Author: Jessica.F

Reference of 928-50-7,Some common heterocyclic compound, 928-50-7, name is 5-Chloropent-1-ene, molecular formula is C5H9Cl, 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: Sodium azide (0.5 g, 8 mmol) was added to the stirredsolution of chlorides 1b,e,f or tosylates 1c,d (6 mmol) indry DMSO (8 ml) at room temperature. The reactionmixture was stirred at 70C for 15 h, then washed well withwater (3×10 ml) and extracted with CH2Cl2 (2×10 ml). Combined organic layers were dried over MgSO4, filtered,and concentrated to obtain the crude azides 2b-f. Resultingazides were dissolved in Et2O (10 ml), PPh3 (1.6 g, 6 mmol)was added, the reaction mixture was stirred at 0C for 1.5 h.Then water (1 ml) was added and the reaction mixture wasstirred at room temperature overnight. After the completion,the reaction mixture was poured onto crushed ice andextracted with CH2Cl2 (3×10 ml). Organic layers werecombined and dried over MgSO4, filtered, and concentratedunder reduced pressure to obtain amines 3b-f. Solution ofamine 3a-f in CH2Cl2 (10 ml) was stirred with K2CO3(2.2 g, 16 mmol) at 0C for 15 min. Acryloyl chloride(0.6 ml, 7 mmol) was added dropwise at 0C, and themixture was stirred at room temperature for 6 h. Thereaction was monitored by TLC. After completion of thereaction, cold water (10 ml) was added and the mixture wasextracted with CH2Cl2 (3×10 ml). The combined organiclayers were washed with brine, dried over anhydrous MgSO4,filtered, and concentrated under reduced pressure. Thecrude diene amides 4a-f were purified on silica gel column,eluting with EtOAc-petroleum ether with increasing gradient.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloropent-1-ene, its application will become more common.

Reference:
Article; Gondal, Humaira Yasmeen; Buisson, Didier; Chemistry of Heterocyclic Compounds; vol. 52; 3; (2016); p. 183 – 191; Khim. Geterotsikl. Soedin.; vol. 52; 3; (2016); p. 183 – 191,9;,
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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 120758-03-4 as follows. Safety of 2-Chloro-3,5-dimethoxyaniline

Example 14 Synthesis of 1-(2-chloro-3,5-dimethoxyphenyl)-2-cyclohexyl-6-cyclopentyl-3-methyl-4(1H)-pyridinone (Compound 81) In 150 ml of chlorobenzene were dissolved 4.5 g of 1-cyclohexyl-5-cyclopentyl-2-methyl-1,3,5-pentanetrione and 6.0 g of 2-chloro-3,5-dimethoxyaniline. To the mixture was added 2.0 g of titanium tetrachloride, followed by refluxing for 4 hours. The chlorobenzene of the reaction mixture was distilled off and the residue was extracted with 150 ml of chloroform. The organic layer was washed first with 100 ml of 10% hydrochloric acid and then with 100 ml of a 10% aqueous solution of sodium hydroxide. After washing the organic layer with water, it was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by column chromatography on silica gel (eluent: chloroform). The resulting crystals were recrystallized from ethyl acetate, affording 0.6 g of 1-(2-chloro-3,5-dimethoxyphenyl)-2-cyclohexyl-6-cyclopentyl-3-methyl-4(1H)-pyridinone having a melting point of 230-231 C.

According to the analysis of related databases, 120758-03-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY Co., Ltd.; EP304057; (1989); A2;,
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Synthetic Route of 54730-35-7,Some common heterocyclic compound, 54730-35-7, name is 3,5-Dichloro-4-methylaniline, molecular formula is C7H7Cl2N, 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 3,5-dichloro-4-methylaniline (0.9 mmol, 157.5 mg) in dimethyl sulfoxide (3.0 mL) is added carbodiimidazole (1.1 mmol, 178.4 mg) and stirred at room temperature for 2 hours. did.Then, 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (1.0 mmol, 319.0 mg) and triethylamino(1.0 mL) was added and stirred at room temperature for 24 hours. After heating under reduced pressure and distilling off the solvent, the resulting solid was dissolved in ethyl acetate (300 mL) and extracted three times with a saturated aqueous ammonium chloride solution (100 mL).The organic layers are combined and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure.It was. The resulting solid was washed with toluene and ethyl acetate, dissolved in methanol, and subjected to silica gel column chromatography (ethyl acetate: methanol = 1: 1) to give UA-44 (12.0 mg, yield 3%). Was obtained as a white solid.

The synthetic route of 54730-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tohoku University; Uozumi, Nobuyuki; Arisawa, Mieko; Suzuki, Futoshi; Endo, Akira; Hamamoto, Susumu; Ikenokami, Yoshiaki; (20 pag.)JP2019/137678; (2019); A;,
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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. 10541-69-2, name is (2,5-Dichlorophenyl)methanamine, A new synthetic method of this compound is introduced below., Quality Control of (2,5-Dichlorophenyl)methanamine

In a 20 mL scintillation vial, 4-amino-5-cyano-6-ethoxy-pyrindine-2-carboxylic acid (19 mg, 0.09 mmol) was dissolved in DMA (0.7 mL). Then TBTU (30 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added, followed by the addition of 2,5-dichlorobenzylamine (18 mg, 0.11 mmol, 1.2 eq.) in DMA (0.6 mL). Then TEA (9.37 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added. The mixture was shaken at room temperature for 24 hours. The crude mixture was purified using reverse phase HPLC (TFA). 1H NMR (500 MHz, DMSO-D6/D2O) ? ppm 1.24 (t, 3H) 4.03-4.86 (m, 4H) 5.88-7.87 (m, 4H). MS (ESI) positive ion 365 (M+H)+; negative ion 363(M?H)?.

The synthetic route of 10541-69-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Gang; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Liu, Mei; US2006/173050; (2006); A1;,
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Synthetic Route of 1009102-44-6,Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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 2:To a solution of methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)- 1 ,3,5-triazin-2- ylamino)benzoate (870 mg, 2.4 mmol) from Step 1 in THF (10 mL) was added l-(4- chlorophenyl)cyclopropanamine, HC1 (500 mg, 2,450 mmol) and Hunig’sBase (1.677 mL, 9.60 mmol). The resulting mixture was stiiTed for 16 h. The precipitate was filtrated through a plug washing with THF to give acrude product that was purified by Biotage eluting with 4/1-hexane/ethyl acetate to give 1.1 g of the desired product as a solid.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SUN, Li-Qiang; MULL, Eric; ZHAO, Qian; WANG, Tao; ZHANG, Zhongxing; SCOLA, Paul Michael; WO2012/24373; (2012); 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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, A new synthetic method of this compound is introduced below., Recommanded Product: 90390-33-3

159 mg of 3-chloro-5-fluorobenzylamine (1 mmol) was weighed into a dry 50 mL eggplant-shaped reaction flask, and 15 mL of dichloromethane was added.The mixture was stirred until the substrate was completely dissolved. After adding 200 muL of triethylamine, a solution of 194 mg of octanoyl chloride (1.2 mmol in a suitable amount of dry dichloromethane) was slowly added dropwise under an ice bath at 0 to 5 C.After the completion of the dropwise addition, the TLC tracking and monitoring were carried out at room temperature, and when the raw materials disappeared, 20 mL of saturated sodium hydrogencarbonate was sequentially used.The water and the saturated aqueous NaCl solution were each washed three times and dried over anhydrous sodium sulfate.After vacuum distillation under reduced pressure, silica gel column chromatography was used to give N-(3-chloro-5-fluorobenzyl)octanamide.

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; Shanghai Shidande Biological Co., Ltd.; Shanghai Shidande Criterion Technology Services Co., Ltd.; Qian Yong; Xin Zhenqiang; Shu Yaping; Zhang Tianyong; Xie Tianpei; (11 pag.)CN108503559; (2018); A;,
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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 81067-41-6 as follows. HPLC of Formula: C6H2Br2Cl2

Insert the 1,3-dibromo-2,5-dichlorobenzene (3.0g, 0.010mol) in pyridin-3-ylboronic acid (2.9g, 0.024mol) by synthesis by the same method used in Preparation Example 1-7 to give the intermediate 20-1> 2.1g (70% yield).

According to the analysis of related databases, 81067-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PNH TECH; HYUN, SEO YONG; JUNG, SUNG OUK; KIM, IK HWAN; (101 pag.)KR2016/40826; (2016); A;,
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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 25186-47-4 as follows. Quality Control of 3,5-Dichlorotoluene

(1) device: Referring to Figure 2 to determine the connection of the tubular reactor, the pipeline type is:(3a + 3d) DC-channel+ enhanced hybrid round cake rectangular flat pipe,Pipe diameter and volume based on the flow rate and reaction to determine the residence time,Heat transfer medium for thermal oil.(2) 6.06 g of cobalt acetate and 6.06 g of sodium molybdate were dissolved respectively200ml3,5 – dichloro toluene and200ml acetic acid to form a mixed solution,In this case, n (cobalt acetate): n (3,5-dichlorotoluene) = 0.015: 1,6.06 g of sodium bromide was dissolved in 20% H2O2 to form a H2O2-acetic acid solution, where n (sodium bromide): n (3,5-dichlorotoluene) = 0.015: 1,3,5-dichlorotoluene-acetic acid Solution and andH2O2-acetic acid solution respectively to 8.33ml / min andThe flow rate of 16.67 ml / min was injected into the tubular reactor which was continuously heat-exchanging by the constant current pump, at this time, n (H2O2): n (3,5-dichlorotoluene) = 2:Using the microchannel reactor of Figure 2,The reaction temperature was controlled at 105 C and the residence time was 600 s.The outlet was cooled at 0 C and the reaction quenched with dichloromethane.After GC analysis, 3,5-dichlorotoluene conversion rate of 60.8%The yield of 3,5-dichlorobenzaldehyde was 39.2%.

According to the analysis of related databases, 25186-47-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changzhou University; Yan Shenghu; Jiang Xin; Zhang Yue; Liu Jianwu; Shen Jiefa; Ma Xiaoming; Chen Daixiang; Gu Shunlin; Ni Fengchao; Li Yanfei; Wang Qiuhong; Chen Mingzhu; Wei Jin; Wu Fei; Zhang Yongchao; (9 pag.)CN106588606; (2017); A;,
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Electric Literature of 467435-07-0,Some common heterocyclic compound, 467435-07-0, name is 4-Bromo-2-chlorobenzotrifluoride, molecular formula is C7H3BrClF3, 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.

Into a glass reaction vessel equipped with a stirrer and having a capacity of 250 mL,7.2 g (68.0 mmol) of sodium carbonate,2.6 g (20.4 mmol) of 2-thiopheneboronic acid,4-Bromo-2-chlorobenzotrifluoride 2.5 mL(17.0 mmol), dehydrated toluene 102 mL, dehydrated ethanol 51 mL,And 2.0 g (1.7 mmol) of tetrakistriphenylphosphine palladium,And the mixture was reacted at 80 C. for 16 hours.Water was added to the reaction product, and the mixture was extracted with methylene chloride.After drying with magnesium sulfate and distilling off the solvent under reduced pressure, purification by silica gel column chromatography (hexane) gave 4.4 g of compound (C11-c) as a white solid.

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

Reference:
Patent; Ube Industries Ltd; Tanaka, Yasuhiro; Homma, Takashi; (66 pag.)JP2018/168138; (2018); A;,
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Synthetic Route of 622-98-0, These common heterocyclic compound, 622-98-0, name is 1-Chloro-4-ethylbenzene, 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.

2,5-Dichloro-2,5-dimethylhexane (compound 2) was synthesized using a known procedure set forth in Bruson H et al., J Am Chem Soc, 62:36 (1940), whereby 50 g of 2,5-dimethylhexane-2,5-diol (compound 1 ) and 1 L of concentrated hydrochloric acid was used. Yield was measured quantitatively. Properties of compound 2 matched that reported in Bruson et al.

Statistics shows that 1-Chloro-4-ethylbenzene is playing an increasingly important role. we look forward to future research findings about 622-98-0.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; WO2007/5568; (2007); A1;,
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