Tag: M.W=100-200

Synthetic Route of 19225-92-4,Some common heterocyclic compound, 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, molecular formula is C5H7ClN2, 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.

To a stirred solution of 4-bromo-5-(piperazin-1-yl)-2,3-dihydropyridazin-3-one (80 mg, 0.31 mmol, 1 equiv.) and DIEA(119.7 mg, 0.93 mmol, 3 equiv.) in DMF(4 mL) was added 2- (chloromethyl)-1-methyl-1H-imidazole(60.5 mg, 0.46 mmol, 1.5 equiv.) in portions at rt overnight. The reaction liquid was purified by Prep-HPLC with the following conditions (Column: XBridge Prep C18 OBD Column, 5um,19*150mm ; Mobile Phase A: Water(10 mmol/L NH4HCO3), Mobile Phase B: MeCN; Flow rate: 20 mL/min; Gradient: 5% B to 28% B in 7 min; 254 nm; Rt: 6.32 min) to afford 4-bromo-5-[4-[(1-methyl-1H-imidazol-2- yl)methyl]piperazin-1-yl]-2,3-dihydropyridazin-3-one (33.3mg,30.53%) as a white solid

The synthetic route of 19225-92-4 has been constantly updated, and we look forward to future research findings.

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. 5465-29-2, name is 2-Propylbenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Propylbenzimidazole

[Example 1] (E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (compound 1) (E)-2-(2-Bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (648 mg, 2.00 mmol) obtained in Reference Example B1 and 2-propylbenzimidazole (385 mg, 2.40 mmol) were dissolved in DMA (2 mL), potassium carbonate (553 mg, 4.00 mmol) was added, and the mixture was stirred at room temperature for 14 hr. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=97/3) to give the title compound (compound 1) (778 mg, 96%). ESI-MS m/z: 404 (M + H)+; 1H-NMR (CDCl3, delta): 1.01 (t, J = 7.4 Hz, 3H), 1.85-1.90 (m, 2H), 2.79 (t, J= 7.6 Hz, 2H), 3.06 (br s, 4H), 5.29 (s, 2H), 5.67 (s, 1H), 6.79-6.88 (m, 2H), 7.11-7.35 (m, 7H), 7.43 (dd, J = 7.3, 1.7 Hz, 1H), 7.76 (d, J = 7.3 Hz, 1H).

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 5465-29-2.

Synthetic Route of 17334-08-6, 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. 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows.

1-Methyl-2-hydroxymethyl imidazole (15.0 g, 134 mmol) was added, with shaking and exclusion of moisture, over a period of 15 min to ice cooled thionyl dichloride (24.6 mL, 30 g, 0.25 mol). The reactants were then heated under reflux for 15 min. The cooled solution was evaporated under reduced pressure followed by recrystallization from ethanol (25 mL) and dried under high vacuum to give 2-(chloromethy1)-1-methyl-1H-imidazole hydrochloride as brown crystals. Yield: 15.1g, 88%. 1H NMR (CDCl3) delta ppm: 7.79 (s, 1H), 7.70 (s, 1H), 5.2 (s, 2H), 3.86 (s, 3H). 3C NMR (CD3OD) delta ppm: 142.05, 124.7, 119.08, 33.9, 31.4. TOF-MS m/z: 131.0384 (M+H+, 100%). Molecular formula of cation, C5H7N2Cl, calculated m/z of cation: 131.04 (M+H+)

The chemical industry reduces the impact on the environment during synthesis (1-Methyl-1H-imidazol-2-yl)methanol. I believe this compound will play a more active role in future production and life.

934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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. SDS of cas: 934-32-7

General procedure: Amine (1 mmol) was added to the mixture of (Boc)2O (1 mmol) and DSIMHS (6.5 mg, ~ 0.02 mmol) with constant stirring at room temperature under solvent-free conditions. After completion of the reaction (monitored by TLC), ethyl acetate (3 × 5 mL) was added to the reaction mixture and the catalyst was decanted and washed with ethyl acetate (2 × 5 mL) and dried. The product was purified by column chromatography, using ethyl acetate-petroleum ether (2:8) eluent.

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference of 93-84-5, The chemical industry reduces the impact on the environment during synthesis 93-84-5, name is 5-Nitro-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

5-Nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one (0.837 mmol,1 eq, 0.15 g) was dissolved in ethanol (5 mL). SnCl2 ·2 H2O(4.187 mmol, 5 eq, 0.94 g) was added to the solution and the system was cooled to 0 C. Afterwards, 37% HCl (0.5 mL) was added dropwise.The reaction mixture was stirred at 0 C for 10 min, then itwas let warm to room temperature and then was heated to 75 C.The reaction mixture was stirred at this temperature for 3 h andthen left overnight (10 h) at room temperature. The next morning the reactionwas cooled to 0 C and quenched by dropwise additionof a saturated aqueous solution of NaHCO3 till pH 7-8. The product was extracted with ethyl acetate (3 x 10 mL). The combined organiclayers were washed with a saturated aqueous solution of NaCl(2 x 5 mL) and then dried over Na2SO4, filtered and concentrated invacuo. The extract was purified by silica gel chromatography elutingwith chloroform: methanol 8:1, to afford the amine 7; -benzo[d]imidazol-2-one (0.365 mmol, 54.5 mg, Y 44%). m.p. 253-256 C(methanol). 1H NMR (DMSO-d6, 400 MHz, delta; ppm) deltaH: 6.21-6.24(1H, dd, J = 2 Hz, 8.2 Hz, C(4)H), 6.29 (1H, d, J = 2 Hz, C(2)H), 6.63(1H, d, J = 8 Hz, C(5)H), 10.08 (1H, bs, N(1)H), 10.23 (1H, bs, N(2)H)ppm. 13C NMR (DMSO-d6, 100 MHz, delta; ppm) deltaC: 95.4, 106.7, 108.6,119.9, 130.2, 143.1, 156.4 ppm. MS (EI) m/z [M]+:149.07.

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-Nitro-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

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. Product Details of 492-98-8

A mixture of Zn(NO3)2 6H2O (44.6mg,0.15mmol),5-Brnic(60.6 mg,0.3mmol),H2biim (20.1mg,0.15mmol),NaOH(12.0mg,0.3 mmol),and H2O (10mL)was stirred at room temperature for 15min,and then sealed in a25mL Teflon-lined stainless steel vessel,and heated at 160 1C for 3days,followed by cooling to room temperature at a rate of 10 1C/h. Colorless block-shaped crystals were isolated manually,and washed with distilled water.Yield: 55%(basedon5-BrnicH).CalcdforC24H14Br2ZnN4O4:C 44.51%,H2.18%,N8.65%.Found:C44.17%,H1.84%,N8.24%.IR (KBr,cm1): 1609vs,1552m,1441m,1394w,1370vs,1342w,1281m,1237w,1181w,1125s,1088w,1028m,991w,925w,887w,862w,771m,754m,732m,687m,553w,and434w.

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

Reference:
Article; Gu, Jin-Zhong; Wu, Jiang; Kirillov, Alexander M.; Lv, Dong-Yu; Tang, Yu; Wu, Jin-Cai; Journal of Solid State Chemistry; vol. 213; (2014); p. 256 – 267;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-1H-imidazole, 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 2302-25-2, SDS of cas: 2302-25-2

Step 1: To a stirred mixture of DMF (15 mL) and NaH (60% dispersion in mineral oil, 539 mg, 21 mmol) at 0C under argon was added 4-bromo-1H-imidazole (3 g, 20 mmol) in one portion. The mixture was stirred for 5 min at 0C. A solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.3 mL, 24 mmol) in DMF (3 mL) was added dropwise. Afterstirring at 0 C for 1 h, the mixture was warmed slowly to rt and stirred for 6 h. The mixture was then partitioned betweenEtOAc (100 mL) and water (50 mL). The EtOAc layer was separated and washed with brine, dried over Na2SO4, filtered,and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel flash chromatography(eluting with a gradient of 100% hexanes to 100% EtOAc) to afford a regioisomeric mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole as an oil (2.9 g, 53%).LCMS (ESI) m/z 277 and 279 (M+H)+. Step 1: To a mixture of the regioisomers 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo,-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (643 mg, 2.3 mmol) from Step 1 of Example 32, acetamide(275 mg, 5.0 mmol), and Cs2CO3 (1.5 g, 5 mmol) in 1,4-dioxane (7 mL) was added N,N?-dimethylethylenediamine (500mL, 5 mmol). Argon was bubbled into the mixture for 5 min followed by the addition of CuI (221 mg, 1.1 mmol). Argonwas bubbled into the mixture for an additional 5 min. Then the reaction vessel was sealed and the mixture was heatedat 100 C for 15 h. The mixture was cooled to rt, then partitioned between EtOAc (100 mL) and water (50 mL). TheEtOAc layer was separated, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure.The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 100% EtOAc toafford a mixture of regioisomers N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)acetamide and N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)acetamide (170 mg, 29%) as an oil. LCMS (ESI) m/z 256 (M+H)+.

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; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 705-09-9, 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 705-09-9 as follows.

Reagents and conditions: (a) morpholine, DIPEA, DCM, -78C – RT, 84.7%; (b) 2-(difiuoromethyl)-lH-benzimidazole, K2C03, DMF, RT, 85.5%; (c) piperazine, THF, reflux, 75.9%; (d) 02N-(CH2)5C0C1, Et3N, CHC13, RT, 92.5%; (e) HCOONH4, 10% Pd-C, CH3OH, -10C- RT, 56.6%.

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; REHEMTULLA, Alnawaz; GALBAN, Stephanie; ROSS, Brian, D.; VAN DORT, Marcian; WHITEHEAD, Christopher; WO2014/164942; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 3287-79-4, name is 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione, 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: 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione

Example 13. 2-[2-(Pyrrolidino)ethylthio]-5,6-dimethylbenzimidazole (XIII) and its dihydrochloride were synthesised as described above. The compound XIII was obtained from 2,67 g (0,015 mol) 2-mercapto-5,6-dimethylbenzimidazole and 2,9 g (0,017 mol) 2-(pyrrolidino)ethylchloridehydrochloride in the presence 1,35 g (0,034 mol) sodium hydroxide in 90% yield (4,0 g, counting on monohydrate), m.p. 115-116 C. (with decomp., from ethanol with water). 1H NMR (CDCl3), delta: 1,97 (4H, m, beta-H of pyrrolidine); 2,34 (6H, s, 2CH3); 2,72 (4H, m, -H of pyrrolidine); 3,02 (2H, m, CH2S); 3,19 (2H, m, CH2N); 7,18 (2H, broad s, ArH). Calcd for C15H21N3S*H2O: C 61,4; H 7,8; N 14,3; S 10,9; Found: C 61,4; H 7,8; N 14,5; S 10,9.

The synthetic route of 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nauchno-Issledovatelsky Institut Farmakologii Rossiiskoi Akademii Meditsinskikh Nauk; US6376666; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5805-57-2, 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 5805-57-2 as follows.

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem