Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 2752-17-2, name is 2,2′-Oxydiethanamine, 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 2752-17-2, COA of Formula: C4H12N2O

Mixed nanosized TiO2-SiO2 oxide (0.27 g, 1.9 mmol) was added to a solution of acetoacetic ester (2) (3.75 g,28.8 mmol), 1,5-diamino-3-oxapentane (1a) (1.00 g, 9.6 mmol), and toluene (6 ml). The reaction mixture was stirred for 20 h at 90C. After the reaction was complete (TLC control, eluent 5:4:1 EtOAc-hexane-CHCl3), the nanosized oxide was separated by centrifugation, and toluene was removed by distillation. The obtained oil was purified by silica gel column chromatography, using CHCl3 as eluent, and dried under ambient conditions. Yield 2.33 g (74%), yellow oil. IR spectrum, nu, cm-1: 1141 (nuas, –Alk); 3291 (N-H); 1652,1505 (-O-N); 2930, 2978 (Alk-). 1H NMR spectrum,delta, ppm: 1.12-1.14 (6H, m, 2CH3); 1.90 (6H, s, 2CH3); 3.35-3.39 (4H, m, 2NCH2CH2); 3.51-3.55 (4H, m, 2NCH2CH2); 3.92-3.97 (4H, m, 232); 4.34-4.35 (2, m, 2); 8.59 (2H, s, 2NH). Found, %: 58.46; 8.43; N 8.69.16H28N2O5. Calculated, %: 58.51; 8.59; N 8.53.

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:
Article; Radionova, Elena S.; Fedorova, Olga V.; Titova, Yulia A.; Rusinov, Gennady L.; Charushin, Valery N.; Chemistry of Heterocyclic Compounds; vol. 51; 5; (2015); p. 478 – 482; Khim. Geterotsikl. Soedin.; vol. 51; 5; (2015); p. 478 – 482,5;,
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Application of 578-57-4, 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. 578-57-4, name is 1-Bromo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

n-BuLi (3.5 ml of a 1.6 M solution in hexane) was added with stirring at 0 C to a solution of 2-bromoanisole (1.0 g, 5.34 mmol) in dry hexane (10 ml) and the mixture was allowed to stir at room temperature. After 2 h stirring the n-butyl bromide formed in the reaction mixture was evaporated under reduced pressure without introduction of air. Dry THF (10 ml) was added followed by the addition of the finely ground selenium powder (0.42 g, 5.34 mmol) at 0 C. It was stirred for 4 h. It was poured to the ice-cooled saturated NaHCO3 solution and O2 gas was passed to the mixture in a moderate rate for 15 min. The compound was extracted with diethyl ether and dried with anhydrous Na2SO4. The solvent was evaporated to obtain yellow-colored solid. The compound was purified in flash chromatography using petroleum ether and ethyl acetate as solvent. It was characterized by NMR spectroscopy. Yield: 0.58 g (31%), 1H NMR (CDCl3), delta (ppm): 3.91 (s, 6H, OCH3), 6.80-6.83 (d, 2H, ArH), 6.85-6.89 (m, 2H, ArH), 7.19-7.23 (m, 2H, ArH), 7.53-7.55 (d, 2H, ArH); 13C NMR (CDCl3), delta (ppm): 56.4, 110.6, 119.1, 122.4, 128.6, 131.0, 157.3; 77Se NMR (CDCl3), delta (ppm): 328. ESI-MS: m/z: calcd for C14H13O2Se2 [M+Na]+: 396.9222; found: 397.0495.

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

Reference:
Article; Bhowmick, Debasish; Mugesh, Govindasamy; Tetrahedron; vol. 68; 51; (2012); p. 10550 – 10560,11;,
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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. 22236-08-4, name is 3-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 22236-08-4

General procedure: A two neck round bottom flask under argon equipped with acondenser was charged with aldehyde 4 (1.0 equiv.) and 4-chloroaniline 3l (1.1 equiv.) in 2-pentanol [0.3 M] and stirred atreflux for 2 h. The tetronic acid 5 (1.1 equiv.) in 2-pentanol (minimumamount) was then added at reflux. After another 10 min atreflux, the third component aniline 3 (1.0 equiv.) was added neat.The reaction mixture was refluxed for an additional 30 min. Allvolatiles were evaporated under vacuum and the crude product purified by recrystallization in ethanol or by flash chromatographyon silica gel

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:
Article; Jeedimalla, Nagalakshmi; Flint, Madison; Smith, Lyndsay; Haces, Alberto; Minond, Dmitriy; Roche, Stephane P.; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 167 – 179;,
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These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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. Formula: C6H15NO2

A mixture of 3,6-diaminopyrazine-2,5-dicarboxylic acid (200 mg, 1.01 mmol), bis-2- (methoxyethyl) amine (372 mL, 335.5 mg, 2.52 mmol), HOBt-H20 (459 mg, 3.00 mmol), and EDC-HC1 (575 mg, 3.00 mmol) were stirred together in DMF (20 mL) for 1 h at room temperature. The mixture was concentrated to dryness and the residue was partitioned with EtOAc and water. The layers were separated and the EtOAc solution was washed with saturated NaHC03 and brine. The solution was dried over anhydrous Na2S04, filtered and concentrated. Purification by radial flash chromatography (Si02, 10/1 CHCb-MeOH) afforded 228.7 mg (53% yield) of Example 4 as an orange foam: lH NMR (300MHz, CDC1 ), delta 4.92 (s, 4 H), 3.76 (apparent t, J = 5.4 Hz, 4 H), 3.70 (apparent t, J = 5.6 Hz, 4 H), 3.64 (apparent t, J = 5.4 Hz, 4 H), 3.565 (apparent t, J = 5.4 Hz), 3.67 (s, 6 H), 3.28 (s, 6 H). 13C NMR (75 MHz, CDCL3)? 167.6 (s), 145.6 (s), 131.0 (s), 72.0 (t), 70.8 (t), 59.2 (q), 49.7 (t), 47.1 (t). LCMS (5-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time = 3.14 min on 30 mm column, (M+H)+ = 429. UV/vis (100 muMu in PBS) abs = 394 nm. Fluorescence (100 muiotaeta) lambda6Chi = 394 nm

The synthetic route of Bis(2-methoxyethyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIBEACON INC.; DORSHOW, Richard, B.; ROGERS, Thomas, E.; (90 pag.)WO2016/183351; (2016); A1;,
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Application of 20781-20-8,Some common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

Example 6 12,13-(2-methoxycarbonyl-but-2-en-1,4-yl)-12,13-dihydro-5,7-dioxo-6H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 3) 12,13-(2-methoxycarbonyl-2,3-dihydroxy-butan-1,4-yl)-12,13-dihydro-5,7-dioxo-6H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 12) 12,13-(2-carboxy-2,3-dihydroxy-butan-1,4-yl)-12,13-dihydro-5,7-dioxo-6H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 13) 12,13-{2-[(pyridin-4-ylmethyl)carbamoyl]-2,3-dihydroxy-butan-1,4-yl}-12,13-dihydro-5,7-dioxo-6H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 117) 3,4-dichloro-furan-2,5-dione (6.7 g, 40 mmol) was mixed with 2,4-dimethoxy-benzylamine (6.25 mL) in glacial acetic acid (120 mL). The mixture was heated to 80 C. for 18 hrs. Upon cooling, the mixture was poured over ice and the precipitate was collected by filtration, then washed with water and NaHCO3 (aq.) and dried in a vacuum oven to provide 3,4-dichloro-1-(2,4-dimethoxy-benzyl)-pyrrole-2,5-dione Compound 6a (11.08 g, 87%) as a light orange solid. 1H NMR (d6-DMSO, 300 MHz) delta 3.73 (s, 3H), 3.76 (s, 3H), 4.54 (s, 2H), 6.44 (d, 1H, J=8 Hz), 6.57 (s, 1H), 7.12 (d, H, J=8 Hz); MS m/z 340 (M+2+Na), 338 (M+Na), 318 (M+2H), 316 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2,4-Dimethoxyphenyl)methanamine, its application will become more common.

Reference:
Patent; Wilson, Lawrence J.; Murray, William V.; Yang, Shyh-Ming; Yang, Cangming; Wang, Bingbing; US2007/249590; (2007); 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. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Weigh 2,6-diaminopurine nucleoside (CAS No.: 2096-10-8) and dissolve 135.58kg in 1350L DMF.The reaction solution is cooled to 0 ± 2 C,Add NaH 29.10kg under argon protection.The temperature of the addition process was 0 C to 5 C, and the mixture was stirred at 0 C for 1 h.After the above reaction system naturally returns to room temperature,Drop into the system2-bromoethyl ethyl ether 73.64 kg,The reaction was stirred at room temperature.The reaction to the product no longer increases.The water quenching reaction was slowly added to the system at 0 ± 2 C.A 2 M HCl solution was slowly added to the system to adjust the pH to neutral.Concentrate in a vacuum at 65 C until it drops.The residual solid is crystallized in ethanol72.91kg of pale yellow solid,It is a 2′-EOE-2,6-diaminopurine nucleoside.The purity was 98.3%, and the yield was 42.8%.

The synthetic route of 592-55-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Zhaowei Science And Technology Co., Ltd.; Shanghai Zhaowei Biological Engineering Co., Ltd.; Sun Bo; Li Xiqun; Zheng Weijian; Chen Hongyu; (10 pag.)CN108822174; (2018); A;,
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Reference of 101-84-8,Some common heterocyclic compound, 101-84-8, name is Diphenyl oxide, molecular formula is C12H10O, 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.

The reactor was charged with 3.16 g of AlCl3 and 711 g of bromine. Diphenyl oxide (46.1 g, 0.271 mol) and the Br2/Cl2 mixture (BrCl) were cofed to the reactor during 124 minutes at 55 C to 57 C. The rate of addition was at a proportion of about 8.2 g Br2/Cl2 mixture (BrCl) per gram of DPO, such that the addition of both was completed at the same time. The mixture in the reactor was refluxed for 10 minutes after the cofeeds had ended, and deionized H2O was added. The reactor was set for distillation. The halogen (mostly Br2, but also comprised of BrCl and Cl2) was distilled off. When most of the halogen was gone, more deionized water was added. The remaining halogen was distilled off to 1000C. The remaining mixture was cooled to 6O0C, and 30 mL of 25% NaOH was added to pH 13-14. The resultant mixture was filtered and washed well with deionized water. A sample was subjected to GC analysis. The GC trace showed the product to contain 0.26% Br9DPO (meta and para hydrogen isomers only), 2.52% Br9ClDPO, and 97.2% Br10DPO. None (less than 0.02%) of the ortho hydrogen isomer of Br9DPO was detected. The sample was oven dried. [0043] The drawings show illustrative GC traces formed using the recommended gas chromatographic procedure described hereinabove. In these traces, the abscissa is time in minutes and the ordinate is the detector response. A copy of the GC trace of the product formed in Example 1 appears as Fig. 1. In Fig. 1, the peak at 1.358 represents the area percentage of what is deemed to be the meta and para isomers of nonabromodiphenyl oxide. No peak for the ortho-isomer of nonabromodiphenyl oxide was observed. The peaks at 2.103 and 2.200 were deemed to be Br9ClDPO isomers. The peak at 2.649 represents the area percentage of decabromodiphenyl oxide.

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

Reference:
Patent; ALBEMARLE CORPORATION; WO2008/27780; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, 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 111-95-5, HPLC of Formula: C6H15NO2

Propargyl bromide (17.8g, 150mmol) was added dropwise to a mixture of bis(2-methoxy-ethyl)amine (20g, 150mmol) and cesium carbonate (49g, 150mmol) in 350mL of acetone. The mixture was stirred overnight under nitrogen at room temperature. The inorganic salts were then filtered off, and the solvent was removed. The residue was dissolved in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were then evaporated to give 20g of bis-(2-methoxy-ethyl)-prop-2-ynyl-amine: mass spectrum (m/e): M+H 172.

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, Bis(2-methoxyethyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth Holdings Corporation; EP1950201; (2008); A1;,
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Electric Literature of 6298-96-0, A common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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 mixture of (S)-1-(4-methoxyphenyl)-ethylamine (475 mg) and 6-chloropurine riboside (300 mg) in PrOH (70 ml) was heated to 70 C. and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over Sephadex LH-20 gel and eluted with ethanol to yield N6-[(S)-1-(4-methoxyphenyl)-ethyl]adenosine (345 mg) as a white solid: positive ESIMS m/z 402 [M+H]+ and 424 [M+Na]+; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.38 (1H, s, H-2), 8.23 (1H, brs, -NH), 8.18 (1H, s, H-8), 5.90 (1H, d, J=6.3 Hz, H-1′), 5.46 (1H, d, J=6.3 Hz, -OH), 5.42 (1H, m, -OH), 5.20 (1H, d, J=4.5 Hz, -OH), 4.61 (1H, m, H-2′), 4.16 (1H, m, H-3′), 3.98 (1H, m, H-4′), 3.66 (1H, m, H-5’a), 3.54 (1H, m, H-5’b); the (S)-1-(4-methoxyphenyl)-ethyl moiety delta 7.35 (1H, d, J=8.4 Hz, H-2″, H-6″), 6.84 (1H, d, J=8.4 Hz, H-3″, H-5″), 5.48 (1H, m, H-7″), 3.71 (3H, s, -OCH3), 1.51 (3H, d, 7.2 Hz, H-8″); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety 5153.9 (s, C-6), 152.3 (d, C-2), 148.6 (s, C-4), 139.8 (d, C-8), 119.7 (s, C-5), 88.0 (d, C-1′), 85.9 (d, C-4′), 73.6 (d, C-2′), 70.7 (d, C-3′), 61.7 (t, C-5′); the (S)-1-(4-methoxyphenyl)-ethyl moiety delta 158.0 (s, C-4″), 137.1 (s, C-1″), 127.3 (d, C-2″, C-6″), 113.6 (d, C-3″, C-5″), 55.0 (q, -OCH3), 48.2 (d, C-7″), 22.5 (q, C-8″).

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES; Shi, Jiangong; Zhang, Jianjun; Yue, Zhenggang; Li, Min; Zhu, Chenggen; Zhang, Ying; Zi, Jiachen; Wang, Yafang; Fan, Xiaona; Xu, Ruiming; Lin, Sheng; Li, Yan; Yang, Yongchun; Sheng, Li; US2013/45942; (2013); A1;,
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Related Products of 39021-83-5,Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, 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 magnetically stirred solution of 1 ,4-dimethoxy-2,3-dimethyl-benzene (13.90 g, 83.6 mmol) in carbon tetrachloride (300 mL) at room temperature was added N-bromo- succinimide (32.2 g, 176 mmol) in one portion, and the reaction mixture was heated up to 65C. Benzoyl peroxide (0.54 g, 2.23 mmol) was added at 65C, and the reaction mixture stirred for further 4 hours before cooling down to 55C. The reaction mixture was filtered, the solid washed with carbon tetrachloride, and the combined filtrates were concentrated in vacuo to yield 2,3-bis(bromomethyl)-1 ,4-dimethoxy-benzene (26.8 g, 82.7 mmol) in 99% yield.

The synthetic route of 39021-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOVERSYS AG; SCHNEIDER, Peter; RIEDL, Rainer; TIGGES, Marcel; GITZINGER, Marc; PIEREN, Michel; LEVI, Assaf; SEPHTON, Mark; SCHELLHORN, Birgit; ZUEGER, Patrik; BRAND, Michael; GYGAX, Daniel; SPIES, Peter; WO2014/118361; (2014); A1;,
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