Tag: M.W=200-300

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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H16N2O2

General procedure: To a round-bottom flask equipped with a stir bar was added 28a-b (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (10 mL/mmol). The reaction was refluxed and stirred in a pre-heated 75 C. oil-bath for 6 h. After cooling to room temperature, the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo and further purified on a silica gel column. Example 89 Synthesis of 215 tert-Butyl (E)-(4-(N?-hydroxycarbamimidoyl)benzyl) carbamate (29a) (0246) The synthesis follows the general procedure described in Example 88. Yield: 65%. MP: 142-145 C. 1H NMR (400 MHz, DMSO-d6) delta 9.57 (s, 1H, -OH), 7.61 (d, J=8.1 Hz, 2H, -ArH), 7.40 (t, J=6.1 Hz, 1H, -NHCO-), 7.22 (d, J=8.1 Hz, 2H, -ArH), 5.77 (s, 2H, -NH2), 4.13 (d, J=6.1 Hz, 2H, -ArCH2-), 1.40 (s, 9H, -CH3).

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; Washington University; Tu, Zhude; Rosenberg, Adam; Liu, Hui; Han, Junbin; US2019/2450; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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 36282-26-5, category: nitriles-buliding-blocks

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25.00 mmol), bis(pinacolato)diboron (9.52 g, 37.5 mmol), potassium acetate (7.36 g, 75.0 mmol), in dioxane (50 mL) argon was purged for 5 mins. PdCl2(dppf)-CH2Cl2 adduct (12.25 g, 15.00 mmol) was added and argon was bubbled through the reaction mixture and heated at 94 C (silicon oil bath) for 14 h. The reaction mixture was cooled to RT, filtered through celite pad, washed with ethyl acetate (200 mL). The organic layer was washed with water (100 mL) and the aq. layer was separated and re-extracted with ethyl acetate (2 x 100 mL). Combined organic extracts were washed with brine, dried over sodium sulfate and solvent was removed under reduced pressure to give the brown colored crude product. The product was purified by silica gel column chromatography using ethyl acetate in pet ether as an eluant to afford 89A (4 g, 16.19 mmol, 64.8 % yield) as a off- white semi solid. NMR (400 MHz, CDC13) d 7.89-7.93 (m, 1H), 7.54-7.59 (m, 1H), 7.39-7.50 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); A1;,
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Synthetic Route of 1114546-30-3,Some common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, molecular formula is C8H5BrFN, 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 4-bromo-2-fluoro-3- methylbenzonitrile (7.0 g, 32.7 mmol), potassium vinyltrifluoroborate (5.3 g, 39.3 mmol), Pd(dppf)Cl2 (0.5 g, 0.7 mmol) and TEA (30 mL) in EtOH (70 mL) was refiuxed under Ar for 4 hours. After being cooled to room temperature, the reaction mixture was concentrated and the residue was purified by column chromatography (petrol ether : EtOAc = 10 : 1) to afford 2- fluoro-3-methyl-4-vinylbenzonitrile as a white solid.

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
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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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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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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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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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Electric Literature of 114897-91-5,Some common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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: 4-Bromo-2-fluoro-phenyl-acetic acid(4-Bromo-2-fluoro-phenyl)-acetonitrile (41.4 g, 174 mmol) (21.2 g, 99.1 mmol) was suspended in 30% aq. HCI (200 ml.) and heated to reflux for 20 hours. After cooling to room temperature, the solids were collected by filtration, washed with water and allowed to dry in open air. The solids were azeotroped with toluene under reduced pressure to remove the final traces of water, yielding the title compound as a solid (21 .7 g, 89 mmol, 94%).1 H-NMR (CD3OD, 300 MHz): 3.68 (s, 2H); 7.20-7.4 (m, 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-(4-Bromo-2-fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; PFIZER INC.; BROWN, Matthew Frank; MARFAT, Anthony; MELNICK, Michael Joseph; REILLY, Usa; WO2011/45703; (2011); A2;,
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Application of 1735-53-1, 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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Description 21; 4-(2-methylpropyl)-3-(trifluoromethyl)benzamide (D21); To a solution of 4-bromo-3-trifluoromethylbenzonitrile (1.25 g, 5.0 mmol) and isobutylzinc bromide (25 mmol) in THF (50 ml_, 25 mmol) under argon was added1 ,1 ‘-bis(diphenylphosphino)ferrocenedichloro palladium(ll) dichloromethane complex(612 mg, 0.75 mmol) and the reaction heated at reflux for 5 h. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (80 ml.) and water (80 ml_). A solid formed and was filtered off and discarded. The organic layer was washed with water (80 ml.) before it was dried (phase separator) and concentrated in vacuo to give the crude title compound as a black oil. This was used directly in the next step (1.35 g).

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-Bromo-3-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74820; (2008); A1;,
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Reference of 950596-58-4,Some common heterocyclic compound, 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, molecular formula is C13H18N2O4, 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 1 (0025) In a reaction flask, 2-amino-4,5-bis(2-methoxyethoxy)-benzonitrile (37.01 g, 0.139 mol) and acetonitrile (185 ml) were charged; 3-ethynylaniline hydrochloride (30.00 g, 0.195 mol), trifluoroacetic acid (17.43 g, 0.152 mol) and formamidine acetate (15.19 g, 0.145 mol) were added to the resultant mixture. The reaction mixture was brought to the reflux temperature of the solvent and maintained under such conditions for about fifteen hours. At the end of the reaction, the temperature was brought to about 25 C., the solvent was removed by distillation under vacuum and methylethylketone (430 ml) was added. The organic phase was washed with a saturated sodium bicarbonate solution (2×100 ml) and with water (2×100 ml). The collected organic phases were concentrated to residue by distillation under vacuum. (0026) The resultant raw product was suspended in ethyl acetate (450 ml) and a solution of hydrochloric acid at 37% (14.38 g, 0.145 mol) was added, maintaining the temperature at 15 C. for about thirty minutes. The resultant solid was filtered, washed and dried in oven under vacuum at 45 C. to give 36.02 g of Erlotinib HCl.

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-4,5-bis(2-methoxyethoxy)benzonitrile, its application will become more common.

Reference:
Patent; CERBIOS-PHARMA SA; BARATELLA, Marco; PALLANZA, Giuseppe; GABOARDI, Mauro; CASTALDI, Graziano; (7 pag.)US2016/115137; (2016); A1;,
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