Author: Jessica.F

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

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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

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H9ClO2

5-dimethoxybenzene (10.0 g, 58 mmol) and N-bromosuccinimide (10.3 g, 58 mmol)Is dissolved in 1,2-diethylene chloride (200 ml) and stirred at room temperature for 24 hours.After completion of the reaction, the solvent was removed from the reaction solution through a rotary evaporator, followed by extraction with methylene chloride / distilled water, followed by column chromatography using a developing solvent of methylene chloride / hexane as a developing solvent to obtain 13.3 g of Intermediate 1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7051-16-3.

Reference:
Patent; LG Chem, Ltd.; Dankook University Cheonan Campus Industry-Academic Cooperation Foundation; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Kim Gong-gyeom; Lee U-cheol; Lee Chil-won; Cha Jae-ryeong; Joo Yun-seok; (30 pag.)KR2018/106234; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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.

To a DMF (7.0 mL) solution of N-Boc-p-toluenesulfonamide (1.00 g, 3.69 mmol) was added 60% sodium hydride (0.22 g, 5.53 mmol) at 0 C. The reaction mixture was stirred for 15 min at room temperature. To the mixture at 0 C were added cinnamyl chloride (0.675 g, 4.42 mmol) and 15-crown-5-ether (0.22 g, 3.69 mmol) at 0 C. The mixture was stirred for 12 h and poured into water (50 mL). The S19 organic layer was separated and the aqueous layer was extracted with AcOEt. The combined organic layer was washed with H2O (50 mL 2) and dried over MgSO4. The solvent was removed under reduced pressure. The residue was precipitated from n-hexane and filtered off to give the titled compound (1.35 g, 95%) as white powders.

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

Reference:
Article; Go, Takashi; Morimatsu, Akane; Wasada, Hiroaki; Tanabe, Genzoh; Muraoka, Osamu; Sawada, Yoshiharu; Yoshimatsu, Mitsuhiro; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2722 – 2729;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 108047-39-8, name is 2-(Aminomethyl)-4-chloroaniline, 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 108047-39-8, Safety of 2-(Aminomethyl)-4-chloroaniline

A solution of the amine of preparation 10 (4.12 g, 26 MMOL) in tetrahydrofuran (50 mi) was added to a solution of the oxadiazole of preparation 6 (2.95 g, 11 MMOL) in tetrahydrofuran (50 ml) and heated to 50 C for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue purified by chromatography on silica gel using ethyl acetate as eluant to give the title compound as an off-white solid (2.34 g). APCI MS M/Z 400 [MH] H NMR (400MHZ, CDCI3) : 5 1.80 (m, 2H), 2.20 (m, 2H), 3.20 (m, 3H), 3.80 (s, 2H), 4.00 (s, 2H), 4.75 (m, 2H), 6.50 (t, 1H), 6.60 (d, 1H), 7.00 (d, 1H), 7.05 (d, 1H), 8.35 (d, 2H).

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:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/74291; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 50638-46-5, These common heterocyclic compound, 50638-46-5, name is 4-Bromo-3-chloroanisole, 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 solution of 1-bromo-2-chloro-4-methoxybenzene (6.6 g, 30 mmoL) in 1, 4-dioxane (150 mL) was added with 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (8 g, 30 mmol) , Pd (dppf)2Cl2(2.2 g, 3 mmol) and Cs2CO3(14.7 g, 45 mmol) and the mixture was heated at 90 overnight. After evaporated the solvent under reduced pressure, the residue was added with water (80 mL) , extracted with ethyl acetate (80 mL) . The organic layer was dried, concentrated and purified by column chromatography (PE: EA=80: 1) to give product as a white solid (6.2 g in 74%yield) .1H NMR (CDCl3) deltaH7.12 (d, J = 12.0 Hz, 1H) , 6.90 (d, J = 1.2 Hz, 1H) , 6.75 (dd, J1=8.0 Hz, J2=4.0 Hz, 1H) , 5.56-5.54 (m, 1H) , 4.04-4.01 (m, 4H) , 3.79 (s, 3H) , 2.55-2.51 (m, 2H) , 2.45-2.42 (m, 2H) , 1.89 (t, J = 6.4 Hz, 2H) . [M+H]+=281.1.

Statistics shows that 4-Bromo-3-chloroanisole is playing an increasingly important role. we look forward to future research findings about 50638-46-5.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4535-90-4, These common heterocyclic compound, 4535-90-4, name is 2-Chloro-N-methylethanamine 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.

EXAMPLE 3 1,1a,6,10b-Tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one O-[ 2-(methylamino)ethyl]oxime SPC12 A dispersion of 1.5 g of 40% sodium hydride in mineral oil (0.025 mole of NaH) was thoroughly washed with hexane. To the sodium hydride, a solution of 2.4 g (0.010 mole) of 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one oxime in 40 ml of dry hexamethylphosphoramide (HMPA) was added. The mixture was stirred at 25 for 1 hr under nitrogen. To the oxime salt was added 1.7 g (0.012 mole) of 2-methylaminoethylchloride hydrochloride and the mixture was stirred at 25 for 16 hrs. The reaction was processed as in Example 1 to give 2.5 g of an oil. Chromatography on 25 g of silica gel with ether as the eluent removed unreacted starting oxime. The crude product was obtained with methanol – 1% triethylamine as eluent. Flash distillation (0.1mu, 180 bath) of the methanol fractions gave 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one O-[ 2-(methylamino)ethyl]oxime, MP 100- 101C. NMR spectrum (CDCL3): multiplet at delta6.8-7.5 (8H), triplet (J=6 Hz) at 4.2 (2H), triplet (J=6 Hz) at 2.8 (2H), singlet at 2.4 superimposed on a multiplet at 2.1-2.5 (5H) and a multiplet at 1.3-1.8 (3H). Mass. spec: Calcd. for C19 H20 N2 O: 292.1575; Found: 292.1546.

The synthetic route of 4535-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. Du Pont de Nemours & Company; US3960956; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics