Author: Jessica.F

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. 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H8Br2O

In a 100 ml two-necked flask, 40 ml of DMF was added,4- (2-bromoethoxy) -bromobenzene (9.48 g, 47 mmol)Potassium phthalimide (10.47 g, 56 mmol) was reacted at 90 C for 2 h.After the reaction, DMF was removed by steaming and then extracted three times with chloroform to combine the organic phase,Add the appropriate amount of anhydrous MgSO4, standing for half an hour. The MgSO4 was removed by filtration,The chloroform was removed by rotary distillation and purified by column chromatography (dichloromethane as eluent) to give a white solid,Yield 85%.

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; Nanjing Tech University; Gao Deqing; Pan Zhenhuan; Tong Tong; Li Bobo; Liu Minglun; Huang Wei; (9 pag.)CN106518691; (2017); A;,
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Application of 1535-75-7, 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 1535-75-7 as follows.

General procedure: To a mixture of chloral hydrate (19.9 g, 120 mmol) in water (400 mL) was added Na2SO4(142 g, 1 mol) in portions at 40 C. After becoming homogenous and clear, the mixture was cooled to room temperature. 1 (100 mmol) and concentrated HCl (9 mL) were then added to the resulting solution, followed by a mixture of hydroxylamine hydrochloride (20.9 g, 300 mmol) in water. The solution was heated at reflux for 8 h and then cooled to room temperature. The precipitate was collected and dissolved in a 10 % aqueous NaOH solution. The resulting mixture was filtered through a pad of Celite. The filtrate was acidified to pH = 3 with 6 N HCl. The precipitate was filtered and dried to give the desired product 2.

According to the analysis of related databases, 1535-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Chang-Chun; Wang, Bao-Lei; Liu, Jing-Bo; Wei, Wei; Li, Yu-Xin; Liu, Yang; Chen, Ming-Gui; Xiong, Li-Xia; Yang, Na; Li, Zheng-Ming; Chinese Chemical Letters; vol. 28; 6; (2017); p. 1248 – 1251;,
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Application of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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) (3-Trifluoromethoxy-phenylamino)-acetonitrile; A mixture of 3-(trifluoromethoxy)aniline (1.00 g, 5.64 mmol), bromoacetonitrile (745 mg, 6.21 mmol), sodium iodide (1.86 g, 12.4 mmol), and sodium carbonate (858 mg, 6.21 mmol) in CH3CN (15 mL) was heated at reflux for 18 h, then partitioned between water and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc gradient) afforded the title compound (904 mg, 74percent). Brown liquid, MS: 215.2 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Trifluoromethoxyaniline, its application will become more common.

Reference:
Patent; Adam, Jean-Michel; Aebi, Johannes; Binggeli, Alfred; Green, Luke; Hartmann, Guido; Maerki, Hans P.; Mattei, Patrizio; Ricklin, Fabienne; Roche, Olivier; US2010/22518; (2010); A1;,
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Reference of 74137-36-3, 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 74137-36-3 as follows.

[0353] A 1.6 M solution of n-butyllithium in hexane (5.65 niL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5°C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL , 4.52 mmol) was added slowly with the temperature held below 0°C over a period of 15 min. Stirring was continued for 45 min at -5°C, followed by drop wise addition of a solution of l,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 00C. The mixture was stirred for 45 min at -5°C. A solution of iodine chloride (1.83 g, 11.3 mmol) in methylene chloride (20 mL) was added in the described manner and stirring continued for additional 20 min at -5°C. The mixture was warmed to room temperature. Water (50 mL) and toluene (50 mL) were added and the layers were separated. The organic layer was washed with a saturated aqueous solution OfNa2S2O3 (2 x 30 mL), water and brine (30 mL). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (100 g, AcOEt/heptane 1:9). l-Bromo-3-iodo-5- methoxy-benzene (2.12 g, 60 percent) was obtained as a yellow oil, which crystallized quickly upon standing.

According to the analysis of related databases, 74137-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 20781-20-8

A mixture of 3-hydroxyphthalic anhydride (1.24 g, 7.6 mmol), 2,4-dimethoxybenzylamine (1.14 mL, 7.6 mmol) and acetic acid (5 mL) was heated at 80C for 24 hours. The mixture was allowed to cool and diluted with water (20 mL). The white solid was collected by filtration, washed well with water and dried to give the title compound (1.73 g, 73%). 1H NMR (DMSOd6) 11.00 (1 H, s), 7.62 (1H, dd), 7.29 (1 H, d), 7.21 (1 H, d), 6.90 (1H, d), 6.56 (1 H, d), 6.43 (1 H, dd), 4.59 (2H, s), 3.79 (3H, s), 3.72 (3H, s). MS: [M-H+] 314.

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); 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 366-99-4 as follows. SDS of cas: 366-99-4

Example 18; Synthesis of (4-Chloro-6-cyclohexylmethoxy-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl)-amine (114); To a sample of 113 (1.011 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solution of 3-fluoro-p-anisidine (0.541 g, 3.8 mmol) in acetone (10 mL) followed by addition of NaOH (1.52 mL, 2.5 N, 3.8 mmol) and water (3 mL). The reaction mixture was allowed to stir at reflux for about 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (silica gel, 70:30 hexanes:ethyl acetate) yielded light yellow solid compound 114 (0.581 g, 42percent), mp 98° C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.36; MS (ESI): m/z 369 (39.1), 368 (22.1), 367 (M+H, 100), 273 (3.2), 271 (10.7).; Example 19; 6-Cyclohexylmethoxy-N,N’-bis-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4-diamine; Compound 115 was obtained as a by-product (0.159 g) via column chromatography (silica gel, 70:30 hexanes:ethyl acetate), mp 181° C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.17; MS (ESI): m/z 472 (M+H, 100), 261 (1.5).

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); A1;,
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Synthetic Route of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, 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: To a stirred solution of the respective N-carbamate-protected aminovicinal diol 4 (0.50 mmol, 1 equiv) in CH2Cl2 (10 mL, 0.05 M) were added BF3·OEt2 (50 muL, 0.050 mmol, 0.1 equiv, 1.0 M solution in CH2Cl2) and trimethyl orthobenzoate (0.13 mL, 0.75 mmol, 1.5 equiv) at r.t. The resulting mixture was refluxed or stirred at r.t. under N2 until TLC showed complete conversion of the substrate. The reaction was quenched with sat. aq NaHCO3 and extracted with EtOAc (2 ×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane/EtOAc) to give the desired product 5.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Heemin; Kwon, Yongseok; Shin, Jae Eui; Kim, Woo-Jung; Hwang, Soonho; Lee, Seokwoo; Kim, Sanghee; Synthesis; vol. 49; 12; (2017); p. 2761 – 2767;,
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Reference of 33311-29-4, A common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, 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.

To a solution of compound 27-1 in DMF (50 mL) was added dropwise DIPEA (4.55 g, 35.23 mmol) and compound 27-1-1 (5 g, 30.2 mmol) under nitrogen atmosphere at 0 C., and the reaction solution was reacted at 0 C. for 0.5 h, followed by warmed to r.t. and reacted for another 1 h. The resulting reaction solution was diluted with EtOAc (50 mL) and washed with brine (30 mL×3). The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to give a residue was purified by column chromatography (3% to 8% of PE/EtOAc) to afford the title compound (360 mg, 26.3%) as white solid.

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; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
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Reference of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

1-(2-Bromoethoxy)-4-fluorobenzene (25.5 g (0.116 mol)) and N-ethylcyclohexylamine hydrochloride (28.5 g (0.174 mol)) were dissolved in ethanol (400 mL), and then potassium carbonate (48.7 g (0.35 mol)) and sodium iodide (44.1 g (0.232 mol)) were added to the solution. The mixture was stirred for 48 hours under heating at reflux, and the reaction mixture was returned to room temperature. The insoluble fraction was removed by filtration and the solvent was distilled away under reduced pressure. The residue was purified by a silica gel chromatography (petroleum ether: ethyl acetate = 6 : 1) and hydrogen chloride gas was passed into the resulting oil to precipitate a crystal, which was collected by filtration to obtain the target N-ethyl-N-[2-(4-fluorophenoxy)ethyl]cyclohexylamine hydrochloride (5.3 g, 17.6 mmol, yield 24%).

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

Reference:
Patent; M’s Science Corporation; EP2357165; (2011); A1;,
Ether – Wikipedia,
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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. 2525-16-8, name is 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine

I. 3-Methyl-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one 25 g 2-bromo-4-methylbenzoic acid was treated with 150 mL of 28% aqueous ammonia, 50 g gaseous ammonia, 1 g CuSO4 at 140 C. for 12 hours in an autoclave, then concentrated in vacuo, dissolved in a minimal amount of water, pH adjusted to 6 with 4N HCl. The precipitate was filtered, washed with ice cold water, and dried at 60 C. The residue was extracted with THF and concentrated in vacuo, giving a light brown crystalline solid. Yield of combined material: 14 g 4-methylanthranilic acid. 6.4 g of this acid was suspended with stirring in 100 mL toluene. 11 mL 1-Aza-2-methoxy-1-cycloheptene (1) (Aldrich) were added and the mixture was refluxed under a Dean-Stark trap for 12 hours. Then the toluene was removed by distillation in vacuo, followed by removal of excess (1) in vacuo (11 mm Hg) at 140 C. The dark brown residue crystallized. It was purified by column chromatography (6:1 chloroformethyl acetate) followed by recrystallization from hexane-ethyl acetate to give 7.1 g of pure 3-methyl-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one as white, shiny crystals.

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; Warner-Lambert Company; US5486512; (1996); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem