Tag: M.W=100-200

A common compound: 452-83-5, name is 2-Chloro-5-fluoroaniline, 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. 452-83-5

To a mixture of (5.0 g) 2-chloro-5-fluoroaniline (commercially available, 6.0 g), glycerol (6.0 g) and m-nitrobenzene sulfonic acid sodium salt (11.0 g), was added 20 ml of 70% sulfuric acid dropwise. The reaction temperature was raised to 140 C. for 2 hr. The mixture was then cooled, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2 to give 3.7 g of the desired product of a yellow solid; MP=74-76 C.; MS (ES) m/z (relative intensity): 182 (M+H)+ (100).

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, 452-83-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2007/27160; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 13078-79-0

Step iii) 3-(3-Chlorophenethylamino)-N-cyclohexyl-N-(2-(2-(8-hydroxy-2-oxo-l ,2- dihydroqumolin-5-yl)etliylamino)ethyl)rhoropanamide bis(trifluoroacetate)Benzyl 2-(N-cyclohexylacrylamido)ethyl(2-(8-hydroxy-2-oxo- 1 ,2-dihydroquinolin-5- yl)ethyl)carbamate (70 mg) [Step ii] and 2-(3-chlorophenyl)ethylamine (63 mg) were combined in ethanol (5.8 niL) and the resulting solution stirred at 50 0C for 18 h. The mixture was then concentrated in vacuo prior to addition of acetic acid (2 mL) followed by 33% HBr in acetic acid (3 mL). The resulting solution was stirred for 3 h then concentrated in vacuo and the residue partially purified by flash chromatography on silica (eluting with 10% methanol in dichloromethane). Product containaing fractions were combined and concentrated in vacuo. The residue was further purified by reverse phase preparative HPLC (eluting with 5-40% acetonitrile in 0.1% aqueous trifluoroacetic acid). Product containing fractions were combined and concentrated in vacuo to afford the title compound as a solid (5 mg) MS (APCI+) 539 [M+H]+1H NMR (399.825 MHz, CD3OD) delta 8.16 (d, J = 9.7 Hz5 IH)5 7.41 – 7.35 (m, 2H), 7.30 – 7.22 (m, 2H), 6.98 (dd, J = 22.2, 8.1 Hz52H), 6.66 (d, J= 10.0 Hz5 IH), 3.65 – 3.57 (m, 3H)5 3.38 – 3.27 (m, 4H), 3.23 – 3.14 (m, 8H), 2.91 (t, J = 6.0 Hz, 2H), 1.88 – 1.82 (m, 2H), 1.79 – 1.74 (m, 2H), 1.70 – 1.63 (m, IH), 1.56 – 1.26 (m, 4H), 1.22 – 1.09 (m, IH).

The synthetic route of 13078-79-0 has been constantly updated, and we look forward to future research findings.

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

1871-57-4, Adding some certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1871-57-4.

Step 1: methyl 14-cyclohex^l-7-meiksiotalene-7.&-dihydro-6H-indolol.2-e]fl.5]benzoxazocine-ll- carboxylate; To a solution of methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-lH-indole-6-carboxylate (prepared as described in example 9, step 1) in dry DMF (0.06 M) was added NaH (2.5 eq., 60% suspension in mineral oil). After 30 min, 3-chloro-2-(chloromethyl)prop-l-ene (1.2 eq.) was added dropwise via syringe and EPO the solution stirred at RT for 60 min. The reaction mixture was diluted with EtOAc and washed with IN aqueous HCl and with brine, dried (Na2SO4) and evaporated. The crude residue was purified by flash chromatography (10:1 PE/EtOAc), affording the pure methyl 14-cyclohexyl-7-methylene-7,8-dihydro- 6H-indolo[l,2-e][l,5]benzoxazocine-l l-carboxylate (70%) as light yellow foam; MS (ES+) m/z 402 (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 1871-57-4.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

29671-92-9,Some common heterocyclic compound, 29671-92-9, name is Carbamimidic chloride hydrochloride, molecular formula is CH4Cl2N2, 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: A solution of 6-chloro-3-nitropicolinonitrile (25) (0.60 g, 2.7 mmol) and an appropriate aniline was heated at 130 C in isopropanol. After 3-16 h, the solution was concentrated under reduced pressure. The precipitate obtained was neutralized with solution of ammonia in methanol to afford 26-38 as a crude product. The next step was carried out without any purification. To a suspension of 26-38 in methanol (20 mL) and concentrated hydrochloric acid (36%, 2 – 4.0 mL) was added iron powder. The mixture was refluxed until all the starting material had reacted (monitored on TLC). The hot reaction mixture was poured into water (20 mL) and stirred for 5 min. The unreacted iron was removed using a stirring bar retriever, and the aqueous solution was neutralized with ammonium hydroxide to pH 4. The solution was then extracted with chloroform (3 ¡Á 20 mL), and the combined organic layer was washed with water (2 ¡Á 5.0 mL), sodium bicarbonate solution (5.0 mL), and brine (5.0 mL) and dried over anhydrous sodium sulfate. The product (39-52) was obtained as a gummy brown semi-solid. The next step was carried out without any purification and characterization. Mixture of 39-52, chloroformamidine hydrochloride (1 g), and dimethyl sulfone (4.0 g) was heated in an oil bath at 140 C under nitrogen for 15 min. The oil bath was removed, and water (10 mL) was added slowly to the hot reaction mixture. The aqueous solution was cooled to room temperature and extracted with chloroform (3 ¡Á 5 mL) to remove dimethyl sulfone. The aqueous phase was made basic to pH 10 with ammonium hydroxide, followed by removal of water under reduced pressure. The residue was dissolved in a mixture of 50:50 methanol-acetone (v/v), and silica gel was added (3.0 g). After the removal of solvent with a rotary evaporator, the silica gel plug was loaded onto a column and eluted with 1:5 MeOH-CHCl3 (v/v). The fractions containing the required compound were evaporated under reduced pressure to afford the targeted compounds.

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

Reference:
Article; Shah, Khushbu; Queener, Sherry; Cody, Vivian; Pace, Jim; Gangjee, Aleem; Bioorganic and Medicinal Chemistry Letters; vol. 29; 15; (2019); p. 1874 – 1880;,
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: The typical procedure is as follows. Oven dried Schlenk tube was equipped with stirrer bar, was charged with aryl halides (1 mmol), acrylates (1.2 mmol), K2CO3 (2 mmol) and catalyst2 (3 mol %) in DMF medium. The reaction mixture was stirred in an oil bath at 100C under argon atmosphere for an appropriate period of time. After completion of the reaction, the reaction mixture was then cooled to room temperature and diluted with Et2O/H2O(1:1, 20 mL). The organic layer was alienated and dried with anhydrous MgSO4. The product was filtered and dried under vacuum. The resulting crude compound was purified by column chromatography on silica gel to afford the corresponding products.

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

Reference:
Article; Nirmala, Muthukumaran; Arruri, Sathyanarayana; Vaddamanu, Moulali; Karupnaswamy, Ramesh; Mannarsamy, Maruthupandi; Adinarayana, Mannem; Ganesan, Prabusankar; Polyhedron; vol. 158; (2019); p. 125 – 134;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 10061-02-6, name is trans-1,3-Dichloropropene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 10061-02-6

A suspension of 6.66 g (0.06 mol) of (E)-1,3-dichloropropene (3), 13.82 g (0.1 mol) of potassium carbonate, and 2.53 g (0.031 mol) of ethylamine hydrochloride in 75 mL of anhydrous acetonitrile was slowly heated to the boiling point with stirring and was then refluxed until complete conversion of 3 (12-14 h, GLC monitoring). The mixture was cooled and filtered, the precipitate was washed with ethyl acetate, the organic fractions were combined and concentrated, and the product was isolated by vacuum distillation. Yield 4.24 g (73%), bp 89 C (4-5 mm). IR spectrum, nu, cm-1: 2971, 2935,2811, 1635, 1456, 1360, 1285, 1132, 934, 801. 1H NMR spectrum, delta, ppm: 1.03 t (3H, CH3, J =7.2 Hz), 2.50 q (2H, CH3CH2N, J = 7.2 Hz), 3.09 d (4H, CH2CH=, J = 6.8 Hz), 5.93 d.t (2H, CH2CH=, Jtrans = 13.2, 6.8 Hz), 6.12 d (2H, ClCH=, Jtrans = 13.2 Hz). 13C NMR spectrum, deltaC, ppm: 11.94 (CH3), 46.80 (CH3CH2N), 52.74 (2C, CH2CH=), 119.99 (2C, ClCH=), 130.41 (2C, CH2CH=). Mass spectrum, m/z (Irel, %): 193 (5) [M]+, 180 (20), 178 (32), 132 (17), 77 (33), 75 (100), 68 (49), 56 (10), 49 (9), 42 (13), 39 (29).

The synthetic route of 10061-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shakhmaev; Sunagatullina, A. Sh.; Zorin; Russian Journal of Organic Chemistry; vol. 53; 6; (2017); p. 832 – 835; Zh. Org. Khim.; vol. 53; 6; (2017); p. 818 – 820,3;,
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 344-19-4 as follows. 344-19-4

Method 2: Example 27: [2-(2,6-Dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)amine Step 1 : l-(4-Azidopyridin-3-yl)meth-(E)-ylidene]-(2,6-dichloro-4-fluorophenyl)amine Titanium tetrachloride (1M, 4.0 mL, 4.15 mmol) was added to a cooled (0 C) mixture of 4-azidopyridine-3- carbaldehyde (1.0 g, 6.75 mmol), 2,6-dichloro-4-fluorophenylamine (1.22 g, 6.75 mmol) and triethylamine (2.8 mL, 20.3 mmol) in DCM (24 mL), under nitrogen. The reaction was stirred for 30 minutes at 0 C, warmed to room temperature, stirred for an additional 2 h, and concentrated under reduced pressure. The residue was dissolved in toluene and filtered though a pad of Celite. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (2.09 g, quant.). This crude material was employed in the next step without further purification or analysis.

According to the analysis of related databases, 344-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; GOODACRE, Simon; LAI, Yingjie; LIANG, Yun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/66061; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, These common heterocyclic compound, 2533-69-9, name is Methyl 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.

Methyl 2,2,2-trichloroacetimidate (408 ml, 3.30 mmol), diisopropylethylamine (473 ml, 2.72 mmol) and ammonium chloride (73 mg, 1.36 mmol) were added to a solution of compound 96 (943 mg, 3.00 mmol) in acetic acid (6.0 ml) under ice-cooling, and the mixture was stirred for 45 minutes at room temperature. After water (15 ml) was added to the reaction mixture, precipitated crystals were collected and dissolved in THF (27 ml). 5 N sodium hydroxide solution (3 ml) was added to the solution and the mixture was stirred for 1 .5 hours at room temperature. The reaction mixture was concentrated and acidified to pH 3 – 4 with 2 N hydrochloric acid. Precipitated crystals were collected and washed with water to give compound 99 (770 mg, 70 %) as reddish-brown crystals. NMR (CDCl3) ?: 4.28 (3H, s), 4.45 (2H; s), 7.06 (2H, m), 7:33-(1H; d; J=8.5Hz), 7.39 (2H, m), 7.80 (1H, d, J = 8.6 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 2533-69-9.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1375486; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9, These common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, 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.

Acetic anhydride (10 mL, 106 mmol) was added to a solution of 2-chloro-6-fluoroaniline (12.81 g, 88 mmol) in AcOH (44 mL) and the mixture was stirred at 90 C. for 2 hrs. After cooling to r.t., water was added and the solid precipitate was collected by filtration, washed with water, and air dried to afford N-(2-chloro-6-fluorophenyl)acetamide (16.2 g, 98% yield) as a white solid. The crude product obtained was used directly in the next step without further purification. LCMS calculated for C8H8ClFNO (M+H)+: m/z=188.0; Found 188.0.

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 363-51-9.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Vechorkin, Oleg; Sokolsky, Alexander; Ye, Qinda; Liu, Kai; Yao, Wenqing; (60 pag.)US2020/48241; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, 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. 2613-34-5

3-CHLORO-2, 4-DIFLUOROANILINE (1.7 g, 10.1 mmol) and 5N hydrogen chloride in isopropanol (2 ml) were added to a suspension of tert-butyl 4- [ (4-CHLORO-7-METHOXYQUINAZOLIN-6- yl) oxy] PIPERIDINE-1-CARBOXYLATE (4 g, 10.1 mmol, PCT Int. Appl. W02003082831, AstraZeneca) in isopropanol (50 ml). The mixture was stirred at 80C for 3 hours. After evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 5-10% 7N methanolic ammonia in dichloromethane) to give 4- (3-CHLORO-2, 4-difluoroanilino) – 7-METHOXY-6-[(PIPERIDIN-4-YL) OXY] QUINAZOLINE (3.63 g, 85%) as a white solid. HNMR Spectrum: (CDC13 + CD3CO2D) : 2.15 (m, 2H), 2.30 (m, 2H), 3.34 (m, 2H), 3.47 (m, 2H), 4.01 (s, 3H), 4.91 (m, 1H), 7.03 (m, 1H), 7.58 (m, 2H), 7.90 (s, 1H), 8.55 (s, 1H) ; Mass spectrum: MH+ 421.

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 2613-34-5.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/28470; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics