Tag: M.W=200-300

Electric Literature of 89794-02-5, These common heterocyclic compound, 89794-02-5, name is 4-Bromo-2-chlorotoluene, 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: 10.0 mmol of the specified boronic ester (I; R1), 30.0 mmol of magnesium turnings and 10.0 mmol of the salt (II) were suspended in a mixture of 3.40 g of anhydrous toluene and 0.73 g of anhydrous tetrahydrofuran in a dry four-neck flask with a mechanical stirrer, thermometer, metal condenser and pressure-equalized dropping funnel under a nitrogen atmosphere, and stirred vigorously for 30 min. The appropriate haloaromatic (III, R4) was added to this solution, at first in undiluted form, until the onset of exothermicity signals the start of the reaction. The remaining total amount of 30.6 mmol of haloaromatic was diluted with 10.0 g of anhydrous toluene and 10.0 g of anhydrous tetrahydrofuran and added dropwise at such a rate that the internal temperature does not exceed 45 C. On completion of addition, the reaction mixture was heated at reflux for 1 h or until the dissolution of the magnesium was complete. The resulting suspension was discharged onto 50 g of ice-water, and the resulting solids are isolated, washed with cold water and dried under reduced pressure. Examples 15, 18, 20 and 27 and 46-52 were extracted from the aqueous phase with 100 ml of ethyl acetate, the solvent was distilled off under reduced pressure and the resulting oils were isolated. The isolated yield for Example 1 that was prepared by this method was 2.87 g (72% of theory), whereas Example 1 prepared according to DE 198 50 139 A1 was obtained in a yield of 47% of theory.The composition of Examples 1-76 and selected physical properties are summarized in Table 2.

The synthetic route of 89794-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Covestro Deutschland AG; ROeLLE, Thomas; BERNETH, Horst; HOeNEL, Dennis; BRUDER, Friedrich-Karl; (34 pag.)US2019/276479; (2019); A1;,
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. 85462-59-5, name is 2-Bromo-5-chloro-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Bromo-5-chloro-4-fluoroaniline

To a solution of compound 56a (5 g, 22.28 mmol) in DMF (50 mL) was added Pd (PPh3) 2Cl 2 (1.0 g, 1.42 mmol) and compound 47b (8.85 g, 24.5 mmol) under nitrogen. The mixture was stirred at 100C under nitrogen for 12h, then cooled to room temperature, aqueous HCl (6 M, 8 mL) was added to the mixture and stirred at 25C for additional 3h. The mixture was diluted with water (250 mL) and extracted with ethyl acetate (200 mL 3). The combined organic layers were washed with water (300 mL), dried over sodium sulfate, filtered and concentrated in vacuum to give the crude product, which was purified by column chromatography on silica gel (0 to 10%EtOAc in PE (v/v)) to afford compound 56b (1.89 g, 45% yield). LCMS: R t = 2.071 min in 10-80AB_4min_220&254 chromatography (Xtimate C18 2.1*30mm), MS (ESI) m/z = 187.9 [M+H] +. 1H NMR (400MHz, CDCl 3) delta 7.39 (d, J = 10.0 Hz, 1H), 6.65 (d, J = 4.0 Hz, 1H), 2.47 (s, 3H).

According to the analysis of related databases, 85462-59-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, 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 50594-82-6, Computed Properties of C7H2Cl3F3

0.5 mol (124.7 g) of an 80:20 isomeric mixture consisting of 3,4,5-trichlorobenzotrifluoride and 2,4,5-trichlorobenzotrifluoride and 1.8 mol (178 g) of N-methylpyrrolidone are introduced into an autoclave. The autoclave is cooled to 0C and charged with 4 mol of ammonia (68 g) and heated with vigorous stirring to 190C for 8 hours. After cooling and removal of excess ammonia, the reaction mixture is filtered off from the ammonium chloride produced and the liquid phase is vacuum distilled. The distillation yields 88.3 g of an azeotropic mixture containing 83% 2,6-dichloro-4-trifluoromethylaniline (2,6-DC-pTFMA) and 17% N-methylpyrrolidone. The 99% pure product is precipitated out from the azeotropic mixture by addition of water and, after filtration and drying, 0.317 mol (73 g) of 2,6-dichloro-4-trifluoromethylaniline (yield 79.2% relative to 3,4,5-TCBTF) are obtained. Examples 2 and 3 below are given in order to illustrate the advantage of keeping the conversion of 3,4-DCBTC into 3,4,5-TCBTC at a low level in the chlorination stage, in that if conversion of the 3,4-DCBTC is boosted, the result is not a greater yield of 3,4,5-TCBTC, but instead the formation of isomeric and polychlorinated products which require costly disposal

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, 3,4,5-Trichlorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FINCHIMICA S.p.A.; EP1528052; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 62356-27-8, 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. 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 175 6-(3-chloro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 275, structure 4 of Scheme II, where R1 =3-chloro-2-methylphenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (70.0 mg, 0.22 mmol) and 2-bromo-6-chlorotoluene (45.2 mg, 0.22 mmol). The crude material was purified by flash column chromatography (75 ml silica, hexane to 5% ethyl acetate/hexane) to afford 63.1 mg (96%) of Compound 275. Data for Compound 275: 1 H NMR (400 MHz, acetone-d6) 7.30 (d, J=8.3, 1H), 7.16 (m, 1H), 6.95 (s, 1H), 6.87 (d, J=10.2, 1H), 6.54 (d, J=8.0, 1H), 5.36 (s, 1H), 5.25 (s, 1H), 2.03 (s, 3H), 1.28 (s, 6H).

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-3-chloro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
Chloride – Wikipedia,
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Electric Literature of 2770-11-8,Some common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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-(4-Chlorophenoxy)aniline (25 mg, 0.1138 mmol, 1.1 eq) and l-acetyl-7V-(2- acetylphenyl)piperidine-4-carboxamide (30 mg, 0.1040 mmol, 1 eq) were stirred in dry dichloromethane (DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (55 muL, 0.2303 mmol, 2.2 eq) was added to the reaction mixture which was stirred at room temperature for an additional 10 min. Sodium triacetoxyborohydride (110 mg, 0.5190 mmol, 5 eq) and acetic acid (3 drops) were added to the reaction mixture which was stirred at room temperature for 16 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (50 mL) and extracted with DCM (30 mL). The organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 100% petroleum ether (PE) to 100% EtOAc] gave the title compound (5 mg, 10%) as a clear oil.1H NMR (270 MHz, CDCl3) delta 1.44 (3H, d, J = 7.5 Hz, CH3), 1.63-1.68 (2H, m, CH2), 1.82-1.98 (2H, m, CH2), 2.02 (3H, s, CH3), 2.38-2.45 (IH, m, CH), 2.65-2.69 (2H, m, CH2), 3.09-3.21 (2H, m, CH2), 4.40-4.48 (2H, m, CH + NH), 6.40-6.44 (IH, m, ArH), 6.51-6.58 (IH, m, ArH), 6.74-6.95 (4H, m, ArH), 7.05-7.11 (IH, m, ArH), 7.19-7.22 (3H, m, ArH), 7.35-7.49 (3H, m, NH + ArH); 13C NMR (67.5 MHz, CDCl3) delta 21.6, 25.2, 41.0, 45.8, 53.2, 60.5, 113.0, 117.0, 117.1, 118.6, 118.8, 119.2, 119.3, 119.4, 119.6, 125.3, 129.5, 129.7, 129.8, 139.4, 142.6, 146.3, 168.5, 172.3; LCMS (90% MeOH and 10% H2O; Symmetry Ci8 reverse phase column) tr = 2.38 min; (ES”), m/z 492 (35ClM”, 75%), 494 (37ClM”, 25%); HRMS (ESI) calcd. for C28H31ClN3O3 (M+H)+ 492.2048, found 492.2038.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Chlorophenoxy)aniline, its application will become more common.

Reference:
Patent; STERIX LIMITED; WO2009/66072; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 699-89-8, The chemical industry reduces the impact on the environment during synthesis 699-89-8, name is 4,7-Dichlorothieno[2,3-d]pyridazine, I believe this compound will play a more active role in future production and life.

To the dichloride from Example 8, step 4 (1.00 g, 4.90 mmol) was added p-chloroaniline (622 mg, 4.90 mmol) and absolute ethyl alcohol (10.0 mL). The mixture was refluxed at 95 C. for 2 hrs and then cooled to room temperature. The yellow precipitate (2) that formed was filtered and washed with isopropyl alcohol, 4.0 N KOH, H2O, and then hexane. The filtrate (2) was then mixed 6-aminobenzothiazole (883 mg, 5.88 mmol) in 10 mL of n-butanol, and heated at 150 C. overnight. The reaction was allowed to cool to room temperature before the solvent was removed by rotary evaporation. The residue was treated sequentially with aqueous 4.0 N KOH solution and extracted with dichloromethane (50 mL), dried (MgSO4), and the solvent evaporated. The crude product was purified by flash chromatography on silica gel using 95% dichloromethane/methanol as the eluent. The structure of the pure title compound was confirmed by LC/MS and NMR: TLC (30% EtOAc/Hexanes) Rf (3)=0.20; 1H NMR (DMSO) ? 7.2 (dd, 3H), 7.38 (dd, 3H), 7.65 (d, 1H), 8.0 (d, 1H), 8.45 (d, 1H), 8.8 (s, 1H); LC/MS m/z 410 rt=4.21 min.

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, 4,7-Dichlorothieno[2,3-d]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US6689883; (2004); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 54932-72-8, A common heterocyclic compound, 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, molecular formula is C7H6BrCl, 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 solution of 4.1 g (20 mmol) of 5-bromo-2-chlorotoluene, 0.66 g (4 mmol) of 2,2-azobisisobutyronitrile, 3.9 g (22 mmol) of N-bromosuccinimide and 20 ml of chloroform Dry two bottles, reflux 5h.(100 ml), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was recrystallized from ethanol to give 4.1 g of needle-like crystals (100 ml), washed with water (100 ml) (Yield 72%).

The synthetic route of 54932-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; XUE, XIAO WEN; LIU, LIN YI; LONG, JIN JIE; SONG, YA JING; LI, JIA BIN; (7 pag.)CN104478670; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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 1996-29-8, Formula: C6H3BrClF

Synthesis 32; 4-Chloro-2-fluorophenyIboronic acid; 1-Bromo, 4-chloro, 2-fluorobenzene (5 g) was dissolved in anhydrous THF (50 ml). Excess Mg turnings (freshly oven dried) were added and the mixture gently heated under an atmosphere of nitrogen, until a self-sustaining reaction commenced. The reaction remained at reflux for a further 10 mins, and was then gently boiled with external heating for a further 10 min. The mixture was allowed to cool to room temp, giving a Grignard of about 0.5 M solution.The solution was transferred to a separate vessel, a further 20 ml THF added and placed under an atmosphere of nitrogen. The solution was cooled in an ethanol / CO2 bath to below -40 C and triisopropyl borate (14 ml) added via a syringe. The mixture was allowed to slowly warm to 0 C and then stirred in an ice bath for a further hour. The reaction was quenched with sat. NH4CI, extracted with ether and the organic washed with 10 % HCI and dried (Na2SO4). Evaporation gave a waxy yellow solid. Purification by column chromatography gave the title compound as a waxy solid. The solid was dissolved in ether and recrystallised with addition of petrol and slow evaporation of the ether. Further recrystallisation by this method gave the pure product as a fluffy white powder.

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; THE UNIVERSITY COURT OF THE UNIVERSITY OF ABERDEEN; WO2008/114022; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Taking cytisine as a reactant,Using triethylamine as a catalyst,In a mixture of organic solvent benzene and acetonitrileSulfonylation of 2,4-dimethoxybenzenesulfonyl chloride,Among them, cytisine,The molar ratio of 2,4-dimethoxybenzenesulfonyl chloride to the catalyst is 15:20:20,The organic solvent is added in an amount of 100 times the number of moles of cytisine.The cytisine derivative can be obtained;After the sulfonylation reaction,After distillation under reduced pressure, a crude cytisine derivative is obtained.Then the crude cytisine derivative is used in a volume ratio of 30:11:1.The chloroform and methanol elution system can be separated by silica gel column chromatography to obtain high purity.N-2,4-dimethoxybenzenesulfonyl-cytisine.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Guangxi Tianyuan Biochemical Co., Ltd.; Li Weiguo; Liu Yingqian; Yang Chengjie; Ling Chunhua; Li Juncai; Chen Cheng; Zhang Junxiang; (29 pag.)CN108503640; (2018); A;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, 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 13918-92-8, HPLC of Formula: C6H3ClF2O2S

To a suspension of 5-bromo-2-methoxypyridin-3-amine (6.3 g, 31 mmol) in pyridine (25 mL) was added 2,4-difluorobenzene-1-sulfonyl chloride (16.47 g, 77.5 mmol). The reactionwas stirred at 23C for 24 h. The solvent volume was then reduced to 50% under reduced pressure. The resulted solid was collected by filtration, and was washed with i-PrOH (5 mL x 2)followed by Et20 (5 mL). A suspension of the above solid and NaOH (2.48 g, 62 mmol) inMeOH (25 mL) was stirred at 23C for 1 h and then concentrated in vacuo. The residue wasdiluted with DCM (20 mL) and 2M HCl (20 mL), adjusted to pH 7 with 5% aq. NaHC03, andthen extracted with DCM (20 mL x 3). The combined organic phases were washed with brine (20mL), dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound as apale yellow solid (8.2 g, 69.9%). The title compound was characterized by LC-MS and 1HNMR as shown below:LC-MS (ESI, pos. ion) m/z: 379 [M+Ht;1HNMR (400 MHz, CDCh) 8 (ppm): 3.89 (s, 3H), 6.90-7.01 (m, 2H), 7.80-7.83 (d, J= 2.24 Hz,1H), 7.86-7.93(m, 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; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Zhuo; WANG, Tingjin; WU, Zuping; WEN, Qiuling; WO2014/22128; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics