Category: 7341-96-0

7341-96-0,Some common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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: 2-Azanorbornene 1 (2 mmol) was dissolved in dry CHCl3 (15mL) at ambient temperature, then the substituted acetylene (2.2 mmol) was added to the solution and the homogenous mixture stirred at r.t (24 h for MP and PA; 72 h for dialkyl acetylene dicarboxylates; TLC monitoring). Evaporationof the solvent under reduced pressure gave a crude brown oil which was purified by silica gel column chromatography (hexane-EtOAc with increasingpolarity as eluent) to provide products 2-4 as colorless oils or white powders. In the case of the reaction with MP, the obtained products 2a-e were unstable at r.t in air (quickly became dark), but relatively stable under a N2 atmosphere at -16 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7341-96-0, its application will become more common.

Reference:
Article; Nasirova, Dinara K.; Malkova, Anastasia V.; Polyanskii, Kirill B.; Yankina, Kristina Yu.; Amoyaw, Prince N.-A.; Kolesnik, Irina A.; Kletskov, Alexey V.; Godovikov, Ivan A.; Nikitina, Eugeniya V.; Zubkov, Fedor I.; Tetrahedron Letters; vol. 58; 46; (2017); p. 4384 – 4387;,
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A common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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. 7341-96-0.

General procedure: CuI (0.01mmol) was added to a mixture of isatin (1) (1.0 mmol), L-proline (2) (1.0 mmol) and alkyne (3)(1.0 mmol) in acetonitrile and the reaction mixture was stirred at 80 C for2-3 h under nitrogen. The solvent was then removed under reduced pressure andthe concentrated reaction mass was purified by column chromatography on silicagel using 50% hexane-ethyl acetate to afford the desired compound.. 2-oxo-5′,6′,7′,7a’-tetrahydrospiro[indoline-3,3′-pyrrolizine]-2′-carboxamide 4a) Off white solid; Yield: 92%; mp: 260-263 C; lHNMR (400 MHz, DMSO-d6): d 10.0 (s, 1H), 7.50 (s, 1H), 7.20-7.15 (m, 1H),7.00-6.70 (m, 5H), 4.45-4.35 (m, 1H), 2.50-2.40 (m, 2H), 2.05-1.95 (m, 1H),1.80-1.45 (m, 3H); 13C NMR (100 MHz, DMSO-d6): delta 178.5,163.8, 143.2, 139.1, 137.7, 128.8, 127.3, 125.4, 120.4, 109.4, 76.9, 71.6, 47.8,30.6, 26.8; IR (KBr): 3275, 2873, 1663, 1598, 1472, 1384, 1205, 745 cm-1;m/z (ES): 270.12 (M+1, 100 %); HRMS: m/z [M + H] calcd for C15H16N3O2:270.1243; found: 270.1240.

The synthetic route of Propiolamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Shambhu Nath; Regati, Sridhar; Paul, Abir Kumar; Layek, Mohosin; Jayaprakash, Sarva; Reddy, K. Venkateshwara; Deora, Girdhar Singh; Mukherjee, Soumita; Pal, Manojit; Tetrahedron Letters; vol. 54; 40; (2013); p. 5448 – 5452;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0, 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 7341-96-0 as follows.

To a stirred solution of ethynylcarbamoyl (Method 74; 43g, 0. 62mol) in water (310ml) cooled in ice bath was added ammonium thiosulphate (92.35g, 0. 62mol) in one portion. The reaction was allowed to warm to room temperature over 5 hours. To the reaction mixture was added a solution of iodine (79.2g, 0. 31mol) in MeOH (11) rapidly over 10 minutes to yield a dark solution. Ammonium thiosuphate was added until a yellow solution was obtained. The solvent was evaporated to approximately 400ml and extracted ether (3 x 300ml). The ethereal solution was washed brine (100ml), passed through phase separation paper and evaporated in vacuo to yield the title compound as a pale orange solid (32.8g, 52%). Mpt: 70-71 C.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2003/76436; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0,Some common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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 6Synthesis of Compound (I)1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxyamide (Rufinamide); A 500 ml round-bottom flask is loaded with 2,6-difluorobenzyl azide (100 g, 0.59 mole) dissolved in methanol (300 ml), then propiolamide (49 g, 0.71 mole) obtained according to Example 5 is added under stirring to obtain a solution. Afterwards, CuSO4 pentahydrate (1.46 g, 5.9 mmoles) and ascorbic acid (5.19 g, 29.6 mmoles) are added in succession. The reaction mixture spontaneously reaches 40 C. and is kept under stirring for 4 hours at the same temperature. The formed solid is then filtered off, washed with methanol and water, and dried in an oven at 50 C., thereby affording 133 g of a solid crude in 89% yield. The solid is suspended in water (300 ml), the suspension is treated with 33% aqueous ammonia (50 ml) and left under stirring for 3 hours, then the resulting white solid is filtered and dried in an oven. 130 g of a crystalline solid are obtained in 87% yield.1H NMR (400 MHz, DMSO-d6), delta ppm: 8.56 (s, 1H), 7.87 (bs, 1H), 7.60-7.43 (m, 2H), 7.20 (m, 2H), 5.72 (s, 2H).

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

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; US2010/234616; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0, 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. 7341-96-0 name is Propiolamide, 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.

A mixture of imine (0.24 mmol), rhodium acetate (0.0024 mmol) and molecular sieves (300 mg) were mixed in a 10 mL one-Oil pump for nitrogen ventilation,A 1 mL syringe was added with 1 mL of re-evaporated CH2 Cl2 Prepared as a mixed solution A and stirred at room temperature for 10 minutes.The aryl diazonium compound (0.2 mmol) and the amide compound (0.2 mmol) were dissolved in 1 mL of re-evaporated CH2Cl2 Prepared into solution B. Solution B was added to the mixed solution A at 25 C with a syringe pump over 1 hour.Stirring 3 to 12 hours,The reaction mixture was purified by column chromatography to give pure product as shown in formula (j)Methyl (2S, 3S) -3- (2-formylmethyl) -3 – ((2-hydroxyphenyl) amino) -2-phenyl-2-propiolamide propionate,The yield was 40%Dr value equal to> 95: 5,HPLC purity was 97%.

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

Reference:
Patent; East China Normal University; Liu Shunying; Lei Ruirui; Jia Kaili; Wu Yong; Liu Donglan; Dong Suzhen; Hu Wenhao; (42 pag.)CN106831474; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0, These common heterocyclic compound, 7341-96-0, name is Propiolamide, 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.

Propiolamide (2.1 g, 31 mmol), 2,5-hexanedione (5.1 mL, 43 mmol) and para-toluenesulfonic acid monohydrate (300 mg, 1.6 mmol) were taken up in fluorobenzene (110 mL) and the reaction was heated at reflux under Dean-Stark conditions (24 h). The reaction mixture was cooled to room temperature and sodium carbonate (800 mg, 7.5 mmol) was added. The reaction mixture was stirred at room temperature (30 min) and the solids were removed by filtration. The solvent was removed and the residue was purified by column chromatography (5% ethyl acetate in hexanes). Following the elution of the title compound,the column was flushed (10% methanol in dichloromethane). The solvent was removed from the column residue and to this was added 2,5-hexanedione (3.6 mL, 31 mmol), para-toluenesulfonic acid monohydrate (300 mg, 1.6 mmol) and fluorobenzene (100 mL). The mixture was heated at reflux under Dean-Stark conditions (20 h). The reaction mixture was cooled to room temperature and sodium carbonate (800 mg, 7.5 mmol) was added. The mixture was stirred at room temperature (30 min) and the solids were removed by filtration. The solvent was removed and the residue was purified by column chromatography (5% ethyl acetate in hexanes). The two batches of the title compound were combined and further purified by column chromatography (5% ether in hexanes) to give the title compound (1.92 g, 42%) as a pale yellow solid. Rf: 0.59 (20% ether in hexanes); deltaH (300 MHz; CDCl3): 5.84 (2 H, s), 3.42 (1 H, s), 2.49 (6 H, s); deltaC (75 MHz; CDCl3): 151.1 (C), 131.5 (2C), 112.5 (2CH), 82.3 (CH), 78.0 (C), 16.5 (2Me); mp: 70-71 C (lit.[3] 68 C).

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 7341-96-0.

Reference:
Article; Law, Katherine R.; McErlean, Christopher S.P.; Tetrahedron Letters; vol. 57; 29; (2016); p. 3113 – 3116;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 7341-96-0, name is Propiolamide, 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 7341-96-0. 7341-96-0

The imine (0.2mmol), rhodium acetate (0.002mmol), Molecular sieve (300 mg) and the mixture is dissolved 1.5 ml dichloromethane solvent, into mixed solution 1, in 20 C stirring for 10 minutes. Then the propargyl amide (0.24mmol) and inter-methoxyphenyl diazo acetic acid methyl ester (0.24mmol) dissolved in 1.0 ml methylene chloride solvent, into solution 2. The solution 2 for 20 C lower, in 1 hour for adding and mixing the solution in the injection pump 1. The reaction mixture is purified by rapid column chromatography, to obtain the pure product, its structure is formula (c) is shown. The yield is 90%, dr value is equal to the 95:5. The product of the1As shown in Figure 5, H NMR schematic view thereof13C NMR schematic view as shown in Figure 6.

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 Propiolamide.

Reference:
Patent; EAST CHINA NORMAL UNIVERSITY; HU, WENHAO; WU, YONG; WANG, WENKE; TANG, MIN; (29 pag.)CN106146334; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0, The chemical industry reduces the impact on the environment during synthesis 7341-96-0, name is Propiolamide, I believe this compound will play a more active role in future production and life.

N-Chlorosuccinimide (624 mg, 4.7 mmol) was added in portions to a solution of 4- bromomethyl-benzaldehyde oxime (which may be prepared as described in Charrier, J.-D. et al. WO2011/143426 p 77; 1 g, 4.7 mmol) in DMF (9 mL) at room temperature. The reaction mixture was stirred for 2 h under argon. The mixture was poured into ice-water and this was extracted with Et2O (3 x 50 mL). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to give a solid (1.4 g). The solid was dissolved in 50% aqueous tert-butanol (20 mL) in a flask that was open to the air. Propiolamide (which may be prepared as described in Matsumoto, T. et al. US 7,851,473 Column 128; 323 mg, 4.7 mmol) was added, followed by 1 M sodium ascorbate (0.47 mL, 0.47 mmol) and 0.1 M copper(II) sulfate (2.34 mL, 0.23 mmol). KHCO3 (1.87 g, 18.7 mmol) was added in portions and the reaction mixture was stirred at room temperature for 3 h. H2O (25 mL) was added and the mixture was extracted with 85: 15 CHCl3/CH3OH (3 x 100 mL). The combined organic layers were washed with brine, dried (Na2S04), filtered, evaporated, and purified by chromatography (16-20% acetone/CH2Cl2) to give 3-(4-bromomethyl- phenyl)-isoxazole-5-carboxylic acid amide (156 mg, 12%). Purification of mixed fractions by chromatography (16-20% acetone/CH2Cl2) provided a further 40 mg (3%) of 3-(4- bromomethyl-phenyl)-isoxazole-5-carboxylic acid amide.

The chemical industry reduces the impact on the environment during synthesis Propiolamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ERICKSON, Shawn, David; GILLESPIE, Paul; MERTZ, Eric; WO2014/86704; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics