Month: April 2021

Some common heterocyclic compound, 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, molecular formula is C10H9NO2, 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. Application In Synthesis of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

General procedure: Benzoyl acetonitrile (1, 0.5 mmol), cyclic 2-diazo-1,3-dicarbonyl compound (2, 1.25 mmol), [RhCp*Cl2]2 (0.025 mmol), CsOAc (0.25 mmol), Cu(OAc)2*H2O (1.0 mmol) and DCE (2 mL) were sequentially charged into a reaction tube. The tube was then sealed and the mixture was stirred at 80 C. Upon completion, it was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (10 mL * 3). The combined organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/ethyl acetate (5:1) as eluent to afford 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3672-47-7, its application will become more common.

Reference:
Article; Zhang, Beibei; Li, Bin; Guo, Chenhao; Zhang, Xinying; Fan, Xuesen; Tetrahedron Letters; vol. 59; 32; (2018); p. 3094 – 3099;,
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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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 149793-69-1

A mixture of [3-FLUORO-5- (TRIFLUOROMETHYL)-BENZONITRILE (LANCASTER] Synthesis GmbH; 17 g, 89 [MMOL)] and 2-methylimidazole (Fluka, Buchs, Switzerland ; 22.2 g, 270 [MMOL)] in N, N- dimethylacetamide (80 mL) is stirred at [145C] for 19 h. The solvent is evaporated off under reduced pressure and the residue is dissolved in ethyl acetate (200 mL). The solution is washed with brine (200 mL), dried [(NA2SO4)] and the solvent is evaporated off under reduced pressure to give the crude product which is purified by recrystallisation from ether-hexane to afford the title compound as yellow crystalline solid, m. p. [132-134C.]

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/5281; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 C. The obtained mixture was stirred for 30 min at 50 C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 C and the obtained mixture was stirred for 30 min in the temperature range of 50 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%).

The synthetic route of 630-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
Nitrile – Wikipedia,
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Application of 6621-59-6,Some common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, 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 4Preparation of (R)-4-trimethylammonio-3-[3-[6-(2-phenylethoxy)hex-l- yl]ureido]butyrate Inner SaltPreparation of the intermediate -^-phenylethoxylhexanitrile[0077] Sodium hydride (60% in oil, 1.38 g, 34.38 mmol) was suspended in N,N- dimethylformamide (45 mL) with ice cooling under N2. 2-Phenylethanol (3.43 mL, 28.65 mmol) was added over approx. 5 minutes. After stirring for a further 30 minutes, 6- bromohexanenitrile (4.56 mL, 34.38 mmol) was introduced dropwise. Following complete addition, the mixture was allowed to come to room temperature and was stirred for 19h. Thereafter it was heated to 500C for 3h, then at room temperature for an additional 18h. Water (200 mL) and ethyl acetate (200 mL) were added. The phases were separated and the aqueous phase extracted further with ethyl acetate (2 x 100 mL). The combined organic phases were dried (MgSO4), filtered and evaporated to give a pale, yellow free flowing oil. Chromatography over SiO2 (isohexane-20% ethyl acetate/isohexane gradient) gave the title compound as a colorless oil (1.55 g, 25%). LCMS: Rt = 3.01 min, m/z = 217.92, 154.67, 145.79. 1H NMR (400 MHz, CDCl3): 7.24-7.1 1 (m, 5H), 3.55 (t, J= 7.07 Hz, 2H), 3.37 (t, J = 6.32 Hz, 2H), 3.35 (t, J= 6.57 Hz, 2H), 2.80 (t, J= 7.07 Hz, 2H), 2.23-2.20 (m, 3H), 1.62- 1.40 (m, 10H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromohexanenitrile, its application will become more common.

Reference:
Patent; DARA BIOSCIENCES, INC.; MIDDLEMISS, David; INGOLD, Kenneth, J.; WO2010/8473; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 98730-77-9,Some common heterocyclic compound, 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, molecular formula is C5H7NO, 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.

Thionyl chloride (1.6 mL) was added to a solution of 1-(hydroxymethyl)cyclopropanecarbonitrile (1.42 g) in toluene (20 mL) at room temperature. The reaction mixture was stirred at 80C for 2 hr, and the solvent was evaporated. The resulting residue was dissolved in DMF (20 mL), and 2-bromo-5-(4-hydroxy-3-methoxyphenyl)furo[3,2-c]pyridin-4(5H)-one (2.45 g) and potassium carbonate (4.03 g) were added. The mixture was stirred at 80C overnight. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate three times. The resulting organic layer was dried over magnesium sulfate and concentrated in vacuo, and the resulting residue was filtered through NH silica gel. The filtrate was concentrated in vacuo, and the resulting solid was washed with IPE to give the title compound (2.80 g) as a white solid. MS (ESI+):[M+H]+ 416.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Hydroxymethyl)cyclopropanecarbonitrile, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; KINA, Asato; EP2848622; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 269411-71-4, name is 3-Amino-5-methoxybenzonitrile, 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 269411-71-4, HPLC of Formula: C8H8N2O

Cyclopropylmagnesium bromide (1M in 2-Me THF, 20 mL, 20.00 mmol) was added to a mixture of 3-amino-5-methoxybenzonitrile (1 g, 6.75 mmol) and copper(I) bromide (20 mg, 0.139 mmol) in THF (10 mL) at rt under N2. The mixture was stirred for 1 h at rt then heated under reflux for 2 h. The mixture was cooled and aq. 1M HCl (20 mL) added and stirred for 1 h. The mixture was partitioned between EtOAc (100 mL) and aq NaHCO3 (50 mL), the organic layer separated, dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (40 g column, 0-40% EtOAc/isohexane) to afford the sub-title compound (71 mg) as an orange oil. 1H NMR (CDCl3) 400 MHz, delta: 6.95-6.93 (m, 2H), 6.42 (t, 1H), 3.82 (s, 3H), 3.80 (s, 2H), 2.62-2.56 (m, 1H), 1.23-1.19 (m, 2H), 1.03-0.99 (m, 2H). LCMS m/z 192 (M+H)+ (ES+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Amino-5-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Topivert Pharma Limited; Respivert Limited; BAKER, Thomas Matthew; FYFE, Matthew Colin Thor; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; MEGHANI, Premji; RIGBY, Aaron; SAMBROOK-SMITH, Colin; THOM, Stephen Malcolm; US2014/296208; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H9NO

A mixture of 4-methyl-3-oxopentanenitrile 10i (1.5 eq), benzaldehyde 6a (1.0 eq),CuCl(0.01eq), and MeOH containing concentrated H2SO4 (0.62eq) was stirred at reflux temperature. After stirring at refluxtemperature for 20 h, the precipitated solidwas filtered at 2 Cto yield compound 14.The geometric E isomerwas confirmedby 1H NMRstudies including 1D-NOESY experiments. M.p.53.04 C; IR (KBr) 2206, 1693, 1650, 1587; 1H NMR (400MHz, DMSO-d6) deltaH 1.13 (d, J = 6.8Hz), 3.41-3.59 (m,1H), 7.59-7.70 (m, 3H), 8.08 (d, J = 6.8Hz, 2H), 8.44(s, 1H); 13C NMR (DMSO-d6), deltac 18.4, 35.6, 109.7, 116.7,129.3, 130.8, 131.8, 133.2, 153.4, 198.1; HRMS (ESI) calcdm/z for C13H14NO [M]+ 200.1069, found m/z 200.1075.

According to the analysis of related databases, 29509-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pachore, Sharad S; Ambhaikar, Narendra B; Siddaiah, Vidavalur; Khobare, Sandip R; Kumar, Sarvesh; Dahanukar, Vilas H; Kumar, U K Syam; Journal of Chemical Sciences; vol. 130; 6; (2018);,
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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. 2469-99-0, name is 3-Oxobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Oxobutanenitrile

To a stirred solution of 3oxobutanenitriie (10.00 g, 120.00 mrnol) in DMF (30 mL) was added DMF-DMA (1934 mL, 144.00 rnrnoi) and the reaction mixture was stirred at 80 0Q for 16 h. The reaction mixture was cooled to ambient temperature, concentrated to dryness and diluted with nhexane (200 rnL), The precipitate was collected by suction filtration and dried undervacuum to obtain Intermediate 41A (1300 g, 78.00%). ?H NMR (400 MHz, DMSOd6) pprn2.17 (s, 3 H), 3.25 (s, 3 H), 3.29 (s, 3 H), 7.83 (s, I H). LCMS (Method-L): retention time 054 miii, [M+i-I] 139.2.

According to the analysis of related databases, 2469-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); 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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H6N2O2

A mixture of nitrobenzene acetic acid (1 g, 5.52 mmoles), 1.66 mL OF SOC12, 10 mL dry CHC13 was refluxed for 14 hours. CHC13 and excess thionyl chlorid were removed in vacuo, and the residue was evaporated twice with 25 mL of toluene to remove traces of thionyl chlorid. The residue was taken into 10 mL of toluene and 30 mL of cold concentrated ammonium hydroxyde were added. The white solid formed was collected and dried with etanol in vacuo. Yield: 79 %. ‘H NMR (DMSO-d6, 300MHZ) 8 : 8.14 (M, 2H), 7.71 (M, 2H), 7.06 (brs, 2H), 3.58 (s, 2H). 2- (3-NITROPHENYL) acetamide was added with 10 mL of POC13 and the mixture was heated at reflux for 2 hours. After cooling, the mixture was poured into ice, basified with NA2CO3 and extracted with CH2C12. The organic layer was dried over NA2S04, filtered and evaporated. Purified by flash chromatography on silica gel CH2C12. Yield : 41% H NMR (CDC13,300 MHz) 5 : 8. 14 (M, 2H), 7.69 (d, 1H, J = 8HZ), 7.56 (M, 1H), 3.88 (s, 2H). A solution of 15 mL HBr 48% was cooled to 0C. (430 mg, 2.65 mmoles) OF 3-NITROBENZONITRILE, (574 mg, 4. 85 mmoles) of Sn were added successively. The mixture was stirred at room temperature for 3 hours, then poured into ice. The solution was basified with NA2C03, extracted with CH2C12, dried, filtered and evaporated. Purified by flash chromatography on silica gel ETOH/CH2CL2 (2: 98). Yield: 32% H NMR (DMSO-d6, 300MHZ) 8 : 7.37 (M, 2H), 6.81 (M, 2H), 3.86 (s, 2H). 3-AMINOBENZONITRILE was then reacted with 2-chloroethylisocyanate as described in examples 1- 12 to obtain desired product. Purified by flash CHRMATOGRAPHY on silica gel ETOH/CH2CL2 (5: 95). Yield: 78% H NMR (CDCL3, 300 MHz) 8 : 8.12 (brs, NH, 1H), 7.26 (M, Ar, 4H), 6.97 (brs, NH, 1H), 3.63 (m, CH2,6H).

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; IMOTEP INC.; WO2004/106292; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, A new synthetic method of this compound is introduced below., Computed Properties of C10H9NO2

PREPARATION 13 4-(cyanomethyl)benzoic acid To a stirred solution of methyl 4-(cyanomethyl)benzoate (10 g, 60 mmol) in THF (500 ml) a solution of LiOH (2.90 g, 70 mmol) in water (600 ml) was added. It was stirred at room temperature for 16h. The mixture was concentrated in vacuo and onto the aqueous phase left a solution of HCl 35% (6ml) was added. The solid obtained was filtered, washed with water and hexane and dried in vacuo at 40C for 64h. It was treated with hexane (100 ml) stirring for 1 h. The solid obtained was filtered and dried to yield 7.95 g (86%) of the title compound. LRMS: m/z 260 (M-1)- Retention time: 2.10 min (method A)

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; Almirall, S.A.; EP2343287; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts