Tag: M.W=100-200

Electric Literature of 53250-82-1, 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. 53250-82-1, name is 4-(Methylsulfonamido)aniline belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Take a 250mL three-necked bottle, add 1.86g of p-methylsulfonylaminoaniline, 0.22g of palladium acetate and 1.00g of molecular sieve.2.04 g of methyl 2-oxopropanoate, 0.60 g of acetic acid and 100 mL of dimethyl sulfoxide were injected, followed by a 200 mL oxygen balloon, and stirred at 70 C for 18 hours.After the reaction was completed, 200 mL of ethyl acetate was added to dilute the reaction solution, and the filtered saline 100 mL was washed twice.The organic phase was separated and the aqueous phase was extracted 1time with ethyl acetate.Column chromatography yielded 2.15 g of pure methyl 5-methanesulfonylamino-1H-indole-2-carboxylate in a yield of 80%.

The synthetic route of 4-(Methylsulfonamido)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xiao Zhiyan; Ren Long; Tang Yanbo; Yang Ying; (27 pag.)CN109748840; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 38267-76-4, A common heterocyclic compound, 38267-76-4, name is tert-Butyl ethylcarbamate, molecular formula is C7H15NO2, 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.

Ethylamine hydrochloride (2.81 g, 34.5 mmol) and triethylamine (14.4 mL, 103 mmol) were dissolved in CH2Cl2 (100 mL), and cooled on ice. A solution of di-t-butyl dicarbonate (7.69 g, 35.2 mmol) in CH2Cl2 (15 mL) was added, and stirred at room temperature for 14.5 h. The mixture was diluted with CH2Cl2, washed twice with 5% aqueous HCl solution, once with saturated aqueous NaHCO3 solution,dried over anhydrous magnesium sulfate, and evaporated to give crude t-butyl ethylcarbamate (4.36 g, 87%). Crude t-butyl ethylcarbamate (3.77 g, 26.0 mmol) and allyl bromide (4.5 mL, 52.0 mmol) were dissolved in DMF (87 mL), and cooled on ice. NaH (60% in oil, 2.23 g, 55.8 mmol) was added, and stirred at room temperature for 4.5 h. After cooled on ice, the reaction was quenched by adding water. The mixture was diluted with Et2O, washed with 5% aqueous Na2S2O3 solution and saturated aqueousNaHCO3 solution, dried over anhydrous magnesium sulfate, and evaporated. Purification by column chromatography (n-hexane : EtOAc = 30 : 1 v /v), and distillation (3.0 kPa, 89 C) gave 42d (1.73 g, 36%) as colorless liquid. 1HNMR (400 MHz, CDCl3) delta 1.08 (t, J = 7.2 Hz, 3H), 1.46 (s, 9H), 3.05 (br, 2H), 3.70~3.90 (br, 2H). 13CNMR (100 MHz, CDCl3) delta 13.45, 28.43, 49.06, 79.22, 115.92, 155.37. IR (neat) 2976, 1698 cm-1.

The synthetic route of 38267-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Honzawa, Shinobu; Uchida, Mitsuaki; Tashiro, Takuya; Sugihara, Takumichi; Heterocycles; vol. 95; 2; (2017); p. 994 – 1029;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1015-89-0, These common heterocyclic compound, 1015-89-0, name is Phenanthridin-6(5H)-one, 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.

Phenanthridin-6(5H)-one (1; 0.100 g, 0.492 mmol) was placed in aSchlenk flask under argon. POCl3 (3.29 g, 2 mL, 21.4 mmol, 43 equiv)was added, and the mixture was stirred at 100 C for 24 h. The mixturewas cooled, poured onto ice, and stirred for 15 min. The solidthat formed was collected by filtration, washed thoroughly with H2O,and dried in vacuum to give a light-brown solid; yield: 95.5 mg (87%);Rf = 0.65 (hexane-EtOAc, 5:1; detection: UV).IR (KBr): 3103, 3072, 3039, 1613, 1574, 757 cm-1.1H NMR (600 MHz, acetone-d6): delta = 7.69 (ddd, J = 8.2, 7.0, 1.4 Hz, 1 H,H-12), 7.75 (ddd, J = 8.2, 7.0, 1.5 Hz, 1 H, H-13), 7.77 (ddd, J = 8.2, 7.0,1.2 Hz, 1 H, H-4), 7.91 (ddd, J = 8.3, 7.0, 1.3 Hz, 1 H, H-5), 8.10 (ddd,J = 8.2, 1.4, 0.6 Hz, 1 H, H-14), 8.48 (ddd, J = 8.2, 1.3, 0.6 Hz, 1 H, H-3),8.54 (ddt, J = 8.3, 1.5, 0.6 Hz, 1 H, H-11), 8.62 (ddt, J = 8.3, 1.2, 0.3 Hz, 1H, H-6).13C NMR (151 MHz, acetone-d6): delta = 151.45 (C-2), 143.31 (C-8),134.51 (C-10), 131.77 (C-5), 129.36 (C-13), 129.32 (C-14), 128.25 (C-4), 127.74 (C-3), 127.49 (C-12), 124.90 (C-9), 124.03 (C-7), 122.28 (C-6), 122.21 (C-11). MS (ESI): m/z (%) = 214.1 [M + H]+ (100).HRMS (ESI): m/z [M + H]+ calcd for C13H9ClN: 214.0148; found:214.0149.

Statistics shows that Phenanthridin-6(5H)-one is playing an increasingly important role. we look forward to future research findings about 1015-89-0.

Reference:
Article; Sonawane, Manoj R.; Vavra, Jan; ?aman, David; Cisa?ova, Ivana; Teply, Filip; Synthesis; vol. 47; 22; (2015); p. 3479 – 3488;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 711007-44-2, name is 2,3-Diaminobenzamide, 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 711007-44-2, Quality Control of 2,3-Diaminobenzamide

To a 100 ml three-neck flask was added 2,3-diaminobenzamide (3.2 g, 20 mmol), compound A (3.85 g, 22 mmol), sulfur powder (3.2 g, 100 mmol) was added, and stirred at 170 C. After 6 h, after cooling, 60 ml of methylene chloride was added and dissolved. The silicon gel was mixed and concentrated on a silica gel column. Chromatography on a silica gel column gave the desired product (C1) in a yield of 1.28 g (yield: 20%).

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, 2,3-Diaminobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong University Qilu Hospital; Tan Bingxu; (9 pag.)CN107556288; (2018); A;,
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 96-30-0 as follows. Quality Control of 2-Chloro-N-methylacetamide

Ethyl 1-((6-hydroxyquinolin-4-yl)thio)cyclobutanecarboxylate 5a (50 mg, 0.17 mmol), 2-chloro-N-methylacetamide (50 mg, 0.17 mmol) and potassium carbonate (35 mg, 0.25 mmol) were added to 4 mL of N,N-dimethylformamide, successively. Upon completion of the addition, the reaction solution was heated to 60 C. and stirred for 3 hours, followed by addition of 20 mL of water, and extraction with ethyl acetate (30 mL*3). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound ethyl 1-((6-(2-(methylamino)-2-oxoethoxy)quinolin-4-yl)thio)cyclobutanecarboxylate 14a (40 mg, a brown oil), yield: 65%. MS m/z (ESI): 373.3 [M-1]

According to the analysis of related databases, 96-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Lt.d; PENG, Jianbiao; SUN, Piaoyang; LAN, Jiong; GU, Chunyan; LI, Xiaotao; LIU, Bonian; HAN, Chunzhou; HU, Qiyue; JIN, Fangfang; DONG, Qing; CAO, Guoqing; (57 pag.)US2016/108035; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 19962-04-0,Some common heterocyclic compound, 19962-04-0, name is 3-Aminophenyl dimethylcarbamate, molecular formula is C9H12N2O2, 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.

C. Preparation of tert-butyl 4-(2-(dimethylamino)ethyl)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate. 1-(tert-Butoxycarbonyl)-4-(2-(dimethylamino)ethyl)piperidine-4-carboxylic acid from step B (100 mg, 0.33 mmol), HATU (175 mg, 0.46 mmol), and N,N-diisopropylethylamine (0.116 mL, 0.67 mmol) were stirred in isopropyl acetate for 10 minutes. 3-aminophenyl dimethylcarbamate (90 mg, 0.5 mmol) was added, and the reaction was stirred at 85 C. for 2 hours, cooled to room temperature, stirred overnight, and then diluted with EtOAc, washed with sat. aq. Na2CO3 and brine (with back extraction), dried over MgSO4, filtered, and concentrated under vacuum, to give the title compound as a viscous oil. MS (ES+) [M+H]+=463.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Aminophenyl dimethylcarbamate, its application will become more common.

Reference:
Patent; Burgoon, Hugh Alfred; Goodwin, Nicole Cathleen; Harrison, Bryce Alden; Healy, Jason Patrick; Liu, Ying; Mabon, Ross; Marinelli, Brett; Rawlins, David Brent; Rice, Dennis Stewart; Whitlock, Norris Andrew; US2009/264450; (2009); 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. 34801-09-7, name is N-(2-Aminophenyl)acetamide, A new synthetic method of this compound is introduced below., Formula: C8H10N2O

General procedure: A mixture of 1.00 g (5.2 mmol) of compound 1a and 0.78 g (5.2 mmol) of N-(2-amino-phenyl)acetamide in 10 mL of ethanol was refluxed for 1 h. The mixture was cooled and evaporated by half, and the yellow solid was filtered off. Yield 1.20 g (71%), mp 130-132C (decomp., from EtOH). IR spectrum, nu, cm -1 : 3272 (NH, OH), 1715 (C=O). 1 H NMR spectrum, delta, ppm: 2.11 s (3H, Me), 6.38 s (1H, 3-H), 7.07 m (1H, H arom ), 7.17 m (2H, H arom ), 7.32 m (1H, H arom ), 7.49-7.60 m (3H, H arom ), 7.96 m (2H, H arom ), 9.82 s (1H, NH), 11.61 s (1H, NH). 13 C NMR spectrum, delta C , ppm: 22.8 (Me), 95.3 (C 3 ); 122.6, 125.1, 125.9, 127.1, 128.2, 128.5, 128.9, 130.3, 131.9, 138.5 (C arom ); 151.9 (C 2 ), 165.2 (COOH), 168.8 (CONH), 189.3 (COPh). Mass spectrum: m/z 325.15 [M + H] + . Found, %: C 66.59; H 4.87; N 8.44. C 18 H 16 N 2 O 4 . Calculated, %: C 66.66; H 4.97; N 8.64. [M + H] + 325.12

The synthetic route of 34801-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stepanova; Dmitriev; Maslivets; Russian Journal of Organic Chemistry; vol. 55; 3; (2019); p. 402 – 405; Zh. Org. Khim.; vol. 55; 3; (2019); p. 469 – 473,5;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference 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.

2-Aminoethanol (Manufactured by Tokyo Chemical Industry; 19.4 g, 0.318 mol), and 400 mL of anhydrous tetrahydrofuran were put into a 1-liter four-necked flask, stirred, and cooled to an internal temperature of -10 C. Seventy milliliters of an anhydrous tetrahydrofuran solution of methacrylic acid chloride (16.6 g, 0.159 mol) was then added dropwise over the course of 30 minutes at 5 C. or lower. After the dropwise addition of the solution, the resulting mixture was stirred for 3 hours under room temperature conditions. After the reaction, insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. This produced hydroxyethyl methacrylamide as a pale yellow liquid. The hydroxyethyl methacrylamide (12.9 g, 0.10 mol) obtained by the procedure described above, 200 mL of anhydrous tetrahydrofuran, and triethylamine (15.2 g, 0.15 mol) were put into a 500-milliliter four-necked flask, stirred, and cooled to an internal temperature of -10 C. Fifty milliliters of an anhydrous tetrahydrofuran solution of methacrylic acid chloride (15.7 g, 0.15 mol) was then added dropwise over the course of 30 minutes at 5 C. or lower. After the dropwise addition of the solution, the resulting mixture was stirred for 3 hours under room temperature conditions. After the reaction, triethylamine hydrochloride was removed by filtration, and the filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (developing solvent: ethyl acetate). After the column purification, the solvent was removed under reduced pressure using a rotary evaporator, and a pale yellow liquid was obtained. The liquid was subjected to LC-MS analysis and 1H-NMR measurement. It was determined from the locations and integrals of signals that the pale yellow liquid was a target compound. The weight yield was 10.8 g, and the percentage yield was 54.8%. MS m/z: 198 (M+H)+ 1H-NMR (270 MHz CDCl3): delta 1.92 (m, 3H), 1.94 (m, 3H), 3.65 (m, 2H), 4.27 (m, 2H), 5.34 (m, 1H), 5.58 (m, 1H), 5.68 (m, 1H), 6.11 (m, 1H), 6.29 (s, 1H) (ppm)

The synthetic route of 5238-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KURARAY NORITAKE DENTAL INC.; NOJIRI, Yamato; TAKEI, Mitsuru; (33 pag.)US2018/360696; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 445-28-3,Some common heterocyclic compound, 445-28-3, name is 2-Fluorobenzamide, molecular formula is C7H6FNO, 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: Oxalyl chloride (6.61mmol) was added dropwise into a stirred solution of the appropriate benzamide (2.6mmol) in CH2Cl2 (10mL). The mixtures were heated at reflux for 20-22h. Then, solvents were evaporated in vacuo to give the respective crude benzoyl isocyanates 4a-k, which were used immediately in the next step without purification. Aminoindolin-2-one (2.8mmol) was added into a stirred solution of the appropriate benzoyl isocyanate (2.8mmol) in acetonitrile (10mL). After addition, each mixture was heated at 70-80C for 2-3h. The solid products were each filtered, washed with acetonitrile, and air dried.

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

Reference:
Article; Jagtap, Ajit Dhananjay; Chang, Pei-Teh; Liu, Jia-Rong; Wang, Hsiao-Chun; Kondekar, Nagendra B.; Shen, Li-Jiuan; Tseng, Hsiang-Wen; Chen, Grace Shiahuy; Chern, Ji-Wang; European Journal of Medicinal Chemistry; vol. 85; (2014); p. 268 – 288;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 125414-41-7, A common heterocyclic compound, 125414-41-7, name is tert-Butyl (1,3-dihydroxypropan-2-yl)carbamate, molecular formula is C8H17NO4, 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.

Preparation K Acetic acid 3-acetoxy-2-tert-butoxycarbonylamino-propyl ester (2-Hydroxy-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester (5.0 g, 26.1 mmol) was dissolved in pyridine (50 ml) and acetic anhydride (50 ml) was added. The solution was stirred at ambient temperature for 24 h when TLC showed no starting material remained. The solvent was evaporated and the residue dissolved in ethyl acetate (120 ml) and washed with dilute hydrochloric acid (3*50 ml), sodium bicarbonate solution (50 ml), brine, dried over magnesium sulphate, filtered and evaporated to give a colourless oil (7.2 g, 99% yield). The structure was confirmed by 1H NMR (300 MHz, CDCl3): 1.42 (s, 9H), 2.05 (s, 6H), 4.00-4.20 (m, 4H), 4.76-4.88 (m, 1H).

The synthetic route of 125414-41-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Morrison-Iverson, Veronique; Wynn, Duncan George; US2010/233097; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics