Tag: M.W=100-200

Related Products of 654-70-6, The chemical industry reduces the impact on the environment during synthesis 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, I believe this compound will play a more active role in future production and life.

Example 11; A/-[4-({3-[[4-Cyano-3-(trifluoromethyl)phenyl](2,2,2- trifluoroethyl)amino]propyl}oxy)phenyl]acetamide; A. 4-(2,2,2-Trifluoro-ethylamino)-2-trifluoromethyl-benzonitrile; To a slurry of 4-amino-2-(trifluoromethyl)benzonitrile (30.09 g, 162 mmol) and NaBH3CN (21.35 g, 340 mmol) in CH2CI2 (160 ml_) at ice bath temperature neat TFA (160 mL, 2.08 mol) was added dropwise at a rate such that the internal temperature remained below 50C (CAUTION: exothermic reaction with hydrogen gas evolution). EPO Trifluoroacetaldehyde hydrate (52.2 g, 405 mmol) was then added over 5 min (CAUTION: slightly exothermic reaction, with gas evolution). After 41 h, the mixture was slowly poured into sat’d NaHCO3 (1 L) at 00C. The mixture was then completely neutralized by portionwise addition of solid NaHCO3. The mixture was stirred 30 min and precipitated solids were collected by filtration. Organic and aqueous phases of the filtrate were separated, and the aqueous layer extracted with CH2CI2 (3 x 150 ml_). Combined organic extracts were concentrated to dryness, combined with the solids collected previously, dissolved in EtOAc, washed (H2O, brine), dried over Na2SO4, filtered through a short pad of Celite and concentrated to dryness. Recrystallization from EtOAc/hexanes yielded 32.61 g of the title compound as slightly tan crystalline plates, mp 132.5-134C: 1H NMR (300 MHz, CD3OD) delta 7.59 (d, J = 8.8 Hz, 1 H), 7.05 (d, J = 2.2 Hz, 1 H), 6.92 (dd, J = 8.7, 2.4 Hz, 1 H), 3.92 (q, J = 9.2 Hz, 2H).

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-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/44707; (2006); A1;,
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Electric Literature of 3939-09-1, The chemical industry reduces the impact on the environment during synthesis 3939-09-1, name is 2,4-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

2,4-Difluorobenzonitrile (50.0 g, 0.359 mol), trans-4-aminocyclohexanol (41.4 g, 0.359 mol, 1 eq.), and N,N-diisopropylethylamine (62.6 mL, 0.359 mol, 1 eq.) were dissolved in 300 mL of DMSO. The reaction vessel was outfitted with a reflux condenser to avoid loss of N,N-diisopropylethylamine. The reaction mixture was then placed in an oil bath that had been pre-heated to 150 C., and was stirred at this temperature for 20 minutes. The solution was then cooled, poured into 750 mL of saturated aqueous NH4Cl, and extracted with ethyl acetate (200 mL¡Á3). The combined organics were washed with brine (150 mL¡Á3), dried over Na2SO4, filtered, and concentrated in vacuo. The resultant residue was purified by column chromatography (1:1 ethyl acetate/hexane) to afford 20.9 g (25% yield) of the desired isomer as a white powder, and 36.1 g (43% yield) of the undesired isomer as a white powder.

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, 2,4-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
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These common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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. Product Details of 67832-11-5

To a solution of 4-bromo-2-methylbenzonitrile (2.0g, 10.2mmol) in THF (100ml) at -78C under a nitrogen atmosphere was added dropwise a 2.5M solution of n-butyl lithium (4.48ml, 11.2mmol). The mixture was stirred at -78C for lh and then poured onto solid carbon dioxide (5g) in THF (50ml). The mixture was allowed to warm to room temperature. Water was added (200ml) and the mixture was extracted with diethyl ether (3 times). The aqueous layer was acidified by addition of concentrated HC1 and extracted with chloroform (3 times). The combined chloroform extracts were washed with water, dried over MgS04, and concentrated in vacuo to give a white solid; yielding (73%).

The synthetic route of 4-Bromo-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERRING B.V.; WO2006/18443; (2006); A1;,
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Application of 67832-11-5, 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. 67832-11-5 name is 4-Bromo-2-methylbenzonitrile, 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.

[0617j To a solution of 4-bromo-2-methylbenzonitrile (3.0 g, 15 mmol) in anhydrous THF (20 mL) under nitrogen at 0 C was added 1.0 M solution of borane in THF (46 mL). The reaction mixture was stirred at 0 C for 1 h, and heated at 80 C overnight. The reaction mixture was cooled to 0 C and slowly quenched with MeOH, concentrated in vacuo. The crude product was treated with EtOAc (20 mL) and 4 M of HC1 in 1,4-dioxane (8.0 mL, 32 mmol) for 5 mm. The solid was filtered, rinsed with diethyl ether, dried to give the title compound as a white powder (3.24 g, yield: 100%). LCMS: RT 0.75 mm.; MH+ 200.0. ?H NMR (300 MHz, DMSOd6) 5: 8.28 (br. s., 2H), 7.42 – 7.54 (m, 2H), 7.34 (d, J = 7.93 Hz, 1H), 3.99 (d, J = 4.15 Hz, 2H), 2.35 (s, 3H).

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

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
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53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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. Application In Synthesis of 5-Amino-2-fluorobenzonitrile

To ethyl 3 -fluoro- 1 -methyl-4- [[( 1R)- 1 -methylpropyl] sulfamoyl]pyrrole-2-carboxylate(354 mg, 1.156 mmol) and 5-amino-2-fluoro-benzonitrile (201.7mg, 1.483 mmol) in dry THF(20 mL) at 0C, lithium bis(trimethylsilyl)amide in THF (4.62 mL, 4.62 mmol) was added. Themixture was stirred 1 hour at 0C. The reaction mixture was quenched with NH4C1 solution (30mL) and extracted with EtOAc (5OmL), diluted with brine (50 mL) and extracted again with EtOAc (50 mL). The combine organic layers were dried over sodium sulphate, filtered and concentrated. The residue (dissolved in 1 mL DMF) was purified by column chromatography on silica using a gradient from 10 till 100% EtOAc in heptane. The product fractions wereconcentrated and the solid residue was crystallized from 50 mL warm methanol upon addition of water. The white crystals were filtered off and dried in vacuo at 50C overnight, resulting in compound 186 (306 mg)MethodA: Rt: 1.83 minmlz: 395.1 (M-H) Exactmass: 396.11. ?H NMR (400 MHz, DMSO-d6) oe ppm 0.78 (t, J=7.4 Hz, 3 H), 1.01 (d, J=6.6 Hz, 3 H), 1.31 – 1.44 (m, 2 H), 3.06 – 3.20 (m, 1 H), 3.80 (s, 3 H), 7.47 (d, J=4.6 Hz, 1 H), 7.50 – 7.58 (m, 2 H), 7.96(ddd, J=9.2, 4.8, 2.9 Hz, 1 H), 8.17 (dd, J5.7, 2.6 Hz, 1 H), 10.31 (s, 1 H).

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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Some common heterocyclic compound, 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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: 455-18-5

A mixture of 4-trifluoromethylbenzonitrile 10 (0.350 g, 2.04 mmol), hydroxylamine hydrochloride (0.213 g, 3.07 mmol) and triethylamine (0.44 mL, 3.24 mmol) in ethanol (4 mL) was refluxed for 3 h. After the completion of the reaction, the solvent was evaporated the crude residue was dissolved in dichloromethane and washed with water and brine once. The organic layer was dried over magnesium sulfate, filtered and evaporated to give 11 as white solid (0.406 g, 99%); 1H NMR (300 MHz, Chloroform-d): delta 4.88 (br s, 2NH), 7.23 (s, 1H), 7.67 (d, J = 8.1 Hz, 2H), 7.76 (d, J = 8.1 Hz, 2H). The analytical data was consistent with literature data. 22

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 455-18-5, its application will become more common.

Reference:
Article; Teng, Yu-Han Gary; Berger, William T.; Nesbitt, Natasha M.; Kumar, Kunal; Balius, Trent E.; Rizzo, Robert C.; Tonge, Peter J.; Ojima, Iwao; Swaminathan, Subramanyam; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5489 – 5495;,
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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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-5-chlorobenzonitrile

Method B N-(4-Chloro-2-cyanophenyl)-2-(5-morpholin-4-ylbenzimidazol-2-yl)acetamide LiHMDS (2.5 eq) was added to ethyl 2-[5-(2-morpholin-4-ylethoxy)benzimidazol-2-yl]acetate (1.0 eq) in THF at -78¡ã C. After 1 hour, 2-amino-5-chlorobenzenecarbonitrile (0.82 eq) in THF was added. The reaction was allowed to warm to 23¡ã C. and stirred overnight. The resulting mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to give the desired product. LC/MS m/z 396.1 (MH+), Rf 1.79 minutes.

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chiron Coporation; US2003/28018; (2003); A1;,
Nitrile – Wikipedia,
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Application of 658-99-1,Some common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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 51 -(4-(5-(2-( 1 -(3 ,4-difluorophenyl)cyclohexyl)ethyl)- 1 ,2,4-oxadiazol-3 – yl)benzyl)azetidine-3-carboxylic acidPreparation 5 A: l-(3,4-difluorophenyl)cyclohexanecarbonitrile [0136] To a solution of 2-(3,4-difluorophenyl)acetonitrile (2 g, 13.06 mmol) in 20 mL of DMF at 0C was added 60% sodium hydride (1.149 g, 28.7 mmol), and the mixture was stirred at the same temperature for 5 mins. Then a solution of 1,5-dibromopentane (1.779 mL, 13.06 mmol) in 20 mL of DMF was added dropwise and the mixture was stirred at a temperature in the range 0C to room temperature for 5 hrs. The reaction was quenched with water, and extracted with EtOAc. The mixture was washed with water and brine. The combined aqueous layers were back extracted with EtOAc once and washed with brine. The combined extracts were dried over a2S04 and evaporated to give an oily residue. It was purified by Combiflash (120g silica gel) eluting with 1 :9 EtOAc-hexane to give l-(3,4-difluorophenyl) cyclohexanecarbonitrile (2.52 g, 1 1.39 mmol, 87 % yield). lH NMR (400 MHz, CC13D) delta ppm 7.12-7.35 (3 H, m), 2.14 (2 H, d, J= 11.86 Hz), 1.75-1.95 (6 H, m), 1.64-1.75 (2 H, m)

The synthetic route of 658-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DAS, Jagabandhu; KO, Soo Sung; SRIVASTAVA, Anurag; MOQUIN, Robert V.; WATTERSON, Scott H.; WO2012/12477; (2012); A1;,
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Application of 67832-11-5,Some common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-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.

EXAMPLE 164A 4′-methoxy-3-methyl-1,1′-biphenyl-4-carbonitrile 4-Bromo-2-methylbenzonitrile (4.9 g, 25.0 mmol), Pd(PPh3)4 (578 mg) in benzene (50 mL) and 2.0 M aqueous solution of Na2CO3 (25 mL, 50.0 mmol) was treated with 4-methoxyphenylboronic acid (4.56 g, 30.0 mmol) in ethanol (20 mL) and heated at 75 C. for 17 hours. The mixture was allowed to cool to room temperature and the phases were separated. The aqueous phase was extracted with diethyl ether (3*40 mL). The original benzene layer and the diethyl ether extracts were combined, filtered over celite, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography over silica using a mixture of hexane/CH2Cl2 (3:1) to provide the title compound as a white powder (5.73 g, 85% yield). 1H-NMR (300 MHz, CDCl3) delta2.35 (3H), 3.70 (s, 3H), 6.80-7.50 (m, 7H); MS (DCI) m/z 224 (M+H)+.

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

Reference:
Patent; Abbott Laboratories; US6620839; (2003); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 4714-62-9, name is 4-(Methylamino)benzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2

A mixture of the compound (450 mg) obtained in Step 1, 90% sodium azide (664 mg), triethylammonium chloride (703 mg) and anhydrous 1-methyl-2-pirrolidone (12 mL) was stirred at 140 to 160C for ten hours under nitrogen atmosphere. The reaction mixture was poured into ice-water, and the residue was adjusted to pH 3 with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from tert-butyl methyl ether, collected by filtration and dried to obtain the titled compound (471 mg) as crystals.

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; MOCHIDA PHARMACEUTICAL CO., LTD.; EP1391452; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts