Tag: M.W=100-200

Synthetic Route of 2688-84-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2688-84-8 name is 2-Phenoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a 50L double-layer cryostat equipped with mechanical stirring, 5 kg was added (due to batch reaction,A plurality of reactors are simultaneously carried out, so that the amount of the raw materials is sufficient to meet the requirements of the step. 2-Aminodiphenyl ether prepared in the above step (2), 30 L of acetonitrile, and the temperature in the autoclave is lowered to -10 C.4.80 Kg of N-bromosuccinimide was added in three portions, and the reaction was carried out for 2 hours.The mixture is distilled to recover acetonitrile, and then 15 L of water is added to the concentrate.15 L of dichloromethane, stirred and separated, and the organic phase was distilled to recover dichloromethane.Drying again gave a brown solid of 7.06Kg.The product was identified as 1-amino-5-bromodiphenyl ether by 1H-NMR and 13C-NMR.The yield was 99%, and the purity of the product was 98% by liquid chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Xinxiang Runyu New Materials Technology Co., Ltd.; Geng Weizhi; Zhou Yi; Li Heng; Zhang Yinlong; Ma Chenyang; (18 pag.)CN109942527; (2019); A;,
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Reference of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dimethoxyphenylacetylene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, A new synthetic method of this compound is introduced below., Recommanded Product: 41365-75-7

j00273J To a solution of [(R)-(4-chlorophenyl)-[(25,3 S,4R, 5R)-5-(4-chloropyrrolo[2,3 – d]pyrimidin-7-yl)-3 ,4-dihydroxy-tetrahydrofuran-2-yl]methyl] 4-phenylbenzoate (Int-3) (400 .mg,0.69 mmol) in Ethanol (2 mL), 3,3-diethoxypropan-1-amine (2.mL, 12.36 mmol) was added. The mixture was stirred at 80 C for 4 h. LCMS indicated the reaction was completed and formation of the mixture of 22a. The mixture of crude products was used directly for the next step.:_1002741 To the reaction mixture of compound 22a (both [(R)-(4-chlorophenyl)- [(2S,3 S,4R,5R)-5-[4-(3 ,3 -diethoxypropylamino)pyrrolo[2,3 -d]pyrimidin-7-yl]-3 ,4-dihydroxy- tetrahydrofuran-2-yl]methyl] 4-phenylbenzoate (4.mL, 0.16 mmol) and (2R,3 S,4R,5R)-2-[(R)-(4- chlorophenyl)-hydroxy-methyl] -5 -[4-(3 ,3 -diethoxypropylamino)pyrrolo[2, 3 -d]pyrimidin-7- yl]tetrahydrofuran-3 ,4-diol (4 .mL, 0.53 mmol) was contained), hydrazine hydrate (2. mL, 41.15 mmol) was added. The mixture was stirred at 25 C for 4 h. The mixture was purified by reverse phase Chem-flash eluting with CH3CN/H20 from 10/90 to 90/10 to give (2R,35,4R,5R)-2-[(R)-(4- chlorophenyl)-hydroxy-methyl] -5 -[4-(3 ,3 -diethoxypropylamino)pyrrolo[2, 3 -d]pyrimidin-7-yl]tetrahydrofuran-3,4-diol (22b) (297 mg, 0.557 mmol, 85.2% yield) (total yield over two steps) as a yellow solid. LCMS M+H: 507.1

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; PRELUDE THERAPEUTICS, INCORPORATED; LUENGO, Juan; LEAL, Raul, A.; LIN, Hong; SHETTY, Rupa; (153 pag.)WO2018/152501; (2018); 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. 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2,6-Difluoro-3,5-dimethoxyaniline

To a solution of the 7.00 g (33.4 mmol) of 4-cyclopropylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde in 500 mL of toluene was added 6.33 g ( 33.4 mmol, 1 equivalent) of 2,6-difluoro-3,5-dimethoxy-phenylamine and 1.94 g (8.36 mmol, 0.25 equivalents) of camphorsulfonic acid. The reaction was warmed to reflux and the formed water was removed with the aid of a Dean-Stark trap. After reacting for 48 hours, the reaction was concentrated in vacuo. The residue was stirred with ether and filtered. The filter pad was dissolved in dichloromethane, stirred with silica gel, and concentrated in vacuo. The residue was placed in the sample injection module of a Biotage FLASH 75 chromatographic apparatus. Chromatography of the crude material down a Biotage 500 g silica gel column with 2:1 hexane/ethyl acetate, then 1:1 hexane/ethyl acetate and finally 9:1 ethyl acetate/ethanol gave 8.92 g (70%) of title compound as a solid: mp 172 C.-174 C. MS (APCI) (m+1)/z 381.0 Analysis calculated for C17H18aF2N4SO2: C, 53.67; H, 4.77; N, 14.73. Found: C, 53.54; H, 4.58; N, 14.61.

The synthetic route of 651734-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chivikas Connolly, Cleo J.; Deur, Christopher James; Hamby, James Marino; Hoyer, Denton Wade; Limberakis, Chris; Reed, Jessica Elizabeth; Schroeder, Mel Conrad; Taylor, Clarke; US2004/19210; (2004); A1;,
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Synthetic Route of 767-91-9, 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 767-91-9 as follows.

General procedure: The arylalkyne 1,acetic anhydride (Ac2O), and an anhydrous solvent were added to a dried three-necked flask under argon atmosphere and the mixture was stirred for 30 min at room temperature. Further, HCl(g)prepared using H2SO4 and NaCl at 160 8C was added to the mixture through the rubber tube until the starting material conversed completely, monitored by TLC, and the unreacted HCl(g) was absorbed by aqueous NaOH. The solvent was removed and the residue was purified using flash chromatography on a silica gel.

According to the analysis of related databases, 767-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Cai-Xia; Ma, Cun-Hua; Xiao, Fu-Rong; Chen, Hong-Wei; Dai, Bin; Chinese Chemical Letters; vol. 27; 11; (2016); p. 1683 – 1685;,
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Adding a certain compound to certain chemical reactions, such as: 1706-12-3, name is 1-Methyl-4-phenoxybenzene, 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 1706-12-3, Recommanded Product: 1706-12-3

(b) 4-(4-Methylphenoxy)benzenesulfonyl chloride To a solution of 1.84 g (10.0 mmol) of 4-methyldiphenyl ether (see J. Chem Soc., Perkin Trans. 1, 1992, 407-408) with 2 mL of dichloromethane in an ice-bath was added a solution of chlorosulfonic acid (0.73 mL, 11.0 mmol) in 2 mL of dichloromethane dropwise. The resulting mixture was stirred at 0 C. to room temperature for 2 hours, and then oxalyl chloride (11.14 mL, 13.0 mmol) was added dropwise, followed by 0.15 mL of DMF. The resulting mixture was heated to 40 C. for 1 hour and then allowed to cool to room tempereature over a 2 hour period. The reaction mixture was poured into ice-pH 7 phosphate buffer (50 mL), then extracted with EtOAc:Hexane (4:3) (3*150 mL). The combined organic layers were washed with brine (75 mL). The aqueous layer was extracted with EtOAc/Hexane(4:3) (150 mL). The organic layer was dried over Na2 SO4, then evaporated by vacuum to give crude product as white solid. This solid was triturated with hexane and collected by filtration, then dried under high vacuum to give 1.555 g (57%) of 4-(4-methylphenoxy)benzenesulfonyl chloride as white solid: mp 295-300 C. 1 H-NMR (DMSO-d6) delta2.34 (s, 3H), 6.91-6.99 (dd, J=7.7,8.4 Hz, 4H), 7.24-7.27 (d, J=8.4 Hz, 2H), 7.61-7.63 (d, J=8.1 Hz, 2H). Anal. calc. for C13 H11 O3 SCl: C, 55.22; H, 3.92; S, 11.34; Cl, 12.71. Found: C, 55.06; H, 3.95; S, 11.28; Cl, 12.71.

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-Methyl-4-phenoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US6153757; (2000); A;,
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Reference of 20059-73-8, A common heterocyclic compound, 20059-73-8, name is 2-(4-(Aminomethyl)phenoxy)-N,N-dimethylethanamine, molecular formula is C11H18N2O, 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 6 N-[4-[2-(Dimethylamino)ethoxy]benzyl]-2-methoxy-5-sulfamoylbenzamide To a cooled suspension of 14.3 g of 2-methoxy-5-sulfamoylbenzoic acid in 60 ml of tetrahydrofuran were successively added dropwise 6.25 g of triethylamine and 7.45 g of pivaloyl chloride with stirring. The mixture was stirred at the same temperature for 1 hour and then a solution of 10.0 g of 4-[2-(dimethylamino)ethoxy]-benzylamine in 40 ml of tetrahydrofuran was added dropwise with stirring. The mixture was stirred at room temperature for 14 hours and the solvent was evaporated. Hydrochloric acid (10%) was added to the residue and the aqueous solution was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate to give a precipitate, which was washed with water and ethyl acetate, of 16.6 g of colorless crystals. Recrystallization of the crystals from ethanol gave the title compound as colorless needles, m.p. 154-155C. Analysis for C19H25N3O5S:

The synthetic route of 20059-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hokuriku Pharmaceutical Co.,Ltd; EP306827; (1991); B1;,
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These common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, 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. Safety of 1-Bromo-3-methoxypropane

Into a 250-mL 3-necked round-bottom flask, was placed a solution of methyl 3- chloro-4-hydroxybenzoate (10.0 g, 53.59 mmol, 1.00 equiv) in N,N-dimethylfonnamide (100 mL), 1-bromo-3-methoxypropane (12.3 g, 80.38 mmol, 1.50 equiv), potassium carbonate (22.3 g, 161.35 mmol, 3.00 equiv). The resulting solution was stirred for 3 h at 50 C. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3×70 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×100 mL of water and lxlOO mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2). This resulted in 13.1 g (94%) of methyl 3-chloro-4-(3- methoxypropoxy)benzoate as a orange solid. ?H NMR: PHNW-1-2-1 (300 MHz, DMSO) 7.91-7.87 (m, 2H), 7.25 (d, J= 8.4 Hz, 1H), 4.19 (t, J= 6.0 Hz, 2H), 3.86 (s, 3H), 3.50 (t, J=6.3 Hz, 2H), 3.25 (s, 3H), 2.04-2.00 (m, 2H).

The synthetic route of 1-Bromo-3-methoxypropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (81 pag.)WO2018/22282; (2018); 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. 2216-69-5, name is 1-Methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

General procedure: 1 mL [Bmim]NO3, 0.5 mmolsubstrate and 0.25 mmol Br2 were added to a dried 45 mL tube equipped witha magnetic stirring (note: the air in the tube was not removed). Then thereaction tube was sealed to perform the reaction at 80 C for 24 h. Once thereaction time was reached, the mixture was cooled to room temperature and3 mL water was added. Then the desired product was extracted with CH2Cl2(3 10 mL). GC analysis of the mixture provided the GC yield of the product.The product in another parallel experiment was purified by columnchromatography, and identified by 1H NMR and 13C NMR.

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 2216-69-5.

Reference:
Article; Ren, Yun-Lai; Wang, Binyu; Tian, Xin-Zhe; Zhao, Shuang; Wang, Jianji; Tetrahedron Letters; vol. 56; 46; (2015); p. 6452 – 6455;,
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16452-01-0, name is 3-Methoxy-4-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: 1,3-bis(3,4-dichlorophenyl)urea (1). 3,4-dichlorophenylisocyanate (200 mg, 1.064 mmol) and 3,4-dichloroaniline (172 mg, 1.064 mmol) were dissolved in 10 mL of anhydrous dioxane. The reaction mixture was warmed to 55 C, stirred under nitrogen over night and then cooled to room temperature (RT). The solvent was removed under vacuum and the crude was crystallized twice in ethyl acetate/hexane to afford 1 (181 mg, 49%).

The synthetic route of 16452-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Denoyelle, Severine; Chen, Ting; Chen, Limo; Wang, Yibo; Klosi, Edvin; Halperin, Jose A.; Aktas, Bertal H.; Chorev, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 402 – 409;,
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