Month: March 2021

68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C10H8N2O

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (0.35 g) in dimethylformamide (5 mL) were added potassium carbonate (843 mg) and 1-(bromomethyl)-4-fluorobenzene (462 mg) and the mixture was stirred at 75C for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in a mixture of 40% methylamine-methanol solution (474 mg) and methanol (5 mL), and the mixture was stirred for 5 min. Sodium borohydride (154 mg) was added and the mixture was stirred for 1 hr. Saturated sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0?4:1) and dissolved in methanol. A 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from a mixed solution of methanol-tetrahydrofuran (1:4) to give the title compound as colorless crystals (yield 450 mg, yield 60%). melting point: 169-171C. 1H-NMR(DMSO-d6)delta:2.59(3H,t,J=5.1Hz), 4.25(2H,t,J=4.9Hz), 5.49(2H,s), 7.13-7.30(4H,m), 7.53-7.68(3H,m), 7.70-7.76(2H,m), 7.83(1H,s), 9.72(2H,brs), 1H not detected.

The synthetic route of 68282-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2196459; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

2-Chloro-5,6-dibromobenzimidazole (17) To a suspension of 0.763 g (5 mmole) of 2-chlorobenzimidazole in 50 mL of 1:1 MeOH/H2 O, was added dropwise a solution of 1 mL of Br2 in 10 mL of MeOH over a period of 30 min. The reaction mixture was stirred at room temperature overnight and was then filtered. The solid was washed with portions of H2 O until the washings were neutral. This solid was air dried and recrystallized from MeOH to give 1.115 g (3 crops, 72%) of 17. mp 228 C.; 1 H NMR (DMSO-d6) d 13-14 (br. s, 1, 1-NH), 7.93 (s, 2, 4-H, 7-H).

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:
Patent; The Regents of the University of Michigan; US5574058; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6001835; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 71759-89-2, These common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, 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: Method B: In a20 mL microwave Biotage tube, a 1M Na2CO3 aqueous solution(5 mL) purged with argon were introduced into a mixture purged with argon of 4-iodo-1H-imidazole (1a) (0.194 g, 1.0 mmol), a boronicacid 2 (1.6 mmol) and Pd(PPh3)4 (0.80 g, 0.05 mmol) in DMF (15 mL). The mixture washeated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3j and 3p-3u in yields ranging from 30 to 95%. Time and temperaturereactions were collected in Table 1.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 4856-97-7 as follows. Quality Control of (1H-Benzoimidazol-2-yl)methanol

The procedure for gram scale oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehydewas as follows: (1H-benzo[d]imidazol-2-yl)methanol (0.1 mol,14.8 g) and [Ru(bpbp)(pydic)] (0.001 mmol, 7.32 ¡Á 10-3 g) wereadded into a reactor. The reactor containing this mixture was heatedto 50 C in an oil bath under vigorous stirring and then 30% H2O2(30 mL, 0.3 mol) was slowly dropwise over a period of 30 min. The mixture was stirred for 5 h. After filtering, the solution wasevaporation under reduced pressure at 50 C. Pure 1H-benzo[d]imidazole-2-carbaldehyde (0.07 mmol, 10.2 g) was obtained with ayield of 70% after recrystallisation from 30% H2SO4 solution. Theproduct, 1H-benzo[d]imidazole-2-carbaldehyde, was identified byits 1H NMR spectrum.

According to the analysis of related databases, 4856-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Shenggui; Pan, Rongkai; Su, Wenyi; Li, Guobi; Ni, Chunlin; Journal of Chemical Research; vol. 41; 2; (2017); p. 88 – 92;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 496-46-8,Some common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C4H6N4O2, 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 6; PREPARATION OF A CUCURBITURIL TRIMER; A CB trimer, according to the present invention, can be prepared according to two converging pathways, as is detailed hereinabove (Example 5) and is further presented in Figure 6. In general, one route of synthesizing a CB trimer involves formation of a derivatized CB monomer prior to the trimerization step, and another route involves formation of an assembling unit on which three CB moieties are formed in a consecutive step. As an exemplary starting material for both routes, a glycoluril derivatized by a fused pyrrolidine ring (Figure 6, Compound 19) is prepared, either by reacting diethyl iminodiacetate (Figure 6, Compound 15) with 4-morpholin-4-yl-furan-3-one (Figure 6, Compound 16), or by reacting dimethylester-glycoluril (Figure 6, Compound 17) and 2,5-dione-pyrollidono-glycoluril (Figure 6, Compound 18). Compound 19 is reacted with glycoluril, Compound 2, in a 1: 5 ratio with formaldehyde, in the presence of concentrated sulfuric acid, to thereby form the derivatized cucurbituril pyrrolidino-CB [6] (Figure 6, Compound 20). Compound 20 is thereafter converted to the cyanoamine and the latter is reacted so as to form a CB trimer (as presented in Figure 6, Compound 22) having a triazine ring as the assembling unit. Alternatively, Compound 19 is first converted to the cyanoimine, which is thereafter reacted so as to form the triazine ring at the center of trimerization. The resulting 1, 3,5-tri (2,5-dione-pyrollidono-glycoluril)-triazine (Figure 6, Compound 21) is reacted with glycoluril, Compound 2, in a 1: 15 ratio and with formaldehyde, in the presence of concentrated sulfuric acid, to thereby form a cucurbituril trimer (Figure 6, Compound 22) having a triazine ring as the assembling unit.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TECHNION RESEARCH & DEVELOPMENT FOUNDATION LTD.; WO2005/23816; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 2302-25-2 as follows. name: 4-Bromo-1H-imidazole

General Procedure 46 To a mixture of 4-bromo-imidazole (995 mg, 6.77 mmol), potassium hydroxide (380 mg, 6.77 mmol), potassium carbonate (936 mg, 6.77 mmol) and tetra-n-butyl ammonium bromide (109 mg, 0.339 mmol) in dichloromethane (7 mL) was added tert-butyl bromo acetate (0.50 mL, 3.4 mmol). After stirring overnight the reaction was filtered. The filtrate was dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, ethyl acetate to afford (4-Bromo-imidazol-1-yl)-acetic acid tert-butyl ester (696 mg, 79%).

According to the analysis of related databases, 2302-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 36947-68-9, 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A vessel with a magnetic stirrer bar was charged with imidazole derivative (0.5 mmol), CuI (10 mg, 0.05 mmol), Cs2CO3 (0.33 g, 1 mmol), PPh3 (26 mg, 0.1 mmol) and tetrabutylammonium bromide (TBAB) (0.2 g, 0.6 mmol) under a nitrogen atmosphere. The reaction vessel was evacuated and backfilled with nitrogen three times. In a separate flask, a solution of dry dioxane (2 mL) containing the 1,1-dihalo-1-alkenes (1 mmol) was evacuated and back-filled with nitrogen gas three times. The dioxane solution was then added to the reaction flask via a syringe and the reaction mixture heated to 100 C for 30 hours. The reaction mixture was cooled to room temperature, quenched with 5 mL of a saturated NH4Cl solution, and extracted with ethyl acetate (3 x 10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as the eluent to afford the corresponding products:

The chemical industry reduces the impact on the environment during synthesis 2-Isopropyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Man-Gang; Yu, Hua; Wu, Jun; Shang, Zhi-Cai; Journal of Chemical Research; vol. 37; 9; (2013); p. 570 – 573;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 1-Methyl-1H-imidazole-4-carboxylic acid 4-(3-hydroxy-4-isobutyryl-2-trifluoromethyl-phenoxymethyl)-benzylamide Mechanically stir suspensions of 1-[4-(4-aminomethyl-benzyloxy)-2-hydroxy-3-trifluoromethyl-phenyl]-2-methyl-propan-1-one hydrochloride (244 g, 604 mmol), 1-methyl-imidazole-4-carboxylic acid (95 g, 753 mmol), and 1-hydroxybenzotriazole hydrate (118 g, 770 mmol) in tetrahydrofuran (8 L) in two separate 22-L Morton flasks. Treat each solution with diisopropylethylamine (269 mL, 1.54 mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (145 g, 756 mmol) in single portions and stir overnight at room temperature. Dilute each with 4 L of water and extract twice with 4 L of ethyl acetate. Wash organic layers with saturated sodium chloride solution, dry with magnesium sulfate, filter, and evaporate the filtrates to tan foams. Combine the foams and recrystallize from isopropanol (6 L) to afford the title compound (426 g, 74percent yield). m.p. 164.7¡ã C.; HPLC Rt=4.86 min; 1H NMR (DMSO-d6) delta 13.95 (s, 1H), 8.45 (t, J=8.0 Hz, 1H), 8.27 (d, J=8.0 Hz, 1H), 7.63 (d, J=12.0 Hz, 2H), 7.33 (ABq, J=12.0, 8.0 Hz, 4H), 6.89 (d, J=8.0 Hz, 1H), 5.32 (s, 2H), 4.39 (d, J=8.0 Hz, 2H), 3.71 (hept, J=8.0 Hz, 1H), 3.67 (s, 3H), 1.12 (d, J=8.0 Hz, 6H); 19F NMR (DMSO-d6) delta-54.10; MS (m/z): 476.0 (M+1).

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, 1-Methyl-1H-imidazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 124312-73-8, These common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, 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: To a solution of 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine (1 equiv) and diisopropylethylamine (1.5 equiv) in 2-propanol was added amine (1.2 equiv). After refluxing for 16 h, the reaction mixture was concentrated in vacuo and the appropriate solvent added to precipitate the crude product, which was collected by filtration and then purified by recrystallization, prep HPLC or column chromatography.

The synthetic route of 124312-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Candice, Soares De Melo; Feng, Tzu-Shean; Van Der Westhuyzen, Renier; Gessner, Richard K.; Street, Leslie J.; Morgans, Garreth L.; Warner, Digby F.; Moosa, Atica; Naran, Krupa; Lawrence, Nina; Boshoff, Helena I.M.; Barry, Clifton E.; Harris, C. John; Gordon, Richard; Chibale, Kelly; Bioorganic and Medicinal Chemistry; vol. 23; 22; (2015); p. 7240 – 7250;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem