Tag: M.W=200-300

81927-55-1, These common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, 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.

A stirred solution of (R)- methyl 3-hydroxy-2-methylpropanoate (9.57 g, 81.0 mmol) and benzyl 2,2,2- trichloroacetimidate (22.50 g, 89.1 mmol) in CH2Cl2 (10 mL) was cooled to 0 0C under N2. Triflic acid (0.1 mL) in CH2Cl2 (1 mL) was added dropwise. After 10 minutes the reaction became a solid mass. After 1 hour, saturated aqueous NaHCO3 was added and the mixture extracted with Et2O. The organics were dried over MgSO4, filtered and concentrated on a rotary evaporator. Hexane was added and the resulting solids collected by vacuum filtration. The filtrate was concentrated on a rotary evaporator and purified using flash chromatography (5-10% EtOAc/hexane) to give 10.39 g (62%) of (R)-methyl 3-(benzyloxy)-2- methylpropanoate as a colorless oil. Rf= 0.20 (10% EtOAc/hexane). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.08 (d, J=7.14 Hz, 3 H) 2.75 (ddd, J=14.01, 12.64, 7.14 Hz, 1 H) 3.44 – 3.59 (m, 2 H) 3.60 (s, 3 H) 4.46 (s, 2 H) 7.23 – 7.40 (m, 5 H).

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 81927-55-1.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

41965-95-1, A common compound: 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A mixture of 4 (0.12 mmol), 3~ehoro-4-methoxyhenzylamine hydrochloride (0.12 mmol), Nal (0.006 mmol), and phenol (0.12 mmol) was heated at 130 “C for 2.5 h. The reaction mixture was diluted with Et20 ( 10 mL) and washed with IN NaOH (3×5 mL). The organic layer was dried over Na2S0 , filtered and evaporated under reduced pressure. The residue was purified by Flash Chromatography (AcOEt: MeOH 8:2) to give the desired compound B (33% of yield). MS ESI (m/z) 394 (M+ j ), H NMR (300 MHz, CDCI3) delta 8.32 (d, 1 H, J= 1.2 Hz), 7.97 (d, 1H, J= 8.7 Hz), 7.71 (dd, 1H, J,= 1 .8, J2= 8.7 Hz), 7.37 (d, 1H, J= 2.1 Hz), 7.18 (dd, 1H, Jx= 2.4, J2= 8.7 Hz), 6.94 (d, 1H, J- 8.4 Hz), 4.57 (d, 2H, J= 6.0 Hz), 4.1 1 (br s, 1H), 3.92 (s, 3H), 3.54 (s, 2H), 3.22 (t, 2H, J= 6.3 Hz), 2.83 (t, 2H, J= 6.3 Hz), 2.52 (s, 3H).

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-methoxybenzylamine Hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; ARANCIO, Ottavio; FIORITO, Joie; WASMUTH, Andrew; WO2013/109738; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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.

Compound 10H- spiro [fluorene-9,9′ acridine] (16.55g, 50mmol)And 4-bromo-2-chloro-1-fluorobenzene (10.50g, 50mmol)Add in a three-necked flask,Stir and dissolve with 200 mL of N,N-dimethylformamide (DMF).Nitrogen protection,Then add Cs2CO3 (19.5g, 60mmol)And K2CO3.The reaction solution was stirred and refluxed for 12 hours.After cooling, the reaction solution was poured into 1000 mL of water, and 2 filtered, and the filter cake was washed with a mixed solvent of ethanol and petroleum ether, and suction filtered.The filter cake was recrystallized from a mixed solvent of dichloromethane and petroleum ether (DCM/PE).The compound 1-1 (16.09 g, yield 62%) was obtained as a white solid.

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 60811-21-4.

Reference:
Patent; Guangzhou Huarui Optoelectric Materials Co., Ltd.; Yang Xi; Pan Junyou; Wang Pu; (50 pag.)CN109651369; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13526-66-4 name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate Q6-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine A mixture of 4.18 g (18 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine, 2.95 g (18.9 mmol) of 3-chlorophenylbronic acid, 0.83 g (0.72 mmol) of tetrakis(triphenylphosphine)palladium (0) and 32.3 ml of 2 M aqueous sodium carbonate solution are heated to boiling under in 188 ml of 1,4-dioxane for 12 h.The reaction mixture obtained in this way is mixed with sat. aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with sat. aqueous sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off. In the final purification by chromatography on silica gel, 3.46 g (73%) of the desired product were isolated.1H-NMR (DMSO-D6): delta=7.43 (d, 1H); 7.44 (dd, 1H); 7.53 (t, 1H); 8.05 (dt, 1H); 8.16 (t, 1H); 8.29 (d, 1H); 8.38 (s, 1H) ppm.MS (ESI+): m/z=264 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; PRIEN, Olaf; Eis, Knut; Bader, Benjamin; Guenther, Judith; Von Bonin, Arne; US2009/93475; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

3386-33-2, Adding a certain compound to certain chemical reactions, such as: 3386-33-2, name is 1-Chlorooctadecane, 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 3386-33-2.

Diallylphenol (3.48 gm, 0.02 mol) was diluted in dimethyl sulfoxide (50 ml) and sodium hydroxide (0.8 gm, 0.02 mol) added to the solution followed by 1-chlorooctadecane (5.78 gm, 0.02 mol) and heated at 80 C. for 2 hrs. After cooling and diluting with water, the reaction mixture was extracted with hexane, dried over MgSO4 filtered and evaporated to give the desired product. MS m/z 426. (M+ calcd for C30H50O=426). H NMR (300 MHz, CDCl3) d 0.80 (t ,3, CH3), 1.25 (s, 32, CH2).1.75-1.80 (m, 2, CH2), 3.30-3.40 (d, 4, CH2), 3.70-3.80 (t, 2, OCH2), 5.05-5.21(m, 2, CH2 vinyl), 5.95-6.10 (m, 2,CH2 vinyl), 7.00-7.20(m, 3, aromatic). Oxidation with MCPBA as described in Example 1 gave 2,6-di(epoxypropyl)phenyl octadecyl ether. MS m/z 458 (M+ calcd for C30H50O3=458). H NMR (300 MHz, CDCl3) d 0.80 (t, 3, CH3), 1.25 (s, 30, CH2), 2.60-2.70 (m, 2, CH2 epoxypropyl), 2.75-3.10 (m, 6, CH2 epoxypropyl), 3.20-3.30 (m, 2, epoxypropyl CH), 3.55-3.75 (t, 2, CH2), 7.10-7.25 (m, 1, aromatic), 7.40-7.60 (m, 2, aromatic).

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, 1-Chlorooctadecane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pews, R. Garth; US2005/90673; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

This experiment was carried out in two batches of the same scale. n-Butyllithium (2.5 M solution in hexanes; 32.8 mL, 82.0 mmol) was slowly added to a -70 C. solution of 1-bromo-4-chloro-2-fluorobenzene (17.2 g, 82.1 mmol) in diethyl ether (100 mL), while the temperature of the reaction mixture was maintained below -60 C. After the reaction mixture had been stirred at -70 C. for 20 minutes, a solution of 3-bromo-2-hydroxybenzaldehyde (5.5 g, 27 mmol) in diethyl ether (100 mL) was slowly added, while the reaction temperature was maintained below -60 C. After a further 1 hour of stirring at -70 C., the reaction was quenched by addition of aqueous ammonium chloride solution (50 mL) at -70 C., and the resulting mixture was diluted with water (100 mL). The two batches were combined at this point and extracted with ethyl acetate (400 mL); the organic layer was washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 7% ethyl acetate in petroleum ether) afforded C1 as a white solid. Combined yield: 15.7 g, 47.4 mmol, 88%. 1H NMR (400 MHz, chloroform-d) delta 7.44 (dd, J=8.0, 1.5 Hz, 1H), 7.37 (dd, J=8.1, 8.1 Hz, 1H), 7.15 (br dd, J=8.5, 2.1 Hz, 1H), 7.12-7.05 (m, 2H), 6.80 (dd, J=7.8, 7.8 Hz, 1H), 6.78 (s, 1H), 6.31 (d, J=4.8 Hz, 1H), 3.02 (brd, J=4.9 Hz, 1H).

The synthetic route of 1-Bromo-4-chloro-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Aspnes, Gary Erik; Bagley, Scott W.; Curto, John M.; Edmonds, David James; Flanagan, Mark E.; Futatsugi, Kentaro; Griffith, David A.; Huard, Kim; Lian, Yajing; Limberakis, Chris; Londregan, Allyn T.; Mathiowetz, Alan M.; Piotrowski, David W.; Ruggeri, Roger B.; (127 pag.)US2019/382384; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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 202197-26-0. 202197-26-0

Example 17 O-{4-[-3-chloro-4-(3-fluorobenzyloxy)-phenylamino]-quinazolin-6-yl}-acetate 6-acetoxy-4-chloroquinazoline (0.90 g, 4.04 mmol) and 3-chloro-4-(m-fluoro-benzyloxy)-aniline (1.00 g, 3.97 mmol) were dissolved into 40 mL of isopropanol, and the mixture was stirred under reflux for 3 h. A lot of light grey solid was deposited, which was filtered, and the filter cake was washed with small quantity of ethyl acetate and dried under vacuum at 60 C. overnight to obtain the title compound (1.65 g, 95%). 1H-NMR (400 MHz, CDCl3): delta8.68(1H, s), 7.89-7.81 (2H, m), 7.58-7.48 (2H, m), 7.40-7.32 (1H, m), 7.27-7.19 (3H, m), 7.16 (1H, d, J=2.46 Hz), 7.07-6.96 (2H, m), 5.14 (2H, s), 2.11 (3H, s).

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 3-Chloro-4-((3-fluorobenzyl)oxy)aniline.

Reference:
Patent; SHANGHAI ALLIST PHARMACEUTICALS, INC.; US2008/300248; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

202197-26-0, 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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1; Preparation of GW572016F; STAGE 1; A stirred suspension of 3H-6-iodoquinazolin-4-one (compound A) in toluene (5 vols) was treated with tri-n-butylamine (1.2 eq.) at 20 to 25C, then heated to 900C. Phosphorous oxychloride (1.1 eq) was added, the reaction mixture was then heated to reflux. The reaction mixture was cooled to 500C and toluene (5vols) added. Compound C (1.03 eq.) was added as a solid, the slurry was warmed back to 900C and stirred for 1 hour. The slurry was transferred to a second vessel; the first vessel was rinsed with toluene (2vol) and combined with the reaction mixture. The reaction mixture was cooled to 700C and 1.0 M aqueous sodium hydroxide solution (16 vols) added dropwise over 1 hour to the stirred slurry maintaining the contents temperature between 68-72C. The mixture was stirred at 65-700C for 1 hour and then cooled to 200C over 1 hour. The suspension was stirred at 200C for 2 hours, the product collected by filtration, and washed successively with water (3 x 5 vols) and ethanol (IMS, 2 x 5 vols), then dried in vacuo at 50-600C. Volumes are quoted with respect of the quantity of Compound A used. Percent yield range observed: 90 to 95% as white or yellow crystals.

The synthetic route of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM (CORK) LIMITED; WO2008/67144; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

56961-77-4, A common compound: 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

After dissolving 10 g (44 mmol) of 1-bromo-2,3-dichlorobenzene [1-bromo-2,3-dichlorobenzene] in 100 mL of toluene, diphenylamine (2.1eq, 92mmol), sodium t-butok Side [sodium t-butoxide] (2.7eq, 120mmol), BTP (Bis (tri-tert-butylphosphine) palladium (0)) (10mol%) was added and stirred under reflux for 3 hours to prepare intermediate 2 (2-chloro-N1, N1, N3, N3-tetraphenylbenzene-1,3-diamine) was synthesized. The obtained intermediate 2 was purified by column chromatography.Intermediate 2: m / z = 446.15 (C30H23ClN2)Yield = 15g (75.8%), Purity = 99.5%

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, 1-Bromo-2,3-dichlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG Chem, Ltd.; Lee Gi-gon; Seo Sang-deok; Keum Su-jeong; Kim Myeong-gon; Kim Gyeong-hui; Lee Dong-hun; Park Tae-yun; Kim Dong-heon; Lee U-cheol; (46 pag.)KR2020/4248; (2020); A;,
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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., 6579-54-0

b 2,6-dichlorobenzenesulfonamide A solution of 2,6-dichlorobenzenesulfonyl chloride (10.50 g, 42.77 mmol) in 100 mL of pyridine was added into 100 mL of pyridine dropwise while anhydrous ammonia gas was passing through the solution simultaneously for 4 hours at 0 C. The mixture was acidified to pH>1 with 6N aq. HCl, then extracted with ethyl acetate. The combined organic layer was then dried (Na2SO4) and concentrated to give the desired product (8.69 g, 90%). EI-MS (m/z) 225.0, 227.1 (M-).

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; Widdowson, Katherine Louisa; Jin, Qi; US2003/65170; (2003); A1;; ; Patent; Widdowson, Katherine Louisa; Jin, Qi; US2003/65188; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics