Author: Jessica.F

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. 4152-90-3, name is (3-Chlorophenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (3-Chlorophenyl)methanamine

General procedure: Benzylamine (0.214 g, 2.00 mmol), [VO(PS-BBMA]SO4 (80 mg, 0.08 mmol) and H2O2 (4 mmol) was heated at 80 C for 10 h in a round bottom flask under nitrogen atmosphere. The reaction was monitored by TLC, and after complete consumption of benzylamine, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate: hexane=1:8) to afford benzamide. The product was analyzed by 1H NMR spectroscopy.

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:
Article; Renuka; Gayathri; Catalysis Communications; vol. 121; (2019); p. 89 – 94;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 54932-72-8, A common heterocyclic compound, 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, molecular formula is C7H6BrCl, 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.

(1) A mixture of 5.00 g (24.3 mmol) of 5-bromo-2-chlorotoluene, 3.56 g (29.2 mmol) of dihydroxyphenylborane, 546mg (2.43 mmol) of palladium acetate (II), 9.41 g (29.2 mmol) of tetrabutylammonium bromide, 8.40 g (60.8 mmol) of potassium carbonate and 50 ml of water was stirred for 5 hours at 80 C. under nitrogen flow. The reaction solution was filtrated through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane) to obtain 3.92 g of 4-chloro-3-methylbiphenyl. 1H-NMR (CDCl3, TMS) delta (ppm): 7.30-7.60 (8H, m), 2.44 (3H, s)

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; Araki, Tomohiro; Kinoshita, Yoshiharu; Sakaguchi, Hiroshi; Manabe, Akio; US2003/119670; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 461432-23-5, 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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

At -78 & lt; 0 & gt; C,A solution of n-butyllithium in n-hexane(120.9 mL, 290 mmol, 7.2 M) was added dropwise2- (4-ethoxyphenyl) methyl-4-bromo-1-chlorobenzene(90 g, 276.3 mmol,Purchased in Shanghai Jinsai Pharmaceutical Company)Of anhydrous tetrahydrofuran(750 mL)After stirring at -78 & lt; 0 & gt; C for 40 min,(3R, 4S, 5R, 6R) -3,4,5-tris (trimethylsiloxy) -6 – [(trimethylsiloxy) methyl] -tetrahydropyran-2-one 1b (141.9 g, 304 mmol)ofAnhydrous tetrahydrofuran(150 mL)The solution was added dropwise to the reaction system.Drop finished,Stirring was continued at -78 & lt; 0 & gt; C for 5 hours.At -78 & lt; 0 & gt; C,The reaction was quenched by the slow addition of 300 mL of saturated ammonium chloride solution, warmed to room temperature and concentrated in vacuo to remove most of the solvent. The residue was added to 450 mLWater, extracted with ethyl acetate (450 mL x 3). The organic phases were combined and washed with saturated brine (600 mL) and dried over anhydrous sodium sulfateThe filtrate was concentrated under reduced pressure to give the title compound lc (208.9 g, pale yellow oil) in 100% yield. Crude productDirectly for the next step.

The synthetic route of 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Zhonghaikang Pharmaceutical Co., Ltd.; Zhou Di; Lin Fengwei; Jiao Shuang; Wen Bo; Huang Hai; (29 pag.)CN106674245; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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