Month: February 2021

Related Products of 7149-75-9, 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. 7149-75-9 name is 4-Chloro-3-methylaniline, 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: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-methylaniline, and friends who are interested can also refer to it.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 863111-48-2, name is 2-Bromo-5-chloro-4-(trifluoromethyl)aniline, belongs to chlorides-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 863111-48-2, SDS of cas: 863111-48-2

Example 158: (R S)-3-(5-Chloro-2-f(E)-3-f3-(4-fluoro-benzyl(at)3.8-diaza-bic cly o(at)3.2.11oct-8-yll- 3-oxo-roDenvl)-4-trifluoromethvl-Dhenyll-5-methvl-imidazolidine-2,4-dione; a) (R)-2-(at)3-(2-Bromo-5-chloro-4-trifluoromethvl-ahenyl)-ureidol-propionic acid methyl ester; To a solution of 2-bromo-5-chloro-4-trifluoromethoxyaniline (0.5 g, 1.8 mmol) and triethylamine (0.63 ml, 4.6 mmol) in 12 ml chloroform is added triphosgene (0.22 g, 0.73 mmol) in one portion. After stirring at room temperature for 5 hours first triethylamine (0.30 ml, 2.2 mmol) then D-alanine methyl ester x HCI (0.25g, 1.8 mmol) is added and the mixture is stirred at 65 C for 16 hours. The reaction mixture is poured onto sodium bicarbonate solution followed by extraction with ethylacetate, drying and concentration. Chromatography gave 0.34 g (0.9 mmol, 50%) of the title compound. 1H-NMR (400MHz; DMSO-d6), No. (ppm) : 1.34 (d, 3H), 3.66 (s, 3H), 4.25 (dq, 1H), 7.94 (d, 1 H), 7.99 (s, 1H), 8.42 (s, 1 H), 8.48 (s, 1 H). MS (m/z) ESI-: 401 (100, M-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, 2-Bromo-5-chloro-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/103054; (2005); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4863-91-6, 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 4863-91-6 as follows.

Example 9: Synthesis of Compound 38 Compound 38 [0111] A flame-dried flask was charged with 5-chlorobenzo[c][l,2,5]oxadiazole (100.0 mg, 0.65 mmol, 1 equiv) and toluene (3mL), and the mixture was stirred at 1 10 C for 30 min with a reflux condenser. The solution was cooled to room temperature, and the flask was charged sequentially with palladium (II) acetate (8.8 mg, 0.040 mmol, 6 mol%), racemic 2,2′- bis(diphenylphosphino)-l, l’-binaphthyl (24.9 mg, 0.040 mmol, 6 mol%), 2-chloro-4- fluoroaniline (68.4 mu,, 0.65 mmol, 1 equiv) and potassium tert-butoxide (80.0 mg, .71 mmol, 1.1 equiv). The mixture was stirred at 90 C for 12 h, cooled to room temperature, and diluted with water. The mixture was washed with dichloromethane (3x). The combined organic layers were washed with IN HC1, IN NaOH, and brine. The organic layers were then dried over MgS04 and concentrated under reduced pressure. The resulting solid was then recrystallized in hexanes to provide compound 38 as a brown solid (67 mg, 39% yield): XH NMR (400 MHz, Acetone-d6) 8.59 (bs, 1H), 7.87 (d, J = 9.2 Hz, 1H), 7.40 (dd, J= 2.0 Hz, 9.6 Hz, 1H), 7.31 (m, 1H), 7.20 (s, 1H), 7.12 (dt, J= 1.3 Hz, 12.0 Hz, 1 Hz), 6.92 (dt, J= 2.0 Hz, 8.6 Hz, 1H); 13C NMR (100 MHz, Acetone-d6) 164.4 (d, J = 245.3 Hz), 151.1, 147.9, 145.4, 144.9 (d, J = 1 1.9 Hz), 136.3 (d, J = 13.2 Hz), 131.0, 118.2, 1 16.3, 1 10.6 (d, J = 25.5 Hz) 105.9 (d, J= 25.0 Hz), 91.7; LCMS (ESI) calc’d for [Ci2H6ClFN30]”([M-H]”): m/z 262.0, found 262.0.

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 367-22-6, These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, 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.

4-Chloro-3-fluoro-phenylamine (10 g, 68.7 mmol) was dissolved in dichloromethane (38 ml) and treated with sodium bicarbonate (6.82g, 72.1 mmol) in water (100 ml). At rt methyl chloroformate (8 ml, 103.0 mmol) was added dropwise over a period of 25 min (temperature raises from 22 to 28 C.). After 1.5 h stirring at rt, the reaction mixture was diluted with dichloromethane (100 ml). After separation, the organic phase was washed with sat. aq. NaCl solution (45 ml), dried over magnesium sulfate, filtered and diluted with hexane (140ml). The dichloromethane was then removed under vacuo and the resulting suspension filtered leading to (4-chloro-3-fluoro-phenyl)-carbamic acid methyl ester (13g, 92%) as a white powder. MS (EI) 203.1 (M)+.

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185182; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4584-46-7,Some common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, molecular formula is C4H11Cl2N, 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-(2,4-dimethoxy-benzyl)-4-hydroxy-isoindole-1 ,3-dione (317 mg, 1.01 mmol), 2- dimethylaminoethyl chloride hydrochloride (160 mg, 1.11 mmol) and potassium carbonate (350 mg, 2.5 mmol) in DMF (4 mL) was heated at 6O0C for 18 hours. The mixture was concentrated in vacuo, taken up in ethyl acetate and extracted twice with 1 N hydrochloric acid. The aqueous extracts were made basic with solid potassium carbonate and extracted with ethyl acetate (*2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give the title compound (236 mg, 61%) as an off-white solid. 1H NMR (methanol-d4) 7.73 (1H, t), 7.44-7.40 (2H, m), 7.02 (1 H, d), 6.51 (1 H, d), 6.42 (1 H, dd), 4.72 (2H, s), 4.33 (2H, t), 3.80 (3H, s), 3.76 (3H, s), 2.87 (2H, t), 2.40 (6H, s). MS: [M+H]+ 385.

The synthetic route of 4584-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, belongs to chlorides-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 61881-19-4, HPLC of Formula: C8H5ClF3N

To a solution of the hemiacetal 28 in acetone (10mL) and water (50muL), Cs2CO3 (189mg, 0.6mmol) and (N-phenyl)trifluoroacetimidoyl chloride (56muL, 0.4mmol) were added at room temperature. The reaction mixture was stirred for 3h at room temperature. After complete reaction (monitored by TLC), the mixture was filtered through Celite by elution with chloroform. The combined filtrates were concentrated and purified by flash chromatography (solvent D) to yield compound 29 (236mg, 87%) as a colorless foam: [alpha]D23 +164.2 (c 0.3, CHCl3); Rf=0.57 (solvent B2); 1H NMR (500.13MHz, CDCl3): delta 8.08 (m, 2H), 7.97 (m, 2H), 7.81 (m, 2H), 7.61-7.56 (m, 4H), 7.49-7.42 (m, 4H), 7.41-7.08 (m, 22H), 7.05 (m, 2H), 6.83 (m, 2H) (4 CH2C6H5, 3 COC6H5, NC6H5); 6.27 (br, 1H, H-1); 5.93 (dd, 1H, 3J2?,3?=10.7Hz, 3J3?,4?=3.5Hz, H-3?); 5.78 (dd, 1H, 3J2,3=3.0Hz, 3J1,2=2.0Hz, H-2); 5.58 (dd, 1H, 3J3?,4?=3.5Hz, 3J4?,5?=1.4Hz, H-4?); 5.46 (d, 1H, 3J1?,2?=3.3Hz, H-1?); 5.07 (dd, 1H, 3J2?,3?=3.3Hz, 3J1?,2?=1.9Hz, H-2?); 5.08, 4.94 (2d, 2H, 2J=10.4Hz, CH2C6H5); 4.89 (d, 1H, 3J1?,2?=1.9Hz, H-1?); 4.74, 4.58 (2d, 2H, 2J=11.4Hz, CH2C6H5); 4.68 (m, 1H, H-5?); 4.55 (dd, 1H, 3J3,4=9.8Hz, 3J2,3=3.0Hz, H-3); 4.50 (dd, 1H, 3J2?,3?=10.7Hz, H-2?); 4.24 (center of qAB, 2H, 2J=12.2Hz), 4.15, 3.43 (2d, 2H, 2J=10.7Hz), (2 CH2C6H5); 4.03 (dq, 1H, 3J4,5=9.2Hz, 3J5,6=6.1Hz, H-5); 3.98 (dq, 1H, 3J4?,5?=9.1Hz, 3J5?,6?=6.3Hz, H-5?); 3.98 (?t?, 1H, 3J3,4=9.8Hz, 3J4,5=9.5Hz, H-4); 3.43 (dd, 1H, 3J5?,6a?=6.3Hz, H-6a?); 3.31 (dd, 1H, 2J6a?,6b?=10.2Hz, 3J5?,6b?=5.7Hz, H-6b?); 3.26 (dd, 1H, 3J3?,4?=8.8Hz, 3J2?,3?=3.3Hz, H-3?); 3.23 (?t?, 1H, 3J4?,5?=9.1Hz, H-4?); 1.63 (s, 3H, COCH3); 1.54 (d, 3H, 3J5,6=6.1Hz, H-6); 1.39 (d, 3H, 3J5?,6?=6.3Hz, H-6?); 13C NMR (125.8MHz, CDCl3): delta 168.8 (COCH3); 165.1, 165.2, 165.5 (3 COC6H5); 143.2 (i-NC6H5); 137.4, 137.8, 138.2, 138.9 (4 i-CH2C6H5); 133.4, 133.3, 133.0 (3 p-COC6H5); 130.6-127.2 (several signals of o-, m-COC6H5, o-, m-, p-CH2C6H5, m-NC6H5); 129.5, 129.3, 128.8 (3 i-COC6H5); 124.4 (p-NC6H5); 119.4 (o-NC6H5); 115.9 (q, 1JC,F=287Hz, CF3); 100.0 (C-1?); 94.4 (C-1?); 93.7 (br, C-1); 79.9 (C-4?); 79.0 (C-4); 77.8 (C-3?); 76.3, 75.0, 72.8, 71.2 (4 CH2C6H5); 71.7 (C-2?); 71.5 (C-3); 71.3 (C-5); 70.8 (C-3?); 69.8 (C-4?); 68.5 (C-5?); 68.4 (C-2?); 67.8 (C-6?); 67.3 (C-5?); 66.7 (C-2); 20.3 (COCH3); 18.4 (C-6); 18.1 (C-6?); CCF3 signal not given; 19F NMR (282.4MHz, CDCl3): delta -75.7 (CF3). HRMS (ESI-TOF): calcd for C77H74F3NO18 (M+Na+): m/z 1380.4750, found: m/z 1380.4751.

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, 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nilsson, Inga; Michalik, Dirk; Silipo, Alba; Molinaro, Antonio; Vogel, Christian; Carbohydrate Research; vol. 404; (2015); p. 98 – 107;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 45-Amino-N-(4-ch[oro-3-f[uoropheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide A mixture of 5-amino-3-methy[-1 ,2-thiazo[e-4-carboxy[ic acid [CAS-RN: 22131 -51 -7,for the synthesis, p[ease see: J. Goerde[er, H. Horn, Chem. Ber. (1963), 96, 1551-1560.] (5.00 g, 9.93 mmo[, 1.0 eq) and thiony[ ch[oride (20.7 mL, 284 mmo[,9.0 eq) was stirred at 80 C for 2 h. After coo[ing, the vo[ati[e components were removed in vacuo. The crude acid ch[oride was di[uted with to[uene and concentrated at the rotary evaporator. This process was repeated one more time.The acid ch[oride (1.75 g, 9.93 mmo[, 1.0 eq) observed this way was disso[ved in THF (15 mL). Then, 4-ch[oro-3-f[uoroani[ine [CAS-RN: 367-22-6] (2.89 mL, 19.9 mmo[, 2.0 eq) and triethy[ amine (2.01 mL, 19.9 mmo[, 2.0 eq) was added. The reaction mixture was stirred at rt overnight. After addition of water the crude reaction mixture was acidified with 1M hydroch[oric acid and extracted with EtOAc.The organic phase was washed with brine and dried with sodium su[fate. After remova[ of the vo[ati[e components the product was crysta[[ized from dich[oromethane and methano[. The precipitate was iso[ated by fi[tration and dried under high vacuum to give the tit[e compound (600 mg, 21% yie[d of theory based on the intermediate acid ch[oride).UPLC-MS (Method 2): Rt = 1.06 mm; MS (Elneg) m/z = 284 [M-H].1HNMR (400 MHz, DMSO-d6): oe [ppm] = 2.36 (s, 3H), 7.28 (s br, 2H), 7.41 (dd, 1H),7.51 (t, 1H), 7.81 (dd, 1H), 9.82 (s, 1H).

The synthetic route of 4-Chloro-3-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 39885-50-2,Some common heterocyclic compound, 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline, molecular formula is C7H5ClF3N, 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.

To a solution of ethyl (2E) -3- (4- (2-methoxyethoxy) -2- { [ (trifluoromethyl) sulfonyl] oxy}phenyl) acrylate (1.66 g) in tetrahydrofuran (20 ml) were added 2-chloro-4- . (trifluoromethyl) aniline (1.89 g) , racemic-2, 2′ – bis(diphenylphosphino)-l,l’-binaphthyl (519 mg) , palladium acetate (140 mg) and cesium carbonate (2.06 g) , and the mixture was heated under reflux for 8 hr. After cooling, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl -acetate layer was washed with saturated brine, dried (MgSO4) , and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give ethyl (2E) -3- [2-{ [2-chloro-4- (trifluoromethyl) phenyl] amino} -4- (2- methoxyethoxy) phenyl] acrylate (1.00 g, yield: 54percent) as yellow crystals.1H-NMR (300 MHz, CDCl3) 6:1-29 (3 H, t, J = 7.2 Hz), 3.44 (3 H, s) , 3.73 – 3.79 (2 H, m) , 4.16 – 4.27 (4 H, m) , 6.23 (1 H, s) , 6.34 (1 H, d, J = 15.9 z) , 6.55 – 6.59 (1 H, m) , 6.85 – 6.91 (2 H, m),.7.32 – 7.62 (-3 H, m) , 7.77 (I H, d, J = 15.9 Hz)..

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/18314; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 61881-19-4

General procedure: t-BuOK (40.3mg, 0.36mmol) were added to a solution of fluorinated imidoyl chlorides 1 (0.45mmol) and isocyanides 2 (0.3mmol) in DMF (2.0mL). The mixture was stirred at 60C under air for 1h. After the completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambient temperature, quenched by water and extracted with ethyl acetate (3¡Á15mL). The extract was dried over anhydrous Na2SO4 and the solvent was removed in vacuo to provide a crude product, which was purified by column chromatography on silica gel with petroleum ether/EtOAc as eluent to afford the imidazole products 3.

The synthetic route of 61881-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Zhengkai; Hu, Sipei; Wu, Xiao-Feng; Yang, Hefei; Tetrahedron; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 60811-21-4, 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. 60811-21-4 name is 4-Bromo-2-chloro-1-fluorobenzene, 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: To a 250 mL three-necked flask was added magnesium turnings (3.60 g, 150 mmol) and anhydrous THF (150 mL) under argon. A few drops of 1,2-dibromoethane were added followed by the slow addition of 1-bromo-4-fluorobenzene (13.1 g, 75.0 mmol). The solution was stirred at ambient temperature for 40 min, then cooled to 0 C, at which time the solution was added slowly to 2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylacetamide 6 (10.0 g, 42.8 mmol) in THF (150 mL). The resultant mixture was stirred at 0 C for 3 h, then quenched with saturated NH4Cl (100 mL). The mixture was extracted with CH2Cl2 (3 ¡Á 100 mL) and the combined organic phases washed with water (3 ¡Á 100 mL), dried (Na2SO4), and concentrated. The residue was purified by column chromatography (1:20 EtOAc/petroleum ether) to afford 10 g (91%) of 2-(tert-butyldimethylsilyloxy)-1-(4-fluorophenyl)ethanone as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-chloro-1-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Pan, Xingang; Jia, Liangbin; Liu, Xuejian; Ma, Haikuo; Yang, Wenqian; Schwarz, Jacob B.; Tetrahedron Asymmetry; vol. 22; 3; (2011); p. 329 – 337;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics