Author: Jessica.F

Synthetic Route of 143879-78-1, These common heterocyclic compound, 143879-78-1, name is 3-Amino-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.

Methyl (3 S)-3 ,7-dimethyl- 1,1 -dioxo-2,3 ,4,5 -tetrahydropyrrolo [3 ,4-f]thiazepine-6- carboxylate (200 mg, 0.73 mmol) and 3-amino-2,6-difluoro-benzonitrile (0.16 g, 0.88 mmol) in dry THF (5 mL) was treated with lithium bis(trimethylsilyl)amide (2.2 mL, 1 M in THF, 2.2 mmol) and this was stirred overnight at room temperature. Theresulting mixture was quenched with NH4C1 (aq., sat., 5 mL). Then 5 mL of brine wasadded and the layers were separated. The water layer was extracted using EtOAc (2 X30 mL). The combined extracts were concentrated in vacuo and the obtained crude waspurified using silica gel column chromatography (gradient elution: EtOAc:heptane0:100 to 100:0). The desired fractions were concentrated in vacuo and the obtainedresidue was purified via preparative HPLC (Stationary phase: RP XBridge Prep C18 OBD-l0jim, 3OxlSOmm, Mobile phase: 0.25% NH4HCO3 solution in water, ACN). The desired fractions were concentrated under reduced pressure, co-evaporated with methanol (2 X 25 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 157 (7.6 mg). ?H NMR (400 MHz, DMSO-d6) oe ppm 1.14 (d, J=6.82 Hz,3H)1.31-1.45(m,1H)1.81-1.91(m,1H)2.77-2.89(m,1H)3.07-3.18(m,1H)3.58 – 3.67 (m, 1 H) 3.70 (s, 3 H) 7.03 (d, J=9.68 Hz, 1 H) 7.40 – 7.51 (m, 2 H) 8.06(td,J=8.97, 6.05 Hz, 1 H) 10.31 (s, 1 H); Method B; Rt: 0.85 mi mlz :393 (M-H)Exact mass: 394.1, MP: 247.5 C.

The synthetic route of 143879-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VENDEVILLE, Sandrine, Marie, Helene; LAST, Stefaan, Julien; DEMIN, Samuel, Dominique; GROSSE, Sandrine, Celine; HACHE, Geerwin, Yvonne, Paul; HU, Lili; PIETERS, Serge, Maria, Aloysius; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; (244 pag.)WO2017/1655; (2017); A1;,
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Application of 64248-64-2, The chemical industry reduces the impact on the environment during synthesis 64248-64-2, name is 2,5-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Step A: 5-Fluoro-2-hydroxybenzonitrile (23t): 2,5-Difluorobenzonitrile (14.9 g, 107 mmol) and benzyl alcohol (11.1 mL, 11.6 g, 107 mmol) were dissolved in DMF (330 mL) and cooled to 0 C. Sodium hydride (60% in oil, 6.40 g, 161 mmol) was added to the solution at 0 C. and the reaction mixture was allowed to warm to room temperature. After stirring for 1 hour at room temperature, the reaction solution was cooled to 0 C. and water (330 mL) was gradually added to the solution. The mixture was transferred to a separatory funnel and extracted 3 times with 500 mL of Et2O. The combined organic layer was washed with 100 mL of water twice, brine once, then dried over MgSO4. After filtration, the solution was concentrated under reduced pressure to obtain a crude pale yellow solid. The crude solid was dissolved in MeOH (500 mL). To the solution was added 10% palladium on activated carbon under a nitrogen atmosphere. Replacing nitrogen gas with hydrogen gas, reaction mixture was stirred at room temperature (if the reaction did not proceed in 30 minutes, the palladium on carbon was filtered off and set up again). After 2 hours of stirring, the palladium on carbon was filtrated off and washed with MeOH. The solution was concentrated under reduced pressure to obtain a pale yellow solid. The solid was recrystallized from hot toluene (100 mL) by addition of hexane (10 mL) followed by cooling to 0 C. The obtained white needles were washed with 1:1 mixture of toluene and hexane (7.23 g, 49% yield). The mother liquor was concentrated and purified on silica gel with Et2O/hexane (2:3-1:1) to afford desired compound (23t) (6.94 g, 47% yield). Total 14.2 g (96% yield) over 2 steps. 1H-NMR (400 MHz, d6-DMSO) delta 11.09 (s, 1H), 7.58 (dd, J=8.4, 3.2 Hz, 1H), 7.40 (td, J=8.6, 3.2 Hz, 1H), 7.03 (dd, J=9.2, 4.4 Hz, 1H) ppm.

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, 2,5-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Munson, Mark; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; US2004/180896; (2004); A1;; ; Patent; Munson, Mark; Mareska, David A.; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; Harvey, Darren; US2004/192653; (2004); A1;,
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67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 67515-59-7

A mixture of 4-fluoro-3-trifluoromethylbenzonitrile (75 mg, 0.40 mmol), sodium sulfinate (44.5 mg, 0.44 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 100 C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water. The resulting white solid was collected via filtration, washed with cold water, dried in a vacuum oven to give 4-methanesulfonyl-3-trifluoromethyl-benzonitrile (90 mg, 90% yield). This benzonitrile was hydrogenated in 2N NH3 in methanol with 35 mg of Raney Ni under a hydrogen balloon for 2 h. The reaction mixture was filtered through a celite plug, washed with methanol, evaporated in vacuo to give the titled compound.

The synthetic route of 67515-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Gang; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Liu, Mei; US2006/173050; (2006); A1;,
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Application of 874-97-5, 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.

3-[(5-Amino-2H-pyrazol-3-yl)oxymethyl]benzonitrile, used as starting material, was prepared as follows: a) 3-Amino-5-hydroxypyrazole (2 g, 20.18 mmol, 1 eq) and triphenylphosphine (6.36 g, 24.22 mmol, 1.2 eq) were stirred in DCM (20 ml) for 30 mins. After this time, DIAD (4.77 ml, 24.22 mmol, 1.2 eq) was slowly added, keeping the temp below 20 C. with a water bath, and the resulting mixture stirred for a further 45 mins. A solution of 3-cyanobenzyl alcohol (3.23 g, 24.22 mmol, 1.2 eq) in DCM (10 ml) was added slowly and the reaction left to stir at RT for 24 hours. After this time the solid was filtered off and the solution extracted with 2M HCl solution (3×30 ml). The aqueous layer was back-washed with diethyl ether (2×30 ml), then basified to pH 9 using ammonium hydroxide, cooling the mixture to avoid a strong exotherm. The solution was extracted with DCM (3×30 ml) and the organic fractions combined, dried over magnesium sulphate and concentrated to give 3-[(5-amino-2H-pyrazol-3-yl)oxymethyl]benzonitrile as a colourless gum (321 mg, 7%). MS: m/z 215 (MH+)

Statistics shows that 3-Cyanobenzyl alcohol is playing an increasingly important role. we look forward to future research findings about 874-97-5.

Reference:
Patent; ASTRAZENECA AB; US2008/4302; (2008); 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Methylamino)acetonitrile hydrochloride

REFERENCE SYNTHETIC EXAMPLE 41 2-(Methyl{[trans-4-(3-methyl-4-oxo-7-{[2-(trimethylsilyl)ethoxy]methyl}-2,3,4,7-tetrahvdro-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-1-yl)cyclohexyl]methyl}amino)acetonitrile To a solution of trans-4-(3-methyl-4-oxo-7-{[2-(trimethylsilyl)ethoxy]methyl}-2,3,4,7-tetrahydro-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-1-yl)cyclohexanecarbaldehyde (25 mg, 0.056 mmol) obtained in Reference Synthetic Example 29 in methanol (0.5 mL), methylaminoacetonitrile hydrochloride (7.8 mg, 0.073 mmol) and 2-picoline borane (8.1 mg, 0.073 mmol) were added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was mixed with 1 M aqueous sodium hydroxide and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel thin-layer chromatography (ethyl acetate/2-propanol=9/1 (v/v)) to obtain the title compound as a colorless oil (27.5 mg, yield: 99percent).

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; Nissan Chemical Industries, Ltd.; TAKAHASHI, Keiji; WATANABE, Tsuneo; HAYASHI, Keishi; KURIHARA, Kazunori; NAKAMURA, Takanori; YAMAMOTO, Akio; NISHIMURA, Takuya; KAMIYAMA, Toshihiko; HIDAKA, Yuuki; EP2955181; (2015); A1;,
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Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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: C12H6N2O

To a three-necked round bottom flask were added 5,5′-(9,9′-spirobi[fluorene]-20,7-diyl)bis(4-(2-ethylhexyl)thiophene-2-carbaldehyde) (205 mg, 0.27 mmol), 1,1-dicyanomethylene-3-indanone (430 mg, 2.2 mmol), chloroform (50 mL), and 0.9 mLpyridine. The mixture was deoxygenated with nitrogen for 30 minand then refluxed for 12 h. After cooling down to room temperature,the mixture was poured into methanol (200 mL) and filtered.The residue was purified by column chromatography on silica gelusing petroleum ether/dichloromethane (1:1) as eluent yield anorange solid (207 mg, 69%). 1H NMR (400 MHz, CDCl3): delta 8.77 (s,2H), 8.68 (d, J 6.9 Hz, 2H), 7.96 (s, 1H), 7.93 (d, J 2.7 Hz, 2H), 7.89(d, J 4.8 Hz, 2H), 7.86 (d, J 1.8 Hz, 1H), 7.76 (m, 4H), 7.61 (d,J 5.4 Hz, 4H), 7.45 (t, J 7.5 Hz, 2H), 7.21 (t, J 7.5 Hz, 2H), 6.92 (s,2H), 6.82 (d, J 7.5 Hz, 2H), 2.39 (d, J 6.9 Hz, 4H),1.42 (m, 2H),1.09(m, 16H), 0.75 (m, 6H), 0.59 (t, J 6.9 Hz, 6H). 13C NMR (100 MHz,CDCl3): delta 188.63, 161.13, 157.22, 149.46, 149.27, 148.30, 143.36,141.49, 141.22, 140.47, 138.67, 137.35, 135.67, 135.47, 135.10, 133.58,130.17, 129.32, 128.84, 125.88, 125.17, 124.72, 124.37, 123.20, 121.23,121.15, 115.08, 114.99, 70.28, 66.57, 40.64, 32.95, 32.60, 28.90, 25.88,23.49, 14.65, 10.92. MS (MALDI): m/z calcd for C75H60N4O2S2 H:1114.4; found: 1114.1. Anal. Calcd for C75H60N4O2S2: C, 80.90; H,5.43; N, 5.03. Found: C, 80.77; H, 5.58; N, 5.33.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1080-74-6, its application will become more common.

Reference:
Article; Wang, Jiayu; Dai, Shuixing; Yao, Yuehan; Cheng, Pei; Lin, Yuze; Zhan, Xiaowei; Dyes and Pigments; vol. 123; (2015); p. 16 – 25;,
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Related Products of 555-21-5,Some common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, molecular formula is C8H6N2O2, 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-4 The following example illustrates the hydrogenation of various nitroaromatics as mentioned in Table 4. The hydrogenation of exemplary nitroaromatics was conducted under the following conditions. The procedure was similar to that for biphasic reactions [reaction numbers 7- 10, Table 2] Reaction conditions: Pressure: 400 psi; Temperature: 423K; Aqueous phase: 9×10-5 m3 ; Organic phase consists of neat substrate; catalyst FeS04. 7H20 : 7. 2×10-5 mol ; Fe: EDTANa2 1: 5; conversion in all cases was complete ; TOF calculated as mols of nitro compound converted per mol of Fe, § based on GC analysis. Table 4 Reaction No Substrate Substrate Yield of TOF (mols) corresponding hr~’ amine % 16 Nitrobenzelle 0. 090 98. 5 529 17 2-nitrotoluene 0. 0849 98. 75 457 18 2, 4-dinitrotoluene 0. 056 84. 63 134 19 4-nitrochlorobenzene 0.0635 96. 2 434 20 3-nitrochlorobenzene 0. 0635 99 400 21 2-nitrotoluene 0. 0849 98. 75 462 22 2-nitroanisole 0. 0820 89. 19 450 23 2-nitroaniline 0.0725 98. 2 116 24 4-nitrobenzoic acid 0.0598 85.8 393 25 4-nitro acetophenone 0.06 99 208 26 4-nitro benzylnitrile 0. 061 90 99

The synthetic route of 555-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; WO2005/70869; (2005); A1;,
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Synthetic Route of 6136-68-1,Some common heterocyclic compound, 6136-68-1, name is 3-Acetylbenzonitrile, molecular formula is C9H7NO, 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.

Br2 (1 mmol) was dropwise added to a solution of 3-acetylbenzonitrile (1 mmol) in Et2O (15 ml) at 0 C., and then the mixture was stirred at r.t. for 4 h. Water was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and was concentrated to give an oil, i.e., 3-(2-bromoacetyl)benzonitrile, which was directly used for the next step without purification.

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

Reference:
Patent; Hutchison Medipharma Enterprises Limited; US2009/118292; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 186517-05-5, name is 2,3-Difluoro-6-(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 186517-05-5, Computed Properties of C8H2F5N

Example 13 2,3-difluoro-6-trifluoromethylbenzaldehyde (Compound No. 44) STR30 2.0 g of 2,3-difluoro-6-trifluoromethylbenzonitrile was dissolved in 20 ml of anhydrous dichloromethane and the resultant solution was cooled down to -78 C. under a nitrogen atmosphere. To the solution was then gradually added dropwise with 7.1 ml of 1.5 M toluene solution of diisobutyl aluminium hydride (DIBAL) over 30 minutes. After stirring the solution at -78 C. for 1 hour, the solution was allowed to room temperature. The solution was then added with 7 ml of saturated aqueous solution of ammonium chloride, stirred for 30 minutes and subsequently added with 33 ml of 5% sulfuric acid. The mixture was then extracted with ether, and the organic layer obtained was washed with saturated saline solution and was then dried over anhydrous magnesium sulfate. After a process for the concentration, the organic solution was purified by using silica gel column chromatography to obtain 1.36 g of the title compound (nD 20.6-1.4357). The aldehyde compound obtained here was easily oxidized if it is left in the air and was converted to the corresponding benzoic acid (Compound No. 14).

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, 2,3-Difluoro-6-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Soda Co., Ltd.; US6054605; (2000); A;,
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Electric Literature of 13726-21-1, 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. 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

KOtBu (370 g, 3.3 mol) was dissolved in THF (1.7 L) and stirred at -20 C. After 30 min, to the reaction mixture was added 2-(4-chloro-3-methoxyphenyl)acetonitrile (13) (240 g, 1.32 mol) in THF (0.5 L) and then the resulting mixture was stirred for additional 30 min at the same temperature. CH3I (563 g, 3.96 mol) was added and the mixture was slowly warm to room temperature over 2 h with mechanical stirring. The reaction mixture was quenched with water in ice-bath and extracted with EtOAc (1.5 L x 2). The combined organic layers were washed with brine (3 L), dried over anhydrous MgS04, filtered and concentrated under reduced pressure to give 2-(4-chloro-3-methoxyphenyl)-2-methylpropanenitrile (14) as a amber liquid (269 g, 97%). 1H NMR (400MHz, CDC13): delta 7.35-7.37 (d, 1H), 7.05 (s, 1H), 6.95-6.97 (d, 1H), 3.94 (s, 3H), 1.72 (s, 6H).

The chemical industry reduces the impact on the environment during synthesis 2-(4-Chloro-3-methoxyphenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WO2011/71565; (2011); A1;,
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