Tag: M.W=100-200

Electric Literature of 16588-02-6, A common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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.

4-chloro-3-cyanonitrobenzene (600 mg, 1 eq, 3.29 mmol) and DMF (5 mL) were added sequentially to a 100 mL round bottom flask , the flask was sealed with a rubber stopper and stirred the reaction under ice-water bath. Vacuum pumping then recharging N2 , repeat the cycle for 3 times and after stirring the reaction for 10min, the DMF solution of sodium methoxide was slowly injected into the sealed reaction flask through the syringe. After 1h of reaction, the reaction was completed and was stopped. After adding 100 mL of ethyl acetate for dilution, it was washed oncewith the saturated ammonium chloride aqueous solution and saturated aqueous sodium chloride solution. The aqueous phase was again washed with ethyl acetate and the combined organic phase was dried over anhydrous sodium sulfate for 30 min. The mixture was filtered , concentrated then separated by Silica gel column chromatography (PE : EA =5:1) to give a product of 440 mg of product as a White crystalline solid (compound 6) in 75% yield .

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Xu Zhongliang; Wang Heyao; Cai Mengxin; (31 pag.)CN106892871; (2017); A;,
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Reference of 5414-21-1, 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. 5414-21-1, name is 5-Bromovaleronitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield). Rf = 0.40 (dichloromethane/methanol 95:5). 1H NMR: delta 1.63-1.71 (m, 2H), 1.79-1.87 (m, 2H), 2.37 (s, 3H), 2.60-2.66 (m, 2H), 3.80-3.86 (m, 2H), 7.18-7.29 (m, 2H), 7.51-7.54 (m, 1H), 7.61-7.62 (m, 1H). 13C NMR: delta 20.0, 21.7, 22.1, 27.4, 50.1, 123.3, 126.8, 128.3, 130.5, 138.1, 140.4, 166.2. MS (ESI) m/z [M+H]+ Calcd for C12H16N+: 174.13. Found: 174.2.

The chemical industry reduces the impact on the environment during synthesis 5-Bromovaleronitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Matera, Carlo; Quadri, Marta; Sciaccaluga, Miriam; Pome, Diego Yuri; Fasoli, Francesca; De Amici, Marco; Fucile, Sergio; Gotti, Cecilia; Dallanoce, Clelia; Grazioso, Giovanni; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 392 – 405;,
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Adding a certain compound to certain chemical reactions, such as: 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, 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 455-18-5, Product Details of 455-18-5

General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4.

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

Reference:
Article; Wan, Xiao-Min; Liu, Zi-Lin; Liu, Wan-Qing; Cao, Xiao-Niu; Zhu, Xinju; Zhao, Xue-Mei; Song, Bing; Hao, Xin-Qi; Liu, Guoji; Tetrahedron; vol. 75; 18; (2019); p. 2697 – 2705;,
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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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-Bromo-3-methylbenzonitrile

Preparations 27-31 are prepared essentially as described for Preparation 26 using the appropriate boronic acid and l-(3-bromo-pyridin-2-yl)-piperazine.Preparation 32: 3-Methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzonitrile Stir together 4-bromo-3-methylbenzonitrile (5.20 mmol, 1.02 g), bis(pinacolato) diboron (5.62 mmol, 1.43 g), potassium acetate (15.6 mmol, 1.53 g), and palladium acetate (0.16 mmol, 40 mg) in dry N,N-dimethylformamide (20 mL). Purge the reaction for 30 min. then heat to 85 0C overnight. Partition between water (100 mL) and ethyl acetate (100 mL), wash aqueous layer with ethyl acetate (100 mL). Combine ethyl –50-acetate washings and dry over magnesium sulfate, filter and concentrate in vacuo. Purify (silica gel chromatography, eluting with 0: 100 to 20:80 ethyl acetate:isohexane) to give the title preparation as a white powder (560 mg, 44% yield). MS (ES): m/z = 244 [M+H]+.

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); A1;,
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Reference of 19924-43-7,Some common heterocyclic compound, 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, molecular formula is C9H9NO, 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.

General procedure: Amidoxime Formation To a solution of nitrile (1 eq.) in EtOH (12 mL mmol-1) was added hydroxylamine (50% v/v in H20, 4 mL mmol-1) and the reaction mixture heated under reflux for 5 hours. After removal of all volatiles under reduced pressure the crude produce was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Methoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; IMPERIAL INNOVATIONS LIMITED; LEATHERBARROW, Robin; TATE, Edward; YU, Zhiyong; RACKHAM, Mark; WO2013/83991; (2013); 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. 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H4Cl2N2

3,5-Dichloro-4-aminobenzylamine To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise 3,5-dichloro-4-aminobenzonitrile (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at rt for 2 h. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with THF three times. The solvent was removed under vacuum and the residue was purified by chromatography with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): delta3.65 (s, 2H), 7.2 (s, 2H).

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 78473-00-4.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/232581; (2007); A1;,
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These common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, 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. Recommanded Product: 3-Cyanobenzyl alcohol

After 3-(hydroxymethyl)benzonitrile (1.33 g, 10 mmol) was dissolved in dimethylformamide (18 mL), triphenylphosphine (3.14 g, 12 mmol) and imidazole (0.82 g, 12 mmol) were added thereto, and the mixture was cooled to -20C. Iodine (2.79 g, 11 mmol) was added dividing in 5 portions thereto, and the result was stirred for 2 hours at -10C. A 5% aqueous ammonium chloride solution (60 mL) was added to the reaction solution, and the result was extracted with a diethyl ether/ethyl acetate=1/1 solution (60 mLx2). The organic layers were combined, washed with a 1% aqueous sodium thiosulfate solution to remove excess iodine, washed with salted water, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was separated and purified using silica gel column chromatography (ethyl acetate/normal-hexane=1/9) to give a target compound (1.9 g, 78%) in a white powder state. 1H-NMR (300 MHz, CDCl3) delta 4.41 (s, 2H), 7.2-7.66 (m, 4H); MS (EI, m/e)=243 (M+).

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

Reference:
Patent; Korea Research Institute of Chemical Technology; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; (98 pag.)EP2781519; (2014); A1;,
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Electric Literature of 145689-34-5, 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. 145689-34-5 name is 2-(2,3-Difluorophenyl)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.

EXAMPLE 65; 2-[1-(2,3-Difluoro-phenyl)-ethyl]-4,5-dihydro-1H-imidazole; a) rac-2-(2,3-Difluoro-phenyl)-propionitrile; A solution of 1.586 g (16 mmol) diisopropylamine in 25 ml tetrahydrofuran was cooled with sodium chloride/ice to -10 C. A solution of 9 ml (14 mmol) 1.6 M butyl lithium in hexanes was added drop-wise. After stirring for 10 min the resulting LDA solution was cooled to -78 C. and a solution of 2.00 g (13 mmol) 2,3-difluorophenyl-acetonitrile in 5 ml tetrahydrofuran slowly added. The reaction mixture was stirred at -78 C. for 40 min, then 2.22 g (16 mmol) methyl iodide were added and the cooling bath was removed after 5 min. The mixture was stirred for 2.5 h at room temperature, and then aqueous ammonium chloride solution was added. The mixture was extracted twice with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and evaporated. The residue was purified using column chromatography (SiO2, heptanes/ethyl acetate 9:1) to yield 1.12 g of rac-2-(2,3-difluoro-phenyl)-propionitrile as a light yellow liquid; MS (EI): 167.1 (M+·), 152.1 (((M-CH3)+·), 100%).

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

Reference:
Patent; Galley, Guido; Zbinden, Katrin Groebke; Hoener, Marius; Kolczewski, Sabine; Norcross, Roger; Stalder, Henri; US2007/197621; (2007); A1;,
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Application of 77326-36-4, 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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2: Methyl- (2-cyano-3-methoxy-phenyl) sulfonamide; 2.1 : 2-Amino-6-methoxy-benzonitrile A solution of 70 g (0.5 mol) of 2-amino-6-fluoro-benzonitrile (prepared, e. g. according to US 4,504, 660) in 250 ml of N, N-dimethylformamide was initially charged and a solu- tion of 30.6 g (0.55 mol) sodium methoxide in 70 ml of methanol was added dropwise at room temperature while stirring. The mixture was then refluxed for 5 hours under stirring. The completion of the reaction was monitored by TLC. Additional 25 g of so- dium methoxide in 35 ml methanol were added and the reaction mixture was refluxed for additional 4 hours while stirring. The reaction mixture was concentrated under re- duced pressure, the resulting residue was triturated with water, sucked off and the ob- tained solids were dissolved in ethyl acetate. The resulting solution was concentrated in vacuo. The obtained residue was triturated with petroleum ether and sucked off to afford 48 g (63% of theory) of a brownish solid having a melting point of 143-146C.

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2005/35486; (2005); A1;,
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Application of 16532-79-9,Some common heterocyclic compound, 16532-79-9, name is 4-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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.

Step a) intermediate 20 Synthesis of 2-(4-bromophenyl)-2-methylpropanenitrile.The preparation of 2-(4-bromophenyl)-2-methylpropanenitrile is carried out as described in J. Med. Chem. (1995), no 38, page 1608-1628. Sodium Hydride (60% susp. in oil, 6.66 g, 166.3 mmol) is added in many portions over 1 hour to 2-(4-bromophenyl)-acetonitrile (1Og, 51.0 mmol), dissolved in anhydrous DMF and methyl iodide (14.838g, 102.0 mmol) at 0 0C. This solution turns to a thick and brown orange paste. It is left stirring to slowly warm up to room temperature (18h). The organic solution is partitioned between water and ethyl acetate, separated, dried over anhydrous sodium sulfate and filtered. The solution is concentrated under reduced pressure and the resulting crude is purified on silicagel using a 0 to 20 % ethyl acetate in hexane gradient to yield the desired compound (4.9 g, 42%) as a clear oil. IH NMR (400 MHz, CHLOROFORM-D) delta ppm 1.71 (s, 6 H) 7.35 (d, /=8.79 Hz, 2 H) 7.52 (d, /=8.79 Hz, 2 H)

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

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
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