Author: Jessica.F

13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, 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. name: 2-(3-Chlorophenyl)ethanamine

General procedure: 7-(2-Bromoethyl)-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (4) (100 mg, 0.32 mmol) was dissolved in dryCH2Cl2 (30 mL) and cooled to 0 C. A solution of PBr3 (90 lL,0.94 mmol) in dry CH2Cl2 (20 mL) was added dropwise. The solutionwas allowed to warm to rt and stirred for 1 h. Then it was cooled to0 C again and the excess of PBr3 was carefully hydrolyzed by slowaddition of saturated aq NaHCO3 solution (5 mL). The pH was set at8 by addition of more saturated aq NaHCO3 solution. Then, theorganic layer was separated and the aqueous layer extracted withCH2Cl2 (2 50 mL). The combined organic extracts were dried overNa2SO4 and the solvent was removed under reduced pressure. Thecrude 7-(2-bromoethyl)-8-bromo-1,3-dimethylpurine-2,4-dione (5) was dissolved in a mixture of dimethoxyethane (10 mL) anddiisopropylethylamine (DIPEA) (0.5 mL). Then, the appropriateamine (0.64 mmol)wasadded and the solutionwasstirred overnightat rt. The volatiles were removed under reduced pressure andtetrahydropyrazino[2,1-f]purinediones 6-63 precipitated uponaddition ofH2O(20 mL). For purification, thecompounds were eitherfiltered off and washed with H2O (3 5 mL) and subsequently withdiethylether (3 10 mL), or subjected to column chromatography(silica gel, gradient of CH2Cl2/MeOH 1:0 to 40:1).

The synthetic route of 13078-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Brunschweiger, Andreas; Koch, Pierre; Schlenk, Miriam; Rafehi, Muhammad; Radjainia, Hamid; Kueppers, Petra; Hinz, Sonja; Pineda, Felipe; Wiese, Michael; Hockemeyer, Joerg; Heer, Jag; Denonne, Frederic; Mueller, Christa E.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5462 – 5480;,
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Synthetic Route of 104-52-9,Some common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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: To a solution of compound 6 (0.06mmol) in 2 ml DMF was added potassium carbonate (0.18 mmol). The mixture was heated to 90 C and l-(2- chloroethyl)piperidine hydrochloride (0.066 mmol) was added. The reaction mixture was then stirred at 90 C for two hours. After the reaction was completed, the mixture was poured into 50 ml water and then extracted with dichloromethane (50 ml x 3). The organic layer was dried with anhydrous Na2S04 and evaporated to dryness under reduced pressure to give the crude product, which was further purified by flash silica gel column chromatography (methanol : dichloromethane = 1:12) to give a light yellow paste (yield 63%).

The synthetic route of 104-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INCORPORATED; LI, Chenglong; MAO, Liguang; (0 pag.)WO2019/165158; (2019); A1;,
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Synthetic Route of 1005-56-7,Some common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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 mixture of the dibromofluoroalcohol (1.0 equiv.), acid chloride (1.1-1.5 equiv.) and triethylamine (2.2-3.0 equiv.) in THF was stirred for 1 h at 0 C, then for additional appropriate period (usually 2-3 h) at room temperature. As in the cases of 1e, 1f, 8c-e catalytic amount of 4-dimethylaminopyridine was also added. Usual workup (addition of water, extraction with diethyl ether or ethyl acetate, dried over MgSO4) followed by purification by silica gel column chromatography (mixture of hexane and EtOAc as eluent) gave the corresponding ester.

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

Reference:
Article; Saito, Akio; Tojo, Manabu; Yanai, Hikaru; Wada, Fukiko; Nakagawa, Muga; Okada, Midori; Sato, Azusa; Okatani, Rieko; Taguchi, Takeo; Journal of Fluorine Chemistry; vol. 133; (2012); p. 38 – 51;,
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Application of 2106-04-9, These common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, 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.

Will 25g compound 214.5g of compound 3,400 mL of isopropanol was added to the reaction flask.Warming up to reflux for 3 h,After the TLC detection reaction is completed, the temperature is lowered to 0 to 40 C, and suction filtration is performed.Then drying at 40 to 50 C to obtain 35 g of compound 4;

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tonghua Normal College; Geng Xiaoyu; Xue Mingxing; Zang Hao; Liu Xuekun; Sun Renshuang; Xue Changsong; Zhang Haifeng; (13 pag.)CN109438423; (2019); A;,
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Related Products of 1435-48-9, 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 1435-48-9 as follows.

(S)-3-((R)-1-Hydroxy-2-methoxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (10.0 mg, 40.8 mumol) was dissolved in DMF (0.1 mL). NaH (1.5 mg, 61.1 mumol) was slowly added and the mixture was stirred at room temperature for 15 minutes. Then, 2,4-dichloro-1-fluorobenzene (20.2 mg, 122 mumol) was added. The mixture was stirred at 100 C. for 1 hour, then cooled to room temperature. The mixture was concentrated then dissolved in 1.2M HCl in EtOH (1.0 mL, 1.2 mmol) and stirred overnight at room temperature. The product was concentrated and purified by preparative HPLC to yield the title compound as a mono-TFA salt (12.8 mg, 99% purity). MS m/z: [M+H]2+ calcd for C13H17Cl2NO2, 290.06; found 290.0.

According to the analysis of related databases, 1435-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STANGELAND, Eric; SCHMIDT, Jane; SAITO, Daisuke Roland; HUGHES, Adam; PATTERSON, Lori Jean; US2011/21597; (2011); A1;,
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Synthetic Route of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: Following the similar procedures as for compound 13a gave compound13b, white solid, 55percent. 1H NMR (400 MHz, CDCl3) delta 8.10 (d,J=5.1 Hz, 1H), 7.43 (d, J=1.8 Hz, 1H), 7.37 (d, J=8.2 Hz, 1H),7.21?7.15 (m, 1H), 6.84 (d, J=5.1 Hz, 1H), 4.79 (t, J=5.6 Hz, 1H),4.65?4.59 (m, 2H), 3.78?3.68 (m, 1H), 3.62?3.53 (m, 2H), 3.21 (t,J=6.3 Hz, 2H), 3.05?2.95 (m, 2H), 2.82 (s, 3H), 2.78 (s, 3H), 2.58 (t,J=6.9 Hz, 2H), 2.43?2.33 (m, 2H), 2.08?1.98 (m, 4H), 1.87?1.76 (m,4H), 1.72?1.61 (m, 2H). 13C NMR (126 MHz, CDCl3) delta 169.41, 154.57,146.52, 144.37, 140.39, 132.47, 130.98, 130.44, 129.56, 127.05,114.53, 112.28, 55.59, 54.97, 53.01, 46.27, 45.72, 44.85, 38.50, 29.69,28.71, 28.56, 26.62, 22.37. HRMS (ESI): calcd for C26H36Cl2N5O3S [M+H]+: 568.1910; found 568.1898. Retention time 2.35 min,>97percentpure.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Li-Huai; Wang, Zhi-Long; Xie, Xin; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3559 – 3572;,
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Electric Literature of 821-10-3, These common heterocyclic compound, 821-10-3, name is 1,4-Dichlorobut-2-yne, 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: To a solution of diyne (50 mg) in dry solvent (5mL) in microwave reaction vessel propargyl halide 7b/c/e/f (2 equiv.) and Mo(CO)6 (5 mol%) were added andthe reaction mixture was irradiated in a CEM Discover microwave synthesizer for10 min. under standard conditions. Afterthe completion of reaction (TLC monitoring), the solvent was concentrated atreduced pressure and the crude product was purified by silica gel columnchromatography

The synthetic route of 821-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kotha, Sambasivarao; Sreevani, Gaddamedi; Tetrahedron Letters; vol. 56; 43; (2015); p. 5903 – 5908;,
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Electric Literature of 202925-07-3, 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. 202925-07-3, name is 2-Chloro-1-fluoro-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

2- Chloro-3-fluoro-6-methoxybenzaldehydeTo a solution of 2-chloro-1 -fluoro-4-methoxybenzene (28.5 g, 178 mmol) in i-butyl methyl ether (200 mL, dried over anhydrous MgS04) at -78 C was added 2.5 M n-butyl lithium in hexanes (107 mL, 268 mmol). After 3 h, methyl formate (18.76 mL) was added dropwise while keeping the temperature below -60 C. The reaction mixture was quenched with sat. aq. ammonium chloride (250 mL) after 45 minutes and the organic layer was separated. The aq. layer was extracted with ethyl acetate (2×100 mL), and the combined organic layers were washed with water (200 mL) followed by brine, dried (Na2S04) and concentrated to give a residue which on trituration with hexanes gave solids. The solids were filtered, taken again in hexanes and heated over a steam bath. The mixture was cooled, and the light yellow desired product filtered off and air-dried to give the title compound. 1H NMR (400 MHz, CDCI3): delta = 10.48 (d, J = 0.8 Hz, 1 H), 7.31 (dd, J = 9.4, 7.8 Hz, 1 H), 6.88 (dd, J = 7.8, 3.8 Hz, 1 H), 3.92 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1-fluoro-4-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; LI, An-Hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WO2011/143646; (2011); A1;,
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Reference of 1298031-93-2, 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. 1298031-93-2, name is 6,8-Dichloro-2-methylimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of intermediate 2 (250 g), morpholine ([CAS 110-91-8], 103 g, 1190 mmol)and N,N-diisopropylethylamine ([CAS 7087-68-5], 208.7 g, 1623 mmol) in CH3CN (2000 mL) was refluxed for 5 h. Then, the reaction mixture was concentrated underreduced pressure and the residue was purified by column chromatography over silicagel (eluent: petroleum ether/ethyl acetate, 3/1) to give 70 g (22.4%) of intermediate 3 as a yellow solid.

The synthetic route of 6,8-Dichloro-2-methylimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LECLERCQ, Laurent, Christian, L.; BARTOLOME-NEBREDA, Jose, Manuel; CONDE-CEIDE, Susana; VAN GOOL, Michiel, Luc, Maria; WO2014/9305; (2014); A1;,
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Some common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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. name: 6-Chloroimidazo[1,2-b]pyridazine

General procedure: [0129] To a suspension of Zn powder (2.5 g, 38 mmol) in 1,4-dioxane (40 ml) was added iodine (0.9 mmol) and themixture was placed under an atmosphere of nitrogen. The benzyl bromide (19 mmol) was added in portions (after thefirst portion the mixture was gently heated to initiate reaction). Subsequent portions did not require heating and once allthe portions were added the mixture was allowed to stir at room temperature for 4 hours. After this time the mixture wasallowed to settle and the liquid was decanted from the excess Zinc and the resulting solution could be used immediatelyin the next reaction.[0130] A solution of the alkyl Zinc reagent (see note below) (2 eq.) was added to NiCl2dppp (10 mol %) under anatmosphere of nitrogen and the mixture was stirred at room temperature for 5 minutes. After this time the 6-chloroimidazo[1,2-b]pyridazine (1 eq.) was added as a solid in one portion and the mixture was heated at 50 C for 18 hours.The mixture was cooled to room temperature and a saturated aqueous solution of NH4Cl was added followed by EtOAc.The mixture was filtered through celite and the phases were separated. The organic phase was washed with brine, dried(MgSO4) and concentrated under reduced pressure and the residue was purified by column chromatography on silicagel (mixtures of Ethyl Acetate and Petroleum Ether

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6775-78-6, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); A1;,
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