Category: ethers-buliding-blocks

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H11BrO2

A suspension of 5-bromo-4-fluoropyridin-2-amine (1 g, 5.24 mmol) inisopropanol (10 mL) was treated with 1-bromo-2,2-dimethoxypropane (1.16 g, 6.28mmol). The resulting mixture was heated at 80C for 21 h, then cooled to room temperature and concentrated under vacuum at 40C. The residue was treated with ethyl acetate (15 mL) and water (15 mL) and the phases were separated. The aqueous phase was basified with aqueous NaOH solution (32% w/w) to pH 8, then extracted with ethylacetate (10 mL, then 15 mL). The organic phases were pooled and concentrated under vaccuum at 40C to give the title compound (0.93 g, 78%) as a beige solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 126-38-5.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki Peter; BENTLEY, Jonathan Mark; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; CHOVATIA, Praful Tulshi; DEBOVES, Herve Jean Claude; JOHNSTONE, Craig; JONES, Elizabeth Pearl; KROEPLIEN, Boris; LECOMTE, Fabien Claude; MADDEN, James; MILLER, Craig Adrian; PORTER, John Robert; SELBY, Matthew Duncan; SHAW, Michael Alan; VAIDYA, Darshan Gunvant; YULE, Ian Andrew; WO2015/86506; (2015); A1;,
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Electric Literature of 366-99-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

Cyanuric chloride (1.84 g, 10 mmol) in CH3CN (20 mL) was cooled to about -10¡ã C. was added 3-fluoro-p-anisidine (1.41 g, 10 mmol) followed by DIEA (1.8 mL, 10 mmol). The reaction was stirred for about 45 min then at room temperature for about 45 min under an N2 atmosphere. Cycloheptylamine (1.26 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the reaction was stirred at room temperature overnight. N,N-dimethylethylenediamine (1.1 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the mixture was heated at reflux under N2 overnight. The reaction was diluted with ethyl acetate, washed with brine, and dried over anhydrous K2CO3. The material (1.178 g) was purified by silica gel column chromatography to afford a solid 150 (1.178 g, 28percent), mp 73-76¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 10.8 min, 95.1percent purity; MS (ESI): m/z 418 (M+H, 100), 373 (11.9), 322 (7.8), 277 (6.8), 162 (3.6).

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-4-methoxyaniline. I believe this compound will play a more active role in future production and life.

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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Application of 2734-70-5, The chemical industry reduces the impact on the environment during synthesis 2734-70-5, name is 2,6-Dimethoxyaniline, I believe this compound will play a more active role in future production and life.

To a solution of 2,6-dimethoxyaniline (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6-lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added dropwise. The reaction mixture was then stirred for 2 h. The solvent was evaporated under reduced pressure and the material thus obtained was purified by SiC column to provide the title compound, 2-isothiocyanato-l,3-dimethoxybenzene, Example 82.0 as a white solid (1.06g, 2.80 mol, 86%). LCMS (ESI pos. ion) m/z: (M+H)+ = 196. NMR (400 MHz, CDCI3) delta 7.16 (t, J= 8.48 Hz, 1H), 6.55 (d, J = 8.48 Hz, 2H), 3.90 (m, 6H).

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, 2,6-Dimethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
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Application of 20469-61-8, A common heterocyclic compound, 20469-61-8, name is 1-Methoxy-2,3,5-trimethylbenzene, molecular formula is C10H14O, 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) Synthesis of 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride In 500 ml of methylene chloride was dissolved 4.5 g of 2,3,5-trimethylanisole and the solution was cooled to -5 C. to -10 C. A solution of 6.0 ml of chlorosulfonic acid in 400 ml of methylene chloride was added dropwise, and then the temperature was allowed to rise to room temperature. The mixture was poured into an ice–5% aqueous sodium hydrogen carbonate mixture. The methylene chloride layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off, and the residue was crystallized from n-hexane. Yield 5.0 g (67.0%). m.p. 56-58 C.

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; Takeda Chemical Industries, Ltd.; US4476051; (1984); A;,
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Application of 59557-91-4, 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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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.

4-Bromo-2-methoxyaniline (2.00 g, 9.90 mmol) were dissolved in water (10 mL) and concentrated hydrochloric acid (3 mL). The mixture was cooled in ice-salt bath, then a solution of sodium nitrite (0.69 g, 9.8 mmol) in water (4 mL) was added dropwise slowly while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 5 min. The mixture described above was added to a mixture of sodium acetate trihydrate (8.75 g, 64.3 mmol), ethyl isocyanoacetate (1.0 mL, 9.15 mmol) and MeOH/H2O (22 mL, 10/1) while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 30 min, then warmed to rt for further 3 h. After the reaction was completed, the mixture was concentrated to remove most of the solvent. The residue was filtered, and the filter cake was washed with cool water. The filter cake was dried in vacuo to give a reddish brown solid (2.65 g, 82.1%). MS (ESI, pos.ion) m/z: 327.1 (M+2)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
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Synthetic Route of 60789-54-0, A common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, molecular formula is C11H15BrO, 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 115 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.1 g) as starting compound, potassium carbonate (1.5 g) and 4-benzyloxybutyl bromide (1.0 g) were reacted and treated in the same manner as in Example 52 to give 0.32 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-benzyloxybutyl)piperidin-4-yl)methyl)benzamide. 1H-NMR (CDCl3,ppm)delta:1.40-1.81(9H,m), 2.82(2H,t), 2.98(2H,t), 3.20(2H,t), 3.44(4H,m), 3.82(3H,s), 4.45(3H,s), 5.93(2H,s), 6.48(1H,s), 7.33-7.45(5H,m), 7.66(1H,s), 8.00(1H,t)

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; YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.; EP873990; (1998); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, 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 35822-58-3, Safety of 2-Bromobenzaldehyde diethyl acetal

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

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-Bromobenzaldehyde diethyl acetal, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 50; 4; (2018); p. 416 – 423;,
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Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 suspension of the appropriate quinolonecarboxylic acid (1mmol) in 6mL of dry THF at 25C, HOBt (1.5mmol), WSC (1.5mmol) and the appropriate aminoalcohol (1.5mmol) were added sequentially. The mixture was stirred at room temperature under nitrogen, then the solvent was evaporated, water was added and the solid formed filtered. The crude product was purified by flash chromatography.

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cincinelli, Raffaella; Musso, Loana; Beretta, Giangiacomo; Dallavalle, Sabrina; Tetrahedron; vol. 70; 52; (2014); p. 9797 – 9804;,
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Electric Literature of 24599-58-4, A common heterocyclic compound, 24599-58-4, name is 2,5-Dimethoxytoluene, molecular formula is C9H12O2, 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.

In a more recent development of the invention, work toward the synthesis of oosporein has progressed via several approaches. One set of approaches to the synthesis of oosporein utilizes 2,5-dimethoxytoluene (1) (commercially available, and available in one step in high yield from the very inexpensive starting material methylhydroquinone) as the initial starting material. Proper choice of oxidant and reaction conditions allowed preparation of either biphenyl derivative (2) or diquinone (3), both in high yield and good purity (Scheme 1).

The synthetic route of 24599-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PhytoMyco Research Corporation; US2007/110726; (2007); A1;,
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Application of 10541-78-3,Some common heterocyclic compound, 10541-78-3, name is 2-Methoxy-N-methylaniline, molecular formula is C8H11NO, 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: Dichloromethane (20 mL) and phenylpropynoic acid (11 mmol) were added into a 50 mL round bottom glass flask, and then N-alkylaniline (10 mol) was added at 0 C. Thereafter, a solution of DCC (15 mol), DMAP (0.5 mmol) and dichloromethane (20 mL) was slowly added dropwise with stirring. The reaction mixture was allowed to warm to room temperature and then stirred overnight. The mixture was washed with 5 mL saturated NaCO3 solution, 5 mL saturated NaCl solution, and 5 mL water. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate as the eluent) affording the corresponding N-phenylpropynamide 1.

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

Reference:
Article; Chen, Yuan; Chen, Yu-Jue; Guan, Zhi; He, Yan-Hong; Tetrahedron; vol. 75; 51; (2019);,
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