Month: September 2021

Application of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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.

General procedure: The syntheses of the ferrocenyl phenylguanidines were achieved in four steps (Scheme-1 suppl). In the first step; nitrophenylferrocene (a and b) were made by the coupling of ferrocene with diazonium salts of nitroaniline using phase transfer catalyst [20]. In the second step; these nitro phenyl ferrocene were reduced into ferrocenylaniline (c and d) using palladium on charcoal and hydrazine as reducing agent [21]. In the third step three different chloro-substituted thioureas (e) were synthesized by the coupling of substituted aniline with thiocynates in acetone [22]. In the fourth step; the benzoylphenylthiourea (e) were mixed with the ferrocenyl aniline (c and d) in dimethyl formamide (DMF) in equimolar ratio with two equivalents of triethylamine (Et3N). The temperature was maintained below 5C using an ice bath and one equivalent of mercuric chloride (HgCl2) was added to the reaction mixture with vigorous stirring. The ice bath was removed after 30min while the stirring continued overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) till the completion of reaction. Chloroform (CHCl3, 20ml) was added to the reaction mixture and the suspension was filtered through a sintered glass funnel to remove the mercuric sulfide (HgS) residue. The solvents from filtrate were evaporated under reduced pressure and residue was re-dissolved in dichloromethane (CH2Cl2, 20ml), washed with water (4×30ml) and dried the organic phase over anhydrous magnesium sulfate (MgSO4). The solvent was evaporated and residue was purified by column chromatography to afford ferrocenyl phenylguanidines (f and g) [23]. Solid and liquid state characterization data is given in Supplemental part

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloroaniline, its application will become more common.

Reference:
Article; Gul, Rukhsana; Badshah, Amin; Khan, Azim; Junaid, Asif; Rauf, Muhammad Khawar; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 264 – 269;,
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Related Products of 870-24-6, 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. 870-24-6, name is 2-Chloroethanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

13.5 g of 2-chloroethylamine hydrochloride was added to 8.7 g of mercaptoethanol solution under stirring, adjusted to pH=4.8, and reacted at 55 C. for 4 hours to produce 13.2 g.beta-2-aminoethylmercaptoethan-1-ol. Cooling to 0C,Slowly add 59g (40%) of tidal acetaminophenone chloride, adjust pH=3.8, control temperature at 0-2C for 4 hours, separate,Washing afforded 30.7 g of p-acetamidobenzenesulfonamide ethyl-2-hydroxyethyl sulfide

The chemical industry reduces the impact on the environment during synthesis 2-Chloroethanamine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Taixing Jinyun Dyeing Liao Co., Ltd.; Zhao Weiguo; Su Jinqi; Ju Suhua; Wang Guomin; Zhang Weiping; (27 pag.)CN104592786; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 38762-41-3 as follows. Recommanded Product: 4-Bromo-2-chloroaniline

Preparation 94: 2-Chloro-4-(oxazol-5-yl)aniline; [00264] Palladium acetate (5.4mg, 0.024mmol) was added to a solution of 4-bromo-2- chloroaniline (0.1 g, 0.484mmol), oxazole (0.064mL, 0.969mmol), di(1 -adamantyl)-/> butylphosphine (0.017g, 0.048mmol), pivalic acid (0.020g, 0.194mmol) and potassium carbonate (0.201 g, 1 .453mmol) in DMA (2.4ml_). The reaction mixture was heated at 1 10 C overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35mg, 37%). 1 H NMR (500 MHz, CDCI3): delta 4.25 (br s, 2H), 6.82 (d, J = 8.3Hz, 1 H), 7.20 (s, 1 H), 7.38 (dd, J = 8.3, 2.0Hz, 1 H), 7.58 (d, J = 2.0Hz, 1 H), 7.87 (s, 1 H).LC (Method B)-MS (ESI, m/z) fR 2.47 min, 195 [(M+H+), 100%].

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Computed Properties of C7H7ClFN

A mixture of Example 235G (40.0 mg, 0.112 mmol), HATU (1- [bis(dimethylamino)methylene]-lH-l ,2,3-triazolo[4,5-]pyridinium 3-oxid (1666) hexafluorophosphate) (51.0 mg, 0.134 mmol), (4-chloro-3-fluorophenyl)methanamine (0.015 mL, 0.123 mmol), and triethylamine (0.031 mL, 0.224 mmol) in N,N-dimethylformamide (DMF) (1.5 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over MgSO/t, filtered, and concentrated. The residue was purified by HPLC performed on a Phenomenex Luna C18 column (250 x 30 mm, 10 mupiiota particle size) using a gradient of 20% to 100% acetonitrile:0.1 % aqueous trifluoroacetic acid over 26 minutes at a flow rate of 50 mL/minute to provide the title compound (49.6 mg, yield 89%). JH NMR (501 MHz, DMSO- ) delta ppm 8.29 (t, J = 6.3 Hz, 1H), 7.75 (s, 1H), 7.50 (dt, J = 15.1 , 8.5 Hz, 2H), 7.20 (dd, J = 10.4, 2.0 Hz, 1H), 7.11 – 6.99 (m, 2H), 6.82 (ddd, J = 9.0, 2.9, 1.1 Hz, 1H), 4.48 (s, 2H), 4.23 (d, J = 6.3 Hz, 2H), 4.03 (s, 2H), 2.13 – 1.95 (m, 4H), 1.95 – 1.77 (m, 4H); MS (ESI+) m/z 449.3 (M+H)+.

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, (4-Chloro-3-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

Step 1: methyl 14-cyclohex^l-7-meiksiotalene-7.&-dihydro-6H-indolol.2-e]fl.5]benzoxazocine-ll- carboxylate; To a solution of methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-lH-indole-6-carboxylate (prepared as described in example 9, step 1) in dry DMF (0.06 M) was added NaH (2.5 eq., 60% suspension in mineral oil). After 30 min, 3-chloro-2-(chloromethyl)prop-l-ene (1.2 eq.) was added dropwise via syringe and EPO the solution stirred at RT for 60 min. The reaction mixture was diluted with EtOAc and washed with IN aqueous HCl and with brine, dried (Na2SO4) and evaporated. The crude residue was purified by flash chromatography (10:1 PE/EtOAc), affording the pure methyl 14-cyclohexyl-7-methylene-7,8-dihydro- 6H-indolo[l,2-e][l,5]benzoxazocine-l l-carboxylate (70%) as light yellow foam; MS (ES+) m/z 402 (M+H)+.

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 1871-57-4.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); A2;,
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. 623-12-1, name is 1-Chloro-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7ClO

General procedure: A 25 mL synthesizer tube was taken with a mixture of aryl halide (0.5 mmol), aryl boronic acid (0.55 mmol),base (1.5 mmol), Pd-complex C1 (0.2 mol %) and the mixture was stirred in2 mL of water at 50C for the required time. After completion, the reaction mixture was extracted with ether (3 Chi 20 mL). The combined extract was washed with brine (2 Chi 20 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel,ethyl acetate-hexane: 1:9) to obtain the desired products. The products were confirmed by comparing the 1H and 13C NMR and mass spectral data with authentic samples.

According to the analysis of related databases, 623-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dewan, Anindita; Bora, Utpal; Borah, Geetika; Tetrahedron Letters; vol. 55; 10; (2014); p. 1689 – 1692;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13726-14-2, A common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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.

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.

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

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

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. 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-N-methylethanamine hydrochloride

Water (0.5 mL), intermediate 17 (0.17 g; 0.51 mmol) followed by tetrabutylammonium bromide (41 mg; 0.13 mmol) were added at room temperature to a mixture of potassium hydroxide (0.50 g; 7.63 mmol) in 2-methyltetrahydrofuran (5 mL). The reaction mixture was stirred for 10 minutes at room temperature, then stirred at 50C for 1 hour and (2- chloroethyl)-methylamine hydrochloride (CAS 4535-90-4) (0.119 g; 0.92 mmol) was added. The reaction mixture was stirred for 24 hours at 50C. The reaction mixture was cooled down to room temperature, poured into water and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (Spherical SiOH, 10muiotaeta, 60g; mobile phase: gradient from 0.5% NH4OH, 97% DCM, 3% MeOH to 0.5% NH OH, 95% DCM, 5% MeOH). The pure fractions were collected and evaporated to give 30 mg (15%) which was taken up Et20 and evaporated to give 29 mg (14%) of compound 44 , MP.: 80C (gum, Kofler).

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; ASTEX THERAPEUTICS LIMITED; BERDINI, Valerio; SAXTY, Gordon; ANGIBAUD, Patrick Rene; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; ROUX, Bruno; MEERPOEL, Lieven; WO2013/61080; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

432-21-3, 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 432-21-3 as follows.

1-Chloro-3-iodo-2-trifluoromethyl-benzeneTo a suspension of 3-Chloro-2-trifluoromethyl-phenylamine hydrochloride (30.9 g, iQ 0.16 mol) in H2O (90 mL) was added cone. HCI (65 mL) portion wise allowing the reaction to heat up to -45 0C. The temperature was maintained for 30 min then cooled in an ice bath < 5 0C. CH2CI2 (10 mL) was added and -10 min later a solution of sodium nitrite (13.6 g, 0.197 mol) in H2O (25 mL) was added dropwise. After a further 30 min, a solution of NaI (28.2 g, 0.188 mol) in H2O (50 mL) was again added dropwise keeping the temperature < 5 0C j 5 throughout both additions. After -1 h the reaction was diluted with CH2CI2 (200 mL) and sodium metabisulfite was added until the I2 color had been discharged. The layers were separated and the organic washed with brine, dried and the solvent evaporated to give 1- Chloro-3-iodo-2-trifluoromethyl-benzene (38.3 g, 79%) as an orange solid, which was used without further purification. MS: APCI: M+: 306.0 (305.9) At the same time, in my other blogs, there are other synthetic methods of this type of compound, 432-21-3, and friends who are interested can also refer to it. Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, molecular formula is C7H7ClFN, 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. COA of Formula: C7H7ClFN

Example 82; /V-[(2-chloro-4-fluorophenyl)methyl]-2-[3,5-dimethyl-1-(2-phenylethyl)- 1H-pyrazol-4-yl]acetamide (E82)[3,5-dimethyl-1-(2-phenylethyl)-1 H-pyrazol-4-yl]acetic acid (0.63 mmol) was dissolved in dimethylformamide (2 ml) and to this was added O-(7-Azabenzotriazol- 1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU, 0.63 mmol) and diisopropylethylamine (DIPEA, 1.26 mmol). The mixture was left to stand at room temperature for 15-20 minutes and then [(2-chloro-4-fluorophenyl)methyl]amine (0.63 mmol) in dimethylformamide (1 ml) was added. The mixture was left to stand overnight at room temperature and then the solvents were evaporated in-vacuo. The residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The mixture was then filtered through a phase separator and the organic phase was evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give the title compound as product after lyophilisation of the combined product fractions. LC/MS [M+H]+ = 399, retention time = 3.16 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15205-11-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/138876; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics