Tag: M.W=100-200

402-46-0, A common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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: The synthesis route of compounds 1-24 followed the general pathway outlined in Scheme 1. The substituted nicotinic acid (1 mmol) mixed with benzenesulfonamide (1 mmol) through by using 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC¡¤HCl) (1.2 mmol) and 4-dimethylaminopyridine (DMAP) (1.2 mmol) in anhydrous CH2Cl2 for 6-8 h at 70-80 C. The reaction was monitored by TLC. The products are extracted with ethyl acetate. The extract is washed successively with 1 N HCl, water, 1 M NaHCO3, and water, dried over MgSO4, filtered and evaporated. The residue is purified by column chromatography using petroleum ether and ethyl acetate (1:1).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Hui; Lu, Xiang; Zhang, Li-Rong; Liu, Jia-Jia; Yang, Xian-Hui; Wang, Xiao-Ming; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 4; (2012); p. 1411 – 1416;,
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Some common heterocyclic compound, 6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, molecular formula is C7H10N2O2S, 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. 6973-09-7

To a solution of Intermediate Example 4 (200 mg, 0.695 mmol) and 5-amino-2- methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of cone. HCI. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. The hydrochloride salt of 5-({4-[(2,3-dimethyl-2/-/-indazol-6- yl)(methyl)amino]-pyhmidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J = 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz, 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1 H), 6.86 (m, 1 H), 5.74 (d, J = 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

The chemical industry reduces the impact on the environment during synthesis 5-Amino-2-methylbenzenesulfonamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143483; (2007); A2;,
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A common compound: 627-12-3, name is Propyl carbamate, belongs to amides-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. 627-12-3

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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, 627-12-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
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34801-09-7, A common compound: 34801-09-7, name is N-(2-Aminophenyl)acetamide, belongs to amides-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.

General procedure: added 4-dimethylaminopyridine (DMAP) to compound 9 of anhydrous tetrahydrofuransolution, stirring at room temperature for 30 min. Then added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimidehydrochloride (EDCI?HCl) was to the reaction mixture and continued stirring 0.5-1h. Phenylenediamine derivatives were added to the reaction mixture, continued stirringat room temperature under nitrogen until the disappearance of the startingmaterial 9 (TLC monitoring). Afterevaporation of the solvent, residue was diluted in CH2Cl2and washed with saturated NaHCO3, water and saturated NaCl. Theorganic layer was dried over Na2SO4, filtrated, and evaporatedthe solvent in vacuo. The resulting residue was purified by silica gelchromatography to yield the corresponding product.

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, N-(2-Aminophenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Song, Jiao; Peng, Peng; Chang, Jun; Liu, Ming-Ming; Yu, Jian-Ming; Zhou, Lu; Sun, Xun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2174 – 2178;,
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3119-02-6, Adding some certain compound to certain chemical reactions, such as: 3119-02-6, name is 4-Cyanobenzenesulphonamide, 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 3119-02-6.

General procedure: To a stirred suspension of nitrile (30 mmol) and hydroxylaminehydrochloride (3.13 g, 45 mmol) in EtOH (50 mL) a NaHCO3 (3.78 g,45 mmol)was added. The reaction mixturewas stirred under refluxfor 6 h. After the reaction had completed, the reaction mixture wasconcentrated under reduced pressure, and the residue was dilutedwith cold water (80 mL). The resulting precipitate was filtered off,washed with cold water (20 mL) and dried in air at roomtemperature.4.2.3. N’-Hydroxypicolinimidamide (10a) [35]Yield 3.54 g (86%); White solid; m.p. 117-118 C. 1H NMR(400 MHz, DMSO) delta ppm 9.90 (s, 1H), 8.57 (d, J 4.8 Hz, 1H), 7.86 (d,J 7.9 Hz, 1H), 7.82 (t, J 8.1 Hz, 1H), 7.40 (t, J 6.6 Hz, 1H), 5.80(br.s, 2H).

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 3119-02-6.

Reference:
Article; Krasavin, Mikhail; Shetnev, Anton; Sharonova, Tatyana; Baykov, Sergey; Kalinin, Stanislav; Nocentini, Alessio; Sharoyko, Vladimir; Poli, Giulio; Tuccinardi, Tiziano; Presnukhina, Sofia; Tennikova, Tatiana B.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 92 – 105;,
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90-16-4, 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 90-16-4 as follows.

A solution of the alcohol from step 7 (0.050 g, 0.109 mmol), triphenylphosphine (0.057 g, 0.217 mmol) and benzo-1,2,3-triazin-4(3H)-one (0.034 g, 0.231 mmol) in THF (2.5 mL) was treated with diethyl azodicarboxylate (0.035mL, 0.222 mmol). The mixture was stirred at room temperature for 16 hrs., concentrated under reduced pressure and purified by MPLC (0-20% EtOAc-hexanes) to give the target compound (0.034g, 53%). TLC: Rf 0.16 (silica, 20% EtOAc-hexanes).

According to the analysis of related databases, 90-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Corporation; EP923530; (2004); B1;,
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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. 630-22-8 name is 2,2-Dimethylpropanethioamide, 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. 630-22-8

General procedure: To a suspension of different thioamides 1b, 2b, 3b (7.28 mmol)in ethyl alcohol (15 mL) was added at room temperature ethyl 2-chloroacetoacetate (1 equiv.). The solution was refluxed for 24 h,and then the solvent was removed under reduced pressure. Thesolid material was washed with cooled hexane (2 10 mL) to givethe corresponding pure ethyl carboxylate derivatives 1c, 2c, 3c indifferent yields. Ethyl 2-(tert-butyl)-4-methylthiazole-5-carboxylate (1c).Prepared from 2,2-dimethyl propanthioamide (1b). Yellow solid75.3%; mp: 43e47 C [40].

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

Reference:
Article; Ghonim, Aya E.; Ligresti, Alessia; Rabbito, Alessandro; Mahmoud, Ali Mokhtar; Di Marzo, Vincenzo; Osman, Noha A.; Abadi, Ashraf H.; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 154 – 170;,
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121492-06-6, The chemical industry reduces the impact on the environment during synthesis 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, I believe this compound will play a more active role in future production and life.

A solution of [6-chloro-3-(1’H,3H-spiro[2-benzofuran-1,4′-piperidin]-1′-ylcarbonyl) -1H-indol-1-yl]acetic acid (prepared by treatment of the sodium salt of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidine] with bromoacetic acid at room temperature in DMF), 0-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (1.05 eq) and Et3N (1.05 eq) were stirred together at room temperature in dry DMF for 15 min. Commercially available N-(2-aminoethyl)-N-methylcarbamic acid tert-butyl ester (1.5 eq) was added and the solution stirred at room temperature for 2 h, then a solution of HCl (15 eq) in dioxane was added and the solution stirred for 2 h. Evaporation and purification by prep. HPLC gave 37% of product. ES-MS m/e (%): 481.3(M+H+).

The chemical industry reduces the impact on the environment during synthesis N-Boc-(2-Aminoethyl)-N-methylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bissantz, Caterina; Grundschober, Christophe; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2007/27173; (2007); A1;,
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A common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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. 16066-84-5.

To a suspension of sodium hydride (0.056g, 1.41 mmol) in DMF (3 mL) was added a solution of methylcarbamic acid t-butyl ester (0.184 g, 1.41 mmol) in DMF (2 mL). After stirring 1 hr, a solution of 3-(3-chloropropyl)-7-fluoro-1 -phenyl-1 H-4,2,1 – benzoxathiazine 2,2-dioxide (0.25 g, 0.72 mmol) in DMF (4 mL) was added. The mixture was stirred for 2 hr then poured into 2N HCI and extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate then concentrated and the residue purified by Sitheta2 column chromatography (10-35% gradient ethyl acetate/hexane). The purified residue was then dissolved in 5 mL of 2N HCI in ether and 0.1 mL of MeOH and the solution allowed to stand 18 hr whereupon crystals formed. The crystals were collected by filtration to yield 3-(7-fluoro-2,2-dioxido-1 – phenyl-1 H-4,2,1-benzoxathiazin-3-yl)-N-methylpropan-1 -amine hydrochloride (0.159): MS (ES) m/z 350.9;HPLC purity 100.0% at 210-370 nm, 7.4 minutes; Xterra RP18, 3.5 mu, 15O x 4.6 mm column, 1.2 mL/minutes. 85/15-5/95 (ammonium formate buffer pH =3.5/ACN+MeOH) for 10 minutes, hold 4 minutes.HRMS: calculated for Ci7H19FN2O3S + H+, 351.11732; found (ESI, [M+H]+), 351.1161.

The synthetic route of tert-Butyl methylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2008/73956; (2008); A2;,
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Some common heterocyclic compound, 98-10-2, name is Benzenesulfonamide, molecular formula is C6H7NO2S, 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. 98-10-2

To a 500 ml flask was added 100 g of isopropanol,50g of benzene sulfonamide dissolved in the preparation of sodium hydroxide,Isopropanol-sodium alcohol solution (14g isopropyl alcohol dissolved in 26g isopropyl alcohol), water bath temperature, while opening the mechanical stirring,When the temperature to 50-55 C, the solid is completely dissolved, began dropping benzenesulfonyl chloride 62g, while dropping sodium hydroxide,Isopropanol-sodium alcohol solution (28g isopropyl alcohol sodium dissolved in 52g isopropyl alcohol), control system pH value of 8 to 10,Control the rate of dropping, dropping finished in 50-55 C for 2h, through the hydroxide anion exchange resin.The reaction solution was cooled to 10 C and centrifuged to obtain BBI sodium salt. The sodium salt is dissolved in hot water,Crystals were precipitated by lowering the temperature by SAPPS cation exchange resin, and the crystals were vacuum dried at 40-50 C,To obtain 84.7 g of solid bis-benzenesulfonimide. As shown in Fig. 7, the results of the HPLC detection showed: benzenesulfonamide: 0.02%;Benzenesulfonyl chloride: 0.02%; NaCl: 0.08%; BBI: 99.96%; Yield: 89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98-10-2, its application will become more common.

Reference:
Patent; Hubei Kyrgyzstan and Chang Chemical Technology Co., Ltd; Xiao, Zhongxin; Feng, Qingcheng; Yang, Wei; Zhou, Shijun; Ming, Ruitao; Guo, Xinyue; Hu, Zhe; Huang, Kaiwei; (8 pag.)CN106187831; (2016); A;,
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