Tag: M.W=100-200

Reference of 2941-29-9, These common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, 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 2-cyanocyclopentanone (20.0 g, 183 mmol, prepared as described in Fleming et al, J. Org. Chem. 2007, 72, 1431-1436 in the Supporting Information), water (24.7 ml), and sodium cyanide (14.8 g, 302 mmol) was cooled with an ice bath to a temperature of 5 °C to 10 °C. A mixture of sulfuric acid (29.3 ml, 550 mmol) and water (24.7 ml), said mixture having a temperature of 10 °C, was added drop wise within 0.5 h while stirring. The ice bath was then removed, and the mixture was stirred for 2.5 h at room temperature. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (3 x 100 ml). The combined extracts were dried with magnesium sulfate, and pyridine (51 ml, 631 mmol) was added. The solution was cooled with an ice bath to a temperature of 5 °C to 10 °C, and acetyl chloride (40.0 ml, 561 mmol) was added drop wise. The resulting mixture was stirred at 0 °C for 2 h, and then at room temperature overnight. After filtration and concentration under reduced pressure, toluene (100 ml) and ethyldiisopropylamine (94 ml, 553 mmol) were added to the residue, and the mixture was stirred at 100 °C for 6 h, and at room temperature overnight. The mixture was poured into a mixture of aqueous, concentrated hydrochloric acid (68 ml) and water (70 ml), phases were separated, the aqueous phase was extracted with ethyl acetate (3 x 150 ml), the combined extracts were washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure to yield 22.5 g of a dark oil. Distillation (2 mbar) yielded 8.6 g (40percent) of compound of formula (II) (bp 66-71 °C). 1H NMR (CDCls, 400 MHz) compound of formula (II): delta 2.17 (quint, J = 7 Hz, 2H), 2.83 (t, J = 7 Hz, 4H).

The synthetic route of 2941-29-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONZA LTD; ZARAGOZA DOERWALD, Florencio; WO2013/102634; (2013); A1;,
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Reference of 3288-99-1, These common heterocyclic compound, 3288-99-1, name is 2-(4-(tert-Butyl)phenyl)acetonitrile, 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 10 L-reaction flask equipped with a rectification column and a separating tank, 314 g (1.81 mol) of 4-tert-butylphenylacetonitrile, 300 g (1.65 mol) of 1,3,4-trimethylpyrazol-5-carboxylic acid ethyl ester, 3000 g of heptane, 225 g of diethylene glycol dimethyl ether, and 99 g of diethylene glycol monoethyl ether were added, the atmosphere was substituted with nitrogen, then azeotropic dehydration was carried out by heating at 90 to 95 C. for 1 hour. The temperature was maintained, 381 g (1.98 mol) of 28% sodium methoxide methanol solution was added dropwise over 10 hours, and the resulting mixture was further reacted for 7 hours. After cooling to 30 C. or less, 3000 g of water was added to separate out heptane phase, and the resulting aqueous phase was further washed with 600 g of heptane to separate out heptane phase. A quantitative analysis of the obtained aqueous phase with liquid chromatography showed that the aqueous phase contained 466 g (yield 91.5%) of 2-(4-tert-butylphenyl)-3-(1,3,4-trimethyl-5-pyrazolyl)-3-oxopropionitrile. After adding 2760 g of xylene to the aqueous phase, 206 g (1.98 mol) of 35% hydrochloric acid was added dropwise to be neutralized. After separating out the aqueous phase, the resulting organic phase was washed two times with 600 g of water and the aqueous phase was separated out to obtain xylene solution of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile. A quantitative analysis with liquid chromatography showed that the xylene solution contained 456 g (yield 89.6%) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile.

The synthetic route of 3288-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Kenzo; Kondo, Yasuo; Tanaka, Norio; Suzuki, Hideaki; Ohnari, Masatoshi; Nishio, Koichi; US2006/178523; (2006); A1;,
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Application of 77326-36-4, 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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

It was prepared as described for 8. Starting from 2-amino-6-fluorobenzonitrile (318 mg, 2.31 mmol) in 1,2-dichloroethane (25 mL) and enone 7 (R9 = i-Pr) (272 mg, 1.53 mmol) in 1,2-dichloroethane (15 mL), a crude product (383 mg) was obtained and subjected to column chromatography [silica gel (19 g), hexane/AcOEt/25% aqueous NH4OH mixtures as eluent]. On elution with hexane/AcOEt/25% aqueous NH4OH 98:2:0.1, huprine 10 (220 mg, 42% yield) was obtained as a beige solid.A solution of huprine 10 (220 mg, 0.74 mmol) in CH2Cl2 (15 mL) was filtered through a PTFE 0.45 mum filter, treated with 1.81 N methanolic solution of HCl (1.24 mL, 2.24 mmol), and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 30:1 (9.3 mL), 10·HCl (138 mg) was obtained as a beige solid, mp >300 C (dec.) (AcOEt/MeOH 30:1). IR (KBr) nu 3500-2500 (max at 3494, 3370, 3312, 3201, 3158, 3024, 2958, 2929, 2891, 2833, 2750, 2669, C-H, N-H, and N+-H st), 1640, 1595, and 1548 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 0.87 (d, J = 7.0 Hz, 3H) and 0.89 (d, J = 7.0 Hz, 3 H) [9-CH(CH3)2], 1.97 (dm, J = 12.5 Hz, 1H, 13-Hsyn), 2.02-2.12 [complex signal, 2H, 13-Hanti and 9-CH(CH3)2], superimposed in part 2.08 (br d, J = 17.5 Hz, 1H, 10-Hendo), 2.52 (br dd, J = 17.5 Hz, J’ = 5.0 Hz, 1H, 10-Hexo), 2.80 (m, 1H, 7-H), 2.86 (dm, J ? 18.0 Hz, 1H, 6-Hendo), 3.21 (dd, J = 18.0 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.41 (m, 1H, 11-H), 4.85 (s, NH2 and NH+), 5.58 (dm, J = 5.0 Hz, 1H, 8-H), 7.34 (ddd, J = 13.5 Hz, J’ = 8.0 Hz, J = 1.0 Hz, 1H, 2-H), 7.56 (br d, J = 8.5 Hz, 1H, 4-H), 7.82 (dddm, J ? J’ ? 8.5 Hz, J = 5.5 Hz, 1H, 3-H); 13C NMR (75.4 MHz, CD3OD) delta 21.4 (CH3) and 21.9 (CH3) [9-CH(CH3)2], 27.2 (CH, C11), 27.9 (CH, C7), 29.6 (CH2, C13), 31.7 (CH2, C10), 35.9 [CH, 9-CH(CH3)2], 36.1 (CH2, C6), 107.2 (C, d, J ? 11.5 Hz, C12a), 112.2 (CH, d, J = 23.3 Hz, C2), 115.7 (C, C11a), 116.3 (CH, C4), 122.2 (CH, C8), 134.9 (CH, d, J ? 11.5 Hz, C3), 140.6 (C, C4a), 144.5 (C, C9), 152.9 (C) and 155.3 (C) (C5a and C12), 161.1 (C, d, J = 253 Hz, C1). Anal. Calcd for C19H21FN2·HCl·3/4H2O (346.36): C, 65.89; H, 6.84; N, 8.09; Cl, 10.24. Found: C, 65.55; H, 6.62; N, 7.99; Cl, 10.21.

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
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Application of 21667-62-9, 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. 21667-62-9 name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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: A mixture of ethyl 3-oxo-3-phenylpropanoate (2a) (1.73 mL,10.00 mmol) and allylamine [(3.75 mL, 50.00 mmol) neutralized with acetic acid (2.86 mL, 50.00 mmol)] in ethanol (10 mL) was heated to reflux for 3 h. The resulting mixture was concentrated and the residue was taken up in CH2Cl2. The organic layer was washed with 5% HCl and water, dried over MgSO4 and concentrated. Purification of the crude product by flash column chromatography (silica gel; petroleum ether/ethyl acetate95:5) afforded 3a (2.08 g, 9.00 mmol) in 90% yield as a colourless liquid. When treated with 2c, it afforded 3c instead of 3-(allylamino)-3-(2-fluorophenyl) acrylonitrile.

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

Reference:
Article; Zhai, Sheng-Xian; Dong, Hong-Ru; Chen, Zi-Bao; Hu, Yi-Ming; Dong, Heng-Shan; Tetrahedron; vol. 70; 44; (2014); p. 8405 – 8412;,
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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 1009-35-4 as follows. SDS of cas: 1009-35-4

4-Fluoro-3-nitrobenzonitrile (182.6 g; 1.10 moles) was dissolved in DMF at 25- 30°C under nitrogen atmosphere and sodium carbonate (249.8 g; 2.36 moles) was added. The slurry was heated to 45-50°C and compound obtained in example- 05/DMF solution (327.12 g; 0.78 moles) was added in 30-60 min at 45-50°C. The reaction mass was maintained for ~8h at 45-50°C. After completion of the reaction by HPLC, reaction mass was diluted with ethyl acetate and water at < 50°C and stirred for 30-45 min. Layers were separated and aqueous layer was extracted with ethyl acetate. Combined organic layer was washed with -10percent w/v brine solution and concentrated under vacuum at < 55°C. Methanol was added to the concentrated residue and heated to 45-50°C and stirred for lh at 45-50°C. The obtained slurry was cooled to 25-30°C and maintained for lh at 25-30°C. The product was filtered and washed with methanol followed by water and then dried under vacuum to obtain the title product as a light yellow wet solid (369.2 g; 74.85percent of theory on dried basis). HPLC Purity: 95.91percent. According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular. Reference:
Patent; NATCO PHARMA LIMITED; APPAYE KALIYAPERUMAL, Srinivasan; TALASANI, Shyam Sunder Reddy; SAMATHAM, Nagalingam; KONDURI, Srinivasa Krishna Murthy; BUDIDETI, Shankar Reddy; MUDDASANI, Pulla Reddy; NANNAPANENI, Venkaiah Chowdary; (22 pag.)WO2019/38779; (2019); A1;,
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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 134450-56-9 as follows. Application In Synthesis of 4,5-Difluorophthalonitrile

Compounds 5 and 6 were synthesized by reacting 4 with sub-stoichiometric or stoichiometric 4,5-difluorophthalonitrile, respectively, under basic conditions via nucleophilic aromatic substitution reaction. The targeted charged TADF emitters XI and XII were obtained following methylation with iodomethane and anion metathesis with saturated NH4PF6 solution in 33% and 27% yield, respectively, over six steps. The solubilities of XI and XII in DCM were greatly improved after the anion metathesis, in comparison with that of the original iodo salts.

According to the analysis of related databases, 134450-56-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; Zysman-Colman, Eli; Wong, Michael Yin; (41 pag.)US2017/352818; (2017); A1;,
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Related Products of 6393-40-4, These common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, 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.

Reference B; Synthesis of 3,4-diaminobenzamidine monohydrochloride; Step 1; A mixture of 4-amino-3-nitrobenzonitrile (63.3 g, 388 mmol) in 1,4-dioxane (600 mL) and anhydrous ethanol (600 mL) was cooled in an ice water bath to 0-5 C and treated with gaseous HCl for 1.5 h. The reaction mixture was tightly sealed and allowed to warm up to room temperature with stirring for 18 h. The flask was then carefully unsealed and the reaction mixture was diluted with anhydrous diethyl ether (about 2.4 L) until a cloudy solution was obtained. A minimum amount of absolute ethanol required to give a clear solution was then added, and the resulting solution stirred until crystals of 4-amino-3-nitro-benzimidic acid ethyl ester were observed. Ether was then cautiously added to complete the crystallization process and the suspension was allowed to stand for about 30 minutes. The crystals were filtered and washed with dry diethyl ether, then allowed to dry under aspirator vacuum. The crystals were dried in vacuo to give 4-amino-3-nitro-benzimidic acid ethyl ester hydrochloride (84.6 g) as off-white crystals.

The synthetic route of 6393-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2005/118554; (2005); A2;,
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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. 6575-13-9, name is 2,6-Dimethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H9N

General procedure: An oven-dried, three-necked flask was sealed with septa and evacuated/backfilled with N2 three times before starting the reaction. To a mixture of 2.5M n-BuLi in hexane (35 mL, 87.6 mmol) anddry THF (20 mL), maintained at below -70 C, solution of N,N-diethyl-2,4-dimethylbenzamide (10a; 6 g, 29.2 mmol) and 3,4-dimethoxybenzonitrile (11b; 7.15 g, 43.8 mmol) in dry THF (7 mL)were added maintaining the temperature below -60 C. The reaction mixture was stirred at -78 C for 38.5 h. The reaction mixture was then warmed to room temperature and quenched with water. The precipitate was filtered off and washed with water and EtOAc to obtain 9b as an off-white solid. The filtrate was extracted with CH2Cl2, washed with water, and concentrated under reduced pressure. The EtOAc-insoluble fraction was again filtered off and washed with EtOAc to obtain 9b (6.46 g, 74%).

According to the analysis of related databases, 6575-13-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khadka, Daulat Bikram; Woo, Hyunjung; Yang, Su Hui; Zhao, Chao; Jin, Yifeng; Le, Thanh Nguyen; Kwon, Youngjoo; Cho, Won-Jea; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 583 – 607;,
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134450-56-9, name is 4,5-Difluorophthalonitrile, 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: 134450-56-9

1.52 g (9.14 mmol) 9H-carbazole and 1.91 g (13.7 mol)of potassium carbonate were placed in a 50-mE recovery flask, and the interior of the flask was substituted with nitrogen. 15 mE of dimethylsulfoxide was added to themixture, which was stirred under a nitrogen stream at room temperature for 1 hout 0.500 g (3.05 mmol) of 4,5-difluo- rophthalonitrile was added to the mixture. The mixture was stirred under a nitrogen stream at room temperature for 3 hours and then at 500 C. for 20 hours. Thereafier, the mixturewas added to water, followed by stirring. The mixture was extracted with toluene. After the extraction, the extracted solution was rinsed with a saturated sodium chlorine aqueous solution. After rinsing, an organic layer and an aqueous layer were separated, and the organic layer was dried byadding magnesium sulfate thereto. After drying, the mixture was suction-filtered to provide a filtrate. The resulting filtrate was concentrated to provide a solid matter, which was purified by silica gel column chromatography. In the purification, a mixed solvent of toluene and hexane (1/4) was firstly used as a developing solvent, then a mixed solvent of toluene and hexane (7/3) was used, and then toluene was used as a developing solvent (the developing ratio was gradually changed). The resulting fraction was concentratedto provide a solid matter, which was then rinsed by reslurrywith a mixed solvent of acetone and methanol, therebyproviding a pale yellow powdered solid matter in a yieldamount of 1.20 g and a yield of 85.8%.

The synthetic route of 134450-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYULUX, INC.; Adachi, Chihaya; Uoyama, Hiroki; Nomura, Hiroko; Goushi, Kenichi; Yasuda, Takuma; Kondo, Ryosuke; Shizu, Katsuyuki; Nakanotani, Hajime; Nishide, Jyunichi; (83 pag.)US9502668; (2016); B2;,
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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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Cyanobenzyl alcohol

Add p-toluene sulphonic acid (2.11 g, 12.2 mmol) to a solution of 3- hydroxymethyl-benzonitrile( 16.30 g, 122.4 mmol) and 3,4-dihydro-2H-pyran (51.5 g, 612 mmol) in dicliloromethane (500 ml) and stir. After 90 minutes, pour reaction into saturated sodium bicarbonate, remove organics, dry with sodium sulfate, filter and concentrate to give a dark brown oil. Purify the residue by flash chromatography eluting with a gradient of 10-15% ethyl acetate :hexanes to yield the title product as a clear oil (16.20 g, 61%): 1H NMR (CDCl3) delta 1.53-1.91 (m, 6H), 3.56 (m, IH)5 3.88 (m, IH), 4.53 (d, IH), 4.72 (t, IH), 4.81 (d, IH), 7.45 (t, IH), 7.58 (m, 2H), 7.69 (s, IH)

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; ELI LILLY AND COMPANY; WO2006/57860; (2006); A1;,
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