Month: July 2021

Reference of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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 the stirred suspension of p-methoxybenzyl alcohol (2.00 g, 14.5 mmol)and N-phenyl-2,2,2-trifluoroacetimidate chloride (3.40 g, 16.3 mmol) inDCM (70 mL), NaH (60% in mineral oil, 0.635 g, 15.8 mmol) was added portionwise at 0C.The mixture was stirred for 2h at rt. After an addition of ice, the organic phase was washedwith water (3 x 40 mL), dried (MgSO4), filtered, and evaporated. The resulting residue wascrystallized from Et2O/PE, to give 1 as white needles (4.00 g, 89%). mp 90-91C, 1H NMR(360 MHz in CDCl3, ppm): delta 7.37 (2H, br d, J = 8.5 Hz, Ph), 7.29 (2H, br t, J = 2.0 Hz, J =6.5 Hz, J = 7.5 Hz, Ph), 7.08 (1H, br t, J = 1.0 Hz, J = 7.0 Hz, J = 7.5 Hz, Ph), 6.92 (2H, br d,J = 8.5 Hz, Ph-OCH3, PMB), 6.82 (2H, br d, J = 8.5 Hz, Ph-OCH3, PMB), 5.25 (2H, s, CH2,PMB), 3.83 (3H, s, OCH3, PMB), 13C NMR (90 MHz in CDCl3, ppm): delta 160.08 (Cquat-OCH3,PMB), 145.28 (q, JC-C-F = 35,0 Hz), 144.58 (Cquat arom), 130.42, 128.89, 127.23, 124.04,119.73 (CH arom), 116.38 (q, JC-F = 285,5 Hz), 114.13 (Cm PMB), 69.69 (CH2,PMB), 53.32 (OCH3, PMB), HRMS (ESI) m/z [M+Na] 332.0869; found 332.0859, AnalCalcd C16H14F3NO2 : Calcd. C 62.13, H 4.56, N 4.53; found C 62.30, H 4.59, N 4.44.

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

Reference:
Article; Barroca-Aubry, Nadine; Benchekroun, Mohamed; Gomes, Filipe; Bonnaffe, David; Tetrahedron Letters; vol. 54; 37; (2013); p. 5118 – 5121;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H6Cl2

General procedure: In the initial mixed solution prepared in the round flask in Example 1, 3-chloro-2-(chloromethyl)prop-1-ene(50 [mu] L, 0.47 mmol)By following the same procedure as in Example 1 except for using 1-pyrene methanol (240 mg, 1.03 mmol)Experiments were conducted to obtain a solid state of the compound containing pyrene dimer, 120 mg in 49% yieldOctane-1,8-diol (99 mg, 0.68 mmol) (1 eq.)And 1-(bromomethyl)pyrene (440 mg, 1.49 mmol) (2.2 eq.),3 mL ([diol] = 50 mM) in anhydrous dimethylformamide in (DMF)To room temperature in the presence and condition of N2 and NaH (3 eq.), It was added to the round bottom flask. The mixed solution in the flask was stirred at room temperature for 1 hour.After that,Then quenched and diluted with distilled water was added to the solution.next, The organics were extracted by the addition of methyl-dichloro (DCM) to the mixed solution,The resulting organic layer was again distilled under reduced pressure to reotgo so that solution filtered through a filter containing sodium sulfate (Na2SO4).The resultant was purified by silica gel column chromatography (EtOAc: Hexane = 1: 5 (volume ratio)) of the solid state compound containing pyrene dimer increasing the purity of the resultant using,To give the 120 mg at a yield of 31%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1871-57-4.

Reference:
Patent; Inha UniversityIndustry-AcademicCooperation Foundation; Jo, Dong Gyu; (29 pag.)KR101542140; (2015); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 20850-43-5,Some common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, molecular formula is C8H7ClO2, 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.

Under argon atmosphere, 17.5 ml of 1.58M n-butyl lithium-n-hexane solution was dropped into a mixture of 25 ml of tetrahydrofuran and 2.78 g of diisopropylamine under cooling ice, followed by 30 minutes’ stirring under the same condition. Thereafter a solution of 2.50 g of 1-tert-butoxycarbonyl-3-oxopiperazine (which was prepared by following Tetrahedron Lett., 1980, 21, 3019 – 3020) in 60 ml of tetrahydrofuran was added by dropping under cooling with ice, followed by 3 hours’ stirring under the same condition, further dropping of a solution of 2.30 g of 5-chloromethyl-benzo[1,3]dioxole in 20 ml of tetrahydrofuran under cooling with ice, and an hour’s stirring under the same condition. The solution was warmed to room temperature and stirred for 18 hours. After addition of saturated aqueous ammonium chloride solution, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and the solvent was distilled therefrom under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate) to provide 2.84 g (68%) of 2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonyl-3-oxopiperazine. 1H-NMR(CDCl3)delta:6.67(s,1H),6.65(d,J=1.3Hz,2H),5.90(s,2H), 4.52~4.43(m,1H),4.12(d,J=7.2Hz,2H),3.23(t,J=5.1Hz,2H), 2.57(t,J=5.8Hz,2H),1.45(s,9H) Mass,m/e:334(M+),278,144,57(base)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Chloromethyl)benzo[d][1,3]dioxole, its application will become more common.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP1724267; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-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. Recommanded Product: 2-Chloro-4-fluoroanisole

To concentrated sulfuric acid (100mL) solution of2-chloro-4-fluoro anisole (38g, 237mmol), bromine (19mL, 737mmol) was addedunder ice-cooling, and the mixture was stirred for 1.5 hours. the reactionsolution was added gradually into ice water and extracted with diethyl ether(300mL × 3). After washing the organic layer with 5% aqueous sodium thiosulfatesolution (300 mL), the organic layer was dried over anhydrous magnesiumsulfate, filtered, and the crude product obtained through concentration underreduced pressure was purified by silica gel chromatography (hexane: ethylacetate = 1 : 0~10: 1) to give white solid of 5-bromo-2-chloro-4-fluoro anisole(8.0 g, yield: 14%) and white solid of 2-bromo-6-chloro-4- fluoro anisole (16.7g, yield: 30%).

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

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; MATSUKAWA, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (75 pag.)JP2016/56157; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 7149-75-9, A common heterocyclic compound, 7149-75-9, name is 4-Chloro-3-methylaniline, molecular formula is C7H8ClN, 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.

Step 1 (0420) To a mixture of 4-chloro-3-methylphenylamine (350 mg), potassium carbonate (1.09 g) and N,N-dimethylformamide (10 mL) was added trifluoromethanesulfonic acid 2,2,2-trifluoroethyl ester (0.57 mL), and the mixture was stirred at an external temperature of 80° C. for 20 hours. The mixture was cooled to room temperature. After the mixture was diluted with ethyl acetate, and the resulting mixture was washed with water, saturated sodium hydrogen carbonate aqueous solution and brine successively, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: 0percent-10percent ethyl acetate:hexane, gradient elution) to give (4-chloro-3-methylphenyl)-(2,2,2-trifluoroethyl)amine (209 mg). (0421) 1H-NMR (CDCl3) delta ppm: 2.31 (3H, s), 3.65-3.90 (3H, m), 6.46 (1H, dd, J=8.5, 2.8 Hz), 6.55 (1H, d, J=2.8 Hz), 7.15 (1H, d, J=8.5 Hz).

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; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 38762-41-3, 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 38762-41-3 as follows.

f) Compound 1.7; A solution of 4-bromo-2-chloroaniline (4.00 g, 19.37 mmol), bis(pinacolato)diboron (5.90 g, 23.2 mmol) and KOAc (12.3 g, 58.1 mmol) in DMSO (100 mL) was deoxygenated by bubbling nitrogen through it for 45 min. PdCl2 (dppf) g, 1.94 mmol) and dppf (1.07 g, 1.94 mmol) were then added and the mixture was heated at 100C for 4 h. After cooling to room temperature the reaction mixture was diluted with EtOAc, washed successively with water and brine, dried (MgS04), filtered and concentrated under reduced pressure. The crude product was purified twice by flash chromatography using CH2Cl2 to give intermediate 1.7 (2.15 g, 44% yield) as a white solid.

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2005/118575; (2005); A1;,
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. 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

[4-(5-Chloro-6-fluoro-1H-benzoimidazol-2-yl)-phenyl]-methyl-(2-piperidin-1-yl-ethyl)-amine mp 167-168 C.

The synthetic route of 139512-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US6348487; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 918538-05-3,Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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.

Compound 5 (80 mg, 0.424 mmol) was weighed out,P-trifluoromethoxybenzeneboronic acid (90 mg, 0.44 mmol)Triethylamine (121 mg, 1.2 mmol)Bis (triphenylphosphine) palladium (II) chloride (30 mg, 0.042 mmol)DMF (28.5 ml), water (0.5 ml) was added to the flask and heated to 80 C for 4 h.After stopping the reaction, 100 ml of water was added to the reaction solution,Stirred, extracted with ethyl acetate (20 ml * 4)The ester layer was dried over anhydrous sodium sulfate, concentrated,Column chromatography (petroleum ether: ethyl acetate = 20: 1) gave a yellow solid (97 mg, 77.6%).

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-Dichloropyrrolo[2,1-f][1,2,4]triazine, its application will become more common.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Xin Minxing; Wen Jun; Tu Chongxing; Liu Zhaoyu; Shen Han; Wang Mengyu; Zhao Xinge; (36 pag.)CN104003990; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1871-57-4,Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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 stirred suspension of sodium hydride (60% suspension in oil) (1.74 g, 43.5 mmol) in N,N-dimethylformamide (36 mL) at 0 C. was added 2-chloro-2-(chloromethyl)prop-1-ene (1.54 mL, 14.5 mmol). To this was added tert-butyl N-[2-(tert-butoxycarbonylamino)ethyl]carbamate (3.78 g, 14.5 mmol) in THF (36 mL). After 15 minutes the ice-bath was removed and the reaction stirred at room temperature for 18 h. The reaction was quenched by the addition of saturated ammonium chloride (100 mL) and the mixture concentrated to remove the THF. The aqueous was extracted with EtOAc (3×) and the combined organics were dried (MgSO4) and the solvent evaporated to afford a crude solid. This was purified (silica, 0 to 20% EtOAc/i-hexane) to afford the title compound as a white solid (2.24 g, 49%). 1H NMR (300 MHz, CDCl3) 1.45 (18H, s), 3.45 (4H, m), 3.90 (2H, m), 4.0 (2H, m), 4.95 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2-chloromethyl-1-propene, its application will become more common.

Reference:
Patent; BicycleTx Limited; Beswick, Paul; Mudd, Gemma Elizabeth; McDonnell, Kevin; Ivanova-Berndt, Gabriela; Van Rietschoten, Katerine; Witty, David; Skynner, Michael; US2020/131228; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

53145-38-3, name is 2-Chloro-6-fluoroanisole, belongs to chlorides-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. COA of Formula: C7H6ClFO

4. Preparation of 4-chloro-2-fluoro-3-methoxybenzoic acid To a magnetically stirred solution of 2-chloro-6-fluoroanisole (16.06 g) in 100 mL of anhydrous DME, cooled to -70 C., was added 44 mL of 2.5 M n-BuLi in hexanes over 30 min, while keeping the reaction temperature below -55 C. After stirring the reaction for an additional 60 min at -70 C., dry carbon dioxide was bubbled into the reaction mixture for 60 min, while keeping the temperature below -60 C. Upon warming to room temperature, the reaction mixture was added to 150 mL of ether and acidified with 37% aq. HCl. The aqueous layer was washed with 2*150 mL of ether, and the combined organic layers were washed with sat. NaCl and were dried (Mg2SO4). Solvent removal gave 20.3 g of a white solid, which was recrystallized from ether/hexane to give 16.4 g (80% yield) of 4-chloro-2-fluoro-3-methoxybenzoic acid; MP 183-184 C.; 1H NMR (d6-DMSO, 300 MHz) delta 13.5 (brs, 1H), 7.60 (dd, 1H, J=1.8, 8.8 Hz), 7.42 (dd, 1H, J=1.8, 8.8 Hz), 3.95 (s, 3H).

The synthetic route of 53145-38-3 has been constantly updated, and we look forward to future research findings.

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