Tag: M.W=100-200

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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H14O3

Step A: Methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (922 mg, 3.6 mmol) from Step C of Example 13 was stirred in glacial acetic acid (2.5 mL) and(trimethoxymethyl)benzene (2.0 g, 10.9 mmol) at 70 0C for 3 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate) to give methyl l-(2,2- dimethoxyethyl)-2-phenyl-lH-benzo[J]imidazole-7-carboxylate as a brown oil (1.0 g, 83%): 1H NMR (500 MHz, CDCl3) delta 7.99 (d, J = 8.0 Hz, I H), 7.95 (d, J= 8.0 Hz, I H), 7.72-7.70 (m, 2H), 7.53-7.51 (m, 3H), 7.33 (t, J = 8.0 Hz, I H), 4.76 (d, J= 5.0 Hz, 2H), 4.24 (t, J= 5.0 Hz, I H), 3.99 (s, 3H), 3.07 (s, 6H); MS (ESI+) m/z 341 (M+H).

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; GUZZO, Peter, R.; MANNING, David, D.; EARLY, William; WO2011/8572; (2011); A2;,
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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. 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Methoxyethoxy)ethanamine

2.55 g (20 mmol) of oxalyl chloride are added to 10 g (16.5 mmol) of the title compound from Example 1a in 100 ml of dichloromethane and the mixture is stirred at room temperature for 14 h. It is evaporated to dryness in vacuo, the residue is dissolved in 100 ml of dichloromethane, 3.93 g (33 mmol) of 2-(methoxyethoxy)ethylamine (Whitesides et al., JACS, 1994, 5057-5062) are added and the mixture is subsequently stirred at room temperature for 4 h. The reaction solution is treated with 100 ml of 1 N hydrochloric acid, and thoroughly stirred for 15 min. The organic phase is separated off, dried over magnesium sulphate and evaporated to dryness in vacuo. The residue is chromatographed on silica gel (eluent: ethyl acetate/hexane 1:1). Yield: 11.2 g (96% of theory) of a colourless wax

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; Platzek, Johannes; Schirmer, Heiko; Weinmann, Hanns-Joachim; Misselwitz, Bernd; Zorn, Ludwig; US2008/159954; (2008); A1;,
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Reference of 6346-09-4, 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Under an argon atmosphere, a solution is prepared containing amino acetal (1.2 mmol) and triethylamine (2.0 mmol) in dry chloroform (10 mL). The mixture is cooled to 0 C and a solution of the acid chloride (1 mmol, in 5 mL of CHCl3) is added slowly with stirring. The mixture is allowed to warm to room temperature for 3 h. Following this reaction period, the mixture is extracted twice with chloroform. The organic extracts are then washed with 1 M HCl, with water, and twice with brine solution. After drying over anhydrous sodium sulphate, the organic solvent is removed by reduced pressure and the crude product is subject to column chromatography (SiO2, hexanes:ethyl acetate).

The chemical industry reduces the impact on the environment during synthesis 4,4-Diethoxybutan-1-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kennedy, Sean; Kethe, Anila; Qarah, Ahmad; Klumpp, Douglas A.; Tetrahedron Letters; vol. 59; 20; (2018); p. 1932 – 1935;,
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Electric Literature of 41789-95-1, The chemical industry reduces the impact on the environment during synthesis 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

To a solution of alpha-bromo-2?-acetonaphthone (386.2 g, 1.57 mol) in dichloromethane (2.5 L) at 0 C. was added compound 3 (249.1 g, 1.65 mol) in 30 min, followed by the addition of triethylamine (220.7 mL, 1.57 mmol) in 45 min. After stirring at 0 C. for 40 min, the reaction mixture was warmed to room temperature and stirred overnight. The reaction solution was then washed with water (2¡Á) and the aqueous layer was re-extracted with dichloromethane (2¡Á). The combined organic extract was dried over sodium sulfate and concentrated in vacuo. The ketone, compound 4, was obtained as a reddish oil (513.3 g, quantitative), was used in the next step without further purification: 1H NMR (CDCl3, 500 MHz) 8.50 (s, 1H), 8.01 (d, J=8.5 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.88-7.85 (m, 2H), 7.60-7.54 (m, 2H), 7.26-7.23 (m, 1H), 6.97-6.94 (m, 2H), 6.82 (dd, J=8.0, 2.5 Hz, 1H), 3.88 (s, 2H), 3.75 (s, 3H), 3.69 (s, 2H), 2.42 (s, 3H); ESI MS m/z 320 [M+H]+

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qiu, Jun; Gao, Qui; Liu, Shuang; Hu, Min; Yang, Yuh-Lin Allen; Isherwood, Matthew; Amin, Rasidul; US2014/275101; (2014); A1;,
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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. 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of N-(4-Methoxybenzyl)cyclopropanamine

6,8-Dichloroimidazo[l,2-b]pyridazine-3-carboxamide (2.5 g, 10.9 mmol), N-(4- methoxybenzyl)cyclopropanamine (3.36 g, 18.98 mmol) and diisopropylethylamine (4.42 ml, 25.3 mmol) were dissolved in tetrahydrofuran (THF, 100 mL) and then refluxed overnight. The solvent was removed in vacuo and the crude product was taken up in chloroform and purified via chromatography to provide the product (2.6 g, 64% yield). NMR (400 MHz, DMSO-D6) delta ppm 8.10 (1 H, s), 7.96 (2 H, s), 7.11 (2 H, d, J=8.56 Hz), 6.83 (2 H, d, J=8.81 Hz), 6.73 (1 H, s), 5.65 (2 H, s), 3.68 (3 H, s), 2.55 – 2.63 (1 H, m), 0.93 – 1.03 (2 H, m), 0.76 – 0.84 (2 H, m).

The synthetic route of 70894-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
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Application of 321-28-8, These common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-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.

Step 1: 3-(3-fluoro-4-methoxybenzoyl)propionic acid Intermediate 351-Fluoro-2-methoxybenzene (7 mL, 0.062 mol) and succinic anhydride (6.93 g, 0.0692 mol) were dissolved in methylene chloride (100 mL). The resulting solution was cooled in an ice-water bath for 20 min. Aluminum trichloride (18.3 g, 0.137 mol) was then added in portions. Upon completion of addition, the mixture was heated at 65 C. in an oil bath for 2 h and then cooled to room temperature and allowed to stir overnight. The reaction mixture was poured onto ice and 200 mL 1N HCl was added. A white precipitate formed which was isolated by suction filtration. The filter cake was dried under suction and then further dried under vacuum to provide the title compound as a white solid (12.703 g, 90%). LC-MS: (FA) ES- 225; NMR (400 MHz, CD3OD) delta ppm 7.86 (ddd, J=8.6, 2.1, 1.14 Hz, 1H), 7.72 (dd, J=12.1, 2.1 Hz, 1H), 7.20 (dd, J=8.5, 8.5 Hz, 1H), 3.95 (s, 3H), 3.28-3.23 (m, 2H), 2.71-2.66 (m, 2H).

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2012/15942; (2012); A1;,
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Electric Literature of 1535-75-7,Some common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, 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.

Preparation 11(2 -Trifluoromethoxy-phenvD-hydrazine hydrochlorideTo a stirred solution of hydrochloric acid (37%, 1.6 L) at 0 0C is added 2- trifluoromethoxy-phenylamine (200 g, 113 mmol) followed by water (160 mL) and additional hydrochloric acid (160 mL). The mixture is warmed to room temperature, is stirred for 20 minutes, and is cooled to -5 0C. A solution of sodium nitrite (82 g, 1.19 mmol) in water (400 mL) is added dropwise keeping the internal temperature below 0 0C. The mixture is cooled to -5 0C and a solution of tin (II) chloride dihydrate (1020 g, 4520 mmol) in of HCl (37%, 3.2 L) is added dropwise keeping the internal temperature below O0C. The mixture is warmed to room temperature, is stirred for 3 h, filtered, and washed with 6 N HCl (3L) to obtain a yellow solid that is dried under vacuum overnight The title compound (115.8 g, 54%) is obtained pink-brown solid.Preparation 12 Trifluoromethoxy-phenyl-hydrazine hydrochlorideThe title compound (115.8 g, 54%) is prepared essentially according to the preparation of (2-trifluoromethoxy-phenyl)-hydrazine hydrochloride using 2- trifluoromethoxy-phenylamine.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/140183; (2007); A1;,
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Electric Literature of 41365-75-7, These common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, 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.

Part A A solution of 1-amino-3,3-diethoxypropane (5.00 mL, 30.9 mmol) in 5 mL of tetrahydrofuran (THF) was treated with triethylamine (4.51 mL, 34.0 mmol) under an atmosphere of nitrogen and cooled to 0 C. The reaction mixture was then treated dropwise with a solution of di-tert-butyl dicarbonate (7.42 g, 34.0 mmol) in 25 mL of THF. The reaction mixture was stirred for 2 h at 0 C. and then allowed to come to room temperature. After 15 h, the reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with water (2*) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl (3,3-diethoxypropyl)carbamate (8.40 g) as a clear, faintly yellow oil.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Griesgraber, George W.; Manske, Karl J.; US2005/54640; (2005); A1;,
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Related Products of 5961-59-1, These common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, 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.

HATU (1.5 g, 4.0 mmol) was added to a stirred solution of 4-methoxy-N- methylaniline (500 mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.0 mmol) in DMF (20 mL) and DIPEA (1.3 mL, 7.3 mmol) and the reaction mixture was stirred at RT for 4h. The reaction was concentrated and the residual crude oil was partitioned between EtOAc (60 mL) and 1/2 sat. NaHCO3 (aq) (60 mL). The organic component was washed with brine (40 mL), dried (Mg504), filtered, concentrated and purified using a Biotage Horizon (80g5i02, 10-40% EtOAc/hexanes) to yield (5)-tert-butyl (1-((4- methoxyphenyl)(methyl)amino)- 1 -oxo-3 -phenylpropan-2-yl)carbamate (1.34 g) as a clear amber viscous oil. LC-MS retention time = 3.17 mm; mlz = 385.3 [M+H]. (Column: Phenonenex-Luna C18 2.0 x 50mm 3 pm. Solvent A = 95% Water:5% Acetonitrile:10 miVi NH4OAc. Solvent B = 5% Water:95% Acetonitrile:10 miViNH4QAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time= 4 mm. Wavelength = 220). ?H NMR (400MHz, CDC13) oe 7.25 – 7.20 (m, 3H),7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (q, J=7.4 Hz, 1H), 3.83 (s, 3H),3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s,9H).

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PENDRI, Annapurna; LI, Guo; BENDER, John A.; YANG, Zhong; WANG, Alan Xiangdong; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; MEANWELL, Nicholas A.; GENTLES, Robert G.; WO2015/61518; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, COA of Formula: C7H6F3NO

Pentafluorophenyl chlorothionoformate (2.89 mL, 18.01 mmol) in DCM (10 mL) was added dropwise to 3-(Trifluoromethoxy)aniline (2.189 mL, 16.37 mmol) and Pyridine (1.986 mL, 24.56 mmol) in dichloromethane (180 mL) at O0C. The resulting solution was stirred at ambient temperature for 20 hours. The reaction mixture was washed sequentially with IM citric acid (100 mL), saturated NaHCCbeta (100 mL), and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 15percent ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford O- perfiuorophenyl 3-(trifluoromethoxy)phenylcarbamothioate (3.70 g, 56.0percent) as a yellow oil. IH NMR (400 MHz, CDC13) delta 7.08 (IH, s), 7.13 – 7.19 (2H, m), 7.38 (IH, t).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
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