Category: chlorides-buliding-blocks

Application of 16799-05-6,Some common heterocyclic compound, 16799-05-6, name is 3-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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 compound 3 or 4, R-X (3 equiv.) and Cs2CO3 (3 equiv.) in acetone/DMF (10 mL/10mL) was stirred at proper temperature (25-80C) for 20h. The reaction was quenched with water (30mL) and extracted with ethyl acetate (¡Á3). The organic layer was collected and washed with brine, and then dried over anhydrous MgSO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography.5.4.10 1-(3-Chlorophenethoxy)-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one (14) Following the general method, compound 3 (0.19 g, 0.06 mmol), 3-chloro-1-phenethyl bromide (0.30 g, 1.37 mmol) and K2CO3 (0.26 g, 1.85 mmol) were used at 80 C. The purification was conducted with eluent (ethyl acetate/n-hexane = 1:3) to give compound 14 (0.04 g, 15.4%) as a white solid. m.p. 146-148 C; Rf 0.63 (eluent: ethyl acetate/n-hexane = 1:1); HPLC: RT 4.05 min (condition A, purity: 98.2%); 1H NMR (CDCl3, 400 MHz) delta 2.78 (dd, J = 2.4, 4.8 Hz, 1H), 2.95 (t, J = 4.4 Hz, 1H), 3.28 (t, J = 7.2 Hz, 2H), 3.36-3.40 (m, 1H), 4.00 (dd, J = 7.0, 11.2 Hz, 1H), 4.25 (t, J = 7.2 Hz, 2H), 4.35 (dd, J = 2.8, 11.2 Hz, 1H), 6.35 (d, J = 2.4 Hz, 1H), 6.51 (d, J = 2.4 Hz, 1H), 7.20-7.38 (m, 5H), 7.43 (dd, J = 2.0, 2.0 Hz, 1H), 7.64 (ddd, J = 1.6, 7.2, 8.8 Hz, 1H), 8.31 (dd, J = 2.0, 8.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 35.5, 44.8, 50.0, 69.4, 70.1, 94.0, 96.6, 108.1, 117.2, 123.4, 124.9, 127.0, 127.9, 129.6, 130.0, 133.9, 134.4, 140.3, 155.2, 159.2, 161.4, 163.7, 175.3, 175.4 ppm.

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

Reference:
Article; Park, Seojeong; Hong, Eunji; Kwak, Soo Yeon; Jun, Kyu-Yeon; Lee, Eung-Seok; Kwon, Youngjoo; Na, Younghwa; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 211 – 225;,
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Reference of 10272-06-7, These common heterocyclic compound, 10272-06-7, name is 3-Chloro-5-methoxyaniline, 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.

(5.0 g, 31.72 mmol) was added to a stirred solution of (2) (3.11 g,31.72 mmol) in Et20 (60 mL) at a The reaction mixture was stirred at rt for 4 hr. The resulting mixture was evaporated in vacuo to give the crude product. This was triturated with Et20 and dried in vacuo to give 5.0 g (61.7% yield) of pure product as an off-whitesolid, which was used without further purification in the next step. LCMS m/z 256 [M + H- 11, 25 [M + H + 11, 264 [M + H + 31; (99.4% purity). ?H NMR (400 MHz, DMSO-d6) oe12.89 (br s, 1H), 10.43 (s, 1H), 7.36 (dd, J = 2.0 Hz, J = 1.6 Hz, 1H), 7.16 (dd, J = 2.0 Hz, J = 2.0 Hz, 1H), 6.76 (dd, J = 2.4 Hz, J = 2.0 Hz, 1H), 6.44 (d, J = 12 Hz, 1H), 6.31 (d, J = 12 Hz, 1H), 3.75 (s, 3H).

The synthetic route of 10272-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLATLEY DISCOVERY LAB, LLC; ZAWISTOSKI, Michael, P.; DESHPANDE, Asmita; COLE, Bridget, M.; (149 pag.)WO2017/117239; (2017); A1;,
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Synthetic Route of 6276-54-6, A common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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.

An aqueous sodium dicarbonate solution (3.5 g in 57 ml of water) and solid sodium chloride (7.5 g) were added at 0 C. to a suspension of 3-chloropropylamine hydrochloride (38 mmol) in DCM (77 ml), and the mixture was stirred for 30 minutes. A solution of Boc anhydride (1.2 eq.) in dichloromethane (20 ml) was then slowly added dropwise. The reaction mixture was stirred overnight at RT. The reaction mixture was extracted with dichloromethane, and the org. phase was washed with water and sat. sodium chloride solution, dried over sodium sulfate (anhydrous) and concentrated. The desired product was used in the next stage without being purified further.Yield: 83.7%

The synthetic route of 6276-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; US2010/222324; (2010); A1;,
Chloride – Wikipedia,
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Related Products of 1303587-99-6,Some common heterocyclic compound, 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, molecular formula is C6H6ClN3O, 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.

Synthesis of2-chloro-8-(2-(trifluoromethyl) benzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0458] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 0.87 mmol) in DMF (3 mL) under argon atmosphere were added sodium hydride (42 mg, 1.75 mmol) portion- wise for 5 min then l-(bromomethyl)-2-(trifluoromethyl) benzene (251 mg, 1.05 mmol) at 0 C. The reaction mixture was stirred for 1 h at 0 C. After consumption of the starting materials (monitored by TLC), the reaction was diluted with cold water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was washed with n-pentane (2 x 5 mL) to afford 2-chloro-8-(2-(trifluoromethyl) benzyl)-7, 8-dihydro-6H- pyrimido [5, 4-b] [1, 4] oxazine (160 mg, 55%) as an off-white solid. 1H-NMR (DMSO-<, 400 MHz): delta 7.79-7.77 (m, 2H), 7.65 (t, 1H), 7.52 (t, 1H), 7.40 (d, 1H), 4.95 (s, 2H), 4.29- 4.23 (m, 2H), 3.57-3.50 (m, 2H); LCMS: 329.8 (M+l); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.87 min. 0.05% Aq TFA: ACN; 0.80 mL/min); UPLC (purity): 92.4%; (column; Acquity UPLC BEH C-18 2.1 X 50 mm, 1.7 mupiiota); RT 2.57 min. ACN: 0.025% TFA (Aq); 0.50 mL/min; TLC: 30% EtOAc:hexanes (R 0.6). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, its application will become more common. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 51572-93-1, name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, 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 51572-93-1, Computed Properties of C7H8Cl3NO

General procedure: To a solution of 3ae3e (1 mmol) in anhydrous ethanol (10 mL),corresponding O-benzylhydroxylamine hydrochloride (1 mmol)and NaOAc (1.2 mmol) were added and the resulting solution wasstirred at the room temperate for 3 h. The mixture was concentratedand taken in ethyl acetate (20 mL), washed with water(20 mL), saturated sodium chloride solution (20 mL) and dried oversodium sulfate. The resulting solution was concentrated and thepurification of the residue by recrystallization from ethanol yieldedthe desired compounds 4a-4t

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; Lv, Xian-Hai; Li, Qing-Shan; Ren, Zi-Li; Chu, Ming-Jie; Sun, Jian; Zhang, Xin; Xing, Man; Zhu, Hai-Liang; Cao, Hai-Qun; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 586 – 593;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 326-64-7, These common heterocyclic compound, 326-64-7, name is 5-Chloro-2-(trifluoromethoxy)aniline, 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.

To a suspension of 5-chloro-2- ( trifluorometnyl ) aniline (5.00 g, 23.6 mmol) and dibenzyl disulfide (4.66g, 18.9 mmol) in acetonitrile (75 mL) , Isoamyl nitrite (3.46 mL, 26.0 mmol) was slowly added at 60C in an oil bath, and the mixture was stirred at the same temperature as above for 2 hours. The reaction mixture was cooled and then concentrated under reduced pressure, and the residue was purified in an automatic chromatography apparatus (n-hexane/ethyl acetate = 100/0 – 95/5) to prepare 2- (benzylsulfanyl ) -4-chlorophenyl trifluoromethyl ether (3.86 g, yield: 51%) . To a mixture of the obtained 2- (benzylsulfanyl ) -4-chlorophenyl trifluoromethyl ether (4.84 g, 15.2 mmol), acetic acid(4.5 mL) and water (3 mL) in acetonitrile (120 mL) , 1, 3-dichloro-5, 5-dimethylhydantoin (5.98 g, 30.4 mmol) was added under ice cooling, and the mixture was stirred at the same temperature as above for 3 hours. The mixture was diluted by addition of a saturated aqueous solution of sodium bicarbonate, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus(hexane/ethyl acetate = 100/0 – 85/15) to obtain the title compound (3.64 g, yield: 81%) . NMR spectrum (CDC13, 400MHz) delta: 8.09 (1H, d, J =2.3 Hz), 7.75 (1H, dd, J = 9.0, 2.7 Hz), 7.50-7.47 (1H, m) .

Statistics shows that 5-Chloro-2-(trifluoromethoxy)aniline is playing an increasingly important role. we look forward to future research findings about 326-64-7.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; MIYAZAKI, Shojiro; YAMAMOTO, Yuko; SUZUKI, Keisuke; INUI, Masaharu; IZUMI, Masanori; SOMA, Kaori; PINKERTON, Anthony; SHINOZAKI, Taeko; (243 pag.)WO2017/7943; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2106-02-7, 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. 2106-02-7, name is 2-Chloro-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

Method FA mixture of the relevant substituted pyrazole-3-carboxylic acid (intermediate TV or IX5 1.0 mmol) and SOCl2 (10 mL) was stirred at 80 0C for 18 h. After cooling to rt the mixture was concentrated and the residue dried in vacuo. A mixture of the relevant arylamine (1.0 mmol), DMAP (12 mg, 0.10 mmol), DMF (0.5 mL) and pyridine (1 mL) was added. The mixture was stirred at 80 C for 21 h and concentrated in vacuo. The residue was purified by chromatography (EtO Ac/heptane).

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

Reference:
Patent; BIOLIPOX AB; WO2007/45868; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 3972-56-3, 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. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To 25 g of 4-tert-butylchlorobenzene synthesised in (1) above were added 20 g of sulfuryl chloride and a catalytic amount of benzoyl peroxide, and the temperature was elevated and the mixture was maintained at 100¡ã C. for 1 hour. Then, the mixture was distilled under reduced pressure to give 17.0 g of 2-(4-chlorophenyl)-2-methyl-1-chloropropane (bp.: 121¡ã-123¡ã C./10 mmHg).

The synthetic route of 1-tert-Butyl-4-chlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsuitoatsu Chemicals, Inc.; US4599362; (1986); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 886762-39-6, These common heterocyclic compound, 886762-39-6, name is 3,4-Dichloro-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.

Step 1 Synthesis of Compound 11Will DCl (0.84mL, 12M,)Add to 3,4-dichloro-2-fluoroaniline (1.8g) in D2O (25mL)In the solution, the reaction was stirred at 180 C for 60 min under microwave. Cool to room temperature, adjust pH to basic with saturated sodium bicarbonate solution, dichloromethane (50 mL x 3).The organic layer was washed with saturated brine.Dry over anhydrous sodium sulfate,filter,The filtrate was concentrated under reduced pressure to give a brown solid1.8g.

The synthetic route of 886762-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Ren Xingye; (37 pag.)CN110054613; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 69695-61-0, name is 2-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 69695-61-0, Safety of 2-Chloro-4-(trifluoromethoxy)aniline

Example 98: A mixture of N-[l-(6-bromonaphthalen-2-yl)ethyl]acetamide (80 mg, 0.274 mmol), 2-chloro-4-trifluoromethoxyphenylamine (69.5 mg, 0.330 mmol), potassium tert- butoxide (43 mg, 0.384 mmol), BINAP (1.28 mg, 0.002 mmol), and 20 ml of toluene was flushed with nitrogen for 10 minutes, and then tris(dibenzylidineacetone)dipalladium(0) (0.63 mg, 0.00068 mmol) was added. The mixture was heated at 120 0C for 15 h, cooled, and concentrated under reduced pressure. The residue was taken into EtOAc, washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude material was purified by preparative TLC to afford N-{l-[6-(4- trifluo romethoxyphenylamino)naphthalen-2-yl] ethyl} acetamide as a brown sticky solid. LC/MS [M+H] 389.2. 1H-NMR (400MHz, DMSOd6) delta 8.524 (bs, IH), 8.264-8.281 (d, IH, J=6.8 Hz), 7.740-7.762 (d, IH, J=8.8 Hz), 7.649-7.670 (d, IH, J=8.4 Hz), 7.616 (s, IH), 7.458 (s, IH), 7.336-7.357 (d, IH, J=8.4 Hz), 7.184-7.224 (m, 4H), 4.973-5.007 (m, IH), 1.831 (s, 3H), 1.373-1.390 (d, 3H, J=6.8 Hz) ppm.

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

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala Kumara, Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; TIWARI, Atul; REDDY, Vantaddu, Nagarjuna; BISCHOFF, Alexander; WO2010/127208; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics