Tag: M.W=100-200

These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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. 16042-25-4

General procedure: Conc. H2SO4 (27.5 mL, 516 mmol) was added slowly to 1H-imidazole-2-carboxylic acid (5 g, 44.6mmol) followed by drop wise addition of fuming HNO3 (5 mL). The reaction was then heated to 80 C for 5.5 hr. The reaction was cooled to rt, then added drop wise over crushed ice. The precipitate was then filtered and dried under vacuum overnight to yield a pale lemon solid (3.8 g, 54%). LCMS (Waters Atlantis: Gradient Method 1): Rt = 1.35 min, 99 A% 254 nm, [M + H]+ = 158.0. 1H NMR(400 MHz, DMSO) delta 14.38 (s, 1H), 8.48 (s, 1H). 13C NMR (150 MHz, CDCl3) delta 158.8, 147.3, 136.8,121.6. HRMS (ESI): m/z calcd for C8H6N6NaO8 [2M + Na]+, 337.0139; found, 337.0151.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16042-25-4.

Reference:
Article; Jarrad; Debnath; Miyamoto; Hansford; Pelingon; Butler; Bains; Karoli; Blaskovich; Eckmann; Cooper; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 353 – 362;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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) In a 250mL three-necked flask, purged with nitrogen, 0.02mol raw material 2-bromo-1H-benzimidazole, 0.03mol iodobenzene, 0.04mol sodium hydride,0.004mol cuprous iodide and 0.01mol o-phenanthroline dissolved in 100ml 1,3-dimethyl-2-imidazolidinone, the reaction was stirred for 20-30h,After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate,A mixture of petroleum ether and ethyl acetate was used as a eluent shower, the volume ratio of petroleum ether to ethyl acetate in the eluent was 1: 100,Purification by column chromatography gave Intermediate M1; HPLC purity 99.5%, yield 75.8%.

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

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Zhang Zhaochao; Li Chong; (51 pag.)CN107417668; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

46006-36-4, 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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Into a 250-mL round-bottom flask, was placed a solution of 1H-1,3-benzodiazole-4- carboxylic acid (4.0 g, 24.67 mmol, 1.00 equiv) in methanol (60 mL), and sulfuric acid (6 mL). The resulting solution was stirred overnight at room temperature then concentrated under vacuum. The resulting solution was diluted with 30 mL of sodium chloride (aq) then extracted with EtOAc (2 x 30 mL) and the organic layers were combined. The pH value of the aqueous layer was adjusted to >7 with NaHCO3 (2M) and was extracted with EtOAc (2 x 30 mL). All EtOAc solutions were then combined and concentrated under reduced pressure to provide methyl 1H-1,3-benzodiazole-4-carboxylate as a red solid (2.5 g, 58% yield).

The synthetic route of 1H-Benzimidazole-7-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 1-Methyl-1H-imidazole-4-carboxylic acid 4-[3-hydroxy-4-(3-methyl-butyryl)-2-trifluoromethyl-phenoxymethyl]-benzylamide Mix 1-[4-(4-aminomethyl-benzyloxy)-2-hydroxy-3-trifluoromethyl-phenyl]-3-methyl-butan-1-one hydrochloride (120 mg, 287.2 mumol), 1-methyl-1-H-imidazole-4-carboxylic acid (43.5 mg, 344.6 mumol), 1-hydroxybenzotriazole hydrate (52.8 mg, 344.6 mumol) in anhydrous tetrahydrofuran (4.5 mL). Add triethylamine (72.7 mg, 718 mumol, 100 muL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66.1 mg, 344.6 mumol) to the mixture. Stir the reaction mixture at room temperature overnight. Dilute the reaction mixture with water. Extract the mixture with ethyl acetate (3*). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate under reduced pressure. Purify the crude residue by flash chromatography (silica gel) eluding with 5percent methanol/ethyl acetate followed by reverse phase chromatography using 90/10 to 20/80 (water/0. 1percent trifluoroacetic acid)/acetonitrile to provide the product as a white solid (75 mg, 153 mumol, 53.4percent yield). MS (m/z): 490 (M+1).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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

1977-72-6, A common compound: 1977-72-6, name is 5-Fluoro-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Intermediate VI-10 5-fluorobenzimidazole (0.28 g, 2.04 mmol) was added to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.20 mmol) and acetonitrile as a solvent at 50 C for 40 minutes,After cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C and the mixture was traced to the end of the reaction.After further concentration, extraction, column chromatography separation, drying and the like, the intermediate X-10 (0.49 g) is obtained, the yield is 73.4%;White solid,

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

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei¡¤lamohan¡¤laao¡¤yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, molecular formula is C5H6N2O2, 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. 22884-10-2

Example 1; [0022] An oven-dried 250 ml_ 4-neck RB flask was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet and two 1/8 inch polytetrafluoroethylene (PTFE) feeding lines. The system was flushed with nitrogen for 30 minutes. Under nitrogen protection, imidazoIe-1-ylacetic acid (15.97 g, 0.13 mole), sulfolane (70 ml_) and phosphorous acid (2.67 g, 0.033 mol) were charged to the RB flask. The reaction mixture was mixed at 210 RPM and heated to 600C. PCI3 (9.18 g, 0.067mol) was added slowly (1.3 mL/mn) via a masterflex tubing pump. Five minutes were allowed for mixing. Alternately fed were 26 wt% phosphorous acid sulfolane solution (30.7 g, 10.23 g each addition at 1.6 mL/min) and PCI3 (27.5 g, 9.18 g each portion at 1.3 mL/min). Three to five minutes of mixing were allowed between additions. The addition took 1 hr 3 min and temperature was maintained between 600C and 670C. After addition was complete, the temperature of the reaction mixture was raised to 800C and was held at this temperature for 4 hours. Then the temperature of the reaction mixture was raised to 880C and held for 30 minutes. Ambient temperature water (50 g) was added in to quench the reaction. The solution was refluxed for 3 hrs . temperature, the product was vacuum-filtered and rinsed with 38 g of acetone. Zoledronic acid was obtained as a white crystalline solid (24.1 g, 95.3wt% purity by quantitative NMR, 65% yield). Example 2; [0023] An oven-dried 250 mL 4-neck RB flask was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet and two 1/8 inch PTFE feeding lines. The system was flushed with nitrogen for 30 minutes. Under nitrogen protection, imidazole-1-ylacetic acid (15.97 g, 0.13 mole), sulfolane (70 mL) and phosphorous acid (2.67 g, 0.033 mol) were charged to the RB flask. The reaction mixture was mixed at 300 RPM and heated to 600C. PCI3 (9.18 g, 0.067mol) was added in slowly (1.3 mL/min) via a masterflex tubing pump. Five minutes were allowed for mixing. Alternately fed were 26 wt% phosphorous acid sulfolane solution (30.7 g, 10.23 g each addition at 1.6 mL/min) and PCI3 (27.5 g, 9.18 g each portion at 1.3 mL/min. Three to five minutes of mixing were allowed between additions. The addition took 1 hr 6 min and temperature was maintained between 54 and 64C. After addition was complete, the temperature of the reaction mixture was raised to 800C and held for 4 hours. Then the temperature of the reaction mixture was raised to 880C and held for 30 minutes. This slurry was transferred via 3/8″ PTFE tubing using nitrogen pressure into 100 mL of pre-heated (80C) water under mixing. The resultant water solution was heated to refluxing and held at that temperature for 4 hr. It was then slowly cooled to room temperature then to 1-2C and held for 1.5 hr at this temperature. The product was collected via vacuum filtration. The cake was rinsed with acetone (20 g) and zoledronic acid was obtained as a white crystalline solid (19.1 g, 98.3 wt% purity by quantitative NMR, 53% yield). Example 3; [0024] An oven-dried 250 mL 4-neck RB flask was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet and two 1/8 inch PTFE feeding lines. The system was flushed with nitrogen for 30 minutes. Under nitrogen protection, imidazole-1-ylacetic acid (15.9 g, 0.13 mole), sulfolane (70 mL) and phosphorous acid (2.67 g, 0.033 mol) were charged to the RB flask. The reaction mixture was mixed and heated to 6O0C. PCI3 (36.7 g, 0.267 mol) and phosphorous acid (8.0 g, 0.098 mol) in – . mL/min respectively. Reaction temperature remained between 6O0C and 67C during feeding, After addition of PCI3 and phosphorous acid, the reaction slurry was heated to 800C and held at that temperature for 4 hours. This slurry was then transferred via 3/8″ PTFE tubing using nitrogen pressure into 50 m._ of pre-heated (8O0C) water under mixing. The resultant water solution was heated to refluxing and held at that temperature for 4 hr. It was then slowly cooled to 48-500C. Acetone (200 ml_) was added in slowly and then it was cooled to 1-2C and held for 2 hr at this temperature. The product was collected via vacuum filtration. The cake was rinsed with acetone (35 g) and zoledronic acid was obtained as a white crystalline solid (22.1 g, 98.6 wt% purity by quantitative NMR, 61 % yield). Example 4; [0025] A 2.5 L resin-kettle was fitted with a mechanic stirrer, K-thermocouple, condenser, nitrogen inlet and outlet, two 1/8 inch PTFE tubing as PCI3 and phosphorous acid sulfolane solution feeding lines. The system was dried under a stream of nitrogen. Under nitrogen, imidazoleacetic acid (79.92 g, 0.63 mol), phosphorous acid (13.90 g, 0.17 mol) and sulfolane (350 ml_) were added to the resin-kettle and mixed at 200 RPM. The mixture was heated to 62C then PCI3 (36.7 g, 0.267 mol) was added in slowly (1.3 mL/min) using a masterflex tubing pump. The slurry was mixed for 5 minutes. Phosphoro…

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22884-10-2, its application will become more common.

Reference:
Patent; ALBEMARLE CORPORATION; WO2008/157050; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

52099-72-6, 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. 52099-72-6 name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, 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.

Example V To a stirred solution of 8.5 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one in 45 Parts of N,N-dimethylformamide are added portionwise 1.7 parts of sodium hydride dispersion 78%. After stirring for 1 hour at room temperature, the whole is cooled to 0-5 C and 8.65 parts of 1-bromo-3-chloropropane are added dropwise (slowly). Upon completion, stirring is continued for 3 hours at room temperature. The reaction mixture is poured onto crushed ice and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 5.5 parts (44%) of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one; mp. 115 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4035369; (1977); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2301-25-9,Some common heterocyclic compound, 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, molecular formula is C9H7N3O2, 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 1-(substituted) 4-nitrobenzene IVa,b,e,f(0.01 mol) in NH4OH (20 mL, 30%), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va,b,e,f. 4-(1H-imidazol-1-yl) aniline Va Yield 70% as gray solid, mp 147 C, (as reported) [64,65].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2301-25-9, its application will become more common.

Reference:
Article; Abdel-Atty, Mona M.; Farag, Nahla A.; Kassab, Shaymaa E.; Serya, Rabah A.T.; Abouzid, Khaled A.M.; Bioorganic Chemistry; vol. 57; (2014); p. 65 – 82;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3752-24-7, 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. 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of Intermediate VI (50 mg, 0.12 mmol) in N,N-dimethylformamide (2 mL) were added phenol (17 mg, 0.18 mmol) and cesium carbonate (76 mg, 0.23 mmol). The resulting mixture was stirred for 12 h at 100C. The reaction mixture was then cooled and quenched with water (50 mL), after which the reaction mixture was extracted with dichloromethane (3 x 25 mL). The organic extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under vacuum to give a residue, which was purified by reverse phase preparative HPLC [Column: Xbridge Prep C18 5 m OBD, 19 x 150 mm; Mobile phase: A: Water (10 mM NH4HCO3), B: acetonitrile (22% – 40%); Flow rate: 20 mL/min; UV detection: 220/254 nm] to afford compound 8-5. Compound 8-8 was prepared in an analogous fashion to Example 19C, using 4,5,6,7-tetrahydro- 1 H-benzo[d]imidazole instead of phenol.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; ALTMAN, Michael D.; DENG, Yongqi; KATTAR, Solomon; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; MCGOWAN, Meredeth; CHRISTOPHER, Matthew P.; GARCIA, Yudith; ANTHONY, Neville John; FRADERA LLINAS, Francesc Xavier; YANG, Liping; MU, Changwei; WANG, Xiaona; SHI, Feng; YE, Baijun; ZHANG, Sixing; ZHAO, Xiaoli; ZHANG, Rong; FONG, Kin Chiu; LENG, Xiansheng; WO2014/75393; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, Adding some certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 3314-30-5.

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3314-30-5.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem