Month: May 2021

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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. Recommanded Product: 6-Aminobenzimidazole

To a solution (6 ML) of 1-[5-amino-2-(benzhydryloxy)phenyl]-2-methylpropan-1-one (190 mg, 0.550 mmol) in acetonitrile were added diisopropylethyl amine (0.110 ML, 0.660 mmol) and N,N’-disuccinimidyl carbonate (169 mg, 0.660 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour.. To the reaction solution were added diisopropylethyl amine (0.110 ML, 0.660 mmol) and 1H-benzoimidazol-5-amine (87.8 mg, 0.6605 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 12 hours.. The reaction solution was poured into water and was extracted with ethyl acetate.. The extracted solution was washed with water, and was dried with anhydrous magnesium sulfate.. The solvent was distilled off under reduced pressure, and the residue was purified by silicagel column chromatography (ethyl acetate:methanol = 10:1).. The fractions containing the titled compound were collected, which was washed with water, was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain the titled compound as a solid. 102 mg (36.7%) 1H-NMR (CDCl3) delta; 0.96 (6H, d, J = 7.0 Hz), 3.39 to 3.46 (1H, m), 6.07 (1H, s), 6.63 to 6.77 (2H, m), 7.18 to 7.46 (15H, m), 8.16 (2H, bs)

The synthetic route of 6-Aminobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1437344; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 288-32-4, 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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Under ice-cooling, sodium hydride (60%, 1.40 g, 35 mmol) was added in one portion to dry tetrahydrofuran (25 mL), and the resulting reaction solution was warmed to room temperature and stirred for 30 minutes.Under ice-cooling, 1H-imidazole (2.00 g, 30 mmol, 6 mL of dry THF solution) was added dropwise, and the resulting reaction solution was warmed to room temperature and stirred for 1.5 h.1-Bromo-3-chloropropane (4.60 g, 30 mmol) was added dropwise and the reaction was allowed to react at room temperature overnight.Methanol (5 mL) was added to the reaction system in one portion, filtered, the solvent was distilled off under reduced pressure, and the crude product was purified by column chromatography (dichloromethane/methanol (V/V) = 30/1).A pale yellow oil (3.10 g, 73%) was obtained.

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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. Formula: C7H7N3

The compound was synthesized as hydrochloride salt by the following procedure.Phenyl chloroformate (0.98 mL, 7.8 mmol) was dissolved in CH2Cl2, cooled down to 0 C. and 5-aminobenzimidazole (0.865 g, 6.5 mmol) was added slowly. The mixture was kept at 0 C. for 30 min and then the mixture was allowed to adapt ambient temperature. The mixture was stirred at ambient temperature for 2 h. The resulting solid was withdrawn by suction, dried and taken up in a small amount of DMF. To the solution, 1-amino-3,3-dimethylbutan-2-one (0.986, 6.5 mmol) and TEA (2.73 mL, 19.5 mmol) were added. The mixture was kept at 40 C. for 2 h. The solvent was removed and purified by means of preparative HPLC. The remains were re-dissolved in MeOH and a small amount of HCl was added (1-2%). The solution was subjected to hydrogenation (PdC, 10% on charcoal, 4 bar, 60 C.) for 4 h. The catalyst was removed by filtration through a pad of CELITE and the residue was washed with water. The organic layer was dried, filtrated and the solvent was removed to result in the final product. Yield: 0.087 g (6.3%); MS m/z 259.4 (M+H)+; 1H NMR (DMSO, 400 MHz): delta 0.72 (s, 9H); 3.23-3.27 (m, H); 3.46-3.50 (m, H); 4.37-4.41 (m, H); 6.84 (bs, H); 7.56 (dd, H, 3J=9.1 Hz, 4J=1.7 Hz); 7.70 (d, H, J=9.1 Hz); 7.81 (d, H, 4J=1.7 Hz); 9.27 (s, H), HPLC (lambda=214 nm, [B]: rt 6.83 min (99%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 934-22-5, its application will become more common.

Reference:
Patent; PROBIODRUG AG; US2011/92501; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3012-80-4, These common heterocyclic compound, 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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: Equimolar quantities of 1-methyl-1H-benzo[d]imidazole-2-carbaldehyde and the respective aniline derivative were placed in microwave vial, and the reaction mixture was irradiated at 90?C during 4?min. After cooling to room temperature, the resulting residue was then purified by recrystallization in ethanol to give the pure Schiff base. N-(4-methoxyphenyl)-1-(1-methyl-1H-benzo[d]imidazol-2-yl)methanimine (L1).

The synthetic route of 3012-80-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boulebd, Houssem; Lahneche, Yousra Doria; Khodja, Imene Amine; Benslimane, Meriem; Belfaitah, Ali; Journal of Molecular Structure; vol. 1196; (2019); p. 58 – 65;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53710-78-4, 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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 60% NaH (9.6mg, 0.24mmol) was added to a solution of 5a (100mg, 0.24mmol) in dry DMF (10mL) at room temperature. After stirring for 30min, 1-(3-chloropropyl)-1H-imidazole (52mg, 0.36mmol) was added and the mixture was then stirred for 5h at 80C. After cooling, the mixture was poured into cold water (200mL) and extracted with EtOAc (3×50mL). The combined organic phase was washed with brine (3×150mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using dichloromethane/ 20 methanol/triethylamine (120:4:1, v/v/v) as eluent to afford 64.4mg (51.0%) 6a as a red solid.

The chemical industry reduces the impact on the environment during synthesis 1-(3-Chloropropyl)-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Xiaoqi; Hu, Yuanyuan; Gao, Anhui; Xu, Meng; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Li, Jia; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 589 – 603;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 760212-58-6, 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 760212-58-6 as follows.

Under nitrogen protection,In a 1000ml three-neck bottle,30 g (85.96 mmol, 1 eq) of the compound 1- (4-bromophenyl) -2-phenyl-1H-benzo [d] imidazole was added to 300 mL of tetrahydrofuran,Cooling down to minus 78 degrees,39.4 mL (94.56 mmol, 1.1 eq) of n-BuLi was slowly added dropwise to the above reaction solution,Incubation reaction for 1.5h,Subsequently, 32.3 g (171.92 mmol, 2 eq) of triisopropyl borate was slowly added dropwise to the above reaction solution,Naturally warmed to room temperature and stirred overnight to stop the reaction,Add 100 mL of a 1 mol / L dilute hydrochloric acid solution and stir at room temperature for 1 h.The layers were separated, and the aqueous phase was extracted with 200 mL of dichloromethane * 1. The organic phases were combined.Spin-drying gave 21.67 g of a white solid with a yield of 80%.

According to the analysis of related databases, 760212-58-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Tsinghua University; Duan Lian; Gao Wenzheng; Shao Shuang; (32 pag.)CN110818687; (2020); A;,
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. 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C13H10N2O

a.) 15.72 g (74.8 mmol) of 3-phenyl-1 H-benzimidazol-2-one, 6.94 g (34.0 mmol) of 1 ,3-difluoro- 4,6-dinitrobenzene and 28.87 g (136 mmol) of K3P04 were mixed together in N M P (200 mL) at 0C for 2h. The mixture was then stirred 2h at room temperature and precipitated in water fil- trated to yield 19.44 g of 2-1 as a yellow powder [Purity = 85%(H PLC)] which was used directly as it is for the next step. (0778) Mass [M+1 ] = 584.2

According to the analysis of related databases, 14813-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; FLORES, Jean-Charles; NAGASHIMA, Hideaki; (236 pag.)WO2017/93958; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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. Safety of 1H,1’H-2,2′-Biimidazole

Synthetic example 2:4,441H ‘H-2>2,-biimidazole-1 vdiyl)bis(/Vl/V-diphenylaniline)A mixture of IH.I’H^’-biimidazole (1.02 g, 7.63 mmol), 4-bromo-A/,A/- diphenylaniline (9.89 g, 30.5 mmol) and Cs2C03 (12.4 g, 38.2 mmol) in DMF (150 mL) was degassed (N2 bubbling, 15 min). Cu20 (440 mg, 3.0 mmol) was added and the mixture was heated (140 C, 72h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H20 and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc/Et-jN/MeOH 100:1 :0 then 100:1 :2 then 100:1:5) to give 4,4′- (1Hl1,H-2,2,-biimidazole-1,r-diyl)bis(A/,A/-diphenylaniline) (1.57 g, 33%) as a colourless solid. A. portion of this material was further purified firstly, by recrystallisation (petrol/toluene) and then by distillation (sublimation apparatus 215 C, 10-6 mBar): m.p. 174 – 182 C (DSC); 1H NMR (CDCI3, 400 MHz) delta 6.67 (d, J 8.8 Hz, 4H), 6.88 (d, J 8.8 Hz, 4H), 7.00 – 7.06 (m, 12H), 7.15 (br s, 2H), 7.18 – 7.25 (m, 8H), 7.34 (br s, 2H); 13C NMR (CDCI3, 100 MHz) delta 121.8, 122.7, 123.8, 124.6, 124.7, 128.9, 129.4, 130.0, 146.9, 147.8; HRMS (El) m/z 619.2598 C 2H3iN6 [M – H]+* requires 619.2605

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; MACDONALD, James Matthew; BOWN, Mark; UENO, Kazunori; WEBER, Karl Peter; O’CONNELL, Jenny Lee; HIRAI, Tadahiko; WO2012/51666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 615-16-7, 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. 615-16-7, name is 2-Hydroxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under N2 protection, 2(3H)-benzimidazolone 2 (20 g, 149 mmol) was dissolved in CH2Cl2 (75 mL). The solution was cooled to 5 oC and AlCl3 (48 g, 358 mmol) was carefully added as a solid in three equal portions over 10 min. Then ,2-chloropropionyl chloride 3 (21 g, 169 mmol) was added dropwise. After the addition, the reaction mixture was warmed up and stirred for 17 h at room temperature. Then, AlCl3 (10 g, 75 mmol) was added and the reaction mixture was stirred for 2 h at 25 oC. The reaction mixture was slowly poured into acooled mixture (pre-cooled to 5 oC) of heptane (300 mL) and H2O (300 mL). The result mixture was stirred for 15 h at 25 oC. Filtration of the mixture gave a wet cake, which was washed by H2O (200 mL), followed by heptane (100 mL). The resulting cake was dried over 50 oC for 3 h to give compound 4 (33 g,98%); a brown solid; mp 142-144 oC; IR (KBr, max cm-1): 3197, 3095, 2987, 2857, 1750, 1674, 1473,1276, 1201, 872, 708 cm-1; 1H-NMR (400 MHz, DMSO-d6): = 1.60 (d, J = 4.8 Hz, 3H), 5.75 (q, J = 4.8Hz, 1H), 7.06 (d, J = 6.3 Hz, 1H), 7.55 (s, 1H), 7.66 (d, J = 6.3 Hz, 1H), 10.98 (br s, 1H), 11.16 (br s, 1H)ppm; 13C-NMR (100 MHz, DMSO-d6): = 20.62, 53.66, 108.63, 109.14, 123.86, 127.02, 130.37, 135.23,155.90, 193.11 ppm; HRMS (ESI): calcd. for C10H10ClN2O2 225.0431 [M+H]+; found 225.0431. Anal.Calcd for C10H9ClN2O2: C, 53.47; H, 4.04; Cl, 15.78; N, 12.47. Found: C, 53.40; H, 3.95; Cl, 15.71; N,12.38.

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-Hydroxybenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zou, Ping; Hu, Lin; Yan, Xi-Meng; Li, Xiao-Yue; Wei, Wanguo; Qiu, Xiao-Long; Gou, Shao-Hua; Heterocycles; vol. 98; 5; (2019); p. 674 – 680;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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) Preparation of nitric-sulfuric mixed acid: at 10 C, sequentially, in a beaker 54mL of fuming sulfuric acid and slowly dropping 12.8mL of fuming nitric acid and during adding process of fuming nitric acid attention to keep stirring; (2) At room temperature, 22 mL of fuming sulfuric acid and 13.6 g (0.2 mol) of imidazole were added slowly to a three-necked flask, the reaction continuously stirred for 30 min, and the mixture was thoroughly mixed. The temperatures was then set to 65 C and after reaching to a corresponding temperature add the whole nitric-sulfuric mixed acid prepared above, and reaction was carried out for 1h. After the end of the reaction, slowly poured into 550g ice water, stirring it until it is melt, and then heated to 120 C and reacted for 1h. then cooling, suction and drying was carried out to obtain 4-NI;

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

Reference:
Patent; North University of China; Liu Yucun; Luo Jin; Liu Yan; Chai Tao; (14 pag.)CN106831598; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem