Author: Jessica.F

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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H11BrO2

a sealed flask, 3,6-dichloro-4-methylpyridazine (27 g, 161 mmol) was suspended in aqueous ammonia (25%, 300 mL). The reaction mixture was heated at 110 C. for 48 hours (turned into solution after 1 hour). After cooling to room temperature, the reaction was poured into CH2Cl2, and the organic phase was separated, dried over Na2SO4, and concentrated under vacuum, to give 22.4 g of 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine as a mixture of regioisomers which were used directly in the next step.The mixture of regioisomers 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine (22.4 g) was suspended in 2-propanol (300 mL). 1-bromo-2,2-dimethoxypropane (36.0 g, 26.6 mL, 193 mmol, 1.2 eq.) and PPTS (2.96 g, 11.6 mmol, 0.0725 eq.) were added, and the resulting solution was heated at 105 C. overnight. The solvent was removed in vacuo and the residue was taken up in CH2Cl2 and washed with NaHCO3. The organic phases were dried over Na2SO4, concentrated in vacuo and the crude light brown solid was chromatographed (EtOAc/Heptane 1/2-1/1) to give separately 6.1 g of 6-chloro-2,8-dimethyl-imidazo[1,2-b]pyridazine MS m/z 182.1 [M+H]+(21%) as a white solid and 5.9 g of 6-chloro-2,7-dimethyl-imidazo[1,2-b]pyridazine MS m/z 182.1 [M+H] (20%) 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:
Patent; Hoffmann-La Roche Inc.; PTC Therapeutics, Inc.; Ratni, Hasane; Green, Luke; Weetall, Maria L.; Naryshkin, Nikolai A.; (33 pag.)US2019/315773; (2019); 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. 6738-23-4, name is 2,4-Dimethylanisole, A new synthetic method of this compound is introduced below., Formula: C9H12O

Step A: Preparation of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide To a solution of 2.72 g. (0.02 mole) of 2,4-dimethylanisole in 20 ml. of acetic acid and 2 ml. of sulfuric acid was added (2.47 g., 0.02 mole) 2-chloro-N-(hydroxymethyl)acetamide at <20 C. over a 10 minute period with stirring. After standing at room temperature about 20 hours the mixture was poured with stirring into 250 ml. of ice-water. After 1 hour the precipitate was collected, washed with water and dried at 60 C. and recrystallized 3 times from methanol:water (3:2), once from ethanol:water (3:2) and twice from ethanol:water (1:1) to give 0.34 g. of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide, m.p. 124-124.5 C. 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; Merck & Co., Inc.; US4070464; (1978); A;,
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Some common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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. Quality Control of 2-Bromo-1,1-dimethoxyethane

[000321] A mixture of 4-chlorophenol (10 g, 78 mmol), 2-bromo-l,l- dimethoxyethane(13.1 g, 78 mmol), K2C03 (14 g, 101 mmol), KI (100 mg) in DMF (50 mL) was stirred at reflux for 3 h. The mixture was cooled to rt and filtered. The filtrate was added water (200 mL), extracted with ethyl acetate (100 mL x 2), washed with water (100 mL x 3), brine (100 mL x 1), dried over Na2S04, concentrated, and purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to yield Compound 11A (15 g, yield 89 %) as a colorless liquid. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 3.45 (s, 6H), 3.96 (d, J= 5.2 Hz, 2H), 4.70 (t, J= 5.6 Hz, 1H), 6.85 (d, J= 8.8 Hz, 2H), 7.21 (d, J= 8.8 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7252-83-7, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); 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. 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(2-Chloroethoxy)acetic acid

1.39 g (10.0 mmol) 2-(2-chloro-ethoxy)-acetic acid are heated to 60¡ã C. for 1 h with 1 drop of DMF in 8.0 ml of thionyl chloride and then evaporated down completely i. vac. The residue is added in 5 ml THF to a mixture of 1.18 g (10.0 mmol) 4-amino-benzonitrile and 4.5 ml (32.5 mmol) TEA in 20 ml THF at 0¡ã C. and rinsed with 5 ml THF. Then the mixture is stirred for 16 h at ambient temperature. After evaporation i. vac. the residue is combined with ethyl acetate, washed with 2N hydrochloric acid and sat. sodium hydrogen carbonate solution and dried on sodium sulphate. After evaporation i. vac. the residue is purified by chromatography on silica gel (eluant gradient: petroleum ether/ethyl acetate=6:1–>3:1). Yield: 1.82 g (76percent) Rf value: 0.43 (silica gel, petroleum ether/ethyl acetate 1:1) C11H11ClN2O2 (238.67) Mass spectrum: (M-H)-=237/239 (chlorine isotopes); (c) 2-(2-chloro-ethoxy)-acetic acid-chloride13.86 g (100 mmol) 2-(2-chloro-ethoxy)-acetic acid are combined with 15 ml (207 mmol) thionyl chloride at ambient temperature and 3 drops of DMF are added. The mixture is stirred for 16 h at 60¡ã C. Then it is evaporated down i. vac., the residue is distilled i. vac. and the overflow is collected at 75-78¡ã C.Yield: 12.90 g (82percent)C4H6Cl2O2 (157.00)Mass spectrum: (M+H)+=157/159/161 (chlorine isotopes)

The synthetic route of 14869-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
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Electric Literature of 13940-96-0, These common heterocyclic compound, 13940-96-0, name is 4-Phenoxybenzene-1,2-diamine, 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.

For preparing the 3,4-diamino-diphenyl ether used as starting material, 172.5 g of 5-chloro-2-nitro-aniline were heated for 4 hours under reflux in 500 ml of dimethylformamide with 94 g of phenol in the presence of 150 g of anhydrous potassium carbonate. After cooling, the reaction mixture was diluted with 1000 ml of water, the 3-amino-4-nitro-diphenyl ether that had precipitated was filtered off with suction and purified by recrystallization from isopropanol. Yield: 110 g; melting point: 142C. 103 g Of the 3-amino-4-nitro-diphenyl ether so obtained were hydrogenated in 800 ml of dimethylformamide with Raney nickel under a pressure of 100 atmospheres gauge at room temperature, the catalyst was then removed by filtration and the solution was evaporated under reduced pressure. The 3,4-diamino-diphenyl ether that had formed was obtained in the form of a sirupy mass which was dissolved in ethanol and used in the reaction as described above.

The synthetic route of 13940-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US3954791; (1976); A;,
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Electric Literature of 37466-89-0, 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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Methoxybenzene-1,2-diamine dihydrochloride (Example 54(a)) was partitioned between 10% aq. Na2CO3 and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2¡Á). The combined organic extracts were dried over Na2SO4, filtered and evaporated to yield 3-methoxybenzene-1,2-diamine. A mixture of the diamine (912 mg, 6.6 mmol) and diethyl oxalate (9.0 mL, 66 mmol, Aldrich) was heated at 185 C. for 18 h. The reaction mixture was left to reach room temperature and the solid precipitate was filtered. The filter cake was washed with EtOH and dried in vacuo to give the title compound. MS (ESI, pos. ion.) m/z: 191 (M+1).

The synthetic route of 3-Methoxybenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Hui-Ling; Balan, Chenera; Doherty, Elizabeth M.; Falsey, James R.; Gore, Vijay Keshav; Katon, Jodie; Norman, Mark H.; US2005/176726; (2005); A1;,
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20265-97-8, name is 4-Methoxyaniline hydrochloride, 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. category: ethers-buliding-blocks

General procedure: A cold solution of aryldiazonium salt (2.0 mmol) was preparedby adding a solution of NaNO2 (2.2 mmol, 0.15 g into 1.0 mL H2O) toa cold solution of arylamine hydrochloride (2.0 mmol of arylaminein 1.5 mL conc. HCl). The resulting solution of aryl diazonium saltwas added drop wise to a mixture of compound (II) (2.0 mmol,0.43 g) in water (15 mL) containing NaOH (25 mmol, 1.0 g) at0e5 C. The pH of the reaction mixture was maintained at 9e10 byadding 2.5% sodium hydroxide solution. Then, the reaction mixturewas stirred for 2 h at the same temperature and the precipitate wasfiltered off and the resulting solid was washed with cold ethanoland dried at 50 C in an oven. The crude product was purified usingthe recrystallization method as mentioned in Table 1. Under thesame reaction conditions, a series substituted arylazo quinolonedyes were obtained in satisfactory yields (Table 1, Scheme 2).

The synthetic route of 20265-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rufchahi, E.O. Moradi; Gilani, A. Ghanadzadeh; Taghvaei; Karimi; Ramezanzade; Journal of Molecular Structure; vol. 1108; (2016); p. 623 – 630;,
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These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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. HPLC of Formula: C8H8Br2O

A mixture of B32.1 (4.3 g, 25mmol), CH3SNa (6.12 g, 4Smmol) in DMF (50 mL) was heated at 90 C for 18 h. DCM (50 mL) and water (100 mL) was added. The organic phase was separated andconcentrated to give the title compound (2.9 g, 80%). The crude product was used in the next step without further purification.

The synthetic route of 1-Bromo-4-(2-bromoethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (148 pag.)WO2017/221100; (2017); A1;,
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Application of 1978-39-8,Some common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-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.

A solution of sodium nitrite (36 g, 0.51 mole) in water (50 mL) was slowly added to a solution of 5-fluoro-2-methoxy-phenylamine (61.5 g, 0.48 mol) in hydrochloric acid (20 % aqueous solution, 115 mL) at 0 C. After stirring for 10 minutes, a cooled (0 C) solution of acrolein (50 mL, 0.75 mol) in acetone (100 mL) containing calcium oxide (0.56 g, 0.010 mol) was added slowly to the reaction mixture. This was then followed by a solution of cuprous chloride (5 g, 0.05 mol) in acetone (100 mL) containing hydrochloric acid (20 % aqueous solution, 10 mL). The mixture was stirred at 0 to 30 C for 3 hours, and then extracted three times with dichloromethane (300 mL). The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give a black viscous oil. The crude product was passed through a short silica column to give the crude product, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Fluoro-2-methoxyaniline, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CLEVELAND, Thomas; MAKINGS, Lewis R.; HAMILTON, Matthew; GROOTENHUIS, Peter D.J.; WO2005/26137; (2005); A2;,
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Application of 1758-46-9, A common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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.

Intermediate 73: (6-BROMO-PYRIDIN-3-YLMETHYL)- (2-PHENOXV-ETHYL)-AMINE A solution of 2-bromo-pyridine-5-carbaldehyde (500MG, 2. 69MMOL) and 2- (PHENOXY)- ethylamine (594mg, 4.3mmol) in anhydrous ethanol (14ML) was stirred at room temperature for 7 hours. Sodium borohydride (102mg, 2. 7MMOL) was then added to the solution, and the resultant mixture was allowed to stir for a further 3 hours before being quenched with water. The resultant mixture was concentrated, to provide (6-BROMO- pyridin-3-ylmethyl)- (2-phenoxv-ethvl)-amine (quantitative), which was’used without further purification. LCMS (Method B): RT = 1. 79 minutes; 307 309 (M+H) +.

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; ARGENTA DISCOVERY LIMITED; WO2005/14588; (2005); A1;,
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