Tag: M.W=100-200

Electric Literature of 78888-18-3, The chemical industry reduces the impact on the environment during synthesis 78888-18-3, name is tert-Butyl allylcarbamate, I believe this compound will play a more active role in future production and life.

(20 g, 127.39 mmoL)Soluble in N,N-dimethylformamide (100mL),Sodium hydride (7.6g, 60%, 191.08mmoL)After treatment with n-hexane,Add N,N-dimethylformamide (400 mL),Under the protection of nitrogen,Add dropwise to the reaction solution at 0 C, and stir at 0 C for 30 minutes.The reaction was continued for 20 minutes at room temperature.Bromopropyne (30.3g, 245.78mmoL) was added dropwise under ice bath.Stir at 0 C for 30 minutes. The reaction solution was slowly added to crushed ice to treat excess sodium hydride.Extracted with ethyl acetate (100 mL ¡Á 3),The organic phases were combined and washed with saturated brine (100 mL¡Á3).Dry over anhydrous sodium sulfate, filter,The filtrate was concentrated under reduced pressure.The residue was purified by silica gel column chromatography ( petroleum ether / ethyl acetate (v/v) = 100:1 – 50:1) to afford(21 g, yield 85%).

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, tert-Butyl allylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Feng Jianchuan; Peng Fei; Chen Qingping; (45 pag.)CN105085530; (2019); B;,
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Related Products of 1171331-39-7, A common heterocyclic compound, 1171331-39-7, name is 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride, molecular formula is C4H8ClF3N2O, 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.

To a stirred solution of (Z)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoic acid (200 mg, 0.41 mmol) in anhydrous THF (5.0 mL) was added DCI (82 mg, 0.51 mmol). The mixture was heated in a 50 C. oil bath for 1.5 h, treated with 2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride (109 mg, 0.057 mmol) and the resulting mixture heated to reflux for 8 h. After cooling to ambient temperature, the mixture was taken up in Et2O and washed twice with aq. 5% NaHSO4 (2¡Á) and once with sat. NaCl (1¡Á). After dying over MgSO4, concentration in vacuo and purification by medium pressure chromatography on silica with EtOAc/Hexanes as the eluents, the title compound was obtained as a white foam (160 mg, 41%) mp 48-61 C.: 1H NMR (400 MHz, CDCl3) delta 7.58 (d, J=7.9 Hz, 1H), 7.44-7.29 (m, 3H), 7.14 (dd, J=7.9, 1.6 Hz, 1H), 6.86 (d, J=11.4 Hz, 1H), 6.76 (t, J=5.9 Hz, 1H), 6.59 (br s, 1H), 6.21-6.04 (m, 1H), 4.23 (d, J=5.5 Hz, 1H), 3.98 (qd, J=9.0, 6.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -69.31, -72.3; EIMS m/z 626.9 ([M+1]+).

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:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171308; (2014); A1;,
Amide – Wikipedia,
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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. 4664-01-1, name is 3,4-Pyridinedicarboximide, A new synthetic method of this compound is introduced below., SDS of cas: 4664-01-1

Step 1 To 10% aqueous sodium hydroxide solution (100 mL) was added bromine (1.93 mL, 38.6 mmol) under ice-cooling, and 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione (5.20 g, 35.1 mmol) was subsequently added. 10%-Aqueous sodium hydroxide solution (60 mL) was added to the reaction mixture, and the mixture was stirred with heating at 90 C. for 40 min. After allowing to cool to room temperature, 50% sulfuric acid was added to adjust the reaction mixture to pH 3. The precipitated insoluble material was collected by filtration, and the solid was washed with water to give 3-aminoisonicotinic acid as a pale-yellow powder (5.00 g, 100%). 1H-NMR (200 MHz, DMSO-d6) delta: 7.46 (1H, d, J=5.1 Hz), 7.73 (1H, d, J=5.1 Hz), 8.21 (1H, s).

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:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
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Electric Literature of 17641-08-6,Some common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, 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 mixture of 4-(5-mercapto-1,3,4-oxadiazol-2-yl)benzenesulfonamide (9) (1mmol), various substituted 2-chloro-N-phenylacetamide 11a-j (1mmol) and K2CO3 (1.5mmol) was refluxed in acetone (15ml) for 3-4h. The reaction was monitored with TLC and after completion of the reaction, excess of solvent was evaporated and diluted with water (about 100ml). The precipitated was separated out, filtered washed with water and recrystallized with an appropriate solvent.

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-N-(3-methoxyphenyl)acetamide, its application will become more common.

Reference:
Article; Angeli, Andrea; Kumar, Rajiv; Sharma, Pawan K.; Sharma, Vikas; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 193; (2020);,
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Some common heterocyclic compound, 108-13-4, name is Malonamide, molecular formula is C3H6N2O2, 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. Recommanded Product: Malonamide

(1) Production of 1,2-dihydro-2-oxo-6-(trifluoromethyl)pyridine-3-carboxamide; Sodium methoxide (74g, 1.37 mol) was dissolved in methanol (1,000 mL), and malon diamide (100g, 0.979 mol) was added to this solution at room temperature. To this mixture, 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (191g, 1.14 mol) was added dropwise at a temperature between 25 and 30C, and the resultant mixture was refluxed under heating for 2 hours. After cooling to 45C, concentrated hydrochloric acid was added to the mixed solution to give a pH of 3 to 4, and 500 mL of methanol was distilled off at normal pressure. To the residue, water (500 mL) was added, and the mixture was stirred for a day at room temperature. The resultant product was precipitated while cooling with ice. Thus obtained crystal was collected by filtration, washed with water, and then dried under reduced pressure, to obtain 167g of a subject compound (yield: 83%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-13-4, its application will become more common.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1982978; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 2623-33-8, 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. 2623-33-8, name is 4-Acetamidophenyl acetate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 6 Preparation of 4-Acetoxy-2-nitroacetanilide (V) A 500 mL, Erlenmeyer flask equipped with a magnetic stirring bar and a thermocouple was charged with 4-acetoxyacetanilide (10.3 g, 0.05 mol), methylene chloride (50 mL), and acetic anhydride (16.2 g, 0.16 mol). The mixture was stirred at ambient temperature for 15 minutes (incomplete solution), and then was cooled to 0C (ice-salt bath). Nitric acid (5.0 mL, 0.08 mol, 70% acid, d=1.42) was added over a 30 second period. The ice bath was removed and the mixture was heated to boiling (42.5C) and maintained at that temperature for 30 minutes. The reaction temperature was slowly increased to 75C to distill methylene chloride, and then the mixture was allowed to cool slowly to ambient temperature and stand for 16 hours. The crystalline precipitate was isolated by filtration and vacuum dried to yield 7.1 g, 0.03 mol of 4-acetoxy-2-nitroacetanilide (mp 143-146C).

The synthetic route of 4-Acetamidophenyl acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IOLAB CORPORATION; EP282294; (1988); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

98-10-2, name is Benzenesulfonamide, belongs to amides-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. Recommanded Product: 98-10-2

General procedure: To a mixture of sulfonamide (2 mmol) and alcohol (10 mmol) in 1,4-dioxane (3 mL) was added Tf2O (2 mmol). The mixture was then sealed and stirred at 120 C until the reaction was completed as judged by TLC. After quenching with satd. aq. NaHCO3, the reaction mixture was extracted three times with EtOAc, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography with PE and EtOAc (3: 1) as the eluent to give the pure product.

The synthetic route of 98-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Ting Ting; Qi, Lan-Jun; Cui, Dong-Mei; Zhang, Chen; Zhao, Yan; Bulletin of the Chemical Society of Japan; vol. 88; 4; (2015); p. 610 – 612;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 24566-95-8, name is 1-(3-Aminopropyl)azepan-2-one, 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. name: 1-(3-Aminopropyl)azepan-2-one

General procedure: p-Chloro-N-alkylbenzenesulfonamides (1-8) (1 equiv.) andaminolactam N-(3-aminopropyl)-2-pyrrolidinone (APP)(1.25 equiv.) or N-(3-aminopropyl)-2-azepanone (APA)(1.25 equiv.) were added to a 50 mL round-bottomed flaskand dissolved in dimethylsulfoxide (10 mL) for a nucleophilicaromatic substitution reaction (SNAr). The contents were then stirred in a reflux system for 1-2 h at 85 C.Afterward, the solvent was removed with frozen water andthe product was treated with diluted HCl (5 %) for removalof amino-lactam excess. The crude product was filtered offand recrystallized from 1:1 ethyl ether-petroleum ether (bp60-80 C). All obtained compounds were structurally confirmedby 13C and 1H NMR analyses (see Supplementarymaterial).

The synthetic route of 1-(3-Aminopropyl)azepan-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Martins, Carina C.; Bassetto, Carlos A. Zanutto; Santos, Jandyson M.; Eberlin, Marcos N.; Magalhaes, Alvicler; Varanda, Wamberto; Gonzalez, Eduardo R. Perez; Amino Acids; vol. 48; 2; (2016); p. 445 – 459;,
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Reference of 5466-88-6, 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. 5466-88-6, name is 2H-1,4-Benzoxazin-3(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure for compound 26:; To a solution of compound 21 (3.0 gm, 20.1 mmol) in DMF, potassium carbonate (8.3 gm, 60.4 moles) was added followed by methyl iodide (2 mL, 30.1 mmol) at room temperature. The resulting mixture was stirred for 2 hrs at the same temperature. After completion of the reaction, the mixture was washed with ethyl acetate and water and the organic layer was dried over Na2S04 and concentrated under reduced pressure to obtain a residue which turned into a solid compound 26 (2.5 gm, 78.12% yield) on washing with pentane solvent. The obtained product was used for further step directly without purification.

The chemical industry reduces the impact on the environment during synthesis 2H-1,4-Benzoxazin-3(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; SALITURO, Francesco, G.; SAUNDERS, Jeffrey, O.; WO2012/88314; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1171331-39-7, name is 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride

To a stirred solution of (Z)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoic acid (200 mg, 0.41 mmol) in anhydrous THF (5.0 mL) was added carbonyldiimidazole (82 mg, 0.51 mmol). The mixture was heated in a 50 C. oil bath for 1.5 h, treated with 2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride (109 mg, 0.057 mmol) and the resulting mixture heated to reflux for 8 h. After cooling to ambient temperature, the mixture was taken up in Et2O and washed twice with aq. 5% NaHSO4 (2*) and once with sat. NaCl (1*). After dying over MgSO4, concentration in vacuo and purification by medium pressure chromatography on silica with EtOAc/Hexanes as the eluents, the title compound was obtained as a white foam (160 mg, 41%) mp 48-61 C.: 1H NMR (400 MHz, CDCl3) delta 7.58 (d, J=7.9 Hz, 1H), 7.44-7.29 (m, 3H), 7.14 (dd, J=7.9, 1.6 Hz, 1H), 6.86 (d, J=11.4 Hz, 1H), 6.76 (t, J=5.9 Hz, 1H), 6.59 (br s, 1H), 6.21-6.04 (m, 1H), 4.23 (d, J=5.5 Hz, 1H), 3.98 (qd, J=9.0, 6.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -69.31, -72.3; EIMS m/z 626.9 ([M+1]+).

According to the analysis of related databases, 1171331-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics