Category: nitriles-buliding-blocks

Synthetic Route of 51632-29-2, 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 51632-29-2 as follows.

3-phenoxyphenylacetonitrile was added to a 25 ml Schlenk reaction tube under a nitrogen atmosphere.(0.4 mmol), dimethylamine borane complex (1 equivalent), potassium t-butoxide (1.5 eq.), deuterated N,N-dimethylformamide (2 ml), rubber stopper on the reaction tube After being placed in an oil bath, the reaction was carried out at 80 C for 7 h, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography, and the eluent was petroleum ether / ethyl acetate ( v: v = 10: 1), obtaining alpha-monodecylmethyl-3-phenoxybenzenepropionitrile;Then, under a nitrogen atmosphere, a 25 ml two-neck round bottom flask was charged with alpha-monodeuteromethyl-3-phenoxyphenylpropanenitrile (0.2 mmol), sodium hydroxide (1.5 mmol/ml), water (8 ml). Ethanol (2ml), burned in a round bottomThe bottle was placed in a rubber bath and placed in an oil bath. The reaction was refluxed at 110 C for 5 h. The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was extracted and separated by column chromatography. Petroleum ether / ethyl acetate (v: v = 5: 1) gave alpha-monodecylmethyl-3-phenoxyphenylpropionic acid, i.e., alpha-monodecylmethyl-fenofol.Product yield 80%, light yellow solid

According to the analysis of related databases, 51632-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Science and Technology of China; Wang Yifeng; Xia Huimin; Zhang Fenglian; (10 pag.)CN108003004; (2018); A;,
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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 939-79-7 as follows. HPLC of Formula: C8H6N2O2

(2) 4-Bromomethyl-3-nitrobenzonitrile A solution of 4-methyl-3-nitrobenzonitrile (30 g), N-bromosuccinimide (37 g) and azobisisobutyronitrile (3.1 g) in carbon tetrachloride (300 ml) was refluxed under heating for 8 hr. To the reaction mixture was added water (100 ml) and the mixture was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate_hexane=1:4) and recrystallized from ethyl acetate-hexane to give the title compound (23.7 g) as pale-yellow crystals, m.p.=85-89 C. 1H-NMR(DMSO-d6)delta: 4.96(2H, s), 7.97(1H, d, J=7.9 Hz), 8.22(1H, dd, J=1.3, 7.9 Hz), 8.61(1H, d, J=1.3 Hz); IR(KBr): 3082, 2235, 1614, 1530 cm-1; MS(EI): 241(M+); Elemental analysis: Calculated: C; 39.86, H; 2.09, N; 11.62; Found: C; 40.64, H; 2.15, N; 11.85.

According to the analysis of related databases, 939-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Pharma Corporation; US6455528; (2002); B1;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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: 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Experiment 7: The general procedure of Experiment 2 was applied. No acetic acid was present in the system. The experiment was carried out with a small amount of water (0.0 IV) An exemplary batch gave molar yield: 32.5%; enantiomeric purity: 98.7% S. Experiment 8: The general procedure of Experiment 2 was applied. No acetic acid was present in the system. The experiment was carried out with a higher amount of water (0.05V) Exemplary batches gave: Molar yield: 34.7%; enantiomeric purity: 99.0% S.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103146-25-4, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
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Related Products of 38487-86-4, 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. 38487-86-4 name is 2-Amino-4-chlorobenzonitrile, 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.

To a suspension of anhydrous AlCl3 (570 mg, 4.27 mmol) and freshly sublimed 2-amino-4-chlorobenzonitrile (618 mg, 4.05 mmol) in 1,2-dichloroethane (6 mL) was added dropwise a solution of enone 7 (R9 = i-Pr) (440 mg, 2.50 mmol) in 1,2-dichloroethane (27 mL). The reaction mixture was stirred under reflux for 14 h, allowed to cool to room temperature, diluted with water (35 mL) and THF (35 mL), made basic by addition of 5 N NaOH (20 mL), and stirred at room temperature for 30 min. The organic solvents were removed under reduced pressure, and the residue was filtered. The brown solid residue (698 mg) was subjected to column chromatography [silica gel (50 g), CH2Cl2/MeOH/25% aqueous NH4OH mixtures as eluent]. On elution with CH2Cl2/MeOH/25% aqueous NH4OH 98:2:0.5, huprine 8 (335 mg, 48% yield) was obtained as a beige solid.A solution of huprine 8 (335 mg, 1.07 mmol) in CH2Cl2 (15 mL) was filtered through a polytetrafluoroethylene (PTFE) 0.45 mum filter, treated with 1.81 N methanolic solution of HCl (1.24 mL, 2.24 mmol), and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 8:1 (9 mL), 8¡¤HCl (274 mg) was obtained as a beige solid, mp 218-219 C (AcOEt/MeOH 8:1). IR (KBr) nu 3500-2500 (max at 3476, 3322, 3172, 2956, 2926, 2892, 2821, C-H, N-H, and N+-H st), 1644, 1609, 1576, and 1557 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 0.80 (d, J = 7.0 Hz, 3H) and 0.84 (d, J = 7.0 Hz, 3H) [9-CH(CH3)2], 1.92 (dm, J = 12.0 Hz, 1H, 13-Hsyn), 1.97-2.06 [complex signal, 2H, 13-Hanti and 9-CH(CH3)2], 2.09 (d, J = 17.0 Hz, 1H, 10-Hendo), 2.45 (dd, J = 17.0 Hz, J’ = 5.0 Hz, 1H, 10-Hexo), 2.70 (m, 1H, 7-H), 2.82 (ddd, J = 17.5 Hz, J’ = J = 2.0 Hz, 1H, 6-Hendo), 3.05 (dd, J = 17.5 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.34 (m, 1H, 11-H), 4.86 (s, NH2 and NH+), 5.52 (dm, J = 5.0 Hz, 1H, 8-H), 7.30 (dd, J = 8.5 Hz, J’ = 2.0 Hz, 1H, 2-H), 7.66 (d, J = 2.0 Hz, 1H, 4-H), 8.06 (d, J = 8.5 Hz, 1H, 1-H); 13C NMR (75.4 MHz, CD3OD) delta 21.4 (CH3) and 21.9 (CH3) [9-CH(CH3)2], 28.2 (CH, C11), 29.2 (CH, C7), 30.4 (CH2, C13), 32.3 (CH2, C10), 35.9 [CH, 9-CH(CH3)2], 39.5 (CH2, C6), 115.5 (C) and 116.6 (C) (C11a and C12a), 122.9 (CH, C4), 124.6 (CH), 124.9 (CH), and 125.4 (CH) (C1, C2, and C8), 136.6 (C, C4a), 143.9 (C) and 145.9 (C) (C3 and C9), 151.4 (C) and 157.8 (C) (C5a and C12). Anal. Calcd for C19H21ClN2¡¤HCl¡¤1/3H2O (355.25): C, 64.24; H, 6.43; N, 7.89; Cl, 19.96. Found: C, 64.09; H, 6.45; N, 7.64; Cl, 19.70.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
Nitrile – Wikipedia,
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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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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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. 97165-77-0, name is 3,5-Dibromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dibromobenzonitrile

To a round bottom flask was added 20.0 g (77 mmol) of 3,5-dibromobenzonitrile and 13.2 g (77 mmol) of 1-naphthaleneboronic acid,1.8 g (2 mmol) of tetrakistriphenylphosphine palladium {Pd (PPh3) 4}21.2 g (153 mmol) of potassium carbonate,30 mL of water,100 ml of toluene and 100 ml of tetrahydrofuran were added and the mixture was refluxed for 12 hours.After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure.Hexane, and dried to obtain 13.1 g of a white solid having a yield of 55.5%.

The synthetic route of 97165-77-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Ltd.; Ryu Se-jin; Sim So-yeong; Lee Sang-hae; (39 pag.)KR101964677; (2019); 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. 21423-81-4, name is 3-Chloro-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Chloro-4-methylbenzonitrile

A mixture of 3-chloro-4-methylbenzonitrile (4.8 g), Lambda/-bromosuccinimide (5.5 g), dibenzoyl peroxide (0.43 g) and carbon tetrachloride (30 mL) was heated a reflux for 2 hours. The mixture was cooled to room temperature, filtered and washed with dichloromethane. The filtrated was washed with water, dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 19:1 by volume) gave title compound, 4.1 g.1H NMR (CDCI3): delta 4.55 (s, 2H), 7.55 (m, 2H), 7.70 (m, 1H).

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; ARGENTA DISCOVERY LTD.; WO2007/36743; (2007); A2;,
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Application of 6011-14-9,Some common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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.

A mixture of 2-aminoacetonitrile hydrochloride (5 g, 54.0 mmol), NaHC03(18.16 g, 216 mmol) and dioxane (50 mL) in H20 (100 mL) was stirred at 0C. Then a solution of benzyl carbonochloridate (1 1.06 g, 64.8 mmol, 9.22 mL) in toluene (10 mL) was added at 0C and stirred at 20C for 12 hours. The mixture was poured into water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mLchi3).The combined organic phases were washed with brine (100 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give benzyl(cyanomethyl)carbamate (1 .70 g).1H NMR (chloroform-c/400 MHz): 7.40-7.31 (m, 5H), 5.35- 5.13 (m, 3H), 4.16-4.12 (m, 2H).

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

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (270 pag.)WO2018/7249; (2018); A1;,
Nitrile – Wikipedia,
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Related Products of 950596-58-4, 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. 950596-58-4 name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, 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.

In the reaction flask was charged with 2-amino-4,5-bis (2-methoxyethoxy) – benzonitrile (37.01g, 0.139mol) and acetonitrile (185ml); added 3-ethynyl aniline salt acid (30.00g, 0.195mol), trifluoroacetic acid (17.43g, 0.152mol) and formamidine acetate (15.19g, 0.145mol) in the resultant mixture.The reaction mixture temperature was adjusted to reflux temperature of the solvent, and maintained in this condition for about 15 hours.At the end of the reaction, the temperature was adjusted to about 25 , the solvent was removed by vacuum distillation, and methyl ethyl ketone (430ml).(2 ¡Á 100ml) and water (2 ¡Á 100ml) the organic phase was washed with saturated sodium bicarbonate solution.The organic phase was collected and concentrated by vacuum distillation to a residue.The resulting crude product was suspended in ethyl acetate (450ml), and adding 37% hydrochloric acid solution (14.38g, 0.145mol), maintained at a temperature of 15 for about 30 minutes.The resulting solid was filtered, washed under vacuum at 45 C oven dried to obtain 36.02g erlotinib hydrochloride.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Guilin Hui Pak Biotechnology Co., Ltd.; M, Balatella; P, Palanza; M, Garbodi; G, Castaldi; (7 pag.)CN105541735; (2016); A;,
Nitrile – Wikipedia,
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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 75279-53-7 as follows. COA of Formula: C8H5ClFN

A solution of 4-chloro-2-fluorobenzeneacetonitrile (0.059 mol) in anhydrous DMF (150 ml) was chilled on an ice-bath. t-BuOK (0.118 mol) was added under nitrogen and the resulting mixture was stirred for 30 minutes. l,2-Dichloro-4-methyl-5- nitrobenzene (0.059 mol) was added and the reaction mixture was stirred for 1 hour at 00C. The mixture was allowed to warm to room temperature for 1 hour and then cooled to 00C. A solution of hydrogen peroxide in water (30%) (17.8 ml) was added and air was bubbled through the solution overnight. The obtained mixture was slowly added dropwise to IN HCl (750 ml) and after stirring in ice-cold DIPE, the resulting precipitate was filtered off, yielding 5.83 g of intermediate (1).

According to the analysis of related databases, 75279-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2008/152081; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts