Tag: M.W=100-200

These common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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. Quality Control of Methyl 2,2,2-trichloroacetimidate

Example 7> Preparation of 1H-benzoimidazole-2-carboxylic acid[6-(2-methyl-pyridine-3-yloxy)-pyridine-3-yl]-amide 1,2-phenylenediamine (1 g, 9.25 mmol) was dissolved in acetic acid (30 ), methyltrichloroacetimidate (1.26 , 10.18 mmol) was added to the solution at 0 , and then the mixture was stirred at room temperature. After the reaction was completed, the product was washed, filtered, and dried to obtain 2-trichloromethyl-1H-benzoimidazole.

The synthetic route of Methyl 2,2,2-trichloroacetimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/125923; (2009); A2;,
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Reference of 4090-55-5, These common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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.

In a 250 ml three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 50 ml of acetonitrile, 2-aminothiazole (0.11 mol, 11.0 g) and triethylamine (0.3 mol, 30.3 g) were added and stirred to mix well. Further, a solution of neopentyl glycolphosphoryl chloride (0.1 mol, 18.5 g) in acetonitrile (100 ml) was added dropwise with stirring at 3 C, and the system remains clear and transparent. After the solution was added dropwise, the system was allowed to react at 3 C for 3 h, and then heated to 70 C for 8 h. After completion of the reaction, the solvent was removed by rotary evaporation to obtain a reddish brown solid, which was washed three times with chloroform to remove the triethylamine hydrochloride. After drying, a one-component intumescent flame retardant (PAZ) for epoxy resin was obtained. The yield was 95%.

Statistics shows that 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide is playing an increasingly important role. we look forward to future research findings about 4090-55-5.

Reference:
Patent; Fujian Normal University; Jian Rongkun; Ai Yuanfang; Xia Long; Pang Fuqu; (9 pag.)CN109400649; (2019); A;,
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Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39989-43-0, 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. 39989-43-0, name is 3,5-Dichlorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 30 2-[3,5-Dichlorobenzylamino]-4-[benzimidazol-1-yl]pyrimidine 2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine was reacted with 3,5-dichlorobenzylamine according to the procedure described in EXAMPLE 1, Step C to afford the title compound. Mass Spectrum (EI): m/e 370.3 (M+1). 1H NMR (500 MHz, CDCl3): delta 8.58 (s, 1H); 8.45 (d, J=5.5 Hz, 1H); 7.98 (br s, 1H); 7.86 (m, 1H); 7.38 (m, 2H); 7.31 (s, 2H); 6.89 (d, J=5.5 Hz, 1H); 5.88 (br s, 1H); 4.72 (d, J=6.4 Hz, 2H).

The synthetic route of 3,5-Dichlorobenzylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6498165; (2002); B1;,
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Chlorides – an overview | ScienceDirect Topics

Application of 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.

This was prepared from MA1-012 (0.531 g) and 3-methoxy-4-chloroaniline (0.473 g) using procedure A (reaction time, 16 h) to give the title compound as a white solid (0.202 g, 23%). Mp: 143-144 C. lH NMR (400 MHz, DMSO-ifc): delta 8.93 (s, IH, disappeared on D20 shake), 8.07 (s, IH), 7.53 (d, / = 2.3 Hz, IH), 7.37 (d, / = 8.6 Hz, IH), 7.31 (dd, / = 8.6, 2.3 Hz, IH), 3.83 (s, 3H), 2.61 (q, J = 7.4 Hz, 2H), 1.17 (t, / = 7.4 Hz, 3H). HPLC-MS (ESI+): m/z 300.1 [70%, (M37C135C1+H)+], m/z 298.1 [100%, (M35C135C1+H)+]. Further elution gave the bis- adddition side product MA1-025B (109 mg, 9%) as a yellow solid, Mp: 201 C (dec). HPLC: 99% [tR = 8.1 min, 65% MeOH, 35% water (with 0.1% TFA), 20 min]. lH NMR (400 MHz, DMSO-ifc): delta 9.20 (s, IH, disappeared on D20 shake), 8.48 (s, IH, 40% reduced on D20 shake), 7.97 (s, IH), 7.56 (d, / = 2.3 Hz, IH), 7.43 (d, / = 2.3 Hz, IH), 7.38 (dd, / = 8.6, 2.3 Hz, IH), 7.32 (d, / = 8.7 Hz, IH) 7.29 (dd, / = 8.6, 2.3 Hz, IH), 7.15 (d, / = 8.7 Hz, IH), 3.74 (s, 3H), 3.60 (s, 3H), 2.57 (q, / = 7.4 Hz, 2H), 1.18 (t, / = 7.4 Hz, 3H). HPLC-MS (ESI+): m/z 421.1 [70%, (M37C135C1+H)+], 419.2 [100%, (M35C135C1+H)+]. LC-MS (ESI+): 421.1 [70%, (M37C135C1+H)+], 419.1 [100%, (M35C135C1+H)+]. HRMS (ESI+): m/z calcd for C20H20CI2N4O2 (M+H)+ 1035.Pr ocedure A: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.) and substituted aniline (1.15 equiv.) in MeOH/water (1 : 1.5, 0.2 M) was stirred at 45 C. The reaction time is indicated below. Upon cooling to ambient temperature, the desired product precipitated and was filtered, washed with MeOH/water (1 : 1.5, 20 mL), and dried. 2,5-Dichloro-/Y4-(4-[/Y-(l,l-dimethylethyl)sulfamoyl]phenyl)pyrimidin-4-amine (SG1-182): This was prepared from 2,4,5-trichloropyrimidine (0.500 g) and SG1-177 (0.715 g) using procedure A (stirred for 4 d). The crude solid was purified via flash chromatography (S1O2) eluting with hexanes/EtOAc (0: 10 to 4:6 v/v) to provide the title compound as a tangerine-colored solid (0.590 g, 58%). Mp: 180-181 C. NMR (400 MHz, DMSO-ifc): delta 9.73 (s, IH, disappeared on D20 shake), 8.46 (s, IH), 7.80 (s, 4H), 7.48 (s, IH, disappeared on D20 shake), 1.09 (s, 9H). HPLC-MS (ESI+): m/z 773.1 [10%, (MCl35Cl37+M35Cl35Cl+Na)+], 379.1 [10%, (MC137C137+H)+], 377.1 [70%, (MC135C137+H)+], 375.1 [100%, (M35C135C1+H)+].

According to the analysis of related databases, 13726-14-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 118-69-4, These common heterocyclic compound, 118-69-4, name is 2,6-Dichlorotoluene, 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.

5 g of the following catalyst particles, as described in examples 3 and 4, were loaded in the reactor along with the diluent corundum particles (1: 1 by weight) and tested the influence of addition of ethyl bromide (2 % VN) in presence and absence of water vapour. The reaction was performed under the following conditions. A reaction temperature of 350 to [400C] was used. The mole ratio 2,6-DCT : H20 : NH3: air: N2 was 1: 15: 3-4: 21: 0-29. Molar concentration of 2,6-DCT is 1.4 to 3.8 %.

Statistics shows that 2,6-Dichlorotoluene is playing an increasingly important role. we look forward to future research findings about 118-69-4.

Reference:
Patent; TESSENDERLO CHEMIE S.A.; WO2003/101939; (2003); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 4584-46-7,Some common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, molecular formula is C4H11Cl2N, 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.

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2 g, 10.31 mmol), cesium carbonate (6.72 g, 20.61 mmol) and 2-chloro-N,N-dimethylethanamine hydrochloride (2.227 g, 15.46 mmol) were suspended in acetonitrile (30 mL) and the mixture was heated at reflux for 5 h, then cooled to room temperature, diluted with Et2O and filtered. The filtrate was concentrated in vacuo to give N,N-dimethyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethanamine dimethyl{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl}amine (2.61 g, 9.84 mmol, 95% yield) as an amber oil which was used in the next step without further purification

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

Reference:
Patent; Demont, Emmanuel Hubert; Garton, Neil Stuart; Gosmini, Romain Luc Marie; Hayhow, Thomas George Christopher; Seal, Jonathan; Wilson, David Matthew; Woodrow, Michael David; US2012/208798; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route 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.

a) 4-Bromo-3-chloro-5-fluoroaniline3- Chloro-5-fluoroaniline (2061 mmol, 300 g) was dissolved in ACN (3000 ml) and the solution cooled to 0C. NBS (2061 mmol, 367 g) was added to the reaction mixture in small portions keeping the temperature below 10 C. Reaction mixture was stirred at 10 +/- 5 C for 3.5 h. 10 % Aqueous NaHS03 was added and the reaction mixture was concentrated under vacuum to remove organic solvents. Water and DCM was added, stirred for 15 min and the phases were separated. The water phase was extracted with DCM. The combined organics were washed with water. The organic phase was evaporated. 2-Propanol was added to the residue and distilled until the steam temperature was 80 C. Water was added and the temperature was kept at 40 +/- 10 C. The mixture was cooled to 5 C and stirred for 4 h. The precipitate was removed by filtration, washed with water and dried under vacuum. 440.7 g of the title compound was obtained. 1 H-NMR (400 MHz, DMSO-c/6): delta 5.87 (s, 2H), 6.42-6.49 (m, 1H), 6.62-6.66 (m, 1H).

