Category: nitriles-buliding-blocks

144649-99-0, name is 5-Bromo-2-methoxybenzonitrile, 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. Recommanded Product: 144649-99-0

Example 35 1,1-Dimethylethyl {[5-bromo-2-(methyloxy)phenyl]methyl}carbamate NaBH4 (2.9 g, 75.5 mmol) was cautiously added in several portions to a solution of NiCl2 (2.6 g, 19.8 mmol), Boc2O (8.2 g, 37.7 mmol) and 5-bromo-2-(methyloxy)benzonitrile (4.0 g, 18.9 mmol) in dry EtOH (70 mL) at 0 C. Once the reaction had subsided, the mixture was left to stir at room temperature for 3 h. Ethanol was removed under reduced pressure and the residue was dissolved in EtOAc and saturated solution of NaHCO3, then filtered and the aqueous layer was repeatedly washed with EtOAc. The combined organic phases were dried Na2SO4. The crude product was purified by flash column chromatography to give the captioned the product (1.5 g yield: 25%). 1H NMR (400 MHz, CDCl3) delta 7.36-7.33 (m, 2H), 6.74 (d, J=8.8 Hz, 1H), 4.97 (br, 1H), 4.27 (d, J=4.8 Hz, 1H), 3.82 (s, 3H), 1.45 (s, 9H); 13C NMR (400 MHz, CDCl3) delta 156.5, 155.8, 131.7, 131.1, 129.3, 111.8, 79.5, 55.5, 39.9, 26.4. HPLC: retention time.

The synthetic route of 144649-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US2009/203657; (2009); A1;,
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Application of 327-74-2,Some common heterocyclic compound, 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, molecular formula is C8H5F3N2, 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.

To a solution of 2-amino-5-cyanobenzotrifluoride (1.0g, 5.37mmol, 1 eq) and benzyl bromide (2.55ml_, 21 .5mmol, 4.0eq) in dry DMF (10ml_) was added at rt NaH (970mg, 21.5mmol, 4eq) portion-wise under Ar(g). The reaction mixture was stirred at rt overnight, and was then partitioned with H20 (30ml_) and extracted with EtOAc (5 x 20ml_) and CH2CI2 (20ml_). The combined organic extracts were dried over MgS04 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1 :0-9:1 ) to yield the product, 2, as a pale yellow solid (1 .66g, 85%).1H NMR (400MHz, CDCI3) deltaEta: 7.95 (d, J=2.0Hz, 1 H), 7.63 (dd, J=8.5, 1 .5Hz, 2H), 7.28-7.34 (m, 6H), 7.20 (d, J=6.5Hz, 4H), 7.12 (d, J=8.5Hz, 1 H), 4.23 (s, 4H).MS (ES+) 389.1 (100%, [M+Na]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-cyanobenzotrifluoride, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen, Joseph; SILVA, Franck, Alexandre; WO2011/135351; (2011); A1;,
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Electric Literature of 21803-75-8, A common heterocyclic compound, 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

A mixture of the product of step (a) (111 mg), Pd(OAc)2 (7 mg), BINAP (19 mg),cesium carbonate (120 mg) and 4-Amino-3-chloro-benzonitriIe (95 mg) in 15 ml toluene was reflaxed for 12 hours. The reaction mixture was eluted through a silica bed with Toluene and then with PE: EtOAc (1:1). The toluene fraction was discarded and the solvent of the PE:EtOAc fraction was removed under reduced pressure. The crude product was purified by Combiflash (linear gradient PE – THF). Yield 90 mg, 67 %. Finally, it was recrystallized from acetonitrile: water (1:1). Yield: 38 mg of colorless flakes.1H NMR (300 MHz3 CDC13, rt) delta 0.12 (m, 2H, CH2), 0.49 (m, 2H, CH2), 0.9 (m, IH, CH), 2.87 (dd, 2H, J= 5.7 Hz, J= 7.2 Hz, CH2) 4.735 (t, IH, J= 5.4 Hz, NH), 6.754 (s broad, IH, NH), 7.402 (d, IH, J= 8.7 Hz, ArH), 7.431 (dd, IH, J= 2.1 Hz, J= 8.6 Hz, ArH), 7.432 (dd, IH, J= 1.8 Hz, J= 8.7 Hz, ArH), 7.586 (d, IH, J= 1.8 Hz, ArH), 7.736 (d, IH, J= 1.8 Hz, ArH)3 and 8.21 (d, 2H, J= 8.7 Hz, ArH).MS: m/z 428.1 (M”)

The synthetic route of 21803-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMOS CORPORATION; WO2008/75353; (2008); 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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Oxocyclobutanecarbonitrile

a solution of 3-oxocyclobutane-1-carbonitrile (3.9 g, 41.01 mmol, 1.00 eq.) and 2-methylpropane-2-sulfinamide (4.97 g, 41.01 mmol, 1.00 eq.) in tetrahydrofuran (100 mL) was placed in a 250- mL 3-necked round-bottom flask and stirred for 16 hours at 70C. After cooled to room temperature, NaBH4 (780 mg, 20.53 mmol, 0.50 eq.) was added in portions and stirred for 30 mm at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with ethyl acetate and the organic layers combined. Theresulting mixture was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 7.5 g (9 1%) of N-(cis-3-cyanocyclobutyl)-2- methylpropane-2-sulfinamide as a yellow solid. LC-MS: (M+H) = 201.

According to the analysis of related databases, 20249-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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Application of 75279-55-9,Some common heterocyclic compound, 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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: Typical procedure exemplified by the synthesis of 2-amino-4-chlorobenzo-1-thiophene-3-carbonitrile (Table 1, entry 5a): To a N2 flushed, 500 mL, three necked round bottomed flask were added 2-chloro-6-fluorophenylacetonitrile (1e) (8.48 g, 50 mmol) and DMSO (100 mL). To the solution was added 60% sodium hydride (2.10 g, 52.5 mmol) portion wise under N2 at rt (slightly exothermic). After 30 min, the reaction mixture was cooled to 15C with cold water bath and O-ethyl carbonisothiocyanatidate (2) (5.65 mL, 50.0 mmol) was added drop wise. After 1 h, the reaction mixture was heated at 100C for 2 h. A solution of 5 N NaOH (50 mL) was added and the reaction mixture was stirred at 100C for 2 h. The suspension was cooled to rt with stirring and 700 mL of water was added. The mixture was then cooled to 15C. The suspension was filtered and house vacuum air dried for 18 h to give the crude product as ayellow solid (6.5 g).

The synthetic route of 75279-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krishnananthan, Subramaniam; Smith, Daniel; Traeger, Sarah C.; Mathur, Arvind; Li, Jianqing; Tetrahedron Letters; vol. 56; 24; (2015); p. 3766 – 3768;,
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Related Products of 2338-75-2, 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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compound 3 (0.85 g, 1.37 mmol) and 2-(p-tolyl)acetonitrile (0.45 g,3.43 mmol) were added into dry ethanol (75 mL), and then CH3ONa(0.19 g, 3.52 mmol) was added quickly. The mixture was refluxed withstirring for 6 h under an atmosphere of nitrogen. After cooling to roomtemperature, the resulting precipitate was collected by filtration, anddried under vacuum. The crude product was purified by column chromatography(silica gel, CH2Cl2/petroleum ether, v/v=3/1), affordinga yellow-green solid (1.03 g).

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)phenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Yonghui; Liu, Jingran; Yuan, Weiliang; Wang, Ying; Zhou, Hongke; Liu, Xingliang; Cao, Jianfang; Zhang, Chao; Dyes and Pigments; vol. 167; (2019); p. 135 – 142;,
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Related Products of 59997-51-2, These common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, 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 j03: At room temperature 4,4-dimethyl-3-oxopentanenitrile (J-II) (1 eq., 5 g) was taken up in EtOH (100 ml), mixed with hydrazine hydrate (2 eq., 4.42 g) and refluxed for 3 h. The residue obtained after removal of the EtOH by distillation was taken up in water (100 ml) and extracted with EE (300 ml). The combined organic phases were dried over sodium sulphate, the solvent was removed under vacuum and the product (J-III) (5 g, 89% yield) was obtained as a light red solid after recrystallisation from hexane (200 ml).

The synthetic route of 59997-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; US2012/115903; (2012); A1;,
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Synthetic Route of 1953-99-7,Some common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

To a 100 mL flask was added the solid (4- (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile (1.0 g), 3,4,5,6-tetrachlorophthalonitrile (0.22 g), 1,8-Diazabicycloundec- -ene (1.0 g), and 1-pentanol (10 mL), and dissolve by heating. Then, zinc acetate (0.15 g) is added and refluxed with heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography. Dichloromethane is appropriately added to the obtained solid to dissolve the solid, and hexane is added to crystallize. At this time, the obtained solid is filtered and vacuum dried to obtain a compound represented by the following formula (C).

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co.,Co.,Ltd; Kwon, Jae Young; Jung, Ju Ho; Lee, Yeon Soo; Lee, Jung Sun; Lee, Chang Ryul; (35 pag.)KR2016/22080; (2016); A;,
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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. 19472-74-3, name is 2-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 19472-74-3

To a solution of compound 5a (500 mg, 2.12 mmol) and 2-Bromophenylacetonitrile (538 mg, 2.76 mmol) in TMEDA (3 mL) and H2O (0.1 mL) was added Na2PdCl4 (6.23 mg, 0.02 mmol), CuI (7.62 mg, 0.04mmol) and 2-(Di-tert-butylphosphino)-1-phenylindole (13.5 mg, 0.04mmol). Under Ar, the mixture was warmed to 80 C and stirred for 3 h. After the mixture was cooled to warm temperature, water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 462 mg of compound 6 (yield: 62%) as a colorless liquid. 1H NMR (400 MHz, CDCl3): delta 7.50 – 7.44 (m, 2H), 7.38 (td, 1H, J = 7.6, 1.3 Hz), 7.30 (t, 1H, J = 7.5 Hz), 7.15 (t, 1H, J = 8.7 Hz), 6.78 – 6.70 (m, 2H), 4.93 (s, 2H), 3.72 (s, 3H), 3.79 (s, 2H), 2.95 – 2.89 (m, 2H), 2.60 (t, 2H, J = 7.6 Hz). MS (EI) m/z: 351 (M+).

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; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
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Application of 60899-34-5, 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. 60899-34-5 name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, 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 1-oxo-2,3-dihydro-JH-indene-4-carbonitrile INT-1 (42.5 g, 0.27 mol) and (R)-2-methylpropane-2-sulfinamide (36.0 g, 0.30 mol) in toluene (530 mL)was added titanium tetraethoxide (84.1 mL, 92.5 g, 0.40 mol) and the reaction mixture was heated at 60C for 12 h under N2. The crude (R)-N-(4-cyano-2,3-dihydro-1H- indene-1-ylidene)-2-methylpropane-2-sulfinamide INT-4 was used directly in the next experiment. LCMS-ESI (m/z) calculated for C14H16N20S: 260.3; found 261.1 [M+H],3.19 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; SCOTT, Fiona, Lorraine; MEADOWS, Kristen, R., Taylor; PEACH, Robert; (154 pag.)WO2018/64356; (2018); A1;,
Nitrile – Wikipedia,
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