Month: July 2021

Electric Literature of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (purity 55%)(516 mg, 12.0 mmol) was added to a N,N-dimethylformamide solution (8.0 ml) of 2-chloro-1H-benzimidazole (1.52 g, 10.0 mmol), at 0C, under nitrogen stream, and stirring was carried out for 20 minutes. Methyl iodide (0.750 ml, 12.0 mmol) was further added, and stirring was carried out under room temperature for 2 hours. Water was added to the reaction solution, and the resulting solid substance was collected by filtration to afford 2-chloro-1-methyl-1H-benzimidazole (1.51 g, yield 91%) as a white solid.

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

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 540516-28-7, name is 2-(Hydroxymethyl)-5-bromobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(Hydroxymethyl)-5-bromobenzimidazole

Synthesis of 5-bromo-1H-benzimidazole-2-carboxylic acid hydrochloride 44 was prepared using 5-bromo-1H-benzimidazole-2-yl)-methanol 28 (0.23 g, 1.0 mmol) dissolved in acetone (10 mL) and potassium permanganate (0379, 2.4 mmol) dissolve in water (10 mL). The crude product was recrystallised from water. 5-Bromo-1H-benzimidazole-2-carboxylic acid in Yield 37% was recovered as a creamy white powder.

The synthetic route of 540516-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(1H-Benzo[d]imidazol-2-yl)aniline

Example 37: Preparation OF 2-BENZO L, 3] DIOXOL-5-VL-N- [3- (LH-BENZIMIDAZOL-2-YL)- PHENYLL-ACETAMIDE (Compound M To a 5.0 ml methylene chloride solution of (3,4-methylene-dioxy) phenyl acetic acid (182. 9 mg, 1.0 mmol) was added methylene chloride oxalyl chloride solution (2 M, 0.60 ml, 1.2 mmol). Five drops of DMF was added with stirring at ambient temperature. Methylene chloride and other volatile materials were removed by reduced pressure after it was stirred at ambient temperature for 3.0 h. To the residue was added DMAP (10 MG), 4-(1H-benzimidazol-2-yl)-phenylamine (83 mg, 0.40 mmol) and pyridine (2.0 ml). The mixture was stirred at 60 C for 20 hrs. Water (20 ml) was added. The solid formed was collected and was washed with aq. NAOH (3 N, 2x 10 ml), water (10 ml), aq. HCl (2 N, 3 x 10 ml), water (2 x 5 ml), ether (2 x 5 ml). An off-white compound (12 mg, 8%) was obtained. MS M/Z = 372.05 (M+H) ; IH NMR delta 10.56 (s, 1 H), 8.15 (d, J=8. 7 Hz, 2 H), 7. 87 (d, J=8. 7 Hz, 2 H), 7.72 (m, 3 H), 7.42 (m, 2 H), 6.94-6. 80 (m, 3 H), 6.00 (s, 2 H), 3.63 (s, 2H).

According to the analysis of related databases, 2963-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IMCLONE SYSTEMS INCORPORATED; WO2005/30206; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 104619-51-4, 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. 104619-51-4 name is Di(1H-imidazol-1-yl)methanimine, 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.

An oven dried round bottom flask was charged withdi(IH-imidazol-l-yl)methanimine (500 mg, 3.10 mmol),2-aminophenol (188 mg, 1.724 mmol) and anhydrous THF(20 ml) at room temperature. The resulting suspension wasrefluxed under N2 for 2 hr to give complete conversion basedon LC/MS. The solvent was removed in vacuo and the residuewas purified on a Biotage Flash Collector, eluting with30-80% EtOAc/Hexane (1200 ml) to afford the expectedproduct, benzo[d]oxazol-2-amine (200 mg, 1.5 mmol, 87%yield), as a white solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Di(1H-imidazol-1-yl)methanimine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, belongs to imidazoles-derivatives 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 5805-57-2, Safety of (1H-Benzo[d]imidazol-2-yl)methanamine

To a stirred solution of (S)-methyl 2~amino-3~(2,4~ dichiorophenylipropanoate (103 mg, 0.415 mmol) in DCM (10 mL) was added DIPEA ( 1.5 equiv) and cooled to 0 C. A solution of triphosgene (0.33 equiv) in DCM (2 mL) was added dropwise to the reaction mixture and stirred at room temperature for 2 h. The solution was 106 back to 0 C and ( lH-benzo[d]imidazol-2-yl)niethanamine (1.5 equiv) in DCM (2 nil) was added. The reaction mixture was stirred at 0 C for 30niin. The solution washed with brine, dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography to give (S)-methyi 2-(3-(( lH-benzo[dJimidazol-2- yl)methyl)ureido)-3-(2,4-dich{orophenyl)propanoate.

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, (1H-Benzo[d]imidazol-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, A common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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 potassium t-butoxide (11 mL of 1M solution, 5.5 equiv.) in THF was slowly (10 min) added to compound 3b (0.77 g, 2.0 mmol) and 1-(3-amino-5-trifluoromethylphenyl)-4-methyl-1Himidazole (0.45 g, 2.0 mmol) dissolved in THF (30 mL) at -15 to -10 C under an argon atmosphere. The dark red solution was stirred at room temperature for 3.5 h and then cooled to 0 C and treated with saturated NaCl aqueous solution (25 mL). The organic layer was separated; the aqueous one was extracted with EtOAc (2×15 mL). Combined organic extracts were dried (Na2SO4) and evaporated. The yellow solid residue was treated with toluene (5-10 mL) and filtered off to obtain nilotinib trifluoromethyl derivative 7 (0.8 g, 67%) as yellow solid; m.p. 269-271 C (EtOH); 1H NMR: delta 2.14 (3H, s, CH3), 2.32 (3H, s, CH3), 7.44 (1H, s, 5-H imidazole), 7.46 (1H, d, J = 8.1 Hz, 5-H), 7.50 (1H, dd, J = 8.0, 4.8 Hz, 5-H Py), 7.69 (1H, s, 2-H imidazole), 7.79 (1H, dd, J = 8.1, 1.7 Hz, 6-H), 7.88 (1H, s, Pm), 8.11 (1H, s, 2-H Ar), 8.16 (1H, d, J= 1.7 Hz, 2-H), 8.20 (1H, s) and 8.25 (1H, s) 4,6-H Ar, 8.48 (1H, dt, J= 8.0, 1.7 Hz, 4-H Py), 8.68 (1H, dd, J= 4.8, 1.7 Hz, 6-H Py), 9.29 (1H, d, J= 1.7 Hz, 2-H Py), 9.83 (1H, s, NH), 10.57 (1H, s, NH). 13C NMR: delta 13.5 (CH3), 18.2 (CH3), 103.2 (q, J= 3 Hz, C-5 Pm), 111.6 (q, J= 4 Hz, C-6 Ar), 114.2, 114.3 (q, J= 4 Hz, C-4 Ar), 115.0 (C-2 Ar), 120.7 (q, J= 274 Hz, CF3), 123.6 (q, J= 271 Hz, CF3), 123.8 (C-5 Py), 124.5, 124.8, 130.7, 130.8 (q, J= 32 Hz, C-CF3), 131.2, 131.9, 134.8 and 134.9 (C-4 Py, C-3), 137.3, 137.7, 137.9, 138.9, 141.3, 148.5 (C-6 Py), 152.2 (C-2 Py), 156.5 (q, J= 35 Hz, C-CF3Pm), 161.1 (C-4 Pm), 165.1 (C=O), 165.4 (C-2 Pm). Anal. calcd for C29H21N7F6O: C, 58.29; H, 3.54; N, 16.41; found: C, 58.30; H, 3.65; N, 16.22%.

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Terentjeva; Muceniece; Lusis; Journal of Chemical Research; vol. 39; 4; (2015); p. 223 – 225;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 25-1 (0.5g, 4.0mmol) in anhydrous THF (15ml) in a dried flask was added NaH (O.lg, 4.8mmol) in portions. Once bubbling had subsided iodopropane (0.8ml, 8.0mmol) was added and stirred at room temperature overnight. To the reaction mixture was added another 0.5eq of NaH was added along with 3eq of iodopropane. After stirring for 5Oh another 0.5eq of NaH was added along with 2eq of iodopropane. The reaction mixture stirred for another 2Oh before being quenched with ethanol (5ml). Solvent removal afforded the desired product 25-2 as a solid. MS calculated M+H: 169.2, found 155.1 (M-CH2).

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

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

Sodium hydride (60% in mineral oil; 0.4 g, 10 mmol) was added portionwise to a stirred solution of 4-(trifluoromethyl)-lH-imidazole (1.15 g, 8.45 mmol) in THF (19 mL) at 0 C. After stirring at 0 C for 30 minutes 2-(trimethylsilyl)ethoxymethyl chloride (1.69 g, 10 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. Water was added and the product extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated in vacuo to yield 4-(trifluoromethyl)-l-{[2-(trimethylsilyl)ethoxy]methyl}- lH-imidazole (2.2 g, 98 % yield) that was used in the next step without further purification.

The synthetic route of 33468-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 760212-58-6, 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1.0 g (2.9 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 1.5 g (3.2 mmol) of 9,10-di(2-naphtyl)anthracene-2-boronic acid, and 0.067 g (0.058 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 1.7g of a greenish white solid (84% yield) . Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 698 with respect to a molecular weight of 698.27.

The synthetic route of 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1734038; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, A common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C4H6N4O2, 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.

3a-isopropylglycoluril dimer diether (compound 2.3) (1 g, 2.5 mmol) and unsubstituted glycoluril (720 mg, 5.0 mmol) were mixed in 7M hydrochloric acid (12 mL). The mixture was stirred at room temperature for 1 hr. The mixture was heated to 100C for 2-3 hr. Evaporation of the acid in vacuo gave the a, P, 5, G-TETRAISOPROPYLCUCURBIT [4,2] uril as the major product.

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

Reference:
Patent; UNISEARCH LIMITED; WO2005/26168; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem