Month: July 2021

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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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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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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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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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. 701-07-5, name is 2-(2′-Bromophenoxy)propane, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 701-07-5

General procedure: A degassed solution containing the aryl bromide (9a, 183 mg, 0.852 mmol), anhydrous LiCl (286 mg, 6.82 mmol), Ph3P (112 mg, 0.426 mmol) and Pd(Ph3P)2Cl2 (71.7 mg,0.102 mmol) in anhydrous diglyme (2 mL, final concentration of 9a ca. 0.15 M) was treated dropwise with allyltri(n-butyl)tin (0.32 mL, 1.02 mmol). The reaction mixture was heated at 130C under an argon atmosphere. A sample taken at 6 h and worked up allowed the isolation of 1-allyl-2-isopropoxybenzene.3IR (film): 605, 734, 864, 995, 1046, 1174, 1287, 1372, 1383, 1489, 1587, 1638, 2931,2978, 3077 cm-1. 1H NMR (300 MHz, CDCl3): d 1.33 (d, J D 6.0 Hz, 6H), 3.37 (d, J D6.7 Hz, 2H), 4.54 (septet, J D 6.0 Hz, 1H), 5.00-5.09 (m, 2H), 5.93-6.03 (m, 1H), 6.83-6.89 (m, 2H), 7.12-7.18 (m, 2H). 13C NMR (75 MHz, CDCl3): d 22.2, 34.6, 69.9, 113.0,115.2, 120.2, 127.1, 129.7, 129.9, 137.2, 155.5. MS (EI, 70 eV): m/z (%) 91 (13), 115(12), 119 (46), 133 (46), 134 (100), 135 (10), 176 [M]C(66), 177 [MC1]C(9). MS found:176.1207; C12H16O requires m/z: 176.1201. When the reaction was heated during 14 h, complete consumption of the starting material took place, as determined by GC analysis. Then, the reaction mixture was allowed to attain ambient temperature and was diluted with 25 mL of hexanes and filtered through a short pad of Florisil and Celite (1:1). The filtrate was washed successively with saturated NaF (4 £ 10 mL), H2O (3 £ 10 mL), brine (15 mL) and H2O2 (10 mL of a0.12% P/V solution), dried over Na2SO4 and evaporated in vacuo. The oily residue was re-dissolved in CH2Cl2 and stirred an additional period of 12 h with 200 mg activated fluorous silica. Filtration and evaporation of volatiles afforded 90 mg (73%) of the expected beta-methylstyrene (3), as a colorless oil.IR (film): 606, 782, 862, 959, 1049, 1176, 1289, 1383, 1484, 1596, 1655, 2876, 2933,3070 cm-1. 1H NMR (300 MHz, CDCl3): d 1.35 (d, J D 5.9, 6H, Me2-CH), 1.90 (dd, J D1.5 and 6.6, 3H, Me-CH=CH-Ar), 4.57 (septet, J D 5.9, 1H, Me2-CH), 6.22 (dq, J D 6.0,13.9 and 15.2, 1H, Me-CH=CH-Ar), 6.72 (dq, J D 1.5 and 15.9, 1H, CH3-CH=CH-Ar),6.85-6.90 (m, 2H, ArH), 7.14 (dt, J D 1.5 and 7.7, 1H, 4-H), 7.41 (dd, J D 1.4 and 7.5,1H, 6-H). 13C NMR (75 MHz, CDCl3): d 18.9 (Me-CH=CH-Ar), 22.2 (Me2-CH-O), 70.8(Me2-CH), 114.3 (6-C), 120.7 (5-C), 125.8 (2-C), 125.9 (CH3-CH=CH-Ar), 126.4 (CH3-CH=CH-Ar), 127.5 (3-C), 128.2 (5-C), 154.6 (1-C). MS (EI, 70 eV): m/z (%) 77 (10), 91(24), 105 (13), 107 (9), 115 (17), 117 (12), 119 (69), 133 (54), 134 (100), 147 (12), 176[M]C(52), 177 [MC1]C(7). MS found m/z D 176.1198; C12H16O (MC) requires m/z D176.1201. The spectral data were in full agreement with those described.2,3,5,8

According to the analysis of related databases, 701-07-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Simonetti, Sebastian O.; Larghi, Enrique L.; Kaufman, Teodoro S.; Organic Preparations and Procedures International; vol. 47; 3; (2015); p. 227 – 231;,
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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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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. 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C20H16FNO

To a solution of [RhCl(cod)]2(2 mol %) and N-(4-(benzyloxy)benzylidene)-4-fluoroaniline(1B, 0.5 mmol) in THF (1.25 mL) at room temperature was added BF3·Et2O (0.6 mmol), andthen it stirred for 30 min at the same temperature. Subsequently, 5,6-dihydro-2H-pyran-2-one (2h, 0.6 mmol) was added to the suspension mixture, and then 1.0 M Et2Zn in hexane (1.5 mmol, 1.5 mL) was gradually added to the mixture and stirred for 24 h. The mixture was quenched with sat. NH4Cl and extracted with AcOEt. The AcOEt layer was washed with sat. NaCl and dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by column chromatography (AcOEt/hexane = 4:6) and anti diastereomer was obtained in 46% (93.3 mg) [2].

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 70627-52-0.

Reference:
Article; Isoda, Motoyuki; Sato, Kazuyuki; Kunugi, Yurika; Tokonishi, Satsuki; Tarui, Atsushi; Omote, Masaaki; Minami, Hideki; Ando, Akira; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1608 – 1615;,
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Related Products of 175278-17-8, These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, 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.

EXAMPLE 94 2-[(phenylsulfonyl)amino]-4-(trifluoromethoxy)benzoic acid The desired product was prepared by substituting 2-bromo-4-(trifluoromethoxy)aniline for 2-bromo-4-isopropylaniline in Examples 2A-D. MS (ESI(+)) m/e 362 (M+H)+, 379 (M+NH4)+, 384 (M+Na)+; (ESI(-)) m/e 360 (M-H)-; 1H NMR (300 MHz, DMSO-d6) delta 7.76 (m, 1H), 7.73 (m, 1H), 7.68 (m, 1H), 7.51 (m, 3H), 7.39 (d, 1H), 7.20 (m, 1H).

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Comess, Kenneth M.; Erickson, Scott A.; Henkin, Jack; Kalvin, Douglas M.; Kawai, Megumi; Kim, Ki H.; BaMaung, Nwe Y.; Park, Chang Hoon; Sheppard, George S.; Vasudevan, Anil; Wang, Jieyi; Barnes, David M.; Fidanze, Steve D.; Kolaczkowski, Lawrence; Mantei, Robert A.; Park, David C.; Sanders, William J.; Tedrow, Jason S.; Wang, Gary T.; US2004/157836; (2004); A1;,
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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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6F12O2

In a three-port glass reaction flask with a stirring and condenser in a volume of 0.25L,First add 80g of dioxane, 10g of sodium borohydride, stir and mix.After heating to 50 C, 83 g of perfluoro-2-methyl-3-oxa-hexanoyl fluoride was added dropwise, and the reaction was continued for 2 hours after the addition, and the material was distilled off after the reaction.The crude material was collected by freezing to obtain 96 g. The content of 2-perfluoropropoxy-2,3,3,3-tetrafluoropropanol in the crude material was 75%, and the product yield was 91%.

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 2062-98-8.

Reference:
Patent; Zhejiang Lantian Environmental Protection Gao Technology Co., Ltd.; Sinochem Lantian Group Co., Ltd.; Han Guoqing; Xiang Wenqin; Chen Mingyan; Sheng Nan; (5 pag.)CN108264451; (2018); A;,
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Related Products of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 solution of the product from Part B (23.45 g, 16 mmol) in N,N-dimethylformamide (140 mL) was added potassium carbonate (19.3 g, 140 mmol), bis-(2-bromoethyl)ether (9.1 mL, 70 mmol), and 18-Crown-6 (1 g). The slurry was stirred at 60 C. After 16 hr, the reaction was filtered, and the filtrate was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water (3×) and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The product was recrystallized from methanol to provide 19.79 g (70%) of the desired compound as a white solid. (ESMS m/z=405 [M+H]+.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Freskos, John N.; Fobian, Yvette M.; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Carroll, Jeffery N.; DeCrescenzo, Gary A.; Hockerman, Susan L.; Kassab, Darren J.; Kolodziej, Steve A.; McDonald, Joseph; Mischke, Deborah A.; Norton, Monica B.; Rico, Joseph G.; Talley, John J.; Villamil, Clara I.; Wang, Lijuan Jane; US2004/10019; (2004); A1;,
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