Tag: M.W=100-200

Synthetic Route of 83121-15-7,Some common heterocyclic compound, 83121-15-7, name is 3,5-Dichloro-2,4-difluoroaniline, molecular formula is C6H3Cl2F2N, 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.

EXAMPLE 3 2,4-Difluoro-3,5-dichlorophenyl isocyanate Hydrogen chloride was passed into a well-stirred solution of 39.6 gm (0.20 mol) of 2,4-difluoro-3,5-dichloroaniline in 400 ml of toluene until a precipitate no longer separated out. The heterogeneous mixture thus obtained was cooled to 5 to 10 C. At this temperature, 40 gm (0.4 mol) of phosgene were passed in, with stirring. The mixture was then heated slowly, with stirring, so that after about two hours a temperature of 100 to 105 C. was reached. Stirring was then continued for seven hours at this temperature. During this time, a clear solution was formed, and hydrogen chloride was liberated. Nitrogen was then passed into the mixture for one hour at the same temperature to drive off the excess phosgene. Thereafter the solvent was distilled off, in vacuo at the end. The crude product which remained was distilled in a water pump vacuum. Yield: 35.4 gm (0.158 mol; 79% of theory), B.p.: 100-104 C./20 mbar.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloro-2,4-difluoroaniline, its application will become more common.

Reference:
Patent; Celamerck GmbH & Co., KG; US4622340; (1986); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, A new synthetic method of this compound is introduced below., Safety of 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine

Appropriate 6-chloro-[1 ,2,4]triazolo[4,3-b]pyridazine (1 eq) or 6-chloro- [1 ,2,4]triazolo[3,4-a]phtalazine (1 eq), potassium carbonate (3 to 4 eq) and the appropriate phenol, thiophenol (1 to 4 eq, 1 eq is preferentially used when R1 = CI) were dissolved in ?,?-dimethylformamide under nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature or at 100-1 10C, or 5-30 minutes at 100-170C on microwave irradiation. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2S04, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel, precipitated, triturated in the appropriate solvent, or used without further purification to obtain the desired 6-aryl-[1 ,2,4]triazolo[4,3-b]pyridazine, or 6-aryl-[1 ,2,4]triazolo[3,4-a]phtalazine.This protocol was used to prepare the following compounds: Cpd.1 -1 , Cpd.1 -3, Cpd.1 -4, Cpd.1 -7, Cpd.1 -8, Cpd.1 -9, Cpd.1 -10, Cpd.1 -1 1 , Cpd.1 -12, Cpd.1 -13, Cpd.1 -14, Cpd.2-1 , Cpd.2-3, Cpd.2-4 and other compounds of the invention that contain a biphenyloxy, a pyridinylphenyloxy, a thiazolylphenyloxy, or a thiopenylphenyloxy group in the 6-substituted position of the [1 ,2,4]triazolo[4,3-b]pyridazines or 6-substituted position of the [1 ,2,4]triazolo[3,4-a]phthalazine (but further information about conditions and purification are reported in Tables of Example 2).

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; GENFIT; BOUROTTE, Maryline; DELHOMEL, Jean-Francois; DUBERNET, Mathieu; GOUY, Marie-Helene; WO2013/45519; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 139512-70-2, 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. 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 0.37 g (1 mmol) of compound 2 and 0.16 g (1 mmol) of 4-chloro,5-fluoro-o-phenylenediamine in 4 mL of polyphosphoric acid was stirred at 200 C. for 4 h and poured into 60 mL of dilute NH4OH. It was extracted with three 60 mL portions of ethyl acetate. The combined organic extracts were washed with 60 mL of brine and concentrated. The residue was chromatographed eluting with a gradient of from 2 to 10% methanol (MeOH) in dichloromethane (DCM) plus 1% NH4OH to give 0.06 g of compound 3a and 0.14 g of compound 3b. 3a: Calcd m/z for C26H23BrFN3.H+=478; found m/z=478. 3b: Calcd m/z for C26H22BrClFN3.H+=512; found m/z=512.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-5-fluorobenzene-1,2-diamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Schering Corporation; US2005/49269; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 104-52-9, name is 3-Phenylpropyl Chloride, 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 104-52-9, name: 3-Phenylpropyl Chloride

15.5 g (0.10 mol) of 3-phenylchloropropane, 4.1 g (0.05 mol) of ethylamine hydrochloride, 0.2 g of tetrabutylammonium bromide and 50 ml of a sodium hydroxide solution (35% to 40%) were placed in a 250 ml flask.Stirring heated to 85-90 C, insulation reaction, TLC tracking.After completion of the reaction, the aqueous layer was extracted three times with ethyl acetate, and the organic layers were combined.Add anhydrous sodium sulfate drying.The filtrate was concentrated under reduced pressure to give 12.4 g of a brownish yellow liquid.Yield: 88%.

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, 3-Phenylpropyl Chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hebei Kaisheng Pharmaceutical Technology co., LTD; ZHAO, KAI; HOU, JIANPING; ZHAO, YAFENG; YUAN, HONGZHONG; ZHAO, XIAOXIAN; JIAN, YONGXUE; (5 pag.)CN103508898; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 20850-43-5, 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[[00244]] To a solution of [4- (8-AZA-BICYCLO] [3.2. [1] OCT-3-] ylamino)-6-chloro-1-(2, 2, [2-TRIFLUORO-ETHYL)-LH-QUINAZOLIN-2-] one (149 mg, 0.320 mmol) in DMF (10 mL) was added triethylamine (0.3 mL) and 5-Chloromethyl-benzo [1, 3] dioxole [(0.] 061 mL, 0.480 mmol). The solution was heated to 50 C and stirred for 6 hrs. The reaction was partitioned between ethyl acetate and water and the organic phase was washed an additional 2 x with water and brine, dried over [NA2SO4,] filtered, and concentrated. The crude residue was purified by flash chromatography (gradient elution: [0-20%] MeOH/dichloromethane) to provide 99 mg white solid [(60%). 1H] NMR (300 MHz, CDCl3) 8 ppm 2.10 (m, 4 H), 2.32 (m, 2 H), 3.56 (m, 3 H), 3.77 (s, 2 H), 4.87 (m, 2 H), 5.96 (s, 2 H), 6.77 (d, J = 8.0 Hz, [1] H), 6.83 (m, [1] H), 6.95 (d, J = 8.1 Hz, [1] H), 7.17 (m, 2 H), 7.56 (dd, J = 2.3, 8.9 Hz, [1] H), 7.91 (s, [1] H); MS (ESI [+Q1MS)] m/z 522 [[M+2H] +]

The synthetic route of 5-(Chloromethyl)benzo[d][1,3]dioxole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2003/106452; (2003); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 106-39-8, 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 106-39-8 as follows.

General procedure: CS2 (1.3 mmol, 0.07 mL) was added to a stirred solution of KCN (1.1 mmol, 0.07 g) in DMF (1 mL) at room temperature. After 15 min, bromobenzene (1.0 mmol, 0.10 mL), K2CO3 (1.0 mmol, 0.14 g) and CuI (20 mol%, 0.038 g) were added and the mixture stirred at 120 C. Upon reaction completion (TLC, 6.5 h), the mixture was cooled to room temperature, diluted with H2O (1 mL), and extracted with n-hexane/ethyl acetate (1:1, 4 ¡Á 1 mL). The combined organic extracts were concentrated and the residue purified by silica gel column chromatography using n-hexane as eluent to give the pure diphenyldisulfane in 90% (0.098 g) yield.

According to the analysis of related databases, 106-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abbasi, Mohammad; Nowrouzi, Najmeh; Borazjani, Saeedeh Ghassab; Tetrahedron Letters; vol. 58; 45; (2017); p. 4251 – 4254;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2613-34-5,Some common heterocyclic compound, 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, molecular formula is C6H4ClF2N, 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.

General procedure: The 4-chloro-6, 7, 8-trimethoxyquinazoline (7) (0.4 mmol) and aromatic amines (0.4 mmol) inisopropyl alcohol (5 mL) were stirred at reflux temperature for about 4 to 24 h and disappearance of 4-chloro-6, 7, 8-trimethoxyquinazoline (7) was monitored by TLC using ethyl acetate and hexanes. TLC tracking to no raw material points (expansion agent: petroleum ether: ethyl acetate = 1:1, V/V), stop the reaction, after cooling, solid precipitated, filtrated, recrystallized and dried to give 6, 7, 8- trimethoxyl-4-anilinoquinazoline (Tg1-14).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2,4-difluoroaniline, its application will become more common.

Reference:
Article; Liu, Fang; Huai, Ziyou; Xia, Guotai; Song, Liuping; Li, Sha; Xu, Yulan; Hong, Kangjun; Yao, Mingyue; Liu, Gang; Huang, Yinjiu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2561 – 2565;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, molecular formula is C7H7ClFN, 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. Formula: C7H7ClFN

General procedure: To an oven-dried screw-capped reaction tube equipped with a magnetic stirring bar theketone (1 eq), amine (2.8 eq), 4-nitrophenyl azide (2 eq), acetic acid (10 mol%) and 4 Amolecular sieves (50 mg) were added. The reaction mixture was dissolved in toluene(0.3M) and stirred at 100 C for 18 hours. The crude reaction mixture was then directlypurified by column chromatography (silica gel) at first with dichloromethane (DCM) aseluent to remove all 4-nitroaniline formed during the reaction followed by using a mixtureof heptane and ethyl acetate as eluent to afford the corresponding 1,2,3-triazoles asyellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15205-15-9, its application will become more common.

Reference:
Article; Karypidou, Konstantina; Ribone, Sergio R.; Quevedo, Mario A.; Persoons, Leentje; Pannecouque, Christophe; Helsen, Christine; Claessens, Frank; Dehaen, Wim; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3472 – 3476;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4863-91-6, 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. 4863-91-6 name is 3-Chloro-5-fluoroaniline, 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.

Example 4: Synthesis of Compound 33 33 Compound 33 Compound 33 [099] A flame-dried flask was charged with 2-bromonitrobenzene (50 mg, 0.25 mmol, 1 equiv) tris(dibenzylideneacetone)dipalladium (11.3 mg, 0.0012 mmol, 5 mol%), racemic 2,2′- bis(diphenylphosphino)-l, l’-binaphthyl (11.5 mg, 0.0019 mmol, 7.5 mol%), and cesium carbonate (163.1 mg, 0.50 mmol, 2 equiv). The flask was degassed and purged with nitrogen. Toluene (2.88 mL) was added, followed by 2-chloro-4-fluoroaniline (35.3 mg, 0.25 mmol, 1 equiv). The reaction was heated to 100C with a reflux condenser and stirred for 12 h. The mixture was cooled to room temperature, filtered through a pad of celite, dried over MgS04 and concentrated under reduced pressure. Purification by flash chromatography on silica gel (9: 1 hexanes:ethyl acetate) afforded the desired aniline 33 as an orange solid (58 mg, 88% yield): XH NMR (400 MHz, Acetone-d6) 9.27 (bs, 1H), 8.18 (d, J= 8.5 Hz, 1H), 7.63 (d, J = 8.6 Hz, 1H), 7.52 (d, J = 8.6 Hz, 1H), 7.28 (s, 1H), 7.17 (dt, J= 2.2 Hz, 10.4 Hz, 1H), 7.04 (m, 2H); 13C NMR (100 MHz, Acetone-d6) 164.2 (d, J = 245.7 Hz), 144.0 (d, j = 1 1.8 Hz), 140.9, 136.7, 136.6, 136.2 (d, J= 13.0 Hz), 127.2, 120.7, 1 18.9, 1 18.9, 1 12.0 (d, J= 25.4 Hz), 108.6 (d, J = 24.5 Hz);LCMS (ESI) calc’d for [Ci2H7ClFN202]”([M-H]”): m/z 265.0, found 265.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 886762-39-6, These common heterocyclic compound, 886762-39-6, name is 3,4-Dichloro-2-fluoroaniline, 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.

To a stirred solution of [4-chloro-7-(2,2-dimethylpropanoyloxy)quinazolin-6-yl] 2,2-dimethylpropanoate (6.6 g, 18.1 mmol) in DCE (60 mL) was added HCI, 4 M in dioxane (9 mL) followed by 3,4-dichloro-2-fluoroaniline (3.1 g, 17.2 mmol) and the resulting mixture was stirred at 70 C for 1 .5 h. The mixture was then cooled to room temperature and diluted with diethyl ether. The resulting suspension was filtered to collect the desired product (8.5 g, 92%).

The synthetic route of 886762-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TRILLIUM THERAPEUTICS INC.; SLASSI, Abdelmalik; DOVE, Peter; (124 pag.)WO2016/123706; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics