Tag: M.W=100-200

Synthetic Route of 13726-14-2, A common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); 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. 623-12-1, name is 1-Chloro-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7ClO

General procedure: A 25 mL synthesizer tube was taken with a mixture of aryl halide (0.5 mmol), aryl boronic acid (0.55 mmol),base (1.5 mmol), Pd-complex C1 (0.2 mol %) and the mixture was stirred in2 mL of water at 50C for the required time. After completion, the reaction mixture was extracted with ether (3 Chi 20 mL). The combined extract was washed with brine (2 Chi 20 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel,ethyl acetate-hexane: 1:9) to obtain the desired products. The products were confirmed by comparing the 1H and 13C NMR and mass spectral data with authentic samples.

According to the analysis of related databases, 623-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dewan, Anindita; Bora, Utpal; Borah, Geetika; Tetrahedron Letters; vol. 55; 10; (2014); p. 1689 – 1692;,
Chloride – Wikipedia,
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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;,
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Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Computed Properties of C7H7ClFN

A mixture of Example 235G (40.0 mg, 0.112 mmol), HATU (1- [bis(dimethylamino)methylene]-lH-l ,2,3-triazolo[4,5-]pyridinium 3-oxid (1666) hexafluorophosphate) (51.0 mg, 0.134 mmol), (4-chloro-3-fluorophenyl)methanamine (0.015 mL, 0.123 mmol), and triethylamine (0.031 mL, 0.224 mmol) in N,N-dimethylformamide (DMF) (1.5 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over MgSO/t, filtered, and concentrated. The residue was purified by HPLC performed on a Phenomenex Luna C18 column (250 x 30 mm, 10 mupiiota particle size) using a gradient of 20% to 100% acetonitrile:0.1 % aqueous trifluoroacetic acid over 26 minutes at a flow rate of 50 mL/minute to provide the title compound (49.6 mg, yield 89%). JH NMR (501 MHz, DMSO- ) delta ppm 8.29 (t, J = 6.3 Hz, 1H), 7.75 (s, 1H), 7.50 (dt, J = 15.1 , 8.5 Hz, 2H), 7.20 (dd, J = 10.4, 2.0 Hz, 1H), 7.11 – 6.99 (m, 2H), 6.82 (ddd, J = 9.0, 2.9, 1.1 Hz, 1H), 4.48 (s, 2H), 4.23 (d, J = 6.3 Hz, 2H), 4.03 (s, 2H), 2.13 – 1.95 (m, 4H), 1.95 – 1.77 (m, 4H); MS (ESI+) m/z 449.3 (M+H)+.

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-Chloro-3-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
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Related Products of 870-24-6, 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. 870-24-6, name is 2-Chloroethanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

13.5 g of 2-chloroethylamine hydrochloride was added to 8.7 g of mercaptoethanol solution under stirring, adjusted to pH=4.8, and reacted at 55 C. for 4 hours to produce 13.2 g.beta-2-aminoethylmercaptoethan-1-ol. Cooling to 0C,Slowly add 59g (40%) of tidal acetaminophenone chloride, adjust pH=3.8, control temperature at 0-2C for 4 hours, separate,Washing afforded 30.7 g of p-acetamidobenzenesulfonamide ethyl-2-hydroxyethyl sulfide

The chemical industry reduces the impact on the environment during synthesis 2-Chloroethanamine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Taixing Jinyun Dyeing Liao Co., Ltd.; Zhao Weiguo; Su Jinqi; Ju Suhua; Wang Guomin; Zhang Weiping; (27 pag.)CN104592786; (2017); B;,
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Application of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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: The syntheses of the ferrocenyl phenylguanidines were achieved in four steps (Scheme-1 suppl). In the first step; nitrophenylferrocene (a and b) were made by the coupling of ferrocene with diazonium salts of nitroaniline using phase transfer catalyst [20]. In the second step; these nitro phenyl ferrocene were reduced into ferrocenylaniline (c and d) using palladium on charcoal and hydrazine as reducing agent [21]. In the third step three different chloro-substituted thioureas (e) were synthesized by the coupling of substituted aniline with thiocynates in acetone [22]. In the fourth step; the benzoylphenylthiourea (e) were mixed with the ferrocenyl aniline (c and d) in dimethyl formamide (DMF) in equimolar ratio with two equivalents of triethylamine (Et3N). The temperature was maintained below 5C using an ice bath and one equivalent of mercuric chloride (HgCl2) was added to the reaction mixture with vigorous stirring. The ice bath was removed after 30min while the stirring continued overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) till the completion of reaction. Chloroform (CHCl3, 20ml) was added to the reaction mixture and the suspension was filtered through a sintered glass funnel to remove the mercuric sulfide (HgS) residue. The solvents from filtrate were evaporated under reduced pressure and residue was re-dissolved in dichloromethane (CH2Cl2, 20ml), washed with water (4×30ml) and dried the organic phase over anhydrous magnesium sulfate (MgSO4). The solvent was evaporated and residue was purified by column chromatography to afford ferrocenyl phenylguanidines (f and g) [23]. Solid and liquid state characterization data is given in Supplemental part

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloroaniline, its application will become more common.

Reference:
Article; Gul, Rukhsana; Badshah, Amin; Khan, Azim; Junaid, Asif; Rauf, Muhammad Khawar; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 264 – 269;,
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These common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, 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. Safety of 2,4-Dichloro-1-fluorobenzene

General procedure: As a typical experiment, the reaction of the 2-halopyridine (1 mmol), fluorobenzene derivative (2.5 mmol) and PivOK (0.154 g, 1.1 mmol) at 150 C during 16 h in DMA (3 mL) in the presence of PdCl(C3H5)(dppb) (12 mg, 0.02 mmol) (see tables or schemes) under argon affords the arylation product after evaporation of the solvent and filtration on silica gel

The synthetic route of 2,4-Dichloro-1-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boyaala, Rabab; Touzani, Rachid; Guerchais, Veronique; Soule, Jean-Francois; Doucet, Henri; Tetrahedron Letters; vol. 58; 33; (2017); p. 3205 – 3208;,
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Related Products of 72235-58-6,Some common heterocyclic compound, 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, molecular formula is C7H7ClFN, 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.

Step 3: Intermediate 201 OB (50 mg, 0.16 mmol) is dissolved in DMF (2.0 ml_), then diisopropylethylamine (1 10 muIota_, 0.63 mmol, 4.0 eq) and 4-chloro-3-fluorobenzylamine ( Oakwood) (30 mg, 0.19 mmol, 1 .2 eq) are added followed by HATU (78 mg, 0.21 mmol, 1 .2 eq) and the reaction mixture is stirred at RT. Following completion of the reaction, the solution is filtered and purified by preparative HPLC to provide compound 2010 (tR: 1 .71 , (M+H)+: 459.2/461 .2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Chloro-3-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
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Related Products of 2613-34-5, 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. 2613-34-5, name is 3-Chloro-2,4-difluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2- yl)sulfamoyl)-1H-pyrrole-2-carboxylic acid (450 mg, 1.43 mmol) and 3-chloro-4,5- difluoroaniline hydrochloride (0.57 g, 2.86 mmol) (synthesis described in synthesis for compound 57) and HATU (0.73 g, 1.91 mmol) were dissolved in DMF (2 mL) containingdiisopropylethylamine (0.82 mL, 4.77 mmol). The reaction mixture was stirred at 40C for 66 hours. The reaction mixture was directly loaded on column. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combined and evaporated to keep 50 mL of solvent. The precipitates were filtered and washed with petroleum ether and dried in vacuum oven at 50C overnight to affordcompound 137 (490 mg) as white powder.(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2-yl)sulfamoyl)- 1 H-pyrrole-2-carboxylic acid (168mg, 0.53 mmol) (synthesis described in synthesis for compound 137) 5-amino-2-fluorobenzonitrile (0.15 g, 1.07 mmol) and HATU (0.24 g, 0.64 mmol) were dissolved in DMF (1 mL) containing diisopropylethylamine (0.23 mL, 1.34 mmol). The reaction mixture was stirred at 50C for 1 hour. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combinedand evaporated to keep 50 mL of the solvent. The white solids were filtered and dried invacuum oven to afford compound 140 (180 mg) as white powder.Compound 143 (147 mg) as white powder was synthesized similarly as described for compound140 using 3-chloro-2,4-difluoroaniline (0.17 g, 1.07 mmol) instead of 5-amino-2-fluorobenzonitrile. The reaction mixture was stirred at 60C for 2 hours more. Method B; Rt:1.07 mi mlz: 458 (M-H) Exact mass: 459.04. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.09 (d,J7.0 Hz, 3 H), 2.44 (s, 3 H), 3.82 (s, 3 H), 3.76 – 3.91 (m, 1 H), 7.34 (td, J=9.0, 2.0 Hz, 1 H),7.35 (s, 1 H), 7.52 (td, J8.7, 5.8 Hz, 1 H), 8.20 (br. s., 1 H), 10.05 (s, 1 H).

The synthetic route of 3-Chloro-2,4-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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Related Products of 20850-43-5,Some common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, molecular formula is C8H7ClO2, 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 a slurry of magnesium turnings (1.09 g, 44.8 mmol) in 5 mL of THF was added iodine (0.0650 g, 0.256 mmol), followed by a solution of 5-(chloromethyl)benzo[d][l,3]dioxole (6.55 g, 38.4 mmol) in 30 mL of THF. After 1 minute, the exothermic reaction mixture was placed in an ice bath for 1 minute and then stirred at ambient temperature for 1 hour. TMEDA (7.68 ml, 51.2 mmol) was added to the reaction and the mixture was cooled to -78 0C for 5 minutes at which point a solution of (E)-N-((S)-2,3-bis(tert- butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (5400 mg, 12.8 mmol) in 25 mL THF was added via a syring pump over 15 minutes. The reaction was allowed to warm to RT over the course of 2 hours then stirerd at RT for an additional hour. The mixture was diluted with ethyl acetate (100 mL) and poured in saturated ammonium chloride (250 mL). The aqueous layer was extracted with ethyl acetate (2 x 250 mL) and the combined organic layers were washed with water and then brine and dried over Na2SO4. The organic colvents were filtered, concentrated under reduced pressure and the crude material was purified by silica gel to provide N-((2R,3S)-1- (benzo[d][l,3]dioxol-5-yl)-3,4-bis(tert-butyldimethylsilyloxy)butan-2-yl)-2- methylpropane-2-sulfinamide (4.51 g, 63.1% yield) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Chloromethyl)benzo[d][1,3]dioxole, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/64418; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics