Category: nitriles-buliding-blocks

Synthetic Route of 1021871-35-1, A common heterocyclic compound, 1021871-35-1, name is 3-Chloro-5-(hydroxymethyl)benzonitrile, molecular formula is C8H6ClNO, 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.

Step 4: 3-Chloro-5-cyanobenzyl carbonochloridate 3-Chloro-5-(hydroxymethyl)benzonitrile (25 g, 145 mmol) was dissolved in THF (200 mL). The resulting yellow solution was cooled to 10¡ã C. in an ice bath and treated dropwise with phosgene in toluene (152 mL, 289 mmol). The reaction mixture was stirred at ambient temperature for 16 hrs. The mixture was concentrated under reduced pressure and the crude material was diluted with toluene (200 ml) and re-concentrated under reduced pressure. The residue was purified by chromatography on silica (Redisep 340 g column on a Biotage system), eluting with EtOAc/iso-hexane to give 3-chloro-5-cyanobenzyl carbonochloridate as an oil. 1H NMR (600 MHz, CDCl3) delta 7.70 (1H, s), 7.66 (1H, s), 7.62 (1H, s), 5.32 (2H, s).

The synthetic route of 1021871-35-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Legrand, Darren Mark; Furminger, Vikki; Thomson, Christopher; Hughes, Owen Rhys; Stanley, Emily; US2014/171403; (2014); A1;,
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Related Products of 1897-52-5, These common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, 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.

Synthesis of compound 2.2. Compound 2.1 (5 g, 35.97 mmol, 1.00 eq), NH4C1 (2.11 g, 39.56 mmol, 1.1 eq) were suspended in toluene (100ml). A solution of trimethylaluminium (2.0 M, 19.5 ml, 39.56 mmol, 1.1 eq) was added dropwise to the above reaction mixture at room temperature. The mixture was stirred for one hour at ambient temperature and subsequently refluxed for 16 hours. After completion of the reaction, toluene was evaporated and residue was diluted with 10% methanol in CH2C12 (lOOmL). Silica gel (5.0 g) was added mixture and stirred for 30 minutes at ambient temperature. After 30 minutes, slurry was filtered and washed with CH2Cl2/methanol. The filtrate was concentrated under vacuum at 45 C to afford the crude material which was purified using trituration with 20% ethyl acetate in hexane (50ml). The solid obtained was filtered off and dried under vacuum to afforded pure compound 2.2 (4.5 g, 80.35 %). LCMS: 99.27%. MS (ES): m/z 157.0 (M+H)+.

The synthetic route of 1897-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
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These common heterocyclic compound, 72115-09-4, name is 5-Amino-2-bromobenzonitrile, 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. Formula: C7H5BrN2

5-amino-2-bromobenzonitriie (5.0 g, 25.4 mmoi), cyciopropyiboronic acid (4.36 g, 50.8 mmoi), cs2co3 (49.62 g, 152.3 mmoi), and tricyciohexyiphosphine (2.85 g, 10.2 mmoi) were weighed out and added to a large reaction tube with magnetic stir bar. Toiuene (120 mL) and water (40 mL) were added, and the reaction was subjected to yigorous sub-surface nitrogen sparging. Pd(OAc)2 (1.14 g, 5.1 mmoi) was weighed out and added, the tube was sealed under nitrogen, and the reaction was heated oyernight at 110 c. This was then filtered with water and ethyi acetate washings. The combined washings were treated with saturated aqueous NaHcO3 and the iayers were separated. The aqueous was extracted 4 more times with ethyi acetate, and the combined organie iayer was washed twice with brine and dried oyer sodium suifate. After filtration, concentration, and drying on the high yacuum, 7.65 g was obtained of 5-amino-2- cyciopropyibenzonitriie containing tricyciohexyiphosphine deriyed byproducts. This was used without further purification.

The synthetic route of 5-Amino-2-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; MCMURTRIE, Darren; KOLLURI, Rao; MASUDA, Esteban; TSO, Kin; ALVAREZ, Salvador; HECKRODT, Thilo; HOLLAND, Sacha; KELLEY, Ryan; DUNCTON, Matthew; SINGH, Rajinder; WO2014/89112; (2014); A1;,
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Application of 33279-01-5, 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. 33279-01-5, name is 3-Oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Preparation of 3-ethyl-l-(3-methylpyridm-2-ylHH-pyrazol-5-amine; EPO 3-Oxo-pentanenitrile (4.87 g, 26.10 mmol) and diphenylmethanone (3-methyl pyridin-2-yl)hydrazone (5.00 g, 17.40 mmol) were dissolved in anhydrous EtOH (150 mL). TsOH (3.31 g, 17.4 mmol) and cone. HCl (14.29 mL, 174.0 mmol) were added to the solution. The mixture was heated at reflux overnight. Additional 3-oxo-pentanenitrile (4.87 g, 26.10 mmol) was added. The mixture was refluxed another 24 h. EtOAc was added. The resulting mixture was basified by slow addition of sat. Na2CO3. The organic layer was dried over MgSO4 and then concentrated. Column chromatography purification (25% EtOAc/ hexane) afforded the title compound as a light yellow oil (1.5 g, 42.6%). 1H NMR (400 MHz, DMSO-d6) delta 8.35-8.34 (IH, d, J = 2.8 Hz), 7.86-7.84 (IH, d, J = 9.6 Hz), 7.39-7.36 (IH, t, J =4.5 Hz), 5.46 (IH, S), 2.58-2.52 (2H, q, J = 6.0 Hz), 2.30 (3H, s), 1.26-1.23 (3H, t, J = 4.2 Hz); LC-MS m/z 203.1 (MH+), HPLC RT (min) 1.07 {method (A)}.

The chemical industry reduces the impact on the environment during synthesis 3-Oxopentanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/27842; (2007); A1;,
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Reference of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

Step-1: 2-Fluoro-5-nitrobenzonitrile (1.4g, 1.0 eq, 8.4 mmol) was taken in annhydrous DMF (10 mL). Secondary amine (1.2 eq, 10.12 mmol) was added to the above solution followed by the addition of K2C03 (3.5g, 3.0eq, 25.3 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with EtOAc (100 mL) and partitioned with water (100 mL). Organic layers were separated and the aqueous layers were washed with EtOAc (1 x 50 mL). The combined oragnic layers were washed with aqueous staurated NaHC03 solution (100 mL) and dried over Na2S04. Organic layers were concentrated under reduced pressure to leave a crude mixture. The mixture was purified by column chromatography on silica gel (ISCO System) using EtOAc / Hexane (gradient system from 0: 1 to 2:8) as eluent to give the product as a solid. 2-(4-(Methylsulfonyl)piperazin-l-yl)-5-nitrobenzonitrile: Synthesized as described in Step-1. Yield = 73%, 1H NMR (300 MHz, CDC13) delta 8.43 (d, J = 2.1 Hz, 1H), 8.27 (dd, J = 9.3, 2.7 Hz, 1H), 6.98 (d, J = 9.3 Hz, 1H), 3.59 – 3.48 (m, 4H), 2.68 – 2.57 (m, 4H), 2.38 (s, 3H); LCMS (m z): 311 (M+H)+.

Statistics shows that 2-Fluoro-5-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 17417-09-3.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); 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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClFN

4-Chloro-2-fluoro-benzonitrile (8.0 g, 50.4 mmol), NaHS^FbO (50.4 mmol, 4.006 g) and DMF (30 mL) were stirred on an ice bath for 1 h. The mixture was partitioned between diethyl ether and HC1 (0.5 M), the organic phase was then extracted with NaOH (2 M, 50 ml) and the aqueous phase was concentrated a little, then acidified with HC1 which gave a precipitate that was isolated and dried to afford the title compound (5.1 g, 59 %). ‘H NMR (400 MHz, Chloroform-^) d 7.53 (d, j= 8.4 Hz, 1H), 7.43 (d, j= 1.7 Hz, 1H), 7.22 (dd, j= 8.4, 1.8 Hz, 1H), 4.15 (s, 1H).

The synthetic route of 57381-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; (118 pag.)WO2019/137971; (2019); 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. 1000339-52-5, name is 3-Fluoro-2-nitrobenzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

Synthesis of 3-((3,5-dimethylphenyl)amino)-2-nitrobenzonitrile To 3,5-dimethylaniline (3.9 g, 32.2 mmol) in THF (90 mL) was added sodium hydride (95% in mineral oil, 1.23 g, 48.9 mmol) and stirred for 1 hour. 3-Fluoro-2-nitrobenzonitrile (4.3 g, 25.9 mmol) was added and the reaction mixture was heated to reflux for about 16 hours. Reaction mixture cooled to room temperature, then water was added and filtered through silica gel, washed with 5% THF in hexane and concentrated in vacuo. The crude mixture was purified by flash column chromatography with 10% THF in hexane to give orange powder which was recrystallised with 10% 1,2-dimethoxyethane in hexane to give 3-((3,5-dimethylphenyl)amino)-2-nitrobenzonitrile (3.8 g, 55% yield) as an orange powder.

The synthetic route of 1000339-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universal Display Corporation; KWONG, Raymond; LAM, Sze Kui; LAM, Siu Tung; TSANG, Kit Yee; LEE, Chi Hang; SZIGETHY, Geza; (159 pag.)US2016/218303; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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 179897-89-3, Safety of 5-Bromo-2-fluorobenzonitrile

To 5-Bromo-2-fluoro-benzonitrile (10.05 g, 50.25 mmol) in DMSO (30 mL) is added sodiummethanethiolate (3.87 g, 55.27 mmol) portionwise at 0 C. The reaction mixture is stirred for 2 h at r.t. Sodiummethanethiolate (1.06 g, 15.07 mmol) is added and stirred for further 2 h at r.t. The reaction mixture is diluted with water (100 mL) and the precipitate is filtered off and dried in vacuo at 50 C. [0325] Yield 88% m/z 228/230 [M+H]+, rt 1.26 min, LC-MS Method V018_S01

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Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275159; (2014); A1;,
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Application of 75344-77-3, 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

4-Bromo-3,5-dimethyl benzonitrile (5.0 g) is dissolved in HCl in dioxane (4 M, 17.3 mL) and EtOH (5 mL) added. After stirring for 16 h volatiles are evaporated in vacuo and the crude residue (6.5 g) used as such in the next step.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3,5-dimethylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; FRATTINI, Sara; LINGARD, Iain; PETERS, Stefan; US2013/324514; (2013); A1;,
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These common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, 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. Quality Control of 4,5-Dichlorophthalonitrile

Compound 2 (1.5 g, 6.1 mmol) was dissolved in 40 mL anhydrous DMF. Anhydrous CsF (1.9 g, 12.2 mmol) was then added to the solution and the mixture was allowed to stir for 10 min at room temperature. A solution of 4,5-dichlorophthalonitrile (1.0 g, 5.1 mmol) in 10 mL anhydrous DMF was then added and the reaction mixture was stirred for 24 hrs at room temperature. After completion, the salt was filtered out using Buchner funnel and the crude mixture was diluted in 100 mL water and extracted with DCM (2¡Á50 mL). DCM was then concentrated under reduced pressure and the crude material was purified by column chromatography using (2:8) EtOAc/hexane solvent system as an eluent to obtain the desired product 5 as a white solid in 1.7 g (85% yield); mp is 106.2 C. Elemental analysis calculated (%) for C23H17ClN2O3: C, 68.23; H, 4.23; N, 6.92. Found: C, 68.03; H, 4.22; N, 6.78; FT-IR, numax/cm-1 3297.68, 2883.06, 2611.14, 2232.20; 1H-NMR (600 MHz, DMSO-d6, 25 0C): delta=2.38 (s, 3H), 3.33 (t, J=2.3 Hz, 2H), 4.02 (t, J=2.3 Hz, 4H), 4.32 (dd, J=10.9, 35.0 Hz, 4H), 7.09 (s, 1H), 7.35 (s, 2H), 8.47 (s, 1H); 13C-NMR (150 MHz, DMSO-d6, 25 0C): delta=20.5, 57.7, 77.2, 79.5, 108.5, 114.8, 114.9, 115.0, 119.9, 126.8, 130.0, 131.4, 135.6, 136.4, 146.6, 157.6; HRMS [M]+ calcd for C23H7ClN2O3: 404.0928, found: 404.0922.

The synthetic route of 4,5-Dichlorophthalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KUWAIT UNIVERSITY; MAKHSEED, SAAD A.; HUSAIN, ALI A.; GANESAN, ASAITHAMPI; DURMUS, MAHMUT; US2020/102267; (2020); A1;,
Nitrile – Wikipedia,
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