Author: Jessica.F

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. 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, A new synthetic method of this compound is introduced below., Recommanded Product: 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline

To THF (15 mL) were added (+/-)-trans-methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (0.68 g, 3.69 mmol), 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (1.13 g, 2.46 mmol) and DIPEA (4.5 mL, 24.6 mmol). The mixture was stirred at 65 C overnight. The reaction mixture was quenched with water (100 mL). The resulting mixture was extracted with ethyl acetate (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL), dried over ahydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 4/1) to give the title compound as a white solid (862 mg, 17%).MS (ESI, pos. ion) m/z: 350.2 [M+H]+1H NMR (400 MHz, CDC13) (ppm): 4.75 (d, J = 5.1 Hz, 1H), 4.43 (t, J = 5.3 Hz, 1H), 3.77 (s, 3H), 2.68 (t, J= 5.9 Hz, 2H), 2.35 (d, J= 5.7 Hz, 1H), 2.29-2.23 (m, 2H), 2.05 (s, 1H), 1.96 (d, J = 2.5 Hz, 1H), 1.89-1.76 (m, 6H), 1.67-1.54 (m, 5H), 1.26 (d, J= 7.1 Hz, 1H).

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 62356-27-8,Some common heterocyclic compound, 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene, molecular formula is C7H6BrCl, 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 4 6-(2-Bromo-6-chlorophenyl)-2-methylpyrido[2,3-d]-pyrimidin-7-amine A mixture of 20.0 g of 2-bromo-6-chlorotoluene [J. B. Cohen and M. S. Raper, J. Chem. Soc., 85: 1268 (1904)] and 18.0 g of N-bromosuccinimide in 200 ml of carbon tetrachloride is heated to reflux in the presence of 10 mg. of benzoyl peroxide as catalyst. After 24 hours, the mixture is cooled and filtered, and the filtrate is concentrated to dryness to give a lachrymatory oil which solidifies on standing, mp 56-60 C. Spectral data confirms that this crude product is primarily 6-chloro-alpha,2-dibromotoluene which is used in the subsequent reaction without further purification. A solution of 31.3 g of the crude 6-chloro-alpha,2-dibromotoluene in 100 ml of warm ethanol is treated with a solution of 6.7 g of potassium cyanide in 10 ml of water and the mixture is heated at reflux for 4 hours. The crude product is isolated by pouring the cooled reaction mixture into water and filtering the resulting precipitate. Recrystallization of this solid from aqueous ethanol then gives 12.4 g of 2-bromo-6-chlorophenylacetonitrile, mp 82-84 C. Following the procedure for Example 1, 2-bromo-6-chlorophenylacetonitrile is condensed with 4-amino-2-methylpyrimidin-5-carboxaldehyde to give 6-(2-bromo-6-chlorophenyl)-2-methylpyrido[2,3-d]-pyrimidin-7-amine, mp 272-274 C., after recrystallization from acetonitrile.

The synthetic route of 62356-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4271164; (1981); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 344-65-0, name is 1-Bromo-4-chloro-2-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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. Computed Properties of C7H3BrClF3

General procedure: A 1,4-Dioxane solution (8 mL) of 10 (1.0 mmol), arylboronic acid 2 (1.0 equiv.), K3PO4, and Pd(PPh3)4 (5 molpercent) was heated at 75 C for 4 h. After cooling to room temperature, H2O was added and the reaction mixture was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (pure n-heptane).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 344-65-0, its application will become more common.

Reference:
Article; Ali, Iftikhar; Siyo, Baraa; Hassan, Zahid; Malik, Imran; Ullah, Ihsan; Ali, Asad; Nawaz, Muhammad; Iqbal, Jamshed; Patonay, Tama?s; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 145; (2013); p. 18 – 34;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 104-52-9, 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. 104-52-9, name is 3-Phenylpropyl Chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 2 Preparation of N-methyl 3-(o-methoxyphenoxy)-3-phenylpropylamine hydrochloride. A reaction mixture consisting of 1000 g. of 3-chloropropylbenzene, 1500 g. of N-bromosuccinimide, 5 g. of benzoyl peroxide and 6 l. of carbon tetrachloride were placed in a 12 l. 3-neck, round-bottom flask equipped with stirrer and condenser. The reaction mixture was stirred and heated until an exothermic reaction began. The heat source was then removed, and the refluxing of reaction mixture controlled by external cooling. After the reaction had been completed as noted by the disappearance of the N-bromosuccinimide, the reaction mixture was cooled and crystalline succinimide collected by filtration. The succinimide filter cake was washed with carbon tetrachloride. The combined filtrate and wash was concentrated in vacuo. The residue comprising 3-chloro-1-bromopropylbenzene obtained in the above reaction was shown by a NMR to be the desired material and was used without further purification.

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; Eli Lilly and Company; US4018895; (1977); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2613-34-5, 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. 2613-34-5, name is 3-Chloro-2,4-difluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3-chloro-2,4-difluoroaniline (1 g, 6.1 mmol) in DMF (20 mL) was added NIS (1.7 g, 7 mmol) at RT. The mixture was stirred at RT for 3 h. The reaction mixture was diluted with water (20 mL) and extracted with EA (10 mL x 3). The combined organic phases were dried over Na2S04, filtered and concentrated. The crude product was purified by silica gel chromatography (PE/EA=lO: l) to give 3-chloro-2,4-difluoro-6-iodoaniline (1.1 g, 62% yield) as a yellow oil. 1H NMR (CDC13, 400 MHz): d 7.09-7.09 (m, 1H).

The synthetic route of 3-Chloro-2,4-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PADFORWARD LLC; KANOUNI, Toufike; (109 pag.)WO2019/152883; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1871-57-4, A common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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.

Sodium hydride (60% in mineral oil) (0.92 g, 23.05 mmol) was dissolved in DMF (20 mL) at 0 C and 3-chloro-2-(chloromethyl)prop-1-ene (0.81 mL, 7.68 mmol) was added in portions. Separately, tert-butyl N-[2-(tert-butoxycarbonylamino)ethyl]carbamate (2.00 g, 7.68 mmol) was dissolved in THF (20 mL) and added. The reaction mixture was stirred at 20 C for 3 h. The volatiles were removed under reduced pressure. The reaction was diluted with water (50 mL) and then extracted with EtOAc (3 x 80 mL). The organic extracts were combined passed through a phase separation cartridge and the volatiles were removed under reduced pressure. The crude product was dissolved in DCM and purified via silica gel chromatography eluting with 0-50% EtOAc in heptane to afford di-tert-butyl 6-methylene-1,4-diazepane-1,4-dicarboxylate 28 (1.01 g, 42%) as a white solid. 1H NMR (400 MHz, CDCl3) 1.39-1.5 (m, 18H), 3.39-3.56 (m, 4H), 3.80 – 4.06 (m, 4H), 4.86 – 5.13 (m, 2H); 13C NMR (400 MHz, DMSO, 100 C) 28.58, 48.49, 52.21, 79.50, 111.89, 144.82, 154.74; HRMS [M+H]+ measured 335.1940, C16H28N2O4 requires 335.1947.

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; Watson, David W.; Gill, Matthew; Kemmitt, Paul; Lamont, Scott G.; Popescu, Mihai V.; Simpson, Iain; Tetrahedron Letters; vol. 59; 51; (2018); p. 4479 – 4482;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, molecular formula is C8H7ClO2, 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. category: chlorides-buliding-blocks

Step 2. Synthesis of 3-(benzo[d][1 ,3]dioxol-5-ylmethyl)-5-(3-nitrobenzylidene)imidazo- lidine-2,4-dione; DBU (3.82 mmol, 0.961 g) is added into solution of 5-(3-nitrobenzylidene)imidazolidine-2,4- dione (3.19 mmol, 0.743 g) at O’O and the solution left to warm to room temperature. 5- (Chloromethyl)benzo[d][1 ,3]dioxole (6.37 mmol, 2.174 g, 50% soln in CH2CI2) is added and the reaction mixture stirred for 3 hours. Subsequently 0.5 M HCL solution is added and extracted with ethylacetate (2 x 50 ml_) dried over MgSO4 and the solvent removed under reduced pressure. The obtained product is recrystallized from diisopropylether to afford 0.13 (1 1%) of 3-(benzo[d][1 ,3]dioxol-5-ylmethyl)-5-(3-nitrobenzylidene)imidazo-lidine-2,4-dione.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20850-43-5, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICAL D.D.; WO2008/43733; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 63624-28-2, 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 63624-28-2 as follows.

0.5 g of 60% sodium hydride in oil is added to a mixture of 3.6 g of 5-chloro-1H-indole-2,3-dione in 20 ml of DMF, and the mixture is stirred for 30 minutes at 20 C. 4.8 g of 2,4-dimethoxybenzenesulphonyl chloride are then added and the mixture is stirred at 20 C. for 1 hour. The resulting mixture is concentrated under vacuum (1.3 Pa), the residue is extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is triturated in iso ether and the precipitate formed is filtered off by suction. 2.9 g of the expected product are obtained after crystallization from hot EtOAc, m.p.=194.5 C.

According to the analysis of related databases, 63624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Di Malta, Alain; Garcia, Georges; Roux, Richard; Schoentjes, Bruno; Serradeil-Le Gal, Claudine; Tonnerre, Bernard; Wagnon, Jean; US2004/180878; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13918-92-8, 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 13918-92-8 as follows.

To a solution of 5-bromo-2-methoxypyridin-3-amine (10.15 g, 50 mmol) in pyridine (50 mL) was added 2,4-difluorobenzene-1-sulfonyl chloride (11.68 g, 60 mol) slowly at 0 C. The mixture was stirred at rt for 19 hours and concentrated in vacuo. The residue was dissolved in MeOH (100 mL) and NaOH (2.50 g, 60 mmol). The resulted mixture was stirred at rt for 12 hours and concentrated in vacuo. The residue was dissolved in H2O (50 mL) and the resulted mixture was extracted with DCM (100 mL¡Á3). The combined organic phases were washed with brine (100 mL¡Á3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a brown solid (16.90 g, 89.1%). [0304] MS (ESI, pos. ion) m/z: 379.0 [M+H]+.

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1020198-58-6, name is 2-Bromo-1-chloro-3,5-difluorobenzene, 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 1020198-58-6, Formula: C6H2BrClF2

A mixture of 2-bromo-1-chloro-3,5-difluorobenzene (800 mg), bis(pinacolato)diborone (1.1 g), bis(triphenylphosphine)palladium chloride (123 mg), triphenylphosphine (92 mg), potassium acetate (1.0 g), and 1,4-dioxane (24 mL) was heated under stirring in an oil bath at 100 C. for 18 hours. The reaction mixture was returned to room temperature, the insoluble materials were separated by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain 2-(2-chloro-4,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (242 mg).

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; Kinoyama, Isao; Miyazaki, Takehiro; Koganemaru, Yohei; Washio, Takuya; Hamaguchi, Wataru; US2012/142727; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics