Month: September 2021

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. 4179-19-5, name is 3,5-Dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,5-Dimethoxytoluene

Step 1: 4-(2,4-Dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid[0423] To a suspension of l,3-dimethoxy-5-methyl-benzene (5.1O g, 33.55 mmol) and succinic anhydride (3.69 g, 36.91 mmol) in nitrobenzene (100 mL) was added AlCl3 (8.9 g, 67.10 mmol). The reaction mixture was stirred at room temperature for 16 hours then carefully poured into aqueous NaOH. The pH was adjusted to 10 with solid NaOH and the aqueous solution washed with dichloromethane. The pH of the aqueous solution was adjusted to 3 with concentrated HCl and extracted with EtOAc. The organic extracts were dried and concentrated in vacuo. The residue was triturated dichloromethane to give 4-(2,4-dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid as a pale yellow solid (3.7 g, 43%). 1H NMR (400 MHz, MeOD-d4) delta 6.44 (s, IH), 6.40 (s, IH), 3.80 (s, 3H), 3.78 (s, 3H), 3.03 (t, J = 8.1 Hz, 2H), 2.60 (t, J = 8.1 Hz, 2H), 2.19 (s, 3H).

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 4179-19-5.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
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These common heterocyclic compound, 64465-53-8, name is 4-Fluoro-3-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. Computed Properties of C7H8FNO

Aqueous hydrobromic acid (48%, 2.41 mL) was added to 4-fluoro-3-methoxyaniline (1.0 g, 7.1 mmol) in water (10 mL) and the resulting mixture was cooled to 0 C in an ice bath. A solution of sodium nitrite (538 mg, 7.8 mmol) in water (5 mL) was added dropwise during 15 min while maintaining the temperature between 0-5 0C. The resulting diazoniumsalt solution was added to a suspension of copper(I) bromide (1.12 g, 7.8 mmol) in water (5 mL) which had been pre-heated to 75 C. The mixture was shaken thoroughly, aqueous hydrobromic acid (48%, 12.07 mL) was added and the solution was stirred at ambient temperature for 16 h. Excess water was added and the product was extracted with diethyl ether and the combined organic extracts were washed with aqueous saturated sodium chloride, dried over magnesium sulfate, filtered and the solvent was evaporated in vacuo to give 1.02 g (70% yield) of the title compound.: 1H-NMR (DMSO-J6): delta 7.36 (dd, J= 7.78, 2.26 Hz, 1 H), 7.23-7.17 (m, 1 H), 7.14-7.09 (m, 1 H), 3.86 (s, 3 H); MS (EI) (m/z, %) 204,206 (100), 189,191 (23), 161,163 (45)

The synthetic route of 4-Fluoro-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/58602; (2007); A2;,
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Synthetic Route of 16452-01-0, 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. 16452-01-0, name is 3-Methoxy-4-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 47 Part E. 4-Isothiocyanato-2-methoxy-1-methyl-benzene To a solution of 3-methoxy-4-methylaniline (50 mg, 0.36 mmol) in DCM (2 mL) was added thiocarbonyldiimizaole (68 mg, 0.38 mmol) and the mixture was stirred at rt for 3 h. The mixture was concentrated under reduced pressure, and the residue was dissolved in MeOH (3 mL) and filtered through an SCX cartridge (CUBX1HL, 500 mg cartridge, United Chemical Technologies, Bristol Pa., USA). The filtrate was concentrated under reduced pressure to afford the title compound which was used as such for the subsequent step without further purification.

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-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US6596747; (2003); B2;,
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Synthetic Route of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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 5-carbamoyl-2-fluoro-4-hydroxybenzene-1 -sulfonyl chloride (lnt-2, 1 .4 g) in DCM (15 mL) at 0 C was added pyridine (0.670 mL) followed by 4-isopropyxyaniline (0.696 mL). The reaction mixture was allowed to warm to RT and was stirred for 16 hr. The reaction mixture was poured into water (10 mL) and extracted with DCM (2 x 15 mL). The combined DCM extracts were washed with saturated brine (10 mL), dried over sodium sulfate and concentrated under reduced pressure to afford the crude product (900 mg). The crude product was purified by silica gel column chromatography, eluting with 30-40% EtOAc/petroleum ether to afford the titled compound (700 mg). LCMS m/z 369.09 (M+H)+. NMR (400 MHz, DMSO-c/6) delta ppm 1 .19 (d, J=5.92 Hz, 6 H) 4.36 – 4.56 (m, 1 H) 6.58 – 6.84 (m, 2 H) 6.84 – 7.10 (m, 3 H) 8.06 (br. s., 1 H) 8.31 (d, J=8.1 1 Hz, 1 H) 8.62 (br. s., 1 H) 10.06 (s, 1 H) 14.06 (br. s., 1 H).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
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Electric Literature of 7664-66-6, 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 7664-66-6 as follows.

Phenyl chloroformate (15.2 kg, 97.1 mol) was dissolved in toluene (115.7 kg) and cooled to 3 C. 4-isopro- poxyaniline (III) (13.3 kg, 88.0 mol) was mixed with acetonitrile (43.4kg) and slowly added to the phenyl chloroformate solution over 1 hour 40 minutes, followed by slow addition of triethylamine (9.8kg, 96.8 mol) over 46 minutes. The mixture was heated to 17.5C. and stirred for 3 hours 30 minutes until the reaction was deemed complete by HPLC. The product solution was washed with iN HC1, followed by removing acetonitrile though an azeotropic distillation with additional toluene (52.3 kg). The solution was heated to 58 C. before slowly adding heptane (43.7 kg) over 1 hour 2 minutes, after which the slurry was cooled to 23.5 C. over 2 hours 35 minutes and stirred for an additional 2 hours 51 minutes. The material was isolated, washed twice with heptane, and dried at 40 C. for 3 hours 49 minutes. The product was discharged, yielding 19.1 kg of the title compound (lIla) (80% yield, 100% purity HPLC AUC). ?H NMR (300 MHz, CD3OD, oe): 7.38 (m, 4H), 7.19 (m, 3H), 6.86 (d, J=9 Hz 2H), 4.52 (sept, J=6 Hz, 1H), 1.28 (d, J=6 Hz, 611).

According to the analysis of related databases, 7664-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Phamaceuticals, Inc.; Armitage, Ian; Ferdous, Abu J.; Bourland, Michael E.; Boyle, Craig S.J.; Cooper, Martin Ian; Langston, Marianne; US2015/133460; (2015); A1;,
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494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, 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. Product Details of 494-99-5

3,4-Dimethoxytoluene (7.6 g, 50 mmol),Sodium bromate (6.0g, 40mmol),Sodium Bromide (8.2g, 80mmol)And carbon tetrachloride (18mL),Add to stirReturn condenser,In the reaction flask of thermometer and tail gas absorption device,Heat to reflux,Slowly add 1/2 volume of sulfuric acid (60mmol of concentrated sulfuric acid is diluted with 2mL of water and added within about 1.5h).Followed by gas chromatography,After the substrate is fully involved in the reaction (about 1 h),Quickly add 1/3 volume of initiator solution (1.12g ABVN dissolved in 7mL carbon tetrachloride),After the emergence of a vigorous reflux system,Continue to slowly add the remaining sulfuric acid and initiator solution (approx. 4.5 hours later),Continue the reaction until the product is no longer formed or the byproduct is significantly increased (about 1.5 h),To room temperature,filter,The filtrate was washed with 10 ml of sodium bicarbonate solution (5%).Liquid separation,The organic phase is dried over anhydrous sodium sulfate.concentrate,The crude product was purified by recrystallization (ethyl acetate:petroleum ether=1:13, volume ratio) to give 2-bromo-4,5-dimethoxybenzyl bromide (13.08 g).Yield 85%.

The synthetic route of 494-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Normal University; Xiao Xiaohui; Chen Yufeng; (9 pag.)CN107417501; (2017); 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. 50868-73-0, name is 2-Methoxy-6-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Methoxy-6-methylaniline

Examples 9 and 10 2 g of 1,2,3,4-Tetrafluoroanthraquinone and 25 g of 2-methoxy-6-methylaniline were charged in a 50 cc, four necked flask and then the reaction was carried out at 80C for about 4 hours.. After completion of reaction, 2-methoxy-6-methylaniline was distilled out from the reaction solution, and a column purification using a column with a silica gel was effected to give rise to 1.04 g of 2-(2-methoxy-6-methylanilino)-1,3,4-trifluoroanthraquinone (Reference Dye 7′) (yield 36.7 mol%) and 1.05 g of 2,3-bis(2-methoxy-6-methylanilino)-1,4-difluoroanthraquinone (Dye 8) (yield 28.6 mol%).. The physical properties of Reference Dye 7′ and analytical values defining the compound are tabulated in Table 2 and the physical properties of Dye 8 and analytical values defining the compound are tabulated in Table 3.

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; NIPPON SHOKUBAI CO., LTD.; EP833203; (2004); B1;,
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Electric Literature of 6298-96-0, 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 6298-96-0 as follows.

A mixture of (1S)-1-(4-methoxyphenyl)ethanamine (7.6 g) and itaconic acid (6.5 g) was stirred at 130 C. for 1 hour. After cooling, chloroform was added to the reaction solution. The organic layer was washed with 1 N hydrochloric acid and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a stereoisomeric mixture (12.7 g) related to the 3-position of the title compound.

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; Takeda, Yasuyuki; Yoshikawa, Kenji; Kagoshima, Yoshiko; Yamamoto, Yuko; Tanaka, Ryoichi; Tominaga, Yuichi; Kiga, Masaki; Hamada, Yoshito; (132 pag.)US2016/46639; (2016); A1;,
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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 74654-07-2 as follows. name: 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine

3′-Amino-6 ‘- (tert-butoxycarbonylamino)Spiro [isobenzofuran-1 (3H), 9 ‘- [9H] xanthene]-3-one(100 mg, 0.23 mmol) was dissolved in dichloromethane (2.0 mL), 2,6-lutidine (0.11 mL, 0.93 mmol) was added and cooled to 0 C. Triphosgene (31 mg, 0.12 mmol) was added and stirred at 0 C. for 30 min,After further reacting at room temperature for 1 hour,[2- [2- (2-methoxyethoxy) ethoxy] ethyl] amine (105 mg, 0.46 mmol) was added and reacted as such for 1 hour.After diluting the reaction solution with ethyl acetate (100 mL)The organic layer was washed with 1 M hydrochloric acid (50 mL), saturated aqueous sodium hydrogen carbonate solution (50 mL)And saturated brine (50 mL) in this order, and dried over anhydrous sodium sulfate.The solvent was distilled off under reduced pressure,The obtained residue was purified by silica gel chromatography (chloroform,Then 50% ethyl acetate / chloroform) to giveSpiro [isobenzofuran-1 (3H), 9 ‘- [9H (3H), 3’ – [[2- [2- (2-methoxyethoxy) ethoxy] ethyl] aminocarbonylamino] ] Xanthen] -3-one (130 mg, yield 90%) as a yellow solid.

According to the analysis of related databases, 74654-07-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CD: Tosoh Corporation; Satoru: Sgami Chemical Research Institute; Inoe, So Sen; Araki, Hiroshi; Miki, Daisuke; Futami, Itaru; Saijou, Satoshi Bun; (65 pag.)JP2017/222609; (2017); A;,
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Related Products of 651734-54-2, 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.

[0230] A mixture of 2,4-dichloro-5-(iodomethyl)pyrimidine (1.50 g, 5.19 mmol), 2,6- difluoro-3,5-dimethoxyaniline (1.08 g, 5.71 mmol) in N,N-diisopropylethylamine (4 mL) was stirred at 80 C for 2 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel (eluting with 0- 40% EtOAc in DCM) to give 1.70 g of the desired product. LCMS calculated for C13H12C12F2N302 [M+Hj m/z: 350.0; Found: 350.0.

The synthetic route of 2,6-Difluoro-3,5-dimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; WU, Liangxing; SHEN, Bo; YAO, Wenqing; (114 pag.)WO2016/134294; (2016); A1;,
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