Tag: M.W=100-200

5961-59-1, 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. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A round-bottomed flask was charged with the aryl halide (1 mmol),the indoline or (het)aryl amine (1 mmol), and Pd2(dba)3 (0.005mmol, 5 mg). At this point, CH2Cl2 (10 mL) was used to dissolve the reactants and to suspend K2CO3 (4 mmol, 552 mg) and Al2O3 (2g). The CH2Cl2 was then removed under reduced pressure and subsequently recovered. The residual powder was ground with a mortar and pestle for 5 min. A microwave oven reactor was charged with the reactant powder which was compacted as much as possible. The powder was heated at 140 ¡ãC for 20 min at medium power (350 W) ,then charged into a flash silica gel column which was eluted with hexane?EtOAc (4:1) to give the purified product. The solid products were further purified by crystallization from hexane?Et2O.

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Reference:
Article; Basolo, Luca; Bernasconi, Alice; Broggini, Gianluigi; Gazzola, Silvia; Beccalli, Egle M.; Synthesis; vol. 45; 22; (2013); p. 3151 – 3156;,
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A common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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. 437-83-2.

Step D: 1-bromo-3-fluoro-2-methoxybenzene: NaN02 (12.0 g, 173 mmol, in 40 mL of water)solution was added dropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 mL of hydrobromic acid ( 4 7 %) and 100 mL of water at -5 ~ 0 C and stirred for 1 hour.This solution was then added slowly to the suspension ofCuBr (45.2 g, 315 mmol) in 50 mL ofhydrobromic acid (47 %) at 0 C. The resulting mixture was stirred at 0 C for 1 hour thenwarmed to 50 C and stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ether (2 X 500 mL). The combined organic layer was washed with brine, driedover anhydrous Na2S04 and concentrated to give 1-bromo-3-fluoro-2-methoxybenzene.

The synthetic route of 3-Fluoro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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710-18-9, The chemical industry reduces the impact on the environment during synthesis 710-18-9, name is 1-Methoxy-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

PREPARATION 18 2-Methoxy-5-trifluoromethoxybenzoyl chloride Combine 2-methoxy-5-trifluoromethoxybenzene (1.0 g, 5.2 mmol) and trifluoroacetic acid (200 mL). Add slowly portionwise hexamethylenetetraamine (26 g, 185.7 mmol). Heat at 60 C. After 24 hours, cool to ambient temperature and pour the reaction mixture into a 2M aqueous solution of sulfuric acid (500mL). Cool and extract ten times with diethyl ether. Dry the combined organic layers over Na2 SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluding with 1/4 ethyl acetate/hexane to give 2-methoxy-5-trifluoromethoxybenzaldehyde.

The chemical industry reduces the impact on the environment during synthesis 1-Methoxy-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoechst Marion Roussel, Inc.; US5922737; (1999); A;,
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Adding some certain compound to certain chemical reactions, such as: 6346-09-4, name is 4,4-Diethoxybutan-1-amine, 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 6346-09-4. 6346-09-4

To a solution of [4,4-bis(ethyloxy)butyl]amine (5.0 g, 30.0 mmol) and Et3N (4.61 ml, 33.0 mmol) in 40 ml_ of THF was added ethyl 1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindole-2- carboxylate (6.9 g, 32.0 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was extracted with hexane. The hexane solution was concentrated in vacuo and heated at 100 0C under reduced pressure to remove ethylcarbamate by sublimation. The mixed solution of diethyl acetal (2.0 g, 6.95 mmol) thus obtained and 1 Lambda/aq. HCI (14 ml_) in acetone (20 ml_) was heated under reflux for 15 min. Acetone was evaporated and aqueous layer was extracted with ether, dried over MgSO4, and filtered. The solvent was evaporated and the residue was moved to next step.

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 4,4-Diethoxybutan-1-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/30761; (2007); A2;,
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366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

28.a. 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone (This product is obtained according to Sugasawa T; Toyoda T; Adachi M; Sasakura K, J Am. Chem. Soc., 100 (1978), p.4842-4852). Boron trichloride (1M in heptane, 156 ml, 156 mmol) is added dropwise, under an argon atmosphere at 0¡ã C. to a solution of 3-fluoro-4-methoxy-aniline (20 g, 142 mmol) in anhydrous dichloromethane (200 ml). The pink suspension thus obtained is maintained under agitation for 5 minutes, then propionitrile (33 ml, 420 mmol) is added dropwise followed by aluminium trichloride (20.8 g, 156 mmol) in small portions. The reaction medium is heated under reflux for 3 hours, cooled down to 0¡ã C., hydrolyzed by cautiously adding 2N hydrochloric acid (100 ml), then heated at reflux for 45 minutes. After cooling down to 0¡ã C. a precipitate is obtained which is filtered out, washed with dichloromethane, then taken up in water (300 ml). The aqueous phase is basified to an alkaline pH, extracted with dichloromethane then ethyl acetate. The organic phase is dried (MgSO4) then evaporated to produce a crude product which is purified by column chromatography (SiO2, AcOEt/Hpt: 1/99 to 20/80). 15.3 g of a yellow solid is obtained. NMR-1H (CDCl3): 1.20 (t, 3H); 2.92 (q, 2H); 3.83 (s, 3H); 6.2 (s, 2H); 6.40 (d, 2H); 7.32 (d, 2H). IR(KBr): 857; 1148; 1240; 1561; 1583; 1662.

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; Bigg, Dennis; Lavergne, Olivier; Pla Rodas, Francesc; Pommier, Jacques; Ulibarri, Gerard; Harnett, Jerry; Rolland, Alain; Liberatore, Anne-Marie; Lanco, Christophe; Cazaux, Jean-Bernard; Le Breton, Christine; Manginot, Eric; US2003/4150; (2003); A1;,
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Adding some certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8. 22236-10-8

Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 4- (difluoromethoxy)benzenamine (10 g, 62.8 mmol), ACN (100 mL), and BS (5.59 g, 31.4 mmol). The resulting solution was stirred for 1 h RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :20 to 1 : 10). This resulted in 7.9 g (53%) of the title compound as red oil. MS-ESI: 238.0/240.0 (M+l).

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 4-(Difluoromethoxy)aniline.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 22236-10-8

1-[(6-AMINOPYRIDIN-3-YL) METHYL]-3-{[4-(DIFLUOROMETHOXY) phenyl] AMINO} ? 4-PHENYL- 1H-PYRROLE-2, 5-dione A mixture OF TERT-BUTYL {5- [ (3-CHLORO-2, 5-dioxo-4-phenyl-2, 5-dihydro-1H-pyrrol-1- yl) methyl] PYRIDIN-2-YL} CARBAMATE (0.70 g, 1.7 mmol) and 4- (difluoromethoxy) aniline (0.54 g, 3.4 mmol) in DMF (4 mL) was heated in a microwave reactor at 150C for 8 min.. The solvent was evaporated and the residue was purified on a pre-packed SIO2COLUMN (ISOLUTE0 SI, lOg/70 mL) using CH2C12 and then CH30HL CH2CL2 (1: 99,2 : 98 and then 5: 95) as eluant to give 0.4 g (54%) of the title COMPOUND. 1H NMR (400 MHz, CDC13) 8 7.99 (bs, 1H), 7.67-7. 62 (m, 2H), 7.14-7. 04 (m, 3H), 6.91 (d, J =8 Hz, 2H), 6.78 (d, J=8 Hz, 1H), 6.72 (d, J=9 Hz, 2H), 6.63 (d, J=9 Hz, 2H), 6.33 (t, J=74 Hz, 1H) and 4.60 (s, 2H).

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/5416; (2005); A1;,
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2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, 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. 2930-05-4

General procedure: A 50mL sealed tube with a magnetic stirring bar was evacuated and backfilled will CO2 for three times, potassium organoaluminate (0.1mmol), (n-Bu)4NI (0.05mmol), epoxide (2.0mmol), and 1.0mL THF were added. The reaction mixture was stirred at 50C (heating mantle temperature) for 24h. The reaction was then quenched with H2O (10mL) and extracted with ethyl acetate (3¡Á15mL). The combined organic layers were dried over Na2SO4 and concentrated. The yields were determined by 1H NMR spectroscopy with trichloroethylene (90muL, 1mmol) as an internal standard. Then, the reaction mixture was purified on silica gel column chromatography (petroleum ether/EtOAc: 3/1). All cyclic carbonates were identified through comparisons with the corresponding 1H NMR, 13C NMR data reported in the literatures [7].

Statistics shows that 2930-05-4 is playing an increasingly important role. we look forward to future research findings about 2-((Benzyloxy)methyl)oxirane.

Reference:
Article; Guo, Zhiqiang; Yan, Leilei; Liu, Yaoming; Wu, Xiaoqin; Wei, Xuehong; Journal of Organometallic Chemistry; vol. 922; (2020);,
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Adding some certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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. 1535-73-5

General procedure: To a stirred solution of 11 (13.14 mmol) in 1,2-dichloroethane (240 mL) were added appropriate substituted anilines (19.71 mmol) and AcOH (13.14 mmol), and the mixture was heated to reflux for 2 h under nitrogen atmosphere. The reaction mixture was cooled to 0 ¡ãC, and MeOH (60 mL) and THF (20 mL) were added. To it, (AcO)3BHNa (26.20 mmol) or NaBH4 (52.56 mmol) was added portionwise, and then the reaction mixture was allowed to warm to room temperature and stirred for an additional 3 h. The pH of the reaction mixture was adjusted to 7?8 at 0 ¡ãC with 1 NHCl, and then the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2¡Á 300 mL). The combined organic layers was washed with brine (300 mL) and dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel to afford the titled compounds as a solid.

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 3-Trifluoromethoxyaniline.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
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The chemical industry reduces the impact on the environment during synthesis 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, I believe this compound will play a more active role in future production and life. 54149-17-6

Example 35 Preparation of N-{2-[2-(2-methoxyethoxy)ethoxy]phenyl}-17-methylmorphinan-3-amine (35), hydrochloride salt (35) Step 1. Synthesis of l-bromo-2-(2-(2-methoxyethoxy)ethoxy)benzene, A mixture of 2-bromophenol (0.448g, 2.59 mmol), l-bromo-2-(2- methoxyethoxy)ethane (0.383mL, 2.85 mmol), and potassium carbonate (1.073g, 7.76 mmol) in dimethyl formamide (5 mL) was stirred at 60 C overnight. The reaction mixture was poured into 20 mL of 5% LiCl solution and extracted with ethyl acetate 3x30mL. The organic layer was washed with brine, was dried over sodium sulfate, was filtered and was concentrated. After drying under high vacuum, the pure product was obtained as colorless oil (656.7 mg) in 92% yield. *Eta NMR (400 MHz, CDCl-3): delta 7.54 (d, 1H), 7.24 (t, 1H), 6.92 (d, 1H), 6.83 (t, 1H), 4.40 (t, 2 H), 3.92 (t, 2H), 3.80 (t, 2H), 3.58 (t, 2H), 3.39 (s, 3H). MS (EI) for CnHi5Br03: 292 (MNH4+).

The chemical industry reduces the impact on the environment during synthesis 54149-17-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
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