Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, belongs to amides-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 75175-77-8, Recommanded Product: 75175-77-8

General procedure: Formamidine acetate (9.9 g, 0.096 mol) and sodium ethoxide(10.9 g, 0.16 mol) were dissolved in ethanol at 70 C for 1 h. Then2a-i was added in the reaction solution slowly, refluxed for15-20 h and monitored by TLC. The solution was concentratedin vacuum, the residue was resolved with dichloromethane(300 mL), washed with brine (60 mL), dried over anhydrousNa2SO4, and concentrated in vacuum to give the light yellowsolids 3a-i.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, and friends who are interested can also refer to it.

Reference:
Article; Zhu, Wufu; Wang, Wenhui; Xu, Shan; Wang, Jianqiang; Tang, Qidong; Wu, Chunjiang; Zhao, Yanfang; Zheng, Pengwu; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1749 – 1756;,
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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, A new synthetic method of this compound is introduced below., Computed Properties of C4H8ClNO2

A solution of 2.5 M n-butyl lithium in hexanes (35ml, 87.6mmol) was added to a solution of the bromide from preparation 29 (20.0g, 79.7mmol) in ferf-butyl methylether (300ml) at -78¡ãC under nitrogen over 10 minutes. The reaction was stirred for a further 10 minutes and 2-chloro-N-methoxy-N-methyl-acetamide (12.1g, 87.6mmol) in terf-butyl-methylether (40ml) was added slowly. The reaction was stirred at -78¡ãC for 20 minutes and then 1M hydrochloric acid (200ml) was added. The mixture was allowed to warm to room temperature, stirred for 2 hours and the organic phase separated. The aqueous phase was extracted with fe/f-butyl methylether and the combined organic extracts were washed with water (100ml), saturated aqueous sodium chloride (100ml) and 1M sodium hydroxide (100ml). The organic phase was dried (sodium sulfate), concentrated in vacua and the residual oil purified by flash column chromatography on silica gel eluting with pentane:dichloromethane:methanol (75:25:0 changing to 0:99:1, by volume). The residue was recrystallised from pentane:dichloromethane to give the title compound as a yellow solid.1H NMR (400MHz, CDCI3): 5 = 9.11 (1H, s), 8.34-8.33 (1H, d), 7.32-7.30 (1H,d), 5.91 (2H, s), 4.66 (2H, s), 2.17 (6H, s) ppm.LRMS (electrospray): m/z [M-H]+ 247.

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; PFIZER LIMITED; PFIZER INC.; WO2004/108676; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 389890-42-0, name is tert-Butyl (trans-3-hydroxycyclobutyl)carbamate, molecular formula is C9H17NO3, 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 tert-Butyl (trans-3-hydroxycyclobutyl)carbamate

triethyl amine (6.8 g, 67.29 mmol) was added to a suspension of trans -tert-butyl -3- hydroxy cyclobutyl carbamate (4.2 g, 22.43 mmol) in DCM (100 mL) followed by dropwise addition of methanesulfonyl chloride (3.08 g, 26.91 mmol) at -10 C and the reaction mixture was stirred at -10 C for 2h. The reaction mixture was diluted with DCM (100 mL) and washed with water (50 mL) followed by brine (30 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product (3.4 g, crude) as a yellow solid which was used as such in next step without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 389890-42-0, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 5511-18-2, 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. 5511-18-2 name is Adamantane-1-carboxamide, 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: To a stirred solution of 13, 10k or 10m (130 mmol) in dried THF (150 mL) cooled in an ice-waterbath was added portionwise LiAlH4 (6.41 g, 169 mmol). Thereafter the reaction mixture was stirredat room temperature for 1 h and then at reflux for another 5 h, when the reaction completed asindicated by TLC analysis. On cooling to room temperature, the reaction mixture was carefullypoured into ice-water (500 mL) while stirring, and the resulting mixture was diluted with CH2Cl2(300 mL), stirred for 0.5 h and filtered off through Celite. The organic phase was separated from thefiltrate, and the aqueous phase was back-extracted with CH2Cl2 (200 mL ¡Á 2). The combined organicphases were washed with saturated brine (200 mL), dried (Na2SO4) and evaporated on a rotaryevaporator to give a residue, which was purified by column chromatography through a short silicagel column to afford 2d, 2k or 2m. These amines were used directly in the next step without furtherpurification and characterization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Adamantane-1-carboxamide, and friends who are interested can also refer to it.

Reference:
Article; Cai, Wenqing; Wu, Jingwei; Liu, Wei; Xie, Yafei; Liu, Yuqiang; Zhang, Shuo; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong; Molecules; vol. 23; 2; (2018);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, name is 4-(tert-Butyl)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. Quality Control of 4-(tert-Butyl)benzenesulfonamide

General procedure: Under the argon atmosphere, a Schlenk tube (15 mL) equipped with a magnetic bar was loaded with the sulfonamide 1 (0.5 mmol), sodium arylsulfinates 2 (0.6 mmol, 1.2 equiv.), Pd(MeCN)2Cl2 (6.5 mg, 5 molpercent) and AgOAc (166.9 mg, 1.0 mmol) in one portion. Then, the mixture of 1,4-dioxane/DMSO (3.5 mL in a 9:1 ratio) was added to obtain a clear solution and the reaction mixture was allowed to stir at 120 ¡ãC for 24 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a petroleum ether and ethyl acetate (3/1) as eluent to give the N-aryl sulfonamides 3 in noted yields.

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Zijian; Lian, Yan; Zhao, Chang; Wang, Bing; Synthetic Communications; vol. 48; 12; (2018); p. 1436 – 1442;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 198967-24-7,Some common heterocyclic compound, 198967-24-7, name is 2-Fluoro-N-methoxy-N-methylbenzamide, molecular formula is C9H10FNO2, 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 solution of 2-fluoro-N-methoxy-N-methylbenzamide (16 g, 87.4 mmol) in THF (150 mL) was cooled to -78 C. Vinylmagnesium bromide (120 mL, 120 mmol) was slowly added, and the mixture stirred at -78 C. for 10 min, slowly warmed to rt, and stirred for another 3 h. The reaction mixture was quenched with 1 N aq HCl (100 mL) at 0 C. The aqueous layer was extracted with EtOAc (100 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography to afford 1-(2-fluorophenyl)-prop-2-en-1-one (7.6 g, yield: 58.4%) 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 2-Fluoro-N-methoxy-N-methylbenzamide, its application will become more common.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 104863-65-2, name is N-Methoxy-N-methylpropionamide, belongs to amides-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 104863-65-2, COA of Formula: C5H11NO2

n-Butyllithium (1.6 M solution in hexanes; 28.9 ml) was added dropwise under nitrogen at 0 C. to a stirred solution of benzo[b]thiophene (6.21 g) in ether (90 ml), then the mixture was stirred 0 C. for 15 minutes and cooled to -70 C. A solution of N-methoxy-N-methylpropionamide (5.42 g) in ether (40 ml) was added over 10 minutes, then the mixture was allowed to warm to ambient temperature and was stirred at ambient temperature for 3.5 hours. The mixture was poured into saturated aqueous ammonium chloride solution (200 ml) and ethyl acetate (100 ml) and water (50 ml) were added. The organic phase was separated, washed with saturated aqueous sodium chloride solution (150 ml), dried (Na2SO4) and the solvents were removed in vacua. The residue was triturated with petroleum ether (b.p. 40-60 QC) (25 ml) and the resulting solid was collected by filtration and dried in vacuo to give 1-(benzo[b]thiophen-2-yl)propan-1-one (7.05 g) as a colourless solid, m.p. 79-81 C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Doyle, Kevin James; Kerrigan, Frank; Watts, John Paul; US2003/166628; (2003); A1;,
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. 1746-77-6, name is Isopropyl carbamate, A new synthetic method of this compound is introduced below., SDS of cas: 1746-77-6

Intermediate 4 1-Methylethyl(2E)-2-butenoylcarbamate Isopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3 L Lara vessel and dry THF (150 ml) added. (2E)-2-Butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to -30 C. When the solution temperature reached -17 C. lithium tert-butoxide (1M, 655 ml, 655 mmol) was added by peristaltic pump over 2 h, keeping the reaction temperature between -10 C. and -18 C. Once the addition was complete the mixture was stirred for 30 min and brought to 0 C. Diethyl ether (450 ml) and hydrochloric acid (1M, 375 ml) were added and the mixture brought to 20 C. with vigorous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375 ml) was added and the mixture stirred vigourously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (MgSO4), filtered and evaporated to a brown oil (60 g). The oil was applied to a silica column (40+M Biotage) and eluted with DCM/ethyl acetate (1:1 to 0:1, 10 CV). The product containing fractions were evaporated to dryness and loaded on to a silica column (1500 g, Redisep Isco) and eluted with a ethyl acetate in cyclohexane gradient (0-40%). The clean, product containing fractions were evaporated to an off-white solid (15.41 g). LCMS (Method C), Rt 0.68, MH+172

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; GlaxoSmithkline LLC; Amans, Dominique; Demont, Emmanuel Hubert; Jones, Katherine Louise; Seal, Jonathan Thomas; Walker, Ann Louise; US2014/66459; (2014); A1;,
Amide – Wikipedia,
Amide – 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 956434-30-3 as follows. Application In Synthesis of tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

(Step 1) To a solution of the compound (0.500 g) obtained in Example 29, step 1 and iron(III) acetylacetonate (0.0620 g) in a mixture of THF (10 mL) and 1-methylpyrrolidinone (1 mL) was added 1M isopropylmagnesium chloride ether solution (8.78 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 1N hydrochloric acid, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5?100% ethyl acetate/hexane) to give tert-butyl 8-isopropyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.136 g, 27%) as an oil. 1H-NMR(CDCl3): delta 1.27(6H,d,J=7.0Hz), 1.42(9H,s), 2.93-3.02(1H,m), 3.82-3.84(2H,m), 4.22(2H,brs), 4.35-4.50(2H,m), 6.88(1H,d,J=7.5Hz), 7.40-7.60(1H,m) MS(ESI+):293(M+H)

According to the analysis of related databases, 956434-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 72179-84-1, These common heterocyclic compound, 72179-84-1, name is (Methylsulfamoyl)amine, 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: N-Alkylsulfamide 7 (3.63mmol, 1equiv) was added to a stirred solution of arylaldehyde (4.00mmol, 1.1equiv) and Ti(OEt)4 (1.95g, 7.26mmol, 2equiv) in THF (10mL). The solution was stirred at reflux for 7h, allowed to cool and then poured into stirred brine (100mL), EtOAc (50mL) was added and the mixture was stirred vigorously. The mixture was then filtered through Celite and flushed with further EtOAc. The filtrate was separated and the aqueous layer was back extracted with EtOAc (50mL). The combined organic layers were washed with brine (50mL), dried (Na2SO4) and concentrated to a cream solid. Purification by column chromatography or trituration gave the products as colourless to cream solids (yellow for 9f).

Statistics shows that (Methylsulfamoyl)amine is playing an increasingly important role. we look forward to future research findings about 72179-84-1.

Reference:
Article; Crampton, Rosemary H.; Fox, Martin; Woodward, Simon; Tetrahedron Asymmetry; vol. 24; 9-10; (2013); p. 599 – 605;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics