Tag: M.W=100-200

13726-14-2, 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 13726-14-2 as follows.

General procedure: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 13726-14-2, and friends who are interested can also refer to it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, 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. 108-37-2 name is 1-Bromo-3-chlorobenzene, 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.

0.72 g (29.6 mmol) of magnesium dust was immersed in 15 mL of anhydrous tetrahydrofuran, and one iodine was added thereto, and two drops of m-chlorobromobenzene were added dropwise at room temperature. The turbidity was changed by the air gun micro-heating system, and the system was slightly boiled and dropped into 15 mL of tetrahydrofuran and 5.61 g.A mixture of (29.3 mmol) m-bromochlorobenzene was heated and refluxed for 3 hours after the dropwise addition. Decrease to room temperature and use until the next step. To a solution of the format reagent in tetrahydrofuran, 0.34 g (1.8 mmol) of cuprous iodide was added, and the mixture was stirred at room temperature for 1 hour. Slowly drip propargyl alcohol0.66 g (11.7 mmol), after completion of the dropwise addition, was heated to reflux for 24 hours. After cooling, a saturated ammonium chloride solution was added dropwise to adjust pH = 5. Extracted 3 times with 30 mL of ethyl acetate, combined organic phase, washed with saturated sodium hydrogen carbonate solution, washed with saturated sodium chloride solution, anhydrousDry over sodium sulfate. After spin-drying, 10 mL of methanol was added to the system to precipitate a solid, and the solid was taken out and distilled under reduced pressure to give 1.84 g of a pale yellow oily liquid. The yield was 92.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Hebei University of Science and Technology; Zhang Guogang; Du Wei; Zhao Yanli; Feng Xue; Song Miaomiao; Song Wei; Yang Ying; (11 pag.)CN108484535; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

Sodium hydride (992.6 mg, 60% in mineral oil, 24.8 MMOL) was added portionwise to a solution of (2-hydroxy-ethyl)-carbamic acid test-butyl ester (2 g, 12.4 MMOL) in 1-methyl-2- pyrrolidinone (20 ML) AT-2 C, in order to maintain the temperature BELOW 5 C. The mixture was then stirred for 30 minutes, cooled TO-5 C, and a solution of 3-chloro-2-chloromethyl- 1-propene (1.44 ml, 12.4 MMOL) in 1-methyl-2-pyrrolidinone (10 ml) added dropwise in order to maintain the temperature below 3 C. Once addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for a further 18 hours. The reaction mixture was diluted with water and extracted with ether (2X50 ml). The combined organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using ethyl acetate: pentane (10: 90) to give the title compound as a clear oil, 713 mg. H NMR (400MHZ, CDCI3) : No. 1. 46 (s, 9H), 3.51 (d, 2H), 3.72 (d, 2H), 4.00-4. 20 (m, 4H), 4.95 (s, 1H), 5.04 (s, 1H). APCI M/Z 236 [MNA] +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1871-57-4, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/74291; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

112-26-5, 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. 112-26-5 name is 1,2-Bis(2-chloroethoxy)ethane, 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.

