Tag: M.W=200-300

These common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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. Quality Control of 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline

To a solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (500 mg, 2.46 mmol) and 3-amino-5-cyclopropylpyrazole (303 mg, 2.46 mmol) in DMF (10 mL) is added triethylamine (0.357 mL, 2.56 mmol) followed by sodium iodide (368 mg, 2.46 mmol) and the reaction mixture is heated at 90 C. for 20 h. The reaction mixture is partitioned between ethyl acetate and aqueous saturated NaHCO3. The organic layer is washed with brine and evaporated in vacuo. The residue is purified by flash chromatography (SiO2, hexane/AcOEt gradient) to give (2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine.

The synthetic route of 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bebbington, David; Charrier, Jean-Damien; Golec, Julian; Miller, Andrew; Knegtel, Ronald; US2005/38023; (2005); 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. 53531-69-4, name is (4-Bromophenyl)methanesulfonyl chloride, A new synthetic method of this compound is introduced below., Application In Synthesis of (4-Bromophenyl)methanesulfonyl chloride

General procedure: Two-step one-pot method: Add bromobenzyl mercaptan to acetonitrile, then add chlorinating reagent, monitor with spot plate, and transfer to ice water bath after reaction.Add 4 equivalents of an acid binding agent such as pyridine.After slowly adding 7-amino-N-propylquinolinone in acetonitrile,The plate is monitored for reaction, after the reaction, pickling, drying,Further, the abscisic acid receptor agonist can be obtained by column chromatography or recrystallization,

The synthetic route of 53531-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaoyang University; Huang Zhiyou; (7 pag.)CN109678797; (2019); A;,
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Electric Literature of 1996-30-1, 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. 1996-30-1 name is 3-Bromo-4-fluorochlorobenzene, 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.

General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluorochlorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Krake, Susann H.; Martinez, Pablo David G.; McLaren, Jenna; Ryan, Eileen; Chen, Gong; White, Karen; Charman, Susan A.; Campbell, Simon; Willis, Paul; Dias, Luiz Carlos; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 929 – 936;,
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Reference of 51572-93-1,Some common heterocyclic compound, 51572-93-1, name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, molecular formula is C7H8Cl3NO, 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: To a solution of 3ae3e (1 mmol) in anhydrous ethanol (10 mL),corresponding O-benzylhydroxylamine hydrochloride (1 mmol)and NaOAc (1.2 mmol) were added and the resulting solution wasstirred at the room temperate for 3 h. The mixture was concentratedand taken in ethyl acetate (20 mL), washed with water(20 mL), saturated sodium chloride solution (20 mL) and dried oversodium sulfate. The resulting solution was concentrated and thepurification of the residue by recrystallization from ethanol yieldedthe desired compounds 4a-4t

The synthetic route of 51572-93-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Li, Qing-Shan; Ren, Zi-Li; Chu, Ming-Jie; Sun, Jian; Zhang, Xin; Xing, Man; Zhu, Hai-Liang; Cao, Hai-Qun; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 586 – 593;,
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Reference of 1996-29-8, 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N. 2-CHLORO-5-CYCLOPROPYL-6-FLUOROANILINE The preparation is an adaptation of a method described in Tetrahedron Lett, Vol. 37, p. 6551 (1996). A solution of lithium DIIOSOPROPYL amide is generated by adding n-BuLi (360 mL of 2 M solution in THF) to diisopropylamine (73 g, 0.722 mol) in 500 mL of anhydrous THF while a reaction temperature OF-60C is maintained by cooling in dry-ice acetone bath. After stirring for 30 minutes, 1-bromo-4-chloro-2-fluorobenzene (75 g, 0.36 mol) is added and stirring maintained AT-70C for 2 hours. The cold solution is then transferred, via a canula, under an inert atmosphere to a suspension of solid C02 (100 g, excess) in anhydrous ET2O. The mixture is allowed to warm to room temperature with stirring and then the solvent removed by rotary evaporator. The residual solid is treated with 1 N HCI solution until PH = 3.0 and the mixture is filtered. The white solid that is obtained is suspended in 1000 mL of 2 N HCI solution and stirred for an additional 1 hour. The suspension is filtered to collect a white solid which is air dried, suspended in 100 mL of hexanes and collected to give 2-CHLORO-5-BROMO-6-FLUOROBENZOIC acid. 2-Chloro-5-bromo-6-fluorobenzoic acid (91 g, 0.36 mol) is suspended in CH2CI2 (200 mL) and treated with oxalyl chloride (51 g, 0.40 mol) by dropwise addition, immediately followed by the addition of several drops (0.1 mL) of DMF. The mixture is stirred at room temperature for 3 hours during which time the solid completely dissolves and a clear solution is obtained. The solvent is removed by rotary evaporator and the residue is added to 1000 mL of ammonium hydroxide while stirring at 0C. The product is collected by filtration and washed with water to give 2-chloro-5-bromo-6-fluorobenzamide as a white solid. A solution of sodium methoxide is generated by treating metallic sodium (18 g, 0.78 mol) with 1000 mL of anhydrous methanol by dropwise addition under an inert atmosphere. After the metal is completely consumed the solution is heated at reflux temperature for 30 minutes and then cooled to room temperature. 2-Chloro-5-bromo-6-fluorobenzamide (65 g, 0.26 mol) is added and stirring continued for an additional 30 minutes at room temperature. N-BROMOSUCCINIMIDE (92 g, 0.52 mol) is then slowly added via a powder addition funnel. The reaction mixture is warmed to 60C for 30 minutes during which time foaming is observed. The reaction mixture is cooled to room temperature and most of the solvent is removed by rotary evaporator. The residue is partitioned between EtOAc (1000 mL) and water (1000 mL). The organic layer is separated and washed with water (5 x 500 mL) and then brine (2 x 500 mL). The organic layer is dried (MGS04), filtered and concentrated by rotary evaporator to GIVE N- (2-CHLORO-5-BROMO-6-FLUOROPHENYL)-CARBAMIC acid methyl ester as a light yellow solid (m. p. 107-112C). N-(2-chloro-5-bromo-6-fluorophenyl)-carbamic ester methyl ester (8.65 g, 30.6 MMOL), cyclopropylboronic acid (3.16 g, 36.7 MMOL), potassium phosphate (22.8 g, 107 MMOL), palladium acetate (343 mg, 1.53 MMOL) and tricyclohexylphosphine (858 mg, 3.06 MMOL) are combined and stirred in a two-phase solution comprised of toluene (350 mL) and water (75 mL). The mixture is degassed by repeated alternating application of vacuum and positive nitrogen pressure (10 x). The mixture is heated to 95C for 4 days and then cooled to room temperature. The reaction mixture is partitioned between EtOAc (500 mL) and water (500 mL). The organic phase is washed with water (2 x 250 mL), brine (500 mL) and then dried (MGS04) and concentrated by rotary evaporator. The crude product is purified using flash chromatography (7-14% EtOAc/hexanes). After evaporation of the appropriate fractions the product is further purified by treating a solution in ET20 (100 mL) with charcoal, followed by filtration through Celite and evaporation. N- (2-chloro-5- cyclopropyl-6-fluorophenyl)-carbamic acid methyl ester is obtained as a white crystalline solid (m. p. 100-102C). N-(2-CHLORO-5-CYCLOPROPYL-6-FLUOROPHENYL)-CARBAMIC acid methyl ester (2.3 g, 9.4 MMOL) is dissolved in MeOH (50 mL), water (50 mL) and 30% NAOH solution (50 mL). The reaction mixture is heated to reflux temperature for 3 days and then cooled to room temperature. The reaction is concentrated by rotary evaporator to remove most of the methanol and then partitioned between ET20 (250 mL) and water (250 mL). The aqueous phase is extracted again with ET20 (150 mL) and the-combined organic layers washed with brine (250 mL), dried and concentrated by rotary evaporator. The crude product is purified by bulb-to-bulb distillation. 2-Chloro-5-cyclopropyl-6-fluoroaniline is isolated as a colorless oil (b. p. 120-135C at-20 mm of Hg).

The synthetic route of 1-Bromo-4-chloro-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/48314; (2004); A1;,
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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 210532-25-5 as follows. name: 3,5-Difluorobenzene-1-sulfonyl chloride

A solution of 3-(2-chloro-10H-phenothiazin-10-yl)propan-1-amine hydrochloride (0.080 g, 0.244 mmol) in DMF (1.5 ml) was cooled to 0 C, treated with triethylamine (71.0 muL, 0.513 mmol), and 3,5-difluorobenzenesulfonyl chloride (0.057 g, 0.268 mmol). The mixture was warmed to 25 C, and stirred for 2 h. The mixture was poured over saturated aqueous NaCl (50 mL), and extracted with ethyl acetate (3 50 mL). The combined organic extracts were washed with saturated aqueous NaCl (2 50 mL), dried (Na2SO4), and concentrated in vacuo. The residue was dissolved in a minimal amount of CH2Cl2 and purified by flash chromatography (SiO2, 0-35% ethyl acetate-hexanes) to afford the title compound as a white solid triturated from ethyl ether-hexanes (0.0736 g, 65%). 1H NMR (600 MHz, CDCl3) 7.17-7.22 (4H, m), 7.11 (1H, d, J = 8.2 Hz), 7.01 (1H, t, J = 7.6 Hz), 6.95 (2H, m), 6.85 (1H, d, J = 8.1 Hz), 6.81 (1H, s), 5.23 (1H, t, J = 5.9 Hz), 3.93 (2H, t, J = 5.8 Hz), 3.13 (2H, dd, J = 12.2, 6.1 Hz), 1.97 (2H, quintet, J = 5.9 Hz); 13C NMR (150 MHz, CDCl3) 163.7 (d, J = 48.0 Hz), 162.0 (d, J = 44.2 Hz), 146.5, 144.5, 143.4 (t, J = 34.3 Hz), 133.8, 128.6, 128.2, 127.9, 126.0, 124.8, 123.9, 123.3, 116.3 (d, J = 52.7 Hz), 110.6 (dd, J = 85.3, 26.0 Hz), 108.3 (t, J = 100.6 Hz), 45.3, 42.0, 26.3; LCMS m/z 467.1 ([M + H+], C21H17ClF2N2O2S2 requires 467.0).

According to the analysis of related databases, 210532-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kastrinsky, David B.; Sangodkar, Jaya; Zaware, Nilesh; Izadmehr, Sudeh; Dhawan, Neil S.; Narla, Goutham; Ohlmeyer, Michael; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6528 – 6534;,
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Synthetic Route of 14862-52-3,Some common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, molecular formula is C6H3Br2Cl, 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.

Reference Example 1 Synthesis of 3,5-diphenylchlorobenzene The compound entitled was synthesized in accordance with the following scheme. Into a 1 L four-necked glass flask equipped with a thermometer, a reflux condenser and a stirrer, 3,5-dibromochlorobenzene 20.0 g (74.0 mmol), phenylboronic acid 27.0 g (222 mmol), 2.0 mol/l sodium carbonate aqueous solution 285 ml (570 mmol), and toluene:tetrahydrofuran (1:1) solution 500 ml were added, and nitrogen was passed through the solution for 2 hours and 30 minutes. Tetrakistriphenylphosphine palladium(0) 4.28 g (3.70 mmol) was then added, which was reacted for 28 hours at 73 to 75 C. with stirring followed by further addition of phenylboronic acid 4.10 g (33.6 mmol) and tetrakistriphenylphosphine palladium(0) 1.10 g (950 mumol) and reaction for 24 hours at 73 to 75 C. with stirring. After completion of the reaction, the reaction mixture was cooled down to room temperature and separated with the addition of water and toluene, and after the water layer was extracted with toluene and after the organic layers were combined and washed with water, it was dried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained concentrate was purified by silica-gel column chromatography (eluent: hexane) to obtain 3,5-diphenylchlorobenzene 16.0 g as white solid (isolation yield; 82%).

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-Dibromochlorobenzene, its application will become more common.

Reference:
Patent; UBE INDUSTRIES, LTD.; US2011/140044; (2011); A1;,
Chloride – Wikipedia,
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These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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. SDS of cas: 210532-25-5

General procedure: To a solution of intermediate 13 (10mmol) and triethylamine (15mmol) in dichloromethane (20ml), a solution of appropriate acyl chlorides or sulfonyl chlorides (1.05 eq) in dichloromethane (3ml) was added dropwise at room temperature overnight. The mixture was washed with saturated aqueous sodium bicarbonate and brine. After removing the solvent under reduced pressure, the crude product was purified by flash chromatography on silica gel to yield the intermediates 14a-n, 15a-k, 16a-h, 17a-m. Subsequently, to a solution of the above intermediates (2mmol) in methanol/H2O (75%, 10ml) was added lithium hydrate (2.4mmol). The resulting mixture was allowed to warm up to 60C for 4h. The reaction mixture was allowed to cool to room temperature and concentrated under pressure to remove methanol. The resulting mixture was diluted by water and acidified with aqueous HCl (1mol/L) till pH=3. The white solid was collected by filtration, washed with water three times and dried to give the target compounds.

The synthetic route of 3,5-Difluorobenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Yongzhi; Zhao, Yuqian; Wang, Guan; Chen, Yi; Jiang, Yingnan; Ouyang, Liang; Liu, Bo; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 402 – 418;,
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Reference of 19752-55-7, A common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Compound 7B (31.2 g, 55.57 mmol) and Reagent 4 (12.6 g, 55.57 mmol) were put into 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and refluxed. Thereafter, potassium carbonate (23.0 g, 167.70 mmol) was dissolved in 800 ml of water, the resulting solution was introduced into the mixture, the resulting mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (1.9 g, 1.67 mmol) was introduced thereinto. After the reaction for 12 hours, the temperature of the product was lowered to normal temperature and a produced solid was filtered. After the filtration, the solid was washed with 100 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water, and 300 ml of ethanol. The resulting product was dried to prepare Compound 7C (26 g, 80percent). Reagent 4 was purchased from Aldrich.

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; LG Chem, Ltd.; Jung, Min Woo; Lee, Dong Hoon; Huh, Jungoh; Jang, Boonjae; Kang, Minyoung; Heo, Dong Uk; Han, Miyeon; (52 pag.)US2018/244630; (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. 19230-27-4, name is 1,3-Dibromo-2-chlorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3Br2Cl

To a soution of 5- (4,4,55-tetramethy-1 ,3,2-dioxaboroan-2-y-1 H-benzo[d]imidazo2(3H)-one (ntermediate28, 2.0 g, 7.7 mmo), potassium phosphate (3.3 g, 15 mmo), and 1,3-dibromo-2- chorobenzene (2.1 g, 7.7 mmo) in 4:1 dioxane:water (20 mL) was added PdC2(dppf)- CH2C2 (563 mg, 0.77 mmo) at once. The mixture was degassed w[th nitrogen for 10 n,inutes and then heated at 100 C for 16 h. After coong to rt, the reaction mixture wasduted w[th water and extracted with DOM (x3). The combined organic extracts were dried (Na2SO4), ftered and concentrated under reduced pressure. The crude product was trfturated with DCM to provide the tiDe compound as a white sohd (1.7 g, 65% yied). MS (ES): mass cacd. for C13H8BrCN2O, 322.0; m/z found, 322.9 [M+H]. 1H NMR (500 MHz, DMSO-d6)o 10.72 (s, IH), 10.70(s, IH), 7.76(dd, J= 7.9, 1.6 Hz, IH), 746-726 (m,2H), 706 689 (m, 3H).

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; JANSSEN PHARMACEUTICA NV; RAVULA, Suchitra; SWANSON, Devin M.; SAVALL, Bradley M.; AMERIKS, Michael K.; (250 pag.)WO2016/176449; (2016); A1;,
Chloride – Wikipedia,
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