Tag: M.W=100-200

The chemical industry reduces the impact on the environment during synthesis 821-99-8, name is 1,9-Dichlorononane, I believe this compound will play a more active role in future production and life. 821-99-8

General procedure: To a DMF solution (63 mL) of 3b (1.06 g, 6.31 mmol) was added sodium hydride (55% oil dispersion, 340 mg, 7.8 mmol) at rt. After being stirred for 2 h at rt, the suspension was cooled to 0 C, and 1,8-dichlorooctane (3.40 mL, 3.47 g, 18.9 mmol) was added to the suspension. The mixture was allowed to warm to rt and stirred at rt for 2 h and then at 55 C for 10 h. After adding aqueous HCl solution (35%, 0.7 mL) at rt, the mixture was concentrated under reduced pressure and diluted with water (30 mL). The aqueous solution was washed with hexane (320 mL), treated with NaHCO3 until the pH reached to 9, and extracted with AcOEt (3*150 mL). The organic layers combined were washed with water (3500 mL), dried over anhydrous Na2SO4, concentrated under reduced pressure, and subjected to silica gel column chromatography (CHCl3/MeOH 100:0 to 96:4, v/v) to afford 4b[11] as a colorless oil (1.25 g, 3.97 mmol, 63%). Because 4b[11] tends to undergo inter- and intramolecular quaternization during storage, the obtained material was characterized only by 1H NMR and used for the next reaction immediately after the purification. 1H NMR (300 MHz, CDCl3, 25 C, TMS): delta=0.73 (3H, d, 3JH-H=6.6 Hz), 1.05 (3H, d,3JH-H=6.9 Hz), 1.24-1.34 (5H, m), 1.36-1.44 (2H, m), 1.47-1.51 (2H, m), 1.67-1.81 (3H, m), 2.08-2.19 (1H, m), 2.37 (3H, s), 3.24-3.39 (2H, m), 3.53 (2H, t, 3JH-H=6.9 Hz), 3.63-3.75 (3H, m), 6.92-6.93 ppm (2H, m).

The chemical industry reduces the impact on the environment during synthesis 821-99-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Noguchi, Tomohisa; Li, Chunji; Sasaki, Daisuke; Yamada, Kuniyo; Saigo, Kazuhiko; Ishida, Yasuhiro; Tetrahedron; vol. 72; 11; (2016); p. 1493 – 1504;,
Chloride – Wikipedia,
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A common compound: 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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. 13726-14-2

Step 1 : 4-choro-3-methoxy aniline (2.0 g, 12.6 mmol), 1-chloro-4-iodobenzene (3.33 g, 13.9 mmol, and sodium-tert-butoxide (6.04 g, 63 mmol) were taken in toluene (15 mL). The resulting mixture was purged with nitrogen, added Pd(OAc)2 (0.141 g, 0.63 mmol), [HPtBu3][BF4] ( 0.255 g, 0.88 mmol) and heated at 110 C for 12 h. After completion of the reaction, the reaction mixture was filtered through celite bed and concentrated under vacuum. The residue obtained was diluted with ethyl acetate (200 mL) washed with water, brine solution and dried over anhydrous Na2S04. The organic phase was concentrated and purified by the column chromatography (230-400 size mesh) to get the white solid 4-chloro-N-(4_chlorophenyl)-3- methoxy aniline (1.2 g, 35.2%). 1H NMR (400 MHz, DMSO-d6): delta 8.46 (s, 1H), 7.22-7.28 (m, 3H), 7.08-7.10 (m, 2H), 6.75 (s, 1H), 6.64 (d, J = 8.68 Hz, 1H), 3.80 (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, 13726-14-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; SPANGENBERG, Thomas; (129 pag.)WO2016/827; (2016); A1;,
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Chlorides – an overview | ScienceDirect Topics

13726-14-2, These common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-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.

A solution of 4-chloro-3-methoxyaniline (1.0 equivalent) dissolved in CH2CI2 (15 volumes) at 5 C was treated portion wise with N-bromosuccinimide (1.03 equivalents), warmed to 20 C and mixed for 5 minutes. A 5% aqueous Na2S03 solution (10 volumes) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried (Na2S04), filtered and concentrated. The resulting solid was triturated with a minimal volume of heptane and the solid was collected by filtration and dried to constant mass (80 % yield).

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 13726-14-2.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT GMBH & CO.KG; MARING, Clarence J.; PRATT, John K.; CARROLL, William A.; LIU, Dachun; BETEBENNER, David A.; HUTCHINSON, Douglas K.; TUFANO, Michael D.; ROCKWAY, Todd W.; SCHOEN, Uwe; PAHL, Axel; WITTE, Adreas; WO2012/87833; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4535-90-4, Adding some certain compound to certain chemical reactions, such as: 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, 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 4535-90-4.

Example 23trans-{2-[1-(4-Benzo[d]isothiazol-3-yl-cyclohexyl)-8-chloro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl]-ethyl}-methyl-amineA mixture of trans-1-(4-benzo[d]isothiazol-3-yl-cyclohexyl)-8-chloro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (35.0 mg, 0.0803 mmol), cesium carbonate (105 mg, 0.321 mmol) and 2-methylaminoethyl chloride hydrochloride (41.8 mg, 0.321 mmol) in acetonitrile (0.8 ml) was heated at 70 C. for 20 h. After cooling to room temperature the reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with three 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave title compound (19 mg, 48%) as off-white solid. MS m/e: 493 ([M+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 4535-90-4.

Reference:
Patent; Dolente, Cosimo; Schnider, Patrick; US2011/263573; (2011); A1;,
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 2729-34-2 as follows. 2729-34-2

General procedure: To a mixture of compound 19 (211 mg, 1.3 mmol, 1.0equiv) inethanol (10 mL) at 60 C, 18a (351 mg, 1.3 mmol, 1.0 equiv) wasadded. The reaction was stirred for 10 min, and then a warm sodiumbicarbonate solution (328 mg in 5mL water) was added over15 min. The reaction was stirred at 60 C for 1 h and then cooled toroom temperature. After extraction with ethyl acetate, the combinedorganic phase was dried over sodium sulfate and concentratedto give 20a as a crude brown solid (515 mg, 80%).

According to the analysis of related databases, 2729-34-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Shulun; Guo, Wei; Liu, Xiaohua; Sun, Pu; Wang, Yi; Ding, Chunyong; Meng, Linghua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 38 – 55;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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. 6940-78-9

A solution of 1-bromo-4-chlorobutane (22.25 ml, 0.19 mol) in diethyl ether (100 ml) was added dropwise (under N2 atmosphere) to a suspension of activated Mg turnings (4.67 g, 0.19 mol) in diethyl ether (100 ml). Some crystals of iodine were also added. The temperature in the flask increased, and the orange colour turned to white. Once the addition of 1-bromo-4-chlorobutane was completed, the reaction was cooled in an ice-bath and 2-naphthalenecarboxaldehyde (20.00 g, 0.13 mol) was added dropwise as a solution in THF (200 ml, dry). The reaction mixture was stirred in the ice-bath for 4 hours. Then the mixture was quenched with NH4Cl 1 N. Both phases were separated. The organic layer was washed with brine, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by flash chromatography (eluent: n-hexane/EtOAc 20:1). The desired fractions were collected and the solvent was evaporated, yielding intermediate 19.

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, 6940-78-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guillemont, Jerome Emile Georges; Dorange, Ismet; Lancois, David Francis Alain; Villalgordo-Soto, Jose Manuel; Ferdinand, Yvan Rene; Motte, Magali Madeleine Simone; Andries, Koenraad Jozef Lodewijk Marcel; Koul, Anil; US2010/63026; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4090-55-5, The chemical industry reduces the impact on the environment during synthesis 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, I believe this compound will play a more active role in future production and life.

To a stirred solution of S2 (0.84 g, 1.50 mmol) in THF (5 mL) at rt, 60%NaH (0.24 g, 6.0 mmol) was added and stirred for 30 min. Then 2,2-dimethyltrimethylene phosphorochloridate (0.39 g, 2.2 mmol) was added in one portion. After stirring for 9 hours at rt, the reaction was quenched by saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with water and brine and dried over MgSO4. After filtration, the reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography to give 1c as colorless foam in 85% yield (0.90 g, 1.3 mmol). 4-Fluorophenyl 3,4,6-tri-O-benzyl-2-O-(2,2-dimethyltrimethylenephosphornoyl)-1-thio-alpha-D-mannopyranoside (1c). TLC (hexane/EtOAc 5:3):Rf 0.50. [alpha]D = +76.8 (c = 1.1, CHCl3). 1H NMR (CDCl3, 600 MHz) 7.45 (dd, J= 9.0, 5.4 Hz, 2 H), 7.41 – 7.40 (m, 2 H), 7.35 – 7.27 (m, 11 H), 7.25 – 7.23 (m, 2H), 6.94 (pseudo-t, J = 9.0 Hz, 2 H), 5.59 (d, J = 1.8 Hz, 1 H), 5.11 (dt, J = 7.8,2.4 Hz), 4.91 (d, J = 10.8 Hz, 1 H), 4.82 (d, J = 11.4 Hz, 1 H), 4.63 (d, J = 11.4Hz, 1 H), 4.62 (d, J = 11.4 Hz, 1 H), 4.59 (d, J = 10.8 Hz, 1 H), 4.48 (d, J = 12.0Hz, 1 H), 4.33 (ddd, J = 5.4, 4.2, 3.0 Hz, 1 H), 4.14 (d, J = 10.8 Hz, 1 H), 4.09 (d,J = 10.8 Hz, 1 H), 3.96 (pseudo-t, J = 9.6 Hz, 1 H), 3.91 – 3.85 (m, 2 H), 3.76(ddd, J = 21.6, 10.8, 3.0 Hz, 1 H) 3.75 (dd, J = 10.8, 3.0 Hz, 1 H) 3.67 (ddd, J =22.2, 11.4, 3.0 Hz, 1 H), 1.22 (s, 3 H), 0.63 (s, 3 H). 13C NMR (CDCl3, 150 MHz) 162.8 (d, J = 246.9 Hz), 138.2, 138.0, 137.4, 134.9 (d, J = 8.1 Hz), 128.5,128.4, 128.36, 128.34, 128.2 (d, J = 3.3 Hz), 128.1, 128.0, 127.9, 127.6, 116.2 (d,J = 21.9 Hz), 87.4, 79.1, 78.39, 78.35, 78.30, 78.25, 78.1, 75.2, 74.4, 74.3, 74.1,73.4, 72.6, 71.9, 69.0, 32.0, 21.8, 20.1. HRMS (ESI) m/z calcd for C38H42FNNaO8PS [M+Na]+, 731.2214; found, 731.2223.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Manmode, Sujit; Sato, Takumi; Sasaki, Norihiko; Notsu, Ikumi; Hayase, Shuichi; Nokami, Toshiki; Itoh, Toshiyuki; Carbohydrate Research; vol. 450; (2017); p. 44 – 48;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

348-59-4, These common heterocyclic compound, 348-59-4, name is 2,5-Dichlorofluorobenzene, 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.

b [3-Cyclopropyl-3-(2.5-dichlorophenoxy)propyl]methylcarbamic Acid, 1,1-dimethylethyl Ester 1,4-Dichloro-2-fluorobenzene (165 mg, 1.00 mmol) and (3-cyclopropyl-3-hydroxypropyl)methylcarbamic acid, 1,1-dimethylethyl ester (230 mg, 1.00 mmol) were dissolved in dimethylsulfoxide (10 ml) under nitrogen at room temperature. To the resulting solution was added sodium hydride (60% in oil) (80 mg, 2.00 mmol). The solution was then allowed to stir at room temperature under nitrogen for 24 h. The mixture was then poured into water and extracted with diethyl ether three times. The combined organic fractions were washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue eluted down a flash chromatography column using 10% ethyl acetate/isohexane as eluent to give 175 mg (47%) of the title compound as an oil. 1H NMR 300 MHz (CDCl3) 7.26 (1H, m), 6.96 (1H, s), 6.87 (1H, m), 3.80 (1H, q), 3.42 (2H, m), 2.84 (3H, s), 2.01 (2H, m), 1.43 (9H, s), 1.10 (1H, m), 0.54 (2H, d), 0.30 (2H, bm).

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 348-59-4.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; US2003/65174; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, 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. 6940-78-9 name is 1-Bromo-4-chlorobutane, 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.

1-bromo-4-chlorobutane (3.4 g, 20 mmol), anhydrous potassium carbonate powder (4.14 g, 30 mmol) and 7-hydroxy-3,4-dihydro-2(1H)quinolinone 10 mmol)Was added to 10 ml of acetone, refluxed for 24 hours,, the reaction solution was evaporated to dryness, and the mixture was partitioned with 20 ml portions of dichloromethane and water. The organic layer was extracted with 20 ml of water * 2 and 20 ml of saturated brine successively, dried over anhydrous magnesium sulfate , Evaporate to dryness to give a pale yellow powder. The obtained powder is washed with slurry with 20 ml * 3 of n-hexane, filtered, and dried to obtain 1.98 g of 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)quinolinone. Yield is 78%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-chlorobutane, and friends who are interested can also refer to it.

Reference:
Patent; JIANGSU HENGYI PHARMACEUTICAL COMPANY LIMITED; SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY; Li, JIANQI; PENG, SHAOPING; CAI, WANGPING; GAO, KAI; (39 pag.)JP5714152; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, 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. 108-41-8.

General procedure: Under an N2 atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol %), dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol) were successively added into a Schlenk tube. The mixture was stirred vigorously at 90 C for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: PE/EA = 15:1) to give the pure products. The reported yields are the average of two runs.

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Saranya, Gandhi; Viswanathamurthi, Periasamy; Bertani, Roberta; Sgarbossa, Paolo; Malecki, Jan Grzegorz; Journal of Organometallic Chemistry; vol. 831; (2017); p. 1 – 10;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics