Month: June 2021

Synthetic Route of 7006-52-2,Some common heterocyclic compound, 7006-52-2, name is N-Methyl-3-chloroaniline, molecular formula is C7H8ClN, 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: Ureas used in this project were prepared according to reaction equation (1)-(3) and related procedures given below. A 100 mL two-necked flask with a magnetic stir bar was evacuated and backfilled with argon three times. Amine (2 eq) was dissolved in THF. A solution of n-BuLi (2.5 M in hexane, 1.0 eq) was added slowly at ?40 °C and the resulting mixture was stirred for 15 min at the same temperature. After cooling to ?60 °C, iodomethane (1.0 eq) was added slowly and the mixture was allowed to warm to rt and stirred for additional 8 h at rt. The mixture was quenched by adding H2O and the organic phase was separated. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with sat. NaHCO3-solution, dried over Na2SO4 and the solvents were evaporated under reduced pressure. After purification by flash chromatography the pure product was obtained. A 100 mL two-necked flask with a magnetic stir bar was evacuated and backfilled with argon three times. Triphosgene (5.0 mmol) and CH2Cl2 (30 mL) were added to the flask. The mixture was cooled at ?30 °C and dry pyridine (3.0 mL) was slowly added to the flask (Caution: highly toxic phosgene was generated). After stirring for 15 min at ?30 °C, secondary amine (10 mmol) was slowly added to the mixture. The mixture was warmed to room temperature and stirred for 6 h at room temperature. The reaction mixture was carefully quenched by 1N HCl (10 mL) and was extracted with CH2Cl2 (5 mL x 3). The organic layer was washed with water and brine, then dried over Na2SO4. After the filtration, the solution was concentrated to dryness. The crude product was purified by silica gel column chromatography. Further purification was carried out by recrystallization or distillation under vacuum. MeNH2 methanol solution (33.3percent) (1.5 equiv.), acid chloride (1.0 equiv.), Et3N (2.0 equiv.) and CH2Cl2 (0.5 M) were added into a round bottom flask capped with a septum. The mixture was stirred at room temperature. After 2 h, the crude reaction mixture was extracted with CH2Cl2, purified by flash chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-Methyl-3-chloroaniline, its application will become more common.

Reference:
Article; Wang, Yan; Zhou, Hao; Xu, Ke; Shen, Mei-Hua; Xu, Hua-Dong; Chinese Chemical Letters; vol. 28; 1; (2017); p. 92 – 96;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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. SDS of cas: 14752-66-0

General procedure: A sealable reaction tube equipped with a magnetic stirrer bar was charged with azaarenes (1.0 mmol), sodium benzenesulfinate (2 equiv), TBAI (0.2 equiv), tert-butyl peroxybenzoate (TBPB, 1 equiv), and water (1 ml). The reaction was carried out at 100 C. After completion, the result was diluted with diethyl ether, washed with water and brine, and dried with Mg2SO4. After solvent removal under reduced pressure, the residue was purified by column chromatography on silica gel to afford the corresponding product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14752-66-0, its application will become more common.

Reference:
Article; Dong, Dao-Qing; Gao, Xing; Li, Li-Xia; Hao, Shuang-Hong; Wang, Zu-Li; Research on Chemical Intermediates; vol. 44; 12; (2018); p. 7557 – 7567;,
Chloride – Wikipedia,
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Related Products of 626-43-7, 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.

To a stirred solution of bromo acetyl bromide (3.3 g, 16.41 mmol) in CH2C12 (15 mL) was added 3, 5-dichloroaniline 1 (2.65 g, 16.41 mmol) in CH2C12 (10 mL) for 10 mm at RT and stirred for 30 mm. The reaction progress was monitored by TLC; after reaction completion, the volatile reagents and solvent were removed under reduced pressure. The residue was diluted with water (40 mL) and extracted with CH2C12 (2 x 40 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain compound 2 (3.8 g, 65%) as an off-white solid. 1H NMR (500 MHz, CDC13): oe 8.13 (br s, 1H), 7.51 (s, 2H), 7.16 (s, 1H), 4.01 (s, 2H).

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

Reference:
Patent; PHARMAKEA, INC.; HUTCHINSON, John, Howard; LONERGAN, David; HUANG, Fei; ROWBOTTOM, Martin; CALDERON, Imelda; WO2015/48301; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 29027-20-1, name is 3-Chloro-5-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. Quality Control of 3-Chloro-5-methylaniline

Triphosgene (17.01 g, 0.0573 mol) was dissolved in 200 ml of tolunen in a 1 liter flask. 150 ml of a toluene solution of 3-chloro-5-methylaniline (21.9 g, 0.155 mol) and triethylamine (36.0 ml) was added dropwise thereto over 30 minutes at room temperature. The reaction mixture was then stirred at 70&deg C. for 2 hours and cooled to room temperature. The obtained precipitates of hydrochloric acid salt of triethylamine were filtered out and the filtrate liquid was concentrated and treated with distillation at a reduced pressure to obtain 16.87 g of a colorless liquid (production yield 65%). B.p.: 72-74&deg C./0.53-0.66 kPa (4-5 torr) 1H-NMR, 500 MHz, in CDCl3 (delta) 7.00 (bs, 1H), 6.90 (bs, 1H), 6.80 (bs, 1H), 2.31 (s, 3H)

The synthetic route of 3-Chloro-5-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ichida, Akito; US2004/147776; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 174913-12-3, 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. 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-bromo-3-chloro-5-methoxybenzene benzene (835 mg, 3.77 mmol), and i,3,5-trichloro-i,3,5- triazinane-2,4,6-trione (299 mg, 1.29 mmol) in DMF (18 mL) was stirred 16 h under N2 and 50 C. Afier cooling to RT, the reaction mixture was diluted with aqueous NH4C1 and extracted with Et20. The combined organic phases were dried over Mg504, filtered, concentrated, and the resultingresidue was purified by silica chromatography (0 to 25% gradient of EtOAc/heptane) to 1 -bromo-2,3-dichioro-5- methoxybenzene (720 mg, 2.81 mmol). ?H NMR (400 MHz, CHLOROFORM-d) oe ppm 7.14 (d, J=2.76 Hz, 1H), 7.01 (d, J=3.01 Hz, 1H), 3.81 (s, 3H).

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, 1-Bromo-3-chloro-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; Chen, Zhuoliang; Dore, Michael; Fortanet, Jorge Garcia; Karki, Rajesh; Kato, Mitsunori; LaMarche, Matthew J.; Perez, Lawrence Blas; Williams, Sarah; Sendzik, Martin; (63 pag.)US2017/1975; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2268-05-5, name is 2,6-Dichlorofluorobenzene, 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. Computed Properties of C6H3Cl2F

To a solution of 19 (3.0 g, 14.0 mmol) in NMP (20 mL) was added K2CO3 (5.80 g, 41.9 mmol) and 1,3-dichloro-2-fluoro-benzene (26, 2.31 g, 14.0 mmol). The reaction was heated to 120 C. overnight. The reaction mixture was cooled to RT, diluted with H2O and extracted 3 times with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), filtered and evaporated in vacuo to afford 27 which was used in subsequent steps without further purifications.

The synthetic route of 2,6-Dichlorofluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2007/88053; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 62356-27-8, 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. 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 35; STEP A; A reaction mixture of 1-bromo-3-chloro-2-methylbenzene (1.03 g, 5 mmol), methyl but-2-enoate (583 mul_, 5.5 mmol), Pd2(DBA)3 (137.4 mg, 0.15 mmol), tri-f-butylphosphonium tetrafluoroborate (87 mg, 0.3 mmol) and N, N- dicyclohexylmethylamine (1.27 ml_, 6 mmol) in dioxane (5 ml_) was stirred at room temperature under an atmosphere of argon for overnight. Some precipitates formed. The reaction mixture was filtered, and concentrated. Column chromatography with an eluent of 10% EtOAc in Hexane gave compound 35-1 as yellow oil.

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, 1-Bromo-3-chloro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; SHIPPS, JR., Gerald, W.; CHENG, Cliff, C.; HUANG, Xiaohua; ACHAB, Abdelghani, Abe; ORTH, Peter; VOIGT, Johannes, H.; SOUCY, Kyle, Ann; WO2010/56631; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 64628-73-5, 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. 64628-73-5 name is 3-Chloro-4-(trifluoromethoxy)aniline, 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.

Example 35: (5-Chloro-2-f(E)-3-f3-(4-fluoro-benzvl)-3,8-diaza-bicvdoo3.2.11oct-8-yll-3-oxo- propenvll-4-trifluoromethoxv-phenyl)-urea; a) 2-Bromo-5-chloro-4-trifluoromethoxy-phenylamine; N-Bromosuccinimid (7.9 g; 44.5 mmol) in CH2CI2 (500 ml) is added under stirring within 5 min. to a solution of 3-chloro-4-trifluoromethoxy-phenylamine (9.4 g; 44.5 mmol) in CH2CI2 (100 ml) at room temp. After 20 min. the reaction mixture is concentrated to a volume of -150 ml, and hexanes (1000 ml) added to the precipitated crystals. The crystals are filtered off an purified via chromatography (Si02; TBME/hexanes 1/9 to 2/8) to deliver the target compound as yellowish crystals (8.4 g; 42 %). 1 H-NMR (400MHz; DMSO-d6), 8 (ppm) : 5.81 (s, 1 H); 6.94 (s, 1 H); 7.55 (s, 2H). MS (m/z) ES-: 290 (MH-).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/103054; (2005); A2;,
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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, A new synthetic method of this compound is introduced below., Safety of 3,6-Dichloro-1,2,4,5-tetrazine

Dichloro-s-tetrazine (1.50 g,10 mmol) and allyl alcohol (0.68 mL, 10 mmol) were dissolved in 100mL of anhydrous dichloromethane. 2,4,6-collidine (1.32 mL, 10 mmol) was added dropwise at room temperature in the solution, and the mixture was stirred for 1 h 30 min under N2 atmosphere. The solvent was evaporated andthe residue was passed through a column of silica (2/8 dichloromethane/petroleum ether v/v) to give 1.42 g (82%) of compound 1. 1H NMR (CDCl3) delta (ppm) 6.13 (m, 1H, CH), 5.57 (d, 1H, 3J 17.4 Hz, CH=CH2), 5.44 (d, 1H, 3J 10.5 Hz, CH=CH2), 5.18 (d, 2H, CH2, 3J 6.0 Hz). 13C NMR (CDCl3) delta (ppm) 166.6 (CTz-Cl), 164.6 (CTz-O), 130.3 (CH=CH2), 121.1 (CH=CH2), 71.0 (O-CH2).

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; Ben Chaabane, Radhia; Guermazi, Refka; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Dyes and Pigments; vol. 108; (2014); p. 64 – 69;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 175205-77-3, 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. 175205-77-3, name is 4-Chloro-2-(trifluoromethoxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of sodium hydride (804 mg, 33.50 mmol) in DMF (30 mL) under argon atmosphere were added and 2, 4-dichloro-5-methoxypyrimidine (3 g, 16.76 mmol) and 4-fluoro-2-(trifluoromethoxy) aniline (3.2 g, 16.76 mmol) at 0 C. The reaction mixture was warmed to RT and stirred for 6 h. After consumption of the starting material (monitored by TLC), the reaction was diluted with ice water (50 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 10% EtOAc :hexanes to afford 2-chloro-N-(4-fluoro-2-(trifluoromethoxy) phenyl)-5 – methoxypyrimidin-4-amine (2.5 g, 38%) as an off-white solid. ?H-NMR (DMSO-d6, 500 MHz): oe 9.20 (s, 1H), 7.93 (s, 1H), 7.59 (t, 1H), 7.44 (d, 1H), 7.30 (t, 1H), 3.93 (s, 3H); LCMS: 337.8 (M+1); (column; X-Select CSH C-18 (50 x 3.0 mm, 3.5 jim); RT 3.88 mm 0.05% Aq TFA: ACN; 0.80 mL/min); UPLC (purity): 99.5%; (column; Acquity UPLC BEH C-18 2.1 X 50 mm, 1.7 jim); RT 2.59 mi ACN: 0.025% Aq TFA; 0.5 mL/min; TLC: 30% EtOAc/hexane (Rf 0.3).

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

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66696; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics