Tag: M.W=100-200

1871-57-4, A common compound: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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.

[0102] A tubular reactor was configured 300 with a static mixer 305, a T-mixer 310 and an elevated temperature stage 322 as illustrated schematically in FIG. 8. An organic stream 328 containing 3-chloro-2-(chloromethyl)prop-1-ene (1 equiv.), CHBr3 (5 equiv.), 18-crown-6 (5 mol %), pinacol (8.5 mol %), and methylene chloride (4 vol.) was mixed with an aqueous33% NaOH stream 329 at about 70C using mixers 305, 310 in the tubular reactor 300 to form1,1 -dibromo-2,2-bis(chloromethyl)cyclopropane 330. Flow rates were controlled by using the back pressure regulator 370 and by using the syringe pumps 335, 340 to deliver the organic and aqueous streams. The mixers 335, 340 were located in the elevated temperature stage 322 as illustrated in FIG. 8 and included a T-junction (T-mixer) 310 and a 29 element in-line static mixer 305 having a diameter about the same as that of the reactor tubing. The static mixer 305 includes counterhelices to achieve mixing of the biphasic stream in laminar flow. The residence time in the elevated temperatures stage 322 was about one hour. The yield of 1,1 – dibromo-2,2-bis(chloromethyl)cyclopropane 330 was – 9%.

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-Chloro-2-chloromethyl-1-propene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZENO ROYALTIES & MILESTONES, LLC; PINCHMAN, Joseph, Robert; BUNKER, Kevin, Duane; BIO, Matthew, M.; BREEN, Christopher; CLAUSEN, Andrew, M.; FANG, Yuanqing; LI, Hui; SHEERAN, Jillian, W.; (61 pag.)WO2019/51038; (2019); A1;,
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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. 344-19-4 name is 2,6-Dichloro-4-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. 344-19-4

To a solution of 6.07 g (19.1 mmol) of ethyl 2-[(2,6-dichloropyridin-3-yl)carbonyl]-3-ethoxyacrylate (CAS 157373-27-8) and 4.81 g (26.7 mmol) of 2,6-dichloro-4-fluoroaniline in 30 ml DCM were added 23.3 ml (134 mmol) of DIPEA, and the mixture was stirred at RT for 4 h. Subsequently, 2.64 g (19.1 mmol) of potassium carbonate were added and the mixture was heated under reflux overnight. The mixture was diluted with 200 ml of DCM and washed twice with 75 ml of 1 M aqueous hydrochloric acid. The organic phase was dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The suspension obtained was stirred with 40 ml of tert-butyl methyl ether, and the precipitate was filtered off with suction, washed with 10 ml of tert-butyl methyl ether and dried under high vacuum. 3.81 g (45% of theory, 94% purity) of the title compound were obtained. LC-MS (Method 1): Rt=1.04 min; MS (ESIpos) m/z 415 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=8.88 (s, 1H), 8.65 (d, 1H), 7.92 (d, 2H), 7.69 (d, 1H), 4.25 (q, 2H), 1.28 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; STRAUB, Alexander; BRECHMANN, Markus; MUeLLER, Thomas; MEININGHAUS, Mark; NOWAK-REPPEL, Katrin; TINEL, Hanna; MUeNTER, Klaus; FLIEGNER, Daniela; MONDRITZKI, Thomas; BOULTADAKIS ARAPINIS, Melissa; MARQUARDT, Tobias; VAKALOPOULOS, Alexandros; REBSTOCK, Anne-Sophie; WITTWER, Matthias Beat; (342 pag.)US2018/297994; (2018); A1;,
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112-26-5, 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. 112-26-5 name is 1,2-Bis(2-chloroethoxy)ethane, 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 suspension of4.5 g (14 mmol) of 2-diphenylphosphorylmethylphenol[12] and 0.56 g (14 mmol) of finely divided NaOHin 35 mL of dry dioxane was stirred for 0.5 h at 95C,next 1.3 g (7 mmol) of 1,8-dichloro-3,6-dioxaoctanewas added, the mixture was refluxed for 8 h, concentratedunder reduced pressure, 50 mL of water wasadded to the residue, the mixture was acidified withconcentrated HCl to pH 1 and extracted with CHCl3(3 ¡Á 25 mL). The extract was washed with diluted (1 : 2)HCl (2 ¡Á 30 mL), water (2 ¡Á 30 mL), and concentratedunder reduced pressure. The residue was dissolvedin 40 mL of anhydrous acetonitrile, 2.25 g (15 mmol) ofdry NaI was added, the mixture was refluxed for 1 h,cooled to 8C, the precipitate was separated by filtration,washed with boiling acetonitrile (10 mL) anddried in a vacuum. The precipitate was identified as a1 : 1 complex of L with NaI. Yield 4.3 g, 77%. ForC44H44INaO6P2 anal. calcd. (%): C, 60.01; H, 5.04; P,7.03. Found (%): C, 59.81, 59.73; H, 4.52, 4.90;P, 6.63, 6.91.

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:
Article; Bezhin; Dovhyi; Lyapunov, A. Yu.; Baulin; Baulin; Tsivadze, A. Yu.; Russian Journal of Inorganic Chemistry; vol. 64; 9; (2019); p. 1178 – 1185; Zh. Neorg. Khim.; vol. 64; 9; (2019); p. 997 – 1005,9;,
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10061-02-6,Some common heterocyclic compound, 10061-02-6, name is trans-1,3-Dichloropropene, molecular formula is C3H4Cl2, 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: A mixture of 0.01 mol (1.0 g) of pentane-2,4-dione, 0.001 mol (0.1 g) of sodium butylate, and 60 mL of anhydrous acetonitrile was irradiated at constant stirring for 20 min. The mixture was then cooled to room temperature and was charged with 0.015 mol of the corresponding alkene 4. Next, irradiation was continued for 2 h to complete conversion of pentane-2,4-dione. Upon completion of the reaction (GLC monitoring) the mixture was cooled to room temperature, washed with water, and extracted with chloroform. The organiclayer was dried with potassium carbonate and evaporated. The residue was distilled in a vacuum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10061-02-6, its application will become more common.

Reference:
Letter; Borisova, Yu. G.; Raskildina; Zlotskii; Russian Journal of General Chemistry; vol. 86; 9; (2016); p. 2126 – 2128; Zh. Obshch. Khim.; vol. 86; 9; (2016); p. 1564 – 1566,3;,
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Adding some certain compound to certain chemical reactions, such as: 626-43-7, name is 3,5-Dichloroaniline, 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 626-43-7. 626-43-7

General procedure: PdTBAB (1 mol % Pd in 250 mg of TBAB synthetized in scCO2), alcohol (2 mmol, 2 eq), amine (1 mmol, 1 eq) and anisole (1 mL) were introduced into a sealed tube under argon. The reaction was then heated at 140 C for 12 h. After cooling the reaction at room temperature, the mixture was filtrated on Celite and washed with Et2O and the filtrate was concentrated under vacuum. The crude oil was purified by column chromatography.

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 3,5-Dichloroaniline.

Reference:
Article; Cacciuttolo, Bastien; Pascu, Oana; Aymonier, Cyril; Pucheault, Mathieu; Molecules; vol. 21; 8; (2016);,
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98446-49-2, 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. 98446-49-2, name is 2,4-Dichloro-5-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 4 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide 2,4-Dichloro-5-methoxyaniline (5.00 g, 26 mmol) and cyanoacetic acid (2.28 g, 26.8 mmol) were mixed in 50 mL of tetrahydrofuran until a solution formed. This solution was heated to reflux and 1,3-diisopropylcarbodiimide (4.2 mL, 26.8 mmol) was added dropwise. After 30 minutes the mixture was cooled to ~15 C. in an ice-bath. The solid was collected by filtration and washed with tetrahydrofuran. The filtrate was slowly poured into water and stirred for 30 minutes. The white solid was collected by filtration, washed with water, and was then dissolved in 500 mL of ethyl acetate. The solution was dried over sodium sulfate and concentrated in vacuo to give 5.9 g (88%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide as a white solid, mp 180-181 C.; 1H NMR (400 MHz, DMSO-d6) delta 3.84 (s, 3H), 4.02 (s, 2H), 7.58 (s, 1 H), 7.66 (s, 1 H), 10.00 (s, 1 H); MS (ES) m/z257.0, 259.0 (M-H)- Analysis for C10H8Cl2N2O2; Calcd: C, 46.36; H, 3.11; N, 10.81. Found: C, 46.25; H, 3.10; N, 10.85.

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; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

622-24-2, Name is (2-Chloroethyl)benzene, 622-24-2, 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.

methyl 5-(phenethylamino)-2-(phenylsulfonamido)benzoate (13) To a round-bottom-flask under nitrogen methyl 5-amino-2-(phenylsulfonamido)benzoate 12 (184 mg, 0.6 mmol, 1.0 equiv.) and dry DMF (20 mL) were added. This was followed by addition of K2CO3 (691 mg, 3 mmol, 5.0 equiv.) and 1 -(2-chloroethyl)benzene (0.199 mL, 211 mg, 1.5 mmol, 2.5 equiv.) and the mixture was heated at 120 C for 16 hours. The reaction mixture was then allowed to cool down to room temperature and diluted with ice H20 (20 mL). The resulting mixture was extracted with Et^O (2 x 30 mL). All the organic extracts were combined, dried over NaS04 and concentrated. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=50:50) on silica gel to afford 13 (211 mg, 85%) as yellow oil. lH NMR (400 MHz, CDC13) delta 7.62-7.12 (m, 11H), 6.71-6.64 (m, 2H), 3.92-3.69 (m, 6H), 3.03-2.85 (m, 2H); 1 C NMR (100 MHz, CDC13) delta 166.57, 146.52, 139.75, 138.58, 133.08, 132.16, 131.83, 128.78, 128.64, 128.41, 127.73, 127.38, 126.31, 117.75, 117.00, 53.61, 52.04, 35.58.

Statistics shows that (2-Chloroethyl)benzene is playing an increasingly important role. we look forward to future research findings about 622-24-2.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
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Chlorides – an overview | ScienceDirect Topics

112-26-5, A common compound: 112-26-5, name is 1,2-Bis(2-chloroethoxy)ethane, 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.

A mixture of 1,2-bis(2-chloroethoxy)ethane (5.00 g, 26.73 mmol, 1.00 Eq) and NaI (12.02 g, 80.19 mmol, 3.00 Eq) in acetone (50 mL) was stirred at 56 C. for 72 hr under N2 atmosphere. Most solid sodium chloride was formed. After filtration of the resulting sodium chloride, the solution was concentrated in vacuum. The residue was diluted with CH2Cl2 (200 mL) and the solution was washed with water (100 mL), dried over Na2SO4 and evaporated in vacuum. The residue was purified by chromatography on silica gel (eluting with PE_EA=100:1 to 10:1) to afford the pure product 1,2-bis(2-iodoethoxy)ethane (9.10 g, 24.60 mmol, 92.02% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 3.80 (t, J=6.90 Hz, 4H), 3.70 (s, 4H), 3.29 (t, J=6.78 Hz, 4H).

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, 1,2-Bis(2-chloroethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novira Therapeutics, Inc.; Hartman, George D.; Kuduk, Scott; (85 pag.)US2016/272599; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13078-79-0, The chemical industry reduces the impact on the environment during synthesis 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, I believe this compound will play a more active role in future production and life.

General procedure: A solution of 24 (1.0 equiv.), HOBt (1.1 equiv.) and EDC (1.5 equiv.) in DMF (1.3 mmol/mL) was stirred at rt for 15 minutes. The appropriate amine (2.0 equiv.) was added and the resulting solution was stirred at rt for 5 hours. Reaction media was diluted with water and aqueous phase was extracted 3 times with EtOAc. Combined organic layers were washed successively with a solution of HCl 1N, a saturated solution of NaHCO3 and brine, dried over Na2SO4 and concentrated. The resulting solid was then purified by column chromatography on silica gel using the appropriate heptanes:EtOAc mixture.

The chemical industry reduces the impact on the environment during synthesis 2-(3-Chlorophenyl)ethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bollenbach, Maud; Lugnier, Claire; Kremer, Melanie; Salvat, Eric; Megat, Salim; Bihel, Frederic; Bourguignon, Jean-Jacques; Barrot, Michel; Schmitt, Martine; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 269 – 290;,
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94-97-3, Adding some certain compound to certain chemical reactions, such as: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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 94-97-3.

General procedure: A mixture of azole (0.2 mmol), ketone (0.3 mmol, 1.5equiv.), NaHCO3 (33.6 mg, 2.0 equiv.), I2 (101.6 mg, 2.0 equiv.), and 1,2-dichloroethane (2 mL) was stirred at 80 C for 24 h. After cooling to room temperature, the reaction mixture was quenched with a saturated solution of Na2S2O3 (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic phases were washed with brine (10 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatograph, using a mixture of petroleum ether and ethyl acetate (5:1-2:1) as eluent to afford the corresponding products. The identity and purity of the products was confirmed by 1H and 13C NMR spectroscopic analysis.

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 94-97-3.

Reference:
Article; Chen, Wenlin; Yan, Rulong; Tang, Dong; Guo, Shuaibo; Meng, Xu; Chen, Baohua; Tetrahedron; vol. 68; 38; (2012); p. 7956 – 7959;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics