Month: August 2021

Reference of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

[0949] 1.00 g (4.90 mmol) of 2-bromo-4-fluorobenzonitrile, 335 mg (4.96 mmol, 1.012 eq.) of methylamine hydrochloride and 1.71 ml (9.80 mmol, 2 eq.) of N,N-diisopropylethylamine were initially charged in 9.85 ml of 1-methyl-2-pyrrolidone and the mixture was heated in the microwave at 120 C. for 40 min. The cooled reaction mixture was partitioned between ethyl acetate and water, and the aqueous phase was extracted once more with ethyl acetate. The combined organic phases were washed three times with water, then with saturated aqueous sodium chloride solution, dried and concentrated. The crude product was purified by means of normal phase flash chromatography (eluent: cyclohexane/ethyl acetate, 0-40%). Yield: 660 mg (63% of theory). LC/MS [Method 1]: Rt=0.82 min; MS (ESIpos): m/z=211 (M+H)+, 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=7.50 (d, 1H), 7.06-6.94 (m, 1H), 6.84 (d, 1H), 6.60 (dd, 1H), 2.73 (d, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-fluorobenzonitrile, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ-NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; ACKERSTAFF, Jens; STAMPFUss, Jan; (87 pag.)US2017/291892; (2017); A1;,
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Related Products of 1835-65-0, 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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 1.0 M solution of LiN(SiMe3)2 (2.2 mL, 2.2 mmol) in THF was added at -90 C in an argon atmosphere to a vigorously stirred solution of 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (314 mg, 2.0 mmol) in absolute THF (30 mL). The reaction mixture was stirred at -90 C for 30 min. Then, a solution of tetrafluorophthalonitrile (400 mg, 2.0 mmol) in THF (5 mL) was added at -90 C under argon, stirring was continued, and the reaction was monitored by TLC (Silufol F254, EtOAc as an eluent). After 2 or 6 h, the cooling was stopped, the reaction mixture was allowed to warm up to room temperature and was brought into contact with air. Flash chromatography (SiO2, column 3 * 4 cm, EtOAc as an eluent) yielded dark brown solid mixture after solvent removal under reduced pressure at room temperature. The obtained solid mixture was separated by column chromatography (SiO2, column 3 * 20 cm, CH2Cl2 as an eluent), which afforded a dark green fraction of radical 1 and dark green fraction of radical 2. Both fractions were concentrated under reduced pressure to a volume of ~5 mL. Next, n-heptane (5 mL) was added, and the mixtures were kept at a temperature of 0-5 C for slow crystallization of radicals 1 and 2. 4.3. 2-(3,4-Dicyano-2,5,6-trifluorophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (1) Yield 101 mg (15%); dark green crystals; mp 166.9 – 167.2 C (uncorrected). IR (KBr) max/cm-1: 430, 447, 474, 501, 542, 611, 629, 667, 694, 746, 781, 870, 899, 941, 955, 982, 1065, 1070, 1138, 1173, 1223, 1277, 1379, 1431, 1458, 1481, 1527, 1504, 1585, 1624, 1732, 2243 (C?N), 2569, 2631, 2854, 2928, 2947 3005, 3425; UV-vis (C2H5OH) lambdamax/nm (lg epsilon): 560 (2.37), 402 (3.32), 306 (4.21), 230 (4.19), 203 (4.45); UV-vis (KBr) lambdamax/nm: 425, 331, 307, 245, 233, 212; Anal. calcd for C15H12F3N4O2: C 53.42, H 3.59, F 16.90, N 16.61; found: C 53.50, H 3.25, F 16.97, N 16.74; HRMS: calcd. for C15H14F3N4O2 [M+] 337.0907; found 337.0912.

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, 3,4,5,6-Tetrafluorophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fedyushin, Pavel; Panteleeva, Elena; Bagryanskaya, Irina; Maryunina, Kseniya; Inoue, Katsuya; Stass, Dmitri; Tretyakov, Evgeny; Journal of Fluorine Chemistry; vol. 217; (2019); p. 1 – 7;,
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151-18-8, name is 3-Aminopropanenitrile, 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. Product Details of 151-18-8

To a 3-neck round-bottom flask wasadded (S)-3-[5-(3,4-dichloro-phenyl)-1 -(4-methoxy-phenyl)-1 H-pyrazol-3-yl]-2-25 m-tolyl-propionic acid (Example 1; 5.0 g, 9.9 mmol, 1.0 equiv), EDC (4.7 g, 24.7 mmol, 2.5 equiv) and HOST (3.3 g, 24.7 mmol, 2.5 equiv) under nitrogen.A/,A/-Dimethylformamide (50 ml) was added, followed by 3-aminopropanenitrile(1.9 g, 24.7 mmol, 2.5 equiv) and diisopropylethylamine (6.8 ml, 39.6 mmol,4.0 equiv). The reaction mixture was stirred overnight, then was diluted with5 ethyl acetate (200 ml), washed with 1 N HCI (100 ml), H2O (100 mL),10%sodium bicarbonate (100 ml), H2O (100 ml) then brine (100 ml), and dried(sodium sulfate). The solvent was then removed under reduced pressureyielding the desired amide (5.35 g, 99%), which was used in the next stepwithout purification. HPLC: Rt = 7.89 (Method A). MS (ESI): mass calculated10 for C29H26Cl2N4O2, 532.14; m/zfound, 533.3 [M+H]+. 1H NMR (500 MHz,CDCI3): 7.31-7.30 (m, 2H), 7.23 (t, J= 7.4 Hz, 1H), 7.19 (br s, 1H), 7.16-7.14(m, 3H), 7.10 (d, J= 7.4 Hz, 1H), 6.91 (dd, J = 8.5, 2.2 Hz, 1H), 6.87 (d, J= 9.0Hz, 2H), 6.20 (s, 1H), 6.09 (t, J = 6.0 Hz, 1H), 3.90 (dd, J = 9.0, 6.0 Hz, 1H),3.82 (s, 3H), 3.56-3.50 (m, 2H), 3.35-3.31 (m, 1H), 3.08 (dd, J = 14.8, 6.0 Hz,15 1 H), 2.53-2.46 (m, 2H), 2.35 (s, 3H).

The synthetic route of 151-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/5393; (2005); A2;,
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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. 2469-99-0, name is 3-Oxobutanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Oxobutanenitrile

Step 1. 2-Benzylidene-3-oxobutanenitrile Into a 100-mL round-bottom flask, was placed a solution of 3-oxobutanenitrile (4.15 g, 50.00 mmol, 1.00 equiv) in toluene (50 mL), benzaldehyde (5.3 g, 50.00 mmol, 1.00 equiv), piperidine (430 mg, 5.06 mmol, 0.10 equiv), and acetic acid (600 mg, 10.00 mmol, 0.20 equiv). The resulting solution was heated to reflux for 8 hr. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 2.3 g (24%) of 2-benzylidene-3-oxobutanenitrile as a yellow solid.

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; BIOENERGENIX; US2012/277224; (2012); A1;,
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Synthetic Route of 328-87-0, 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. 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

162 grams of 92% sodium ethanolate were dissolved in 750 milliliters of dimethylformamide and 260 grams of 3-fluorophenol, 530 grams of 2-chloro-5-trifluoromethylbenzonitrile, 25 grams of Adams Copper catalyst and 25 grams of cuprus iodide were added. The mixture was heated to 150 C without reflux condenser, whereupon a reflux condenser was placed in a neck of the flask and heating was continued for 3 hours at 160C. Dimethylformamide was distilled off in vacuum. The residue was suspended in water and extracted with chloroform, the chloroform-layer separated, washed with water, filtered and evaporated. The residue was dissolved in 1500 milliliters of 96% ethanol and 500 milliliters of water, whereupon 530 grams of potassium hydroxide were added in small portions and the mixture refluxed for 18 hours. 700 milliliters of concentrated hydrochloric acid were added dropwise and ethanol evaporated, whereupon the mixture was cooled and extracted with 2000 milliliters of ether. The ether phase was separated, washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuum. The residue consisted of 2-(3-fluorophenyloxy)-5-trifluoromethyl-benzoic acid as an oil. Yield: 700 grams.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5-trifluoromethylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kefalas A/S; US3951961; (1976); A;,
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Adding a certain compound to certain chemical reactions, such as: 555-21-5, name is 4-Nitrophenylacetonitrile, 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 555-21-5, HPLC of Formula: C8H6N2O2

Step 1: 2-Methyl-2-(4-nitrophenyl)propanenitrile 4-Nitrophenyl acetonitrile (20 g, 123.45 mmol), tetrabutylammonium bromide (2.15 g, 6.6 mmol) and methyl iodide (58 g, 475.41 mmol) in CH2Cl2 (150 mL) were added to NaOH (13.5 g, 337.5 mmol) in water (130 mL). The reaction mixture was stirred for 20 hours at RT. The organic layer was separated, was dried over Na2SO4, and was evaporated to dryness. The residue was dissolved in diethylether, was filtered over celite and solvent was evaporated to obtain the title compound. Yield: 18 g (76%); 1H NMR (CDCl3, 300 MHz): delta 8.220-8.250 (d, 2H, J=9 Hz), 7.627-7.657 (d, 2H, J=9 Hz), 1.750 (s, 6H).

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

Reference:
Patent; Kumar, Sanjay; Vishwakarma, Ram; Mundada, Ramswaroop; Deore, Vijaykumar; Kumar, Pramod; Sharma, Somesh; US2012/108627; (2012); A1;,
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Application of 6629-04-5, These common heterocyclic compound, 6629-04-5, name is N-Cyanoacetylurethane, 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 6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one (67) (1O g, 30.47 mmol) in glacial acetic acid (60 mL) and concentrated hydrochloric acid (9.06 mL) cooled to 5-100C was treated dropwise with a solution of sodium nitrite (2.3 g, 32.3 mmol) in water (6 mL). The reaction was stirred at 5-100C for 30 min. At this time, EPO the reaction was treated with N-cyanoacetylurethane (5.34 g, 33.52 mmol) followed by a solution of sodium acetate (7.5 g, 91.41 mmol) in water (22.5 mL). The reaction was stirred at 5-100C for 30 min and then was diluted with water (50 mL). The resulting solids were collected by filtration, washed with a 1:1 mixture of glacial acetic acid:water (40 mL) followed by water (2 x 60 mL), dried under house vacuum, and then dried under vacuum at 500C to afford (2-cyano-2-{ [3,5-dichloro-4-(5-isopropyl-l-methyl-6-oxo-l,6-dihydro- pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (68) (15.04 g, 95%) as an orange solid; ES(+)-LRMS for C20H20Cl2N6O5 (M+H)+ at m/z = 495. Exact Mass = 494.0872; Molecular Weight = 495.33.

Statistics shows that N-Cyanoacetylurethane is playing an increasingly important role. we look forward to future research findings about 6629-04-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/9913; (2007); A1;,
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Some common heterocyclic compound, 6609-56-9, name is 2-Methoxybenzonitrile, molecular formula is C8H7NO, 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. SDS of cas: 6609-56-9

General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6609-56-9, its application will become more common.

Reference:
Article; Pramanick, Pranab Kumar; Hou, Zhen-Lin; Yao, Bo; Tetrahedron; vol. 73; 50; (2017); p. 7105 – 7114;,
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Related Products of 79463-77-7, 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Example 1-177 [(7-Chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amino]-morpholin-4-yl-methylene-cyanamide To a stirred solution of 3-(aminomethyl)-7-chloro- l-phenylquinolin-4(lH)-one(intermediate D) (30 mg, 0.105 mmol) and N,N-diisopropylethylamine (40.9 mg, 55.2 muL·, 0.316 mmol) in NuMuRho (0.5 mL) was added diphenyl-cyanocarbonimidate (25.1 mg, 0.105 mmol). After 1 hr., morpholine (11.9 mg, 12.0 mu?^, 0.137 mmol) was added and the mixture was warmed to 120 I in a sealed microwave tube. After lhr., LCMS showed complete conversion to product. The mixture was allowed to cool to room temp, and the crude product was purified using preparative reverse-phase HPLC. The product [(7- chloro-4-oxo- 1 -phenyl- 1 ,4-dihydro-quinolin-3ylmethyl)-amino]-morpholin-4-yl- methylene-cyan- amide (25 mg, 56%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-cfo) 6 ppm 8.26 (d, 7=8.8 Hz, 1 H) 8.07 (s, 1 H) 7.61 – 7.76 (m, 3 H) 7.57 – 7.62 (m, 2 H) 7.48 – 7.53 (m, 1 H) 7.46 (dd, .7=8.8, 1.9 Hz, 1 H) 6.93 (d, 7=1.9 Hz, 1 H) 4.36 (d, 7=4.8 Hz, 2 H) 3.51 – 3.62 (m, 4 H) 3.35 – 3.46 (m, 4 H).

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, Diphenyl N-cyanocarbonimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BILOTTA, Joseph Anthony; CHEUNG, Adrian Wai-Hing; FIROOZNIA, Fariborz; GUERTIN, Kevin Richard; HAYDEN, Stuart; HAYNES, Nancy-Ellen; LUKACS-LESBURG, Christine M.; MARCOPULOS, Nicholas; MERTZ, Eric; QI, Lida; QIAN, Yimin; SO, Sung-Sau; TAN, Jenny; THAKKAR, Kshitij Chhabilbhai; WO2013/7676; (2013); 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. category: nitriles-buliding-blocks

1 mmol of the starting material CN-1-1, 3.0 mmol of potassium carbonate and 2.5 mmol of the starting material F-8-2, Was added to 10 mL of dimethylsulfoxide and heated at 150 C for 8 hours. After cooling to room temperature, 200 mL of water was added to the system to precipitate a solid which was purged and purified by column chromatography to give a solid.

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; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Huang Da; Cao Chenhui; Xie Zaifeng; Ma Tengda; (39 pag.)CN107011243; (2017); A;,
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