Author: Jessica.F

Electric Literature of 145903-31-7,Some common heterocyclic compound, 145903-31-7, name is 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine, molecular formula is C10H13NOS, 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.

Synthesis of S19 (Scheme 6): To a stirred solution of S26 (20 mg, 0.1 mmol) and triethylamine (30 mg, 0.3 mmol) in CH2Cl2 (5 ml) is added 1,4-butyldiacid chloride (8 mg, 0.05 mmol) at 0 C. The resulting mixture is stirred at 0 C. for one hour and at room temperature overnight. The organic phase is washed with saturated sodium bicarbonate and 1N HCl and water. After removal of solvent, product S19 is purified by column chromatography (oil, 19 mg, 80% yield). Similarly S22 is prepared from 2,6 pyridyl dicarboxylic acid dichloride.

The synthetic route of 145903-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; US2007/49572; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2-ethoxyethane

0.24 g (10 mmol) of sodium hydride and 15 ml of N, N-dimethylformamide were added to a 50 ml round bottom flask at room temperatureStir for 10 minutes then add 2.5 g (10 mmol) of compound 2 and 10 mmol2-bromoethylether and trace detection by TLC to the end of the reaction. The reaction mixture was then poured into 500 ml of ice water and extracted three times with 100 ml of ethyl acetate. The organic phases were combined and the solvent was evaporated to dryness. The resulting residue was subjected to silica gel column chromatography Purification (V dichloromethane: V methanol = 100: 1) gave compound 3 (2.4 g, 76% yield).

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; Guangxi Normal University; Chen Zhenfeng; Liang Hong; Liu Yancheng; Lu Xing; Li Liangping; (13 pag.)CN106632414; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 645-36-3, name is 2,2-Diethoxyethanamine, belongs to ethers-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 645-36-3, Application In Synthesis of 2,2-Diethoxyethanamine

A solution of 1-NAPHTHALENYLTHIOISOCYANATE (893 mg, 4.82 MMOL) and 2- AMINOACETALDEHYDE DIETHYL ACETAL (0.70 mL, 4.85 MMOL) IN TOLUENE (10 mL) was stirred at room temperature for 1 h. Aqueous 12 N HCI solution (0.2 mL) was added and the mixture was heated at 110 C for 3 h and then stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was triturated with hot EtOAc to give the title compound (608 mg, 56% yield).

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, 2,2-Diethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2004/50643; (2004); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 32338-02-6, name is 2-Bromo-4-methoxyaniline, A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 °C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

The synthetic route of 32338-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 22236-08-4, The chemical industry reduces the impact on the environment during synthesis 22236-08-4, name is 3-(Difluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

Method G6: N-(3-(difluoromethoxy)phenyl)-6-nitro-2-(pyrazin-2-yl)quinazolin-4-amine (vi-s):_A mixture of 4-chloro-6-nitro-2-(pyrazin-2-yl)quinazoline (1.00 g, crude, 3.7 mmol, 1.0 eq.), 3-(difluoromethoxy)benzenamine (600 mg, 3.7 mmol, 1.0 eq.) and Et3N (1.00 g, 10 mmol, 3.0 eq) in THF (80 mL) was stirred at 75 C. for 18 h. After cooling, the volatiles were removed in vacuo and the residue was washed with H2O (100 mL×2). The solid was dried in vacuo to afford 1.40 g of N-(3-(difluoromethoxy)phenyl)-6-nitro-2-(pyrazin-2-yl)quinazolin-4-amine as a black solid (90.2% of two steps). LCMS m/z=411.0 (M+1) (Method A) (retention time=1.61 min)

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-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Suzuki, Masaki; Kondo, Kazumi; Kurimura, Muneaki; Valluru, Krishna Reddy; Takahashi, Akira; Kuroda, Takeshi; Takahashi, Haruka; Fukushima, Tae; Miyamura, Shin; Ghosh, Indranath; Dogra, Abhishek; Harriman, Geraldine; Elder, Amy; Shimizu, Satoshi; Hodgetts, Kevin J.; Newcom, Jason S.; US2015/307477; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 1535-75-7, A common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, 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: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 36865-41-5, The chemical industry reduces the impact on the environment during synthesis 36865-41-5, name is 1-Bromo-3-methoxypropane, I believe this compound will play a more active role in future production and life.

To a solution of Intermediate 7 (4.02 g, 20.7 minol) in DMF (50 mL) sodium hydride 60% in mineral oil (992 mg, 22.7 minol) was added carefully at 0 00. The ice bath was removed and the mixture was stirred for 30 min at room temperature. The resulting suspension was cooled at 00 and 1-bromo-3-methoxypropane (2.3 mL, 20.7 minol) was added. The reaction mixture wasstirred over night at room temperature. The mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washes with brine, dried over Na2SO4 and evaporated. The crude material was purified by flash-chromatography on silica gel to yield the desired product (4.6 g, 85%).1H-NMR (400MHz, DMSO-d6): oe [ppm]= 1.02 (d, 3H), 1.80 (quin, 2H), 2.24 (dd, IH), 2.62 (dd, IH), 3.21 (s, 3H), 3.24-3.36 (m, 3H), 3.57-3.68 (m, IH), 3.82-3.93 (m, IH), 5.55 (s, 2H), 6.53- 6.61 (m, 2H), 7.42 – 7.56 (m, 2H).UPLO (Method 2): R = 0.79; MS (ESIpos): mz [M÷H] 276.

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, 1-Bromo-3-methoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; QUANZ-SCHOEFFEL, Maria; MUeLLER, Thomas; GUeNTHER, Judith; BOeHNKE, Niels; GRIEBENOW, Nils; BARAK, Naomi; BOeMER, Ulf; NEUHAUS, Roland; OSMERS, Maren; KOPITZ, Charlotte Christine; KAULFUSS, Stefan; REHWINKEL, Hartmut; WEISKE, Joerg; BADER, Benjamin; CHRISTIAN, Sven; HILLIG, Roman; (426 pag.)WO2018/86703; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 22236-10-8, These common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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-Butyl-4-{[4-(difluoromethoxy)phenyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide; 2-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.63g, 2.1mmol) and 4-(difluoromethoxy)-aniline (0.67g, 4.2mmol) were mixed in MeCN (4mL, dry). The mixture was put in a microwave reactor at 1600C for 1 hour, then for additional 1 hour then for 1 hour more. It was evaporated to dryness. The residue was purified by column chromatography (ISOLUTE SI, 50g/150mL), eluting with dichloromethane/heptane (50:50, then 75:25), to give the title compound (0.688g, 78%) as a yellow solid;

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/73364; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, 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. Computed Properties of C7H7BrO

The advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole. the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-^-Bu)PdCl2 (1 mol%) in DME gave a complicated mixture of products was obtained (Table 10, Entry 1). When conducted in the presence of zinc chloride and TMEDA, however, the reaction could successfully gave the desired monoarylation product, 3-methoxyaniline, although at high concentrationsN,N-dimethyl-3-methoxyaniline was formed in a significant amount as a by- product (Table 10, Entries 3 and 4). Under optimized conditions (Table 10, Entries 8 and 9), 3-methoxyaniline was formed selectively in good yield.

The synthetic route of 1-Bromo-3-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; WO2007/109365; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-Bromo-2-methoxyaniline, belongs to ethers-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 6358-77-6, HPLC of Formula: C7H8BrNO

To a stirred 100 mL RBF was added 5-bromo-2-methoxyaniline (7 g, 34.6 mmol) and DIEA (12.05 mL, 69.3 mmol) in DCM (100 mL). At 0 C, furan-2-carbonyl chloride (3.41 mL, 34.6 mmol) was added dropwise. The reaction mixture was stirred at 0 C and allowed to warm to RT overnight. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo. The sample was preloaded on silica and purified with flash chromatography on a CombiFlash silica gel column (80 g, Teledyne Isco, gradient 20% EtOAc in hexanes) to give Example 209.1. LCMS (ESI) m/z= 297 [M+Hf?.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem