Tag: M.W=100-200

Electric Literature of 4584-46-7, These common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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-Dimethylaminoethyl chloride hydrochloride (0.97 g, 6.70 mmol) was added to a mixture of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (1 .00 g, 5.15 mmol) and caesiumcarbonate (5.54 g, 17.01 mmol) in dry N,N-dimethylformamide (20 mL) at 0C. After stirring for30 mm the ice-water bath was removed. The reaction mixture was stirred at room temperaturefor three days. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with brine (3×100 mL). The organic layer was dried with sodium sulfate and concentrated in vacuo to afford 1 .00 g (3.41 mmol; 66% of theory) of the title compound.GO-MS (Method L9): R1 = 4.48 mm; (no mass detected)1 H NMR (300 MHz, Chloroform-d, Method M2) 6 7.78 (s, 1 H), 7.74 (s, 1 H), 4.23 (t, J = 6.8 Hz,2H), 2.76 (t, J = 6.8 Hz, 2H), 2.26 (s, 6H), 1.31 (s, 12H).

The synthetic route of 4584-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER ANIMAL HEALTH GMBH; KOeHLER, Adeline; WELZ, Claudia; BOeRNGEN, Kirsten; KULKE, Daniel; ILG, Thomas; KOeBBERLING, Johannes; HUeBSCH, Walter; SCHWARZ, Hans-Georg; GOeRGENS, Ulrich; EBBINGHAUS-KINTSCHER, Ulrich; HINK, Maike; NENNSTIEL, Dirk; RAMING, Klaus; ADAMCZEWSKI, Martin; BOeHM, Claudia; (269 pag.)WO2017/178416; (2017); A1;,
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Synthetic Route of 108-41-8, These common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, 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: A dried round bottomed flask equipped with a magnetic stir bar was charged with 15 mg Polymer anchored-Pd(II) C catalyst (PS-8-AQ-Pd), 2-phenyl pyridine (0.5 mmol), benzyl alcohol (1.0 mmol)and TBHP (2.0 mmol) were added to a reaction vessel. The mixture was stirred at 110 C for 8 h, then cooled to room temperature and catalyst was filtered, the filtrate was extracted with ethyl acetate(3 10 mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethylacetate/hexane (1:4) as eluent to give the corresponding ortho acylation products. The products were characterized by 1H NMR,13C NMR and HRMS.

The synthetic route of 108-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perumgani, C. Pullaiah; Parvathaneni, Sai Prathima; Kodicherla, Balaswamy; Keesara, Srinivas; Mandapati, Mohan Rao; Inorganica Chimica Acta; vol. 455; (2017); p. 105 – 111;,
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Synthetic Route of 445-13-6, 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. 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of triphosgene (609 mg, 2.14 mmol) in toluene (5 mL) was added dropwise a solution of 3-chloro-4-(trifluoromethyl)aniline (100 mg, 0.51 mmol) and refluxed at 80 C for 0.5 h. Then the mixture was concentrated to give crude 2-chloro-4- isocyanato-l-(trifluoromethyl)benzene used in the next step without purification. To the solution of 2-chloro-4-isocyanato-l-(trifluoromethyl)benzene in THF was added (S)-3-(5- (aminomethyl)-l-oxoisoindolin-2-yl)azepane-2,7-dione (TFA salt) (59.1 mg, 0.21 mmol), followed by TEA (42 mg, 0.42 mmol). The mixture was stirred at RT for 2 h. The mixture was concentrated and purified by silica gel chromatography eluting with MeOH/DCM from 0% to 8% to give Compound 12 (29.4 mg, 28%) as a white solid. MS (ESI) m/z 509.0 [M+H]+. MR (400 MHz, DMSO-d6) delta 10.72 (s, 1 H), 9.36 (s, 1 H), 7.91 (s, 1 H), 7.70- 7.68 (m, 2 H), 7.54 (s, 1 H), 7.45-7.41 (m, 2 H), 7.06 (t, J =14 Hz, 1 H), 5.23 (dd, J =7.6, 12.8 Hz, 1 H), 4.52 (s, 2 H), 4.43 (d, J =6.0 Hz, 2 H), 3.12-3.04 (m, 1 H), 2.61-2.55 (m, 1 H), 2.28-2.22 (m, 1 H), 2.12-1.96 (m, 2 H), 1.84-1.76 (m, 1 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, 3-Chloro-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
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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. 7006-52-2, name is N-Methyl-3-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8ClN

General procedure: Bi(NO3)3.5H2O (2 equiv, 0.6 mmol), Pd(OAc)2 (0.015 mmol, 5 mol percent) were added into a 25mL oven-dried Schlenk tube, the tube was evacuated and backfilled with Ar (repeated three times in 30 min). Under a counter flow of Ar, N-substituted aniline (1 equiv, 0.3 mmol) was added by syringe firstly, 1.5 mL TFE and 0.5 mL TFA were then added by disposable medical syringes. The flask was sealed and the mixture was stirred firstly at room temperature for15 min, then allowed to stir in a preheated oil bath at 90 °C for 24 h.The mixture was cooled to room temperature when the reaction was completed. Next, the solution was diluted by 10 mL ethyl acetate and filtered the insoluble matters, washed the organic phases by 5percent NaHCO3 solution after the extraction, and extracted the aqueous phases by ethyl acetate (3×15 mL) to collect organic phases. All the organic solutions were washed by brine, dried 30 min with anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude products were purified by chromatography on silica gel, eluting with ethyl acetate/petroleum ether(5/1-2/1).

According to the analysis of related databases, 7006-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Yi-Si; Mao, Long; Bu, Xiao-Song; Dai, Jian-Jun; Xu, Hua-Jian; Tetrahedron; vol. 71; 23; (2015); p. 3827 – 3832;,
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Adding a certain compound to certain chemical reactions, such as: 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, 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 13078-79-0, Quality Control of 2-(3-Chlorophenyl)ethanamine

General procedure: 2.5mmol Thiazole-4-carboxyli acid and 2.0mmol amine were dissolved in 25mL DCM in a dry flask with continuous stirring, followed by the addition of 2.5mmol 3-(3-Dimethylaminopropyl)-1-Ethylcarbodiimide Hydrochloride (2.5mmol). When the temperature of the reaction system cooled to 0C, 50mg 4-dimethylaminopyridine (0.2mmol) was added dropwise and reacted for 1hat 0C. Then the reaction temperature was elevated to room temperature for another 4h. The reaction was stopped by adding 25mL saturated NaHCO3 solution and extracted twice with 20mL dichloromethane (2×20mL). The extracted organic layers were first dried by anhydrous Na2SO4, and then filtered and concentrated under vacuum distillation, obtaining the crude products. Finally, the crude products were further purified using column chromatography (ethy lacetate: petroleum ether, 1:5).

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; Li, Shengrong; Chen, Siyu; Fan, Jilin; Cao, Zhen; Ouyang, Weihao; Tong, Ning; Hu, Xin; Hu, Jie; Li, Peishan; Feng, Zifeng; Huang, Xi; Li, Yuying; Xie, Mingshan; He, Ruikun; Jian, Jingyi; Wu, Biyuan; Xu, Chen; Wu, Weijian; Guo, Jialiang; Lin, Jing; Sun, Pinghua; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 64 – 73;,
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Electric Literature of 2687-12-9, A common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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.

In the reaction (r-1 ‘), a benzene derivative (3A’) (15.2 g, 0.1 mol) and triethyl phosphite represented by the chemical formula (B) (25 g, 0.15 mol ), And the mixture was stirred at 180 C. for 8 hours and then cooled to room temperature. Thereafter, unreacted or remaining triethyl phosphite was distilled off under reduced pressure to obtain a phosphonate derivative (3C ‘) as a white liquid. The yield from the benzene derivative (3A ‘) of the phosphonate derivative (3C’) was 23.5 g (yield: 92 mol%).

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyocera Document Solutions Co., Ltd.; Okada, Hideki; Sugai, Akio; Kojima, Kensuke; (52 pag.)JP2017/114808; (2017); A;,
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Some common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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. Product Details of 6940-78-9

The solution of isobutyronitrile (0.7 g, 10 mmol) in THF (20 mL) was cooled to -80 C and LDA (Lithium diisopropylamide) solution (2.0 M in hexane, 6 mL, 12 mmol) was added over 10 min. The solution was stirred 30 min, and then a solution of 1-bromo-5-chloropentane (1.8 g, 10 mmol) in THF (10 mL) was added over 5 min. After stirring for 90 min, 6 N HCl (6 mL) was added slowly and the temperature allowed to rise to rt. The residue was concentrated under reduced pressure and EtOAc (20 mL) was added. The separated organic layer was washed with water (10 mL). The organic solvent was dried with Na2SO4 and concentrated in vacuo to give the crude product. Purification by column chromatography (petroleum ether (60-90 C)/EtOAc) gave 1.5 g of 2,2-dimethyl-7-chloroheptanenitrile (88%) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 3.57 (t, J = 6.6 Hz, 2H), 1.92-1.72 (m, 2H), 1.58-1.44 (m, 6H), 1.36 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6940-78-9, its application will become more common.

Reference:
Article; Liu, Peng; Xu, Xing; Chen, Lili; Ma, Lei; Shen, Xu; Hu, Lihong; Bioorganic and Medicinal Chemistry; vol. 22; 5; (2014); p. 1596 – 1607;,
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Electric Literature of 5013-77-4,Some common heterocyclic compound, 5013-77-4, name is N-Methyl-2,4-dichlorobenzylamine, molecular formula is C8H9Cl2N, 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: 6.11. 4-Chloro-N-(2,4-dichlorobenzyl)pyrimidin-2-amine (13) and 2-chloro-N-(2,4-dichlorobenzyl)pyrimidin-4-amine (14); 2,4-Dichlorobenzylamine (1.0 mL, 7.4 mmol) was added to a stirring solution of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol) and DIPEA (1.8mL, 10.1mmol) in anhydrous DCE (10mL) and the reaction mixture was stirred at 20C under a nitrogen atmosphere for 24h. LCMS showed the presence of a mixture of regioisomers (System A, RT=1.10min, 63% and 1.25min, 27%). The reaction mixture was diluted with water (50mL) and extracted with DCM (3×50mL). The combined organic extracts were washed with brine (50mL), dried using a hydrophobic frit and evaporated under reduced pressure. The residue was purified by column chromatography on a silica column, using a gradient of 0-100% ethyl acetate-cyclohexane over 40 min. The appropriate fractions were combined and evaporated under reduced pressure to afford the two regioisomers as white solids: less-polar isomer 13 (400 mg, 21%) and the more-polar isomer 14 (950 mg, 49%); 6.23 2-Chloro-N-(2,4-dichlorobenzyl)-N-methylpyrimidin-4-amine (24) Prepared from 12 (0.50 g, 3.4 mmol), N-methyl-(2,4-dichlorobenzyl)amine (0.64 g, 3.4 mmol) and DIPEA (1.3 mL, 7.4 mmol) according to the procedure described for the preparation of 14 to give 24 (0.39 g, 38%) as a white solid: 1H NMR delta (400 MHz, CD3OD) 8.04 (br. s, 1H), 7.52 (d, J = 2.0 Hz, 1H), 7.31 (dd, J = 8.0, 2.0 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 6.66 (br. s, 1H), 4.89 (s, 2H) (obscured by HOCD3), 3.13 (br. s, 3H); LCMS (System A, UV, ES) RT = 1.28 min, [M + H]+ = 302, 304, 306, 100% purity.

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-2,4-dichlorobenzylamine, its application will become more common.

Reference:
Article; Shukla, Lena; Ajram, Laura A.; Begg, Malcolm; Evans, Brian; Graves, Rebecca H.; Hodgson, Simon T.; Lynn, Sean M.; Miah, Afjal H.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Stephen A.; Slack, Robert J.; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 14 – 25;,
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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);,
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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;,
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