Author: Jessica.F

Application of 72505-21-6, 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. 72505-21-6 name is 4-(Trifluoromethyl)thiobenzamide, 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.

General procedure: A solution of 3-bromo-1-benzofuran-2(3H)-one (0.5 g,2.35 mmol) in toluene (5 mL) was added dropwise to a suspensionof the corresponding thioamide (2.35 mmol) and pyridine (65 mL,0.8 mmol) in toluene (5 mL) at room temperature. The reactionmixturewas stirred and heated at 80C for 2 h and then cooled. The amorphous precipitate was collected by filtration and thenrecrystallized from 80% aqueous ethanol to give products 1a-h as orange crystals. Alternative method for synthesis of 1a is alsodescribed in Ref. [25].

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

Reference:
Article; Kammel, Richard; Tarabova, Denisa; Machalicky, Old?ich; Nepra?, Milo?; Frumarova, Bo?ena; Hanusek, Ji?i; Dyes and Pigments; vol. 128; (2016); p. 101 – 110;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 20348-09-8, 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. 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 2H-pyrido[3,2-b][1 ,4]oxazin-3(4H)-one (45.0 g, 300 mmol) in DMF (360 mL) at 20 C was added NBS (74.7 g, 420 mmol) in one portion, and the resulting brownish suspension was heated at 50 C for 20 hours. The mixture was cooled to 25 C, and the content was poured into stirred water (1 L) in a 3 L flask fitted with an overhead mechanical stirrer. The resulting aqueous suspension was stirred at room temperature for 30 minutes followed by filtration. The yellowish cake was washed with 10% Na2S203 solution (100 mL) followed by water (2 x 100 mL). The cake was aspirated at room temperature under house vacuum overnight. The solids were washed with Et20 (100 mL), aspirated under house vacuum at room temperature for 18 hours, and then dried under high vacuum at 50 C for 72 hours to afford the title compound (65.30 g) as a light tan-colored powdery solid. LC-MS (ES) m/z = 229, 231 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 4.68 (s, 2H), 7.66 (d, J = 2.0 Hz, 1 H), 8.02 (d, J = 2.0 Hz, 1 H), 1 1 .44 (br. s., 1 H).

The synthetic route of 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 5900-59-4,Some common heterocyclic compound, 5900-59-4, name is 2-Amino-4-chlorobenzamide, molecular formula is C7H7ClN2O, 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.

EXAMPLE A To a mixture of 0.34 g of 2-amino-4-chlorobenzamide, 0.57 g of monochloroacetic acid, 0.90 g of sodium iodide and 0.24 g of magnesium oxide was added 2 ml of dimethylformamide and the mixture was stirred at a temperature between 90¡ã and 100¡ã C. for 2.5 hours. After cooling, the reaction mixture was poured into 50 ml of a 2.6percent aqueous sodium carbonate solution. The resulting precipitates were filtered off and the filtrate was extracted with 50 ml of chloroform. The aqueous layer was acidified with concentrated hydrochloric acid to precipitate crystals. The crystals were collected by filtration and recrystallized from aqueous methanol to obtain 0.20 g of N-(2-carbamoyl-5-chlorophenyl)glycine as needles having a melting point of 217¡ã-222¡ã C. (decomposition). Elemental Analysis for C9 H9 O3 N2 Cl: Calcd.(percent): C, 47.28; H, 3.97; N, 12.25. Found (percent): C, 47.11; H, 3.74; N, 12.32.

The synthetic route of 5900-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Seiyaku Co., Ltd.; US4297357; (1981); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 864448-41-9, These common heterocyclic compound, 864448-41-9, name is tert-Butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate, 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 solution tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate (400mg, L75 mmol) and Et3N (0.49 niL, 3.5 mrnol) in DCM (10 mL) was added CbzCl (448 mg, 2.63 mmoi) at room temperature. The reaction mixture was stirred at room temperature for 2 hours and then water (10.0 mL) was added, and the mixture is extracted three times with EtOAc (30 rnL each). The combined organic phase was dried over Na2SO4 and concentrated. The residue was purifiedby silica gel colunm chromatography (PE: EtOAc, from 10:1 to 2: 1) to give a white solid (300 mg). The solid was dissolved in ACN (8 mL) and water (2 rnL), to which were added RuC13 (35 mg, 0.170 mmol) and Na104 (532 mg, 2.48 mmoi). The reaction mixture was stirred at room temperature for 36 hours and water (10 niL) was added, and the mixture was extracted three times with EtOAc (20 mL), The combined organic phase was dried over Na2SO4 andconcentrated. The residue was purified by column (PE: EtOAc, from 10:1 to 1: 1) to give the desired product 13a as a yellow oil (150 mg). LCMS (M-100+H) 277.1

The synthetic route of 864448-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; KOU, Buyu; LIU, Haixia; ZHANG, Zhisen; ZHOU, Zheng; (54 pag.)WO2018/11162; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 16982-21-1,Some common heterocyclic compound, 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, molecular formula is C4H7NO2S, 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 mixture of 1-bromo-3-methylbutan-2-one (1.1 g, 6.66 mmol), ethyl thioxamate (600 mg, 4.51 mmol) in 5.0 mL ethanol was refluxed overnight. After the completion of the reaction the solvent was removed and the crude mixture was dissolved in ethyl acetate. The organic layer was washed with water, brine and was dried under sodium sulfate. Evaporation of the solvent produced the desired product mixed with impurities which was used for the next step without further purification (400 mg, 30% yield).

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

Reference:
Patent; LaVoie, Edmond J.; Parhi, Ajit; Pilch, Daniel S.; Zhang, Yongzheng; Kaul, Malvika; US2015/133465; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 125414-41-7, 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 125414-41-7 as follows.

2-(tert-butoxycarbonylamino)propane-l ,3-diyl ditetradecanoate To a solution of tetradecanoic acid (1.051 g) in dichloromethane (10 mL) at 00C were added tert-butyl l,3-dihydroxypropan-2-ylcarbamate (0.40 g), 4-(dimethylamino)pyridine (0.562 g), N-methylmorpholine (1.150 mL), and l-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (0.882 g). The mixture was stirred at room temperature overnight. The mixture was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane. The extract were dried over Na2SO4, filtered, and concentrated. The concentrate was purified by flash chromatography (1 :10 ethyl acetate/hexanes). MS (ESI) m/z 512.4 (M-CO2-tert-butyl+l)+.

According to the analysis of related databases, 125414-41-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/129385; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 14062-80-7,Some common heterocyclic compound, 14062-80-7, name is 4-Chloro-N,N-dimethylbenzamide, molecular formula is C9H10ClNO, 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.

N’-cyanobenzimidamide (16.8 g, 115 mmol),Compound A-2 (21 g, 115 mmol) and phosphorous oxychloride(12 mL, 128 mmol) was added to 500 mL of acetonitrile, followed by stirring and refluxing for 1 hour.After cooling to room temperature, the resulting solid was filtered,Washed with water and ethanol, and then dried to obtain CompoundA (27.6 g, yield 80%).

The synthetic route of 14062-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Kang Min-yeong; Park Tae-yun; Cho Seong-mi; Moon Jeong-uk; Jeong Min-u; Lee Jeong-ha; (29 pag.)KR2019/6353; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 14719-21-2, 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 14719-21-2 as follows.

F1 (0.7 mmol, 247 mg) was added to a single-necked flask and 9.7 mg CuI and 20.3 mg Pd (PPh3) 4 (tetrakistriphenylphosphine) palladium were weighed into a reaction flask. The reaction flask was evacuated, purged with nitrogen and wrapped in aluminum foil , 2.3 ml DMF was added,Stirring to dissolve, adding 0.2ml TEA, weighing F2 (254mg, 1.7mmol) dissolved in DMF was added to the above reaction flask, stirred at room temperature, the reaction overnight.TLC plate monitoring, EA as developing solvent, Rf = 0.35 as the raw material F1, Rf = 0.32 for the product F3, two very close position.After the reaction was over, the solvent was evaporated to dryness under reduced pressure and the residue was directly purified by column chromatography. Elution with 20: 1 DCM: MeOH as eluant gave 214 mg, yield 61%.

According to the analysis of related databases, 14719-21-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Jiao Tong University; Shen Yumei; Gong Bing; Shao Zhifeng; Zhao Xiaodong; Liu Yazhi; Li Xiaowei; Wu Xinyan; Wei Xiaofei; Tang Daonian; (99 pag.)CN104292117; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39549-79-6, name is 2-Amino-4-methylbenzamide, molecular formula is C8H10N2O, 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. category: amides-buliding-blocks

General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2mol%), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2¡Á5mL) and acetone (2¡Á5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39549-79-6, its application will become more common.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 88-19-7, name is 2-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Formula: C7H9NO2S

{3-[2-methoxy-4-carboxy-benzyl]-1-methyl-1H-indol-5-yl}-carbamic acid cyclopentyl ester (7 kg), dimethyl amino pyridine (2.5 kg), dicyclohexyl carbodiimide (3.9 kg), and dichloromethane (70 L) are charged and stirred for about 15 minutes. O-toluene sulphonamide (3.4 kg) is added at 30 C. and the reaction solution is stirred for about 4 hours at 30 C. The unwanted separated solid is filtered and the reaction solution is washed with dichloromethane (2¡Á12 L). The obtained organic layer is washed with dilute hydrochloric acid and water and separated. The obtained organic solution is distilled off completely under vacuum below 45 C. Acetonitrile (14 L) is added and distilled off completely under vacuum. The obtained crude is cooled to 30 C., acetonitrile (35 L) is added and heated to 85 C., and stirred for about 40 minutes. The resultant reaction solution is cooled to 35 C. and stirred for about 55 minutes. The separated solid is filtered, washed with acetonitrile (7 mL), and suction dried for about 30 minutes. The obtained wet compound is again charged into a reactor containing methanol (84 L), heated to about 60 C., and stirred for about 30 minutes. The reaction solution is cooled to 30 C. and stirred for about 50 minutes for solid separation. The obtained solid is filtered, washed with methanol (7 L), and suction dried for 30 minutes. The solid is dried under vacuum at 70 C. for about 4 hours to afford the title compound.HPLC Purity: 97.5%

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; Anumula, Raghupathi Reddy; Gilla, Goverdhan; Alla, Sampath; Kurella, Sreenivasulu; Kopparapu, Janardana Sarma Ramachandra; Medisetti, Rama Krishna Venkata; Maddula, Srinivasula Reddy; US2009/149662; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics