Month: June 2021

Electric Literature of 2268-05-5, A common heterocyclic compound, 2268-05-5, name is 2,6-Dichlorofluorobenzene, molecular formula is C6H3Cl2F, 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.

EXAMPLE 20 2-[3-(2,6-Dichloro-phenoxy)4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-20) step 1-To a solution of 12a (0.200 g; 0.960 mmol) and NMP (4 mL) was added K2CO3 (0.398 g; 2.88 mmol) and 1,3-dichloro-2-fluoro-benzene (0.174 g; 1.056 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4) filtered and evaporated. The crude product was purified by SiO2 chromatography eluding with a hexane/EtOAc gradient (0 to 40% EtOAc) to afford 144. steps 2 and 3-Hydrolysis and formation of the acid chloride were carried as described in step 7and 8 of Example 1 and used without additional purification. step 4-The acid chloride from step 3 (0.14 mmol) was dissolved in acetone (2 mL) and the flask was purged with nitrogen. NaHCO3 (0.024 g; 0.28 mmol) was added followed by 4-amino-benzenesulfonamide (0.024 g; 0.14 mmol) and water (4 mL). The mixture was sonicated for 5 min and allowed to stir for 12 h at RT. The reaction mixture was filtered and the crude product was washed sequentially with water and diethyl ether to afford I-20. Compound I-23 was prepared in the same manner except 4-amino-benzenesulfonamide was replaced by 2-chloro-phenylamine.

The synthetic route of 2268-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239880; (2005); 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. 95-81-8, name is 2-Chloro-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8ClN

Preparation of (2-chloro-5-methyl-phenyl)urea (Intermediate 7) A solution of 2-chloro-5-methylaniline (10 g, 70.6 mmol) and potassium cyanate (14.3 g, 176 mmol) in a mixture of acetic acid (340 mL) and water (34 mL) was stirred at room temperature during 4 hours. The solvent was evaporated and the residue taken into a mixture of CH2Cl2 and an aqueous saturated solution of NaHCO3. The precipitate was filtered, washed with dichloromethane and dried under vacuum to give 12.6 g (97%) of intermediate 7. 1H NMR [(CD3)2SO] delta8.05 (s, 1H, NH), 7.96 (s, 1H), 7.23 (d, 1H), 6.75 (d, 1H), 6.37 (br s, 2H), 2.24 (s, 3H).

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 95-81-8.

Reference:
Patent; Bernardelli, Patrick; Ducrot, Pierre; Lorthiois, Edwige; Vergne, Fabrice; US2002/198198; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 62356-27-8, The chemical industry reduces the impact on the environment during synthesis 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

Take a 500 ml double-necked round bottom bottle and place it in a stirrer with a reflux tube. After drying, it is filled with nitrogen. First, add compound A-1 (20.548 g, 1.0 equivalent) and NBS (N-bromosuccinimide). , 19.5778 grams, 1.1 equivalents),And AIBN (azobisisobutyronitrile, 0.821 g, 0.5 mol%), followed by the addition of carbon tetrachloride (250 ml) and stirred for 10 minutes.Finally heated to reflux and reacted for 24 hours;After warming-up, water (200 ml) was added, followed by extraction with ethyl acetate (3×200 ml), and the obtained extract was sequentially dried over magnesium sulfate, filtered and evaporated to dryness. Ethyl acetate/hexane, 1/10) gave Intermediate 1-1 (21.044 g, yield 74%).

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-chloro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ningbo Lumilan New Materials Co., Ltd.; Ningbo Jizhichuang New Materials Institute Co., Ltd.; Wei Dingwei; Xie Kunshan; Chen Zhikuan; (50 pag.)CN109651423; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33050-38-3, The chemical industry reduces the impact on the environment during synthesis 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, I believe this compound will play a more active role in future production and life.

e) 3-Chloro-6-(cyclohexyloxy)[1,2,4]triazolo[4,3-b]pyridazine may be prepared in the following manner: 762 mg of sodium hydride at 60% in oil are added to a solution of 3.18 g of cyclohexanol in 30 cm3 of tetrahydrofuran, at 0 C. under argon. After stirring for 15 minutes, 3 g of 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine (commercial) are added. The brown suspension is stirred for 22 hours while allowing it to warm gradually to 20 C. The reaction mixture is poured into ice-water and the mixture is extracted with ethyl acetate. After concentrating the organic phase to dryness under vacuum, a brown oil is obtained. The oily residue is chromatographed on Biotage Quad 12/25 (KP-SIL, 60A; 32-63 muM), eluting with a 95/5 to 65/35 gradient of cyclohexane/ethyl acetate. 2.7 g of 3-Chloro-6-(cyclohexyloxy)[1,2,4]triazolo[4,3-b]pyridazine are thus obtained in the form of a yellowish powder, the characteristics of which are as follows:

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, 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; US2012/165326; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 6775-78-6, 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 6775-78-6 as follows.

