Tag: M.W=100-200

Related Products of 2106-04-9, These common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-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.

Step 1 .2: Ethyl-5-((3-chloro-2-fluorophenylamino)(4-chlorophenyl)methyl)-1-isopropyl-2-(2- methoxyphenyl)-1 H-imidazole-4-carboxylate 3-chloro-2-fluoroaniline (90 mg, 0.621 mmol) was added to a solution of the product of step 1.3 (242 mg, 0.477 mmol) in dioxane (5 ml) and stirred at 60C over night. 3-Chloro- 2-fluoroaniline (90 mg, 0.621 mmol) was added again to the reaction mixture and heated at 100C for 3 hr. The solution was diluted with EtOAc and washed twice with a 5% aqueous citric acid solution. The water phase was back extracted with EtOAc and the combined organic layers were washed with saturated aqueous NaHC03, dried over Na2S04 and evaporated to afford 800 mg of brown oil. The residue was purified by preparative HPLC (Waters xBridge (30 / 100 mm), 0.1 % TFA-water/0.1 % TFA-acetonitrile; gradient acetonitrile 30 to 60% in 10 min, then 5 min at 60%, 60 – 90% in 10 min and 2 min at 100%) to afford 176 mg (0.313 mmol, 65.6% yield) of the title compound. LCMS: (M+H) = 556/557; tR = 1 .46 min (LC-MS 3). HPLC: tR = 5.35 min (H PLC 2) 1 H-NMR (MeOD, 600.13 MHz) delta ppm 7.52 (t, 1 H) 7.39-7.30 (m, 5H) 7.12 (m, 1 H) 7.07 (t, 1 H) 6.96 (t, 1 H) 6.86 (t, 1 H) 6.77 (t, 1 H) 6.72-6.30 (m, 1 H) 4.37 (quin, 1 H) 4.27 (q, 2H) 3.77 (s, 3H) 1 .31 -1.05 (m, 9H)

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; MAH, Robert; MASUYA, Keiichi; SCHLAPBACH, Achim; VAUPEL, Andrea; WO2014/115077; (2014); A1;,
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Related Products of 626-43-7, These common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, 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.

5-Bromo-2-methoxybenzenesulfonyl chloride(857mg, 3mmol) was dissolved in dichloromethane(6mL). A solution of 3,5-dichloroaniline(510mg, 3.15mmol) and pyridine(261mg, 3.3mmol) in dichloromethane(2mL) was added dropwise under ice cooling and argon atmosphere, and the mixture was stirred at room temperature for 6 hours. After the reaction mixture was diluted with dichloromethane, washed successively with 2N hydrochloric acid, water, and brine, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was crystallized from n-hexane-ethyl acetate to give 5-bromo-2-methoxy-N-(3,5-dichloro)benzenesulfonamide(900mg, 73.0%) as a white crystal.1H-NMR(DMSO-d6): delta 4.03(3H, s), 6.92(1H, d, J=9.0Hz), 7.01(2H, d, J=1.8Hz), 7.07-7.08(1H, m), 7.24(1H, brs), 7.63(1H, dd, J=8.7, 2.4Hz), 7.99(1H, d, J=2.4Hz).

The synthetic route of 626-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1512396; (2005); A1;,
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Reference of 501-29-1,Some common heterocyclic compound, 501-29-1, name is 1-Chloro-2-fluoro-4-methoxybenzene, molecular formula is C7H6ClFO, 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.

To a mixture of 1-chloro-2-fluoro-4-methoxybenzene (5.00 g, 31.1 mmol) in cone. H2S04 (30 mL) at 0-10eC was added portionwise potassium nitrate (3.78 g, 37.4 mmol) and the reaction was stirred at OeC for 2 h. The reaction was quenched with ice water and filtered. The obtained solids were recrystallized with hexanes to give 4.50 g 3 (70%) of 1-chloro-2-fluoro-4-methoxy-5-nitrobenzene. 1HNMR (400 MHz, DMSO- d6) U8.30 (d, J = 2.0 Hz, 1H), 7.61 (d, J = 2.3 Hz, 1H), 3.96 (s, 3H); ESI-MS (m/z) 205.76 (MH)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-2-fluoro-4-methoxybenzene, its application will become more common.

Reference:
Patent; LUPIN LIMITED; KUKREJA, Gagan; IRLAPATI, Nageswara, Rao; JAGDALE, Arun, Rangnath; DESHMUKH, Gokul, Keruji; VYAVAHARE, Vinod, Popatrao; KULKARNI, Kiran, Chandrashekhar; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (366 pag.)WO2018/20474; (2018); A1;,
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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. 2613-32-3, name is 2-Chloro-4,5-difluoroaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

General procedure: Different substituted anilines 3 (10.0mmol) were added to a solution of hydrochloric acid (15mL, 3-4mol L-1), and then sodium nitrite (0.76g, 10.5mmol) dissolving in water (3mL) was dropwise added at 0C. After 0.5h, tin (II) chloride (4.5g, 20mmol) in 10mL of concentrated hydrochloric acid was dropwise added to the above mixture. The reaction was vigorously stirred for 2h at 0C, and then was filtered and washed with 3-4molL-1 hydrochloric acid. The precipitate was dissolved in water and filtered. The filtrate was adjusted to pH 12, and the generated solid was collected and dried to afford different substituted phenylhydrazine 4a-k.

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; Liu, Jing-Bo; Li, Feng-Yun; Dong, Jing-Yue; Li, Yu-Xin; Zhang, Xiu-Lan; Wang, Yuan-Hong; Xiong, Li-Xia; Li, Zheng-Ming; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3541 – 3550;,
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Synthetic Route of 367-22-6, These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-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.

A. 4-Chloro-3-fluorobenzenesulfonyl chloride The title compound was prepared using the method of Organic Syntheses Vol. 60, 121-124. A solution of 4-chloro-3-fluoro aniline (5 g, 0.034 mol) in glacial HOAc (10 mL) was added slowly to concentrated HCl (30 mL) to form a white precipitate. The mixture was cooled in a dry ice-ethanol bath. A solution of NaNO2 (3.08 g, 0.045 mol) in H2O (5 mL) was added dropwise while stirring with a glass rod, maintaining the temperature at or below -5 C. The mixture was stirred intermittently while in the bath for 1 h. In a separate flask, HOAc (40 mL) was saturated with SO2 using a gas dispersion tube (about 15 min). To this acetic acid solution was added cuprous chloride (0.68 g, 7 mmol), which gave a grey solution. The SO2 was bubbled through until the solution turned green-blue. The solution was cooled in a dry ice-ethanol bath and the diazonium salt mixture was added in portions while stirring with a glass rod. After the addition was complete, the reaction was removed from the bath and allowed to come to 0 C. over 15 to 20 min. with occasional stirring. The reaction was poured onto ice (100 mL) and extracted with CH2Cl2 (2*100 mL). The combined organic layer was washed with saturated NaHCO3 (3*40 mL), dried (Na2SO4), filtered and concentrated to afford a golden oil. The crude product was purified by silica gel column chromatography, eluding with a gradient of 10% to 15% CH2Cl2/hexanes to afford the title compound (5.5 g, 70%) as a golden oil. Mass Spectrum (-ESI): 209 [M-Cl+O]-.

Statistics shows that 4-Chloro-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 367-22-6.

Reference:
Patent; Wyeth; US2007/249722; (2007); A1;,
Chloride – Wikipedia,
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1435-48-9, 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. 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add NaH (60% in mineral oil, 0.132 g, 3.32 mmol) to 1- (benzyl-methyl-amino)-4-methyl-3-ol (0.498 g, 2.21 mmol) in anhydrous DMSO (10 mL). After 30 minutes, add 1, 3-dichloro-4- fluorobenzene (0.474 g, 2.87 mmol) and then heat the reaction mixture at 60C overnight. Cool the mixture and partition between EtOAc and water. Separate the layers and extract the aqueous layer with EtOAc. Combine the organic extracts, wash with aqueous saturated sodium chloride solution, dry over anhydrous Na2SO4, filter, and concentrate in vacuo. Purify the residue on silica gel eluting with 5% 2N NH3 in MeOH/dichloromethane to give benzyl- [3- (2, 4-dichloro- phenoxy) -4-methyl-pentyl] -methyl amine (0.385 g, 48%). Mass spectrum (ion spray): m/z = 366 (M+1),’H NMR (CD30D) 8 734 (d, 1H), 7.28-7. 17 (m, 6H), 7.06 (d, 1H), 4.35-4. 31 (m, 1H), 3.48 (dd, 2H), 2.55-2. 43 (m, 2H), 2.19 (s, 3H), 1.98-1. 83 (m, 3H), 0.98 (dd, 6H).

