Month: May 2021

Synthetic Route of 6775-40-2,Some common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, molecular formula is C9H9N3, 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: Amide formationTo a solution of carboxylic acid (1.0 mmol) in dry DMF (2.5 niL) was added HBTU(1.2 mmol) in one portion, the reaction mixture was stirred at room temperature for 10 min, and then an amine (1.0 mmol) and DIEA (0.8 mL) were added subsequently. The resulting reaction mixture was stirred at room temperature for 12 h or in some cases at 70 0C for 1-3 h.The reaction mixture was diluted with water (50 mL) and the product was precipitated. The product was either isolated after filtration, subsequent washings with water and ethyl acetate or silica gel column chromatography.; 120 mg (0.4 mmol) of 2-isoquinolin-3-yl-lH-benzoimidazole-4-carboxylic acid was reacted with 400 mg (1.1 mmol) of HBTU and 160 mg (1.0 mmol) of 4-phenyl-lH-imidazol- 2-ylamine (160 mg, 1 mmol) according to the general procedure A. The residue was purified by flash column chromatography (EtOAc) to provide 2-isoquinolin-3-yl-lH-benzoimidazole- 4-carboxylic acid (4-phenyl-lH-imidazol-2-yl)-amide (30 mg, 17.5%). LCMS: 431 (M + I)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Phenyl-1H-imidazol-2-amine, its application will become more common.

Electric Literature of 4857-06-1, The chemical industry reduces the impact on the environment during synthesis 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

General procedure: To a stirred solution of 1c (1.0 eq.) and POCl3 (10 eq.) was addeda few drops of conc. HCl. The reaction mixture was heated to 150 C and stirred for 3 h. After the reaction was completed, the reaction mixture was poured into ice water, neutralized with 1 N aq. NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo to givecrude product 1d. Alternatively, to a stirred mixture of 2-chlorobenzimidazole (1.0 eq.) and R3CH2Br (1.0 eq.) in dimethylformamide was added N,N-diisopropylethylamine (1.5 eq.). The reaction mixture was heated to 110 C and stirred for 12 h. After the reaction was completed, the reaction mixture was cooled down to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (ethyl acetate/hexane) to give desired product 1d.

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-Chloro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference of 41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

1) N-Methoxy-N-methyl-1-methyl-1H-imidazole-4-carboxamide 1-Methyl-1H-imidazole-4-carboxylic acid (1.26 g), N,O-dimethylhydroxylamine hydrochloride (1.17 g), 1-hydroxybenzotriazole (1.84 g), triethylamine (2.09 mL), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g) were dissolved in N,N-dimethylformamide (50 mL), and the solution was stirred overnight at room temperature. The reaction solvent was evaporated under reduced pressure, and ethanol was added to the residue. Insoluble matter was removed through filtration, and the solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform – methanol – water, lower phase), to thereby give N-methoxy-N-methyl-1-methyl-1H-imidazole-4-carboxamide as a solid product (1.08 g, 64percent). 1H-NMR(400MHz,CDCl3)delta:3.45(3H,s), 3.73(3H,s), 3.78(3H,s), 7.45(1H,s),7.54(1H,s).

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 705-09-9, 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. 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To a solution of Id (599mg, 3.57mmol) in DMF (20mL) was added NaH (143mg, 3.57mmol) with ice-bath. The resulting mixture was stirred for 15min. at 0-5 C and was added lc (1.43g, 3.57mmol). The reaction mixture was stirred at r.t. over night and evaporated to remove DMF. The residue was purified by column chromatography (PE:EA=1 :2) to give le (1.13g, 59.5% yield).

The chemical industry reduces the impact on the environment during synthesis 2-(Difluoromethyl)-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Synthetic Route of 89830-98-8, 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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0°C under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0°C. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H). BuLi (1.6M in hexane)(1 1 mL; 17.6 mmol) was added to a solution of J-1 b (3.5 g; 14.7 mmol) in THF (60 mL) at -50°C. The mixture was stirred at the sametemperature for 30 min and DMF (1 .7 mL; 22 mmol) was added. The mixture was warmed slowly to RT in 1 h and NH2OH,HCI (970 mg; 29.4 mmol) was added and the mixture was stirred at RT for 16h. Water was added and the product was extracted with DCM (3 times), washed with brine, dried over MgS04 and the solvent was removed under reduced pressure to give 4.1 g (quantitative yield) of the mixture of isomers K-1 as yellow oil.HPLC Rt (min) = 5.30, 5.41 and 5.90 ; MS M+ (H+): 282 (method V2002V2002)

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, 5-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

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 705-09-9 as follows. Application In Synthesis of 2-(Difluoromethyl)-1H-benzo[d]imidazole

A mixture of 2-difluoromethyl-lH-benzimidazole (2.22 g), 2,4-dichloro- 6-morpholinopyrimidine (2.81 g), potassium carbonate (6.63 g) and DMF (50 ml) was stirred under nitrogen and heated to 90C for 16 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1:1 mixture of isohexane and diethyl ether. There was thus obtained 4-chloro-2-(2-difluoromethylbenzimidazol- 1 -yl)-6-morpholinopyrimidine (3.17 g); NMR Spectrum: (DMSOd6) 3.75 (s, 8H), 7.09 (s, IH), 7.45-7.47 (m, IH), 7.50-7.54 (m, IH), 7.57-7.83 (t, IH), 7.87 (d, IH), 8.31 (d, IH); Mass Spectrum: M+H+ 366.

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference of 7189-69-7, A common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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.

A solution of Iota ,Iota ‘-sulfonyldiimidazole (1 ; 2.88 g, 14.5 mmol, reference 56) and 3,5- dichlorophenol (2; 1.18 g, 7.25 mmol) in THF (28.8 mL) was treated with cesium carbonate (1.18 g, 3.63 mmol), heated at a reflux and stirred for 18 h. The volatiles were evaporated. The residue was dissolved in EtOAc (20 mL), washed sequentially with water (25 mL), sat. amonium chloride solution (25 mL) and brine (25 mL), dried over MgS04, filtered and evaporated. The residue was purified by flash chromatography eluting with 1 :9 EtOAc:hexane. Evaporation of the collected fractions afforded sulfonate 3 (1.6 g, 75 %) as an oil: Rf 0.46 (3:17 EtOAc:hexane); 1H NMR (CDCI3, 400 MHz) delta 6.89 (2H, d, J = 1.8), 7.20 (1 H, dd, J = 0.6, 1.5), 7.30 (1 H, t, J = 1.5), 7.37 (1 H, t, J = 1.8), 7.82 (1 H, s); 13C NMR (CDCI3, 75 MHz) delta 118.6, 120.9, 129.6, 132.1 , 136.6, 137.7, 149.3; IR (neat) vmax/cm”1 1 152, 1189, 1209, 1421 , 1577, 3088; HRMS (ESI) m/z calculated for CgHrCfeNzOaS [M+H]+ 292.9549; found 292.9551.

The synthetic route of 7189-69-7 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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 1.1.3 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole (Compound 3) A mixture of Compound 2 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533 g, 2.1 mmol), bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Cl2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (KOAc) (0.393 g, 4 mmol) in 1,4-dioxane (20 ml) was heated at about 80 C. under argon overnight. After cooling to RT, the whole was diluted with ethyl acetate (80 mL) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid 3 (0.64 g, in 81% yield).

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

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 17325-26-7 as follows. name: Methyl 1H-imidazole-5-carboxylate

Methyl 1H-imidazole-4-carboxylate (96.5 g, 765.1 mmol) was dissolved in 1.8 LIn N,N-dimethylformamide (DMF), then triphenylchloromethane (213.3 g, 765.1 mmol) was added.Finally, triethylamine (85.2 g, 841.6 mmol) was added.After the addition, the nitrogen was replaced three times, and the reaction was carried out at room temperature for about 2 hours.The TLC detects the completion of the reaction and terminates the reaction. Post processing:The reaction system was slowly poured into 6 L of water, stirred and lysed for 1.0 h, filtered, and the filter cake was washed with 500 ml of water.Drying at 50 C for 4 h gave 282.0 g of an off-white solid in a yield of 100.0%.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

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 71759-89-2 as follows. HPLC of Formula: C3H3IN2

Preparation 72 4-Iodo-1-triphenylmethyl-1H-imidazole To 4-iodo-1H-imidazole (Preparation 71, 3.0 g, 15.3 mmol) in N,N-dimethylformamide (25 ml) was added triphenylmethyl chloride (4.72 g, 16.9 mmol) and then triethylamine (2.5 ml, 18.4 mmol). After stirring at room temperature for 2.5 h, water (200 ml) was added and the reaction mixture was filtered and washed with water. The crude solid was chromatographed on silica gel eluding with hexane:ethyl acetate (5:1 and then 2:1). The material was then recrystallized from hexane and dichloromethane to give the title compound as a white solid (4.0 g, 59%). NMR (CDCl3, selected data for the free base: 6.9 (m, 1H), 7.0-7.2 (m, 6H), 7.25-7.4 (m, 10H). MS (TSP): M/Z (MH+): 436.3; C22H17129IN2+H requires 437.1.

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.