Month: May 2021

Related Products of 64465-53-8,Some common heterocyclic compound, 64465-53-8, name is 4-Fluoro-3-methoxyaniline, molecular formula is C7H8FNO, 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.

4-Fluoro-3-methoxyphenylhydrazine Hydrochloride To stirred hydrochloric acid (100 mL) at 0 C. was added 3-methoxy-4-fluoroaniline (10 g, 71 mmol) followed by water (10 mL) and more hydrochloric acid (10 mL). The mixture was warmed to room temperature, stirred for 20 min then cooled to -5 C. A solution of sodium nitrite (5.14 g, 75 mmol) in water (25 mL) was added dropwise such that the internal temperature remained below 0 C. The mixture was warmed to room temperature and stirred for 2 h. The mixture was cooled to -5 C. and a solution of tin(II)chloride dihydrate (64 g, 284 mmol) in hydrochloric acid (200 mL) was added dropwise such that the internal temperature remained below 0 C. The mixture was warmed to room temperature, stirred for 3 h then filtered. The filter-cake was washed with hydrochloric acid and dried in vacuo to give a pink solid (7.4 g). The emerging precipitate from the combined filtrates was filtered-off, washing with hydrochloric acid, to give a further crop of product (1.8 g. Combined yield 9.2 g, 67%); m.p. 250+ C. (dec.); NMR: (400 MHz, DMSO-d6) deltaH10.17 (3H, s, NH3), 8.14 (1H, s, NH), 7.15 (1H, dd,J 11.6, 8.6 Hz), 6.95 (1H, dd, J 7.6, 3.0 Hz), 6.54 (1H, dt, J 8.6, 3.0 Hz), 3.83 (3H, s, MeO).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-3-methoxyaniline, its application will become more common.

Reference:
Patent; Bentley, Jonathan Mark; Davidson, James Edward Paul; Mansell, Howard Langham; Monck, Nathaniel Julius Thomas; US6479534; (2002); B1;,
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Reference of 4179-19-5, 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. 4179-19-5, name is 3,5-Dimethoxytoluene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Stage 1 300 ml of a solution (1.6M) of butyllithium in hexane are added dropwise at room temperature to a solution of 73 g of 3,5-dimethoxytoluene in 450 ml of diethyl ether. The reaction mixture is heated at reflux for 3 hours under an inert atmosphere, the reaction mixture is then cooled to -60 C. and 99.7 g of methyl borate are added dropwise over 60 minutes. The reaction mixture is left at -60 C. for 3 hours and left to return to room temperature. The reaction mixture is stirred at room temperature for 16 hours, 6N hydrochloric acid is then added to the reaction mixture (pH=1) and the reaction mixture is left to separate by settling. The organic phase is recovered. The aqueous phase is extracted with diethyl ether. The combined organic phases are dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a yellow oil which crystallizes by cooling to 0 C. After drying, white crystals of 2,6-dimethoxy-4-methylphenylboronic acid are recovered, M.p.=108 C., Yield 80%.

The synthetic route of 3,5-Dimethoxytoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanofi; US5731340; (1998); A;,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, A new synthetic method of this compound is introduced below., Quality Control of (4-(Trifluoromethoxy)phenyl)methanamine

General procedure: To a solution of 2-(dibenzo[b,d]thiophen-2-yl)imidazo[1,2-a]pyridine-3-carboxylic acid 5 (2.83mmol) in anhydrous DMF (10mL) were added 1-[3-(dimethyl amino)propyl]-3-ethylcarbodiimide (EDCI, 3.84mmol), 1-hydroxybenzo triazole (HOBt, 1.54mmol), triethyl amine (TEA, 5.12mmol) and 6a-s (2.56mmol) at room temperature, and the resulting solution was heated at 80C with stirring. After 12h, the reaction mixture was cooled to room temperature and evaporated. Water (50mL) was added into the crude residue, the resulting solid was collected by filtration, and the filtered cake was washed with water (50mL) and dried to afford crude product. The resulting crude compound was purified by column chromatography over silica gel (n-hexane/EtOAc=1:1) to give 7a-s as a white solid.

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; Pulipati, Lokesh; Sridevi, Jonnalagadda Padma; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 3135 – 3140;,
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Electric Literature of 17061-62-0, 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. 17061-62-0, name is Bis(4-methoxybenzyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[09331 N,N-bis(4-methoxybenzyl)ethenesulfonamide, Example 460.1. To1 L round bottomed flask was added bis(4-methoxvbenzvl)amine 12.01 (23.16 g, 90 mmol) and TEA (anhydrous (43.8 mL, 315 mmol)) in DCM (200 mL). At 0 C (ice bath), 2-chloro-1-ethanesulfonyl chloride (10.41 mL, 99 mmol) in DCM (100 mL) was added dropwise with stirring. The reaction mixture was stirred at 0 C for 3 h after completion of the addition. LCMS analysis indicated the reaction was complete. The reaction mixture was diluted with water and extracted with DCM. The organic extract was washed with brine and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the initial material as a light-yellow oil, which was purified by silica gel chromatography (a gradient of 0-60% EtOAc in hexanes), to provide 460.1 (23 g, 66.2 mmol, 74% yield) as a white solid. LCMS-ESI (POS), mlz: 370.1 (M+Na).

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(4-methoxybenzyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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Related Products of 402-52-8,Some common heterocyclic compound, 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, molecular formula is C8H7F3O, 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 12 Production of 2-Methoxy-5-(trifluoromethyl)acetophenone 97.0 g (0.65 moles) of trifluoromethanesulfonic acid were put into a 200 ml three-necked flask. The flask was equipped with a reflux condenser, a dropping funnel and a thermometer and was connected with a calcium chloride tube for shielding the flask against moisture of the outside. A mixture of 22.8 g (0.13 moles) of 4-(trifluoromethyl)anisole and 26.5 g (0.26 moles) of acetic anhydride was added in a dropwise manner at a temperature of not higher than 30 C. to the flask under stirring. After the adding, the reaction was conducted for 3 hrs at 20-25 C. The resulting reaction liquid was poured into 300 ml of iced water. Then, 200 ml of ether were added to extract the reaction product. Then, 100 ml of ether were added to the aqueous layer to extract the reaction product again. The resulting two ether layers were combined together, followed by washing with 10% sodium hydrogencarbonate aqueous solution until the ether layer is made basic.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methoxy-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Central Glass Company, Limited; US2003/109574; (2003); A1;,
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Related Products of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

Specifically, a solution of 3-benzyloxyaniline 2e (0.84 g, 4.2 mmol) and diphenylcyanocarbonimidate 1 (1.0 g, 4.2 mmol) in 2-PrOH (15 ml_) was stirred at ambient temperature under N2. After 5 h, the solids were collected by filtration washing with cold 2-PrOH to afford 3e (1.25g, 86percent) as a white solid: 1H NMR (300 MHz, DMSO- d6) delta 7.47-7.26 (m, 12H), 7.17 (s, 1H), 7.05 (d, J = 7.9 Hz, 1H), 6.90 (d, J = 8.3 Hz, 1H), 5.10 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Benzyloxyaniline, its application will become more common.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2007/30680; (2007); A2;,
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Related Products of 64115-88-4,Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, 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.

5 rnL microwave vial was charged 4-ethynyl-7H-pyrrolo[2,3-d]pyrimidine (143 mg, 1.0 mmol), l-bromo-2-(trifluoromethoxy)benzene (241 mg, 1.0 mmol), PdCl2(PPhS)2 (35 mg, 0.05 mmol) and CuI (10 mg, 0.05 mmol). 3 mL of anhydrous CH3CN were added, after 10 min of stirring followed by 1.4 mL of Et3N. The reaction mixture was purged with argon for 5 min. Then the vial was capped and placed in a heating block at 60 0C for 18 h. Then it was cooled down to ambient temperature and concentrated in vacuo. The resulting black residue was re-dissolved in 3 mL of DMF and purified by reverse-phase preparative HPLC in CH3CN/H2O system containing 0.1% of TFA. Fractions, containing the product, were combined and partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was washed with brine (1 x 30 mL), dried over anhydrous Na2SO4 and filtered through a short silica gel plug. The filtrate was concentrated in vacuo to give the title product as a yellow solid (43 mg, 14% yield).[0334] 1H NMR (500 MHz, DMSO-J6): delta 6.63 (d, J = 3.5 Hz, IH), 7.55 (dt, J = 7.5, 1.0 Hz, IH), 7.59 (d, J = 8.4 Hz, IH), 7.67 (dt, J = 8.4, 1.7 Hz, IH), 7.75 (d, J = 3.5 Hz, IH), 7.92 (dd, J = 7.7, 1.6 Hz, IH), 8.79 (s, IH), 12.42 (s, IH)[0335] MS (ES+): m/z 304 (M+H)+

The synthetic route of 64115-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN INC.; WO2009/55674; (2009); A1;,
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Some common heterocyclic compound, 2734-70-5, name is 2,6-Dimethoxyaniline, molecular formula is C8H11NO2, 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. SDS of cas: 2734-70-5

Trimethylalurninum (4.7 mL, 9.4 mmol) was added dropwise to a solution of 2,6-dimethoxyaniline (1.2 g, 7.8 mmol) and Compound lb (0.80 g, 9.4 mmol) in toluene (10mL) while cooling in an ice bath. After addition was complete, the reaction mixture was warmed to 110 °C and was stirred at this temperature for l4hrs. The cooled reaction mixture was partitioned between a saturated solution of Rochelle?s salt and EtOAc. The organic phase was separated, dried over MgSO4, filtered and concentrated under reducedpressure. The resulting residue was added to a silica gel (120 g) colunm and was eluted with 0-20percent of 20percent MeOH/DCM in 0.5percent TEA/DCM to give Compound lc (1.1 g, 4.5 mmol, 57 percent) as a brown liquid. MS ,n/z 239.0 (M+H). 1H NMR (500M1-lz, CDC13) 67.01(t, J 8.3 Hz, 1H), 6,62 (d, J= 7.7 Hz, 2H), 5.32 (s, 2H), 4.88 (hr s, 2H), 4.31 (s,2H), 3.82 (s, 6H), 3.62-3.73 (m, 2H), 1.19-1.33 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2734-70-5, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MENG, Wei; CHAO, Hannguang J.; FINLAY, Heather; LAWRENCE, R., Michael; MYERS, Michael C.; (154 pag.)WO2017/96130; (2017); A1;,
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Application of 204452-91-5,Some common heterocyclic compound, 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, molecular formula is C11H16N2O2, 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.

5,6,7,8-Tetrahydro-[1,8]naphthyridine-2-carboxaldehyde. 2-Dimethoxymethyl-5,6,7,8-tetrahydro-[1,8]naphthyridine (10 g, 0.048 mol) was treated with trifluoroacetic acid (50 mL) and the resulting solution stirred under argon for 12.5 h. The TFA was removed at reduced pressure and the residue partitioned between sat. NaHCO3 and CH2Cl2. The organic layer was dried, concentrated and passed through a 3 in. pad of silica gel (10% acetone/CH2Cl2) and concentrated to afford 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carboxaldehyde as a yellow crystalline solid. 1H NMR (300 MHz, CDCl3) delta9.80 (s, 1H); 7.31 (d, J=7.32 Hz, 1H); 7.16 (d, J=7.32 Hz, 1H); 5.31 (br, s, 1H); 3.48 (m, 2H); 2.81 (m, 2H); 1.94 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, its application will become more common.

Reference:
Patent; Payne, Linda S.; Tran, Lekhanh O.; Zhuang, Linghang H.; Young, Steven D.; Egbertson, Melissa S.; Wai, John S.; Embrey, Mark W.; Fisher, Thorsten E.; Guare, James P.; Langford, H. Marie; Melamed, Jeffrey Y.; Clark, David L.; US2003/229079; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8, Safety of 4-(Difluoromethoxy)aniline

To a mixture of 9 (190 mg, 0.74 mmol), 4-(difluoromethoxy)aniline (5a, 130.5 mg, 0.82 mmol) and 4-(dimethylamino)pyridine (DMAP) (99.4 mg, 0.81 mmol) in dimethylformamide (DMF) (3 mL) was added N’-ethylcarbodiimide hydrochloride (EDO HC1 (156 mg, 0.81 mmol), the mixture was stirred at room temperature for 1 h. Then, 100 mL water was added to the reaction mixture to form off-white precipitate, which was collected on a filter to give an off- white solid. The solid was dissolved in ethyl acetate and dried over MgS04, filtered, and the solvent was removed by rotary evaporator. The crude product was purified by recrystallization from ethyl acetate/hexane to afford 2a as white solid (120.4 mg, 41% yield): mp. 174- 177 C; 1H NMR (500 MHz, CDC13) delta 0.92 (t, J = 7.5 Hz, 3H), 1.64 (m, 2H), 2.06 – 2.22 (m, 2H), 2.42 (t, = 7.5 Hz, 2H), 2.49 (t, = 6.9 Hz, 2H), 3.31 (t, = 5.7 Hz, 2H), 6.01 (s, 1H), 6.45 (t, = 74.0 Hz, 1H), 7.07 (d, J = 8.6 Hz, 2H), 7.55 (d, J = 8.6 Hz, 2H), 7.92 (s, 1H), 12.69 (s, 1H). 13C NMR (125 MHz, CDCI3) delta 13.8, 21.1, 24.8, 30.2, 35.5, 39.7, 107.8, 116.1(t, = 259 Hz), 120.6, 121.3, 135.6, 147.3, 160.2, 165.5, 169.9, 170.5; 19F NMR (376 MHz, CDCI3) delta -80.7; HRMS (ESI+) calcd for C18H22F2N3O3S [M + H]+ 398.1344, found 398.1345 (Delta = -0.03 ppm).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Difluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; OJIMA, Iwao; ALFORD, Vincent; KAMATH, Anushree; CAO, Jian; REN, Xiaodong; SAMPSON, Nicole; AWWA, Monaf; (63 pag.)WO2018/175670; (2018); A1;,
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