Category: nitriles-buliding-blocks

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. 6136-93-2, name is 2,2-Diethoxyacetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,2-Diethoxyacetonitrile

EXAMPLE II Preparation of 2-Ethylidene-6-methyl-cis-3-heptenal A solution of 5.40 g of isobutylacetylene in 50 ml of diethyl ether is treated with 30 ml of 2.2 N n-butyl-lithium in hexane at -20 C., and after several minutes the resulting solution is treated with 8.50 g of diethoxyacetonitrile and then warmed slowly to room temperature. After about 1.5 hours the dark mixture is cooled and brought to a pH of about 2 with ten percent sulfuric acid. The layers are then separated and the organic layer is washed successively with water and saturated aqueous sodium bicarbonate solution and then dried over sodium sulfate. Evaporation of the solvent provides 4.6 g of a dark oil, shown by IR and NMR to contain 1,1-diethoxy-6-methyl-3-heptyn-2-one.

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; International Flavors & Fragrances Inc.; US4045497; (1977); A;,
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Synthetic Route of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Pyrrole (2, 6, 6-trimethyltetrahydroindol-4-one) (1.5 g, 8.5 mmol) and 2-bromo-4-fluorobenzonitrile (1.69 g, 8.5 mmol) were dissolved in anhydrous DMF (50 mL) . To this NaH (95%, 408 mg, 17.0 mmol) was added and stirred at 50 0C for 1 h. The reaction mixture was cooled to RT and H2O was added. Product crashed out of solution and was filtered and dried under vacuo (2.4 g, 79%). (100% clean by LCMS, product M+H = 357).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-fluorobenzonitrile, its application will become more common.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (2006); A1;,
Nitrile – Wikipedia,
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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., SDS of cas: 874-97-5

1-methyl-3-[(3-cyanophenylmethoxy)methyl]-2(1H)-pyridinone, 12a. To a 0 C suspension of sodium hydride (41 mg, 60% suspension in mineral oil, 1.01 mmol), in THF (3 mL) was added 3-cyanobenzyl alcohol (100 mg, 0.75 mmol). After the mixture was stirred for 1 h at 0 C, 3-(bromomethyl)-1-methylpyridin-2(1H)-one3 (152 mg, 0.75 mmol) in THF (3mL) was added dropwise. The reaction mixture was slowly allowed to warm to room temperature and stirred for additional 3 h before diluting with saturated aqueous ammonium chloride. After extraction with ethyl acetate, the combined organics were washed with brine, concentrated invacuo and purified by column chromatography using 5:95 MeOH/DCM to get title compound as a colorless soild (136 mg, 71 %).

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:
Article; Khatri, Buddha B.; Vrubliauskas, Darius; Sieburth, Scott McN.; Tetrahedron Letters; vol. 56; 30; (2015); p. 4520 – 4522;,
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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. 935-02-4, name is 3-Phenylpropiolonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Phenylpropiolonitrile

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation 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:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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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. 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;,
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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

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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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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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;,
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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