Category: ethers-buliding-blocks

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., Computed Properties of C4H9BrO

Example 65 Preparation of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,6-diisopropyl-3-(2-ethoxyethyloxy) phenyl)acetamide: 2-Bromoethyl ethyl ether (2 ml) and potassium fluoride catalyst carried on alumina (40 wt %, 225 mg, 1.51 mmol) were added to a solution of 2-[4-[2-(benzoxazol-2ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3hydroxyphenyl)acetamide (150 mg, 0.30 mmol) in acetonitrile (3 ml) followed by stirring for 41 hours. The catalyst was filtered off and the filtrate was diluted with water and extracted with ethyl acetate. The organic layer was washed with a sodium chloride solution and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a preparative thin layer chromatography (developing solvent, chloroform:ammonia-saturated methanol=20:1) and the resulting crude crystals were recrystallized from ethyl acetate-hexane to provide 120 mg (yield 70%) of the desired compound as colorless powdery crystals. Melting point: 100-103 C. IR (KBr) cm-1: 3282, 2960, 1661, 1498, 1454. 1H-NMR (CDCl3) delta: 1.17 (6H, d, J=6.9 Hz), 1.23 (3H, t, J=7.0 Hz), 1.32 (6H, d, J=6.9 Hz), 2.62-2.79 (8H, m), 2.86 (2H, t, J=6.2 Hz), 2.93 (1H, sept, J=6.9 Hz), 3.19 (1H, sept, J=6.9 Hz), 3.21 (2H, s), 3.50 (2H, t, J=6.2 Hz), 3.59 (2H, q, J=7.0 Hz), 3.81 (2H, t, J=5.1 Hz), 4.09 (2H, t, J=5.9 Hz), 6.83 (1H, d, J=8.7 Hz), 7.09 (1H, d, J=8.7 Hz), 7.22-7.30 (2H, m), 7.43 (1H, m), 7.58 (1H, m), 8.56 (1H, br s). EIMS m/Z (relative intensity): 568 (M+), 276 (100).

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; Kowa Company, Ltd.; US2004/38987; (2004); A1;,
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Related Products of 102-52-3, These common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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 6Preparation of Bromomalonaldehyde (9); De-ionized water (2.080 L) was added to a 12-L, four-neck flask under a nitrogen atmosphere and equipped with a thermocouple. Concentrated HCl (88 mL) was added to the water. Malonaldehyde bis-dimethylacetal (2006 mL, 2.0 kilogram (kg), 12.18 moles) was added dropwise over a period of 45 to 60 minutes while the temperature was maintained between 5 C. and 25 C. Bromine (1.912 g, 619 mL; 12 moles; 1 equivalent.) was added dropwise over 1 hour, while the temperature was maintained between 5 C. and 20 C. The reaction was monitored by HPLC for completion. After completion of the reaction (2 to 4 hours), the reaction mixture was concentrated on a rotary evaporator at 45 C. and 100 torr. The resultant mixture was stirred for 1 hour at room temperature, filtered, and washed with cold water (2¡Á1.0 liter). The isolated solids were dried in a forced-air dryer for 2 days. The weight of the product (9) obtained was 1.008 kg, with a 430 g second crop from the filtrate, giving a combined 76% yield. The second crop of crystals was obtained by concentrating the mother liquor to half its original volume and filtering off the resulting crystals. Mass spectrometry (M+H): 150.97 and 151.96 amu.

Statistics shows that 1,1,3,3-Tetramethoxypropane is playing an increasingly important role. we look forward to future research findings about 102-52-3.

Reference:
Patent; Wyeth; US2009/18332; (2009); 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. 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, A new synthetic method of this compound is introduced below., Product Details of 929-75-9

Step 4. Synthesis of 11-t-butoxycarbonylamino-3,6,9-trioxaundecylamine 3 g of 1,11-diamino-3,6,9-trioxaundecane obtained in the above step 3 was dissolved in 5 mL of tetrahydrofuran, and then a solution of 1.14 of di-t-butyl dicarbonate in 5 mL of tetrahydrofuran was added dropwise under ice cooling. Then, the solution was stirred overnight at room temperature, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and then the solution was washed with saturated saline. The organic layer was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography to obtain 1 g of the objective compound.

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; Nippon Shinyaku Co., Ltd.; EP1783137; (2007); 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;,
Ether – Wikipedia,
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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;,
Ether – Wikipedia,
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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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