Tag: M.W=100-200

Synthetic Route of 5805-57-2, 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. 5805-57-2 name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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.

General procedure: The 4-chloro-6-methylpyrimidin-2-amine (1) (1 mmol)was dissolved in dry ethanol (5 ml). To this, (benzoxazol-2-yl)methanamine (3a)/(benzothiazol-2-yl)methanamine (3b)/(1H-benzimidazol-2-yl)methanamine (3c) (1.1 mmol) and acatalytic amount of methanesulfonic acid (0.2 ml) wereadded and refluxed for 4-6 h. After completion of thereaction, the reaction mixture was cooled and diluted withwater (15 ml). The separated solid was filtered, washed withwater, dried and recrystallized from 2-propanol.

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

Reference:
Article; Seenaiah, Dandu; Rekha, Tamatam; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 2; (2017); p. 431 – 441;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1122-28-7, name is 4,5-Dicyanoimidazole, A new synthetic method of this compound is introduced below., Safety of 4,5-Dicyanoimidazole

Example 19 2-Bromo-4,5-dicyanoimidazole (21) STR70 To 1.18 g (10 mmol) 4,5-dicyanoimidazole and 25 ml 0.1 M NaOH was added 1.8 ml Br2 (35 mmol). The mixture was stirred overnight at room temperature and then acidified with dilute HCl. The solid was filtered, rinsed with water and recrystallized from water to give 1.5 g of dicyanobromoimidazole 21 (yield 76.4%).: m.p. 147-149 C. (lit. 141-143 C.); Rf=0.65 (ethyl acetate_methanol=4:1); MS(EI): 198([M+2], 96%), 196 ([M+ ], 100%), 171 (28.5), 169 (29.2), 117 (27.4), 91 (19.0), 64 (20.6), 53 (22.4), 38 (18.8).

The synthetic route of 1122-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Isis Pharmaceuticals, Inc.; McGill University; US6160109; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0, SDS of cas: 60-56-0

General procedure: To a slurry of the substituted imidazole-2-thione or pyrimidine-2-thiol (1.0 mmol) and sodium methoxide (2.2 mmol) in methanol (20 mL) was added a solution of substituted 2-(chloromethyl)-pyridine (1.0 mmol) in methanol (10 mL). After the mixture was refluxed with stirring for 4-6 h, the solvent was removed in vacuo and the residue was washed with water to remove the salt, and then extracted with dichloromethane (3 9 10 mL) at room temperature. The solid product was directly obtained by the removal of solvent and further dried at 45 C overnight. The purity of the product was tested by HPLC and characterization of the product was confirmed by IR, 1H NMR, and mass spectroscopies. Data 3-Methyl-[4-(2,2,2-Trifluoroethoxy)-2-Pyridinyl]-Methylthio-1-Methyl-Imidazole (3a) White solid. Yield: 84.5 %. IR (cm-1): 832.7 (-CH2-S-). 1H NMR (CDCl3) delta (ppm): 2.18 (s, 3H, -CH3 in py), 3.23 (s, 3H, -CH3 in imidazole), 4.42 (q, J = 6.0 Hz, 2H,-OCH2CF3), 4.56 (s, 2H, -CH2S-), 6.62 (d, J = 5.6 Hz,1H, H in py), 6.81 (s, 1H, H in imidazole), 6.92 (s, 1H,H in imidazole), 8.30 (d, J = 5.6 Hz, 1H, H in py). MS (EI): m/z calcd. C13H14N3OF3S (M+) 317.3311, found 317.3336.

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:
Article; Ma, Sen; Jia, Ai-Quan; Fan, Fang-Fang; Shi, Hua-Tian; Zhang, Qian-Feng; Journal of Chemical Crystallography; vol. 46; 3; (2016); p. 137 – 143;,
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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-1H-imidazole-2(3H)-thione

General procedure: To a stirred suspension of potassium carbonate (0.166 g, 1.2mmol) in ethanol (8 mL) was added 1H-imidazole (0.068 g,1 mmol). The mixture was stirred at 60 C for 1 h and thencooled to room temperature. Compound 3 (0.232 g, 1 mmol)was added and stirred under 70 C. After the reaction wascompleted (monitored by TLC, chloroform/methanol, 30:1,V/V), the solvent was evaporated and the residue was treatedwith water (15 mL) and extracted with chloroform (315mL). The combined organic phase was dried over anhydroussodium sulfate and concentrated under the reduced pressure.The crude product was purified by silica gel column chromatography(eluent, chloroform/methanol, 50:1-30:1, V/V)to afford the pure compound 4a (0.142 g) as white solid

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Peng, Xin-Mei; Kumar, Kannekanti Vijaya; Damu, Guri L.V.; Zhou, Cheng-He; Science China Chemistry; vol. 59; 7; (2016); p. 878 – 894;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., Safety of 1H-Imidazole-4,5-dicarboxylic acid

