Month: July 2021

Reference of 823-57-4,Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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.

(1H-indol-2-yl)boronic acid ((1H-indol-2-yl) boronic acid) (100 g, 0.621 mol) 2-Bromo-5-chloroaniline (2-bromo-5-chloroaniline) (115 g, 0.558 mol) Was dissolved in toluene (Toluene), EtOH, H2O 1000 mL: 200 mL: 200 mL , Pd (PPh3) 4 (35.8 g, 0.031 mol) and NaHCO3 (156.5 g, 1.863 mol) were added and stirred at 100 ° C for 3 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO 4, the solvent was removed using a rotary evaporator to obtain Compound 1-1 (110 g, 74percent) in liquid form.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; L Ti Material Co., Ltd.; Ji Hye-su; Oh Han-guk; Lee Yun-ji; Jeong Won-jang; Choi Jin-seok; Choi Dae-hyeok; (217 pag.)KR2019/33911; (2019); A;,
Chloride – Wikipedia,
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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 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

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

13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine

a) ierf-Butyl 4-[(3-bromoimidazo[1 ,2-b]pyridazin-6-yl)amino]piperidine-1 -carboxylateA solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (3.00 g, 12.9 mmol 1.0 eq) in NMP (15 ml_) was treated with te/f-butyl 4-aminopiperidine-1 -carboxylate (5.10 g, 25.8 mmol, 2.0 eq), DIPEA (5.60 mL, 32.3 mmol, 2.5 eq) and heated at 130C for 5 h. The reaction mixture was diluted with DCM (100 mL) and washed with de-ionised water (3 x 150 mL). The separated organic was concentrated in vacuo and column chromatography (10-80% EtOAc/pet ether) gave a brown solid (3.01 g, 59%); 1H NMR (400 MHz, DMSO-d6) delta ppm 7.71 (d, J=9.6 Hz, 1 H), 7.48 (s, 1 H), 7.10 (d, br, J=7.3 Hz, 1H), 6.68 (d, J=10.1 Hz, 1H), 3.87-3.82 (m, 3H), 3.02-2.93 (m, 2H), 2.02-1.98 (m, 2H), 1.41 (s, 9H), 1.40-1.31 (m, 2H); m/z (ES+APCI)+: 396/398 [M+H]+.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 89794-02-5, 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. 89794-02-5 name is 4-Bromo-2-chlorotoluene, 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.

l-(3-Chloro-4-methylphenyl)-3-phenylpiperazine (compound of type 14, Figure 11): 2-phenyl- piperazine (0.13 g, 0.80 mmol), 2-Cl-4-Br-toluene (0.10 ml, 0.76 mmol), Pd2dba3 (0.07 g, 0.08 mmol), BINAP (0.048 g, 0.08 mmol) and OtBu (0.13 g, 1.14 mmol) were stirred in toluene (2 mL) at 80C. Aqueous work up, dichloromethane extraction and removal of volatiles was followed by flash chromatography separation using ethyl acetate gradient ( 10-60%) in hexanes to afford 0.13 g (56%) of l-(3–Chloro-4-methylphenyl)-3 -phenylpiperazine 14. 1H – NMR (CDC13, 400 MHz, delta ppm) 7.46-7.44 (m, 2H), 7.39-7.29 (m, 3H), 7.08 (d, / = 8.4 Hz, 1H), 6.91 (d, / = 2.8 Hz, 1H), 6.75 (dd, / = 8.8, 2.8 Hz, 1H), 3.96 (dd, / = 10.4, 2.8 Hz, 1H), 3.57-3.54 (m, 2H), 3.24 (dt, / = 11.6, 3.2 Hz, 1H), 2.86 (td, / = 11.6, 3.2 Hz, 1H), 2.68 (t, / = 11.2 Hz, 1H), 2.27 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-chlorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; SHIFA BIOMEDICAL CORPORATION; ABDEL-MEGUID, Sherin, Salaheldin; ABOU-GHARBIA, Magid; BLASS, Benjamin; CHILDERS, Wayne; ELSHOURBAGY, Nabil; GHIDU, Victor; MARTINEZ, Rogelio; MEYERS, Harold; MOUSA, Shaker, A.; WO2014/150395; (2014); A1;,
Chloride – Wikipedia,
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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2687-12-9, name is Cinnamyl 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 2687-12-9, Computed Properties of C9H9Cl

General procedure: A representative procedure of skeleton 4 is as follows: K2CO3 (400 mg, 2.9 mmol) was added to a solution of 3 (1.0 mmol) in acetone (10 mL) at rt. The reaction mixture was stirred at rt for 10 min. Cinnamyl chloride (1.05 mmol) was added to the reaction mixture at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled to rt, concentrated, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=6:1 to 1:1) afforded 4.

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

Reference:
Article; Chang, Meng-Yang; Lu, Yi-Ju; Cheng, Yu-Chieh; Tetrahedron; vol. 71; 8; (2015); p. 1192 – 1201;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics