Month: December 2020

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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Safety of 1-(3-Methoxyphenyl)-N-methylmethanamine

Step B: Ethyl acrylate (33.0 mL, 298 mmol) was added to a stirred mixture of benzylamine (15.0 g, 99.2 mmol) from Step A above and acetic acid (3 mL) at 0 C. The mixture was heated at 80 C. for 4 hours and allowed to cool to room temperature before diluting with dichloromethane (300 mL). The reaction mixture was washed with saturated NaHCO3, dried over Na2SO4 and concentrated in vacuo. The residue was treated with toluene and the resulting solution concentrated in vacuo in order to remove residual ethyl acrylate, affording the ester (25.0 g, 100%) as a colorless oil: 1H NMR (500 MHz, CDCl3) delta 7.22 (t, J=8.0 Hz, 1H), 6.89-6.86 (m, 2H), 6.78 (dd, J=8.2, 2.5 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 3.80 (s, 3H), 3.48 (s, 2H), 2.74 (t, J=7.2 Hz, 2H), 2.51 (t, J=7.2 Hz, 2H), 2.21 (s, 3H), 1.25 (t, J=7.1 Hz, 3H).

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; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H13NO2

c) 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylidene imidazolidin-4-yl]-N-[4-(2-methoxyethoxy)phenyl]acetamide (example 53) [0196] HOBt (84 mg; 0.55 mmol; 1.5 eq), DIPEA (323 muL; 1.85 mmol; 5 eq) and 4-(2-methoxyethoxy)aniline (81 mg; 0.48 mmol; 1.3 eq) were added to a solution of 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]acetic acid (1-21) (150 mg; 0.37 mmol; 1 eq) in dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 2 days. Ethyl acetate (10 mL) and water (5 mL) were added and the layers were separated. The organic layer was washed with saturated ammonium chloride (10 mL), water (10 mL) and sodium chloride (2 x 15 mL), dried over sodium sulfate, filtered and concentrated to dryness. The crude was triturated in ethyl acetate, washed with petroleum ether, and concentrated to dryness. The residue was taken up in ethyl acetate/cyclohexane (200 muL) until precipitation, filtration. The title compound, 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-[4-(2-methoxyethoxy)phenyl]acetamide, was obtained in 25 % yield (50 mg) as a yellow solid. 1H-NMR (Acetone-d6): delta (ppm) 2.85 (m, 1H), 3.17 (m, 2H), 3.36 (s, 3H), 3.40 (m, 1H), 3.65 (m, 2H), 3.68 (s, 3H), 3.70 (m, 1H), 4.09 (m, 2H), 4.31 (m, 1H), 4.63 (m, 1H), 6.87 (m, 4H), 7.25 (m, 4H), 7.49 (m, 4H), 9.34 (s, 1H); MS (ESI+): m/z = 551.9 [M+H]+.

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 33311-29-4.

Reference:
Patent; Vivalis; Guedat, Philippe; Berecibar, Amaya; Ciapetti, Paola; Venkata Pithani ,Subhash; Trouche, Nathalie; EP2664616; (2013); A1;,
Ether – Wikipedia,
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Reference of 1017779-69-9, A common heterocyclic compound, 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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.

A solution of 3-fluoro-4-(trifluoromethoxy)aniline [CAS 101 7779-69-9] (32.0 g, 164 mmol) in CH3CN (600 mL) was stirred on an ice-bath. N-iodo-succinimide (40.59 g, 180.4 mmol) was added and the reaction mixture was allowed to slowly reachroom temperature while stirring overnight. The solvent was concentrated under reduced pressure. Water was added and the product was extracted with EtOAc (2x 300 mL). The combined organic layers were washed with and an aqueous solution of Na2S2O3 (500 mL), brine (500 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by columnchromatography on silica gel (eluent: petroleum ether/EtOAc gradient 50/1 to30/1). The desired fractions were combined and evaporated under reduced pressure to provide 5-fluoro-2-iodo-4-(trifluoromethoxy)aniline 7a (45 g).

The synthetic route of 1017779-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (91 pag.)WO2017/167950; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7FO

Step 1: Preparation of 1-(3-fluoro-4-methoxyphenyl)-2-phenyl-ethan-1-one. A suspension of aluminum chloride (9.4 g, 70.5 mmol) in a solution of 2-fluoroanisole (6.6 mL, 58.8 mmol) and anhydrous chloroform (200 mL) was cooled to 0 C. under a blanket of dry nitrogen. A solution of phenylacetyl chloride (8.6 mL, 64.7 mmol) in anhydrous chloroform (50 mL) was added to the vigorously stirred suspension over 20 minutes keeping the reaction temperature <5 C. The yellowish solution was stirred at 0 C. for 1 hour, poured into ice (200 mL) and stirred without temperature control for 16 hours. The layers were separated, and the aqueous layer was extracted with dichloromethane (2*100 mL). The combined organic solution was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting solid was recrystallized from boiling hexane to yield, upon filtration and drying, 1-(3-fluoro-4 methoxyphenyl)-2-phenyl-ethan-1-one (12.9 g, 90%) as white crystals: 1 H NMR (CDCl3 /300 MHz) delta 7.82-7.72 (m, 2H), 7.35-7.24 (m, 5H), 6.98 (dd, J=8.46, 8.26 Hz, 1H), 4.22 (s, 2H), 3.94 (s, 3H). 19 F NMR (CDCl3 /282.2 MHz) -134.875 (m). According to the analysis of related databases, 321-28-8, the application of this compound in the production field has become more and more popular. Reference:
Patent; G. D. Searle & Co.; US5859257; (1999); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H8F3NO

d) Preparation of Intermediate 4 3-Methoxy-5-(trifluoromethyl)benzenamine (20 g, 104.6 mmol) was added portion-wise to a cooled solution of NaNO2 (7.392 g, 107.1 mmol) in H2SO4 (74 ml) and CH3COOH (88 ml). This mixture was added dropwise to a vigorously stirred solution of CuBr (18 g, 62.8 mmol) in 48% HBr (200 ml) at 0 C. The r.m. was stirred for 45 min at r.t. and was then poured into ice-water. This aqueous mixture was extracted with DCM. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated at low temperature. The residue was stirred in a NaHCO3 solution and extracted with DIPE. The separated organic layers was dried (MgSO4), filtered and the solvent was evaporated. Yield: 12.7 g of intermediate 4 (yield 48%).

The synthetic route of 349-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MacDonald, Gregor James; Thuring, Johannes Wilhelmus John F.; Van den Keybus, Frans Alfons Maria; Van Roosbroeck, Yves Emiel Maria; US2012/172354; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 36865-41-5, 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 36865-41-5 as follows.

5-Chloro-4-dimethoxymethyl-2-(3-methoxy-propyl)-pyridine.To a suspension of Mg (911 mg, 37.5 mmol) and iodine (one crystal) in dry THF (30 mL) was added dropwise 5% of the total amount of l-bromo-3-methoxypropane (4.59 g, 30.0 mmol). The mixture was heated to reflux with the help of a heat gun until the Grignard- formation started. The rest of the l-bromo-3-methoxypropane was added slowly, while an exothermic reaction proceeded. After the end of the addition, the reaction mixture was stirred under reflux for 20 min, and was allowed to cool to rt. This Grignard-sol. (IM in THF, 23.5 mL, 23.5 mmol) was added dropwise to a mixture of 2-bromo-5-chloro-4- dimethoxymethyl-pyridine (2.50 g, 9.38 mmol) and Ni(dppp)Cl2 (495 mg, 0.938 mmol) in THF (50 mL) at 0 0C. The reaction mixture was stirred at rt for 30 min, and was then heated to reflux for 2 h. The mixture was allowed to cool to rt, and was dissolved with EtOAc. This mixture was washed with aq. sat. NaHCO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane – > EtO Ac/heptane 1 :1) yielded the title compound (1.51 g, 62%). LC-MS: tR = 0.80 min; ES+: 260.15.

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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. category: ethers-buliding-blocks

A 250 mL round-bottomed flask was charged with 5-bromo-2-methoxy-phenol ( 1 .5 g, 76.4 mmol), l -bromo-3-methoxy-propane (12.9 g, 84 mmol), K >C( , (22 g, 2 153 mmol) and DM F (50 mL). The resultant mixture was stirred at 50 C for 3 hours, and then ethyl acetate and water was added. The organic phase was separated, and then dried over anhydrous Na?SO.and then concentrated to give 4-bromo- l -methoxy-2-(3-methoxypropoxy)benzene (23 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36865-41-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; YANG, Song; HAN, Xingchun; WANG, Zhanguo; (96 pag.)WO2015/173164; (2015); A1;,
Ether – Wikipedia,
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Synthetic Route of 39538-68-6, The chemical industry reduces the impact on the environment during synthesis 39538-68-6, name is 2-Methoxy-4-methylaniline, I believe this compound will play a more active role in future production and life.

Iron (5.35 g, 95.7 mmol) was added to a solution of 2-nitro-5-methylanisole (10, 4.00 g, 23.9 mmol) in ethanol (60 ml) and 6 M aqueous hydrochloric acid (30 ml), and the mixture was heated at reflux for 2 h. The reaction mixture was diluted with ethyl acetate and filtrated through Celite. Evaporation of the filtrate afforded crude 11. NaNO2 (2.11 g, 30.6 mmol) was added to a solution of crude 11 (2.80 g, 20.4 mmol) in THF (80 ml) and 4 M aqueous hydrochloric acid (40 ml) at 0 C. After 30 min, potassium iodide (4.80 g, 30.6 mmol) was added, and the mixture was heated at reflux for 3 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with saturated sodium thiosulfate and brine, dried with sodium sulfate, and evaporated. Purification by silica gel column chromatography (n-hexane/ether 100:1 to 98:2) gave 12 (pale yellow oil, 3.77 g, 15.2 mmol, 65% for two steps). 1H NMR (500 MHz, CDCl3) delta 7.60 (d, 1H, J=7.9 Hz), 6.63 (d, 1H, J=1.2 Hz), 6.53 (dd, 1H, J=7.9, 1.2 Hz), 3.84 (s, 3H), 2.31 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 157.84, 139.86, 138.96, 123.36, 112.07, 81.78, 56.18, 21.42; HRMS (FAB+) m/z 248.9780 [(M+H)+: calcd for C8H10OI, 248.9776].

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-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Iwashita, Masazumi; Fujii, Shinya; Ito, Shigeru; Hirano, Tomoya; Kagechika, Hiroyuki; Tetrahedron; vol. 67; 33; (2011); p. 6073 – 6082;,
Ether – Wikipedia,
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Application of 7252-83-7, 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 15-9: Preparation of 2-(4-methyl-2-nitro-phenyl)-thiazole (65).; The procedure described in Example 15-1 was followed except that 4-methyl-2-nitro- thiobenzamide (56) was used instead of 4-trifluoromethyl-2-nitro-thiobenzamide, bromoacetaldehyde-dimethylacetal was used instead of 1 -bromo-3-methyl-butan-2-one, and the reaction was acid catalyst with 5% acetic acid. This gave the title compound (66 mg, 75%). LC/MS: (Method I): tR= 0.98 min, >90%, m/z (ESI+)= 221 (MH+).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1,1-dimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14922; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 62415-74-1,Some common heterocyclic compound, 62415-74-1, name is 1,2-Dibromo-4-methoxybenzene, molecular formula is C7H6Br2O, 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 Intermediate I-1 (0258) 5.31 g (20.0 mmol) of 1,2-dibromo-4-methoxybenzene, 3.30 g (30.0 mmol) of pyrocatechol, 0.190 g (1.0 mmol) of CuI, 0.264 g (1.0 mmol) of 18-crown-6, and 8.28 g (60.0 mmol) of K2CO3 were dissolved in 150 mL of dimethylformamide (DMF), and stirred at a temperature of about 140 C. for about 24 hours. The solution was cooled to room temperature, 60 mL of water was added thereto, and an organic layer was extracted three times therefrom using 60 mL of diethyl ether. The obtained organic layer was dried using magnesium sulfate (MgSO4), and the MgSO4 was removed by filtration. A solvent was next removed therefrom by evaporation. The obtained residue was separated and purified through silica gel chromatography to produce 3.21 g of Intermediate I-1 (yield: 75%). The obtained compound was identified by liquid chromatography-mass spectrometry (LC-MS). C13H10O3: M+1 215.1

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-Dibromo-4-methoxybenzene, its application will become more common.

Reference:
Patent; SAMSUNG DISPLAY CO., LTD.; Kim, Youngkook; Jung, Hyejin; Han, Sanghyun; Hwang, Seokhwan; (115 pag.)US2017/77419; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem