Month: March 2021

Reference of 623-12-1,Some common heterocyclic compound, 623-12-1, name is 1-Chloro-4-methoxybenzene, molecular formula is C7H7ClO, 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.

General procedure: (If aryl chloride is liquid) under N2 atmosphere, arylboronic acid 3 (0.6 mmol), 1a (1.0 mol%), K3PO4¡¤3H2O (2.0 equiv), H2O (2.0 mL), and THF (1.0 mL) were added into a Schlenk reaction tube, then aryl chloride 2 (0.5 mmol) was added. The mixture was stirred at room temperature for 24 h. Then the mixture was extracted with EtOAc, dried over anhydrous Na2SO4, filtered and purified by flash column chromatography to give the pure products.Comment(If aryl chloride is solid) under N2 atmosphere, aryl chloride 2 (0.5 mmol), arylboronic acid 3 (0.6 mmol), 1a (1.0 mol%), K3PO4¡¤3H2O (2.0 equiv), H2O (2.0 mL), and THF (1.0 mL) were added into a Schlenk reaction tube. The mixture was stirred at room temperature for 24 h. Then the mixture was extracted with EtOAc, dried over anhydrous Na2SO4, filtered and purified by flash column chromatography to give the pure products.

The synthetic route of 623-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tang, Yi-Qiang; Lu, Jian-Mei; Shao, Li-Xiong; Journal of Organometallic Chemistry; vol. 696; 23; (2011); p. 3741 – 3744;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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. Safety of 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline

2,4-dichloro-5,6,7,8-tetrahydroquinazoline (0.5 g, 2.46 mmol) was added to a round bottom flask and dissolved in tetrahydrofuran (30 mL), and furfurylamine (0.23 mL, 2.46 mmol) and triethylamine (1.03 mL, 7.39 mmol) were added thereto, followed by stirring at 60 C. for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and water was added to the reaction mixture. The resulting mixture was extracted with dichloromethane and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane, 1:1, v/v) to obtain a compound (0.22 g, 34%); 1H NMR (400 MHz, CDCl3) delta 1.82 (s, 4H), 2.28 (s, 2H), 2.68 (s, 2H), 4.68 (d, J=4.8 Hz, 2H), 4.99 (s, 1H), 6.32 (d, J=12.4 Hz, 2H), 7.37 (s, 1H); 13C NMR (400 MHz, CDCl3) delta 21.82, 21.86, 21.91, 31.63, 38.20, 108.01, 110.53, 110.55, 142.37, 151.08, 157.37, 161.42, 164.43.

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; LEE, So Ha; YOO, Kyung Ho; ROH, Eun Joo; SIM, Tae Bo; KIM, Tae Young; KIM, Jae Ho; (30 pag.)US2019/315726; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 821-10-3, A common heterocyclic compound, 821-10-3, name is 1,4-Dichlorobut-2-yne, molecular formula is C4H4Cl2, 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.

General procedure: K2CO3 (3a, 210 mg, 1.5 mmol) was added to a solution of b-ketosulfones 1a-p (0.5 mmol) in acetone (10 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. 1,4-Dichloro-2-butyne (2, 68 mg, 0.55 mmol) was added to the reaction mixture at 25 C. The reaction mixture was stirred at 56 C for 8 h. The reaction mixture was cooled to 25 C and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (320 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc15/1e8/1) afforded 4a-p.

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; Chan, Chieh-Kai; Lu, Yi-Ju; Chang, Meng-Yang; Tetrahedron; vol. 71; 51; (2015); p. 9544 – 9549;,
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. 329944-72-1, name is 3-Bromo-5-chlorotoluene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Bromo-5-chlorotoluene

S-Chloro-S-metbyl-benzonitrile To a stirred soiution of 1-Bromo-3-chloro-5-methyl- benzene (7 32g, 35 62mmol) in DMF (70ml), were added zinc cyanide (2.51g, 21 37mmol), DPPF (395mg, 0 712mmol), and Pd2dba3 (326mg, 0.356mmol) in this order. The flask was flushed with nitrogen and stirred in an oil bath (110-1200C) for 5hr After cooling to room temperature, the mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, etherhexane (from 1 ’19 to 1 9)) to afford 2.8g (51%) of a paie yellow solid m.p. 74-76 0C, 1H-NMR(200MHz, CDCi3) delta 2 39(3H s), 7 35(1 H, s), 7.40(1 HT s), 7.44(1 H, s), m/z (El) 151(M+).

