Tag: M.W=100-200

Electric Literature of 4152-90-3, These common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, 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: Compounds 5a?7a, 9a?11a, and 13a were synthetized using a microwave reactor with a focusedfield. Corresponding N-benzyl-3-chloropyrazine-2-carboxamide (0.6 mmol) was dissolved in methanol(3 mL) and appropriate benzylamine (1.8 mmol, 3 equiv.), along with pyridine (40 mg, 0.6 mmol,1 equiv.) as a base, were added. Our previous observations revealed that triethylamine (TEA) as a basecannot be used for microwave reactions. During the procedure, TEA is partially decomposed (probablyto diethylamine and similar species, which may act as undesired nucleophiles in the dehalogenationreaction). The use of pyridine as the base combined with benzylamines was experimentally verifiedin previous projects [18]. Conditions for synthesis were 150°C, 30 min, and 100 W. The progressof the reactions was monitored by TLC in system hexane/ethyl acetate 1:1. The reaction mixturewas adsorbed on silica by removing the solvents in vacuo and the product was purified by flashchromatography using gradient elution with ethyl acetate (0?100percent) in hexane. Products 7a and 10awere recrystallized from EtOH/H2O.

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Semelkova, Lucia; Jand’ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Franti?ek; Kubi?ek, Vladimir; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; McPhee, Derek J.; Molecules; vol. 22; 3; (2017);,
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Adding a certain compound to certain chemical reactions, such as: 2106-02-7, name is 2-Chloro-4-fluoroaniline, 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 2106-02-7, Product Details of 2106-02-7

[000213] To a stirred solution of crude acid chloride (70 mg, crude) in CH2C12 (5 mL) under argon atmosphere were added 2-chloro-4-fluoroaniline 184 (25 mg, 0.17 mmol) and pyridine (0.07 mL, 0.86 mmol) at 0 C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with CH2C12 (2 x 30 mL). The combined organic extracts were washed with 1 N HC1 (20 mL), 10% NaHCO3 solution (30 mL), brine (15 mL) dried over sodium sulfate, filtered and concentrated in vacuo to obtain crude. The precipitated material was either directly dried in vacuo or triturated or purified through silica gel column chromatography /preparative HPLC or by acid-base treatment to afford the desired compound.

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

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
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Reference of 886762-39-6, The chemical industry reduces the impact on the environment during synthesis 886762-39-6, name is 3,4-Dichloro-2-fluoroaniline, I believe this compound will play a more active role in future production and life.

j00324j A solution of 3,4-dichloro-2-fluoroaniline (5.0 g, 31 mmol) and potassium 0-ethyl carbonodithioate (11 g, 67 mmol) in 1V N-dimethylformamide (50 mL) was stirred at 130 C for 16 hours. On completion, the reaction was cooled to room temperature, and hydrochloric acid (1M, 75 mL) was added. The mixture was stirred for 0.5 hour, resulting in formation of a solid. The solid was collected by filtration, washed with water (2 x 100 mL) and dried in vacuo to give compound B-26 (5.2 g, 79% yield) as a white solid. LCMS (B): tR=0.847 mi, (ES) m/z (M+H)237.0.

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, 3,4-Dichloro-2-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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Some common heterocyclic compound, 104-77-8, name is 3-Chloro-N,N-diethylpropan-1-amine, molecular formula is C7H16ClN, 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. Recommanded Product: 104-77-8

Preparation 88 4-(Diethylamino)-1-(4-fluorophenyl)-1-butanone A suspension of 73.1 g (0.489 mol) 3-(diethylamino)-propyl chloride and 11.87 g (0.489 mol) of magnesium in 300 mL of tetrahydrofuran is initiated with 0.25 mL of 3M ethylmagnesium bromide in diethyl ether and is refluxed overnight. After this time, the reaction is allowed to cool to 40 C. and is treated with 29.6 g (0.245 mol) of 4-fluorobenzonitrile. The initial exotherm is followed by applied heat and the reaction is refluxed for 3 hr. After this time, the reaction is allowd to cool to room temperature and is quenched with 250 mL of water. This mixture is extracted with 2*250 mL of methylene chloride. The combined organic layers are acidifed to pH=1 with 2N aq. hydrochloric acid and the resulting layers separated. The aqueous extract is washed with 100 mL of methylene chloride and is made basic with 4N of sodium hydroxide. The aqueous mixture is extracted with 3*300 mL of methylene chloride. The combined organic layers are dried over sodium sulfate, filtered and the solvent distilled in vacuo to provide crude title compound. This liquid is distilled under vacuum to provide the title compound. NMR (CDCl3): delta=1.04(t,6), 1.92(m,2), 2.52(m,6), 3.20(t,2), 7.14(t,2) and 8.02 (m,2)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104-77-8, its application will become more common.

Reference:
Patent; Schering A.G.; US4851526; (1989); A;,
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These common heterocyclic compound, 452-66-4, name is 4-Chloro-1-fluoro-2-methylbenzene, 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. Product Details of 452-66-4

General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2×10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 4-Chloro-1-fluoro-2-methylbenzene was borylated using the general procedure described above. After the workup, a white solid ( ) was obtained (0.173 g, 64%): mp 64-65 C.; 1H NMR (500 MHz, CDCl3) delta 7.49 (dd, J=3.0, 6.5 Hz, 1H), 7.22 (dd, J=2.0, 6.5 Hz, 1H), 2.23 (d, J=2.0 Hz, 3H), 1.34 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 163.9 (d, J=247.5 Hz), 134.2 (d, J=5.7 Hz), 133.4 (d, J=8.5 Hz), 128.4 (d, J=2.9 Hz), 126.6 (d, J=21.9 Hz), 84.1, 24.7, 14.5 (d, J=3.9 Hz); 19F NMR (470 MHz, CDCl3) delta 109.9; 11B NMR (160 MHz, CDCl3) delta 29.8 (br s).

The synthetic route of 4-Chloro-1-fluoro-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); A1;,
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Synthetic Route of 445-13-6, 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. 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Phenyl [3-chloro-4-(trifluoromethyl)phenyl]carbamate; Phenyl chloroformate (0.86 mL) was added slowly to a stirring solution of 3-chloro-4- trifluoromethyl aniline (933 mg) in THF (10 mL) containing pyridine (1.07 mL) under an argon atomosphere. The reaction was stirred for 18 h then diluted with ethyl acetate (35 mL) and IM HCl (20 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 then dried (MgSO4), filtered and evaporated. Trituration with 1:9 EPO EtOAc dsohexanes (10 mL) at reflux followed by cooling to RT afforded a solid which was filtered to afford 1.15 g of the title compound.

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-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/67401; (2006); A1;,
Chloride – Wikipedia,
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Synthetic Route of 694-80-4, 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. 694-80-4, name is 1-Bromo-2-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-nitroaniline 6.9g 49.95mmol in toluene (100mL), bromochlorobenzene 9.56g (49.95mmol), tris(dibenzylideneacetone) dipalladium(0)(tris(dibenzylideneacetone)dipalladium(0)), 1.44g (2.5mmol) , BINAP 2.33g (3.75mmol), was put cesium carbonate(caesium carbonate) 32.6g (99.91mmol) was refluxed at 120 C under a nitrogen atmosphere. After the reaction was completed after the filters using a Celite (celite) and Florisil (florisil) and washed with MC. By column chromatography and purified using an MC and Hex to give the title compound 1-5 10.7g (86%).

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

Reference:
Patent; Hee SungMaterial Co., Ltd; Go, Hay Jin; Kim, Sin Tae; Kim, Gi Yong; Lee, Do Hyung; Uhm, Sung Jin; Lee, Ju Dong; (37 pag.)KR2015/30056; (2015); A;,
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Related Products of 2401-24-3, The chemical industry reduces the impact on the environment during synthesis 2401-24-3, name is 2-Chloro-5-methoxyaniline, I believe this compound will play a more active role in future production and life.

To a solution of 2-Chloro-5-methoxyaniline (8.00 g, 50.8 mmol) in water (72 mL) is added concentrated HCI (35%) (4.32 mL), then a solution of chloral hydrate (8.43 g, 51 mmol) in water (176 mL) followed by sodium sulfate (24.6 g, 156 mmol). Hydroxylamine (50% in water, 7.68 mL, 254 mmol) is added, and the mixture is refluxed for 1.5h. The RM is cooled to 000, the RM is filtered and the obtained precipitate is washed with water (x 3). The solid is dissolved in acetone and dried with MgSO4. The organic phase is filtered and thesolvent is removed under reduced pressure to afford a dark brown solid. It is triturated in Et20, the solid is removed by filtration, well washed with Et20 and discarded. The filtrate is concentrated to dryness. The resulting orange solid is triturated in DCM, the solid is filtered, and the filtrate is concentrated under vacuum, to be triturated again in DCM before being filtered (x 3). This affords the pure product as a beige solid (4.08 g, 35%). LCMS A: tR = 0.73 mi , [M+H]+=229.07.

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-Chloro-5-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; FRETZ, Heinz; LYOTHIER, Isabelle; POTHIER, Julien; RICHARD-BILDSTEIN, Sylvia; SIFFERLEN, Thierry; WYDER PETERS, Lorenza; POZZI, Davide; CORMINBOEUF, Olivier; (306 pag.)WO2017/85198; (2017); A1;,
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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. 363-51-9, name is 2-Chloro-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Chloro-6-fluoroaniline

To a solution of 2-chloro-6-fluoro aniline (3.0 g, 19.35 mmol) in DCM (10 mL), N- ethyl di-isopropyl amine (8.0 g, 64.00 mmol) was added. The reaction mass was stirred at RT for 30 minutes. The reaction mass was cooled at 0C and drop-wise thiophosgene (5.01 g, 43.47 mmol) was added to the reaction mixture. The reaction mass was stirred RT for 3-4 h. After completion of reaction, the reaction mass was diluted with DCM and purified by using column chromatography to afford 1.0 g of desired title product. 1H NMR (DMSO-d6): delta 7.26 (m, 2H), 7.06 (t, J= 9.6Hz, 1H).

According to the analysis of related databases, 363-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; DESHMUKH, Sanjay; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/153535; (2013); A1;,
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Electric Literature of 932-32-1, 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. 932-32-1, name is 2-Chloro-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Example 9-28; Compound 1 (80 mg) was suspended in methylene chloride (12 ml), and then thereto were added DMF (9 mul) and oxalyl chloride (94 mul), and the mixture was heated to reflux for an hour. The reaction solution was cooled, and then concentrated under reduced pressure. The residue was suspended in chloroform (18 ml), and then thereto was added Compound 2 (180 mul). The mixture was stirred at room temperature for 90 minutes. To the reaction mixture was added water, and the mixture was separated, and then the solvent of the organic layer was distilled away under reduced pressure. To the residue were added THF (5 ml), methanol (1 ml) and 1N-aqueous sodium hydroxide solution (550 mul), and the mixture was stirred at room temperature for an hour. The reaction mixture was diluted with ethyl acetate, and then washed with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent chloroform-ethyl acetate 50:50 to 0:100 gradient), and then the resulting solid was triturated by a mixed solvent of ethyl acetate-n-hexane to give Compound 3 (47 mg) as a colorless powder.MS (APCI) 343/345 [M+H]+

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

Reference:
Patent; Yamaguchi, Tetsuo; Ushirogochi, Hideki; Hirai, Miki; Imanishi, Yasuhiro; US2012/16117; (2012); A1;,
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