Tag: M.W=100-200

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. 344-19-4, name is 2,6-Dichloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 344-19-4

A.9.1. Synthesis of 1 ,3-dichloro-5-fluoro-2-(prop-2-en-1 -yl)benzene a23. To a solution of allyl bromide (21 .6 mL, 249.9 mmol) in degassed ACN (80 mL) was added fert-butyl nitrite (3.99 mL, 33.22 mmol). A solution of 2,6-dichloro-4-fluoroaniline (3 g, 16.66 mmol) in ACN (5 mL) was added dropwise within 20 min. The reaction mixture was stirred at rt for 90 min. and concentrated under vacuum. The residue was taken up EtOAc and washed with water. The organic layer was dried over Na2S04, filtered and concentrated under vacuum. The residue was purified by column chromatography using 1 % EtOAc in hexanes as eluent to afford 1 .4 g of 1 ,3-dichloro-5-fluoro-2-(prop-2-en-1 -yl)benzene a23. Yield: 41 % LCMS: 205 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta 7.54 (d, J = 8.4 Hz, 2H), 5.91 -5.82 (m, 1 H), 5.07 (d, J = 9.9 Hz, 1 H), 4.91 (m, 1 H), 3.59 (d, J = 5.2 Hz, 2H).

The synthetic route of 344-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; VALADE, Anne; JNOFF, Eric; ATES, Ali; BURSSENS, Pierre; SKOLC, David; (211 pag.)WO2016/55479; (2016); 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. 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, This compound has unique chemical properties. The synthetic route is as follows., 7781-10-4

A portion of the compound obtained in Step 1 above (1.36 mmol) and lithium hydroxide monohydrate (571 mg, 13.62 mmol, 10 eq.) were treated at 110 C. in PDO-water (40 ml, 1:1). The v/v) mixture is stirred for 7-36 hours. The reaction mixture was neutralized with 1N aqueous HCl, and the resulting precipitate was filtered off, washed with water and dried.The preparation of R2b was achieved using general procedure 1 starting with the preparation of R1a and methyl iodide as the alkylating agent.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LTD; KOTSCHY, ANDRAS; WEBER, CSABA; VASAS, ATTILA; MOLNAR, BALAZS; KISS, ARPAD; MACIAS, ALBA; MURRAY, JAMES BROOKE; LEWKOWICZ, ELODIE; GENESTE, OLIVIER; CHANRION, MAIA; DEMARLES, DIDIER; IVANSCHITZ, LISA; (502 pag.)TW2018/2094; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, 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. 6940-78-9 name is 1-Bromo-4-chlorobutane, 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.

Example A4; a. Preparation of intermediate 19; A solution of l-bromo-4-chlorobutane (22.25 ml, 0.19 mol) in diethyl ether (100 ml) was added dropwise (under N2 atmosphere) to a suspension of activated Mg turnings (4.67 g, 0.19 mol) in diethyl ether (100 ml). Some crystals of iodine were also added. The temperature in the flask increased, and the orange colour turned to white. Once the addition of l-bromo-4-chlorobutane was completed, the reaction was cooled in an ice- bath and 2-naphthalenecarboxaldehyde (20.00 g, 0.13 mol) was added dropwise as a solution in THF (200 ml, dry). The reaction mixture was stirred in the ice-bath for 4 hours. Then the mixture was quenched with NH4Cl 1 N. Both phases were separated. The organic layer was washed with brine, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by flash chromatography (eluent: n- hexane/EtOAc 20:1). The desired fractions were collected and the solvent was evaporated, yielding intermediate 19.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-chlorobutane, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/68272; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

29671-92-9, 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. 29671-92-9, name is Carbamimidic chloride hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

A mixture consisting of S-amino-?-chloro-pyridine^-carbonitrile (4.6 g, 30 mmol), chloroformamidine hydrochloride (6.9 g , 60 mmol) and dimethylsulfon (12 g) was heated at 165 0C for 30 minutes. After cooling to room temperature, water (500 ml) was added. The solution was neutralized with a 30 % NaOH solution to pH 9-10. The precipitate was filtered off, washed with water, dried over P2O5, resulting in the pure title compound as a yellow solid (4.0 g, yield: 68 %) which was characterised as follows:- Rf = 0.40 (MeOH/CH2CI2 1 :9); and – MS (m/z): 196, 198 ([M+H]+, 100).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; 4 AZA Bioscience nv; WO2006/135993; (2006); A1;,
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 6940-78-9 as follows. 6940-78-9

Methanol (149 L), 7-hydroxy-1H-quinolin-2-one (14.87kg), and potassium hydroxide (6.21 kg) were mixed and stirred.After dissolution, 1-bromo-4-chlorobutane (47.46 kg) was further added thereto and the resulting mixture was stirred under reflux for seven hours. Thereafter, the mixture was stirred at 10C forone hour. The precipitated crystal was centrifuged and washed with methanol (15 L). The wet crystal was collected and placed ina tank. Water (149 L) was added thereto, followed by stirring atroom temperature. After centrifugation, the resulting solid was washed with water (30 L). The wet crystal was collected andplaced in a tank. After adding methanol (74 L), the mixture was stirred under reflux for one hour, cooled to 10C, and thenstirred. The precipitated crystal was centrifuged and washed withmethanol (15 L). The separated crystal was dried at 60C to obtain 7-(4-chlorobutoxy)-1H-quinolin-2-one (15.07 kg).

According to the analysis of related databases, 6940-78-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; YAMASHITA, Hiroshi; SATO, Tetsuya; MINOWA, Takuya; HOSHIKA, Yusuke; TOYOFUKU, Hidekazu; YAMAGUCHI, Tatsuya; SOTA, Masahiro; KAWANO, Shuuji; NAKAMURA, Takayuki; ETO, Ryohei; IKEBUCHI, Takuma; MORIYAMA, Kei; ITO, Nobuaki; WO2013/162046; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, These common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, 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.

A mixture of 10(a) (prepared similarly to Example 9A, step 1, using appropriate starting material, 460 mg, 1.00 mmol), diboron pinacol ester (305 mg, 1.20 mmol), potassium acetate (294 mg, 3.00 mmol), 1,1′-bis(diphenylphosphino)ferrocene (55 mg, 0.10 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (82 mg, 0.10 mmol) in 1,4-dioxane (5 mL) was heated in a closed pressure tube under N2 at 80 C for 2 h. The mixture was cooled to room temperature. To this mixture was added 1-bromo-3-chloro-benzene (235 muL, 2.00 mmol), K3PO4 (636 mg, 3.00 mmol), dichloro-[1,1′-bis(diphenylphosphino)ferrocene]-palladium (II) dichloromethane adduct (41 mg, 0.050 mmol), and 1,4-dioxane (5 mL). The mixture was heated in a closed pressure tube under nitrogen at 80 C for 16 h. The mixture was partitioned between NH4Cl (saturated) and EtOAc. The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography of the residue on a silica gel column with EtOAc:hexane (20:80, then 25:75) as eluent gave (+)-Example 10 (360 mg, 85%) as off-white solids. HCl salt: off-white solids; MS (FAB) m/z 422 (MH+, 100).

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 108-37-2.

Reference:
Patent; SCHERING CORPORATION; EP1036072; (2004); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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.

To 400ml of 1-butyl-2,3-dimethylimidazole hexafluorophosphate was added 650g 20%Aqueous solution of sodium methyl mercaptan, heated to a reduced pressure and distilled to 100C/0.08MPa, keeping no distillate flowing out, then suspending heating, adding 200g of 2,6-dichlorotoluene to the system, maintaining at 100C for 3 hours, then cooling to 35 , 30g of methyl chloride gas was introduced into the kettle, kept for 1 hour, and atmospheric distillation was started. After 55 and no distillate flowed out, it was changed to another receiving bottle and vacuum distillation was started. It stopped after 180/0.09MPa heating,A total of 205 g of distillate was received, which was 2-methylthio-6-chlorotoluene with a yield of 97.3%; after the vacuum distillation was completed, the remaining ionic liquid solution was filtered to remove inorganic salts for recovery

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichlorotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shenyang Kechuang Chemicals Co., Ltd.; Lin Yang; Yang Zhaoguo; Li Ziliang; Ming Xu; Li Tao; Zhang Chuanyang; Hu Jinying; (7 pag.)CN111233721; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

To 3,5-dichlorobenzylamine (0.49 g, 2.8 mmol) in DCM (5 ml.) was added the alpha,beta- unsaturated ketone 24 (2.12 mmol) in DCM (10 ml_). After stirring at room temperature for 15 mins, Fmoc-diaminobutyric acid(Boc)-OH (1.35 g, 3.1 mmol) and DIC (0.5 ml_, 3.2 mmol) was added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum spirit:EtOAc (1 :1 to 0:1 ), providing compound 25 (0.48 g, 22%).

Statistics shows that 39989-43-0 is playing an increasingly important role. we look forward to future research findings about 3,5-Dichlorobenzylamine.

Reference:
Patent; MIMETICA PTY LTD; BLASKOVICH, Mark, Arnold, Thomas; CASSIDY, Peter, Joseph; WO2010/96854; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 626-43-7, name is 3,5-Dichloroaniline, 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. 626-43-7

General procedure: To a solution of alcohol (1.1 mmol) in a mixture of solvents EtOAc: DMSO (4 ml: 2 ml), was added T3P (2.5 mmol, 50% solution in ethyl acetate) at 0 C, and the resulting mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. The reaction was monitored by TLC, amine (1.0 mmol) and thioglycolic acid (1.0 mmol) were added once and stirred further for 1-3 h at room temperature. After completion of the reaction, the mixture was diluted with water (20 ml) and neutralized by adding 10% NaHCO3 solution. The product was extracted with ethyl acetate (10 ml 2) and the combined organic layers were washed with water followed by brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford a crude product which was purified by column chromatography using hexane: ethyl acetate mixture (8:2) as an eluent.

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, 626-43-7, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sharath Kumar, Kothanahally S.; Swaroop, Toreshettahally R.; Harsha, Kachigere B.; Narasimhamurthy, Kereyagalahally H.; Rangappa, Kanchugarakoppal S.; Tetrahedron Letters; vol. 53; 42; (2012); p. 5619 – 5623;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

72235-56-4, These common heterocyclic compound, 72235-56-4, name is 3-Chloro-4-fluorobenzylamine, 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.

Preparation of 3-[(3-chloro-4-fluorobenzyl)amino]-1-propanesulfonic acid To a solution of 3-chloro-4-fluorobenzy]amine (1.0 g, 7.8 mmol) in Acetone (2 mL) and Toluene (2 mL) was added 1,3-propane sultone solution (1.5 M in THF, 4.0 mL, 6.0 mmol). The solution was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration and washed with acetone (2*5 mL) and dried in a vacuum oven at 50 C., affording the title compound, 0.041 g (2%). 1H NMR (D2O, 300 MHz) delta ppm 7.44 (dd, 1H, J=2.2 Hz, 6.9 Hz), 7.25 (m, 1H), 7.15 (t, 2H, J=8.6 Hz), 4.07 (s, 2H), 3.07 (t, 2H, J=7.8 Hz), 2.83 (t, 2H, J=7.5 Hz), 1.98 (m, 2H). 13C (D2O, 75 MHz) delta ppm 160.07, 156.77, 132.18, 130.43, 130.22, 127.90, 120.94, 117.58, 117.29, 50.20, 48.17, 46.09, 21.67. 19F (D2O, 282 MHz) delta ppm -115.33. ES-MS 280 (M-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 72235-56-4.

Reference:
Patent; Kong, Xianqi; Wu, Xinfu; Bouzide, Abderrahim; Valade, Isabelle; Migneault, David; Bellini, Francesco; US2006/183800; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics