer was dried over MgSO4, and evaporated to dryness, yielding intermediate (1b) as faint yellow liquid that solidified on standing (137 g).

The synthetic route of 2034-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fatheree, Paul R.; US2011/218224; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, 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 305790-48-1, Recommanded Product: 305790-48-1

EXAMPLE 8 6-(3-chloro-phenyl)-1-methyl-1,3-dihydro-benzoimidazol-2-one Prepared from 1-methyl-6-bromo-1,3-dihydro-benzoimidazol-2-one and 3-chloro-phenyl boronic acid in the same fashion as that of Example 5. mp 219-220 C.; 1H-NMR (DMSO-d6) delta 11.0 (s, 1H), 7.75 (bs, 1H), 7.65 (dd, 1H, J=7.5, 1.76 Hz), 7.49-7.44 (m, 2H), 7.39-7.32 (m, 2H), 7.06 (d, 1H, J=7.94 Hz), 3.35 (s, 3H), MS (ES) m/z 259([M+H]+, 100%); Anal. Calc. For C14H11ClN2O: C, 65, H, 4.29, N, 10.83. Found: C, 64.44, H, 4.36 N, 10.6.

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; American Home Products Corporation; Ligand Pharmaceutical, Inc.; US6423699; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 705-09-9, 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 705-09-9 as follows.

Reagents and conditions: (a) morpholine, DIPEA, DCM, -78C – RT, 84.7%; (b) 2-(difiuoromethyl)-lH-benzimidazole, K2C03, DMF, RT, 85.5%; (c) piperazine, THF, reflux, 75.9%; (d) 02N-(CH2)5C0C1, Et3N, CHC13, RT, 92.5%; (e) HCOONH4, 10% Pd-C, CH3OH, -10C- RT, 56.6%.

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; REHEMTULLA, Alnawaz; GALBAN, Stephanie; ROSS, Brian, D.; VAN DORT, Marcian; WHITEHEAD, Christopher; WO2014/164942; (2014); A1;,
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, SDS of cas: 2302-25-2

Step 1: To a stirred mixture of DMF (15 mL) and NaH (60% dispersion in mineral oil, 539 mg, 21 mmol) at 0C under argon was added 4-bromo-1H-imidazole (3 g, 20 mmol) in one portion. The mixture was stirred for 5 min at 0C. A solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.3 mL, 24 mmol) in DMF (3 mL) was added dropwise. Afterstirring at 0 C for 1 h, the mixture was warmed slowly to rt and stirred for 6 h. The mixture was then partitioned betweenEtOAc (100 mL) and water (50 mL). The EtOAc layer was separated and washed with brine, dried over Na2SO4, filtered,and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel flash chromatography(eluting with a gradient of 100% hexanes to 100% EtOAc) to afford a regioisomeric mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole as an oil (2.9 g, 53%).LCMS (ESI) m/z 277 and 279 (M+H)+. Step 1: To a mixture of the regioisomers 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo,-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (643 mg, 2.3 mmol) from Step 1 of Example 32, acetamide(275 mg, 5.0 mmol), and Cs2CO3 (1.5 g, 5 mmol) in 1,4-dioxane (7 mL) was added N,N?-dimethylethylenediamine (500mL, 5 mmol). Argon was bubbled into the mixture for 5 min followed by the addition of CuI (221 mg, 1.1 mmol). Argonwas bubbled into the mixture for an additional 5 min. Then the reaction vessel was sealed and the mixture was heatedat 100 C for 15 h. The mixture was cooled to rt, then partitioned between EtOAc (100 mL) and water (50 mL). TheEtOAc layer was separated, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure.The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 100% EtOAc toafford a mixture of regioisomers N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)acetamide and N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)acetamide (170 mg, 29%) as an oil. LCMS (ESI) m/z 256 (M+H)+.

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; 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 760212-58-6, These common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, 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.

Subsequently, the following reagents and solvents were added into the reaction vessel.2.40 g (5.2 mmol, 1.1 eq) of 2-pinacolate-6,12-dinaphthylchrysene:Intermediate Compound M2: 1.66 g (4.7 mmol, 1.0 eq)Toluene: 75 mLSodium carbonate aqueous solution: 25 mL (3.0 eq)Then, while stirring the reaction solution, the following reagents were further added.Pd (PPh3) 4: 274 mg (0.24 mmol, 0.05 eq)Ethanol: 25 mLSubsequently, the reaction solution was stirred for 2 hours while heating and refluxing. After completion of the reaction, the reaction solution was cooled. Subsequently, liquid separation operation was performed using water, and the organic layer was recovered. Subsequently, the obtained organic layer was concentrated under reduced pressure. Thus, a crude product was obtained. Subsequently, the resulting crude product was purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 10/1), and the separated solution was concentrated under reduced pressure. Thus, a solid was obtained. Then, the resulting solid was subjected to slurry cleaning with methanol, followed by filtration. Thus, 2.82 g of the exemplified compound A11 (yield: 86.8%, HPLC purity: 99.8%) was obtained.

The synthetic route of 760212-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Canon Co., Ltd; Eiwawaki, Hironobu; O.O, Rui Hiroki; Jisina, Yuko; Murachbaki, Masanori; Takahashi, Tetsuro; (23 pag.)KR101489992; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Product Details of 492-98-8

A mixture of Zn(NO3)2 6H2O (44.6mg,0.15mmol),5-Brnic(60.6 mg,0.3mmol),H2biim (20.1mg,0.15mmol),NaOH(12.0mg,0.3 mmol),and H2O (10mL)was stirred at room temperature for 15min,and then sealed in a25mL Teflon-lined stainless steel vessel,and heated at 160 1C for 3days,followed by cooling to room temperature at a rate of 10 1C/h. Colorless block-shaped crystals were isolated manually,and washed with distilled water.Yield: 55%(basedon5-BrnicH).CalcdforC24H14Br2ZnN4O4:C 44.51%,H2.18%,N8.65%.Found:C44.17%,H1.84%,N8.24%.IR (KBr,cm1): 1609vs,1552m,1441m,1394w,1370vs,1342w,1281m,1237w,1181w,1125s,1088w,1028m,991w,925w,887w,862w,771m,754m,732m,687m,553w,and434w.

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gu, Jin-Zhong; Wu, Jiang; Kirillov, Alexander M.; Lv, Dong-Yu; Tang, Yu; Wu, Jin-Cai; Journal of Solid State Chemistry; vol. 213; (2014); p. 256 – 267;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem