Tag: M.W=100-200

Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.

General procedure: The reaction mixture containing 0.5 g (1.8 mmol) of 4-(dibromomethyl)benzenecarbaldehyde (7), 0.11 g (0.0018 mmol) of isopropylamine (12) and 0.2 g of molecular sieves 3 A in 10 mL of dry benzene was thermostated at room temperature for 24 h. N-Isopropyl-4-(dibromomethyl)benzenecarbimine (14) (0.44 g, 77%) in the form of yellow oil was obtained by filtration through the molecular sieves followed by the removal of the solvent in vacuo provided by water jetpump.

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

Reference:
Article; Gazizov; Ivanova, S. Yu.; Karimova; Bagauva; Gazizova; Karimova; Russian Chemical Bulletin; vol. 65; 1; (2016); p. 191 – 194; Izv. Akad. Nauk, Ser. Khim.; 1; (2016); p. 191 – 194,4;,
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Application of 707-07-3, 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 707-07-3 as follows.

4-Methylbenzenesulfonic acid (3.1 g, 16 mmol) was converted to N1-benzyl-4-bromobenzene-1,2-diamine (45 g, 160 mmol).And 500 mL of dichloromethane and o-trimethyl benzoate30 mL is added to the mixed solution and reacted for about 40 hours at room temperature under nitrogen. After the reaction was completed, the organic layer was concentrated under reduced pressure, washed with 40% methanol / water and sodium hydrogencarbonate / water, and dried to obtain a product. (22.3 g, yield 40%)

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SFC Ltd.; Ryu Se-jin; Sim So-yeong; Lee Sang-hae; (51 pag.)KR102030388; (2019); B1;,
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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. 103-50-4, name is Benzyl ether, A new synthetic method of this compound is introduced below., Recommanded Product: 103-50-4

6-{2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester (4). Substantially monodispersed benzyl ether 3 (1.03 g, 2.0 mmol) was dissolved in 25 ml ethanol. To this solution was added 270 mg 10% Pd/C, and the mixture was placed under a hydrogen atmosphere and stirred for four hours, at which time TLC showed the complete disappearance of the starting material. The reaction mixture was filtered through Celite 545 to remove the catalyst, and the filtrate was concentrated in vacuo to yield the monodispersed compound 4 as a clear oil (0.67 g, 79%). FAB MS: m/e 425 (M+H), 447 (M+Na).

The synthetic route of 103-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nobex Corporation; US6867183; (2005); B2;,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., name: (4-(Trifluoromethoxy)phenyl)methanamine

To a solution of lithium 1 -methyl-3 -(4-methyl-piperazin- 1 -yl)- lH-indazole-6- carboxylate (88mg, 0.32 mmol) in anhydrous DMF (5mL) was added EDC (73mg, 0.38mmol) and etaOBt (51mg, O.38mmol). The mixture was stirred for 10 min. then Et3N (0.1 ImL, 0.80mmol) and 4-trifluoromethoxybenzylamine (O.O58mL, 0.38 mmol) were added. The mixture was heated at 50 0C for 15 hr. The mixture was allowed to cool, diluted with ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate (25 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography on silica yielded the title compound (28mg, 20%). m/z (M+eta) = 448.46

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 93919-56-3.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61109; (2008); A2;,
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5961-59-1, name is 4-Methoxy-N-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. Computed Properties of C8H11NO

An activated carbon supported platinum catalyst (Pt / C, 0.06 mg platinum, 0.0003 mmol, 0.1 mol%) was added to a 10 mL Schlenk tube,After evacuation of argon, add 1 mL of solvent (toluene).Under argon protection, to the above system,Separately, phenylsilane (78.9 mg, 0.75 mmol) was added successively,III-3 (R2 = p-methoxyphenyl, R3 = methyl) (41.2 mg, 0.3 mmol) and formic acid (27.6 mg, 0.6 mmol).The reaction was carried out at 80 C with stirring for 15 hours.After completion of the reaction, 3 mL of ethyl acetate was added to the system,The reaction was quenched with aqueous sodium hydroxide (3 mol / L, 3 mL)Ethyl acetate (3 x 10 mL), the organic phase was separated,Dried over anhydrous Na2SO4, filtered,The solvent was removed by rotary evaporation.The residue was purified by column chromatography on ethyl acetate / petroleum ether = 1: 100 mixed solvent,The product was isolated and purified to give the target product IV-333.6 mg in 74% yield.

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hubei Engineering College; Zhu Lei; Wang Liansheng; Li Bojie; Li Wei; Fu Boqiao; (21 pag.)CN106892826; (2017); A;,
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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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1836-62-0

Example 1 Preparation of Carvedilol in Neat Conditions 2-(2-Methoxyphenoxy)ethylamine (III) (4.89 g) was heated to about 100 C., after which 4-(oxiran-2-ylmethoxy)-9H-carbazole (II) (3.31 g) was added portionwise. After approximately 20 minutes, the reaction mixture was cooled to about 70 C., after which water (25 ml) and ethyl acetate (15 ml) were added. The pH of the two-phase mixture was then adjusted to 5 with 2 N hydrochloric acid. The solid that formed, Carvedilol hydrochloride hydrate, is filtered, washed with water (20 ml) followed with ethylacetate (15 ml). The resulting material is reslurried in ethylacetate (50 ml) and water (20 ml) containing 5% Sodium carbonate until the pH reached 7.5. The organic phase was separated and dried over sodium sulfate. The dried solution was concentrated to a turbid solution and cooled overnight to about 4 C. Precipitated carvedilol was isolated by filteration and crystallized from isopropanol.

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 1836-62-0.

Reference:
Patent; Hildesheim, Jean; Finogueev, Sergey; Aronhime, Judith; Dolitzky, Ben-Zion; Ben-Valid, Shoshana; Kor, Ilan; US2002/143045; (2002); 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. 7664-66-6, name is 4-Isopropoxyaniline, A new synthetic method of this compound is introduced below., name: 4-Isopropoxyaniline

A mixture of 4-bromo-2-fluoro-l-nitrobenzene (0.39, 1.36 mmol), 4-(propan-2-yloxy)aniline (0.229,1 .43 mmol) and K2C03 (0.38 g, 2.73 mmol) in DMF (3 mL) was stirred at 90 C for 5h. Then thereaction mixture was diluted with EtOAc and washed with 5% aq. LiCI solution. The organic phasewas dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by SiC2 columnchromatography (hexanes I EtOAc from 30:1 to 20:1) to give 0.43g (90%) of the product as orangesolid.1H NMR (500 MHz, CDCI3) O 9.37 (5, 1H), 8.04 (d, 1H), 7.12-7.17 (m, 3H), 6.93-6.97 (m, 2H), 6.81 (dd, 1H), 4.56 (sep, 1H), 1.36 (d, 6H).

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; ARISAN THERAPEUTICS INC.; PLEWE, Michael; BROWN, Eric; GANTLA, Vidyasagar; HENKEL, Gregory; MCCORMACK, Kenneth; SOKOLOVA, Nadzeda V.; SHIN, Young-Jun; (147 pag.)WO2018/13430; (2018); A2;,
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Electric Literature of 24332-20-5, These common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, 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 2 Concentrated hydrochloric acid (0.84 ml) was added to a stirred mixture of 2-methoxyacetaldehyde dimethyl acetal (12.6 g) and water (59 ml) and the resultant solution was heated to 40 C. for 2 hours. The solution was cooled to ambient temperature and basified to pH8 by the addition of a saturated aqueous sodium bicarbonate solution. The mixture so obtained was added to a stirred suspension of 6-amino-4-(3′,4′-difluoroanilino)quinazoline hydrochloride (6.4 g) in a mixture of glacial acetic acid (1.26 g) and ethanol (750 ml). Sodium cyanoborohydride (2.64 g) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained 4-(3′,4′-difluoroanilino)-6-(2-methoxyethylamino)quinazoline (5.2 g, 69%), m.p. 150-153 C.; NMR Spectrum: (CD3 SOCD3 +CD3 CO2 D) 3.33 (s, 3H), 3.43 (t, 2H), 3.63 (t, 2H), 7.5 (m, 5H), 7.96 (m, 1H), 8.56 (s, 1H); Elemental Analysis: Found C, 61.1; H, 4.9; N, 16.5; C17 H16 F2 N4 O 0.2H2 O requires C, 61.1; H, 4.95; N, 16.8%.

The synthetic route of 24332-20-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; US5942514; (1999); 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. 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, A new synthetic method of this compound is introduced below., 494-99-5

Then, 0.6 mol of the thus-obtained compound (VI-2) was dissolved in a 3.5-fold amount by weight, based on (VI-2), of carbon tetrachloride, and 0.66 mol of bromine gas was blown thereinto under reflux condition while irradiating with a mercury vapor lamp. The blowing was completed in 16 hours. After completion of the reaction, the solvent was distilled off to obtain 3,4-dimethoxybenzyl bromide (VII-2) in 92% yield.

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; Sumitomo Chemical Company, Limited; US4335263; (1982); A;,
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Reference of 366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 4a (see general route 4, procedure H, M and K)2-(3-fluoro-4-methoxyphenyl)hydrazine; [00257] A room temperature solution of 3-fluoro-4-methoxyaniline (25.0 g, 177 mmol) in concentrated 12M aqueous hydrochloric acid solution (60 mL) was stirred for two hours, after which it was cooled to 0°C to which a solution of sodium nitrite (14.2 g, 205 mmol), in water (50 mL), was added, drop-wise over 45 minutes, with internal temperature monitoring such that the reaction temperature does not warm above 5°C. After stirring for one hour at 0°C, the reaction mixture was poured slowly into a 0°C pre-made solution of tin(II) chloride dihydrate (168 g, 744 mmol) in concentrated 12M aqueous hydrochloric acid solution (125 mL). The reaction mixture was allowed to warm up to room temperature, after which it was stored in the freezer overnight (12 hours), leading to the formation of a precipitate. This dark brown solid was successively washed with water (2 x 100 mL) and diethyl ether (3 x 100 mL), and dried to afford crude 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as a pasty brown solid (note that this crude solid can also be used directly in the next step). As part of the purification and isolation process, the crude hydrazine hydrochloride salt was reconstituted in water (100 mL) and 3M aqueous sodium hydroxide solution (200 mL), extracted with diethyl ether (2 x 200 mL), washed with successively with saturated sodium bicarbonate solution (2 x 100 mL), water (2 x 20 mL) and saturated sodium chloride solution (2 x 20 mL), dried (sodium sulfate), filtered and concentrated to afford 2-(3-fluoro-4- methoxyphenyl)hydrazine as a light yellow solid (15.0 g, 96.1 mmol, 54percent yield. 1H NMR (400 MHz, CDC13) delta (ppm): 6.87 (m, 1H), 6.66 (dd, 1H), 6.49-6.53 (m, 1H), 5.06 (br. s, 1H), 3.83 (s, 3H), 3.55 (br. s, 2H).[00258] A portion of 2-(3-fluoro-4-methoxyphenyl)hydrazine (5.00 g, 32.0 mmol) was dissolved in absolute ethanol (50 mL), to which a solution hydrogen chloride (15 mL, 2.5M in ethanol) was added. The resulting precipitate was filtered, washed with ethyl acetate (2 x 40 mL), and dried to afford 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as an off- white solid (4.7 g).

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

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
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