General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Anuj; Banerjee, Somesh; Roy, Partha; Sondhi; Sharma, Anuj; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 501 – 504;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3314-30-5,Some common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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 flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzo[d]imidazole-2-carbaldehyde, its application will become more common.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 22884-10-2, Product Details of 22884-10-2

Step 1: methyl 14-cyclohexl-3-fluoro-6-( 1 H-imidazol-1 -ylacetyl)-5.6,7,8-tetrahydroindolo[2.] -a] (2,5 lbenzodiaz.ocine-11 -carboxylate; To a solution of 1 eq of methyl-14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,l- a][2,5]benzodiazocin-l 1-carboxylate (prepared as described in Example 18, Step 5 ) in DCM (0.06 M), 1.1 eq of imidazo-1-yl acetic acid in DCM (0.05 M), 3 eq of DIPEA and 1.5 eq of TBTU were added and the mixture stirred at RT overnight. Volatiles were removed in vacuo and the crude material was used in the next step without further purification; MS (ES+) m/z 515 (M+Eta)+. EPO Step 2: 14-cyclohexyl-3-fluoro-6-(lH-imidazol-l-ylacetyl)-5.6.7,8-tetrahydroindolof2.1- alf2.5 Ibenzodiazocine- 11 -carboxylic acid

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-(1H-Imidazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); 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 6160-65-2 as follows. Computed Properties of C7H6N4S

To a suspension of 4-bromo-3-chloro-5-(trifluoromethyl)aniline (15 g, 54.7 mmol, Eq: 1.00) in dichloromethane (13.2 g, 10.0 ml, 155 mmol, Eq: 25.3) at 0, was added 1,1′- thiocarbonyldiimidazole (11.7 g, 65.6 mmol, Eq: 1.2) The reaction was gradually warmed to room temperature and stirred overnight. The reaction was concentrated and chromatographed (220g Redisep, 5 to 15% dichloromethane/hexane) to give 13.84 g (80%) pale yellow oil.

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135422; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39021-62-0, 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial equipped with a stir bar was charged with the recovered amine 62 and product mixture (0.330 mmol, 1 equiv.), 43.3 mg of l-methyl-lH-imidazole-4-carbaldehyde (0.390 mmol, 1.2 equiv.), 0.019 mL of CH3COOH (0.330 mmol, 1 equiv.) and 3.4 mL of CH2CI2 and stirred at rt for 3 h. Then 111 mg of NaBH(OAc)3 (0.520 mmol, 1.6 equiv.) was added. After stirring at rt for 12 h, the reaction mixture was quenched by addition of sat. NaHCCb solution and sat. Na2CCb sol., and the product was extracted with CH2CI2 (3x) and dried over Na2S04. The crude product was purified on silica gel column (12 g) using 0-30 % MeOH in EA as eluent affording 116 mg (43%) of N-((S)-3-((R)-3-(((4-(l,3-dioxoisoindolin-2-yl)butyl)((S)-5,6,7,8-tetrahydroquinolin-8- yl)amino)methyl)-4-((1 -methyl- lH-imidazol-5-yl)methyl)piperazin- 1 -yl)- 1 -phenylpropyl)-4,4- difluorocyclohexane-l -carboxamide 78 as a yellowish foam.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-5-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; ALTAS TAHIROVIC, Yesim; WILSON, Lawrence; PELLY, Stephen Christopher; (102 pag.)WO2019/183133; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 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.

General procedure: Two different solutions for feeds A and B were separately prepared in 2 mL vial equipped with a Teflon septum and magnetic stir bar. Feed A: [Ir(dtbbpy)(ppy)2][PF6] (2.00 lmol, 0.01 equiv) and Boc-Pro-OH (0.3 mmol, 1.5 equiv) in 1 mL of DMA; Feed B: NiCl2 glyme (0.02 mmol, 0.1 equiv), 4,4′-di-tert-butyl-2,2′-bipyridyl (0.03 mmol, 0.15 equiv), the corresponding aromatic halides (0.20 mmol, 1.0 equiv), DBU (0.3 mmol, 1.5 equiv) in 1 mLof DMA. The two solutions were degassed by bubbling nitrogen stream for 20 min. Feeds A and B were injected simultaneously into the photoreactor, mixed in a T-mixer, and passed through a 10 mL residence time coil (0.8 mm inner diameter, 4 m length, fluoropolymer tube) irradiated with blue LED 450 nm and heated atthe indicated temperature. The reaction mixture collected from the output was diluted with saturated aqueous NaHCO3 solution,extracted with Et2O (3 10 mL). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentratedin vacuo. Purification of the crude product by flash chromatography on silica gel using as eluent heptane/ethyl acetate afforded the desired product.

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:
Article; Abdiaj, Irini; Alcazar, Jesus; Bioorganic and Medicinal Chemistry; vol. 25; 23; (2017); p. 6190 – 6196;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem