Month: April 2021

75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, 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. category: nitriles-buliding-blocks

Step 1 : Synthesis of 4-cyano-2,6-dimethylphenylboronic acid pinacol ester First, 5.0 g (24 mmol) of 4-bromo-3,5-dimethylbenzonitrile, 7.3 g (29 mmol) of bis(pinacolato)diboron, 8.4 g (86 mmol) of potassium acetate, and 120 mL of dimethyl sulfoxide (DMSO) were put into a three-neck flask, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 0.20 g (0.24 mmol) of [l, l’-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct and 0.20 g (0.48 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and the mixture was heated and stirred at 90 C for 7 hours. To this mixture were further added 0.20 g (0.24 mmol) of [l,l’-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct, 0.20 g (0.48 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 3.5 g (14 mmol) of bis(pinacolato)diboron were further added to, and the mixture was heated and stirred at 100 C for 17 hours to be reacted. Water was added to the reacted solution to separate the solution into an organic layer and an aqueous layer, and the aqueous layer was subjected to extraction with toluene. A solution obtained by combining the organic layer and the solution of the extract was washed with water and saturated saline, and anhydrous magnesium sulfate was added thereto for drying. The obtained mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. This solid was purified by flash column chromatography. As developing solvents, first, a mixed solvent of toluene and ethyl acetate in a ratio of 10: 1 (v:v) was used, and then a mixed solvent of toluene and ethyl acetate in a ratio of 5: 1 (v:v) was used. The obtained fraction was concentrated to give a solid. This solid was washed with toluene and hexane, so that 3.5 g of a white solid was obtained in a yield of 57 %. The obtained white solid was identified as 4-cyano-2,6-dimethylphenylboronic acid pinacol ester by nuclear magnetic resonance ( MR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-9) below.

The synthetic route of 75344-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; SEO, Satoshi; WATABE, Takeyoshi; INOUE, Hideko; YAMADA, Yui; MITSUMORI, Satomi; TAKAHASHI, Tatsuyoshi; HARA, Tomoka; (444 pag.)WO2016/203350; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, 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 20249-16-5, category: nitriles-buliding-blocks

Example 59A 3,3-Difluorocyclobutanecarbonitrile Under argon, 14.57 g (153.2 mmol) of 3-oxocyclobutanecarbonitrile from Example 58A were initially charged in 200 ml of absolute dichloromethane, 40.48 ml (306.4 mmol) of diethylaminosulphur trifluoride dissolved in 50 ml of dichloromethane were added at 0 C. and the mixture was stirred at RT overnight. A little at a time, the reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, cooled to 0 C., and stirred for 30 minutes. The organic phase was separated off and the aqueous phase was extracted with 200 ml of dichloromethane. The combined organic phases were twice washed with water, dried over sodium sulphate, filtered and concentrated. This gave 15.2 g (85% of theory) of the title compound. GC-MS (Method H): Rt=1.43 min MS (ESpos): m/z=98 (M-F)+

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, 3-Oxocyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; VALOT, Gaelle; FOLLMANN, Markus; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; DIETZ, Lisa; LI, Volkhart Min-Jian; RAY, Nicholas Charles; BACHERA, Dominika; (71 pag.)US2017/50961; (2017); A1;,
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Related Products of 16588-02-6, 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. 16588-02-6 name is 2-Chloro-5-nitrobenzonitrile, 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.

General procedure: To solution of 1.97 mmol (1.2 eq.) of phenol 2-8, 12-13 in 3 ml dry DMSO was added 79 mg(1.2 eq.) powdered NaOH. The mixture was heated at 50C for 20 min and to the formed clearsolution 0.300 g (1.64 mmol, 1.0 eq.) of 1 was added. The reaction mixture was heated at 80C for 8h. After cooling 40 ml water was added and extracted with DCM. The organic phase was washedwith aq. NaHCO3 and water, dried over Na2SO4, filtered and evaporated in vacuo. The crudeproducts 14-20, 24-25 were purified by column chromatography (50 g silica-gel). After column theformed solid products were powdered, washed with 3 ml hot hexane and dried in vacuo.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Dobrikov, Georgi M.; Slavchev, Ivaylo; Nikolova, Ivanka; Stoyanova, Adelina; Nikolova, Nadya; Mukova, Lucia; Nikolova, Rosica; Shivachev, Boris; Galabov, Angel S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 19; (2017); p. 4540 – 4543;,
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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. 3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(2,6-Dichlorophenyl)acetonitrile

4-Methylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (22.00 g, 120.1 mmol) and 2, 6-DICHLOROPHENYLACETONITRILE (26.90 g, 144.6 mmol) were added to a dry 1 L three- necked flask equipped with an overhead stirrer. The solids were dissolved in 125 mL of dry DMF. The pale yellow solution turned slightly orange upon addition of 70 g (506 mmol) OF K2C03. The reaction was heated to 100C and stirred for 18 hours at this temperature. The reaction became dark reddish-orange in color. The flask was cooled to 50C and the resulting precipitate was filtered. The pink solid was washed with 100 mL of 3: 1 DMF/water. After vacuum drying, 13.45 g (32 %) OF 6- (2, 6-dichloro-phenyl) -8- METHYL-2-METHYLSULFANYL-8H-PYRIDO [2, 3-d] pyrimidin-7-ylideneamine were obtained. The spectral data matched literature values.

The synthetic route of 3215-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; WO2004/63195; (2004); A1;,
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Application of 60702-69-4, These common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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.

Combine the compound from Example 218 step 2 (692 mg, 2.12 mmol) and K2CO3 (323 mg, 2.33 mmol) in DMF (9 mL), stir the mixture at room temperature for 30 min and then add 2-chloro-4-fluoro-benzonitrile (330 mg, 2.12 mmol), and heat at 100 C overnight. Cool to ambient temperature and pour into water. Extract the aqueous layer with EtOAc. Dry the organic layer over NA2SO4 and eliminate the solvent. Purify by flash chromatography on silica gel (eluent: ETOAC/HEXANE 15/85) to obtain the title compound (940 mg, 95%). Electrospray MS M-1 ion = 461, H-NMR (CDC13, 400 MHz): 7.57 (d, 1H, J= 7.8 Hz), 7.36-7. 13 (m, 7H), 7. 00-6. 85 (m, 4H), 4.44-4. 36 (M, 2LI) 3.49-3. 32 (m, 2H), 2.83-2. 73 (m, 2H), 1.51-1. 43 (m, 9H).

Statistics shows that 2-Chloro-4-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 60702-69-4.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/26305; (2004); A1;,
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Reference of 1953-99-7, These common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

(i) Preparation of 1,2-dicyano-3,4,5,6-tetraphenoxybenzene A mixture of 1,2-dicyano-3,4,5,6-tetrachlorobenzene (50 parts), phenol (106 parts), potassium carbonate (104 parts) and dimethylformamide (200 parts) was stirred and heated at 70¡ã C. for 2 hours before pouring into water (500 parts). The aqueous mixture was extracted with chloroform (2*300 parts). The chloroform extract was washed with a 5percent aqueous solution of sodium hydroxide (2*250 parts) and then with water (2*250 parts). The chloroform extract was dried over anhydrous magnesium sulphate, filtered and the chloroform was removed by distillation under reduced pressure to leave a brown oil. The brown oil was dissolved in hot butan-1-ol and allowed to cool slowly. 1,2-Dicyano-3,4,5,6-tetraphenoxybenzene (62.2 parts, 67percent) was obtained as a pale yellow solid m.p. 149¡ã-151¡ã C.

Statistics shows that 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile is playing an increasingly important role. we look forward to future research findings about 1953-99-7.

Reference:
Patent; Zeneca, Limited; US5486274; (1996); A;; ; Patent; Zeneca Limited; US5484915; (1996); A;,
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Adding a certain compound to certain chemical reactions, such as: 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, 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 59997-51-2, Computed Properties of C7H11NO

Step j03: At room temperature 4,4-dimethyl-3-oxopentanenitrile (J-II) (1 equivalents, 5 g) was taken up in ethanol (100 mL), mixed with hydrazine hydrate (2 equivalents, 4.42 g) and refluxed for 3 h. The residue obtained after removal of the ethanol by distillation was taken up in water (100 mL) and extracted with ethyl acetate (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 n-hexane (200 mL).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,4-Dimethyl-3-oxopentanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68462; (2013); A1;,
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Synthetic Route of 13388-75-5, 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 13388-75-5 as follows.

General procedure: A 50 mL round-bottomed flask was charged with 3 (0.177 g, 1 mmol), aromatic aldehyde or substituted aromatic aldehyde (1 mmol) and 10 mL methanol with stirring, and the mixture was heated to 60 C. After 30 min, sodium methoxide (0.027 g, 0.5 mmol) was added to the mixture and keep the temperature for 4-6 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to RT, and the precipitate was separated by filter and recrystallized from methanol to give 4a-4z and 5a-5d.

According to the analysis of related databases, 13388-75-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ma, Jun; Li, Jiajun; Tian, Yu-Shun; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 81 – 85;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-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 36282-26-5, name: 2-Bromo-4-fluorobenzonitrile

5,4′-Difluoro-biphenyI-2-carbonitrie (CAB06058)A mixture of 2-bromo-4-fiuorobenzinitrile (5.0 g, 25.0 mmol), 4-fiuorophenylboronic acid (3.85 g,27.5 mmol), dimethoxyethane (30 rtiL) and 2M Na2CO3 (40 mL) was heated to reflux before Pd2(dba)3 (0.10 g) was added and heating was continued for 5 hours. After cooling to room temperature CHCl3 (50 mL) was added to and the mixture was filtered (celite). The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography [SiO2, CHCl3] followed by recrystallisation from CHCl3/n-hexane to afford CAB06Theta58 (4.03 g, 71%) as colorless needles. Mp. 111-113 C; 1H NMR (400 MHz, CDCl3) delta 7,12-7.23 (m, 4H)3 7.50-7.56 (m, 2H), 7,76 (dd, J = 8.6, 5.4 Hz, IH); LRMS (ES+): m/z 416.0 (100%, [M+H]+); HRMS (ES+) calcd for Ci3H8F2N [M+H]+: 216,0619, found 216.0613; Anal, Calcd for Cj3H7F2N: C, 72.56; H3 3.28; N, 6.51. Found C, 72.4; H, 3.28; N3 6.55.

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; STERIX LIMITED; WOO, Lok Wai Lawrence; BUBERT, Christian; WOOD, Paul Michael; PUTEY, Aurelien; PUROHIT, Atul; POTTER, Barry Victor Lloyd; WO2011/23989; (2011); A1;,
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Related Products of 2698-41-1, 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. 2698-41-1, name is 2-(2-Chlorobenzylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-Arylidenemalononitriles 7 (1 mmol), indane-1,3-dione (2, 0.146 g,1 mmol), NaOAc (0.08 g, 1 mmol), TBBDA (0.14 g, 0.25 mmol) or PBBS(0.2 g) or TCBDA (0.1 g, 0.25 mmol) or PCBS (0.15 g), and EtOH (2 mL)were added to a test-tube. Then the mixture was magnetically stirredat r.t. for the duration as shown in Table 4 and reaction progress wasmonitored by TLC (n-hexane/acetone, 5:2). The mixture was filteredand rinsed with EtOH (2 ¡Á 1 mL). The pure product was isolated byfiltration through a Buechner funnel. Then, the filtrate was evaporated and washed with hot water, CH2Cl2 (3 mL) was added, and the precipitatedsulfonamide was removed by filtration. The sulfonamide wasrehalogenated and used several times. 3-(4-Chlorophenyl)-1?,3?-dioxo-1?,3?-dihydrospiro[cyclopropane-1,2?-indene]-2,2-dicarbonitrile (6a)White solid; yield: 315 mg (95%); mp 199-200 C.IR (KBr): 3075, 3017, 2250, 1746, 1711, 1590, 1499, 1356, 1222, 1093,753, 584 cm-1.1H NMR (400 MHz, DMSO-d6): delta = 4.41 (s, 1 H, CH), 7.61 (d, J = 8.4 Hz,2 H, ArH), 7.66 (d, J = 8.4 Hz, 2 H, ArH), 8.17 (m, 3 H, ArH), 8.26 (d, J =6.4 Hz, 1 H, ArH).13C NMR (100 MHz, DMSO-d6): delta = 20.4, 40.8, 43.8, 110.3, 111.9,123.0, 123.2, 127.3, 128.2, 132.0, 133.4, 136.0, 136.1, 141.5, 142.4,188.9, 190.0.MS: m/z (%) = 332 (M+, 53), 297 (100), 269 (21), 241 (36), 214 (40),187 (14), 165 (37), 138 (19), 104 (100), 76 (97).

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

Reference:
Article; Ghorbani-Vaghei, Ramin; Maghbooli, Yaser; Synthesis; vol. 48; 21; (2016); p. 3803 – 3811;,
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