To 6-chloro-imidazo[l,2-b]pyridazine (1 eq, 17 mmol, 2.4 g) in acetic acid (10 ml) under inert atmosphere, is added dropwise bromine (1 eq, 17 mmol, 0.82 ml). After 4 hours stirring at room temperature, the reaction mixture is filtered and dried under vacuum to give 3-bromo-6- chloro-imidazo[l,2-b]pyridazine 1H nmr (MeOD) 8.42 (IH, d, J = 9.81 Hz), 8.07 (IH, s) and 7.91 (IH, d, J = 9.48 Hz).

According to the analysis of related databases, 6775-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; WO2008/52734; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 363-51-9, 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. 363-51-9, name is 2-Chloro-6-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 0 C stirred solution of 5-fluoro-4-(3-oxo-5,6 -dihydro-3H-[1 ,2,4]triazolo[3,4-c][1 ,4]oxazin- 2(8H)-yl)-2-{[(2S)-1 ,1 ,1 -trifluoropropan-2-yl]oxy}benzoic acid (intermediate 24) (74.3 mg, 190 muiotaetaomicronIota) and DMF (3 drops) in anhydrous dichloromethane (0.95 ml) was added oxalyl chloride dropwise (28,9 mg, 0.23 mmol). The resulting mixture was warmed to room temperature, stirred for one hour and concentrated under reduced pressure. A solution of the crude acid chloride in dichloromethane (0.63 ml) was then added dropwise to a 0 C stirred solution of 2- chloro-6-fluoraniline (30.4 mg, 0.21 mmol) and triethylamine (21 .1 mg, 0.21 mmol) in dichloromethane (0.70 ml). Following complete addition, the mixture was warmed to room temperature and stirred for one hour. Aqueous hydrochloric acid (1 .0 M, 10 ml) was added to the residue and extracted with dichloromethane (3 x 10 ml). The combined organic extracts were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a pale yellow oil. The residue was purified by reverse phase column chromatography (acetonitrile, 0.1 % aqueous formic acid) to give the amide as a white solid (73.3 mg, 66 %).LC-MS (method A): Rt = 1 .18 min; MS (ESIpos): m/z = 519 [M+H]+1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1 .572 (8.35), 1 .659 (7.01 ), 1.676 (7.05), 3.807 (2.84), 3.820 (4.22), 3.834 (3.51 ), 4.086 (3.74), 4.098 (3.02), 4.100 (4.34), 4.1 13 (2.89), 4.772 (16.00), 4.91 1 (0.46), 4.927 (1 .09), 4.942 (1 .41 ), 4.958 (1 .09), 4.973 (0.42), 7.1 12 (0.89), 7.1 16 (0.94), 7.133 (1 .48), 7.136 (1 .96), 7.140 (1 .10), 7.155 (1.20), 7.159 (1 .25), 7.222 (0.85), 7.235 (0.84), 7.242 (1 .98), 7.256 (2.1 1 ), 7.263 (2.04), 7.285 (2.13), 7.290 (2.75), 7.305 (0.88), 7.309 (1 .07), 7.312 (0.89), 7.463 (2.95), 7.477 (2.96), 8.182 (3.04), 8.212 (3.06), 9.021 (2.04).

The synthetic route of 2-Chloro-6-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE GENERAL HOSPITAL CORPORATION; GRADL, Stefan, Nikolaus; NGUYEN, Duy; EIS, Knut; GUENTHER, Judith; STELLFELD, Timo; JANZER, Andreas; CHRISTIAN, Sven; MUELLER, Thomas; EL SHEIKH, Sherif; ZHOU, Han, Jie; ZHAO, Changjia; SYKES, David B; FERRARA, Steven, James; LIU, Kery; HERBERT, Simon, Anthony; MERZ, Claudia; NIEHUES, Michael; NISING, Carl, Friedrich; SCHAeFER, Martina; ZIMMERMANN, Katja; KNAEBLEIN, Joerg; THEDE, Kai; FAUPEL, Thomas; (539 pag.)WO2018/77944; (2018); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13726-14-2, These common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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.

3 was synthesized in a similar procedure as described for 2 by using 4-chloro-3-methoxyaniline (400 mg, 2.54 mmol), 1 (312 mg, 2.54 mmol), HOBt·H2O (389 mg, 2.54 mmol), DIPEA (0.66 g, 5.08 mmol), EDC.HCl (730 mg, 3.81 mmol) and anhydrous 1,4-dioxane (30 mL). 3 was obtained as a pale yellow solid (325 mg, 1.34 mmol, 53 % yield); mp: 120 C. 1H NMR (500MHz, CDCl3) delta ppm 10.07 (s, 1H), 8.63 (d, J=4.0Hz, 1H), 8.29 (d, J=8.0Hz, 1H), 7.92 (ddd, J=7.6, 7.6, 1.6Hz, 1H), 7.81 (d, J=2.0Hz, 1H), 7.50 (dd, J=7.0Hz, 5.0Hz, 1H), 7.34 (d, J=8.5Hz, 1H), 7.09 (dd, J=9, 2.5Hz, 1H), 3.97 (s, 3H). 13C NMR (125MHz, CDCl3) delta ppm 162.41, 155.68, 149.85, 148.37, 138.17, 137.97, 130.47, 127.01, 122.72, 117.80, 112.45, 104.37. LC-MS, calcd for C13H11N2O2Cl: 262.05; obsd: 263.0 [M+H]+.

Statistics shows that 4-Chloro-3-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 13726-14-2.

Reference:
Article; Kil, Kun-Eek; Zhang, Zhaoda; Jokivarsi, Kimmo; Gong, Chunyu; Choi, Ji-Kyung; Kura, Sreekanth; Brownell, Anna-Liisa; Bioorganic and Medicinal Chemistry; vol. 21; 19; (2013); p. 5955 – 5962;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 118-69-4, The chemical industry reduces the impact on the environment during synthesis 118-69-4, name is 2,6-Dichlorotoluene, I believe this compound will play a more active role in future production and life.

5 g of catalyst, as described in examples 3 and 4, was loaded in the reactor along with the diluent corundum particles (1: 1 by weight) and the reaction was performed under the following conditions. A reaction temperature of 350 to [400C] was used, and the GHSV comprised between 650-750 [H-1.] The contact time consisted of 4.8 to 5.5 seconds. The mole ratio of 2,6-DCT : H20 : NH3: air: N2 was 1: 15: 3-4: 21, the molar concentration of 2,6- DCT was 2.4 % and the ratio of [0/NH3] was 1. [1 %.] 5 g [VPCRO/TI02] (anatase) catalyst, as described in examples 3 and 4, was loaded in the reactor together with the diluent corundum particles (1: 1 by weight) and tested the influence of water vapour in the feed gas on the catalytic performance of the catalyst. The reaction was performed under the following reaction conditions. A reaction temperature of 350 to [400C] was used. The mole ratio of 2,6-DCT : NH3: air was 1: 4: 21, the molar concentration of 2,6-DCT was 2.1 to 3.8 %, and the ratio of [0/NHS] was 1. [1 %.]

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, 2,6-Dichlorotoluene, other downstream synthetic routes, hurry up and to see.

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

Adding a certain compound to certain chemical reactions, such as: 873-38-1, name is 2-Bromo-4-chloroaniline, 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 873-38-1, Computed Properties of C6H5BrClN

General procedure: Compound 15 (67.5 g, 0.355 mol) was added to the 300 mL 15 % aq. HCl. A resulting suspension was stirred for 1 h at 80 oC, then cooled to -5 C and NaNO2 (26.0 g, 0.365 mol) in H2O (50 mL) was slowly added. The mixture was stirred for 1.5 h at -5 C and then the excess of HNO2 was neutralized with urea. The solution of KI (57.2 g, 0.0355 mol) in 50 mL H2O was added dropwise at 0 oC (caution, the fast evolution of N2 was observed). The mixture was warmed to room temperature and stirred for 40 h. After this time CHCl3 was added, water phase was extracted with CHCl3 (3 × 100 mL), joined organic phases were washed with saturated solution of NaHCO3 (200 mL), 5% solution of Na2S2O3 (200mL) and5% solution of Na2S2O5 (200mL). Organic phase was dried over MgSO4 and concentrated under reduced pressure. The obtained crude product was distilled under reduced pressure (b.p. 90-91 oC, 2 Tr) affording 17 as viscous oil (69.1 g, 64%).

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

Reference:
Article; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-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. Formula: C6H5ClFN

Preparation 38 2-Chloro-4-fluoro-N-(4-fluorophenyl)aniline A round bottom flask was charged with 1-bromo-4-fluorobenzene (6.011 g, 34.4 mmol), 2-chloro-4-fluoroaniline (5.000 g, 34.3 mmol), Xantphos (0.795 g, 1.4 mmol), anhydrous toluene (200 mL), and sodium tert-butoxide (4.952 g, 51.5 mmol). The mixture was degassed and filled with nitrogen, and then tris(dibenzylideneacetone)dipalladium(0) (0.944 g, 1.0 mmol) was added and the reaction was stirred under nitrogen at 100 C. for 16 hrs. After cooling to room temperature, the mixture was filtered through Celite and the filter cake washed with methylene chloride. The filtrate was concentrated and the residue purified by silica gel chromatography (0-20% ethyl acetate/hexanes) to afford a yellowish oil (5.63 g, 68%). 1H NMR (300 MHz, CDCl3) delta 7.14 (dd, 1H, J=8.4, 3.0 Hz), 7.12-6.98 (m, 5H), 6.88 (td, 1H, J=8.7, 3.0 Hz), 5.80 (br s, 1H).

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

Reference:
Patent; Bersot, Ross; Humphries, Paul; US2013/303524; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics