Category: 22884-10-2

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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 22884-10-2

Examples; CRYSTAL FORMS OF ZOLEDRONIC ACID (ZLD-Ac); Preparation of ZLD-AC crystal form I; General procedure for the preparation of ZLD-AC crystal form I starting from 1- Imidazoleacetic acid (IAA), Phosphorous acid (H3PO3) and Phosphorous oxychloride (POC13) (Examples 1-9, see Table 1) :; A cylindrical reactor equipped with a mechanical stirrer, a thermometer, a reflux condenser and a dropping funnel, is loaded with 1-IMIDAZOLEACETIC acid (IAA), Phosphorous acid and a diluent (Toluene/Chlorobenzene/PEG-400/Silicon oil). The obtained suspension is heated to 75C-80C and Phosphorous oxychloride is added drop- wise. The reaction mixture is then heated to 75C-100C for 1-34 hours. Then water is added at 80C-100C. The mixture is stirred vigorously for about 15 minutes. [In some cases, when Silicon oil is used as a diluent, there is a need to add Toluene in order to improve the separation between the oily phase and the aqueous phase]. Then the phases are separated. The aqueous phase is put in a clean reactor and heated to 95C-100C for 13.5-19 hours. Then it is cooled to 5C and absolute Ethanol is added to obtain a precipitate after stirring at 5C for 2.5-4 hours [In some cases a precipitate of Zoledronic acid is obtained without adding absolute Ethanol as an anti-solvent]. The white product is then filtered, washed with absolute Ethanol and dried in a vacuum oven at 50C for 17-24 hours to obtain Zoledronic acid crystal form I (LOD BY TGA=6. 3%-9. 3%).; ZLD HPLC METHOD: COLUMN: PHENOMENEX PHENYL-HEXYL 5UM, 250X4.6MM MOBILE PHASE: 40MM OCTANSULFONIC ACID SODIUM SALT IN 1% HCLO4, 0.2% H3PO4 : METHANOL (85:15) DETECTION: 220NM STABILITY WAS MEASURED VERSUS THE PRESENCE OF FORM II. P THE STABILITY DATA FOR EXAMPLE 4 IN THE TABLE ABOVE IS:

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

22884-10-2, Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 22884-10-2.

To a 50 mL flask was added 4-trifluoromethyl-2-azidoaniline1c (1 mmol), alpha-bromotrifluoroacetone (1.2mmol) And potassium carbonate (1.5mmol), React at 45 C, The reaction solvent was chloroform (20 mL). After 2 hours of reaction, Additional diphenylmethylphosphine (1.5 mmol) was added. The reaction was carried out at 30 C, and after continuing the reaction for 3 hours, The solvent chloroform was removed under reduced pressure. The intermediate was transferred to a solution of triphenylphosphine (2.5 mmol) and elemental iodine (2.5 mmol) in chloroform (15 mL). Then add imidazoleacetic acid (1.5 mmol), React at 45 C, Reaction for 2 hours, After the reaction is completed, The solvent chloroform was removed under reduced pressure. The primary product was subjected to column chromatography to give 0.192 g of the title compound 2c, yield 51%.

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-(1H-Imidazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hubei Wenli College; He Ping; Wang Liping; Pei Fei; Jin Shan; Ren Zhilin; Wang Long; (10 pag.)CN109400589; (2019); A;,
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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., 22884-10-2

48.87 g (0.4 mol) of 3,4-diaminotoluene and 63.05 g (0.5 mol) of 1-imidazole-1-acetic acid were weighed into a 1000 mL three-necked flask and 375 mL of 4 mol / L hydrochloric acid was added The mixture was stirred for 20 h at room temperature. The solution was reddish-brown and then refluxed at 100 C for 15 h. The solution gradually deepened and finally dark brown. After cooling, the reaction solution was poured into 1000 mL of distilled water and adjusted to pH 7-8 with ammonia. A large amount of precipitate was collected, suction filtered and then recrystallized from hot water to obtain 33.02 g of yellow crystals (yield: 38.89%).

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; Henan Polytechnic Institute; Huang, Qiuying; Lin, Xichang; Yang, Yi; Liu, Wei; Liu, Chunli; Su, Mingyang; Chen, Xiaodong; Du, Xikun; Shen, Gang; Fang, Lei; Meng, Xiangru; (8 pag.)CN104610310; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

22884-10-2, These common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 mixture of 1-imidazolylacetic acid (25g; 0.1538mol) and H3PO3 (18.9g; 0.2306mol) in N,N’-dimethylethyleneurea (DMEU) (150ml) is heated to a temperature of from 4O0C to 500C. PCl3 (26ml; 0.3076mol) is slowly added to the resulting suspension. The resulting mixture is heated to a temperature of from 500C to 6O0C and stirred until reaction is complete by HPLC. Water is slowly added to the reaction mixture and the resulting solution is heated, with stirring, to a temperature of from 800C to 1000C until the reaction is complete. The reaction mixture is cooled to ambient temperature and the pH is adjusted to pH 8.0 to 9.0 with aqueous sodium hydroxide solution. The resulting solution is filtered and the pH of the solution is adjusted to pH 1.5 to 2.0. Ethanol is added and precipitation of solids occurs. The solid is filtered, washed and dried under vacuum at a temperature of from 45C to 550C to a constant weight. 25.7g of zoledronic acid is obtained (molar yield: 85.6%) with a HPLC purity higher than 99.5% in area. [The yield was calculated on dry basis]The product was characterized as follows:1H NMR (D2O) delta=4.71 (t, 2H, CH2); 7.28 (dd., IH3CH); 7.44 (dd., IH, CH); 8.62 (s., IH, CH)31P NMR (D2O) delta= 16.03

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 22884-10-2.

Reference:
Patent; HOVIONE INTER LIMITED; TURNER, Craig, Robert; WO2008/56129; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, molecular formula is C5H6N2O2, 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. 22884-10-2

Example 1; [0022] An oven-dried 250 ml_ 4-neck RB flask was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet and two 1/8 inch polytetrafluoroethylene (PTFE) feeding lines. The system was flushed with nitrogen for 30 minutes. Under nitrogen protection, imidazoIe-1-ylacetic acid (15.97 g, 0.13 mole), sulfolane (70 ml_) and phosphorous acid (2.67 g, 0.033 mol) were charged to the RB flask. The reaction mixture was mixed at 210 RPM and heated to 600C. PCI3 (9.18 g, 0.067mol) was added slowly (1.3 mL/mn) via a masterflex tubing pump. Five minutes were allowed for mixing. Alternately fed were 26 wt% phosphorous acid sulfolane solution (30.7 g, 10.23 g each addition at 1.6 mL/min) and PCI3 (27.5 g, 9.18 g each portion at 1.3 mL/min). Three to five minutes of mixing were allowed between additions. The addition took 1 hr 3 min and temperature was maintained between 600C and 670C. After addition was complete, the temperature of the reaction mixture was raised to 800C and was held at this temperature for 4 hours. Then the temperature of the reaction mixture was raised to 880C and held for 30 minutes. Ambient temperature water (50 g) was added in to quench the reaction. The solution was refluxed for 3 hrs . temperature, the product was vacuum-filtered and rinsed with 38 g of acetone. Zoledronic acid was obtained as a white crystalline solid (24.1 g, 95.3wt% purity by quantitative NMR, 65% yield). Example 2; [0023] An oven-dried 250 mL 4-neck RB flask was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet and two 1/8 inch PTFE feeding lines. The system was flushed with nitrogen for 30 minutes. Under nitrogen protection, imidazole-1-ylacetic acid (15.97 g, 0.13 mole), sulfolane (70 mL) and phosphorous acid (2.67 g, 0.033 mol) were charged to the RB flask. The reaction mixture was mixed at 300 RPM and heated to 600C. PCI3 (9.18 g, 0.067mol) was added in slowly (1.3 mL/min) via a masterflex tubing pump. Five minutes were allowed for mixing. Alternately fed were 26 wt% phosphorous acid sulfolane solution (30.7 g, 10.23 g each addition at 1.6 mL/min) and PCI3 (27.5 g, 9.18 g each portion at 1.3 mL/min. Three to five minutes of mixing were allowed between additions. The addition took 1 hr 6 min and temperature was maintained between 54 and 64C. After addition was complete, the temperature of the reaction mixture was raised to 800C and held for 4 hours. Then the temperature of the reaction mixture was raised to 880C and held for 30 minutes. This slurry was transferred via 3/8″ PTFE tubing using nitrogen pressure into 100 mL of pre-heated (80C) water under mixing. The resultant water solution was heated to refluxing and held at that temperature for 4 hr. It was then slowly cooled to room temperature then to 1-2C and held for 1.5 hr at this temperature. The product was collected via vacuum filtration. The cake was rinsed with acetone (20 g) and zoledronic acid was obtained as a white crystalline solid (19.1 g, 98.3 wt% purity by quantitative NMR, 53% yield). Example 3; [0024] An oven-dried 250 mL 4-neck RB flask was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet and two 1/8 inch PTFE feeding lines. The system was flushed with nitrogen for 30 minutes. Under nitrogen protection, imidazole-1-ylacetic acid (15.9 g, 0.13 mole), sulfolane (70 mL) and phosphorous acid (2.67 g, 0.033 mol) were charged to the RB flask. The reaction mixture was mixed and heated to 6O0C. PCI3 (36.7 g, 0.267 mol) and phosphorous acid (8.0 g, 0.098 mol) in – . mL/min respectively. Reaction temperature remained between 6O0C and 67C during feeding, After addition of PCI3 and phosphorous acid, the reaction slurry was heated to 800C and held at that temperature for 4 hours. This slurry was then transferred via 3/8″ PTFE tubing using nitrogen pressure into 50 m._ of pre-heated (8O0C) water under mixing. The resultant water solution was heated to refluxing and held at that temperature for 4 hr. It was then slowly cooled to 48-500C. Acetone (200 ml_) was added in slowly and then it was cooled to 1-2C and held for 2 hr at this temperature. The product was collected via vacuum filtration. The cake was rinsed with acetone (35 g) and zoledronic acid was obtained as a white crystalline solid (22.1 g, 98.6 wt% purity by quantitative NMR, 61 % yield). Example 4; [0025] A 2.5 L resin-kettle was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet, two 1/8 inch PTFE tubing as PCI3 and phosphorous acid sulfolane solution feeding lines. The system was dried under a stream of nitrogen. Under nitrogen, imidazoleacetic acid (79.92 g, 0.63 mol), phosphorous acid (13.90 g, 0.17 mol) and sulfolane (350 ml_) were added to the resin-kettle and mixed at 200 RPM. The mixture was heated to 62C then PCI3 (36.7 g, 0.267 mol) was added in slowly (1.3 mL/min) using a masterflex tubing pump. The slurry was mixed for 5 minutes. Phosphoro…

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22884-10-2, its application will become more common.

Reference:
Patent; ALBEMARLE CORPORATION; WO2008/157050; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem