Tag: M.W=100-200

Application of 873697-68-8, 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. 873697-68-8, name is 3-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 3 Step 2. A solution of 3B in dichloromethane (about 1.5 M 3B in DCM) at RT under nitrogen mixture was cooled to ~0C, and 2.0 eq of IM diisobutyllithiumaluminum hydride (DIBAlH) in DCM was added drop wise over -3.5 hours, maintaining an internal reaction temperature < 00C. Upon completion of the DiBAlH addition, the reaction mixture was added dropwise with vigorous stirring to a cooled solution (-00C) of 40 volumes of 15% Rochelle salt and 10 volumes of DCM, maintaining an internal reaction temperature below 100C. The flask was rinsed with 10 volumes of DCM and the mixture was allowed to warm to room temperature and stirred for 4 hours. The layers were separated, and the aqueous layers were back extracted with 20 volumes of DCM. The combined organic layers were washed with 20 volumes of water. The organic layer was dried over sodium sulfate and concentrated to afford a brown foam, which was dried under vacuum (-30 in Hg) at RT to afford 3C (92% yield). Example 3 Step 3A/B. A solution 1 eq of 3C, tetrahydrofuran (about 1.4 M 3C in THF) and 1.05 eq of methyl piperazine-1-carboxylate and was allowed to stir at ambient temperature for 3 hours. To the reaction mixture was added 1.5 eq of sodium triacetoxyborohydride portionwise over -40 min, maintaining an internal reaction temperature below 45C. The reaction mixture was stirred overnight at room temperature. To the reaction mixture was added 5 volumes of water dropwise, over 1 hour, maintaining an internal reaction temperature below 300C. Ethyl acetate (EtOAc, 5 volumes) was then added, and the layers were separated. The aqueous layers were back extracted with 5 volumes of EtOAc. The combined organic layers were washed with saturated sodium bicarbonate and solid sodium bicarbonate was added as needed to bring the pH to 8 (pHydrion papers). The layers were separated, and the organic layer was washed with 5 volumes of brine. The organic layer was dried over sodium sulfate and activated carbon was added in the drying step. The organics were filtered through celite and the celite pad was rinsed 4 times with EtOAc. The organics were concentrated and dried overnight on the rotavap (~30 in Hg at RT) to afford an amber-brown oil. Step 3C. All calculations are based on the amount of 3C (R= O).[0146] To 3 volumes of methanol (based on 3C, R=O)under N2 over an an ice/brine/acetone bathwas added3 eq of acetyl chloride dropwise over 3 hours, maintaining an internal reaction temperature below 00C. The solution was then stirred for an additional 1 hour below 00C. A solution of 1.0 eq of unpurified 3D (from Steps 3 A/3B above) in MeOH (about 3.6 M based on 3C, R=O) was added dropwise over 30 min, maintaining an internal reaction temperature below 15C..The reaction was allowed to warm to room temperature overnight. The solids were filtered the next day and rinsed with 2x 0.5 volumes of MeOH, 5 volumes of 1:1 rerf-butyl methyl ether (MTBE):MeOH, and 5 volumes of MTBE.[0147] The solids were then taken up in 5 volumes of EtOAc and saturated sodium bicarbonate and solid sodium bicarbonate were added as needed to bring the pH of the aqueous layer to 8 (pHydrion papers). The layers were separated, and the aqueous layer was extracted with 5 volumes of EtOAc. The combined organic layers were washed with 5 volumes of brine, dried over sodium sulfate, and concentrated to afford a pale orange solid which was dried under vacuum (-30 in Hg) at ~40C to afford 3D (50% yield). 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-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CYTOKINETICS, INC.; WO2007/78839; (2007); A2;,
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Some common heterocyclic compound, 143879-80-5, name is 2,3,4-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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. name: 2,3,4-Trifluorobenzonitrile

Scheme 21[0368] To 2,3,4-trifluorobenzonitrile (265 mg, 1.68 mmol) in a flask, a solution of D- leucine amide hydrochloride (282 mg, 1.68 mmol) and DIEA (0.880 mL, 5.06 mmol) in DMSO (5 mL) was added. After being stirred at room temperature for 68 h, water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2S04, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-70% EtOAc in hexane to give (R)-2-(4-cyano-2,3-difluorophenylamino)-4-methylpentanamide (113 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 143879-80-5, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
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Reference of 10406-25-4, The chemical industry reduces the impact on the environment during synthesis 10406-25-4, name is 4-(Aminomethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

Precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 11.9 g of p-cyanobenzoic acid (yield 90%, based on p-cyanobenzylamine). The p-cyanobenzoic acid obtained had a purity of 96%.

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, 4-(Aminomethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); B1;,
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Electric Literature of 19472-74-3, 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. 19472-74-3, name is 2-Bromophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3aa; yield: 32.9 mg (86%); tan yellowsolid; mp 155.6-156.3 C.

The chemical industry reduces the impact on the environment during synthesis 2-Bromophenylacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
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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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1009-35-4

Step A3-amino-4-fluorobenzonitrileUsing 4-fluoro-3-nitrobenzonitrile (13.64 g, 82.11 mmol) and according to the method of Reference Example 68, step A, the title compound (10.16 g, yield 91percent) was obtained as a pale-yellow solid.1H-NMR (300 MHz, CDCl3); delta(ppm) 3.94 (brs, 2H), 7.00-7.09 (m, 3H).

According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; US2012/196824; (2012); A1;,
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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. 6629-04-5, name is N-Cyanoacetylurethane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: N-Cyanoacetylurethane

A suspension of 5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenylamine (24) (134 mg, 0.42 mmol) in water (5.6 mL) was treated with concentrated hydrochloric acid (2.8 mL). The reaction mixture was cooled to 00C and then was treated with a solution of sodium nitrate (36.5 mg, 0.529 mmol) in water (0.2 mL) under the surface of the reaction mixture followed by a water (0.2 mL) rinse. The reaction mixture was stirred at 00C for 30 min, and a solution formed. In a separate flask, equipped with a magnetic stirrer, was added N-cyanoacetylurethane (73 mg, 0.46 mol), water (9.4 mL) and pyridine (2.8 mL). This reaction mixture was cooled to 00C and the solution from the first reaction was quickly filtered and poured into the second reaction mixture. An orange precipitate formed and the suspension was stirred at 00C for 30 min. The solid was filtered and rinsed with water followed by petroleum ether. The solid was dried in a vacuum oven overnight at 800C to afford 2-cyano-2-{ [3,5-dichloro-4-(5-isopropyl-6-oxo-l,6-dihydro-pyridazin-3-yloxy)- phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (30) (156 mg, 76%) as an orange solid; EI(+)-HRMS m/z calcd for Ci9Hi8Cl2N6O5 (M+H) 481.0789, found 481.0790. Molecular Weight =481.2985; Exact Mass =480.0716

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 6629-04-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/9913; (2007); A1;,
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Synthetic Route of 14447-18-8, A common heterocyclic compound, 14447-18-8, name is Benzyl cyanoacetate, molecular formula is C10H9NO2, 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.

2-Cyano-4,4, 8-trimethyl-non-2-enoic acid benzyl ester. To a mixture of 2,2, 6-Trimethyl-heptanal (1.05 g, 6.73 mmol), piperidine (0.19 mL, 2.01 mmol) and benzyl cyanoacetate (1.29 g, 7.4 MMOL) in toluene (50 mL) was added glacial acetic acid (0.72 g, 12.1 mmol). The flask was fitted with a Dean-Stark trap, and the mixture was heated at reflux for 18. The mixture was cooled, treated with dilute HCI, and the layers were separated. The organics were washed with a saturated sodium bicarbonate solution followed by brine, and dried (MGS04), filtered and concentrated. The residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc) to give 1.3 g of 2-Cyano-4, 4, 8-TRIMETHYL-NON-2-ENOIC acid benzyl ester M/Z 314 (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; WARNER-LAMBERT COMPANY LLC; WO2005/30184; (2005); A2;,
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Electric Literature of 55984-93-5, A common heterocyclic compound, 55984-93-5, name is 2-Methylterephthalonitrile, molecular formula is C9H6N2, 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.

Into a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-methylbenzene-l,4-dicarbonitrile (4 g, 28.14 mmol, 1.00 equiv), [(tert-butoxy)(dimethylamino)methyl]dimethylamine (9.8 g, 56.23 mmol, 2.00 equiv) in N,N-dimethylformamide (50 mL). The resulting solution was stirred overnight at 75 °C, and then concentrated under vacuum. The resulting mixture was washed with 50 mL of hexane. The solids were collected by filtration. This provided 5.3 g (95percent) of 2-[(E)-2- (dimethylamino)ethenyl]benzene-l,4-dicarbonitrile as a yellow solid.

The synthetic route of 55984-93-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; YU, Chul; YEE, Calvin W.; XU, Qing; GWALTNEY, II, Stephen L.; METCALF, Brian W.; LARDY, Matthew A.; RICHARDS, Steven; WO2015/171526; (2015); A2;,
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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. 20925-27-3, name is 4-Amino-2-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H5ClN2

EXAMPLE 54A 2-chloro-4-iodobenzonitrile A solution of 4-amino-2-chlorobenzonitrile (30.5 g, 0.2 mol) in 1:1 diethyl ether/3M HCl (600 mL) at 0 C. was treated dropwise over 15 minutes with a solution of sodium nitrite (18 g, 0.26 mol) in water (100 mL), stirred 15 minutes, then treated with a solution of potassium iodide (50 g, 0.3 mol) in water (50 mL) dropwise over 45 minutes, warmed to room temperature, and stirred for 1.5 hours. The organic phase was washed with water (3*100 mL) and the combined aqueous layers were extracted with diethyl ether. The combined organic layers were combined, washed sequentially with saturated NaHCO3, 25% Na2S2O3, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 19:1/hexanes:ethyl acetate, triturated in hexanes, filtered, and dried to provide the desired product.

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; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;; ; Patent; Claiborne, Akiyo K.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2003/87940; (2003); 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 134450-56-9 as follows. category: nitriles-buliding-blocks

1 mmol of the starting material CN-1-1, 3.0 mmol of potassium carbonate and 2.5 mmol of the starting material F-8-2, Was added to 10 mL of dimethylsulfoxide and heated at 150 C for 8 hours. After cooling to room temperature, 200 mL of water was added to the system to precipitate a solid which was purged and purified by column chromatography to give a solid.

According to the analysis of related databases, 134450-56-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Huang Da; Cao Chenhui; Xie Zaifeng; Ma Tengda; (39 pag.)CN107011243; (2017); A;,
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