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; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 6223-78-5, name is 2,5-Dichloro-2,5-dimethylhexane, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H16Cl2

For comparison in the biological evaluation (Fig. 1 and 2) of compounds 1 – 3, [8 and 9] and 30-32, [8b and 9b] an authentic sample of bexarotene and its ketone analog (33a) were synthesized, following the reported route (Boehm, et al. “Synthesis and Structure-Activity Relationships of Novel Retinoid X Receptor-Selective Retinoids.” J. Med. Chem. 1994, 37, 2930-2941 ): a seven step, convergent synthesis that gave a 29% overall yield of bexarotene. The first sequence of steps to bexarotene concerned the SN1 conversion of 2,5-dimethyl-2,5-hexanediol (33b) to 2,5-dichloro-2,5- dimthylhexane (34) by HCI, and the subsequent aluminum trichloride catalyzed Friedel-Crafts alkylation of toluene to give 1 ,2,3,4-tetrahydro-l .l A4,6-pentamethylnapthalene (35) in 68% yield over two steps (Scheme 1 ).

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 6223-78-5.

Reference:
Patent; ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA, ACTING FOR AND ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl E.; JURUTKA, Peter W.; MARSHALL, Pamela A.; VAN DER VAART, Arjan; WO2011/103321; (2011); A1;,
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. 6940-78-9, name is 1-Bromo-4-chlorobutane, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-4-chlorobutane

General procedure: K2C03 (1.0 eq.) and the dihaloalkane (XIII, 1.0 eq.) were added to a solution of the appropriatethio-derivative XIV (1.0 eq.) in DMF (0.5 mL per mmcl XIII). The reaction mixture was stirred under nitrogen atmosphere for 5 h at rt. The crude reaction mixture was filtered and concentrated under reduced pressure. Sat. aq. NaHCO3 solution (1.0 mL per mmol XIII) was added and the mixture extracted with Et20 (3 x 1.0 mL per mmol XIII). The combined organic layers were evaporated on silica. Pure compound XV was obtained by column chromatography using theTeledyne ISCO apparatus (cyclohexane:EtOAc). The title compound was obtained according to the General Procedure VIII (Step 1) starting from1-bromo-4-chlorobutane (8.57 g, 50.0 mmol) and thiophenol (5.51 g, 50.0 mmol). Colorless liquid(8.06 g, 80%). 1H NMR (400 MHz, CDCI,) 6 1.79 – 1.88 (m, 2H), 1.91 – 1.99 (m, 2H), 2.98 (t, i = 7.1Hz, 2H), 3.57 (t, J = 6.5 Hz, 2H), 7.17 – 7.24 (m, 1H), 7.28 – 7.34 (m, 2H), 7.35 – 7.39 (m, 2H). MS(ESI) m/z: non-ionizable compound under routine conditions used.

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; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI PARMA; PIOMELLI, Daniele; PIZZIRANI, Daniela; BACH, Anders; SCARPELLI, Rita; MELZIG, Laurin; MOR, Marco; (72 pag.)WO2015/173169; (2015); 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. 2106-02-7, name is 2-Chloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-4-fluoroaniline

To a solution of 197 mg (1.35 mmol) of 2-chloro-4-fluoroaniline and 0.20 ml (1.42 mmol) of triethylamine in 5 ml of ethyl acetate was added dropwise a solution of 400 mg (1.29 mmol) of ethyl 8-chlorosulfonyl-1,4-dioxaspiro[4.5]dec-7-ene-7-carboxylate obtained in (1c) in 3 ml of ethyl acetate with stirring under ice-cooling, followed by stirring at room temperature for 48 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane : ethyl acetate = 3:1), and the resulting solid was further washed with a mixed solution of hexane-isopropyl ether (1:1) to give 325 mg of the title compound as a white powder (yield: 60%). Melting point 117-119C 1H-NMR spectrum (400 MHz, CDCl3) deltappm: 7.67 (1H, dd, J=9Hz, 5Hz), 7.16 (1H, dd, J=8Hz, 3Hz), 7.05-6.98 (2H, m), 6.83 (1H, s), 4.43-4.41 (1H, m), 4.26-4.01 (5H, m), 3.95-3.88 (1H, m), 2.56-2.45 (2H, m), 2.24-2.11 (1H, m), 1.88-1.80 (1H, m), 1.27 (3H, t, J=7Hz).

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1935879; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics