Tag: M.W=100-200

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. 6136-93-2, name is 2,2-Diethoxyacetonitrile, A new synthetic method of this compound is introduced below., Safety of 2,2-Diethoxyacetonitrile

In a 10-L reactor 2, 2-diethoxyacetonitrile (1.00 kg, 7.74 mol, 1.0 eq. ) was mixed with (NH 4) 2S (48%aqueous solution, 1.41 kg, 9.29 mol, 1.2 eq. ) in methanol (6.0 L) at room temperature. The internal temperature increased to 33 and then dropped back to r.t. After stirring overnight, the reaction mixture was concentrated under vacuum and the residue was taken up in ethyl acetate (5 L) and washed with saturated NaHCO 3 solution (4 × 1.0 L) . The aqueous layer was back-extracted with ethyl acetate (5 × 1.0 L) . The organic phases were combined and washed with brine (3 L) , dried over anhydrous Na 2SO 4and concentrated. The resulting solid was collected by vacuum filtration and washed with petroleum ether. The filtrate was concentrated and triturated with petroleum ether to yield a few crops of white or light yellow solid. All crops were combined to give 1.1 kg of desired product (87%yield) . 1H NMR (500 MHz, CDCl 3) delta 7.81 (d, J = 71.1 Hz, 2H) , 5.03 (s, 1H) , 3.73 (dq, J = 9.4, 7.1 Hz, 2H) , 3.64 (dq, J = 9.4, 7.0 Hz, 2H) , 1.25 (t, J = 7.1 Hz, 6H) .

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; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); 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. 78881-21-7, name is 4-Amino-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Amino-3-methylbenzonitrile

In a round-bottomed flask 4-amino-3-methylbenzonitrile (Alfa Aesar, Avocado, Lancaster; 10.88 g, 82 mmol), and Et3N (22.95 mL, 165 mmol) were stirred in DCM (200 mL) at O0C. TFAA (13.95 ml_, 99 mmol) was added slowly via a dropping funnel and the mixture stirred at room temperature for 30 min. The reaction mixture was poured into 2M HCI (150 ml_). The organic layer was then collected and then washed with a saturated solution of sodium bicarbonate (150 ml_), dried (MgSC^), filtered and the solvent was removed to give a dark yellow solid (19.37 g); m/z (ES”) 227 (M-1 );1 H NMR (400MHz, CDCI3): delta 8.43 (1 H, d), 7.91 (1 H, br s), 7.59 (1 H, dd). 7.56 (1 H, s). 2.37 (3H, s).

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; GLAXO GROUP LIMITED; WO2009/127678; (2009); A1;,
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Reference of 16532-79-9, The chemical industry reduces the impact on the environment during synthesis 16532-79-9, name is 4-Bromophenylacetonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Sodium methoxide (4 mmol) – methanol solution was slowly added to a solution of 4 (1.0 g, 2.12 mmol) and I2 (0.51 g, 2.01 mmol) in dry diethyl ether at -78C. The reaction mixture was stirred for 12 h at rt. The crude product was filtered and washed with water and methanol. The residue was purified by silica gel column chromatography. The pure 1 was obtained by size-exculsion chromatography (JAIGEL-2H and 1H, CHCl3). Title compound was obtained as an orange solid (200 mg, 20%).

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

Reference:
Article; Furuyama, Taniyuki; Shinozaki, Junichi; Tasso, Thiago Teixeira; Maeda, Hajime; Segi, Masahito; Kobayashi, Nagao; Tetrahedron Letters; vol. 58; 45; (2017); p. 4243 – 4247;,
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Reference of 72291-30-6, A common heterocyclic compound, 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, molecular formula is C6H9NO2, 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 experiment examples are carried out in a 1 l reactor (10×2000 mm), equipped with feed pumps for solvent, ammonia and nitrile ester, charged with 250 ml of steel rings in the lower and upper reactor section, and centrally with 500 ml of tablets (5×3 mm) of a hydrogenation catalyst of the following composition: 28% NiO, 28% CoO, 13% CuO and 31% ZrO2, in liquid phase mode. The reduction procedure of the catalyst is as follows: the reactor is heated to 180 C. at a hydrogen feed of 50 l/h within 5 hours, then kept at 180 C. with 50 l/h of hydrogen for 20 hours, cooled under hydrogen and purged with MeOH, before ammonia and reactant and also solvent are fed in. The steel rings in the lower part of the reactor serve as the delay time zone for the amidation. 11 equivalents of hydrogen are fed in per nitrile used. The delay time is thus approx. 10 minutes. Example 10250 g/h of tetrahydrofuran (THF) and methyl 2-cyano-2,2-dimethylacetate as the nitrile ester (in a weight ratio of 70:30) and 205 g of ammonia (20 equivalents of ammonia based on nitrite ester) are conducted through the reactor at 200 bar and 100 C. The volume space velocity is 0.15 kg/l*h. The effluent analysis shows (calculated without solvent) 33.083% aminopivalinamide, 65.68% methyl aminopivalate and 0.49% others. The delay time is approx. 27 minutes.

The synthetic route of 72291-30-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2008/306299; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 58331-97-8, name is Methyl 4-chloro-2-cyanobenzoate, 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 58331-97-8, Recommanded Product: Methyl 4-chloro-2-cyanobenzoate

To a solution of methyl 4-chloro-2-cyanobenzoate (2.0 g, 10.2 mmol) in Et2O (40 mL) was added Ti(OiPr)4 (3.43 ml, 11.7 mmol). After cooling to 0 C., a 3.0 M solution of EtMgBr in Et2O (6.8 ml, 20.4 mmol) was added slowly. The reaction was warmed to room temperature and stirred for 3 h. Upon completion, the reaction was quenched with 1.0 M HCl (20 mL) then filtered over celite. The layers were separated and the aqueous layer was washed with EtOAc (2×20 mL). The combined organics were dried over Na2SO4, then filtered and concentrated. The crude product was purified by flash chromatography over silica gel (2-5% MeOH/DCM eluent) to provide 6′-chlorospiro[cyclopropane-1,1′-isoindolin]-3′-one (400 mg, 21% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.75 (br. s., 1H), 7.66 (d, J=8.5 Hz, 1H), 7.40-7.54 (m, 2H), 1.47 (dt, J=11.2, 2.8 Hz, 4H); MS m/z C10H8ClNO [M+1]+=194.6.

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; Augeri, David John; Bagdanoff, Jeffrey Thomas; Baugh, Simon David Peter; Carlsen, Marianne; Carson, Kenneth Gordon; Gilleran, John Anthony; He, Wei; Oravecz, Tamas; Salojin, Konstantin; Sung, Leonard; US2012/225857; (2012); A1;,
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These common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, 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. Recommanded Product: 4,5-Dichlorophthalonitrile

0.30 g(1.5 mmol) of 4,5-dichlorophthalonitrile and 0.28 g(3.0 mmol) of phenol preliminarily crystallized fromhexane were dissolved in 15 mL of DMF and asolution of 0.42 g (3 mmol) of potassium carbonate in1 mL water was added. The reaction mixture wasstirred at 80-90 for 12 h, then the target product wasfiltered off, washed with hot water till the smell ofphenol ceased, and dried at 80-90. Yield 0.26 g(82%). Found, %: C 76.38; H 3.98; N 8.72. C20H12N22.Calculated, %: C 76.91; H 3.87; N 8.97.

The synthetic route of 4,5-Dichlorophthalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Znoiko; Petlina; Shaposhnikov; Smirnov; Russian Journal of General Chemistry; vol. 88; 6; (2018); p. 1148 – 1153; Zh. Obshch. Khim.; vol. 88; 6; (2018); p. 968 – 973,6;,
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Reference of 42872-83-3, A common heterocyclic compound, 42872-83-3, name is 2-Bromo-5-methylbenzonitrile, molecular formula is C8H6BrN, 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.

To a solution of (3-(ethoxycarbonyl)phenyl)boronic acid (386 mg, 1.99 mmol, Eq: 1.3) in THF (5 mL) was added 2-bromo-5-methylbenzonitrile (300 mg, 1.53 mmol, Eq: 1) and potassium fluoride (267 mg, 4.59 mmol, Eq: 3). The reaction mixture was degassed under a slight argon flush in an ultrasonic bath for 15 minutes. palladium(II) acetate (6.87 mg, 30.6 muiotaetaomicron, Eq: 0.02) and (2-biphenyl)di-tert-butylphosphine (18.3 mg, 61.2 muiotaetaomicron, Eq: 0.04) was added. The reaction mixture was stirred for 18 hours at 50C. The reaction mixture was poured on 30 mL water and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography to yield ethyl 3-(2-cyano-4-methylphenyl)benzoate as a white solid (383 mg, 94.3%). MS (ESI): m/z = 266.118 [M+H]+.

The synthetic route of 42872-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BLEICHER, Konrad; HERT, Jerome; KROLL, Carsten; DEY, Fabian; (77 pag.)WO2018/189063; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13531-48-1, name is Methyl 3-cyanobenzoate, 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 13531-48-1, Quality Control of Methyl 3-cyanobenzoate

A solution of 2 g (0.01 mol) of methyl-3-cyanobenzoate in 32 ml of THF and 8 ml of water was charged with 2.3 g (0.012 mol) of diethyl dithiophosphate and heated at 80 C. for 24 h. THF was removed and the residue was taken in ethyl acetate. The extract was washed with water and concentrated to afford methyl 3-carbamothioylbenzoate (2.0 g) as a pale yellow solid.

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Reference:
Patent; Carter, Percy H.; Cherney, Robert J.; Batt, Douglas G.; Duncia, John V.; Gardner, Daniel S.; Ko, Soo S.; Srivastava, Anurag S.; Yang, Michael G.; US2005/54627; (2005); A1;,
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Application 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.

4,4-Dimethyl-3-oxopentanenitrile (80 mmol, 10 g)At room temperature EtOH (200 mL)And stirred at 0 C, hydrazine monohydrate(160 mmol, 7.74 ml) was slowly added. Heated to 90 C and refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. Diluted with water, extracted with EtOAc Respectively. Sodium sulfate was added to the extracted organic solvent to remove residual water, and the resultant was separated by MPLC to obtain a red solid Was prepared in a yield of 57%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,4-Dimethyl-3-oxopentanenitrile, its application will become more common.

Reference:
Patent; Korea Research Institute of Chemical Technology; Lee, Kwang Ho; Choe, Gil Don; Park, Sang Jun; Lee, Na Li; Jung, Myung Eun; Kim, Sung Jin; Yang, Kyung Min; Lee, Ji Hee; (28 pag.)KR101726648; (2017); B1;,
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Related Products of 42872-83-3,Some common heterocyclic compound, 42872-83-3, name is 2-Bromo-5-methylbenzonitrile, molecular formula is C8H6BrN, 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.

MethyI-2-(pyrimidin-2-yl)benzonitrile (2); To a 500 mL three neck round bottom flask, equipped with an overhead stirrer, thermocouple and nitrogen inlet and dropped funnel, was charged 2-bromo-5-methylbenzylnitrile1 (20.00 g) and THF (60 mL, 3 V) and was cooled to -15 C. 1.3 M of i-PrMgCI’LiCl (1 10.0 mL, 1.4 equiv) was slowly added at -15 to -12 C. The reaction mixture was stirred at -15 to -12 C for 3.5 h (> 99 A% conversion). 15.45 g of anhydrous ZnCl2 (1.1 equiv, powder) was added to the Grignard reagent at -12 C in one portion. The reaction was exothermic raising the temperature of the reaction mixture to 0 C. The reaction mixture was stirred at -3 to 2 C for 0.5 h and slowly warmed to rt over 0.5 h. The reaction mixture became a homogenous solution and then 2-chloropyrimidine (15.37 g) was added.To a slurry of 1 mol% Pd(OAc)2 (0.229 g), 4 mol% («-Bu)3P (0.826 g or 1.02 mL) in THF (8 mL) was added 2.0 M of BuMgCl (1.02 mL) THF solution to become yellow cloudy solution, The resulting catalyst solution was added to the reaction mixture. The resulting mixture was heated at 55 C for 17 h: (98 A% conversion). The reaction mixture was solvent-switched to isopropyl alcohol (140 mL, total volume) at 40-45 C. Then 5 wt% NH4C1 aqueous solution (70 mL) was added dropwise at 15 to 20 C. The resulting slurry was aged at 10 C for 5 h. The crystalline solid was collected by filtration, rinsed with cold isopropyl alcohol/water (1 : 1, 35 mL), and ^-heptane (30 mL), dried under vacuum with nitrogen sweep and gave desired product2 (17.33 g, 87% isolated yield, 99.5 LCAP purity).HPLC MethodColumn: Zorbax Eclipse Plus CI 8 50 x 4.6 mm, 1.8 muetaiota particle size, Column Temp.: 25 C; Flow Rate: 1.5 mL/min; Detection: 230 nm; Mobile Phase: A: Water 0.1% H3PO4, B: AcetonitrileMobile Phase Program: Time A0 90%5 min 5%6 min 5%6.1 min 90%8 min 90%Compound 2: 3.19 min

The synthetic route of 42872-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; FENG, Yun Shao; MOSES, Anthony; ZHONG, Yong-Li; WO2012/58129; (2012); A1;,
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