Month: May 2021

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. 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 939-80-0

To a solution of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (10.5 g, 48.99 mmol) and 4-chloro-3-nitrobenzonitrile (commercially available from Sigma-Aldrich, Milwaukee, WI)(9.0 g, 49.29 mmol) in DMF (100 mL), was added potassium carbonate (13.6 g, 98.55 mmol) at ambient temperature. The resulting reaction mixture was stirred for 18 hours at 60C. After completion of reaction (monitored by TLC (TLC eluent: 30 % EtOAc in petroleum ether, UV active, Ninhydrin stain active)), the reaction mixture was cooled to ambient temperature and water (300 mL) was added providing a yellow precipitate. The resulting mixture was stirred for 10 minutes, filtered and washed with water (1000 mL). The material thus obtained was dried under vacuum affording tert-butyl ((IRr, 4R)-4-((3-nitropyridin-4- yl)amino)cyclohexyl) carbamate as a yellow solid (16 g, 89.88 %). This solid was directly used in the next step without further purification.

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; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Hongbing; HUANG, Xin; MARTIN, Matthew, W.; PATEL, Vinod; WO2013/134079; (2013); A1;,
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Electric Literature of 19924-43-7, 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. 19924-43-7 name is 2-(3-Methoxyphenyl)acetonitrile, 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.

Exemplary compound 10 was prepared according to a synthetic scheme shown in FIG. 2. The synthetic procedures for preparing compound 10 are described in?Probes for Narcotic Receptor Mediated Phenomena. 34. Synthesis and Structure- Activity Relationships of a Potent mu-Agonist d-Antagonist and an Exceedingly Potent Antinociceptive in the Enantiomeric C9-Substituted 5-(3-Hydroxyphenyl)-N-phenylethylmorphan Series?, J. Med. Chem. 2007, 50, 3765-3776.

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

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; RICE, Kenner Cralle; JACOBSON, Arthur E.; LI, Fuying; GUTMAN Eugene S.; BOW, Eric W.; (99 pag.)WO2019/182950; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1835-49-0, name is Tetrafluoroterephthalonitrile, 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 1835-49-0, SDS of cas: 1835-49-0

[Comparative Example 1]; The same operations as in Example 1 were carried out, except that the amount of the catalyst used was changed from 0.25 g to 0.05 g on a dry weight basis. After a lapse of 7.0 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 83% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1. EPO From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, the tetrafluoroterephthalonitrile as a raw material remained in an amount of 21.0 mol%, and tetrafluoroterephthalaldehyde was obtained in an amount of only 5.0 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.65 mol%, the amount of 2,3,5,6- tetrafluorobenzonitrile was 0.53 mol%, and 1-cyano- 2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 63.1 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 2.88 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.; [Comparative Example 3]; The same operations as in Example 1 were carried out, except that the amount of sulfuric acid used was changed from 20.6 g to 5.15 g (50 mmol). After a lapse of 4.2 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 47% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1.From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, a peak of the tetrafluoroterephthalonitrile as a raw material was below EPO the detection limit, and tetrafluoroterephthalaldehyde was obtained in an amount of only 14.5 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.81 mol%, the amount of 2, 3, 5, 6-tetrafluorobenzonitrile was 0.67 mol%, and 1- cyano-2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 54.0 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 0.04 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.

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

Reference:
Patent; SHOWA DENKO K.K.; WO2006/137347; (2006); A2;,
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Synthetic Route of 630-18-2, 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. 630-18-2, name is Pivalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To an ice cold solution of pivalonitrile (1f, 120 muL, 1.085 mmol) in Et2O (1.0 mL)was added an ethereal solution of 2-naphthylmagnesium bromide (2b, 0.75 M, 1.88mL, 1.410 mmol) and the reaction mixture was stirred at 60 C in a sealed tube for 2 h.After cooling to 0 C, the reaction mixture was treated with anhydrous MeOH (132muL), followed by the addition of CuBr2 (24.3 mg, 0.109 mmol) and anhydrous DMF(10.0 mL). The resulting reaction mixture was stirred at 80 C under an oxygenatmosphere for 6 h. Then the reaction was quenched by the addition of pH 9ammonium buffer solution and the organic materials were extracted with Et2O. Thecombined organic extracts were washed with water, and then with brine and driedover anhydrous MgSO4. The solvents were removed in vacuo and the resulting crudematerial was purified by flash column chromatography using hexane-EtOAc (90:10)to afford 2-naphthonitrile

The chemical industry reduces the impact on the environment during synthesis Pivalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Tnay, Ya Lin; Ang, Gim Yean; Chiba, Shunsuke; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1933 – 1943;,
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Application of 1122-85-6, 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 1122-85-6 as follows.

EXAMPLE 11 Preparation of 4-(p-Chlorophenyl)-4-methyl-2-pentynenitrile A solution of 1,1-dibromo-3-(p-chlorophenyl)-3-methyl-1-butene (38.5 g, 0.113 mol) in tetrahydrofuran is treated with n-butyllithium (0.25 mol, 100 mL of a 2.5 M solution in hexane) under nitrogen over 45 minutes while maintaining the temperature below -65 C, stirred overnight at dry ice/acetone bath temperature, treated dropwise with a solution of phenyl cyanate (14.89 g, 0.125 mol) in tetrahydrofuran over 30 minutes at -65 C to -70 C, allowed to warm to 10 C, and diluted with ethyl acetate and 5% sodium hydroxide solution. The resultant mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with 5% sodium hydroxide solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. The residue is distilled to give the title product as an oil (18.7 g, bp 110-113 C/0.9 mm Hg, 80.7% yield). Using essentially the same procedure, but substituting 1-(2,2-dibromovinyl)-1-(p-chlorophenyl)cyclopropane for 1,1-dibromo-3-(p-chlorophenyl)-3-methyl-1-butene, 3-[1-(p-chlorophenyl)cyclopropyl]-2-propyne-1-carbonitrile is obtained as a yellow solid, mp 62-64 C.

According to the analysis of related databases, 1122-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; EP933027; (1999); 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. 34667-88-4, name is 2-Fluoro-4-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H3FN2O2

Reference Example 114 4-Amino-2-fluorobenzonitrile To a solution of 2-fluoro-4-nitrobenzonitrile (2.51 g) in methanol (125 mL) was added 10percent palladium carbon (50percent containing water, 237 mg), and the mixture was stirred under a hydrogen atmosphere for 3 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) to give the title compound as a pale-yellow solid (yield 1.43 g, 70percent). 1H-NMR (CDCl3)delta: 4.31 (2H, brs), 6.37-6.45 (2H, m), 7.31-7.36 (1H, m).

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; Takeda Pharmaceutical Company Limited; Kajino, Masahiro; Hasuoka, Atsushi; Tarui, Naoki; Takagi, Terufumi; EP2336107; (2015); 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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Cyanobenzyl alcohol

Add p-toluene sulphonic acid (2.11 g, 12.2 mmol) to a solution of 3- hydroxymethyl-benzonitrile( 16.30 g, 122.4 mmol) and 3,4-dihydro-2H-pyran (51.5 g, 612 mmol) in dicliloromethane (500 ml) and stir. After 90 minutes, pour reaction into saturated sodium bicarbonate, remove organics, dry with sodium sulfate, filter and concentrate to give a dark brown oil. Purify the residue by flash chromatography eluting with a gradient of 10-15% ethyl acetate :hexanes to yield the title product as a clear oil (16.20 g, 61%): 1H NMR (CDCl3) delta 1.53-1.91 (m, 6H), 3.56 (m, IH)5 3.88 (m, IH), 4.53 (d, IH), 4.72 (t, IH), 4.81 (d, IH), 7.45 (t, IH), 7.58 (m, 2H), 7.69 (s, IH)

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; ELI LILLY AND COMPANY; WO2006/57860; (2006); A1;,
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134450-56-9, name is 4,5-Difluorophthalonitrile, 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. Recommanded Product: 134450-56-9

1.52 g (9.14 mmol) 9H-carbazole and 1.91 g (13.7 mol)of potassium carbonate were placed in a 50-mE recovery flask, and the interior of the flask was substituted with nitrogen. 15 mE of dimethylsulfoxide was added to themixture, which was stirred under a nitrogen stream at room temperature for 1 hout 0.500 g (3.05 mmol) of 4,5-difluo- rophthalonitrile was added to the mixture. The mixture was stirred under a nitrogen stream at room temperature for 3 hours and then at 500 C. for 20 hours. Thereafier, the mixturewas added to water, followed by stirring. The mixture was extracted with toluene. After the extraction, the extracted solution was rinsed with a saturated sodium chlorine aqueous solution. After rinsing, an organic layer and an aqueous layer were separated, and the organic layer was dried byadding magnesium sulfate thereto. After drying, the mixture was suction-filtered to provide a filtrate. The resulting filtrate was concentrated to provide a solid matter, which was purified by silica gel column chromatography. In the purification, a mixed solvent of toluene and hexane (1/4) was firstly used as a developing solvent, then a mixed solvent of toluene and hexane (7/3) was used, and then toluene was used as a developing solvent (the developing ratio was gradually changed). The resulting fraction was concentratedto provide a solid matter, which was then rinsed by reslurrywith a mixed solvent of acetone and methanol, therebyproviding a pale yellow powdered solid matter in a yieldamount of 1.20 g and a yield of 85.8%.

The synthetic route of 134450-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYULUX, INC.; Adachi, Chihaya; Uoyama, Hiroki; Nomura, Hiroko; Goushi, Kenichi; Yasuda, Takuma; Kondo, Ryosuke; Shizu, Katsuyuki; Nakanotani, Hajime; Nishide, Jyunichi; (83 pag.)US9502668; (2016); 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. 6575-13-9, name is 2,6-Dimethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H9N

General procedure: An oven-dried, three-necked flask was sealed with septa and evacuated/backfilled with N2 three times before starting the reaction. To a mixture of 2.5M n-BuLi in hexane (35 mL, 87.6 mmol) anddry THF (20 mL), maintained at below -70 C, solution of N,N-diethyl-2,4-dimethylbenzamide (10a; 6 g, 29.2 mmol) and 3,4-dimethoxybenzonitrile (11b; 7.15 g, 43.8 mmol) in dry THF (7 mL)were added maintaining the temperature below -60 C. The reaction mixture was stirred at -78 C for 38.5 h. The reaction mixture was then warmed to room temperature and quenched with water. The precipitate was filtered off and washed with water and EtOAc to obtain 9b as an off-white solid. The filtrate was extracted with CH2Cl2, washed with water, and concentrated under reduced pressure. The EtOAc-insoluble fraction was again filtered off and washed with EtOAc to obtain 9b (6.46 g, 74%).

According to the analysis of related databases, 6575-13-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khadka, Daulat Bikram; Woo, Hyunjung; Yang, Su Hui; Zhao, Chao; Jin, Yifeng; Le, Thanh Nguyen; Kwon, Youngjoo; Cho, Won-Jea; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 583 – 607;,
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Related Products of 6393-40-4, These common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, 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.

Reference B; Synthesis of 3,4-diaminobenzamidine monohydrochloride; Step 1; A mixture of 4-amino-3-nitrobenzonitrile (63.3 g, 388 mmol) in 1,4-dioxane (600 mL) and anhydrous ethanol (600 mL) was cooled in an ice water bath to 0-5 C and treated with gaseous HCl for 1.5 h. The reaction mixture was tightly sealed and allowed to warm up to room temperature with stirring for 18 h. The flask was then carefully unsealed and the reaction mixture was diluted with anhydrous diethyl ether (about 2.4 L) until a cloudy solution was obtained. A minimum amount of absolute ethanol required to give a clear solution was then added, and the resulting solution stirred until crystals of 4-amino-3-nitro-benzimidic acid ethyl ester were observed. Ether was then cautiously added to complete the crystallization process and the suspension was allowed to stand for about 30 minutes. The crystals were filtered and washed with dry diethyl ether, then allowed to dry under aspirator vacuum. The crystals were dried in vacuo to give 4-amino-3-nitro-benzimidic acid ethyl ester hydrochloride (84.6 g) as off-white crystals.

The synthetic route of 6393-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2005/118554; (2005); A2;,
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