According to the analysis of related databases, 329944-72-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KIM, Choung, U.; MITCHELL, Michael, L.; SON, Jong, Chan; WO2010/9047; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-50-3, These common heterocyclic compound, 1435-50-3, name is 2-Bromo-1,4-dichlorobenzene, 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.

General procedure: To a flask containing Mg turnings (0.29 g, 12 mmol) was added1-bromo-4-methylbenzene (1.37 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL,12 mmol) was added to the reaction mixture. The obtained mixturewas stirred for 2 h at 0 C. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After beingstirred for 2 h at room temperature, the reaction mixture waspoured into satd aq Na2SO3 solution and was extracted with CHCl3 (3*30 mL). The organic layer was dried over Na2SO4 and filtered.After removal of the solvent, the residue was purified by shortcolumn chromatography on silica gel (eluent: hexane/ethylacetate=9:1, v/v) to provide pure 4-methyl-1-benzonitrile (0.77 g) in 82% yield.

The synthetic route of 1435-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; 5; (2013); p. 1462 – 1469;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 39226-96-5, 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 39226-96-5 as follows.

Example 76 /V-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2- pyrazinyl)-4-imidazolidinecarboxamide (E76) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); To a solution of 3-methyl-2-oxo-1-(2-pyrazinyl)-4-imidazolidinecarboxylic acid (145 mg, 0.561 mmol) and N-ethylmorpholine (0.426 ml, 3.36 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (86 mg, 0.561 mmol) and 1-ethyl-3- (3-dimethylaminopropyl)carbodiimide hydrochloride (107 mg, 0.561 mmol) and the reaction mixture was stirred for 10 minutes at room temperature. 1-[2-Chloro-3- (trifluoromethyl)phenyl]methanamine (141 mg, 0.673 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine and separated by hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by SP4 automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give N- {[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2-pyrazinyl)-4- imidazolidinecarboxamide (45 mg, 19 % yield). LC/MS [M+H]+ = 413, retention time = 2.21 minutes.

According to the analysis of related databases, 39226-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
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. 626-43-7, name is 3,5-Dichloroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 626-43-7

General procedure: Compound 12a, 12b or 12c (0.55 mmol), the appropriate amine(1.1 mmol) and 1,2-dimethoxyethane (1 mL) were heated in amicrowave reactor (150 Watt, Power Max On, 90 C, 10 bar) for1 h. The solvent was removed under reduced pressure and the residuewas purified by column chromatography (silica gel, ethylacetate).

According to the analysis of related databases, 626-43-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koch, Pierre; Akkari, Rhalid; Brunschweiger, Andreas; Borrmann, Thomas; Schlenk, Miriam; Kueppers, Petra; Koese, Meryem; Radjainia, Hamid; Hockemeyer, Joerg; Drabczy?ska, Anna; Kie?-Kononowicz, Katarzyna; Mueller, Christa E.; Bioorganic and Medicinal Chemistry; vol. 21; 23; (2013); p. 7435 – 7452;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 870-24-6,Some common heterocyclic compound, 870-24-6, name is 2-Chloroethanamine hydrochloride, molecular formula is C2H7Cl2N, 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 I: 2-(2-Methyl-1H-pyrrol-1-yl)ethanamine Sodium hydroxide anhydrous (9.87 g, 0.246 mol, 4.0 eq.) and TBAHS (0.838 g, 0.002 mol, 0.04 eq.) were added to a solution of 2-methyl-1H-pyrrole (5.0 g, 0.061 mol, 1.0 eq.) in acetonitrile (180 ml) at 0 C. and the mixture was stirred at RT for 1 h. 2-Chloroethylamine hydrochloride (8.59 g, 0.074 mol, 1.2 eq.) was added to the reaction mixture and it was then heated at reflux for 16 h. The reaction mixture was cooled to RT, filtered through celite and washed with 10% MeOH/DCM (200 ml). The filtrate was concentrated under reduced pressure to give the crude product which was used in the next step without further purification. Yield: 100%, crude (7.6 g, 0.061 mol)

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

Reference:
Patent; Gruenenthal GmbH; US2012/58999; (2012); 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. 38762-41-3, name is 4-Bromo-2-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 38762-41-3

To a solution of ?-MeO-9-BBN (1.0M in hexane, 22 mol) in THF (20 mL) at O0C was added n-propylmagnesium bromide (2.0M in ether, 10.5 mL). After 10 min, solvent was evaporated, and to the residue was added NMP (60 mL), Pd(dppf)Cl2 (1.0 mmol), 4-bromo-2-chloroaniline (20 mmol) and aqueous sodium carbonate (1.0M, 30 mL). The reaction was then heated at 95 0C overnight. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (20×3 mL) and saturated brine (20 mL). The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure. Flash chromatography of the residue (silica gel, slow gradient of 0-100% DCM in hexane) afforded 10.1. MS-ESI (pos.) m/z: 170 (M+H).

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2008/137027; (2008); A2;,
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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C2Cl2N4

Example 1 General Phase-Transfer Protocol for Tetrazine Insertion A 50 mL glass vial, was charged with unprotected peptide 1 (20 mumol) then sealed with a septum and purged with argon. Next, a degassed solution of 50 mM (pH ?5) monosodium phosphate (20 mL) was added followed by a solution of dichlorotetrazine (9.1 mg, 60 mumol, 3 equiv) in CHCl3 (20 mL). The two-phases were mixed vigorously on a vortex for 1 minute. The mixture was divided between three 20 mL Falcon tubes then transferred to a benchtop centrifuge and further separated at 2500 RPM for 1 minute. The aqueous phase, now orange in color, was collected and each organic layer was extracted with an additional portion of water (5 mL) then transferred to a benchtop centrifuge and separated again at 2500 RPM for 1 minute. All of the aqueous fractions were combined and lyophilized. The crude mixture was then purified by reverse-phase high-pressure liquid chromatography (HPLC) to yield an orange powder after lyophilization. A 50 mL glass vial, was charged with unprotected peptide 1a (11.4 mg, 20 mumol) then sealed with a septum and purged with argon. Next, a degassed solution of 50 mM (pH 5) monosodium phosphate (20 mL) was added followed by a solution of dichlorotetrazine (9.1 mg, 60 mumol, 3 equiv) in CHCl3 (20 mL). The two-phases were mixed vigorously on a vortex for 1 minute. The mixture was divided between three 20 mL Falcon tubes then transferred to a benchtop centrifuge and further separated at 2500 RPM for 1 minute. The aqueous phase, now orange in color, was collected and each organic layer was extracted with an additional portion of water (5 mL) then transferred to a benchtop centrifuge and separated again at 2500 RPM for 1 minute. All of the aqueous fractions were combined and lyophilized. The crude mixture was then purified by reverse-phase high-pressure liquid chromatography (HPLC) (gradient 5-15% organic over 5 min) to yield 10.1 mg of 2a (78%) an orange powder after lyophilization. 1H NMR (500 MHz, D2O) delta ppm 1.36 (quin, J=7.80 Hz, 2H) 1.58-1.66 (m, 3H) 1.68 (q, J=7.90 Hz, 2H) 1.79 (ddd, J=13.90, 8.30, 5.50 Hz, 1H) 1.78 (ddd, J=13.25, 8.10, 5.30 Hz, 1H) 2.07 (q, J=7.34 Hz, 2H) 2.39 (dd, J=7.30, 5.10 Hz, 1H) 2.39 (dd, J=9.80, 7.40 Hz, 1H) 2.93 (t, J=7.48 Hz, 9H) 3.50 (dd, J=15.60, 4.06 Hz, 3H) 3.54 (dd, J=18.20, 6.20 Hz, 1H) 3.57 (dd, J=11.30, 7.70 Hz, 1H) 4.10 (t, J=6.52 Hz, 1H) 4.14 (dd, J=8.44, 5.24 Hz, 1H) 4.20 (dd, J=7.10, 6.40 Hz, 1H) 4.53 (dd, J=15.39, 2.99 Hz, 1H) 4.56 (dd, J=15.60, 4.92 Hz, 1H) 4.80 (t, J=3.42 Hz, 1H) 4.99 (dd, J=4.90, 1.90 Hz, 1H). 13C NMR (126 MHz, D2O) delta 178.6, 178.1, 171.7, 170.6, 170.5, 169.9, 169.1, 169.1, 61.8, 55.0, 53.9, 52.4, 52.3, 51.5, 39.1, 31.4, 31.1, 30.7, 30.2, 26.7, 26.2, 22.1. HRMS (ES) found m/z 647.2026 [(M+H)+. calcd for C22H35N10O9S2: 647.2024].

According to the analysis of related databases, 106131-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Trustees Of The University Of Pennsylvania; Smith, III, Amos B.; Brown, Stephen; (18 pag.)US2015/376579; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics