Tag: M.W=200-300

1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

Compound 3 was synthesized according to the reported procedure[27]. To the solution of tetrachlorophthalonitrile (1) (2 g,7.5 mmol) in anhydrous DMF (15 ml), 3-(diethylamino)phenol (2)(1.24 g, 7.5 mmol) was added. The reaction was allowed to stir for15 min, and finely powdered anhydrous Na2CO3 (1.59 g, 15 mmol)was added in portions to the reaction mixture over 1 h with efficientstirring. Then, the mixture was stirred at 30 C for 3 h. After3 h, the reaction was cooled to room temperature, poured into icecoldwater, extracted with ethyl acetate, washed with 1 M NaOHandwashed with a brine solution. The organic layerwas dried usingNa2SO4, and the solvents were evaporated to obtain the crudeproduct. The crude product was purified by column chromatographyusing hexane-ethyl acetate (90:10) as eluent. Yield (1.9 g65percent), 1H NMR (CDCl3, 300 MHz) d, 6.99 (t, J 8.4 Hz, 1H), 6.38 (dd,J 8.4 & 2.1 Hz, 1H), 6.22 (t, J 2.1 Hz, 1H), 5.68 (dd, J 7.8 & 1.5 Hz,1H), 3.26 (q, J 6.9 Hz, 4H) 1.10 (t, J 2.1 Hz, 6H) (Fig. S1), 13C NMR(CDCl3, 75 MHz) 155.9, 152.8, 148.6, 136.2, 135.3, 132.1, 129.2, 115.7,113.6, 110.8, 106.7, 99.1, 98.03, 43.4, 11.4 (Fig. S2). FT-IR (KBr pellet)(g, cm1) 2980 (AreCeH) 2920e2880 (Aliphatic-C-H), 2235 (C^N),1280 (CeOeC) (Fig. S3). LC-MS: m/z 396 [M2] (Fig. S4).

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

Reference:
Article; Muthukumar, Palanisamy; Kim, Hak-Soo; Jeong, Jong Woo; Son, Young-A.; Journal of Molecular Structure; vol. 1119; (2016); p. 325 – 331;,
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A common compound: 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 114897-91-5

(2) Production of ethyl (4-bromo-2-fluorophenyl)acetate: Hydrochloric acid (10 mL) was added to an ethanol solution (20 mL) of (4-bromo-2-fluorophenyl)acetonitrile (2.11 g, 9.86 mmol), and heated under reflux for 15 hours. Next, with cooling with ice, aqueous saturated sodium hydrogencarbonate solution was gradually added to the reaction liquid for neutralization. After extracted with ethyl acetate, the obtained organic layer was washed with saturated saline, then dried with anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure, then the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:0 to 9:1) to obtain the entitled compound (1.81 g, 70 %). 1H-NMR (400 MHz, DMSO-d6, delta ppm): 1.26 (3H, t, J=7.2 Hz), 3.62 (2H, s), 4.17 (2H, q, J=7.2 Hz), 7.12-7.18 (1H, m), 7.23-7.28 (2H, m).

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, 114897-91-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1916239; (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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., 1813-33-8

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

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; 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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179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-bromo-5-fluorobenzonitrile (LXVI) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20C. Then it was stirred at 80C for 2 h, HC1 (6 N, 100 mL) was added to the mixture slowly at 20C. The mixture was stirred at 80C for 1 h, then it was washed with EtOAc (300 mL). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL x 3). The combined organic layers were dried over anhydrous Na2504 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (LXVII) (24.0 g, 117.62 mmol, 53.5% yield). ?H NMR (CDC13, 300 MHz) ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, 1H), 7.12 (d, J=8Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN mlz 203.9 (Br79M+H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23993; (2017); A1;,
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A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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. 1953-99-7.

.60 g (0.015 mol) of sodium hydroxide was added to a solution of 1.64 g (0.0075 mol) of 2,6-dichloro-4-nitroaniline in 40 mL of DMF, followed by addition of 2 g (0.0075 mol) of 3,4,5,6-tetrachlorophthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90¡ã C.)=1:4, as an eluent) to give 2.8 g of compound A-44 as yellow solid, m.p. 188-190¡ã C. [0129] 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3), delta (ppm): 6.76 (s, 1H, NH), 8.31 (s, 2H, Ph-3,5-2H).

The synthetic route of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.; SINOCHEM CORPORATION; Liu, Changling; Huang, Guang; Lan, Jie; Hao, Shulin; Li, Zhinian; Li, Huichao; Guan, Aiying; Jiang, Airu; Xu, Ying; US2014/213598; (2014); A1;,
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1953-99-7, 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. 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3,4,5,6-Tetrachlorophthalonitrile (10 g), Potassium carbonate (10 g), Dodecane thiol (10 g) and Tetrahydrofuran (100 ml) were added to a 500 ml flask and reacted at room temperature for 2 hours.After completion of the reaction, the reaction mixture was filtered and vacuum distilled, and then hexane (100 mL) was added thereto for purification and filtration to obtain 4-dodecathio-3,5,6-trichlorophthalonitrile (11 g).

The synthetic route of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SD I Co., Ltd.; Park, In Kul; Kim, Hyung Mook; Park, Chae Won; Sin, Myung Yeop; Lee, Young Gi; Jung, Uii Soo; (31 pag.)KR2016/47824; (2016); A;,
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691877-03-9, A common heterocyclic compound, 691877-03-9, name is 3-Bromo-5-(trifluoromethyl)benzonitrile, molecular formula is C8H3BrF3N, 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.

In a 20-mL glass tube equipped with a screw cap, were placed o-CP-2Cz (0.39 g), NaOtBu (0.39 g), and Pd-XPhos-OMs (0.097 g). The tube was then capped and evacuate/refill with argon three times. 0.53 mL of 1-Br-3-CN-5-CF3-C6H3 and 4.0 mL of anhydrous 1,4- dioxane were filled in under argon. The mixture was stirred at 110 C for 16 h. For work- up, the mixture was diluted with DCM and filtered through silica gel. After removing the volatiles, flash chromatography (gradient 0 to 20% DCM in hexanes) was used to purify the product. Yield: 0.41 g, 51%.

The synthetic route of 691877-03-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; BUCHWALD, Stephen, L.; HUANG, Wenliang; (89 pag.)WO2016/196885; (2016); A1;,
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79463-77-7, 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 79463-77-7 as follows.

A solution of 5-amino-2-[(pyrrolidin-1-yl)methyl]benzoxazole (200 mg, 0.92 mmol) and diphenylcyanocarbonimidate (263 mg, 1.10 mmol) in isopropyl alcohol (3.5 mL) was stirred overnight at ambient temperature, the resulting white solid product, (Z)-phenyl /V- cyano-/V-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)carbamimidate, was filtered and used directly for the next step (290 mg, 87%).

According to the analysis of related databases, Diphenyl N-cyanocarbonimidate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2008/83354; (2008); A1;,
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1813-33-8, Adding a certain compound to certain chemical reactions, such as: 1813-33-8, name is 2-Chloro-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 1813-33-8.

General procedure: Appropriate ROH (3.00 mmol) was added topotassium tert-butoxide (3.00 mmol) solution in toluene (7 ml).1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 3ml)was added to the mixture and stirred for 30 min at 80 C. Aftercooled down to ambient temperature of the reaction mixture,2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) in toluenewas dropwise and stirred for 3 h at 80 C. The reaction wasquenched by adding water and extracted with EtOAc twice. Thecombined organic extracts were dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:7) eluantcondition.

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-Chloro-4-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

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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A common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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. 79463-77-7.

To a solution of N-(2-dimethylaminoethyl)-2,5-dimethoxybenzene 1,4-diamine hydrochloride (0.05g, 0.143mmol) in distilled water (1mL) was added K2CO3 (0.065g, 0.47mmol). This was diluted with EtOAc (1mL) and diphenylcyano-carbonimidate (0.032g, 0.136mmol) was added. The reaction was stirred at RT for 18h. The precipitate was filtered and washed with minimal EtOAc to give the title compound as a light purple solid (0.015g, 29% yield). 1H-NMR (500 MHz, DMSO-d6) 10.11 (s, 1H), 7.51-7.33 (m, 2H), 7.31-6.98 (m, 3H), 6.81-6.64 (m, 1H), 6.28 (br s, 1H), 4.87 (br s, 1H), 3.85-3.62 (m, 5H), 3.12 (s, 3H), 2.17 (s, 6H) ppm; LC-MS 384.3 (M+H); HPLC 1.9 min(method A).

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/46120; (2004); A2;,
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