Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl 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 61881-19-4, Product Details of 61881-19-4

To a solution of 28 (0.91 g, 1.7 mmol) in acetone (17 mL) wereadded CF3C(=NPh)Cl (0.53 mL, 3.3 mmol) and K2CO3 (1.1 g,8.3 mmol) at 0 C. After stirring for 2.5 h at the same temperature, thecompletion of the reaction was confirmed by TLC (5:1 n-hexane/EtOAc). The reaction mixture was filtered through Celite pad and thepad was washed with CHCl3. The filtrate and washings were concentrated.The resulting residue was purified by silica gel columnchromatography (25:1 n-hexane/EtOAc) to give 29 (1.2 g, quant.) ascolorless syrup. 1H NMR (500 MHz, CDCl3) delta 7.44-6.70 (m, 17H, Ar),5.08-4.83 (br m, 4H, H-1, H-2, H-3, H-4), 4.15-3.65 (br m, 3H, H-5, H-6a, H-6b), 1.08 (s, 9H, tBu), 1.01 (s, 9H, tBu); 13C NMR (125 MHz,CDCl3) delta 143.5, 143.3, 138.9, 138.6, 135.4, 135.3, 135.3, 135.2, 133.1,133.1, 128.7, 128.4, 128.4, 128.3, 128.2, 128.2, 128.1, 128.1, 128.0,127.9, 127.7, 127.7, 127.7, 126.9, 126.5, 126.2, 126.1, 126.1, 126.0,126.0, 125.6, 124.4, 119.4, 119.2, 84.0, 81.2, 80.0, 77.9, 77.7, 77.5,75.8, 75.5, 75.5, 73.9, 71.0, 68.8, 66.5, 66.2, 27.4, 27.0, 26.9, 22.7,20.0. HRMS (ESI) m/z: found [M+Na]+ 744.2935, C40H46F3NO6Sicalcd for [M+Na]+ 744.2939.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Takato, Koichi; Kurita, Motoki; Yagami, Nahoko; Tanaka, Hide-Nori; Ando, Hiromune; Imamura, Akihiro; Ishida, Hideharu; Carbohydrate Research; vol. 483; (2019);,
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Electric Literature of 823-57-4, A common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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.

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous bromide (0.02 mmol), 2-bromo-5-chloroaniline (0.4 mmol),1,10-azaphenanthroline (0.04 mmol), potassium carbonate (0.6 mmol),Carbon disulfide (0.6 mmol) and toluene (2.0 mL) were added by syringe under oxygen.The reaction tube was placed in a 110 C oil bath and stirred for 12 hours.The resulting solution was cooled to room temperature, and 2 mL of deionized water was added to the reaction solution.Mix well, each time with 3mL of ethyl acetate as extractant through liquid separation extraction operation,The crude product is extracted from the reaction solution, and the extract is combined.The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (silica gel, 200 to 300 mesh, eluent, petroleum ether/ethyl acetate (10:1 v/v)).The target product was obtained in 65.2 mg, yield 83%.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
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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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H6BrClO

EXAMPLE 21 Preparation of 5-Hydroxy-3-(3-chloro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one of Formula (67) [0134] A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3*35 ml), washed with water (2*20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A) [0135] wherein R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (1.32 g, 37%). [0136] A solution of the above alcohol of the formula (4A) wherein R1=R5=R6 =R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl wherein (0.95 g, 1.83 mmol) in dry dichloromethane (15 ml) was cooled to 0 C., pyridinium dichromate (1.92 g, 8.17 mmol) was added and the mixture was stirred at room temperature for 3 h. Filtration through celite (3.00 g), washing with dichloromethane (30 ml) and concentration afforded the crude product which was purified by silica gel column chromatography (eluent-3% acetone in pet ether) to yield the title compound of the formula (1B) wherein R=OTBS, R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (0.32 g, 34%), which on deprotection of TBDMS group using the procedure described in example 10 furnished the compound of formula (67). [0137] Spectral data of compound of the formula of structure (67) [0138] 1H NMR(CDCl3+CCl4): delta 2.96 (dd, J=18 Hz and 2 Hz, 1H), 3.33 (dd, J =18 Hz and 6 Hz, 1H), 3.75 (s, 6H), 3.86 (s, 3H), 3.91 (s, 3H), 4.45-4.54 (m, 1H), 6.42 (s, 2H), 6.81 (d, J=8 Hz, 1H), 7.21-7.29 (m, 1H), 7.48 (bs, 1H). [0139] 13C-NMR (CDCl3+CCl4): delta 37.79, 55.87 (2C), 60.58, 71.57, 106.23 (2c), 111.31, 122.41, 126.82, 127.59, 128.58 (2C), 130.05, 135.90, 138.07, 153.36 (2C), 156.48, 162, 51, 206.95

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; DABUR RESEARCH FOUNDATION; US2003/229146; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 18282-59-2, A common heterocyclic compound, 18282-59-2, name is 4-Bromo-1,2-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Tris [(DIBENZYLIDINEACETONE)] di palladium (0) (5 molpercent ; 23 mg) was added to a mixture of 1- [[4- (3-PIPERIDIN-1-YL-PROPOXY)-PHENYL]-PIPERAZINE (D11)] (150 mg; 0.49 [MMOL),] 3, 4-dichloro bromo benzene (160 mg; 1.2 eq), sodium [TERT-BUTOXIDE] (71 mg; 1.1 eq) and racemic 2,2′- bis (diphenylphosphino)-1, 1′-binaphthyl (7.5 molpercent ; 24 mg) in dry [TOLUENE] [(3ML).] The resulting mixture was heated at reflux under argon for 18 hours. The reaction was allowed to cool to room temperature and diluted with ethyl acetate (10 ml). The resulting solids were removed by filtration and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica eluting with 3percent methanol in [DICHLOROMETHANE] to afford the title compound as a buff solid (45 mg) MS (ES+) [M/E] 448 [M+H] +.

The synthetic route of 18282-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/35556; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 121-27-7, The chemical industry reduces the impact on the environment during synthesis 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, I believe this compound will play a more active role in future production and life.

A solution of 8 (2.56 g, 10.1 mmol), ethyl bromoacetate (7.0 mL, 63 mmol), and N,N-diisopropylethylamine (7.0 mL, 41 mmol) was stirred at 140 C for 5 h. The reaction mixture was cooled down, and diluted with EtOAc (100 mL). The organic layer was washed with 10% aqueous citric acid (100 mL * 2), saturated aqueous NaHCO3, and brine, and dried over MgSO4. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The residue oil was purified by silica gel column chromatography (hexane/EtOAc = 95:5 to 80:20) to afford 9 (3.68 g, 85%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 1.20 (t, J = 7.2, 6H), 4.10 (s, 4H), 4.11 (q, J = 7.2, 4H), 6.76 (d, J = 8.7, 1H), 6.81-6.87 (m, 4H), 7.24 (d, J = 8.7, 2H). 13C NMR (100 MHz, CDCl3): delta (ppm) 14.15, 54.04, 60.95, 118.72, 119.42, 121.65, 122.31, 127.95, 129.56, 129.94, 142.40, 145.35, 155.99, 170.52. LC-MS (ESI) m/z 426, 428 [M+H]+.

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, 5-Chloro-2-(4-chlorophenoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nakao, Akira; Suzuki, Hiroko; Ueno, Hiroaki; Iwasaki, Hiroshi; Setsuta, Tomofumi; Kashima, Akiko; Sunada, Shinji; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4952 – 4969;,
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

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: 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

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;,
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