Tag: M.W=0-100

Reference of 107-91-5, 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 107-91-5 as follows.

Add 13.8 g (0.1 mol) to a 250 mL three-necked bottlePotassium carbonate, dissolved in 100 mL of water, added 11.0 g (0.1 mol)Acetylacetone, 8.4 g (0.1 mol) of cyanoacetamide was added in portions at room temperature.During the feeding process, the temperature slowly rises by about 10 C.A large amount of solid precipitated out as the reaction proceeded. After 24 h, the reaction was stopped by TLC (MeOH: DCM = 1: 20) and filtered.The filter cake was washed three times with water.Dry to give 14 g of a white solid.The solid was recrystallized from 1 L of methanol.13.0 g of a white needle-like solid was obtained in a yield of 87.8%.

According to the analysis of related databases, 107-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenyang Pharmaceutical University; Chen Guoliang; Wang Lihui; Zhou Qifan; Du Fangyu; Dong Xiaoyu; Yang Jingyu; Wu Chunfu; (48 pag.)CN109320499; (2019); A;,
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Related Products of 2469-99-0, A common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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.

2-Aminobenzenesulfonic acid (1.73 g,10 mmol)was dissolved in50 mL water, and 0.40 g (10 mmol) of NaOH was added. The solution was cooled in an ice bath to 0 C and 0.69 g (10 mmol) ofNaNO2 was added; 2.00 mL HCl was then added in 0.5 mL portionsfor 1 h. The temperature of the mixture should not exceed 5 C.3-Oxobutanenitrile (0.83 mL, 10 mmol) was added to 30 mLwater-ethanol (5/25, v/v) solution of sodium hydroxide (0.4 g,10 mmol) and sodium acetate (0.82 g, 10 mmol). The resulting solutionwas stirred and cooled to ca. 0 C, and a suspension of thediazonium salt (see above) was added in three portions undervigorous stirring for 1 h. A yellow precipitate of the title compoundwas formed in ca. 1 h, filtered off, dried in air and recrystallizedfrom methanol.NaHL. Yield: 86% (based on 3-oxobutanenitrile), yellow powdersoluble in water, methanol, ethanol, acetone and insoluble inchloroform. Anal. Calcd for C10H8N3NaO4S (Mr 289.24): C, 41.53;H, 2.79; N, 14.53; found: C, 41.46; H, 2.61; N, 14.47%. ESI-MS: m/z:266.02 [Mr-Na]-. IR (KBr): 3459 upsilon(NH), 2206 n(C^N), 1645 n(C]O),1606 and 1534 n(C]N) cm-1. 1H NMRof a mixture of isomeric EandZ-hydrazone forms (300.130 MHz) in DMSO-d6, internal TMS,delta (ppm): E-Hydrazone, 2.43 (s, 3H, CH3), 6.93e7.93 (4H, AreH),12.60 (s, 1H, NeH). Z-Hydrazone, 2.40 (s, 3H, CH3), 6.93e7.93 (4H,AreH), 15.04 (s, 1H, NeH). 13C{1H} NMR (75.468 MHz, DMSO-d6). EHydrazone,delta: 24.65 (CH3), 110.34 (C^N), 115.77 (AreH), 118.00(C]N),124.43 (AreH),127.68 (AreH),130.88 (AreH),134.11 (Are-SO3Na), 136.77 (AreNHN]), 192.51 (C]O). Z-Hydrazone, delta: 28.08(CH3), 112.74 (C^N), 115.39 (AreH), 118.00 (C]N), 125.26 (AreH),127.52 (AreH), 130.62 (AreH), 135.50 (AreSO3Na), 137.62(AreNHN]), 191.42 (C]O).

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gurbanov, Atash V.; Mahmudov, Kamran T.; Kopylovich, Maximilian N.; Guedes da Silva, Fatima M.; Sutradhar, Manas; Guseinov, Firudin I.; Zubkov, Fedor I.; Maharramov, Abel M.; Pombeiro, Armando J.L.; Dyes and Pigments; vol. 138; (2017); p. 107 – 111;,
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These common heterocyclic compound, 630-18-2, name is Pivalonitrile, 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. Application In Synthesis of Pivalonitrile

General procedure: To a solution of anisole 3A (3.0 mmol, 324.4 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol,1.55 M in hexane, 2.87 mL) at 0 C. The mixture was stirred for 2 h at 0 C under an argon atmosphere. Then, pivalonitrile (9.0 mmol, 748.2 mg) in THF (2.0 mL) was added to the mixture at 0 C and the obtained mixture was stirred for 30 min in the temperature range of 0 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 2-methoxybenzonitrile 2A (315.6 mg, 79%).

The synthetic route of Pivalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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Synthetic Route of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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.

(v) 2-Cyano-N-[5-(4-(1,1-dimethylethyl)phenyl)thien-2-yl]-3-hydroxybut-2-enamide A suspension of cyanoacetone, sodium salt (40.98 g); in freshly sodium dried and distilled tetrahydrofuran (200 ml) was mechanically stirred and cooled in an ice-bath. A slightly turbid solution of 2-[4-(1,1-dimethylethyl)phenyl]-5-isocyanatothiophene (100 g), in dry tetrahydrofuran (400 ml) was added dropwise during 40 minutes at 3-5 C. After stirring the mustard coloured suspension in the ice-bath for a further 20 minutes, the bath was then removed, stirring continued for 52 minutes at ambient temperature, then for 1.5 hours at 55 +-2 C. in a heating mantle. After evaporation in vacuo the residual cream coloured paste was stirred in 0.7 N sodium hydroxide (975 ml) for 30 minutes. Filtration removed an insoluble cream coloured solid. The alkaline filtrate was adjusted to pH 1 by the addition of concentrated hydrochloric acid, precipitating a cream coloured pasty solid which was removed by filtration, washed with water (approximately 3 1) and partially dried at 60 C. in vacuo. This solid was stirred at reflux in absolute ethanol (2 1) for 15 minutes, then for 45 minutes in an ice-bath. After filtration, washing with ice-cold ethanol (400 ml) and drying at 60 C. in vacuo. It was further purified by stirring for 10 minutes with charcoal (5 g) in boiling ethyl acetate (2.25 1). The charcoal was removed by filtration and washed on the filter with hot ethyl acetate (300 ml). The filtrate and washings were combined and reduced in volume by 1.5 1 by evaporating in vacuo. After standing in an ice-bath for 1 hour, pale green crystals were removed by filtration, washed with 40-60 C. petrol (100 ml) and dried at 45 C. in vacuo. The crystalline solid was finally purified by stirring in 1N sodium hydroxide (750 ml) and ether (750 ml). The lower aqueous alkaline layer was removed and filtered to clarify. Concentrated hydrochloric acid was added to adjust to pH 1. The resulting cream coloured precipitated solid was filtered off, washed on the filter with water (2 1) and dried at 60 C. in vacuo, m.p. 226-228 C.

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

Reference:
Patent; Lilly Industries Limited; US4983619; (1991); A;,
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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. 33279-01-5, name is 3-Oxopentanenitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Oxopentanenitrile

Step: 1H- thieno[3,2-c] pyrazole-5-carbaldehyde (200mg, 1.314mmol) (see preparation step togetherPreparation Example 1 a) and 3-oxopentanenitrile (191mg, 1.972mmol) wasdissolved in dichloromethane together (20 mL), add The piperidine (11mg,0.131mmol), glacial acetic acid (12mg, 0.197mmol), under nitrogen at refluxovernight trans should. The filtered reaction mixture was cooled to roomtemperature, was added absolute ethanol (20 mL) was diluted reaction mixturewas stirred for ten minutes, filtered It was concentrated to dryness and theresidue was added ethyl acetate (5mL) and petroleum ether (10 mL), stirred forfive minutes and filtered, the solid Dried to give 2 – ((1H- thieno [3,2-c]pyrazol-5-yl) methyl-enyl) -3-oxo-valeronitrile (190mg, 62.5%). ESI-MS: 232 [M+ H].

The synthetic route of 33279-01-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Huilun life Science & Techonology Co.,Ltd; Cheng, Jianjun; Qin, Jihong; Ye, Bin; (68 pag.)CN103467481; (2016); B;,
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Related Products of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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.

After cooling a solution of 3-oxocyclobutanecarbonitrile (32 g, 336 mmol) in methanol (330 mL) to 0 C.,NaBH4 (6.37 g, 168 mmol) was added in small portions. The mixture was stirred at 0 C. for 1 hour.The reaction mixture was quenched with saturated aqueous NaHCO 3 and extracted with ethyl acetate (800 mL).The organic layer was dried over Na2SO4, filtered,Concentrated. This procedure was repeated two more times on the same scale, combined for purification by silica gel chromatography, eluting with 10: 1 to 1: 1 petroleum ether: ethyl acetate to yield the product (30.3 g, 296 mmol, yield). 70%).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
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Electric Literature of 4426-11-3, These common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, 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.

Example 253A 1-(2-methylbenzyl)cyclobutanecarbonitrile n-BuLi (0.018 mol, 7.2 ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at -78 C. After 5 minutes neat cyclobutancarbonitrile (1.2 g, 0.015 mol) was added and the mixture was stirred at -78 C. for 1 hour. Then a solution of 1-(bromomethyl)-2-methylbenzene (3.3 g, 0.018 mol) in THF (3 mL) was added and the mixture was stirred at -78 C. for 1 hour. The mixture was quenched with water and extracted with EtOAc. The organic phase was concentrated and the residue was directly used to the next step without further purification. MS: m/z 186 (M+H)

The synthetic route of 4426-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
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Electric Literature of 98730-77-9, A common heterocyclic compound, 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, molecular formula is C5H7NO, 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.

Intermediate 19: (1-Cyanocyclopropyl)methyl 4-methylbenzenesulphonate (0699) (0700) Et3N (8.97 mL, 64.36 mmol) was added to 1-(hydroxymethyl)cyclopropane-1-carbonitrile (5 g, 51.48 mmol) and TsCl (11.78 g, 61.78 mmol) in DCM (100 mL) cooled to 0 C. under nitrogen. The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was quenched with water (20 mL), extracted with DCM (3¡Á20 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford white solid. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% DCM in petroleum ether. Pure fractions were evaporated to dryness to afford (1-cyanocyclopropyl)methyl 4-methylbenzenesulfonate (5.20 g, 40%). (0701) LC/MS: m/z=252 [M+H]+. 1H NMR (300 MHz, CDCl3) delta 1.09 (dd, J=7.5, 5.7 Hz, 2H), 1.38 (dd, J=7.5, 5.4 Hz, 2H), 2.48 (s, 3H), 4.01 (s, 2H), 7.40 (d, J=8.1 Hz, 2H), 7.84 (d, J=8.1 Hz, 2H).

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; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Related Products of 2469-99-0, These common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, 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 B: 5-Methyl-2-phenyl-2H-pyrazol-3-ylamine Into a 1000-mL 3-necked round bottom flask, was placed a solution of 3-oxobutanenitrile (23 g, 277.11 mmol, 1.00 equiv) in ethanol (400 mL), 1-phenylhydrazine (30 g, 277.78 mmol, 1.00 equiv). The resulting solution was heated to reflux overnight in an oil bath. The resulting mixture was then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to yield 3-methyl-1-phenyl-1H-pyrazol-5-amine as a yellow solid.

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHANG, Xuqing; ABAD, Marta G.; GIBBS, Alan C.; KUO, Gee-Hong; KUO, Lawrence C.; SONG, Fengbin; SUI, Zhihua; US2011/263559; (2011); A1;,
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Application of 33279-01-5, 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. 33279-01-5, name is 3-Oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Preparation of 3-ethyl-l-(3-methylpyridm-2-ylHH-pyrazol-5-amine; EPO 3-Oxo-pentanenitrile (4.87 g, 26.10 mmol) and diphenylmethanone (3-methyl pyridin-2-yl)hydrazone (5.00 g, 17.40 mmol) were dissolved in anhydrous EtOH (150 mL). TsOH (3.31 g, 17.4 mmol) and cone. HCl (14.29 mL, 174.0 mmol) were added to the solution. The mixture was heated at reflux overnight. Additional 3-oxo-pentanenitrile (4.87 g, 26.10 mmol) was added. The mixture was refluxed another 24 h. EtOAc was added. The resulting mixture was basified by slow addition of sat. Na2CO3. The organic layer was dried over MgSO4 and then concentrated. Column chromatography purification (25% EtOAc/ hexane) afforded the title compound as a light yellow oil (1.5 g, 42.6%). 1H NMR (400 MHz, DMSO-d6) delta 8.35-8.34 (IH, d, J = 2.8 Hz), 7.86-7.84 (IH, d, J = 9.6 Hz), 7.39-7.36 (IH, t, J =4.5 Hz), 5.46 (IH, S), 2.58-2.52 (2H, q, J = 6.0 Hz), 2.30 (3H, s), 1.26-1.23 (3H, t, J = 4.2 Hz); LC-MS m/z 203.1 (MH+), HPLC RT (min) 1.07 {method (A)}.

The chemical industry reduces the impact on the environment during synthesis 3-Oxopentanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/27842; (2007); A1;,
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