Tag: M.W=100-200

Reference of 6274-22-2,Some common heterocyclic compound, 6274-22-2, name is 4-Amino-N-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.

General procedure: CS2 (50 mL) was added to a stirring mixture of DABCO (30 mmol) and amine (10 mmol) in acetone (10 mL). The resulting mixture was further stirred at room temperature to achieve dithiocarbamate, and the process of the reaction was monitored by TLC. After completion of the reaction, the solution was filtered and the solid was washed with acetone. After it was dried in an infrared-ray oven, the salt was dissolved in dried CHCl3 (10 mL) and the mixture was chilled to 0-5 C in an ice bath. BTC (1010 mg, 3.4 mmol), dissolved in CHCl3 (5 mL), was added dropwise for 30 min with constant stirring. The reaction mixture was then allowed to reach room temperature and stirred for a further 4 h. Triethylenediammmonium hydrochloride was filtered off, and the filtrate was evaporated in vacuo to afford the desired isothiocyanate in good purity. All products were identified by comparison with authentic samples.

The synthetic route of 6274-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Pengfei; Li, Chunyan; Zhang, Jingwei; Xu, Xiaoyong; Synthetic Communications; vol. 43; 24; (2013); p. 3342 – 3351;,
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Electric Literature of 5349-24-6, 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. 5349-24-6, name is N-Butyl-2-chloroacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Various substituted anilines were dissolved in glacial acetic acid at0 C, to this was added over 30 min choloroacetyl chloride (2 equivalents).The reaction mixture was brought to room temperature andstirred overnight. Saturated sodium bicarbonate solution was added tillcomplete neutralization. The resulting precipitate was filtered off andwashed with n-hexane and dried. The resultant product (1) was usedfurther without any purification. Either of 4-hydroxy benzaldehyde(2a), vanillin (2b) or isovanillin (2c) (1 equivalent) was dissolved inacetone and potassium carbonate (2 equivalents) was added. Thencorresponding substituted acetamide (1) was mixed to the stirring solution.Finally, potassium iodide (1.5 equivalent) was added. The reactionmixture was refluxed for 8-10 h. After completion of reaction,the resultant mixture was concentrated and treated with water andextracted with ethyl acetate (3×20 mL). The organic layers werecombined and treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel (60-120)using petroleum ether: ethyl acetate (9:1).

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-Butyl-2-chloroacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sonawane, Vinay R.; Siddique, Mohd Usman Mohd; Gatchie, Linda; Williams, Ibidapo S.; Bharate, Sandip B.; Jayaprakash, Venkatesan; Sinha, Barij N.; Chaudhuri, Bhabatosh; European Journal of Pharmaceutical Sciences; vol. 131; (2019); p. 177 – 194;,
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These common heterocyclic compound, 104863-65-2, name is N-Methoxy-N-methylpropionamide, 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. SDS of cas: 104863-65-2

Cool a solution of 1-bromo-2-methyl-4-(trifluoromethyl)benzene (2.00 g, 8.367 mmol) and THF (17 mL) to -71 C., and then add n-butyl lithium (2.5 M in hexanes, 9.204 mmol, 3.681 mL) over 5 minutes. Stir the mixture for 15 minutes at -71 C. Add N-methoxy-N-methylpropanamide (0.980 g, 8.367 mmol) to the mixture drop-wise over 3-4 minutes keeping temperature below -65 C. Continue to stir the solution at -71 C. for 15-20 minutes; then warm the solution to room temperature. Stir at room temperature for 40 minutes. Quench the reaction with a saturated ammonium chloride aqueous solution. Extract the aqueous layer with Et2O. Wash the combined organic extracts with water and brine. Dry the mixture over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the residue by flash chromatography (40 g RediSep column) eluting with a gradient of 0-40% DCM/pentane to give the title compound as a colorless oil (1.490 g, 82% yield). 1H NMR (399.80 MHz, d6-DMSO) delta 7.84 (d, J=7.8 Hz, 1H), 7.64-7.61 (m, 2H), 2.93 (q, J=7.1 Hz, 2H), 2.39 (s, 3H), 1.03 (t, J=7.2 Hz, 3H).

The synthetic route of N-Methoxy-N-methylpropionamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; US2012/302608; (2012); 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. 78191-00-1, name is N-Methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 78191-00-1

To a solution of l-bromo-3-isopropylbenzene (10 g, 0.05 niol) in THF was added dropwise with BuLi (47 mL, 0.075 mol) at -60C. After stirred 30 minutes, -methoxy- -methylacetamide (6,22 g, 0.06 mol) was added. The mixture was stirred at -30C for 3 hours. Then the mixture was quenched with H20, the mixture was partitioned between EtOAc and water. The layer was separated and washed with water, brine, dried over Na2S04, and concentrated. The residue was purified by column chromatography to obtained the titled compound. ‘H NMR (CHLOR OFQRM-d) : delta 7.85 (s, 1H), 7.79 (dt, J = 7.6, 1.4 Hz, 1H), 7.33 – 7.53 (m, 2H), 3.00 (dt, J – 13.8, 6.9 Hz, 1H), 1.30 (d, J – 6.7 Hz, 6H) LC-MS : m/z 163(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 78191-00-1.

Reference:
Patent; RIPKA, Amy S.; SAUNDERS, Jeffrey O.; KAMENECKA, Theodore Mark; GRIFFIN, Patrick R.; WO2013/78240; (2013); A1;,
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Electric Literature of 5238-56-2,Some common heterocyclic compound, 5238-56-2, name is N-(2-Hydroxyethyl)methacrylamide, molecular formula is C6H11NO2, 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-(2-hydroxyethyl) methacrylamide (3.30 mL, 25.6 mmol, 1.0 eq), triethylamine (7.15 mL, 51.2 mmol, 2.0 eq) and 50 mL DCM were added into a 250 mL flask. After the reaction system was cooled down by an ice bath, butyric anhydride (5.00 mL, 30.7 mmol, 1.2 eq) was added dropwise under the protection of nitrogen. The system was allowed to react overnight. The reaction mixture was filtered and washed by NH4CI solution, NaHCCb solution, and water. After dried by anhydrous MgSC , the organic layer was concentrated by rotary evaporation and purified on a silica column using DCM/MeOH. The product N- butanoyloxyethyl methacrylamide (3) was obtained as pale yellow oil (4.56 g, 89.6%) and analyzed by 1H-NMR (500 MHz, CDCb) deltaEta ppm 0.95 (t, 3H, CH2CH2-CH3), 1.66 (m, 2H, CH2-CH2), 1.97 (s, 3H, C(CH2)-CH3), 2.32 (t, 2H, CO-CH2), 3.59 (dt, 2H, NH-CH2), 4.23 (t, 2H, O-CH2), 5.35 (s, IH, CCH2), 5.71 (s, IH, CCH2), 6.19 (br s, IH, NH). This example demonstrates the feasibility of attaching pharmaceutically-active small molecules to a monomeric unit of the block copolymer. Additional SCFAs can be attached to the monomeric unit in a similar manner.

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

Reference:
Patent; THE UNIVERSITY OF CHICAGO; HUBBELL, Jeffrey A.; WANG, Ruyi; WILSON, D. Scott; NAGLER, Cathryn R.; PLUNKETT, Catherine; (90 pag.)WO2018/195067; (2018); A1;,
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Application of 116861-31-5, The chemical industry reduces the impact on the environment during synthesis 116861-31-5, name is tert-Butyl (3-chloropropyl)carbamate, I believe this compound will play a more active role in future production and life.

[0095] Berbamine dihydrochloride (7.0 g, 10.28 mmol) is dissolved in N,N-dimethyl formamide (150 mL). Under nitrogen atmosphere, the solution is cooled to 0 C. After adding NaH (1.65 g, 60%, 41.12 mmol) into the solution, the mixture is stirred for 1 hour, then the solution of compound (8-2) (2.18 g, 11.3 mmol) in N,N-dimethyl formamide (30 mL) is added dropwise therein over 15 minutes. After being stirred for 1 hour at 0 C., the mixture is allowed to be warmed up to room temperature and is stirred for 3 hours, then is heated to 80 C. overnight. After vacuum evaporation, the reaction mixture is diluted with water and extracted with dichlorometbane (3*150 mL). The combined organic phase is washed with water and brine, dried through, anhydrous sodium sulfate and filtered. After vacuum concentration, the residue is purified by a preparative high performance liquid chromatography to give compound (8-3) (3.0 g, 38.1%).

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 (3-chloropropyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANGZHOU BENSHENG PHARACEUTICALS CO., LTD.; Xu, Rongzhen; Xie, Fuwen; Lai, Hongxi; Rong, Frank; US2013/178470; (2013); A1;,
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Electric Literature of 142-26-7, A common heterocyclic compound, 142-26-7, name is N-Acetylethanolamine, molecular formula is C4H9NO2, 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.

The title product of Preparation 29 (600 mg, 2.16 mmol), N-(2-hydroxyethyl)acetamide (276 mg, 2.68 mmo), triphenylphosphine (710 mg, 2.71 mmol) were mixed under Ar atmosphere followed by the addition of dry THF (5 ml). The mixture was cooled at 0 and DIAD was added drop wise. The reaction mixture was allowed to warm to rt and then stirred overnight. Solvent was removed and the residue thus obtained was partitioned between water and ethyl acetate. The organic layer was washed with water and brine. It was dried and solvent removed to yield a crude product that was purified according to purification method A to yield the title compound as a solid. 130 mg (17% yield) of the title product were obtained as a solid.LRMS: m/z 363 (M+1fRetention time: 4.32 min (method B)H NMR (200 MHz, DMSO-D6) delta ppm 0.92 (t, 3 H) 1.29 – 1.45 (m, 2 H) 1.55 (d,J=7.14 Hz, 2 H) 1.77 (s, 3 H) 2.20 (s, 6 H) 3.06 (t, J=6.59 Hz, 2 H) 3.24 – 3.45(m, 2 H) 3.85 – 4.01 (m, 2 H) 7.23 (s, 2 H) 7.96 – 8.07 (m, 1 H) 8.85 – 8.93 (m, 1H)

The synthetic route of 142-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; GRIMA POVEDA, Pedro Manuel; AGUILAR IZQUIERDO, Nuria; MIR CEPEDA, Marta; CARRASCAL RIERA, Marta; TERRICABRAS BELART, Emma; GRACIA FERRER, Jordi; CASALS COLL, Gaspar; WO2011/35900; (2011); A1;,
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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. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H10ClNO2

2) 2-chloro-N-(3-methoxyphenyl)acetamide (3.1g, 16 mmol) and anhydrous AlCl3 powder (4.4g,32 mmol) is heated and stirred at 120C for 10 minutes and exhibit a melting state. The temperature is elevated gradually to 240C in 40 minutes and then stirred 5 minutes. The reaction is allowed to cool to obtain a brown powder. The solid powder is poured into a mixture of 100g of crushed ice and 50ml of concentrated hydrochloric acid. The mixture is stirred for 10 minutes and then reflux for 10 minutes, and allowed to cool to precipitate a light yellow powder, which is filtered out and recrystallized in water to obtain 1.5g of 6-hydroxy-indoline-2-one, with a yield of 62%.

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; Jiangsu Guohua Investment Co., Ltd; Shanghai Institute of Pharmaceutical Industry; EP2322520; (2011); A1;,
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Synthetic Route of 63920-73-0, 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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-picolinaldehyde (13.10 g, 32.46 mmol) and 2-amino-4,6-dimethoxybenzamide (6.68 g, 34.08 mmol) in N,N-dimethylacetamide (150 ml) was added NaHSO3 (8.90 g, 48.69 mmol) and p-toluenesulfonic acid monohydrate (6.17 g, 32.46 mmol). The reaction mixture was stirred at 120 C. for 14 h. After that time the reaction was cooled to rt, concentrated under reduced pressure, diluted with saturated Na2CO3 (150 mL) and the precipitated solids were collected by filtration, washed with water and dried under vacuum. The product was washed with diethyl ether and dried to give 2-(5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (17.38 g, 92%) as light yellow solid: ESI MS m/z 580 [M+H]+.

The synthetic route of 2-Amino-4,6-dimethoxybenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; Fairfax, David John; Martin, Gregory Scott; Quinn, John Frederick; Duffy, Bryan Cordell; Wagner, Gregory Steven; Young, Peter Ronald; US2014/140956; (2014); A1;,
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Synthetic Route of 1943-79-9,Some common heterocyclic compound, 1943-79-9, name is Phenyl methylcarbamate, molecular formula is C8H9NO2, 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.

Phenyl N-methylcarbamate (350 mg, Production example 2-1) was added to a solution of 4-(3-methyl-1H-5-indolyl)oxy-2-pyridinamine (500 mg), sodium hydride (93 mg) and N,N-dimethylformamide (5 ml) at room temperature; and the reaction mixture was stirred for 2 hours and 45 minutes. Water was added to the reaction mixture; extraction was performed with ethyl acetate; and purification was performed by NH-silica gel column chromatography (Fuji Silysia, hexane: ethyl acetate = 1: 2, sequentially, ethyl acetate) to yield the title compound as a pale yellow amorphous solid (365 mg). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 2.19 (3H, s), 2.80 (3H, d, J=4.0 Hz), 5.73 (1H, d, J=2.4 Hz), 5.83 (2H, s), 6.12 (1H, dd, J=5.6, 2.4 Hz), 7.00 (1H, dd, J=8.8, 2.4 Hz), 7.27 (1H, d, J= 2.4 Hz), 7.64 (1H, s), 7.75 (1H, d, J=5.6 Hz), 7.98 (1H, q, J=4.0 Hz), 8.24 (1H, d, J=8.8 Hz).

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

Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); A1;,
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