Tag: M.W=100-200

Related Products of 96606-37-0, 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 96606-37-0 as follows.

Example 7: Synthesis OF 3-AMINO-4-ETHOXY-6- (4-HYDROXY-PIPERIDIN-1-YL)- benzo [B] THIOPHENE-2-CARBOXYLIC acid amide To a solution of 1.0 g (6.4 mmol) of 2, 4,6-trifluorobenzonitrile in MEOH (35 mL) was added 0.65 g (6.4 mmol) of 4-hydroxypiperidine and 1.2 mL (6.7 mmol) OFF, N diiisopropylethylamine. The mixture was heated to 65 C FOR 4 h then cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.325 g (21 %) OF 2, 6-DIFLUORO-4- (4-HYDROXY- PIPERIDIN-L-YL)-BENZONITRILE as a white solid.

According to the analysis of related databases, 96606-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/12283; (2005); A1;,
Nitrile – Wikipedia,
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Application of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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 reaction container was charged with 70 g of commercially available 4-cyano-3-trifluoromethylaniline (LC surface percentage: 99.39%) and 350 mL of ethanol, and the temperature was increased to 72C. After the mixture was stirred at 72 to 75C for 30 minutes, insoluble matters were removed by filtration at the same temperature and the mixture was further washed with 10 mL of ethanol. The filtrate thus obtained was cooled to 57C, and 360 mL of water was dropped at the same temperature over about 4 hours. 30 mg of 4-cyano-3-trifluoromethylaniline that had been previously purified was seeded thereto and the resultant mixture was cooled to 45C, and thereafter stirred at the same temperature for 30 minutes. Then, the mixture was cooled to 25C and stirred at the same temperature for 1 hour. Crystals were separated by filtration and washed with a mixed solvent of 56 mL of ethanol and 56 mL of water to give 83.81 g of wet crystals. The wet crystals were dried under reduced pressure to obtain 50.61 g of 4-cyano-3-trifluoromethylaniline. The LC surface percentage was 99.90%, and the yield was 72.3%. A reaction container was charged with 68 mL of N,N-dimethylacetamide, 22.1 g of methacrylic acid, and 38 mg of dibutylhydroxytoluene, and the temperature was reduced to -5C. Thionyl chloride in an amount of 30.6 g was dropped thereto at -3.8 to 0.3C over 50 minutes, and the mixture was kept at -4.0 to -0.8C for 30 minutes. A solution obtained by dissolving 36.0 g of 4-cyano-3-trifluoromethylaniline obtained as described above in 79 mL of N,N-dimethylacetamide was dropped into the reaction container at -5.3 to 0C over 65 minutes. The container for dropping was washed with 11 mL of N,N-dimethylacetamide, the washing liquid was added to the reaction solution, and the solution was kept at -5.3 to 0C for 1 hour. After completion of the reaction, the obtained reaction solution was dropped to a mixed solution of 306 mL of ethyl acetate and 252 mL of water at 20C or less. The solution was washed with 18 mL of N,N-dimethylacetamide and the washing solution and the mixed solution were combined, and 378.1 g of an aqueous 16% sodium carbonate solution was added to the solution to adjust the pH to 7.1. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 1.7 m/hr. The organic layer was added with 571.8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 9 m/hr. The organic layer was added with 571.8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 6 m/hr. The organic layer was further added with 571. 8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and then made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 0 m/hr. Then, the organic layer was charged with 180 mL of chlorobenzene, and ethyl acetate and chlorobenzene were distilled out in an amount of 222.3 g by vacuum concentration. Next, 504 mL of chlorobenzene, 1.8 g of activated carbon and 4.9 g of gamma-alumina were charged and the mixture was stirred at 75C for 30 minutes. The alumina and activated carbon were separated by filtration at the same temperature and washed with 36 mL of chlorobenzene. The filtrate and the washing solution were combined, and 545.5 g of chlorobenzene was distilled out by vacuum concentration, and then the mixture was cooled to 20C and stirred at 15 to 20C for 2 hours. Crystal were separated by filtration and washed with 108 mL of a chlorobenzene solution dissolved with 0.45 g of dibutylhydroxytoluene to give 48.94 g of wet crystals. After drying the crystal under reduced pressure, 45.27 g of crystals of N-methacryloyl-4-cyano-3-trifluoromethylaniline was obtained. The LC surface percentage was 99.92%, and the yield was 92.1%.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2204362; (2010); A1;,
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403-54-3, name is 3-Fluorobenzonitrile, belongs to nitriles-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. Safety of 3-Fluorobenzonitrile

REFERENCE EXAMPLE 20 3-(4-Methyl-1-piperazinyl)benzonitrile According to a similar manner to that in Reference Example 17, the title compound was synthesised from 3-fluorobenzonitrile and 1-methylpiperazine. 1 H-NMR (CDCl3) delta (ppm): 2.35(3H, s), 2.55-2.60(4H, m), 3.21-3.25(4H, m), 7.06-7.13(3H, m), 7.28-7.31(1H, m).

The synthetic route of 403-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kogyo Co., Ltd.; US6127541; (2000); A;,
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Adding a certain compound to certain chemical reactions, such as: 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, belongs to nitriles-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 115661-37-5, Recommanded Product: 2-Amino-3-fluorobenzonitrile

2-(1-cyclopropyl-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)-3-fluorobenzonitrile2-Amino-3-fluorobenzonitrile (1.1 g, 8.08 mmol) and 1-cyclopropyl-4-methoxy-1H-pyrrol-2(5H)-one (1.170 g, 7.64 mmol) were combined in acetic acid (10 mL) and heated to 80 C. Methanesulfonic acid (1.311 mL, 20.20 mmol) was dissolved in acetic acid (2 mL) and added dropwise via syringe over 15 minutes. The reaction was stirred for 1 hour at 80 C. and then cooled to RT and placed on a rotoevaporator under high vacuum for 15 minutes at 55 C. to remove the acetic acid. The resulting oil was dissolved in methylene chloride (80 mL) and slowly added dropwise over 20 minutes to a solution of saturated aqueous sodium bicarbonate (70 mL) mixed with 5 N sodium hydroxide (20 mL). This resultant biphasic system was separated. The aqueous was extracted 2 more times with methylene chloride (60 ml) and all organics were combined, dried over magnesium sulfate, and filtered. The filtrate was evacuated to produce 1.5 grams of tan solid. This solid was dissolved in methylene chloride and methanol. Silica gel was added (10 g) and solvent removed. The residue was purified via flash column eluting with ethyl acetate/methylene chloride to afford 2-(1-cyclopropyl-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)-3-fluorobenzonitrile as an off white solid (87%). 1H NMR (500.333 MHz, DMSO) delta 9.18 (s, 1H), 7.70 (m,1H), 7.45 (m, 1H), 4.49 (s, 1H), 3.99 (s, 2H), 2.57 (m, 1H), 0.65 (m, 4H). MS APCI, m/z=258 (M+H). HPLC 1.66 min.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
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Application of 2941-29-9, A common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, molecular formula is C6H7NO, 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 3d: benzyl N-[4-[(2-cyanocyclopenten-1 -yI)-(cyanomethyl)amino]-2- methoxy-phenyl]carbamate[00203] p-Toluenesulfonic acid monohydrate (1 .48g, 7.7gmmol) was added to a stirred solution of 2-oxocyclopentanecarbon itrile (9.35g, 85.71 mmol), benzyl N-[4-(cyanomethylamino)-2-methoxy- phenyl]carbamate (24.26g, 77.g2mmol) and toluene (600mL) at room temperature. The reactionwas then heated at reflux under Dean-Stark conditions for 4 hours. It was then cooled to room temperature and solvent removed until about lOOmL remained. Sat. aq. NaHCO3 (500mL) was then added and the resultant mixture was extracted with EtOAc (2 x 400mL). The combined organic extracts were washed with brine (500mL) and dried over Na2504. Solvent was removed in vacuo to give benzyl N-[4-[(2-cyanocyclopenten-1 -yl)-(cyanomethyl)amino]-2-methoxy-phenyl]carbamate(31 .36g, 77.92mmol, 100percent yield) as a brown solid which was used directly in the next step without further purification.MS Method 2: RT: 2.61, mlz 403.3 [M+H], 401.3 [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; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
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Electric Literature of 115279-57-7, 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. 115279-57-7 name is 2-(4-Aminophenyl)-2-methylpropanenitrile, 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.

Step D Synthesis Route B Amine V (crude product; 695 mg, 3.76 mmol) and nitrile IX (414 mg, 2.58 mmol) is suspended in dichloromethane (16 ml) under an N2 protective-gas atmosphere. 4-Methylmorpholine (0.6 ml, 5.46 mmol) is added. Bis(tri-chloromethyl) carbonate X (460 mg, 1.55 mmol) dissolved in dichloromethane (3 ml) is added dropwise over the course of about 15 min. at room temperature. The reaction solution is stirred at room temperature for a further 1.5 h. Water (30 ml) is added to the reaction mixture, which is then stirred vigorously for 10 min. The organic phase is separated, washed twice with water and dried using Na2SO4. The solvents are removed under reduced pressure in a rotary evaporator, giving 730 mg of crude product. The crude product is purified by means of column chromatography (80 g of Si60, CH2Cl2/5% MeOH), and the suitable fractions are combined. Removal of the solvents gives imidazolone XI (279 mg, 0.79 mmol, 51% yield) as yellow solid (see step E for the further processing of the crude mixture). Analytical data of imidazolone XI: TLC: Rf=0.31 (Si60, CH2Cl2/4% MeOH/1% NH3); m.p.: 167 C.; LC-MS: tR=2.056 min (UV=220 nm), tR=2.063 min. (TIC, with [MH]+=353); 1H NMR (400 MHz, DMSO) delta 8.40 (d, J=5.3, 1H), 7.63-7.55 (m, 2H), 7.51 (s, 1H), 7.39-7.29 (m, 3H), 7.15 (d, J=1.8, 1H), 3.35 (s, 3H), 1.74 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Aminophenyl)-2-methylpropanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2012/220587; (2012); A1;,
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Synthetic Route of 3441-01-8, 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. 3441-01-8, name is 3-Cyanobenzamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 27 A 70 wt. percent aqueous solution (100 ml) of sulfuric acid and m-cyanobenzamide (2.92 g) were placed in a 200-ml three-neck flask, and the resultant mixture was stirred. Subsequently, a 50 wt. percent solution (10 g) of nitrosylsulfuric acid, obtained through dissolution of nitrosylsulfuric acid (5 g) in sulfuric acid (5 g), was added dropwise to the mixture. When the addition was completed, the mixture was allowed to react at room temperature for 30 minutes. The precipitated crystals were collected, washed with water, and dried, to thereby obtain 2.68 g of m-cyanobenzoic acid (yield 92percent). The m-cyanobenzoic acid obtained had a purity of 98percent or more.

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-Cyanobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); 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. 591769-05-0, name is 3-Cyclopentylacrylonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 591769-05-0

To a solution of ethyl 4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d] pyrimidin-4-yl)-1H-pyrazol-3-formate (173 mg, 0.446 mmol, 1.0 eq.) and 3-cyclopentylacrylonitrile (135 mg, 1.11 mmol, 2.5 eq., prepared from the step A of Example 1) in acetonitrile (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (142 mg, 0.94 mmol, 2.1 eq.) at room temperature. The reaction liquid was stirred overnight at room temperature, then heated to 60¡ãC and reacted for 5 hrs. After the mixture was cooled to room temperature, the mixture was diluted with brine and ethyl acetate, and extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was separated by column chromatography on silica gel column to give the titled compound (79 mg, 35percent yield), as a off-white solid. 1H NMR (CDCl3) delta 8.88 (1H, s), 7.98 (1H, s), 7.32 (1H, d, J = 3.6 Hz), 6.46 (1H, d, J = 3.6 Hz), 5.65 (2H, s), 4.27-4.35 (1H, m), 4.23 (2H, q, J = 7.2 Hz), 3.53 (2H, t, J = 8.4 Hz), 3.11 (1H, dd, J = 17.2 Hz, 7.6 Hz), 2.97 (1H, dd, J = 17.2 Hz, 4.0 Hz), 2.58-2.69 (1H, m), 1.88-1.99 (1H, m), 1.51-1.74 (4H, m), 1.22-1.30 (3H, m), 1.08 (3H, t, J = 7.2 Hz), 0.90 (2H, t, J = 8.4 Hz), -0.05 (9H, s). m/z=509[M+1]+.

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; Centaurus BioPharma Co., Ltd.; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Lianyungang Runzhong Pharmaceutical Co., Ltd.; ZHU, Li; XIAO, Dengming; HU, Yuandong; DAI, Liguang; DUAN, Xiaowei; SUN, Yinghui; PENG, Yong; KONG, Fansheng; LUO, Hong; HAN, Yongxin; YANG, Ling; WANG, Shanchun; (94 pag.)EP3235819; (2017); A1;,
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69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, belongs to nitriles-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. HPLC of Formula: C9H9NO

Reference Example 2 2- [4-(4,5-Dihydro-lH-imidazol-2-yl)-phenyn -ethylamine dihvdrochloride a) 4-F2-C1 ,3-Dioxo-l ,3-dihydro-isoindol-2-ylVethyl1-benzonitrileUnder argon, a solution of 4-(2-hydroxy-ethyl)-benzonitrile [HeIv. CMm. Acta 64 (1981) 1688-1703] (4.49 g, 30.5 mmol), phthalimide (4.94 g, 33.55 mmol), triphenylphosphine (8.8 g, 33.55 mmol) and dimethyl formamide (100 mL) was stirred at 0 C for 20 minutes, then diethyl azodicarboxylate (7.59 mL, 48.8 mmol) was added dropwise at 0 0C. The so obtained reaction mixture was stirred at room temperature overnight, then poured into ice-water (740 mL). The precipitated product was filtered off, washed with water and dried. The crude product was recrystallized from 2-propanol to yield 7.83 g (93 %) of the title compound as a yellow solid.

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RICHTER GEDEON VEGYESZETI GYAR RT.; WO2007/72092; (2007); A2;,
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Application of 19924-43-7, 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. 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirring suspension of KOtBu (2.0 mmol) in 1,4-dioxane (5 mL) at 0C, corresponding (het)arylacetonitrile (1a-f, 10a-c) (1.0 mmol) in 1,4-dioxane (2 mL) was added dropwise. After further stirring for 10 minutes, a solution of respective Dithioester (2a-i) (1.0 mmol) in 1,4-dioxane (2 mL) was added to the reaction mixture at 0C, followed by further stirring for 1 h at ambient temperature (monitored by TLC). Iodine (506 mg, 2.0 mmol) was added and the reaction mixture was heated at 90C with continuous stirring (monitored by TLC). It was then diluted with 10% aq. Na2S2O3 solution (50 mL) and extracted with EtOAc (3×25 mL), and the combined organic layer was washed with water (3×25 mL) and brine (1×25 mL), dried (anhyd. Na2SO4), and concentrated under reduced pressure. The crude products were purified by silica gel column chromatography using EtOAc/hexane as eluent.

The synthetic route of 2-(3-Methoxyphenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bonagiri, Saraiah; Acharya, Anand; Pasha, Mohamed A.; Hiriyakkanavar, Ila; Tetrahedron Letters; vol. 58; 49; (2017); p. 4577 – 4582;,
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