It includes the following steps: 1. Feeding To a 2L four-necked flask equipped with a stirrer, a thermometer, and a condenser, which is protected by nitrogen, add 225.3g of triethylene glycol (content 99.6%, 1.5mol), 750g of tetrahydrofuran, and 322g of homemade dichlorotriethylene glycol (content 95.82%) , 1.65mol), stir well and mix evenly. 2. Add potassium hydroxide The temperature was raised with an electric heating mantle, and the reflux started when the temperature reached 70C. 240g (3.96mol) of potassium hydroxide was added to the reaction solution in 12 portions, once every 1h, for a total of 12 additions. The potassium hydroxide is industrial grade with a purity of more than 90%. 3. Insulation reaction After the addition of potassium hydroxide is completed, continue to reflux for 1h. When the gas phase detection of dichlorotriethylene glycol content is less than 0.5%, the reaction can be considered as completed.If the dichlorotriethylene glycol content does not decrease during the gas phase tracking process, it is necessary to continue to add potassium hydroxide until the dichlorotriethylene glycol is consumed. 4. Distilled tetrahydrofuran and water After the heat preservation reaction is completed, the reaction liquid is cooled to below 50C, and the device is changed to a distillation device.Tetrahydrofuran is recovered by atmospheric distillation, and the temperature of the kettle is controlled at 100 at the end of one distillation. Distilled about 750g of tetrahydrofuran and water mixture, with about 3.5% water; Control the pressure of the distillation system to -0.03mpa, and raise the temperature to 100 for 0.5h, Stop the distillation and distill off about 13g of distillate; after the distillation is completed, lower the kettle temperature to below 40. 5. Add dichloromethane Add 600g of methylene chloride to the kettle liquid after distillation and continue to stir at low temperature for 10min; Filter with a Buchner funnel. After the first filtration, wash the filter cake with 300 g of methylene chloride.After washing and filtering, the potassium chloride is slightly yellow, and the salt mass is about 308g. 6. Distilled methylene chloride and water The washing liquid and the filtrate are mixed into a 2000ml four-necked flask. After stirring, 80% sulfuric acid is added dropwise, the system pH is adjusted to 7, and the acid amount is about 4-6g; Build a distillation device, transfer the neutral materials, distill methylene chloride at atmospheric pressure, stop the atmospheric distillation when the temperature of the distillation kettle is about 120C, weigh the distillate and collect it. At this time, the temperature of the system was 120C, the pressure was adjusted to -0.01mpa, and the remaining liquid was distilled under reduced pressure. At this time, the distillate is mainly water, and the vacuum is gradually increased until the pressure is -0.08mpa.The distillate does not flow out, and the temperature is raised to 130C for 0.5h and then cooled, and the distillation is stopped.Among them, about 750 g of distillate was distilled under normal pressure, and 31 g of distillate was distilled under reduced pressure. 7. Distilled crown ether Reduce the temperature of the material to below 60C, transfer to a 1L high vacuum distillation unit, and gradually pump the vacuum to a maximum of about 40pa with an Edward vacuum pump. When the kettle temperature is 150, the distillate begins to flow out. At 180-210C, the distillate flows out faster. The top temperature is stable at 168-172C. When the kettle temperature rises to 230C, the fraction hardly comes out, the top temperature starts to drop, and the distillation ends.Cool down, stop the vacuum pump after the material cools to below 100, and vent the system with nitrogen; 8. Purification of crude products (1) Add acetonitrile Weigh 250g of acetonitrile and transfer to a 1000ml four-necked flask. (2) Add crude crown ether dropwise Under the stirring state, 170g of the above distillate was added with a constant pressure dropping funnel, the dropping process was exothermic, the dropping was completed in about 0.5h, and a lot of turbidity appeared during the dropping process. (3) Heating up After the addition is completed, the temperature is increased by heating, and the temperature of the feed becomes clear after rising to 58C. (4) Cooling and crystallization Then the temperature was lowered. When the temperature dropped to 56, the feed liquid became cloudy. When the temperature continued to drop naturally to 40, the solution was placed in a cold bath at -10 (the temperature gradually decreased to -10) and the crystallization speed was 100 rpm. Stirring is stopped every 1h during the crystallization process, and after standing, the supernatant liquid is taken to detect the content of crown ether in the gas phase.Until the crown ether content no longer decreases to 0.3% stop stirring, about 4h, ready to filter. (5) Filtration and washing Filter with a Buchn…

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Bis(2-chloroethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Patent; Weifang Binhai Petrochemical Co., Ltd.; Zhang Junying; Chen Zhidong; Dou Rongtan; Sun Congming; Yang Wentao; Hao Jiuxiang; Zhou Chengwei; (7 pag.)CN111087382; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 108-70-3, name is 1,3,5-Trichlorobenzene, 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. 108-70-3

General procedure: An oven-dried and argon-flushed pressure tube was charged with 1,3,5-trichlorobenzene, 1,2,4-trichlorobenzene or 1,2,3-trichlorobenzene (0.25 mmol), Pd2(dba)2 (1.25 mol%), cataCXium A (5.0 mol%), boronic acid (1.5 mmol) and K3PO4 (1.5 mmol) followed by anhydrous toluene (4.0 mL). The tube was sealed with a Teflon valve and the reaction mixture was stirred at 110 C for 24 h. The cooled reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography.

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 108-70-3.

Reference:
Article; Reimann, Sebastian; Ehlers, Peter; Sharif, Muhammad; Spannenberg, Anke; Langer, Peter; Tetrahedron; vol. 72; 8; (2016); p. 1083 – 1094;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 39989-43-0 name is 3,5-Dichlorobenzylamine, 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. 39989-43-0

To a solution of 3,5-dichlorobenzylamine (12 mg, 0.068 mmol) in DCM (0.2 mL) was added a solution of 9 (13 mg, 0.054 mmol) in DCM (0.5 mL) at room temperature. The resulting mixture was stirred until all of the 9 had been consumed (within one hr) and then was used straight in the next reaction. MS (ESI) 415 (M+1); HPLC tR 6.00 min.

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

Reference:
Patent; MIMETICA PTY LTD; US2012/141392; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, A common compound: 108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a round-bottom flask equipped with a magnetic stirring bar were added monomeric palladacycle 2 (0.4 mol %), K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 mL). The mixture was heated at 130 C using an oil bath and the progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completing the reaction, the mixture was diluted with n-hexane (30 mL) and H2O. The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from EtOH and H2O. The products were characterized by comparing their mp and IR, 1H and 13C NMR spectra with those reported in the literature.

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, 1-Bromo-3-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hajipour, Abdol Reza; Rafiee, Fatemeh; Rouho, Arnold E.; Tetrahedron Letters; vol. 52; 37; (2011); p. 4782 – 4787;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, Adding some certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 2533-69-9.

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 ¡Á 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

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 2533-69-9.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1871-57-4, 1871-57-4

General procedure: To a cooled solution (5 C) of the corresponding 4,6-O-(R)-benzylidene-d-hexopyranoside derivative (obtained using the procedure describe by our group2c) (35.4 mmol) in dry THF (70 mL) were added, successively, freshly powdered potassium hydroxide (7.0 g, 125 mmol), 18-crown-6 (0.38 g, 1.4 mmol), and 3-chloro-2-chloromethylpropene (4.1 mL, 35.4 mmol). The reaction mixture was stirred at this temperature for 3 h, and left at room temperature until all the starting material had been consumed, as monitored by TLC (5-7 days, approximately), then diluted with dichloromethane (60 mL) and washed successively with water and aqueous saturated solution of sodium bicarbonate, dried (MgSO4), filtered, and the filtrate was evaporated to dryness.

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-Chloro-2-chloromethyl-1-propene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vega-Perez, Jose M.; Vega-Holm, Margarita; Perinan, Ignacio; Palo-Nieto, Carlos; Iglesias-Guerra, Fernando; Tetrahedron; vol. 67; 2; (2011); p. 364 – 372;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, A common compound: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Reference Example 1 To 100 ml of acetic acid solution containing 20 g of 2-benzylamino-4-chloroaniline was added 15 ml of O-methyl-trichloroacetoimidate at 0 to 25 C., and stirred the mixture at room temperature for 3 hours. Then water was added to the reaction mixture, the separated crystals were collected by filtration to obtain 29.6 g of 1-benzyl-6-chloro-2-trichloromethylbenzimidazole in the form of pale brown powder. 1 H-NMR (250 MHz, DMSO-d6) delta ppm: 5.94 (2H, s), 7.04 (2H, d, J=6.5 Hz), 7.25-7.5 (5H, m), 7.88 (1H, d, J=9.0 Hz).

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US5998437; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics