Tag: M.W=100-200

Synthetic Route of 626-43-7, 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 626-43-7 as follows.

General procedure: 14 Typical continuous diazotization procedure: Material A (50 mL of aqueous solution containing amine (100 mmol), fluoroboric acid (120 mmol), hydrochloric acid (180 mmol)), and material B (50 mL of aqueous solution containing sodium nitrite (105 mmol)) were pumped into the T-joint at 4 mL/min, respectively, after a residence time of about 15 s at 25 C in a reacting tube, the mixture flowed through the outlet and accumulated in the cooling vessel. Vigorous stirring was maintained. The solid was filtered with suction after the slurry was cooled to -5 C. The solid was washed with methanol and then dried in vacuo to yield the corresponding diazonium tetrafluoroborate. 15 Typical continuous fluorodediazoniation procedure: Slurry of the diazonium tetrafluoroborate prepared as above in 300 mL of cosolvent was introduced into a reacting tube continuously at a flow rate of 4 mL/min. The mixture was maintained for 1 min at setting temperature and then cooled in the tandem tube. The collected liquid was washed with aqueous NaOH and water, nearly colorless liquid was obtained.

According to the analysis of related databases, 626-43-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yu, Zhi-Qun; Lv, Yan-Wen; Yu, Chuan-Ming; Su, Wei-Ke; Tetrahedron Letters; vol. 54; 10; (2013); p. 1261 – 1263;,
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104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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. name: 1-(4-Chlorophenyl)-N-methylmethanamine

REFERENTIAL EXAMPLE 2 Dissolved in toluene was 3.1 g (0.02 mole) of 4-chloro-N-methyl-benzylamine, followed by an addition of a catalytic amount of pyridine and a further dropwise addition of 1.8 g (0.022 mole) of diketene at room temperature. After stirring the reaction mixture at room temperature for 3 hours, it was poured in water and then extracted with toluene. Subsequent to purification, N-methyl-N-(4-chlorobenzyl)acetamide was obtained in an oily form.

The synthetic route of 104-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Toyo Jozo Co., Ltd.; US4736038; (1988); A;,
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Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-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 4863-91-6, Application In Synthesis of 3-Chloro-5-fluoroaniline

EXAMPLE A-12 N-(3-chloro-5-fluorophenyl)-N’-t-pentylthiourea A solution of 8.5 g of 3-chloro-5-fluoroaniline in 150 ml of benzene was refluxed. To the solution was added 2.2 g of thiophosgene in 10 ml of benzene dropwise with stirring. The mixture was stirred at the same temperature for 3 hours, cooled to room temperature and filtered to remove insoluble matter. The filtrate was evaporated in vacuo and filtered again to remove insoluble matter. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography using n-hexane as a solvent. The resulting oil was dissolved in 30 ml of benzene and reacted with 3.4 g of t-pentylamine with stirring at room temperature for 30 minutes. The reaction mixture was evaporated in vacuo and the resulting solid recrystallized from cyclohexane to give 2.2 g of the title compound as colorless needles melting at 116.0-117.5 C. NMR (DMSO-d6, delta ppm): 0.82 (3H, t), 1.42 (6H, s), 1.93 (2H, q), 7.0-7.1 (1H, m), 7.4-7.7 (3H, m), 9.58 (1H, bs).

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

Reference:
Patent; Kanebo, Ltd.; US5087640; (1992); A;,
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Synthetic Route of 15205-11-5,Some common heterocyclic compound, 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, molecular formula is C7H7ClFN, 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 173; lambda/-[(2-chloro-4-fluorophenyl)methyl]-2-[1-(2-hydroxyethyl)-5- (trifluoromethyl)-1 H-pyrazol-4-yl]acetamide (E173) Crude [1-(2-hydroxyethyl)-5-(trifluoromethyl)-1 H-pyrazol-4-yl]acetic acid (6.0 g, -6.52 mmol, prepared as described below) was suspended in dimethylformamide (8 ml) and to this was added water soluble carbodiimide (1.5 g, 7.82 mmol), 1- hydroxybenzotriazole (1.06 g, 7.82 mmol), N-ethyl morpholine (2.49 ml, 19.56 mmol), and [(2-chloro-4-fluorophenyl)methyl]amine (1.25 g, 7.82 mmol). The mixture was stirred at room temperature overnight and then partitioned between ethyl acetate (50 ml) and water (50 ml). The organic phase was separated and washed with more water (2 x 20 ml), dried over anhydrous sodium sulphate, filtered, and concentrated to an orange oil. This material was purified by automated flash-silica column chromatography (Biotage SP4), eluting with 0-100% ethyl acetate in hexane, to give lambda/-[(2-chloro-4-fluorophenyl)methyl]-2-[1-(2-hydroxyethyl)-5-(trifluoromethyl)-1 H- pyrazol-4-yl]acetamide as a sticky white solid (~1 g). LC/MS [M+H]+ = 381 , retention time = 2.47 minutes.

The synthetic route of 15205-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/138876; (2008); A1;,
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32768-54-0, name is 2,3-Dichlorotoluene, 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. Formula: C7H6Cl2

Example 1: Synthesis of 2,3-dichlorobenzotrichloride; A UV photochlorination reactor was loaded with 245 g of 2,3-dichlorotoluene (1.52 moles) and 1225 g of CCl4. The reactor was heated to 75 0C and chlorine was introduced at a flow of 190 g/h. At the end of the reaction, the flow is decreased to minimize break-through of chlorine. The crude mixture was analyzed showing a content of 2,3-dichlorobenzal chloride < 0.2 %. The solvent CCl4 was distilled from the reaction mixture at 600 to 800 mbar. The crude product was then let to distil at 13 mbar and 128 0C giving 334.2 g of 2,3- dichlorobenzotrichloride with a GC assay of 98.2 %. Yield was 81.6 %.; Example 3: Synthesis of 2,3-dichlorobenzotrichloride; A UV photochlorination reactor was loaded with 220.5 g of 2,3-dichlorotoluene (1.37 moles) and 1584 g of CCl4. The reactor was heated to 75 0C and chlorine was introduced at a flow of 190 g/h. At the end of the reaction, the flow was decreased to minimize break-through of chlorine. The crude mixture was analyzed showing a content of 2,3-dichlorobenzal chloride < 0.2 %. The solvent was distilled from the reaction mixture (1808 g) giving 1351 g of CCl4. The crude 2,3-dichlorobenzotrichloride (366.5 g) had a GC assay of 96.0 %. Yield was 97.1%.; Example 5: Synthesis of 2,3-dichlorobenzotrichloride; A UV photochlorination reactor was loaded with 1042 g of 2,3-dichlorotoluene (6.47 moles). The reactor was heated to 100 0C and chlorine was introduced at a flow of 370 g/h. At the end of the reaction, the flow was decreased to 40 g/h to minimize break-through of chlorine. The crude mixture was analysed showing a content of 2,3-dichlorobenzal chloride of 0.3 %. The 2,3-dichlorobenzotrichloride (1675.5 g) was obtained with a GC assay of 97.2 %. Yield was 95.2 %. The synthetic route of 32768-54-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; CALAIRE CHIMIE SAS; WO2007/138075; (2007); A1;,
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20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, 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. COA of Formula: C8H7ClO2

General procedure: Suspension of the appropriate 3-amino-1,1-dioxo-1,4,2-benzodithiazine derivative 4a-h (0.5 mmol), anhydrous K2CO3 (1.5 mmol, 0.21 g) and the appropriate alkyl chloride (0.6 mmol) in dry THF (5 ml) was heated at reflux for 20-24 h, then cooled in ice-bath and filtered off. The crude product was suspended in 5 ml of water, heated gently to ca. 50 C; and cooled with vigorous stirring until granular precipitate appeared. Filtering off and washing with cold water and diluted EtOH gave pure potassium salts. 4.5.7 ;N-{2-[(1,3-Benzodioxol-5-yl)methylthio]-4-chloro-5-(5-phenyl-1,3,4-thiadiazol-2-yl)benzenesulfonyl}cyanamide potassium salt (5k) ;Starting from 4c (0.204 g) and 1,3-benzodioxol-5-ylmethyl chloride (0.102 g). Yield: 0.287 g (99%): m.p. 285-287 C; IR (KBr): nu 3443, 2924, 2853, 2179, 1652, 1623, 1577, 1501, 1489, 1357, 1129 cm-1; 1H NMR (500 MHz, DMSO-d6): delta 4.35 (s, 2H, SCH2), 6.01 (s, 2H, OCH2O), 6.89 (d, J = 7.81 Hz, 1H, Ar), 6.97 (d, J = 7.81 Hz, 1H, Ar), 7.05 (s, 1H, Ar), 7.58-7.60 (m, 3H, Ar), 7.68 (s, 1H, Ar), 8.07-8.08 (m, 2H, Ar), 8.69 (s, 1H, Ar); Anal. C23H14ClKN4O4S3 (C, H, N).

The synthetic route of 20850-43-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Brozewicz, Kamil; Slawinski, Jaroslaw; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 384 – 394;,
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Reference of 106-39-8,Some common heterocyclic compound, 106-39-8, name is 1-Bromo-4-chlorobenzene, molecular formula is C6H4BrCl, 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: In a thermostatted bath at 25C (or 60C for compounds 18 and 28), a 25 mL Schlenk flask was charged in air with a magnetic stir bar, arylbromide (0.5 mmol), arylboronic acid (0.6 mmol), K2CO3 (0.6 mmol), 1 (26.6 mg, 1mol-%), ethanol (1.5 mL), and water (0.5 mL). The reaction mixture was kept under vigorous stirring until the GC control showed no residual aryl bromide in solution. Water (10 mL) was added to the suspension and the organics were extracted with dichloromethane (3×10 mL). The solution was dried over Na2SO4 and then passed through a column filled with silica gel (diatomaceous earths were used in the case of compound 28). Elimination of the solvent under vacuum gave the desired biaryl as white microcrystalline solid. Purity (96÷99%) was established by GC and 1H NMR. 1H and 13C{1H} NMR data of compounds 8-28. Spin multiplicity is given by s=singlet, br s=broad singlet, q=quartet, st=septet, qq=quartet of quartets, ddd=doublet of doublets of doublets, m=unresolved multiplet. 4-Chloro-4′-methyl-1,1′-biphenyl (16). Yield 96%. C13H11Cl (202.68): calcd. C 77.04, H 5.47; found C 76.95, H 5.48. 1H NMR (CDCl3): delta = 7.55-7.33 (6H, m), 7.29-7.16 (2H, m), 2.39 (3H, s, CH3) ppm. 13C NMR (CDCl3): delta = 139.5, 137.4, 137.0, 132.9, 129.5, 128.8, 128.1, 126.7, 21.0 (CH3) ppm.

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

Reference:
Article; Del Zotto, Alessandro; Colussi, Sara; Trovarelli, Alessandro; Inorganica Chimica Acta; vol. 470; (2018); p. 275 – 283;,
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Related Products of 1005-56-7,Some common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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 solution of cholesterol (863 mg, 2.23 mmol) in CH2Cl2 (10 mL) were added pyridine (485 muL, 6.00 mmol) and phenyl chlorothionoformate (277 muL, 2.00 mmol) (For other substrates, CH3CN was used in place of CH2Cl2.). The mixture was stirred at room temperature for 50 min and diluted with EtOAc. The solution was washed with brine and dried over anhydrous MgSO4. After concentration, the residue was purified by flash chromatography on silica gel (hexane?hexane/EtOAc=10/1) to give thiocarbonate 5b (1.04 g, 1.99 mmol, 100%).

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

Reference:
Article; Kobayashi, Shoji; Kuroda, Hiroyuki; Ohtsuka, Yuta; Kashihara, Takashi; Masuyama, Araki; Watanabe, Kiyoshi; Tetrahedron; vol. 69; 10; (2013); p. 2251 – 2259;,
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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. 623-12-1, name is 1-Chloro-4-methoxybenzene, A new synthetic method of this compound is introduced below., Safety of 1-Chloro-4-methoxybenzene

General procedure: Palladacycle C1 (0.005mmol), olefin (0.75mmol), aryl chloride (0.5mmol), K2CO3 (1.0mmol) and DMF/H2O (2ml, 1:1) were added to a small tube and the mixture was heated to 110C for 6h in the presence of air. The reactions were monitored by thin-layer chromatography (TLC). At the end of the cross-coupling reactions, the mixture was cooled, extracted with n-hexane:EtOAc (8:2), filtered and purified by recrystallization from ethanol and water or purified by silica gel column chromatography (n-hexane:EtOAc, 8:2).

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; Javad Sabounchei, Seyyed; Hashemi, Ali; Yousefi, Abed; Gohari Derakhshandeh, Parviz; Karamian, Roya; Asadbegy, Mostafa; Van Hecke, Kristof; Polyhedron; vol. 135; (2017); p. 1 – 9;,
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Application of 886762-39-6, These common heterocyclic compound, 886762-39-6, name is 3,4-Dichloro-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.

Example 31 (£)-N-(4-((3,4-Dichloro-2-fluorophenyl)a^ 2H-[l,4]dioxino[2,3-c]pyrrol-6(3 -yl)but-2-enamide Step 1) N-(3,4-dichloro-2-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine A solution of 4-chloro-7-fluoro-6-nitroquinazoline (10.00 g, 44.0 mmol) and 3,4-dichloro-2-fluoroaniline (8.40 g, 46.5 mmol) in isopropanol (150 mL) was heated to 70 C and stirred for 5.0 hours. The reaction mixture was then cooled to 25 C, and a yellow solid precipitated out. The mixture was filtered. The filtered cake was washed with isopropanol (50 mL) and dried under vacuum to give the title compound as a yellow solid (11.4 g, 70.0%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) m/z : 371.0 [M+H]+.

The synthetic route of 886762-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LIU, Bing; LIU, Jinlei; ZHANG, Jiancun; ZHENG, Changchun; WO2014/177038; (2014); A1;,
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