The synthetic route of 1435-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/92835; (2005); 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 10061-02-6 as follows. 10061-02-6

To a 3000 mL three-necked flask equipped with a thermometer, a condenser, a constant pressure dropping funnel and a stirrer, 437.2 g (1.0 mol) of fipronil, 60 g (1.5 mol) of NaOH and 1500 mL of ethanol were added, 138.8 g (1.25 mol) of 1,3-trans-dichloropropene was added dropwise at -10 C, and after completion of the dropwise addition, the temperature was controlled at -10 C for 24 hours. The reaction was completed, filtered, the filtrate was adjusted with concentrated hydrochloric acid system pH to neutral, under 40 C vacuum solvent recovery, the residue was slowly added dropwise to ice water, the temperature was controlled at 0 ~ 5 crystallization, filtration, residue by methanol Crystallization, filtration, drying, to give a white crystalline solid 390.0g. Yield 72.8%, liquid chromatography quantitative analysis of content of 95.5%.

According to the analysis of related databases, 10061-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hunan Chemical Institute Co., Ltd.; Du Shenghua; Lan Shilin; Liu Weidong; Liu Yuan; Huang Chaoqun; Wang Yanli; Luo Liangming; (6 pag.)CN105949126; (2016); A;,
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74788-46-8,Some common heterocyclic compound, 74788-46-8, name is 1-(4-Chlorophenyl)propan-1-amine, molecular formula is C9H12ClN, 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 3: 4-amino-N-Q-(4-chlorophenyl)propyl)-l-(7H-pyrrolo[2.,3-dlpyrimidin-4- yl)piperidine-4-carboxamideO-(7-Azabenzotriazol- 1 -yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (0.209 g) was added in one portion to 4-(tert-butoxycarbonylamino)-l-(7H-pyrrolo[2,3- d]pyrimidin-4-yl)piperidine-4-carboxylic acid (Intermediate 1) (0.181 g), l-(4- chlorophenyl)propan-l -amine (0.085 g) and DIPEA (0.262 mL) in DMA (10 mL) at 250C under nitrogen. The resulting solution was stirred at 6O0C for 4 hours. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using IN ammonia/MeOH and pure fractions were evaporated to dryness. This crude material was then treated with a 20% solution of TFA in DCM (10 mL) and stirred at room temperature for 2 hours. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using IN ammonia/MeOH and pure fractions were evaporated to dryness. This material was purified by preparative LCMS using decreasingly polar mixtures of water (containing 1% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 4-amino-N-(l-(4-chlorophenyl)propyl)-l- (7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide as a white solid (0.138 g, 66.8 %).1U NMR (400.13 MHz, DMSOd6) delta 0.87 (3H, t), 1.42 – 1.55 (2H, m), 1.72 – 1.79 (2H, m), 1.91 – 2.05 (2H, m), 2.21 (2H, s), 3.54 – 3.62 (2H, m), 4.38 – 4.45 (2H, m), 4.65 – 4.70 (IH, m), 6.61 (IH, dd), 7.18 (IH, dd), 7.32 – 7.37 (4H, m), 8.31 (IH, d), 8.12 (IH, s). MS m/e MH+ 413.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 74788-46-8, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/47563; (2009); A1;,
Chloride – Wikipedia,
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6940-78-9, The chemical industry reduces the impact on the environment during synthesis 6940-78-9, name is 1-Bromo-4-chlorobutane, I believe this compound will play a more active role in future production and life.

Production Example 1 Synthesis of dihydrate of Compound (I) Methanol (149 L), 7-hydroxy-1H-quinolin-2-one (14.87 kg), and potassium hydroxide (6.21 kg) were mixed in a reaction vessel, and the resulting mixture was stirred. After dissolution, 1-bromo-4-chlorobutane (47.46 kg) was added thereto, and the resulting mixture was stirred under reflux for seven hours. Thereafter, the mixture was stirred at 10 C. for one hour. The precipitated crystal was centrifuged and washed with methanol (15 L). The wet crystal was collected and placed in a tank. Water (149 L) was added thereto, followed by stirring at room temperature. After centrifugation, the result was washed with water (30 L). The wet crystal was collected and placed in a tank. After adding methanol (74 L), the mixture was stirred under reflux for one hour, cooled to 10 C., and then stirred. The precipitated crystal was centrifuged and washed with methanol (15 L). The separated crystal was dried at 60 C. to obtain 7-(4-chlorobutoxy)-1H-quinolin-2-one (15.07 kg).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-chlorobutane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sato, Tetsuya; Minowa, Takuya; Hoshika, Yusuke; Toyofuku, Hidekazu; US2015/86632; (2015); A1;,
Chloride – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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 13726-14-2. 13726-14-2

Ethyl 2-chloro-4-(4-chloro-3-methoxyphenylamino)pyrimidine-5-carboxylate (RJ1- 061): A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). XH NMR (400 MHz, DMSO-) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, J= 2.3 Hz, 1H), 7.43 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 8.6, 2.3 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, J= 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

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 4-Chloro-3-methoxyaniline.

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,
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