Author: Jessica.F

Application of 74654-07-2, 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. 74654-07-2 name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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.

Cyanomethanesulfonyl chloride was found to be relatively unstable in air and was reacted immediately (3.44 mmol) with previously synthesized 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (A2, 5.41 mmol) in DCM (10 mL). HOBt (5.43 mmol) was added dropwise to the reaction mixture once cooled to 0 C., followed by EDC (5.43 mmol). The reaction was then let stir for 6 hours at 0 C., concentrated under reduced pressure, and purified by silica gel chromatography to obtain the 1-cyano-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)methanesulfonamide B5 in 86% yield as a clear oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, and friends who are interested can also refer to it.

Reference:
Patent; The Regents of the University of California; Amydis, Inc.; Yang, Jerry; Theodorakis, Emmanuel A.; Sarraf, Stella; US2018/327373; (2018); A1;,
Ether – Wikipedia,
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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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C13H11BrO

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.176 g, 0.67 mmol), 3- methoxycarbonylphenylboronic acid (0.18 g, 1 mmol), barium hydroxide (0.25 g, 1.47 mmol), Pd(PPh3)4 (0.077 g, 0.067 mmol), DME (5 mL) and H2O (3 mL) was microwaved with vigorous stirring using a CEM-discover system (ram time: 2min, hold time: 5min, temperature: 120C, pressure: 200 psi, power: 250 W). The crude reaction mixture filtered through a plug of celite and concentrated in vacuo. The residue obtained was purified by flash column chromatography (25% diethyl ether-hexane) to give the title compound (29) (0.118 g, 60% yield) as a viscous liquid.[0280] 29 was confirmed as follows: 1H NMR (500 MHz, CDCl3) delta 8.27 (t, J = 1.5 Hz, 1H), 8.20 (dd, J = 8.0 Hz, J = 1.5 Hz, 1H), 7.76 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.50 (t, J = 8.0 Hz, 1H), 7.47 (d, J = 7.5 Hz, 2H), 7.42-7.32 (m, 4H), 7.25-7.22 (m, 2H), 7.00 (dd, J = 8.2 Hz, J = 2.0 Hz, 1H), 5.13 (s, 2H), 3.95 (s, 3H).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; WO2009/52319; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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 38336-04-8, Product Details of 38336-04-8

To a solution of 3-hydroxy-2,2-dimethylpropanoic acid (2.36 g, 20 mmol), 2-(benzyloxy)ethanamine (3.02 g, 20 mmol), and HOBt (2.71 g, 20 mmol) in dry dichloromethane (100 mL) was added EDCI (3.82 g, 20 mmol) at room temperature under nitrogen. The reaction mixture was then stirred at room temperature under nitrogen overnight. The reaction was quenched with brine, and extracted with EtOAc (3*). The combined organic layers were washed with saturated NaHCO3 solution, dilute HCl, brine, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting with 40% EtOAc in hexanes to give the title compound as colorless oil (4.89 g) in 97% yield. MS 252 (MH+).

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-(Benzyloxy)-1-ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); 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. 20265-97-8, name is 4-Methoxyaniline hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 20265-97-8

6-Methoxy-3-nitroquinoline 14. p-Anisidine hydrochloride (35.0 g, 219.4 mmol) was weighed into a dry 300 mL three-necked round-bottomed flask, equipped with a magnetic stirring bar, a pressure-equalizing addition funnel, a solid addition funnel and a thermometer. Glacial acetic acid (150 mL) was added to the solid, with vigorous stirring to maintain a homogeneous suspension. To this suspension was added sodium nitromalonaldehyde monohydrate (12.0 g, 76.4 mmol) and the mixture stirred for 1.0 h at 25 C. A short-path distillation head was placed on the flask and approximately 120 mL of acetic acid/water removed under reduced pressure at 40 C. To the residue (imine 13) was added glacial acetic acid (40 mL) and sulfolane (75 mL). The resulting solution was flushed with argon to:remove air and the flask immersed in an oil bath preheated to 195 C. The mixture was vigorously stirred while acetic acid was removed by distillation. When the temperature reached 184-185 C. the mixture was stirred for a further 15 min at 185 C. and then poured (while still at ca. 180 C.) onto crushed ice (750 g). The resulting solution was allowed to stand in a refrigerator (overnight) until precipitation was complete. The dark brown solid precipitate was filtered and transferred to a round-bottomed flask (500 mL) containing 2M hydrochloric acid (250 mL). The mixture was heated at reflux for 50-60 min and the boiling; solution filtered through a preheated Buchner funnel to remove an insoluble brown gum. The hot filtrate was cooled to ca. 4 C. and extracted with chloroform (4*50 mL). The combined extracts were dried (MgSO4) and the chloroform removed on a rotatory evaporator to give the crude 3-nitro-6-methoxyquinoline 14 (9.3 g, brown 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; Board of Regents, The University of Texas System; US5442065; (1995); A;,
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Related Products of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Step 4 4-bromo-2-methoxy-5-nitroaniline (compound 12-6) Potassium nitrate (217 mg, 2.25 mmol) was added to a solution of compound 12-5 (400 mg, 2.0 mmol) in 3.5 ml of concentrated sulfuric acid at -20 C., and vigorously stirred at -20 C. for 5 min. After completion of the reaction, the reaction mixture was diluted with water, extracted with EA/water system, washed with water for three times, and dried, and the organic layer was concentrated under reduced pressure to give the crude product compound 12-6 (300 mg) which was used directly in the next step. MS m/z (ESI): 246.9 [M+H]+.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO. LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; XIE, Jing; SHEN, Sida; HU, Yi; LIU, Wei; LV, Qiang; (96 pag.)US2017/8889; (2017); A1;,
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Application of 19056-40-7, These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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 stirred solution of 4-bromo-3-methoxyaniline (1 g, 4.98 mmol) in 3:2 toluene/water (10 mL) was added cyclopropylboronic acid (514 mg, 5.98 mmol), Pd(OAc)2 (56 mg, 0.25 mmol), PCy3 (140 mg, 0.5 mmol) and K3PO4 (3.18 g, 15 mmol) at room temperature. The mixture was stirred at 100° C. for 10 h. The solid was filtered and the filtrate concentrated in vacuo. Purification by silica gel chromatography (2-10percent ethyl acetate/hexanes) provided 4-cyclopropyl-3-methoxyaniline (200 mg, 25percent) as a brown solid. 1H NMR (300 MHz, CDCl3) delta 6.67 (d, J=7.8 Hz, 1H), 6.24-6.20 (m, 2H), 3.82 (s, 3H), 3.50 (brs, 2H), 2.02-1.95 (m, 1H), 0.85-0.79 (m, 2H), 0.57-0.51 (m, 2H)

The synthetic route of 19056-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; US2010/168094; (2010); A1;,
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Some common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, molecular formula is C11H16O4, 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. Recommanded Product: 1,2,3,4-Tetramethoxy-5-methylbenzene

Step 3a: Synthesis of 1-Bromo-2,3,4,5-tetramethoxy-6-methyl benzeneTo a stirred solution of l,2,3,4-tetramethoxy-5-methylbenzene (obtained in Step 2a) (1.60 g, 7.54 mmol) in DCM (50 mL), a solution of bromine (0.41 mL, 7.92 mmol) in DCM (15 mL) was slowly added, and the resulting mixture was stirred at room temperature for 1 h. Water was added, the organic layer was separated and washed with 1 M NaOH and brine. The combined organic layers were dried over sodium sulphate and concentrated to dryness to give the product as yellow oil (2.00 g, 91%).Yield: 91%. TLC: R/= 0.80 petroleum ether:EtOAc 90:10 v/v. Spectroscopic data were as those reported in the literature by Tremblay, M. S. et al, Org. Lett. 2005, 7, 2417

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35896-58-3, its application will become more common.

Reference:
Patent; NICOX SCIENCE IRELAND; BLANGETTI, Marco; FRUTTERO, Roberta; GASCO, Alberto; GIORGIS, Marta; LAZZARATO, Loretta; ROLANDO, Barbara; ALMIRANTE, Nicoletta; STORONI, Laura; WO2015/155234; (2015); A1;,
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Synthetic Route of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of Ph3P (3148 mg, 12 mmol, 1 equiv) and hexachloroethane (2982 mg, 12.6 mmol, 1.05 equiv) in CHCl3 (total volume 40 mL) was stirred at 65 °C for 8 h. After cooling to r.t., under N2, to the mixture was added saccharin (7690 mg, 42.0 mmol, 3.5 equiv) in one portion, followed by the addition of the stock solution of DIPEA in CHCl3 (1.32 M, 59 mL, 78 mmol, 6.5 equiv). The resulting mixture was heated under N2 at 60 °C for 6 h. The mixture was cooled to r.t. and filtered under N2. The solid crude was washed with CHCl3 (3 × 5 mL) and dried under vacuum. The dry solid (5410 mg) was kept under N2. No further separation was attempted, and the resulting solid was used directly in the parallel chemistry. The total yield from Ph3P to the solid was assumed to be 100percent, thus the theoretical amount of the ?active? mixture of 13 and 14 was 451 mg/mol. Parallel Chemistry; General Procedure (Scheme 5) Under N2, to a mixture of the dry solid 13/14 (226 mg, 0.5 mmol) was added a stock solution of DIPEA (1.5 M, 2.17 mL, 3.25 mmol, 6.5 equiv) in CHCl3 at r.t. The mixture was stirred at r.t. for 5 min before a solution of the appropriate amine (1.0 mmol, 2 equiv) in CHCl3 (2 mL) was added. If the amine was in the form of HCl salt, 1 equiv extra of DIPEA was added to the reaction mixture. The resulting mixture was stirred at r.t. for 20 h, and then heated at 60 °C for 15 min. The solvents were evaporated, and the dry residue was dissolved in DMSO (4 mL). The DMSO solution was submitted to purification group for isolation.

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

Reference:
Article; Chen, Yantao; Aurell, Carl-Johan; Korsgren, Pernilla; Malm, Johanna; Haerslaett, Malin; Friden-Saxin, Maria; Pettersen, Anna; Synthesis; vol. 50; 7; (2018); p. 1471 – 1481;,
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Reference of 19500-02-8,Some common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-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.

A stirred solution of amine 2 (42.58 g, 0.31 mol) and di-tert-butyl dicarbonate (65.48 g, 0.30 mol) in THF (300 mL) was heated to maintain reflux for 4 h. After cooling to RT, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc (500 mL). The resultant solution was washed with 0.5 M citric acid (2.x.100 mL), water (100 mL), saturated aqueous NaHCO3 (200 mL), brine (200 mL) and dried over MgSO4. After filtration and removal of the solvent from the filtrate, the residue (red oil, 73.6 g) was dissolved in hexanes (500 mL) and filtered through a pad of Silica Gel (for TLC). The filtrate was evaporated under reduced pressure to provide N-Boc aniline 3 as a yellow solid. Yield: 68.1 g (96percent).

The synthetic route of 19500-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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

Example 57A (102mg, 0.50 mmol) was treated with concentrated HCl (10 mL), cooled to 0 C, treated with a solution OF NAN02 (45MG, 0.65 mmol) in H20 (5 mL), stirred at 0 C for 1 hour, treated with a solution of KI (249mg, 1.5 mmol) in H20 (5 mL), stirred overnight while warming to room temperature, and extracted with ethyl acetate. The extract was washed with H20 and 10% Na2S203, dried (MGS04), filtered, and concentrated to provide 147mg (94%) of the desired product. MS (ESI) m/e 332 (M+20) + ; LH NMR (300 MHz, DMSO-d6) 8 7.39 (d, J = 1. 87 Hz, 1H), 7.34 (d, J = 8. 11 HZ, 1H), 7.24 (dd, J = 8. 11,1. 87 HZ, 1H), 3.86 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem