Month: August 2021

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. 148017-28-1, name is tert-Butyl sulfamoylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: tert-Butyl sulfamoylcarbamate

(S)-(6-chloro-2,3-dihydrobenzo[b][1 ,4]dioxin-2-yl)methanol (20.0 g, 100.0 mmol, 1 .0 eq.), tert-butoxycarbonyl sulfamide (27.4 g, 140.0 mmol, 1 .4 eq) and triphenylphosphine (3.9 g, 1 18.0 mmol, 1 .2 eq,) were dissolved in MTBE (140 g) and the resulting mixture was warmed under stirring to a temperature in the range of 27-32C. Diisopropyl-azodicarboxylate (22.6 g, 1 1 1 .0 mmol, 1 .1 1 eq) in MTBE (18 g) was added dropwise over about 60-120 min, while maintaining the temperature of the reaction mixture in the range of about 27-32C. The resulting mixture was then stirred for 2-6 hours, cooled to a temperature in the range of about 15-20C. The resulting mixture was then seeded with triphenylphosphinoxide and bis-1,2-(isopropoxycarbonyl)-hydrazine (which were taken from previously prepared batches) and stirred for an additional hour. After the onset of crystallization was confirmed, n-hexane (80 g) was added over about 45-60 min, after which time, the resulting suspension was stirred for an additional 120 min at a temperature of about 15-20C. The resulting mixture was then cooled to a temperature in the range of -15 to -10C and stirred for about 4-6 hours. The resulting off-white solid was filtered off and washed with a cold mixture of MTBE (20 g) and n-hexane (10 g). At 50C and a pressure of about 450-400 mbar a total of 240 g of solvent was distilled off from the resulting filtrate. To the resulting concentrated residue were added toluene (100 g) and n-hexane (15 g). The resulting solution, at a temperature of about 22-27C, was washed with a mixture of methanol (40 g) and water (60 g). This step was then repeated twice (2X). At a temperature of about 45C and at about 250-100 mbar pressure, about 90 g of solvent were distilled off to yield a concentrated residue containing the desired product.

The synthetic route of 148017-28-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GONG, Yong; ZINSER, Hartmut B.; WO2013/49021; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 57561-39-4, 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 57561-39-4 as follows.

To a solution (50 mL) of tert-butyl 2-hydroxyethyl(methyl)carbamate (3.50 g) obtained in Reference Example 1, thioacetic acid (1.72 mL) and triphenylphosphine (7.87 g) in tetrahydrofuran was dropwise added slowly a solution (10 mL) of diisopropyl azodicarboxylate (5.91 mL) in tetrahydrofuran under ice-cooling. The mixture was stirred under ice-cooling for 1 hr. and at room temperature for 2 hrs. The reaction mixture was again ice-cooled and a solution (10 mL) of triphenylphosphine (7.87 g) and diisopropyl azodicarboxylate (5.91 mL) in tetrahydrofuran was added. The mixture was stirred under ice-cooling for 30 min. Thioacetic acid (1.14 mL) was added and the mixture was stirred under ice-cooling for 30 min. and at room temperature overnight. The reaction mixture was concentrated under reduced pressure and hexane and diisopropyl ether were added to the residue. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. This step was repeated and a saturated aqueous sodium hydrogen carbonate solution (50 mL) was added. The mixture was extracted with ethyl acetate (100 mL). The ethyl acetate layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with ethyl acetate_hexane=5:95, and then 15:85). A 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the purified product (4.47 g) and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and ethyl acetate and diethyl ether were added to the residue for crystallization to give the title compound (1.79 g) as a pale-yellow solid.1H-NMR (DMSO-d6) : 2.38(3H,s), 2.52 (3H, s), 2.96-3.08(2H,m), 3.12-3.20(2H,m), 9.35(2H,br).

According to the analysis of related databases, 57561-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1607088; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 70-55-3, 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. 70-55-3 name is 4-Methylbenzenesulfonamide, 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: In a round-bottom flask, a benzyl alcohol 2 (1.0 mmol), a sulfonamide1 (1.8 mmol) and BF3·OEt2 (151 muL, 1.2 mmol) were dissolved in CHCl3 (2.0 mL). The mixture was stirred for 2 h under reflux in air atmosphere, then the solvent was removed under reduced pressure using a rotary evaporator. The product was isolated by column chromatography of the residue on silica gel (EtOAc-PE, 1:10 to 1:2, v/v) to give the desired mono- and di-N-benzylated products 3 and 4.

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

Reference:
Article; Pan, Jing; Li, Jia-Qiang; Huang, Ruo-Feng; Zhang, Xiao-Hui; Shen, Hang; Xiong, Yan; Zhu, Xiang-Ming; Synthesis; vol. 47; 8; (2015); p. 1101 – 1108;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 25893-50-9, A common heterocyclic compound, 25893-50-9, name is N-(2-Fluorophenyl)cinnamamide, molecular formula is C15H12FNO, 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: The appropriate cinnamanilide (5.0mmol), benzyl bromide (0.60mL, 5.0mmol) and KtBuO (0.55g, 5.0mmol) in THF (100mL) were stirred and heated under reflux for 1h. On cooling, the THF was removed by rotary evaporation and the residue partitioned between H2O (50mL) and EtOAc (100mL). The EtOAc was separated, washed with brine (50mL) and dried (MgSO4). Removal of the solvent gave the crude N-benzylcinnamanilide, which was either recrystallised from EtOAc/petrol, or purified by column chromatography on Al2O3, eluting with a solvent gradient from 1:1 DCM/petrol to DCM, then recrystallised as before. 4.2.10 N-Benzyl-N-(2-fluorophenyl)-3-phenylacrylamide (2k). Following the general procedure, N-(2-fluorophenyl)-3-phenylacrylamide19 1k (1.8g, 7.5mmol) was converted to 2k (2.0g, 80%) as a white solid; Rf (DCM) 0.3; mp 74-75C; deltaH (500MHz, CDCl3) 4.60 (1H, d, J 14.4Hz), 5.42 (1H, d, J 14.4Hz), 6.28 (1H, d, J 15.4Hz), 6.98 (1H, dt, J 1.5, 7.7Hz), 7.09 (1H, dt, J 0.7, 8.0Hz), 7.16 (1H, ddd, J 1.3, 7.7, 8.0Hz), 7.2-7.39 (11H, m), 7.78 (1H, d, J 15.4Hz); deltaC (CDCl3) 52.33 (CH2), 116.90 (CH, d, J 20Hz), 117.9 (CH), 124.7 (CH, d, J 4Hz), 127.5 (CH), 128.0 (CH), 128.4 (CH), 128.8 (CH), 129.0 (CH), 129.3 (C, d, J 13Hz), 129.8 (CH), 130.0 (CH, d, J 8Hz), 131.1 (CH), 135.1 (C), 137.1 (C), 143.2 (CH), 158.3 (C, d, J 250Hz), 166.2 (C); numax (solid) 1651, 1614, 1606, 1496, 1387, 1330, 1226, 1215, 1191, 1107, 1079, 980, 861, 818, 763, 733, 699, 679cm-1; m/z (EI) 331 (34, M+), 201 (38), 131 (100), 103 (36), 91 (20%); HMRS (EI) M+, found 331.1365. C22H18FNO requires 331.1367.

The synthetic route of 25893-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; King, Frank D.; Caddick, Stephen; Tetrahedron; vol. 69; 40; (2013); p. 8592 – 8601;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 78888-18-3, name is tert-Butyl allylcarbamate, molecular formula is C8H15NO2, 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. category: amides-buliding-blocks

Sodium hydride (768 mg of 60% dispersion in mineral oil, 19.2 mmol) was washed twice with 15 mL portions of hexane and suspended in 15 mL anhydrous THF. Reaction mixture was cooled to 0C and tert-butyl allylcarbamate (1.0 g, 6.4 mmol) was added dropwise. Reaction mixture was warmed up to room temperature and stirred under argon for 30 min. Reaction mixture was cooled to 0C and freshly distilled ethyl iodide (1.02 mL, 12.8 mmol) was added dropwise. Reaction mixture was allowed to warm up to room temperature overnight, and it was then cooled to 0C and quenched with saturated ammonium chloride solution. The layers were separated and aqueous layer was extracted with Et2O. Organics were combined and washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. Crude reaction mixture was purified by flash column chromatography (hexanes:EtOAc 4:1) to give 1.0g (85%) of the title compound as a colorless oil. IR (neat) 3083, 3010, 2979, 2933, 2249, 1682 cm-1; 1H NMR (300 MHz, CDCl3): delta [ppm] 1.03-1.07 (t, 3H, J=7.1 Hz), 1.42 (s, 9H), 3.20 (br m, 2H), 3.77 (br m, 2H), 5.05-5.11 (m, 2H), 5.68-5.81 (m, 1H); 13C NMR (75 MHz, CDCl3): delta [ppm] 12.59, 27.55, 40.39, 48.19, 78.31, 115.10, 133.67, 154.46; m/z (relative intensity) 185(1), 129(25), 112(9), 84(10), 70(30), 57(100), 41(65), 29(25). Anal.Calcd. for C10H19NO2: C, 64.83; H, 10.34; O, 17.24. Found: C, 64.67; H, 10.60; O, 17.31.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 78888-18-3, its application will become more common.

Reference:
Article; McMills, Mark C.; Humes, Ross J.; Pavlyuk, Oksana M.; Tetrahedron Letters; vol. 53; 7; (2012); p. 849 – 851;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6971-74-0, These common heterocyclic compound, 6971-74-0, name is N-Tosylbenzamide, 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-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2·H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. Anhydrous toluene (1.0 mL) solution of tert-butyl acrylate 2a (17.4 muL, 0.12 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane 1:2) to give isoindolinone 3a in 88% yield

The synthetic route of 6971-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Chen; Falck, John R.; Tetrahedron; vol. 68; 45; (2012); p. 9192 – 9199;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1565-17-9, name is 4-Acetylbenzenesulfonamide, 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. Product Details of 1565-17-9

To 4-aminosulfonylacetophenone (2.5 g) in 1,4-dioxane (30 ml) solution, N,N-dimethylformamide dimethylacetal (30 ml) was added and the mixture was stirred at 90C for 24 hours. The precipitate was collected by filtration and washed with ethyl acetate to obtain the title compound (3 g).

The synthetic route of 1565-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asubio Pharma Co., Ltd.; EP1820798; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 7150-72-3, A common heterocyclic compound, 7150-72-3, name is tert-Butyl vinylcarbamate, molecular formula is C7H13NO2, 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: A 10 mL round-bottomed flask equipped with a rubber septum and a magnetic stir bar was charged with 1 (1.0 equiv), 2 (2.5 equiv), 3 (2.0 equiv), and fac-Ir(ppy)3 (0.01 equiv). The flask was evacuated and backfilled 3 times with N2. DMSO was then added with syringe under N2. The mixture was then irradiated by white LED strips. After completion of the reaction (6 h, as judged by TLC analysis), the mixture was poured into a separatory funnel containing sat. aq NaHCO3 (20mL) and EtOAc (20 mL). After extraction with EtOAc, the organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure after filtration. The crude product was purified by flash chromatography on silica gel to afford the desired product 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; An, Xiao-De; Yu, Shouyun; Synthesis; vol. 50; 17; (2018); p. 3387 – 3394;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 308283-47-8, These common heterocyclic compound, 308283-47-8, name is 3-Bromo-N-(tert-butyl)benzenesulfonamide, 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.

[0190] A suspension of intermediate 34 (0.10 g, 0.29 mmol), 3-bromo-iV-2rt-butyl- benzenesulfonamide (84 mg, 0.29 mmol), Pd2(dba)3 (15 mg, 0.016 mmol), Xantphos (20 mg, 0.035 mmol) and cesium carbonate (0.18 g, 0.55 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 “C for 15 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue dissolved in minimum amount of EtOAc and liexanes added until solid precipitated. After filtration, the title compound was obtained as a white solid (20 mg, 12percent) .[0191] 1H NMR (500 MHz, DMSO-d6): delta 1.12 (s, 9H), 1.30-1.40 (m, 2H), 1.50-1.56 (m, 4H), 2.16 (s, 3H), 2.88 (t, J= 5.3 Hz, 4H), 7.17 (d, J= 7.8 Hz, IH), 7.43 (t, J= 8.0 Hz, IH), 7.59-7.60 (m, 2H), 7.58 (s, IH), 8.13 (s, IH), 7.16 (dd, J= 7.9, 1.9 Hz, IH), 8.18-8.22 (m, IH), 8.67 (s, IH), 9.37 (s, IH). MS (ES+): m/z 559 (M+H)+.

Statistics shows that 3-Bromo-N-(tert-butyl)benzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 308283-47-8.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 114790-39-5, name is Benzyl (2,2-dimethoxyethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 114790-39-5

A solution of benzyl N-(2,2-dimethoxyethyl)carbamate (50 g, 208.9 mmol) in toluene (180 mL) is treated with solid potassium hydroxide (51.6 g, 919.69 mmol) under nitrogen. After 10 minutes, benzyltriethylammonium chloride (0.8 g, 3.1 mmol) is added. After another 10 minutes a solution of allyl bromide (33 g, 272.8 mmol) in toluene (50 mL) is added drop wise over 10 minutes. The resultant mixture is stirred at 50 C for 48 hours. The mixture is cooled to room temperature and quenched with water. The organic layer is separated, washed with brine, dried over magnesium sulfate, and concentrated to dryness to give the title compound (44 g, 75%). ES/MS (m/e): 280 (M+H).

The synthetic route of 114790-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; COATES, David Andrew; LOSADA, Pablo Garcia; (46 pag.)WO2016/43996; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics