Category: amides-buliding-blocks

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. 5349-24-6, name is N-Butyl-2-chloroacetamide, A new synthetic method of this compound is introduced below., Quality Control of N-Butyl-2-chloroacetamide

General procedure: The reaction mixture of N-substituted-2-chloroacetamide 2 (5.0 mmol, 1.0 equiv), crude product of 2-bromo-4-(substituted methyl)phenol 7 (5.0mmol, 1.0 equiv) and K2CO3 (7.5 mmol, 1.0 equiv) in MeCN (40 mL) was refluxed and monitored by TLC. When the reaction was accomplished, the solvents were removed under vacuum. To the obtained residue, water (50 mL)was added. The mixture was then extracted by ethyl acetate (3 x 50 mL), and the combined organic layers were dried over MgSO4. Removal the MgSO4 and evaporation of the solvent at reduced pressure gave the crude product. The pure product 8 was obtained by column chromatography on silica gel (elute: ethyl acetate: petroleum = 1: 4).

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:
Article; Xia, Shuai; Liu, Ji-Qiang; Wang, Xiu-Hua; Tian, Ye; Wang, Yu; Wang, Jing-Huan; Fang, Liang; Zuo, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1479 – 1483;,
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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. 24167-51-9, name is 3-Bromo-N,N-dimethylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 24167-51-9

General procedure: The following experimental procedure for the chemoselective partial reduction of ethyl benzoate and N,N-dimethyl 3-toluamide is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with ethyl benzoate (0.07mL, 0.5mmol), N,N-dimethyl 3-toluamide (0.08mL, 0.5mmol) and 5mL THF. After CDBBA (9.01mL, 0.44M soln. 4.0mmol) was slowly added and stirred for 12h at room temperature. The reaction was quenched by aqueous 1N HCl (10mL) and extracted with diethyl ether (2¡Á10mL). The combined organic layers were dried over MgSO4. GC analysis showed a 97% recovery yield of ethyl benzoate and 95% yield of 3-methylbenzaldehyde. All products in Table 2 were confirmed through comparison with GC data of authentic sample.

According to the analysis of related databases, 24167-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Im, So Hee; Shin, Won Kyu; Jaladi, Ashok Kumar; An, Duk Keun; Tetrahedron Letters; vol. 59; 24; (2018); p. 2335 – 2340;,
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Synthetic Route of 10268-06-1, The chemical industry reduces the impact on the environment during synthesis 10268-06-1, name is 2-(2-Chlorophenyl)acetamide, I believe this compound will play a more active role in future production and life.

A mixture of Compound 1c (322 mg, 0.857 mmol) and Compound 1d (121 mg, 0.714 mmol) in 7 ML of anhydrous THF was stirred under nitrogen and cooled in an ice bath while treating dropwise with 2.9 ML of 1 N potassium t-butoxide in THF. The mixture was stirred for 30 minutes in an ice bath then at room temperature for another 30 min.The reddish mixture was then cooled down and then 2 ML of concentrated HCl was added dropwise.The mixture was stirred for 5 min.ethyl acetate (150 ML) and H2O (30 ML) were added.The organic layer was separated and washed with saturated NaHCO3 and brine, dried over anhydrous sodium sulfate and concentrated in vacuo.The crude product was separated by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, from 98:2:0.2 to 95:5:0.5) to yield 150 mg (55percent) of Compound 1 as a yellow solid. 1H NMR (CDCl3) delta 8.21 (dd, J=1.5, 4.7 Hz, 1H), 8.17 (s, 1H), 7.48-7.33 (m, 4H), 6.78 (dd, J=4.7, 8.1 Hz, 1H), 6.66 (dd, J=1.5, 8.1 Hz, 1H), 4.5 (dd, J=2.6, 7.1 Hz, 2H), 3.41 (t, J=5.5 Hz, 2H), 2.03 (m, 2H). ES-MS m/z 382 (MH+). Using the procedure of Example 1 and the appropriate reagents and starting materials known to those skilled in the art, other compounds of the present invention may be prepared including, but not limited to

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

Reference:
Patent; Zhang, Han-Cheng; Kuo, Gee-Hong; Maryanoff, Bruce E.; Ye, Hong; O’Neill, David; Shen, Lan; Demarest, Keith; Conway, Bruce R.; McComsey, David F.; US2004/6095; (2004); A1;,
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Some common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, molecular formula is C3H6ClNO, 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 2-Chloro-N-methylacetamide

To a solution of bumetanide 32-1 (2.5 g, 6.86 mmol) in N,N-Dimethylformamide (25 mL) were added tri ethyl amine (1.4 mL, 10.2 mmol), Nal (1 .13 g, 7.5 mmol) and 2-Chloro-N-methyl-acetamide 32-2 (0.88 g, 8.23 mmol) at 0-5 C. The reaction mixture was allowed to stir at 50 C for lOh. The reaction mass was diluted with ethyl acetate (300 mL) and washed with water (2 X 100 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product obtained upon evaporation of volatiles was purified by silica gel (230-400 mesh) column chromatography to give product Compound 25 as an off white solid 1.8 g (60%). 1H NMR (400 MHz, DMSO-de) d 8.09 (q, 1H), 7.74 (d, J = 2 Hz, 1H), 7.47-7.35 (m, (0926) 3H), 7.27 (t, j = 8 Hz, 2H), 7.02 (t, J = 8 Hz, i l l), 6.85 (d, J = 8 Hz, 2H), 5.18 (t, 1H), 4.73 (s, 21 1 > 3.12-3.01 (m, 2H), 2.64 (d, 31 1). 1.37 (quintet, 2H), 1.11 (sextet, 2H), 0.77 (t, 3H); MS m/z [M+H]+ 436.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 96-30-0, its application will become more common.

Reference:
Patent; GRAYBUG VISION, INC.; YANG, Ming; BAUMAN, John, G.; ZHANG, Jinzhong; HOANG, Nu; CLELAND, Jeffrey, L.; (355 pag.)WO2019/210215; (2019); 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. 2603-10-3, name is Methyl N-Phenylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2603-10-3

General procedure: The urethane 1 (0.66 mmol) was dissolved in dry toluene (2 mL). The alcohol (3 equiv, 1.98 mmol) and the base (1.2 equiv,0.79 mmol) were added and the reaction mixture was heated at 60C with continuous agitation during 20h. To isolate thepure product, water (10 mL) and ethyl acetate (10 mL) were added to the reaction mixture. The organic layer was separated,dried on magnesium sulfate and the solvent was evaporated. The residue was purified by silica column chromatographyeluting with a 10-50% ethyl acetate/cyclohexane gradient. The fractions were concentrated under reduced pressure to givethe desired product 2.

According to the analysis of related databases, 2603-10-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rhone, Benoit; Semetey, Vincent; Synlett; vol. 28; 15; (2017); p. 2004 – 2007;,
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Related Products of 85006-25-3, The chemical industry reduces the impact on the environment during synthesis 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, I believe this compound will play a more active role in future production and life.

Example 29: 2-r i -r2,5-difluoro-4-rr(3,S,,6R)-3-methyl-l,l-dioxo-6-phenyl-thiazinan-2- Step 1: ferf-Butyl ((ferf-butoxycarbonyl)oxy)(l-(2,5-difluoro-4-(((3^,6R)-3-methyl-l,l-dioxido-6-phenyl- l,2-thiazinan-2-yl)methyl)phenyl)ethyl)carbamate To a solution of l-(2,5-difluoro-4-(((35′,6R)-3-methyl-l,l-dioxido-6-phenyl-l,2-thiazinan-2- yl)methyl)phenyl)ethyl methanesulfonate (500 mg, 1.1 mmol) in acetonitrile (30 mL) was added tert- butyl ferf-butoxycarbonyloxycarbamate (492 mg, 2.1 mmol) and Cs2C03 (1 g, 3.1 mmol). The mixture was stirred at 130 C for 3 h. The solid was removed by filtration and the filtrate was evaporated. The resulting residue was purified by Biotage Flash column (20 g silica, UV254, PE/EA= 1:0-2: 1) to afford the title compound (363 mg, 50% yield) as a white solid. LCMS (ESI): m/z = 633.0 [M+Na]+.

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 (tert-butoxycarbonyl)oxycarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; LADDYWAHETTY, Tammy; RENE, Olivier; (105 pag.)WO2016/96936; (2016); 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. 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., name: 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide

To a solution of 2-chloro-6-methylbenzoic acid (2.0 g, 11.72 mmol) in cone H2SO4 (4 mL) was added 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (1.26 g, 8.80 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was poured into ice-water and stirred for 2 h. The precipitate was collected by filtration and dried to afford 1.80 g of the title product and 6- chloro-2-methyl-3-((2,2,2-trifluoroacetamido)methyl)benzoic acid as mixture of products.

According to the analysis of related databases, 50667-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; PAWAR, Mahesh Yashwant; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/38308; (2013); A1;,
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Synthetic Route of 75175-77-8,Some common heterocyclic compound, 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, molecular formula is C11H12FNO, 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: General procedure: A mixture of appropriately substituted arylmethyl ketone (4 mmol) and DMF-DMA (20 mmol)was refluxed for8-12 h and monitored by TLC. After complete consumption ofsubstituted methyl ketone, the mixture was subjected to rotaryevaporation under reduced pressure to remove the excess of DMFDMAand the liberated methanol. After that DMSO (6-8 mL) and 4-azidobenzenesulfonamide (4 mmol) were added to reactionmixture. After addition, reaction mixture was allowed to stir at 90C for 8-10 h in silicon oil bath. After completion, reaction mixturewas poured into water to afford required product (7a-7j). Crudeproduct thus obtained was recrystalized with ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, its application will become more common.

Reference:
Article; Kumar, Rajiv; Vats, Lalit; Bua, Silvia; Supuran, Claudiu T.; Sharma, Pawan K.; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 545 – 551;,
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Electric Literature of 142-78-9, 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. 142-78-9, name is N-(2-Hydroxyethyl)dodecanamide, This compound has unique chemical properties. The synthetic route is as follows.

33 mg (4.5 mol %) of KBr (co-catalyst) was dissolved in 6 mL of water. Tetrahydrofuran solvent THF (31 mL), AA-TEMPO catalyst (25 mg, 2.5 mol %) and 1.5 g N-lauroylethanolamide (LMEA) were added with stirring to give a homogeneous water-white solution. Sodium hypochloride oxidizing agent (22 mL of 11.5% aq. Solution, 6.5 equivalents) and 2.3 mL of 2 NaOH (to maintain pH above 7) were mixed. The combined solution was added dropwise to the solution of LMEA and catalyst over a period of 1.5 hour. A separate aqueous layer immediately formed upon addition of the sodium hypochlorite solution. The pH of the aqueous layer was 12.7 after addition of the first 3.5 ml. The temperature was maintained below 32 C. with an ice-water bath. The reaction was stirred for 0.5 hr. more until complete conversion of LMEA to LG as determined by reversed-phase High Pressure Liquid Chromatography, abbreviated HPLC. The pH at end of the reaction was 7.6.At completion of the reaction, the mixture was acidified to pH 3.0 (to get the purified carboxylic acid) by addition of 8.5 mL of 1 N HCl, and the layers were separated. The lower aqueous layer was extracted with 30 mL THF, and the combined THF layers were concentrated on a rotary evaporator and dried in vacuo to give N-lauroylglycine in 116% yield (residual water present); Example 2 Oxidation of LMEA with 3.25 eq. of NaOCl, and Acid Work-UpThe procedure in Example 1 was followed, except that the amount of sodium hypochlorite was decreased to 3.25 equivalents. The isolated yield was 103% (includes residual water), showing that the oxidation works with the lower sodium hypochlorite amount; Example 4Oxidation of LMEA in THF with 6.5 eq. of NaOCl, Drowning Procedure at pH=2.6The procedure of Example 1 was followed except for the isolation step. After completion of the reaction, the mixture was acidified to pH=2.6 with 9.25 mL of 1 N HCl. The entire reaction mixture (both THF and water phases) were poured in 240 mL of water with vigorous stirring. The precipitated product was isolated by gravity filtration, and washed with 200 mL water. After air-drying, and further drying in vacuo, the product was obtained in 77% yield. The yield can be improved by better filtration techniques, e.g. by pressure filtration through a 0.45 mum or less filter; Example 5Oxidation of LMEA in THF with 3.25 eq. of NaOCl, Drowning Procedure, Effect of pH on YieldThe procedure of Example 2 was followed except for the isolation step. After completion of the reaction, the mixture was only partially acidified (to pH=5.2 with 3.6 mL of 1 N HCl.) The entire reaction mixture (both THF and water phases) were poured in 240 mL of water with vigorous stirring. The precipitated product was isolated by gravity filtration, and washed with 240 mL water. After drying in vacuo overnight, the product was obtained in 59% yield (based on free carboxylic acid), and 55% (based on the sodium carboxylate). The lower yield than Example 4 is attributed to the larger proportion of the water-soluble sodium carboxylate at the higher pH.

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

Reference:
Patent; Conopco, Inc.; US7307187; (2007); B1;,
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Electric Literature of 4943-86-6, 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. 4943-86-6, name is 2-Amino-N-(4-chlorophenyl)benzamide, This compound has unique chemical properties. The synthetic route is as follows.

The reaction flask was added 1l (2mmol, 493mg),and then added tert-butyl nitrite (6mmol, 0.72mL),followed by tetrabutylammonium iodide (5mol%,37 mg of) and acetonitrile (20mL). Then the system was heated for 12 hours at 60 deg C. for air, vacuum spin dry acetateAfter the nitrile with petroleum ether / ethyl acetate = 6/1 mixed solvent of a simple column chromatography to give the product 2L, 86% yield. yellowsolid,

The chemical industry reduces the impact on the environment during synthesis 2-Amino-N-(4-chlorophenyl)benzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhengzhou Institute of Light Industry; Yan, Yi zhe; Shi, Miao miao; Liu, Yan qi; Zhi, Huan huan; He, Yuan; Niu, Bin; (18 pag.)CN105418525; (2016); A;,
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