Author: Jessica.F

Electric Literature of 36805-97-7, 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 36805-97-7 as follows.

A solution of 4-carboxybenzaldehyde (15A) (0.35 g, 2.1 mmol) in toluene (9 mL) was heated to reflux and N,N-dimethylformamide di-tert-butyl-acetal (3.8 mL, 16.0 mmol) was added over 25 minutes. After the addition was complete, the reaction was stirred at reflux for an additional hour then cooled to room temperature. The reaction mixture was washed sequentially with water, 5% aqueous NaHCO3, and brine. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo to provide compound 16A, which was used without further purification (0.37 g, 45%).

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; WO2008/130584; (2008); A1;,
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Related Products of 6358-77-6, These common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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.

Step 1. Synthesis of 1 -(5-bromo-2-methoxyphenyl)-5-methyl-1 H-pyrazole (C14). Boron trifluoride-tetrahydrofuran complex (777 g, 5.55 mol) was slowly added to a solution of 5-bromo-2-methoxyaniline (799.8 g, 3.96 mol) in 2-methyltetrahydrofuran (5.3 L), and the mixture was filtered through Celite. The filtrate was brought to a volume of 9 L with additional 2-methyltetrahydrofuran. In a separate container, tert-butyl nitrite (433 g, 4.20 mol) was dissolved in 2-methyltetrahydrofuran (8.0 L); the volume was then adjusted to 9 L by addition of 2-methyltetrahydrofuran. The two solutions were pumped by two Ismatec syringe pumps, both of which had been calibrated to deliver 15 mL/minute of 2-methyltetrahydrofuran, into a T-mixer connected to a 240 ml_ polytetrafluoroethylene (PTFE) coil for diazonium salt formation. At a combined flow rate of 30 mL/minute, the reaction mixture had a total residence time of 8 minutes in the coil to facilitate complete diazonium salt formation. The syringe pumps were started simultaneously, and the material was passed through the coil into a two-stage continuous flow stirred-tank reactor, where the 5-bromo-2-methoxybenzenediazonium tetrafluoroborate product (C12) was continuously extracted into water, using a water pump with a flow rate of 20 to 22.5 mL/minute. The aqueous layer was continuously separated in a stand pipe decanter, and then quenched into a jacketed 20 L reactor containing a mixture of tin(ll) chloride dihydrate (2.28 kg, 12.0 mol), 2- methyltetrahydrofuran (4 L) and water (4 L) at zero C. When the reduction had provided complete conversion to (5-bromo-2-methoxyphenyl)hydrazine (C13), as monitored by HPLC analysis, a solution of (3E)-4-(dimethylamino)but-3-en-2-one (454 g, 4.01 mol) in 2-methyltetrahydrofuran (3.0 L) was charged, and the jacket temperature was adjusted to 20 C. After 14 hours, analysis of the organic layer indicated that hydrazine C13 had been consumed. The layers were separated, and the organic layer was washed with aqueous sodium hydroxide solution (6 N, 2 x 5 L). Silica gel (1 .0 kg) was added to the organic phase, and the mixture was concentrated to dryness and dried at 35 C and 100 mbar vacuum on a rotary evaporator until a free-flowing powder was obtained. This powder was loaded onto a pad of silica gel (100 g), and elution was carried out with 2- methyltetrahydrofuran (6 L); the eluant was concentrated in vacuo to provide the product as a thick dark red oil. 1H NMR data indicated that this material was comprised of a roughly 9:1 ratio of the title product and the regioisomeric pyrazole. Yield: 573 g, 2.15 mol, 67% (corrected for 80% purity of starting 5-bromo-2-methoxyaniline). GCMS m/z 266, 268 (M+). 1H NMR (400 MHz, CDCI3) title product peaks only: delta 7.60 (d, J=1 .8 Hz, 1 H), 7.52 (dd, half of ABX pattern, J=8.7, 2.4 Hz, 1 H), 7.49 (d, half of AB pattern, J=2.4 Hz, 1 H), 6.92 (d, J=8.7 Hz, 1 H), 6.16-6.18 (m, 1 H), 3.79 (s, 3H), 2.16 (br s, 3H).

Statistics shows that 5-Bromo-2-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 6358-77-6.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; WO2012/172449; (2012); A1;,
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These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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. SDS of cas: 1484-26-0

General Procedure: Aniline (10, 10 mmol), 2-chloroethanol (2 mL), CaCO3 (2.00 g, 20 mmol) and KI (10percent mmol) were added to 14 mL water and refluxed for 8 h. After filtration, the filtrate was extracted with EtOAc (14 mL.x.3), and the combined organic layers were washed with saturated NaCl (14 mL.x.2), dried over anhydrous Na2SO4, filtered and concentrated. Column chromatography afforded the desired product 11.

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

Reference:
Article; Lin, Song-Wen; Sun, Qi; Ge, Ze-Mei; Wang, Xin; Ye, Jia; Li, Run-Tao; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 940 – 943;,
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Reference of 109-85-3, 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. 109-85-3, name is 2-Methoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2, 3 a-Dichloro provided 1, 4 a-napthoquinone 1g (4. 4mmol) diethylether 30 ml a melting solution 2 a-Methoxyethylamine 568 micro l (6. 6mmol), triethylamine 610 micro l some excellent. 24 hours at room temperature then evaporated in pressure with respect to the stirring mixture. (Hexanes: EtOAc=20:1) column chromatography compound to a positive number (NQ 25) to compounds of formula 25 to obtained.Yield: 53%

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

Reference:
Patent; Chosun University Industry-Academic Cooperation Foundation; Cho, Hoon; (48 pag.)KR101761848; (2017); B1;,
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Synthetic Route of 37466-89-0, 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. 37466-89-0 name is 3-Methoxybenzene-1,2-diamine, 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.

13.1 r3-(2-Amino-3-methoxy-phenylcarbamoyl)-propyll-methyl-carbamic acid benzyl esterTo a solution of 1.40 g 4-(benzyloxycarbonyl-methyl-amino)-butyric acid (obtained from 4- (methylamino)butyric acid and benzylchloroformate) in 25 mL THF were added 2.9 mL of DIPEA, 0.97 g of HOBt and 1.38 g EDC. After stirring for 5 min 0.80 g of 3-methoxy- benzene-1 ,2-diamine were added and the mixture was stirred for 3 h at rt. Sat. aq. NaHCOs solution was added, the phases were separated and the organic phase was washed with brine. The combined organic phases were dried over MgSO4, and concentrated in vacuo.LC-MS (A): tR = 0.80 min; [M+H]+: 372.27.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxybenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; RENNEBERG, Dorte; WO2010/46855; (2010); A1;,
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Reference of 1579-40-4, The chemical industry reduces the impact on the environment during synthesis 1579-40-4, name is Di-p-tolyl Ether, I believe this compound will play a more active role in future production and life.

Prior to use, NBS was recrystallized from water and the carbon tetrachloride was bubbled with nitrogen, stirred for 45 min with sodium sulfate, and checked by 1H-NMR spectroscopy. To a stirred solution of 4,4′-oxybis(methylbenzene) (28) (5.0 g, 25.2 mmol, 1 eq.) and NBS (8.98 g, 50.4 mmol, 2 eq.) in carbon tetrachloride (125 mL) under nitrogen was added a catalytic amount of AIBN. The reaction mixture was heated to 80-90 C (reflux) and stirred for 6.5 h. The solution was then cooled and the succinimide was removed on a sintered glass filter funnel. The solvent was removed in vacuo to yield the desired product 29 as beige crystals (8.3 g, 93%). A portion (1.82 g) was purified by flash chromatography (10:1 hexane:EtOAc) to yield 29 as white crystals: mp 85-86 C (lit.29 mp 93-95 C). 1H NMR (CDCl3): delta 7.38 (d, 4H), 6.98 (d, 4H), 4.52 (s, 4H).

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, Di-p-tolyl Ether, other downstream synthetic routes, hurry up and to see.

Reference:
Article; McGowan, Meredeth A.; Perreault, Denise M.; Thornton, Nancy B.; Garaas, Sarah D.; Gribble, Gordon W.; Arkivoc; vol. 2018; 5; (2018); p. 334 – 347;,
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Adding a certain compound to certain chemical reactions, such as: 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)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 175278-17-8, Formula: C7H5BrF3NO

General procedure: 1,1-Cyclopropanedicarboxylic acid (5) (12.0 g, 15.4 mmol) was dissolved in anhydrous THF (50 mL). Then triethanolamine (2.0 mL,13.9 mmol) was added to the mixture and the mixture was stirred on the ice-bath for 30 min. SOCl2 (1.2 mL, 16.66 mmol) was then added. Stirring was continued for 2h, a solution of 3,5-dimethylaniline 6 (3.6 g, 15.4 mmol) in anhydrous THF (10 mL) was added and continued stirring for 2h, after that, the ice bath was removed, and the mixture was stirred at room temperature overnight. After the completion of the reaction, the mixture was filtered and concentrated in vacuo. The residues was purified by silica gel flash chromatography (PE/AcOEt = 5:1) to yield 7 as white solid (0.8 g, 30.7%).

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, 2-Bromo-4-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Chuansheng; Shan, Yuanyuan; Sun, Ying; Si, Ru; Liang, Liyuan; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 506 – 518;,
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Related Products of 588-63-6, 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. 588-63-6, name is (3-Bromopropoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.3 g (0.00089 mol) of N- [ (3R)-1-azabicyclo [2.2. 2] [OCT-3-YL]-9H-XANTHENE-9-CARBOXAMIDE] (Example 31) were dissolved in 6 [ML] of THF. To this solution 0.21 ml (0.287g, 0.001335 mol) of [(3-BROMOPROPOXY)] benzene were added. The mixture was refluxed during 4 hours and then stirred 17 h at room temperature. The reaction mixture was filtered and the solid obtained washed with ether several times and dried. 0.48 [G] (98percent) of the title product were obtained. m. p.: 278.5-279. [2C] [MS [M-BR] + :] 469 [APOS;H-NMR] (DMSO-d6) : [S] 1.80-2. 0 (m, 3H), 2.05-2. 30 (m, 4H), 3.15-3. 25 (m, [1H),] 3.30-3. 65 (m, 6H), 3.82 (m, [1H),] 4.05 (t, 2H), 4.10 (m, [1H),] 5.05 (s, [1H),] 6.90-7. 0 (m, 3H), 7.05-7. 20 (m, 4H), 7.25-7. 42 (m, 6H), 9.01 (d, [1H,] NH).

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, (3-Bromopropoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMIRALL PRODESFARMA S.A.; WO2004/5285; (2004); A1;,
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Electric Literature of 321-28-8, A common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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.

Under ice bath conditions,6.38 g (48 mmol) of aluminum trichloride and 40 mlDichloromethane is put into a 100ml round bottom flask, stirred and dissolved4.68 g (60 mmol) of acetyl chloride, maintaining the temperature at 5 to 10 C., stirring at 5 C. for 10 minutes, followed by dropwise addition of 2-fluoroanisole 5.04 g(40 mmol). The mixture is stirred at 5C for 1 hour and then poured into 100 ml of ice-water. The aqueous layer is extracted with dichloromethane (2 x 30 ml). The combined organic phases are washed with water (2 x 30 ml), dried over anhydrous magnesium sulphate, filtered, and petroleum ether is used. The product was recrystallized from ethyl acetate in 92.4% yield.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northeast Agricultural University; Zhang Xiuying; Yang Hongliang; (11 pag.)CN107686465; (2018); A;,
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Related Products of 102-52-3, 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. 102-52-3 name is 1,1,3,3-Tetramethoxypropane, 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.

A solution of 1,1,3,3-tetramethoxypropane (23) (10 g) and concentrated HCl (0.43 mL) in H2O (11 mL) was stirred at room temperature for 10 min. Br2 (3.1 mL) was added dropwise to the solution at room temperature for more than 50 min. The reaction mixture was stirred at room temperature for 20 min and concentrated in vacuo. The residual solid was washed with H2O to give 24 (3.6 g, 39%) as a yellow solid. Mp 147-148 C; 1H NMR (CDCl3) delta 4.73-4.80 (1H, m), 8.47 (2H, br s); FAB MS m/e (M-H)- 149.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1,3,3-Tetramethoxypropane, and friends who are interested can also refer to it.

Reference:
Article; Inoue, Takayuki; Morita, Masataka; Tojo, Takashi; Yoshihara, Kousei; Nagashima, Akira; Moritomo, Ayako; Ohkubo, Mitsuru; Miyake, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1219 – 1233;,
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