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. 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-N,N-dimethylethanamine hydrochloride

General procedure: Requisite alkylaminoethyl chloride hydrochloride, chlorobromopropane and cyclopentyl bromide (6.0mmol) were added to a stirred and refluxing slurry of 4-hydroxybenzaldehyde (1.0g, 8.19mmol) in ethyl methyl ketone (C4H8O) (40ml) in the presence of anhydrous potassium carbonate (2.0g, 14.47mmol). The reaction mixture was further refluxed for 6h with continuous stirring. The completion of the reaction was monitored by TLC. On completion, the reaction mixture was cooled, filtered and the solvent was removed under reduced pressure to obtain an oily residue of corresponding aldehyde 3-9, which was used as such for further reaction.

The synthetic route of 4584-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yadav, Rakesh; Bansal, Ranju; Kachler, Sonja; Klotz; European Journal of Medicinal Chemistry; vol. 75; (2014); p. 327 – 335;,
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Electric Literature of 363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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 39: 1 -( r2-(Butyloxy)phenvnmethyl)-Lambda/-(2-chloro-6-fluorophenyl)-1 H- pyrazole-3-carboxamide.; To 1-{[2-(butyloxy)phenyl]methyl}-1 H-pyrazole-3-carboxylic acid (0.558 g, 2.03 mmol) was added thionyl chloride (5 ml, 68.5 mmol) followed by Lambda/,Lambda/-dimethylformamide (0.01 ml, 0.129 mmol). The reaction was stirred at ambient temperature under nitrogen for 22 h. The reaction mixture was concentrated in vacuo, then redissolved in DCM and re-concentrated (x 2) to give 1-{[2-(butyloxy)phenyl]methyl}-1 H-pyrazole- 3-carbonyl chloride as a very pale orange gum which solidified on standing (61 1 mg). To a solution of 2-chloro-6-fluoroaniline (29.1 mg, 0.2 mmol, Avacardo research Chemicals) in chloroform (0.2 ml) was added Lambda/,Lambda/-diisopropylethylamine (0.034 ml, 0.2 mmol) and dimethylaminopyridine (2 mg, 0.016 mmol). 1-{[2- (butyloxy)phenyl]methyl}-1 H-pyrazole-3-carbonyl chloride (29.2 mg, 0.1 mmol) in chloroform (0.2 ml) was then added and the resulting solution stirred and heated at 70 0C under reflux for 2 h. The solvent was removed under a stream of nitrogen and then dimethylsulphoxide (0.6 ml) added. The reaction mixture was purified by MDAP on SUNFIRE C18 column (Method D). The appropriate fraction was concentrated in vacuo then under nitrogen flow to give the title compound (9.8mg); LCMS: (System3) MH+= 402, tRET = 1.33 min.

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-6-fluoroaniline, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; VILE, Sadie; WO2010/122088; (2010); A1;,
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Electric Literature of 2687-12-9, 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. 2687-12-9, name is Cinnamyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

Representative experimental procedure for carboxylative coupling reaction Taking the carboxylative coupling of 4-methylphenylacetylene, cinnamyl chloride (2a), and CO2 as example: A 70 mL oven dried autoclave containing a stir bar was charged with AgI (0.5 mg, 0.002 mmol) and Cs2CO3 (978 mg, 3.0 mmol). 4-Methylphenylacetylene (232 mg, 2.0 mmol), cinnamyl chloride (458 mg, 3.0 mmol), and 20 mL dry DMF were added with syringe, respectively, after purging the autoclave with CO2 three times. The sealed autoclave was pressurized to appropriate pressure with CO2. The reaction mixture was stirred at 60 C for 24 h, then the autoclave was cooled to room temperature and the remaining CO2 was vented slowly. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, and filtered. The solvent was removed under vacuum. The product (E)-cinnamyl 4-methylphenylpropiolate (3b) (502 mg, 1.82 mmol, 91% yield) was isolated by column chromatography on silica gel (ethyl acetate/petroleum ether: 1:25).

The chemical industry reduces the impact on the environment during synthesis Cinnamyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Zhu, Chuang; Jiang, Jiao-Lai; Lu, Xiao-Bing; Tetrahedron; vol. 68; 44; (2012); p. 9085 – 9089;,
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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. 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H6ClN3O

Synthesis of 8-benzyl-2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0420] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine 1 (50 mg, 0.29 mmol) in DMF (0.25 mL) under argon atmosphere was added sodium hydride (35 mg, 0.87 mmol) at 0 C. After stirring for 5 mins, benzyl bromide (0.035 mL, 0.29 mmol) was added to the reaction mixture at RT and stirred for 2 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (10 mL) and extracted with 5% MeOH/ CH2CI2 (2 x 5 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 2% MeOH: CH2CI2 to afford 8-benzyl-2-chloro-7, 8-dihydro- 6H-pyrimido [5, 4-b] [1, 4] oxazine (75 mg, 98%) as an off-white solid. 1H-NMR (DMSO-<, 400 MHz): delta 7.70 (s, 1H), 7.33-7.21 (m, 5H), 4.78 (s, 2H), 4.20-4.17 (m, 2H), 3.50-3.48 (m, 2H); LCMS: 262.3 (M+l); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 4.10 min. 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/ CH2C12 (R 0.7). According to the analysis of related databases, 1303587-99-6, the application of this compound in the production field has become more and more popular. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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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. 622-86-6, name is (2-Chloroethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H9ClO

3- Bromophenylacetic acid (4.0 g, 18.6 mmol) was dissolved in trifluoroacetic anhydride (3.6 mL, 25.9 mmol), then (2-chloroethoxy)benzene (2.56 mL, 18.6 mmol) was added dropwise. The resulting mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution and then extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate and then concentrated on a rotary evaporator. The resulting residue was purified by chromatography on silica gel to afford the desired product (5.46 g, 83% yield) as a yellow solid. NMR (400 MHz, MeOD) delta 8.07 (d, J =8.9 Hz, 2H), 7.47-7.40 (m, 2H), 7.25-7.24 (m, 2H), 7.07(d, J = 8.9 Hz, 2H), 4.37-4.33 (m, 4H), 3.92-3.89 (m, 2H); MS (ESI) (m/z) 355 (M+H)+. (0862)

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 622-86-6.

Reference:
Patent; TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; CHILDERS, Wayne, E.; ABOU-GHARBIA, Magid; JACOBSON, Marlene, A.; FAN, Rong; MARTINEZ, Rogelio, L.; MELENSKI, Edward, George; (126 pag.)WO2017/205451; (2017); A1;,
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29027-20-1, name is 3-Chloro-5-methylaniline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 29027-20-1

Example XVII; S-chloro-delta-methyl-phenylsulphonyl chloride; A solution of 400 mg of sodium nitrite in 0.6 ml of water is added dropwise to 708 mg 3-chloro-5-methyl-aniline in 2 ml concentrated hydrochloric acid while being cooled in a bath of ice and common salt. The reaction mixture is stirred for 15 minutes at 00C and then added to a mixture of 4 ml of a saturated solution of sulphur dioxide in glacial acetic acid (approx. 30 %) and 200 mg copper(ll)chloride-dihydrate in 0.4 ml of water while being cooled. The cooling bath is removed and the reaction mixture is stirred for 15 minutes at ambient temperature, then at 400C, until no further development of gas can be detected. Then some ice water is added while cooling with an ice bath. After 5 minutes the precipitate formed is suction filtered, washed with some ice water and dried in the desiccator. The sulphonyl chloride obtained is reacted further without any further purification. Yield: 760 mg (68 % of theory)

The synthetic route of 29027-20-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/30715; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2687-12-9, name is Cinnamyl 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 2687-12-9, Quality Control of Cinnamyl chloride

To a suspension of Part A compound (1.00 g, 4.21 mmol) in THF (25 mL) at 0C was added n-butyllithium in hexanes (3.53 mL, 8.84 mmol) dropwise at such at rate to maintain the internal temperature near 0C. The resulting bright yellow solution was stirred at 0C for 0.5 h and treated with cinnamyl chloride (0.79 g, 4.63 mmol). The mixture was slowly warmed to room temperature and stirred for 2 h when it was diluted with water (40 mL) and ethyl acetate (40 mL). The layers were separated, the organic fraction dried (Na2SO4) and concentrated. The remainder was triturated with hexanes and the resulting solid recrystalized from hot methanol to give 1.20 g (79%) of title compound as white needles. mp 144C. TLC Silica gel (3:7 ethyl acetate/hexane) Rf=0.6.

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; BRISTOL-MYERS SQUIBB COMPANY; EP904262; (2004); B1;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, 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 13078-79-0, Recommanded Product: 13078-79-0

Step v) 3-(3-ChlorophenethyIamino)-N-cycIoheptyl-N-(2-(2-(8-hydroxy-2-oxo-l,2- dihydroquinolin-5-yl)ethylamino)ethyl)propanamide bis(trifluoroacetate)Benzyl 2-(N-cycloheptylacrylamido)ethyl(2-(8-hydroxy-2-oxo- 1 ,2-dihydroquinolin-5- yl)ethyl)carbamate (100 mg) [Step iv] and 2-(3-chlorophenyl)ethylamine (88 mg) were combined in ethanol (1.1 mL) and and heated within a CEM Discover microwave at 100 0C until the reaction was completed, as judged by LCMS (30 minutes). The mixture was then concentrated in vacuo prior to addition of acetic acid (3 mL) followed by 33% HBr in acetic acid (2 mL). The resulting solution was stirred for 2 h then concentrated in vacuo and the residue purified by reverse phase preparative HPLC (eluting with acetonitrile 0.1%5 aqueous trifluoroacetic acid). Product containing fractions were combined and concentrated in vacuo to afford the title compound as a solid (50 mg). MS (APCI+) 553 [M+H]+ 1H NMR (399.826 MHz, DMSO) delta 10.47 (s, IH), 10.34 (s, IH), 8.62 – 8.46 (m, 4H), 8.08 – 8.01 (m, IH), 7.41 – 7.31 (m, 3H), 7.27 – 7.22 (m, IH), 6.94 – 6.87 (m, 2H), 6.58 io (d, J = 10.0 Hz, IH), 3.72 – 3.63 (m, IH), 3.49 – 3.43 (m, 2H), 3.30 – 3.01 (m, 10H), 2.99 – 2.92 (m, 2H), 2.85 – 2.79 (m, 2H), 1.80 – 1.37 (m, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Chlorophenyl)ethanamine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/75025; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2845-89-8, A common heterocyclic compound, 2845-89-8, name is 1-Chloro-3-methoxybenzene, molecular formula is C7H7ClO, 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: Under N2 atmosphere, NHC-Pd(II)-Im complex 1 (6.5 mg,1.0 mol%), KOtBu (224.4 mg, 2.0 mmol), toluene (1.0 mL), ketones 3 (2.0 mmol or 0.7 mmol), and aryl chlorides 2 (1.0 mmol) were successively added into a Schlenk reaction tube. The mixture was stirred at the specified temperature for the listed time shown inTables 1-3. The reaction mixture was cooled to room temperature,then the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography to give the pure products.

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:
Article; Xiao, Zheng-Kang; Yin, Hui-Ying; Lu, Jian-Mei; Inorganica Chimica Acta; PA; (2014); p. 106 – 108;,
Chloride – Wikipedia,
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Related Products of 6276-54-6,Some common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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 sulfuryl chloride (5 g, 30.05 mmol) in acetonitrile (30 mE), was added 3-chloropropyl amine hydrochloride (486 mg, 5.00 mmol). The reaction mixture was allowed to react over 18 hr at 75-80 C. After the completion of the reaction, the resultant was concentrated under reduced pressure, extracted with ether and then kept under vacuum for a long time to remove remained sulfuryl chloride, giving 3-chloropropylsulfamoyl chloride that was used without thrther purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloropropan-1-amine hydrochloride, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Kim, Ki Young; Ahn, Jin Hee; Kang, Seung Kyu; Rhee, Sang Dal; Bae, Myung Ae; Ahn, Sung Hoon; Kim, Hee Youn; Jung, Won Hoon; Kang, Nam Sook; US2014/24636; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics