Month: February 2021

Reference of 36805-97-7, The chemical industry reduces the impact on the environment during synthesis 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, I believe this compound will play a more active role in future production and life.

To a hot (80 C)solution of 4-bromo-3-methyl benzoic acid (3.00 g, 13.95 mmol) in toluene (250mL), N,N-dimethylformamide di-tert-butylacetal (11.35 g, 50.2 mmol) was added. The mixture was stirred at 80 C for 8 hand at rt for 16 h before another portion of N,N-dimethylformamidedi-tert-butyl acetal (5.67 g, 25.1mmol) was added. Stirring was continued at 80 C for 16 h. The mixture wascooled to rt, diluted with EtOAc and washed with sat. aq. NaHCO3-solutionfollowed by water. The org. layer was separated, dried over Na2SO4,filtered, evaporated and dried under high vacuum at 40 C to give tert-butyl 4-bromo-3-methyl benzoate(2.31 g, 61%) as a pale yellow oil; LC-MS: tR = 1.10 min, [M+1]+ = not detectable. 1HNMR (CDCl3): d 7.86(s, 1 H), 7.66 (d, J = 8.3 Hz, 1 H), 7.59 (d, J = 8.3 Hz, 1 H),2.46 (s, 3 H), 1.61 (s, 9 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, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lescop, Cyrille; Mueller, Claus; Mathys, Boris; Birker, Magdalena; De Kanter, Ruben; Kohl, Christopher; Hess, Patrick; Nayler, Oliver; Rey, Markus; Sieber, Patrick; Steiner, Beat; Weller, Thomas; Bolli, Martin H.; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 222 – 238;,
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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.

General procedure: General Procedure A: To a pressure tube containing ethyl 4,4,4- trifluoroacetoacetate (1.2 eq) and Eaton”s reagent [7.5% wt. phosphorous pentoxide p- toluenesulfonic acid solution ( 1 mL/0.3 mmol)], was added the corresponding aniline (1 eq). Then the pressure vessel was sealed and heated to 130 , and the reaction mixture was stirred overnight. After cooling to 0 C, the reaction was poured into ice water (~5 mL/1 mmol) and the solution pH was adjusted to 5 by the addition of saturated aqueous potassium carbonate. In situations when a pale yellow precipitate was formed, the solution was filtered and the residue was washed with water and cold ethanol, then dried in vacuo to yield the crude 4-hydroxyquinoline. Alternatively, the solution could be extracted with CHCl3 (20 mL x 3) and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo to give the crude 4-hydroxyquinoline. Then the residue was purified by column chromatography using hexane”EtOAc as an eluent (30% of EtOAc) to give the desired products with yields ranging from 45% to 60%. (0217) Characterization data for compound 1 and 1a e have been reported by Kozikowski. [0140] 8-trifluoromethoxy-2-trifluoromethyl-4-quinolinol (compound 1): Yield 51%.1H NMR (DMSO-d6) 7.19 (1H, s), 7.74 (1H, apparent t, J = 8.4 Hz), 7.88 (1H, d, J = 7.2 Hz), 8.28 (1H, d, J = 8.4 Hz), 9.71 (1H, br s).13C NMR (DMSO-d6) 101.5 (q, J = 2.4 Hz), 119.9, 120.8 (q, J = 258 Hz), 122.4 (q, J = 273 Hz), 123.5, 123.7, 127.3, 128.8, 141.8 (q, 1.8 Hz), 144.5 (q, J = 36 Hz), 163.9. UVmax: 294 nm, 303 nm, 315 nm

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; THE TRUSTEES OF DARTMOUTH COLLEGE; CHEUNG, Ambrose Lin Yau; NAIR-SCHAEF, Dhanalakshmi R.; WU, Jimmy; CHEN, Ji; (73 pag.)WO2017/136642; (2017); 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. 801282-00-8, name is 2-Fluoro-3-methoxyaniline, A new synthetic method of this compound is introduced below., Safety of 2-Fluoro-3-methoxyaniline

Preparation of compound 10[00177] To a solution of compound 9 (13 g, 92 mmol) in DMF (100 mL) was added a solution of NBS (16.4 g, 92 mmol, 1.0 eq) in DMF (100 mL) drop-wise. The reaction mixture was stirred at room temperature for 3h, then diluted with ethyl acetate (500 mL) and washed with brine (2xl50mL). The organic phase was dried (Na2S04), filtered and concentrated to give the title compound (10) as brown oil (23 g, 98%) yield). ESI-MS (M+H)+: 219.9.

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; TONG, Youzhi; WO2011/29392; (2011); A1;,
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10541-78-3, name is 2-Methoxy-N-methylaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H11NO

General procedure: To a stirred solution of amine derivative (3 .0 mmol ) in 10 mL of anhydrous py ridine under ice cooling, was addeda solution of 2 chlorosulfonyl benzoic acid 3.6 mmol ) in dichloroethane 10 mL) dropwise. The reaction mixturewas stirred at room temper ature under the nitrogen atmosphere for overnight. After completion of the reactio n(monitored by TLC), reaction mixture was diluted with chloroform (20 mL) and quenched with water (10 mL),extracted with chloroform (3x 3 0 mL), the organic layer was washed with 1N HCl (50 mL), then with water (50mL) The combined organic layers were dri ed over Na 2 SO 4 and evaporated in vacuo . The crude compoundrecrystallized from ethanol to afford the desired product 1a m

The synthetic route of 10541-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Junmin; Wang, Qiuhong; Li, Xiangkang; Zhao, Yongli; Arkivoc; vol. 2019; 6; (2019);,
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Related Products of 80936-82-9, 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. 80936-82-9, name is 4-(Methoxymethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

The synthetic route of 4-(Methoxymethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
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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 1515-95-3 as follows. HPLC of Formula: C9H12O

General procedure: In a 25 ml dry round-bottom flask was suspended polymeric PhIO (0.25 equivalent) indry acetonitrile at 23C. Then, Al(NO 3 ) 3 (0.35 equivalent) was added and stirred for10 min, afterward, it was cooled to 0C. The benzylic aryl derivative (1 equivalent) wasincorporated in one portion. The reaction was warmed to 23C for a period of 2-4 huntil the starting material was fully consumed judging its advance by TLC. The reactionmixture was quenched by the addition of NH 4 Cl saturated solution (25 mL) and thenextracted with EtOAc (3 10 mL). The organic extracts were collected, dried overanhydrous sodium sulfate, filtered, and concentrated in vacuo to remove the solventand yield the crude of the reaction. The product was purified by flash column chroma-tography on silica gel (100-200 mesh) with EtOAc/hexane system.

According to the analysis of related databases, 1515-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yahuaca-Juarez, Berencie; Gonzalez, Gerardo; Ramirez-Morales, Marco A.; Alba-Betancourt, Calara; Deveze-Alvarez, Martha A.; Mendoza-Macias, Claudia L.; Ortiz-Alvarado, Rafael; Juarez-Ornelas, Kevin A.; Solorio-Alvarado, Cesar R.; Maruoka, Keiji; Synthetic Communications; vol. 50; 4; (2020); p. 539 – 548;,
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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. 1484-26-0, name is 3-Benzyloxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Benzyloxyaniline

Anhydrous potassium carbonate (74 g, 0.535 mol) was sequentially added to benzyl alcohol (200 g, 1.86 mol, 192 ml).m-Dinitrobenzene (30g, 0.178mol),Stirring, reacting at 110 C for 24 h, cooling in an ice water bath, and filtering off inorganic salts by suction;Add Raney nickel (10g) to the filtrate.Passing hydrogen gas, pressure 2.5~3MPa, internal temperature 80C, reaction for 15h, and recovering nickel by filtration;The filtrate was distilled under reduced pressure, and after removing benzyl alcohol, 50 mL of ethanol was added to the residue, and the mixture was stirred for 2 hours in an ice water bath to precipitate a solid.Drying gives 9.3 g of aminophenol in an off-white solid.The yield was 48%.

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; Shanghai University of Engineering Science; Xu Jingli; Shen Yongjia; Mao Yongjun; Wang Han; (7 pag.)CN109942441; (2019); 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. 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H10BrNO

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 ¡Á 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

The synthetic route of 887581-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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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. 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,2-Dimethoxy-4-methylbenzene

General procedure: To a solvent of (bisacetoxyliodo)benzene (DAIB) (4.75g, 14.75mmol) in dry THF (20-30mL) was added trifluoroacetic acid (1.12g, 9.83mmol) and acetic acid (0.29g, 4.92mmol). The mixture stirred for 30 min, after which the compound added for benzylic C-H oxidation (2.46mmol) and further reacted for 24h. The progress of the chemical reaction was monitored using thin-layer chromatography with precoated silica gel 60 (0.25mm thickness) plates. The reaction was quenched with 1mL of sat. NaHCO3 (aq), and the solvent removed in vacuo on a rotatory evaporator. The residue was extracted with ethyl acetate (30mL¡Á2) and water (20mL). The combined organic extracts were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo.

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 494-99-5.

Reference:
Article; Lin, Chun-Yu; Yang, Ping-Shin; Chou, Pang-Yu; Ong, Chi Wi; Tetrahedron Letters; vol. 59; 4; (2018); p. 365 – 367;,
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33170-72-8, name is 2-Bromo-1,1-dimethoxypropane, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 33170-72-8

A solution of methyl 5-amino-6-bromopyrazine-2-carboxylate (500 mg, 2.15 mmol, 1.00 equiv),2-bromo-i,i-dimethoxypropane (1.2 g, 6.56 mmol, 3.00 equiv), p-toluenesulfonic acid (76 mg,0.44 mmol, 0.20 equiv) in acetonitrile (20 mL) was stuffed for 12 h at 80 C. The mixture was concentrated under vacuum and the residue was purified by a silica gel column eluting with dichloromethane/methanol (10:1). This resulted in 400 mg (69%) of the title compound as a yellow solid. LC-MS (ES, mlz): 270 [M+H].

The synthetic route of 33170-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
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