Tag: M.W=100-200

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 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

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

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

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

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

Application of 29671-92-9, 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. 29671-92-9, name is Carbamimidic chloride hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 320 Synthesis of 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one A mixture of ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate (0.3 g, 1.13 mmol), chloroformamidine hydrochloride (0.33 g, 2.83 mmol) and dimethylsulfone (0.53 g, 5.65 mmol) was heated at 120-130 C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension. The solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1) to yield the title compound as a white solid (0.28 g, 95%). 1H NMR (300 MHz, DMSO, 25 C.): delta=11.05 (s, 1H, NH), 7.66-7.71 (m, 2H, PhH), 7.51 (s, 1H, CH), 7.23 (t, J=8.8 Hz, PhH), 6.73 (s, 2H, NH2) ppm. HRMS: calcd for C12H9FN3OS 262.04504. found 262.04413.

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, Carbamimidic chloride hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Katholieke Universiteit Leuven, K.U. Leuven R&D; Herman, Jean; Louat, Thierry; US2014/88088; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 103889-37-8, name is 1-Chloro-3-fluoro-2-(trifluoromethyl)benzene, 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 103889-37-8, Recommanded Product: 1-Chloro-3-fluoro-2-(trifluoromethyl)benzene

To a solution of conc. H2S04 (3 mL) and conc. HNO3 (3 mL) was added 1-chloro- 3-fluoro-2-(trifluoromethyl)benzene (1.00 g, 5.05 mmol) at 0C. The reaction mixture was stirred at 0C for 30 minutes and at room temperature for 2 h, then poured into icecold H20 (50 mL) and extracted with EtOAc (2 x 50 mL). The organic layer was washed with H20 (100 mL) and brine (100 mL). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 20% EtOAc in hexanes) to afford the title compounds (mixture of isomers; 1.00 g, 82%) as a yellow liquid. ; To a solution of Intermediate 6 (0.25 g, 0.64 mmol) and Intermediate JO (as a mixture of isomers) (0.78 g, 3.23 mmol) in THF (12 mL) was added 1.8M tert-butyl10 lithium solution (1.90 mL, 3.23 mmol) dropwise at -78C. The reaction mixture wasstirred at -78C for 30 minutes and at room temperature for 16 h, then quenched with brine (100 mL) and extracted with EtOAc (2 x 50 mL). The organic layer was separated, and washed with H20 (100 mL) and brine (100 mL), then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography(silica, 100-200 mesh, 30% EtOAc in hexanes) to afford the title compound (80% purity by LCMS) (0.12 g, 30%) as a yellow solid. oH (400 MHz, CDC13) 1.58 (m, 9H), 1.92 (s, 3H), 3.25 (s, 3H), 3.72 (d, J 14.1 Hz, 1H), 4.22 (d, J 14.1 Hz, 1H), 6.81 (t, J7.9 Hz, 1H),6.94-7.08 (m, 2H), 7.36 (d, J8.9 Hz, 1H), 7.95 (s, 1H), 8.13 (d, J8.9 Hz, 1H), 10.62 (s, 1H). LCMS (Method 1, ES+) 594 [M+lf?, 3.81 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-3-fluoro-2-(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; DE HARO GARCIA, Teresa; LOWE, Martin Alexander; MACCOSS, Malcolm; TAYLOR, Richard David; ZHU, Zhaoning; (47 pag.)WO2017/144517; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 20850-43-5, 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 20850-43-5 as follows.

Preparation of 1, 3-benzodioxol-5-ylmetlyl ethyl sulfone 8.6 g of 5-(chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetrahydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C. The reaction was done for 10 minutes and then for 1 hour at 50C. The reaction mixture was cooled to 0C and then slowly added to the flask containing [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 3.7 ml ethane sulfonyl chloride, the mixture was reacted for 30 minutes. The reactant was then heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column chromatography using ethyl acetate: n-hexane (1: 3), to give 0.3 g of the title compound of the following formula lb (Rf: 0.35, Yield: 3%). [Chemical Formula 1b] The compound was dissolved in CDC13 and TMS and then characterized by’H NMR spectroscopy. The result is as follows; ‘H NMR 5 : 1.57-1. 64 (t, 3H, J=7.3Hz), 2.78 (s, 2H), 3.60-3. 78 (q, 2H, J=7.3Hz), 5.90 (s, 2H), 6.56-6. 79 (m, 3H).

According to the analysis of related databases, 20850-43-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 53145-38-3, These common heterocyclic compound, 53145-38-3, name is 2-Chloro-6-fluoroanisole, 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.

5. Preparation of 4-chloro-2-fluoro-3-methoxybenzaldehyde To a solution of 2-chloro-6-fluoroanisole (321.2 g) in 2 L of dry tetrahydrofuran (THF), cooled to -70 C., was added 890 mL of 2.5 M n-BuLi in hexane over 30 min with good mechanical stirring. During the addition the reaction warmed to -48 to -50 C. and was held there for 15 min after addition was complete. The solution was cooled to -75 C. before a solution of 177 g of dimethylformamide (DMF) in 100 mL of THF was added keeping the temperature below -50 C. The reaction was warmed to room temperature and 260 g of 37% aqueous HCl was slowly added and stirring was continued for 2 hours. The phases were separated and the organic phase concentrated and taken into 2 L of ether. The solution was washed twice with 500 mL of aqueous 10% HCl. The organic phase was dried over MgSO4, filtered and concentrated to 372 g of a light gold oil (93% pure by GC). This oil was distilled bulb to bulb to give 282 g (75% yield) of a light gold oil that solidified upon standing. A small sample was crystallized from pentane to give fine white needles; MP 44-45 C.; 1H NMR (CDCl3, 300 MHz) delta 10.3 (s, 1H); 7.5 (dd, 1H, J=6.6, 8.5 Hz); 7.3 (m, 1H); 4.0 (s, 3H).

Statistics shows that 2-Chloro-6-fluoroanisole is playing an increasingly important role. we look forward to future research findings about 53145-38-3.

Reference:
Patent; Dow AgroSciences LLC; US2009/182168; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics