Author: Jessica.F

Synthetic Route of 29242-84-0, 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. 29242-84-0, name is 2-Chloro-4-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 4 N2-(2-chloro-4-methoxyphenyl)-N4,N4-dipropyl-5,7-dihydrofura[3,4-d]pyrimidine-2,4-diamine: [Show Image] A mixture of the compound prepared in Example 3 (300 mg) and 2-chloro-4-methoxyaniline (554 mg) was reacted for 60 minutes by microwave (90 watt, 120C). The reaction mixture was cooled to room temperature, and poured into a mixed solution of ethyl acetate / a saturated aqueous solution sodium bicarbonate and then the mixture was extracted by ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (toluene : ethyl acetate = 20 :1 ? hexane : ethyl acetate = 8 : 1 ? 6 : 1) to give the title compound (385 mg) as a pale yellow powder having the following physical data. TLC: Rf 0.29 (hexane : ethyl acetate = 4 : 1); 1H-NMR (300MHz, CDCl3): delta 0.93, 1.59, 3.30, 3.79, 4.82, 5.18, 6.81, 6.94, 7.03, 8.28.

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-Chloro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1666468; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, 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 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine

8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (200 mg, 0.82 mmol) was combined with triethylborane (1M in THF, 2 mL, 2 mmol), K2C03 (283 mg, 2.05 mmol) and Pd(PPh3)4 (92 mg, 0.08 mmol ) in DMF (3 mL). The reaction vessel was degassed and then charged with nitrogen three times. The mixture was stirred at 100 C for 5 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0- 35% EtOAc in petroleum ether to yield 6-chloro-8-ethyl-2-methylimidazo[l,2-b]pyridazine (80 mg, 50%). MS m/z 196.0, 198.0 [M+H]+.

The synthetic route of 1298031-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 450-89-5, 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. 450-89-5 name is 2-Chloro-5-fluoroanisole, 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.

To a solution of 1-chloro-4-fluoro-2-methoxy-benzene (12.9 g, 80 mmol) in 1,2- dichloroethane (80 mL) at room temperature, CHLOROACETYL chloride (7.7 mL, 96 MMOL) and aluminium trichloride (21.4 g, 0.16 MMOL) were added. The solution was heated to 70C and stirred at this temperature for 3h under nitrogen. After cooling to room temperature, the reaction mixture was carefully poured onto crushed ice and extracted with DCM (2 x 150 mL). Washing of the organic layers with brine (200 mL) followed by drying (NA2SO4) and removal of the solvent in vacuo afforded a crude which was purified by flash chromatography eluting with 20% cyclohexane in ethyl acetate. The oil collected (8 g) was a mixture containing the title compound together with 2-CHLORO-4-(2-CHLORO-ACETYL)-5-FLUORO-PHENYL CHLOROACETATE. The mixture (7.8 g) was dissolved in methanol (100 mL) and a 2M aqueous solution of sodium carbonate (45 mL) was added. The solution was stirred at room temperature for 1H then the organic solvent was removed under vacuum and the remaining solution was acidified with a 5% aqueous solution of HCI, extracted with DCM (120 mL), washed with brine (80 mL) and dried (NA2SO4). Removal of the solvent in vacuo afforded the title compound (D37) as a brown solid (6.8 g, 38%). MS; (EI) M/Z : 222 [M] +. C8H5CI2FO2 requires 222. ‘H-NMR (500 MHz, DMSO-D6) 8 : 11.8 (bs, 1H), 7.87 (d, 1H), 6.83 (d, 1H), 4.94 (d, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-fluoroanisole, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/46124; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 60811-17-8, name is 5-Bromo-2-chloroaniline, 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 60811-17-8, Quality Control of 5-Bromo-2-chloroaniline

Step 1: N-(5-Bromo-2-chloro-phenyl)-benzenesulfonamide; To a stirring solution of 5-Bromo-2-chloroaniline (100 mg, 0.48 mmol) in DCM (5 ml) is added benzenesulfonyl chloride (280 mg, 202 ul, 1.58 mmol) and pyridine (195 ul, 2.42 mmol). The reaction mixture is stirred at room temperature for 18 hours. EtOAc (20 ml) is added and the reaction mixture is washed with 0.1m HCl (20 ml), the phases are separated and the organic portion is washed with water (3x), dried over MgStheta4, concentrated in vacuo and dried in a vacuum oven to afford the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-chloroaniline, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2009/13348; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 4261-67-0, 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 4261-67-0 as follows.

EXAMPLE 10 A mixture of 1-chloro-3-(dimethylamino)-2-methylpropane hydrochloride (200 g), thiourea (97.3 g) and ethanol (950 ml) was stirred and heated under reflux for 72 hours. The solution was allowed to cool and the solvent was removed in vacuo. The residue was dissolved in a small volume of ethanol and ether was added until the first permanent opalescence was observed. The mixture was stored at 4° C. for 16 hours. The solvent was removed in yacuo to afford a waxy/oily solid which was dried in vacuo over calcium chloride for 48 hours, then triturated with propan-2-ol. The resulting solid was collected by filtration, washed with propan-2-ol, and dried in vacuo to give S-[3-(dimethylamino)-2-methylpropyl]isothiourea dihydrochloride as a pale brown solid (90 g).

According to the analysis of related databases, 4261-67-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Knoll Aktiengesellschaft; US5652271; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 179897-90-6, A common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

DMF (dimethylformaldehyde)To a solution of 1,3-dibromo-2-chloro-5-fluorobenzene (23.0 g, 79.8 mmol)And di-tert-butylphenylamine (24.3 g, 144 mmol)And cesium carbonate (84.4 g, 239 mmol) were charged, and the mixture was heated to 140 C and reacted for 40 hours.After cooling to room temperature, the mixture was extracted with EA, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.This was subjected to column chromatography with EA: Hx to obtain 12.0 g (Yield = 34%) of [Intermediate 12-1].

The synthetic route of 179897-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Yoon Jeong-min; Kim Gong-gyeom; Huh Nan-seul-a; Lee Gi-gon; Keum Su-jeong; (52 pag.)KR2018/112721; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 54730-35-7, These common heterocyclic compound, 54730-35-7, name is 3,5-Dichloro-4-methylaniline, 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.

Preparation 2; 5-bromo- 1 ,3-dichloro-2-methylbenzene; Suspend the 3,5-dichloro-4-methylaniline in 48% HBr (5 mL) and water (5 mL) and heat with a heat gun until the mixture is near the boiling point. Cool the slurry to room temperature and then cool to 00C with an ice/brine bath. Add a solution of sodium nitrite (109 mg, 1.58 mmol) in water (2 mL) dropwise. After the addition is complete, stir the reaction an additional 15 min in the cold bath. Add a solution of CuBr (1.08 g, 7.53 mmol) in 48% HBr (2 mL) and heat the rapidly stirring reaction to 500C for 1 hour. Cool the reaction to room temperature, dilute the reaction with ethyl acetate and discard the aqueous layer. Wash the organic layer with water and brine, dry with MgSO4, filter through celite and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 164 mg (45%) of the product as a yellow solid.

Statistics shows that 3,5-Dichloro-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 54730-35-7.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/127763; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 179897-90-6, 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. 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 1. Preparation of 3-bromo-2-chloro-5-fluoroaniline To a sealable glass tube was charged 1,3-dibromo-2-chloro-5-fluorobenzene (12.52 g, 43.4 mmol), benzophenone imine (8.26 g, 45.6 mmol), sodium tert-butoxide (6.26 g, 65.1 mmol), and toluene (100 mL). The resulting mixture was thoroughly sparged with Argon, followed by the addition of Pd2(dba)3 (0.398 g, 0.434 mmol) and (S)-BINAP (0.81 g, 1.3 mmol), and follow by another Argon sparge. The reaction tube was sealed and heated to 85 C. in an oil bath and maintained overnight. The reaction was allowed to cool to room temperature and quenched with water (20 mL). The resulting layers were partitioned and separated. The organic phase was concentrated and assayed to be a mixture of mono- and bis-aminated products (~4:1 by HPLC area at 220 nm). The residue was dissolved in THF (70 mL), treated with aqueous 3.0 M HCl (20 mL) at room temperature for 1 hour and basified with saturated aqueous Na2CO3 solution (40 mL). The reaction mixture was allowed to partition and the layers were separated. The organic portion was separated, washed with brine, concentrated and the resulting residue was purified by flash chromatography (SiO2, 0-15% EtOAc in heptane) and 3-bromo-2-chloro-5-fluoroaniline was obtained as a light yellow solid (6.82 g, 30.4 mmol): LCMS(m/z): not ionized (MH+), tR=0.95 minute; 1H NMR (CDCl3, 300 MHz) delta 4.32 (br s, 2H), 6.44 (dd, J=9.8, 2.8 Hz, 1H), 6.77 (dd, J=7.9, 2.6 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2-chloro-5-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Costales, Abran Q.; Huang, Shenlin; Jin, Jeff (Xianming); Liu, Zuosheng; Pecchi, Sabina; Poon, Daniel; Tellew, John; US2011/52578; (2011); A1;,
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. 2162-98-3, name is 1,10-Dichlorodecane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,10-Dichlorodecane

Reaction product of N,N-dimethylaminoethanol and 1 ,10-dichlorodecane (AE- DCD) [0089] N,N-dimethylaminoethanol (4.216 g, 0.047 mol) was added to a single neck round bottom flask. The flask was then fitted with a drying tube and stirred using a magnetic stirrer. 1,10-dichlorodecane (5 mL, 0.024 mol) was added slowly through a syringe to control the exothermic mixing. After completing the addition the reaction mixture was stirred under ambient conditions for 30 minutes. It was then immersed in a preheated oil bath maintained at 80 C. The contents of the flask solidified after heating for 4 h. The solid was washed with diethyl ether and dried in a vacuum oven. Yield: 6 g. 1H-NMR analysis indicated that the -CH3 group attached to the N atom shifted to 3.3 ppm after quaternization.

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 2162-98-3.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; ANBANANDAM, Parthiban; (53 pag.)WO2016/148649; (2016); 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. 18112-31-7, name is 3-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

To a solution of 3-bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine (865 mg, 5.16 mmol, 1.0 equiv) in acetonitrile (15 mL) was added boronic acid (5.16 mmol, 1.0 equiv), bis(triphenylphosphine)palladium(II)dichloride (0.516 mmol, 0.1 equiv), then sodium carbonate (1.0 M aqueous solution, 10 equiv). The reaction mixture was irradiated in the microwave at 150 C. for 10 min. Purification by column chromatography gave of the product.

The synthetic route of 18112-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Califia Bio, Inc.; GOODFELLOW, VAL S.; NGUYEN, THONG X.; RAVULA, SATHEESH B.; GELBARD, HARRIS A.; US2014/256733; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics