Month: June 2021

Related Products of 15760-35-7, A common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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 (0730) To a solution of compound 21-1 (5 g, 62 mmol) and RuCl3 (0.25 g, 1.4 mmol) in CH3CN/DCM/H2O (100 mL/100 mL/150 mL) at 0 C. was added NaIO4 (47.3 g, 250 mmol). The mixture was stirred at RT overnight, quenched with water, and extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography (PE: EA=5:1) to give 4.5 g of compound 21-2. 1H NMR (400 MHz, CDCl3): delta 3.53-3.55 (m, 4H), 3.23-3.29 (m, 1H).

The synthetic route of 15760-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Wu, Wen-Lian; Burnett, Duane A.; Stamford, Andrew W.; Cumming, Jared N.; Asberom, Theodros; Bennett, Chad; Sasiskumar, Thavalakulamgara K.; Scott, Jack D.; US9181236; (2015); B2;,
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Reference of 214759-66-7,Some common heterocyclic compound, 214759-66-7, name is Methyl 3-chloro-4-cyanobenzoate, molecular formula is C9H6ClNO2, 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) (0897) A mixture of the compound obtained in Step 3 (500 mg, 2.56 mmol), 4 mol/L aqueous lithium hydroxide solution (10 mL, 40.00 mmol) and THF (10 mL) was stirred at room temperature for 3 hr. The reaction mixture was washed with toluene, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give 3-chloro-4-cyanobenzoic acid as a colorless solid (quantitative). MS (API) :180 (M-H)

The synthetic route of 214759-66-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; SATO, Ayumu; KOUNO, Mitsunori; TOMATA, Yoshihide; OCHIDA, Atsuko; YONEMORI, Kazuko; ODA, Tsuneo; IMADA, Takashi; YUKAWA, Tomoya; (238 pag.)EP2975031; (2016); A1;,
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Electric Literature of 59997-51-2,Some common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, molecular formula is C7H11NO, 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.

At room temperature 4,4-dimethyl-3-oxopentanenitrile (J-Il) (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; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeon-Seop; WO2010/127856; (2010); A1;,
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Some common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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. Application In Synthesis of 2-Amino-5-chlorobenzonitrile

To a mixture of 2- amino-5-chlorobenzonitrile (5.0 g, 32.8 mmol) and hydroxylamine hydrochloride (2.56 g, 36.8 mmol) in water (1 mL) and EtOH (30 mL) was added sodium methoxide (25% wt. soln; 9 mL) and the mixture heated to reflux for 16 hrs. After cooling, 3M NaOH solution was added (75 mL) and the volatiles removed in vacuo. The remaining aqueous phase was washed with DCM, separated and then adjusted to pH~4 by the addition of IN HC1 solution. Filtration and washing of the subsequent precipitate with water gave the N-hydroxybenzimidamide as a colorless solid used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5922-60-1, its application will become more common.

Reference:
Patent; INCEPTION 1, INC.; JACINTHO, Jason, Duarte; CLARK, Ryan, Christopher; SHENG, Tao; OBALLA, Renata, Marcella; STOCK, Nicholas, Simon; ROPPE, Jeffrey, Roger; (161 pag.)WO2017/192304; (2017); A1;,
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Some common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, molecular formula is C7H11NO, 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. name: 4,4-Dimethyl-3-oxopentanenitrile

(4) Synthesis of Intermediate (d)Water (128 mL) was added to 50 g (357 mmol) of Intermediate (c), and the mixture was stirred at room temperature. To this suspension, 98.2 g (785 mmol) of pivaloylacetonitrile was added, and aqueous 12 M hydrochloric acid was added dropwise at the same temperature to adjust the pH to 3. Thereafter, the resulting mixture was heated until the interior temperature became 50 C., and stirred at the same temperature for 6 hours. After the completion of reaction, the reaction solution was neutralized by adding an aqueous 8N potassium hydroxide solution to a pH of 6.4 and then cooled by ice cooling until the internal temperature became 10 C. The precipitated crystal was collected by filtration and spray-washed with water, and the obtained crystal was dried at 60 C. under reduced pressure. To the obtained crude product, 30 mL of toluene was added, and the mixture was dissolved under heating at 60 C. The resulting solution was left standing still at room temperature for 12 hours, and the precipitated crystal was collected by filtration, spray-washed with cooled toluene and dried at 60 C. under reduced pressure to obtain 87.7 g of Intermediate (d) (white powder, yield: 69.3%). The NMR measurement results of Intermediate (d) obtained are as follows. 1H NMR (300 MHz, d-DMSO) 8.74 (s, 1H), 7.99 (s, 1H), 6.87 (s, 4H), 5.35 (s, 2H), 1.24 (s, 18H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59997-51-2, its application will become more common.

Reference:
Patent; FUJIFILM CORPORATION; US2011/17099; (2011); A1;,
Nitrile – Wikipedia,
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Electric Literature of 53312-80-4, 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. 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-amino-2-fluorobenzonitrile(2 g, 14.7 mmol, 1 equiv) and NBS (2.6 g, 14.7 mmol, 1 equiv) in MeCN (100 rnL) was stirred for 4 h at 65 C under nitrogen atmosphere. The resulting mixture was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (13: 1) to afford 4-amino-5-bromo-2- fluorohenzonitrile(3.1 g, 97 2%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS INFLAMMASOME RESEARCH, INC.; FRANCH, Luigi; GHOSH, Shomir; GLICK, Gary; KATZ, Jason; OPIPARI, Anthony William, Jr.; ROUSH, William R.; SEIDEL, Hans Martin; SHEN, Dong-Ming; VENKATRAMAN, Shankar; WINKLER, David Guenther; (479 pag.)WO2020/10143; (2020); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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 1080-74-6, Product Details of 1080-74-6

General procedure: Compound 4 (0.15 g, 0.1275 mmol) and 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (0.371 g, 3.825 mmol) were dissolved inchloroform (15 mL). A drop of pyridine was added and the solution wasleft to stir at 65 C overnight. The reaction was dissolved in ethanol andstirred for another 10 min. The product was extracted with dichloromethaneand dried over MgSO4. After removal of the solvent, thecrude product was chromatographically purified on silica gel column(eluted with chlorobenzene) to afford dark purple .

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

Reference:
Article; Lin, Kaiwen; Xie, Boming; Wang, Zhenfeng; Xie, Ruihao; Huang, Yunping; Duan, Chunhui; Huang, Fei; Cao, Yong; Organic electronics; vol. 52; (2018); p. 42 – 50;,
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Reference of 1483-54-1,Some common heterocyclic compound, 1483-54-1, name is 2-Amino-4-(trifluoromethyl)benzonitrile, 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.

EXAMPLE 4 9-Amino-1,4-methano-1,2,3,4-tetrahydro-6-trifluoromethylacridine To a solution of 2-amino-4-trifluoromethylbenzonitrile (12.8 g) in 50 ml of nitrobenzene was added freshly fused and pulverized ZnCl2 (14.1 g). This was heated at 50 C. fo 1 hour and to this mixture was added norcamphor (11.4 g). The reaction mixture was heated at 130 C. for 3 hours, after which it was cooled, diluted with ethyl ether and filtered. The resulting solid was partitioned between 2-butanone (MEK) and aqueous NH4 OH and the aqueous portion was extracted with MEK. The combined organics were washed with water, dried (satureatd NaCl, MgSO4) and concentrated to a solid which was triturated with ether/hexane to give 10.3 g of a white powder, m.p. 174-179 C. A 4.0 g portion was recrystallized from methanol/water to give 3.5 g of an analytically pure white powder, m.p. 175-178 C.

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-4-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; Hoechst-Roussel Pharmaceuticals Inc.; US5401749; (1995); A;,
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Electric Literature of 179897-89-3, A common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
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Synthetic Route of 1080-74-6, These common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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.

The compound of the formula (III) prepared in the step (1) (100 mg, was added to a 100 mL double-necked flask under argon gas protection.0.116 mmol), the compound of the formula (V) (89.9 mg, 0.464 mmol) and the solvent B (re-evaporated chloroform, 30 mL), after the dissolution was completed, three drops of pyridine (0.15 ml) were added.The mixture was heated to 60 C and stirred under reflux for 3 h, and the reaction solution was cooled to room temperature.The cooled reaction solution was poured into water (100 mL) and extracted with dichloromethane (50ml×2).The organic phase was washed twice with water and dried over anhydrous MgSO4.The filtered filtrate was removed using a rotary evaporator to give a crude material.The crude product was separated and purified by silica gel chromatography column (silica gel effective length 20 cm) using dichloromethane/petroleum ether (1:2 by volume) as an eluent. The Rf value was 0.4-0.5.The effluent, followed by a mixture of dichloromethane and methanol in a volume ratio of 1:10,Dichloromethane and n-hexane are recrystallized one by one in a volume ratio of 1:10 to obtain a compound of formula (VII), DINCNDTS, which is a purple-black solid compound.(77.4 mg, 0.064 mmol, 54.9%).

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Normal University; Zhang Qian; Qiu Huayu; Chen Xianjie; Yin Shouchun; Lin Zhijing; Wang Zhaolong; Xu Xin; (12 pag.)CN109134525; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts