Month: July 2021

Reference of 202197-26-0, 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 202197-26-0 as follows.

Compound 12 (1.6 g, 6.28 mmol), commercially available 3-chloro-4-(3-fluorobenzyloxy)aniline 13 (1.6 g, 6.3 mmol) and CH3SO3H (20 muL, 5 mol %) were added into anhydrous EtOH (40 mL) and the reaction mixture was heated at 70 C for 2 h. After cooled down, the alcohol solution was diluted with water (150 mL) and the resulting solid was filtered, washed with water and dried to give N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-5-iodo-6-methylpyrimidin-4-amine 14 (2.77 g, 94%) as a white solid. MS-ESI (m/z): 467.8(M-H), 470.0(M+H); 1H NMR (CDCl3, delta): 2.65(s, 3H), 5.15(s, 2H), 6.94(d, 1H), 7.02(t, 1H), 7.16(d, 1H), 7.22(d, 1H), 7.35(d, 2H), 7.67(s, 1H), 8.39(s, 1H).

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mao, Yongjun; Zhu, Wenxiu; Kong, Xiaoguang; Wang, Zhen; Xie, Hua; Ding, Jian; Terrett, Nicholas Kenneth; Shen, Jingkang; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3090 – 3104;,
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Related Products of 104-11-0, 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 104-11-0 as follows.

To a solution under nitrogen gas of 2,4-dichloroquinoline (1.00 g, 5.0 mmol) in dry THF (10 ml) was added 4-chloro-N-methylbenzylamine (1.57 g, 10.1 mmol, 2 eq.) and t-BuONa (1.36 g, 14.1 mmol, 2.8 eq.). The resulting mixture was degassed 5 min with nitrogen, then Xantphos (292 mg, 0.51 mmol, 0.1 eq.) and Pd(OAc)2 (57 mg, 0.25 mmol) were added and the reaction mixture was heated under reflux for 3 h. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between brine and AcOEt and the aqueous layer was extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give a brown oil. The crude product was purified by flash chromatography (gradient Petroleum ether/DCM from 5/5 to 0/10) to give 800 mg (yield 50%) of a brown solid corresponding to 2-(4-chloro-N-methylbenzylamino)-4- chloroquinoline. Mass: (ES+) C17H14Cl2N2, required 317; found 317-319 [M+H], HPLC/MS method 1.

According to the analysis of related databases, 104-11-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 627-42-9, These common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, 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.

A solution of ethyl 3,4-dihydroxybenzoate (1.7 g, 9.3 mmol) was placed in a reaction flask and 8 mL of DMF was added to dissolve it. Potassium tert-butoxide (2.0 g, 17.8 mmol) and potassium iodide (1.0 g, 6.0 mmol), and the temperature was raised to 100 C. 2-Chloroethyl methyl ether (3.52 g, 37.2 mmol) was added dropwise and the reaction was continued for 12 h after completion of the dropwise addition. Cooled to room temperature, ice water (200 mL) was added, and extracted three times with ethyl acetate (3 x 200 mL). The organic phase was combined, washed three times with distilled water, three times with saturated brine, dried over anhydrous sodium sulfate overnight, filtered, and the filtrate was evaporated to dryness under reduced pressure to give an oil. The elution system was petroleum ether / ethyl acetate = 1) Ethyl 3,4-bis (2-methoxyethoxy) benzoate.

Statistics shows that 2-Methoxyethyl chloride is playing an increasingly important role. we look forward to future research findings about 627-42-9.

Reference:
Patent; Shandong University; Shandong Yikang Pharmaceutical Co., Ltd.; Zhao Guisen; Li Pengzhan; Shi Yongqiang; Yin Yanzhen; Wang Yongtao; (11 pag.)CN104725327; (2017); B;,
Chloride – Wikipedia,
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Application of 106131-61-7, 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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 5 (1.5 g, 1 mol) And tetraethylene glycol monomethyl ether (3.16ml, 1.5mol) were dissolved in 50ml of dichloromethane, Triethylamine (2.96 ml, 1.5 mol) was then added. After stirring at room temperature for 3 hours, The reaction was quenched with water, extracted with dichloromethane, dried and passed through a silica gel column. Compound 6b (2.8 g, 87%) was obtained.

The synthetic route of 3,6-Dichloro-1,2,4,5-tetrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Chemical Institute; Yang Guoqiang; Zhao Zhensheng; Wang Shuangqing; Hu Rui; Li Shayu; (12 pag.)CN107286186; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 553-82-2, 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. 553-82-2, name is 2,4-Dichloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To synthesize compound 96, to 2,4-dichloroanisole (5 mL, 36 mmol) in THF (22 mL) at -78 C. was added 2.5 M nBuLi (17 mL, 43 mmol) keeping the temperature below -65 C. After 30 min, the reaction was poured into frozen (-78 C.) trimethylborate (14 mL, 215 mmol) followed by another portion of trimethylborate (10 mL, 90 mmol) and allowed to warm to room temperature over 16 h. The solid suspension was poured into a 1 N HCl aqueous solution and stirred for 1 h. The suspension was filtered to give 3.6 g (46%) of a white solid contaminated most likely with B(OH)4. A second batch of crystals formed which were collected as an off-white solid that was compound 96 (5.8 g, 74%). 1H NMR DMSO-d6: delta 8.53 (s, 2H), 7.29 (d, J=8.8 Hz, 1H), 7.06 (d, J=8.8 Hz, 1H), 3.83 (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, 2,4-Dichloro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 64628-73-5, name is 3-Chloro-4-(trifluoromethoxy)aniline, 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 64628-73-5, Product Details of 64628-73-5

H. Synthesis of (6S)-6-({6-[3-chloro-4-(trifluoromethoxy)phenyl]-3-pyridinyl}methoxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (28) by the method of Scheme 4 An ice-cold mixture of 98% H2SO4 (0.75 mL) and water (2.25 mL) was added to 3-chloro-4-(trifluoromethoxy)aniline (53) (1.00 g, 4.73 mmol) and the resulting salt was crushed (using a glass rod) and cooled in an ice bath. A solution of NaNO2 (359 mg, 5.20 mmol) in cold water (0.75 mL, then 0.25 mL) was added drop-wise, and the mixture was stirred at 0 C. for 12 min. A solution of urea (42.6 mg, 0.709 mmol) in cold water (0.25 mL) was added, and the mixture was stirred at 0 C. for 3 min. Finally, a solution of KI (1.65 g, 9.94 mmol) in cold water (1.6 mL, then 0.2 mL) was added slowly, and the mixture was stirred at room temperature for 10 min, and then at 52 C. for 2 h. The resulting cooled mixture was diluted with ice-water (45 mL) and extracted with CH2Cl2 (4*50 mL). The extracts were sequentially washed with an aqueous solution of Na2SO3 (30 mL of 0.5%) and then with water (40 mL) and finally concentrated carefully under reduced pressure at 17 C. The resulting oil was chromatographed on silica gel, eluting with pentane, to give 2-chloro-4-iodo-1-(trifluoromethoxy)benzene (54) (1.24 g, 81%) as a colourless oil (a white solid on freezing); 1H NMR (CDCl3) delta 7.82 (d, J=2.1 Hz, 1H), 7.61 (dd, J=8.6, 2.1 Hz, 1H), 7.05 (dq, J=8.6, 2.0 Hz, 1H); HRAPCIMS calcd for C7H3ClF3IO m/z (M+) 323.8834, 321.8864, found 323.8834, 321.8861.

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; Global Alliance for TB Drug Development; US2012/28973; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

96558-78-0, name is 3-Bromo-5-chlorophenylamine, 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. HPLC of Formula: C6H5BrClN

To a solution of compound 1 (50 g, 242.2 mmol, 1 eq ) in 1 L of toluene and 100 mL of H2O was added potassium cyclopropyl(trifluoro)boranuide (39.4 g, 266.4 mmol, 1.1 eq), t- BuOK (81.5 g, 726.5 mmol, 3 eq) and Pd(dppf)Cl2.CH2Cl2 (19.8 g, 24.2 mmol, 0.1 eq) and purged with N2 for 3 times. The mixture was stirred at 90C for 16 hours. Then it was filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (S1O2, eluting with a gradient of petroleum ether:ethyl acetate =1:0 to 3:1) to get 37.5 g of compound 2 (223.7 mmol, 92.4% yield) as a yellow oil.

The synthetic route of 96558-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, 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 13918-92-8, Recommanded Product: 2,4-Difluorobenzene-1-sulfonyl chloride

c) lambda/-[5-bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide; To a cooled (0 0C) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (20.3 g, 100 mmol) in pyridine (200 mL) was added slowly 2,4-difluorobenzenesulfonyl chloride (21.3 g, 100 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h, at which time the reaction was diluted with water (500 mL) and the solids filtered off and washed with copious amounts of water. The precipitate was dried in a vacuum oven at 50 0C to give N-[5-bromo-2-(methyloxy)-3-pyridinyl]-2,4- difluorobenzenesulfonamide (12 g, 31.6 mmol, 31.7 % yield) MS(ES)+ m/e 379.0, 380.9 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/55418; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3843-97-8, name is 5-Chloro-2-ethylaniline, 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 3843-97-8, Quality Control of 5-Chloro-2-ethylaniline

Step 4: 4-Chloro-1-ethyl-2-iodobenzeneA mixture of 5-chloro-2-ethylaniline (3.35 g, 21.5 mmol), p-toluensulfonic acid (12.29 g, 64.6 mmol) and water (2.15 mL) were ground in a mortar for few minutes, to obtain a homogeneous paste to which solid sodium nitrite (3.71 g, 53.8 mmol) was added and the paste ground for 10 min. Solid potassium iodide (8.94 g, 53.8 mmol) was added and the paste ground for 20 min. The paste was then dissolved in water (50 mL) and treated with sodium sulfite (10% aq. sol.), before being extracted with EtOAc (3 x 100 mL). The combined organic layers were dried over sodium sulfate and the crude was purified by flash chromatography (hexane) to obtain the title compound as a light-yellow oil (4.35 g, 76%).1H NMR (400 MHz, DMSO- /6) delta ppm 1.12 (t, J=7.51 Hz, 3 H), 2.66 (q, J=7.53 Hz, 2 H), 7.29 – 7.35 (m, 1 H), 7.42 (dd, J=8.30, 2.20 Hz, 1 H), 7.87 (d, J=2.20 Hz, 1 H).

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

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BANDIERA, Tiziano; BERTRAND, Jay Aaron; GNOCCHI, Paola; MIRIZZI, Danilo; NESI, Marcella; PANZERI, Achille; WO2012/143248; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 622-86-6, A common heterocyclic compound, 622-86-6, name is (2-Chloroethoxy)benzene, molecular formula is C8H9ClO, 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.

2-Bromophenyl acetic acid (5.0 g, 23.3 mmol,)was suspended in trifluoroacetic anhydride (13.5 mL, 93.5 mmol).Chloroethyoxylbenzene (3.3 mL, 23.3 mmol) was added to the stirred suspensiondropwise. The resulting mixture was allowed to stir overnight at roomtemperature. The reaction was quenched with 40% aqueous sodium hydroxidesolution and then extracted with ethyl acetate (2 x 20 mL). The combined organic layers were dried overanhydrous magnesium sulfate and concentrated on a rotary evaporator. The resulting residue was purified bychromatography on silica gel (ethyl acetate/hexane) to afford 5.98 g (73%) ofthe desired product as a light orange solid. 1H NMR (400 MHz, CDCl3)delta 8.05 (d, J = 8.9 Hz, 2H), 7.60 (d, J = 8.5 Hz, 1H), 7.24 (m, 2H), 7.18 (m,1H), 6.96 (d, J = 9.0 Hz, 2H), 4.40 (s, 2H), 4.37 (t, J = 5.5 Hz, 2H), 3.88 (t,J = 5.7 Hz, 2H); MS (ESI) (m/z) 354.0/356.0 (M+H)+.

The synthetic route of 622-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Childers, Wayne; Fan, Rong; Martinez, Rogelio; Colussi, Dennis J.; Melenski, Edward; Liu, Yuxiao; Gordon, John; Abou-Gharbia, Magid; Jacobson, Marlene A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics