Tag: M.W=100-200

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. 87-63-8, name is 2-Chloro-6-methylaniline, A new synthetic method of this compound is introduced below., Product Details of 87-63-8

Ethyl vinyl ether compound of formula-5 (500 gm) was slowly added to oxalyl chloride compound of formula-4 (670 ml) at 10-15C. Raised the temperature of the reaction mixture to 25-30C and stirred for 12 hours at the same temperature. Heated the reaction mixture to 120- 125C and stirred for 90 minutes at the same temperature. Cooled the reaction mixture to 30-35 C and (E)-3-ethoxyacryloyl chloride compound of formula-7 was collected by fractional distillation. Added tetrahydrofuran (1160 ml) to the obtained compound of formula-7 and cooled the reaction mixture to 10-15C. Slowly added a solution of 2-methyl-6-chloroaniline compound of formula-9 (290 gm), pyridine (248ml) & tetrahydrofuran (1160 ml) to the reaction mixture at same temperature. Raised the temperature of the reaction mixture to 25-30C and stirred the reaction mixture for 4 hours at the same temperature. Cooled the reaction mixture to 5-10C and acidified the reaction mixture using aqueous HC1 solution. Water and ethyl acetate were added to the reaction mixture and stirred for 10 minutes. Separated the both aqueous & organic layers and extracted the aqueous layer with ethyl acetate. Washed the total organic layer with aqueous sodium bicarbonate solution followed by with water. Distilled off the solvent completely from the organic layer under reduced pressure. Ethyl acetate was added to the obtained compound at 25-30C and cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the precipitated solid, washed with chilled ethyl acetate and dried the material to get the title compound. Yield: 300 gm; M.R.: 160-164C; HPLC Purity: 99.66%.

The synthetic route of 87-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHUSUDHAN, Gutta; SEETHA RAMA SARMA, Peri; KHALIL AHAMED, Mogal; (38 pag.)WO2017/2131; (2017); A1;,
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Application of 348-65-2, 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. 348-65-2 name is 5-Chloro-2,4-difluoroaniline, 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.

In a 500 mL two-neck round-bottomed flask equipped with magnetic stirrer, 5-chloro-2,4-difluoroaniline (10 g,61 mmol, 1 eq) was dissolved in DCM (150 mL, HPLC grade). Then, prop-2-ynoic acid (5.5 g, 78 mmol, 1.3 eq) wasadded dropwise (the salt of the amine appeared). Next EDC·HCl (14 g, 78 mmol, 1.3 eq) was added in several portions(during the addition the reaction flask was cooled in an ice bath to maintain the room temperature. After full addition ofEDC·HCl, the reaction mixture was stirred for an additional 1 h at room temperature. After that time 150 ml of water wasadded and the mixture was transferred into a separatory funnel. The phases were separated. The water phase wasextracted twice with the DCM (2 x 100 mL). The organic fractions were combined, washed with brine, dried over MgSO4and concentrated to approximately 50 ml in vacuo, resulting a thick suspension. The solids were filtered and dried tofurnish 8 g of cream crystals. The filtrate was concentrated and then purified by flash chromatography (n-hexane/AcOEt;8:1 ? 5:1) giving additional 4.4 g of the amide C-6F. As a result, expected amide C-6F was obtained as a cream solid(12.4 g, 94 % yield, 100 % purity according to UPLCMS analysis).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2,4-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Adamed sp. z o.o.; FEDER, Marcin; MAZUR, Maria; KALINOWSKA, Iwona; JASZCZEWSKA, Joanna; LEWANDOWSKI, Wojciech; WITKOWSKI, Jakub; JELEN, Sabina; WOS-LATOSI, Katarzyna; (56 pag.)EP3511334; (2019); A1;,
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Related Products of 928-50-7,Some common heterocyclic compound, 928-50-7, name is 5-Chloropent-1-ene, molecular formula is C5H9Cl, 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.

In an oven-dried two-neck round-bottom flask equipped with a condenser and a magnetic stirrer were successively added oxime1b(193 mg, 0.92 mmol), xanthate20(75 mg, 0.46 mmol) and the desired chloroolefin21b(202 mg, 1.93 mmol) in benzene (5 mL). Argon was then bubbled directly into the flask for 30 min. (Bu3Sn)2(0.3 mL, 0.58 mmol) was then injected and the flask was heated to 60C. After 5min., DTBHN was added. After total consumption of the starting material, the resulting mixture was concentrated in vacuo and purified by silica gel chromatography (Petroleum ether/EtOAc 90-10->80:20) to afford the desired product22bas a yellow oil (63 mg, 52%).Rf = 0.32 (Petroleum ether/EtOAc90:10)IR (neat, NaCl)nmax(cm-1) 2953, 2247, 1453, 1378, 1248, 1144, 1089, 1004, 837.1H-NMR (300 MHz, CDCl3)delta(ppm) 7.23 (d,J= 7.5 Hz, 1 H), 5.04(s, 2 H), 3.63 (t,J= 8.3 Hz, 2 H), 3.50 (t,J= 6.4 Hz, 2 H), 2.47-2.27 (m, 3 H), 1.87-1.49 (m, 6 H), 0.90 (t,J= 8.3 Hz, 2 H), -0.02(s, 9 H).13C-NMR (75 MHz, CDCl3)delta(ppm) 152.6, 119.0, 96.7, 66.0, 44.9, 38.6, 29.6, 29.5, 28.1, 17.9, 14.9, -1.5.HRMS (ESI) calcd for C14H27ClN2O2SiNa [M+Na+]:341.1422,found:341.1431.

The synthetic route of 928-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Landais, Yannick; Robert, Frederic; Godineau, Edouard; Huet, Laurent; Likhite, Nachiket; Tetrahedron; vol. 69; 47; (2013); p. 10073 – 10080;,
Chloride – Wikipedia,
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Application of 1206825-03-7, 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. 1206825-03-7, name is 4-Chloroimidazo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 4: 3-((3R,4R)-3-(Imidazo[l,2^] [l,2,4]triazin-4-yl(methyl)amino)-4-methylpiperidin- l-yI)-3-oxopropanenitrile (34)34 To a solution of 4-chloroimidazo[l,2-/J[l,2,4]triazine (33) (0.23 mg, 1 mmol) and 3-((3i?,4i?)-4-methyl-3-(methylamino)piperidin-l-yl)-3-oxopropanenitrile (21) (0.15 g, 1 mmol) in dioxane water (3:8 mL) was added NaHCO3 (0.084 g, 1 mmol). The mixture was heated in a microwave at 100 0C for 30 min and concentrated in vacuum. The residue obtained was purified by flash column chromatography (silica gel 12 g, eluting with 0-20% CMA-80 in chloroform) to furnish 3-((3/?,4i?)-3-(Imidazo[ 1 ,2-/J [ 1 ,2,4]triazin-4-yl(methyl)amino)-4-methylpiperidin- 1 -yl)-3- oxopropanenitrile (34) (0.05 g, 16%) as an off-white solid; mp 72.0 0C. 1H NMR (300 MHz, DMSO) delta 8.11 (s, IH), 8.05 (s, IH), 7.62 (s, IH), 6.45-5.73 (m, IH), 4.08 (s, 2H), 3.87 (s, 3H), 3.40 (s, 3H), 2.47-2.34 (m, IH), 1.89-1.50 (m, 2H), 1.01 (s, 3H); MS 314.1 (100%, M+l, ES^).

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-Chloroimidazo[2,1-f][1,2,4]triazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; CHAND, Pooran; KOTIAN, Pravin, L.; KUMAR, V., Satish; WO2010/14930; (2010); A2;,
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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. 3260-88-6, name is 2-Methyl-3-chloroanisole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Methyl-3-chloroanisole

A mixture of Scheme 48 compound 1 (20.0 g, 128.0 mmol), N-bromo succnimide (26.1 g, 146.0 mmol) and AIBN (210 mg, 1.3 mmol) in dry CC14 (200 mL) was heated to 100 C under nitrogen atmosphere for 3 h. After TLC showed the starting material was completely consumed, the reaction mixture was cooled to RT and filtered through a pad of celite. The filtrate was dried over Na2S04 and concentrated to give a residue which was purified by flash chromatography on silica gel (eluting with petroleum ether/EtOAc 100/0 gradually increasing to 80/20) to give Scheme 48 compound 2 (20 g, 66%) as a brown liquid. MS [ESI, MH+] = 234.94.

The synthetic route of 3260-88-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 36556-42-0, name is 1-Chloro-2,3,4-trifluorobenzene, 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 36556-42-0, Quality Control of 1-Chloro-2,3,4-trifluorobenzene

The amine mother liquor, together with the production residues from the initial batch, is made up with 299.7 g (1.8 mol) of 4-chloro-1,2,3-trifluorobenzene and 4.1 g of 5% Pd/C (50% water-moist) and, analogously to the initial batch, is reductively dechlorinated and worked up correspondingly. The production residues resulting from the fractionation (forerunnings, intermediate runnings and residues from distillation) are recycled without further pretreatment to the subsequent batch. Conversion: 98.1% (by GC) Yield: 231.0 g (1.75 mol) of 1,2,3-trifluorobenzene 97.2% based on the 4-chloro-1,2,3-trifluorobenzene employed. Purity: >99.9 (GC area-%) 1,2,3-trifluorobenzene

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-Chloro-2,3,4-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoechst Aktiengesellschaft; US5498807; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 924818-16-6 as follows. Quality Control of (5-Chloro-2,4-difluorophenyl)methanamine

10489] A 50-mE 1-neck round bottom flask was charged with reactant 15-A (0.015 g, 0.047 mmol, the synthesis of 15-A is described in example 41), (5-chioro-2,4-difluorophe- nyl)methanamine (0.009 g, 0.05 mmol), DIPEA (0.06 g, 0.47 mmol) and HATU (0.035 g, 0.09 mmol) in DCM (3 ml). The reaction mixture was stirred at room temperature for 1 hout The reaction mixture was concentrated down, re-dissolved in EtOAc (50 mE), washed with saturated NaHCO3 twice, washed with saturated NH4C1 and dried over Na2 SO4. After concentration, the crude was purified by column chromatography on silica gel with hexane-EtOAc to obtain 15-B. ECMS-ESI (mlz): [M+H]. found: 483.

According to the analysis of related databases, 924818-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; Bacon, Elizabeth M.; Cai, Zhenhong R.; Cottell, Jeromy J.; Ji, Mingzhe; Jin, Haolun; Lazerwith, Scott E.; Morganelli, Philip Anthony; Pyun, Hyung-jung; (101 pag.)US2016/176870; (2016); A1;,
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Chlorides – an overview | ScienceDirect Topics

Reference of 2770-01-6, These common heterocyclic compound, 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, 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 improve the selectivity for the ^-substitution by blocking the N7-position with sterically demanded groups, 6-chloro-3-deazapurine (7) was converted to N-protected 3- deazaadenine derivatives (21a-b) (Scheme 2). Our initial attempts to convert the 6-chloride to the N6-amino group by methanolic ammonia or hydrazine/Raney-nickel gave 3-deazaadenine (13) in poor yields. However, the reaction of 7 with NaN3 or LiN3 provided 3-deaza- tetrazolopurine (12)la in about 80% and 82% yields with about 20% of starting material (7), which could not be removed from 12 (Table 1), respectively. The same reaction for 3-deaza- tetrazolopurine (12) was investigated by addition of an ionic liquid (DMF- [emim]BF4).13 LiN3 (20% in water) and DMF-[emim]BF4 ionic liquid (10:1 v/v) at 80 0C for 6 h provided 3- deaza-tetrazolopurine (12) in quantitative yield without 7. The ionic liquid was readily recovered by simple filtration, and recycled.14

Statistics shows that 4-Chloro-1H-imidazo[4,5-c]pyridine is playing an increasingly important role. we look forward to future research findings about 2770-01-6.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
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. 155535-20-9, name is 2-Chloro-5,6,7,8-tetrahydroquinoxaline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Chloro-5,6,7,8-tetrahydroquinoxaline

b) A mixture of intermediate (3), 1-bromo-2,5-pyrolidinedione (0.116 mol) and dibenzoyl peroxide (1.3g) in tetrachloromethane (400ml) was stirred and refluxed for 35 minutes, brought to room temperature and then filtered. The reaction was carried out again using the same quantities. The residues were combined. The solvent was evaporated. The residue (60g) was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc 85/5; 15-35 mum). Two pure fractions were collected and their solvents were evaporated, yielding 25 g (43%) of (+/-)-5-bromo-2-chloro-5,6,7,8-tetrahydroquinoxaline (interm. 4) and 12 g (21 %) of (+/-)-8-bromo-2-chloro-5,6,7,8-tetrahydroquinoxaline.

According to the analysis of related databases, 155535-20-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; EP1196410; (2004); B1;,
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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. 29242-84-0, name is 2-Chloro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8ClNO

To 80 mmol of compound 12 we added in succession 40 mL of water and 20 mL of conc. HCl. The suspension that formed was cooled on an ice bath, after which a solution of 85 mmol of NaNO2 in 40 mL of water was added to it under stirring over the course of 1 h. The solution was stirred for 15 min, and urea was then added until nitrogen no longer evolved. The resulting diazonium salt solution was added in small portions to a stirred solution of 120 mmol of KI in 40 mL of water at 0-5.To bring the reaction to completion, the mixture was heated at 60 for 10 min, cooled, 20% NaOH was then added, and the product was extracted with dichloromethane (3×50 mL). The organic layer was successively washed with 5% NaHSO3 (50 mL) and water (50 mL), dried over MgSO4, and distilled in a vacuum. Yield 45%, mp 136-138 (20 mmHg). 1NMR spectrum, delta, ppm: 3.80 s (3H, OCH3), 6.59 d.d(1H, J = 8.8, 2.9 Hz), 7.04 d (1H, J = 2.9 Hz), 7.68 d(1H, J = 8.8 Hz).

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 29242-84-0.

Reference:
Article; Khaibulova, T. Sh.; Boyarskaya; Polukeev; Boyarskii; Russian Journal of General Chemistry; vol. 86; 10; (2016); p. 2318 – 2324; Zh. Obshch. Khim.; vol. 86; 10; (2016); p. 1670 – 1677,8;,
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