Tag: M.W=100-200

These common heterocyclic compound, 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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. Safety of 5-Chloro-1H-benzo[d][1,2,3]triazole

General procedure: in EtOAc/MeOH (4:1) mixture solvent (2 mL), benzotriazoles 1 (0.3 mmol), sodium sulfinates 2 (0.54 mmol), NaBr (0.36 mmol) and mCPBA (0.39 mmol) were added successively. The suspension mixture was vigorously stirred at room temperature for 4 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL), basified with sat. aq. Na2CO3(8 mL) and H2O (5 mL). The mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (3:1 (v/v) petroleum ether/ethyl acetate) to furnish sulfonylbenzotriazoles 3.

The synthetic route of 5-Chloro-1H-benzo[d][1,2,3]triazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Sixue; Zhang, Yikun; Yan, Jie; Synthetic Communications; vol. 46; 17; (2016); p. 1432 – 1437;,
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Synthetic Route of 2613-30-1, The chemical industry reduces the impact on the environment during synthesis 2613-30-1, name is 4-Chloro-2,5-difluoroaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

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, 4-Chloro-2,5-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
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Electric Literature of 363-51-9, 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 363-51-9 as follows.

EXAMPLE 7 (1H-Benzimidazol-2-yl)-(2-chloro-6-fluorophenyl)amine hydrochloride 2-Chloro-6-fluoroaniline (0.48 g) and 2-chlorobenzimidazole (0.5 g) were mixed in a flask and then kept at 170 C. for 30 min. After cooling, the residue was dissolved out of the flask at boiling heat using 1 N HCl and 10% ethanol. The material dissolved out was then stirred at RT for 30 min, then the insoluble material was filtered off with suction and the filtrate was evaporated. The residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA). The clean fractions were combined, the acetonitrile was stripped off, the residue was adjusted to pH 10 with potassium carbonate solution, extracted three times with EA, and then the combined phases were dried, filtered, and concentrated. The residue was taken up using HCl/water and freeze-dried. 27 mg of the title compound were obtained. LCMS-Rt: 3.45 min; MS (ES+, M+H+): 262.0

According to the analysis of related databases, 363-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hofmeister, Armin; Heinelt, Uwe; Lang, Hans-Jochen; Bleich, Markus; Wirth, Klaus; Gekle, Michael; US2002/132842; (2002); A1;,
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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. 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Chloropropan-1-amine hydrochloride

3-Chloropropylamine hydrochloride (12 mg, 0.093 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC, 17 mg, 0.089 mmol), 4,4-dimethylaminopyridine (DMAP, 1 mg 0.008 mmol) and Et3N (50 muL, 0.359 mmol) were added to a solution of 1-pyreneacetic acid (20 mg, 0.077 mmol) in anhydrous CH2Cl2 (1 mL) under an argon atmosphere. The reaction mixture was stirred at room temperature for 7 h, quenched with aqueous saturated NH4Cl solution, and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (CH2Cl2) to give 6 as a pale yellow solid (13 mg, 50%). 1H-NMR (400 MHz, CDCl3) delta (ppm) 8.20 (2H, d, J = 7.6 Hz), 8.15 (3H, d, J = 7.9 Hz), 8.08 (1H, d, J = 9.2 Hz), 8.04 (1H, d, J = 9.2 Hz), 8.02 (1H, t, J = 7.9 Hz), 7.88 (1H, d, J = 7.9 Hz), 4.28 (2H, s), 3.31 (2H, t, J = 6.4 Hz), 3.25 (2H, q, J = 6.4 Hz), 1.78 (2H, quin, J = 6.4 Hz). 13C-NMR (125 MHz, CDCl3) delta (ppm) 171.23, 131.28, 131.16, 130.76, 129.53, 128.50, 128.16, 127.69, 127.27, 126.28, 125.60, 125.48, 125.20, 125.12, 124.62, 122.76, 42.22, 42.08, 37.28, 31.86. IR (cm-1): 3293, 1646, 1544. HR ESI-MS (m/z): calcd. for [C21H19ClNO]+, 336.1150 ([M+H]+); found 336.1161.

The synthetic route of 6276-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fuchi, Yasufumi; Obayashi, Hideto; Sasaki, Shigeki; Molecules; vol. 20; 1; (2015); p. 1078 – 1087;,
Chloride – Wikipedia,
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Reference of 445-13-6, 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 445-13-6 as follows.

General procedure: A substituted aniline (3.0 mmol) and CDI (3.0 mmol) were dissolvedin anhydrous dichloromethane (15 mL) and the reaction was stirred atroom temperature for 1 h under a nitrogen atmosphere. The solvent wasthen removed under reduced pressure, yielding the crude carbamoylimidazolesas solids. The carbamoylimidazoles were then dissolved indichloromethane (5 mL), and added to a solution of amine 13a or 13b(2.0 mmol) in dichloromethane (15 mL). The reaction was then left tostir for 1 h at room temperature. Dichloromethane (50 mL) was thenadded, and the organic layer was washed with water (3×100 mL). Theorganic layer was dried over Na2SO4 and concentrated under reducedpressure. The product was purified on silica gel by step-wise gradientelution with dichloromethane/ethyl acetate (100:0 to 90:10).

According to the analysis of related databases, 445-13-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Al-Zubaidi, Yassir; Pazderka, Curtis; Koolaji, Nooshin; Rahman, Md Khalilur; Choucair, Hassan; Umashankar, Bala; Bourget, Kirsi; Chen, Yongjuan; Rawling, Tristan; Murray, Michael; European Journal of Pharmaceutical Sciences; vol. 129; (2019); p. 87 – 98;,
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Adding a certain compound to certain chemical reactions, such as: 13078-80-3, name is 2-(2-Chlorophenyl)ethanamine, belongs to chlorides-buliding-blocks 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 13078-80-3, Quality Control of 2-(2-Chlorophenyl)ethanamine

N-(2-Fluoropyrimidin-4-yl)-N-methyl-2-phenylpyrimidin-4-amine (442 mg, 1.5 mmol), 2-(2-chlorophenyl)ethanamine (0.32 mL, 2.25 mmol), and dioxane (7 mL) were mixed in a 25 mL roundbottom flask. The mixture was stirred at 100 C. overnight under nitrogen. The reaction was concentrated by vacuum and quenched with saturated NaHCO3 solution. The white solid was filtered and recrystallized to give N2-(2-chlorophenethyl)-N4-methyl-N4-(2-phenylpyrimidin-4-yl)pyrimidine-2,4-diamine as a white solid. MS m/z 417 (MH)+.

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-(2-Chlorophenyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); A1;,
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Synthetic Route of 20850-43-5, 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows.

5-Chloromethyl benzo [1,3]dioxol g, 65.7 mmol) was dissolved in Dimethylformamide. Then, potassium carbonate (18.2 g, 131.4 mmol), sodium iodide (10.8 g, 72.27 mmol) and ethyl benzoylacetate (12.5 mNo., 72.27 mmol) were added thereto and stirred for 5 hours at room temperature. The reaction mixture was extracted with ammonium chloride and ether, the organic layer was separated, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 2- benzo [1,3]dioxol-5-ylmethyl-3-oxo-3-phenylpropionate ethyl ester (16.4 g, 76 %). ¹H NMR (200MHz, CDCl3) : No. 7.98-6.69 (m, 3H), 5.90 (s, 2H), 4.56 (t, J=7.4 Hz, 1H), 4.09 (q, J=7.2 Hz, 2H), 3.26 (d, J=7.4 Hz, 2H), 1.13 (t, J=7.2 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 5-(Chloromethyl)benzo[d][1,3]dioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; JEIL PHARM. CO., LTD.; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; CJ CORP.; WO2005/100303; (2005); A1;,
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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. 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, A new synthetic method of this compound is introduced below., Formula: C7H7ClFN

Compound 38. 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid 2-chloro-4-fluoro-benzylamide (B250110) 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid (61 mg, 0.25 mmol) was dissolved in THF (5 mL), followed by addition of CDI (50 mg, 0.31 mmol). The slurry mixture was stirred at RT for 1 hour. 2-Chloro4-fluorobenzylamine (41 mg, 0.26 mmol) dissolved in THF (2 mL) was added to it. The slurry mixture became a clear yellow solution. The reaction was continued at RT overnight. After removal of the solvent, the residue was washed twice with water (2×10 mL). After filtration, the residue was dissolved in dichloromethane (40 mL) and washed with 0.5 N HCl (20 mL) and water (20 mL). The organic solution was dried over sodium sulfate. Rf value (chloroform, Silica) was 0.55. After filtration through a pad of silica eluted with chloroform, the solvent was removed to afford a semisolid (63 mg, Y=66%).

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; Apogee Biotechnology Corporation; US2007/32531; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5-Chloro-1H-benzo[d][1,2,3]triazole

A solution of 5-chloro-1H-benzotriazole (1.53 g) in THF was added at 0 C. to a mixture of diisopropylic azodicarboxylate (2 mL), triphenyl phosphine (2.9 g) and allyl alcohol (1.4 mL) in THF. After stirring one hour at 0 C., the mixture was concentrated under reduced pressure to give a residue that was purified by chromatography (SiO2, heptane/EA) to afford 2-allyl-5-chloro-2H-benzotriazole (1.02 g, 53%). A mixture of 1-allyl-5-chloro-1H-benzotriazole and 1-allyl-6-chloro-1H-benzotriazole was also recovered (0.9 g, 47%).

The synthetic route of 94-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Soll, Mark David; Hir de Fallois, Loic Patrick Le; Huber, Scot Kevin; Lee, Hyoung Ik; Wilkinson, Douglas Edward; Jacobs, Robert Toms; Beck, Brent Christopher; US2010/125089; (2010); A1;,
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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. 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, A new synthetic method of this compound is introduced below., Formula: C8H9ClO

Acetic anhydride (10 mL) at-10 oC was treated with concentrated nitric acid (>69% pure, 1 mL) and then treated portionwise with 2-CHLORO-4-METHOXY-1-METHYLBENZENE (0. 78G, 5 mmol) at a rate that maintained the internal temperature lower THAN-5 C. The solution was stirred for additional one hour while warming to room temperature, poured into an ice and water mixture, and extracted with ethyl acetate several times. The organic layers were combined, washed with 10% NA2C03 and brine, dried (MGS04), and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 9: 1 hexanes/ethyl acetate to provide 0.75g (71%) of the desired product. MS (DCI) m/e 219 (M+NH4) + ; IH NMR (CDC13, 300 MHz) 8 7.78 (s, 1H), 7.09 (s, 1H), 3.94 (s, 3H), 2.35 (s, 3H).

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; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics