Tag: M.W=100-200

Application of 17334-08-6, A common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, molecular formula is C5H8N2O, 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.

To 1.12 g of 1-methyl-2-imidazolemethanol are added dropwise 1.8 ml of thionyl chloride at 0 C. After 18 hours at 20 C., the mixture is heated at 70 C. for 2 hours. The reaction medium is concentrated to give the expected product quantitatively. 1H NMR delta in ppm (DMSO d6): 3.90 (s, 3H); 5.22 (s, 2H); 5.36 (t, 1H); 7.77 (d, 1H); 7.80 (d, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SANOFI-AVENTIS; US2007/185136; (2007); A1;,
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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 7189-69-7

A solution of 1,1?-sulfonyldiimidazole(119 mg, 0.6 mmol), ethinyl estradiol (9,89 mg, 0.3 mmol), and cesium carbonate (49 mg, 0.15 mmol) in 5 mL of tetrahydrofuran was stirred at 23 C for 18 h, and then was concentrated. The residue was dissolved in 5 mL of ethyl acetate, which was washed sequentially with saturated aqueous ammonia chloride, and brine, dried, concentrated, and then chromatographed on silica with 2:3 ethyl acetate / hexane as the eluant, to provide 116 mg(91%) of 10 as a white solid, mp 168- 170 C : 1H NMR (500 MHz, CDCl3) delta 7.74 (s,1 H), 7.32 (d, 1 H, J = 1.5 Hz), 7.24(d, 1 H, J = 9.5 Hz), 7.17 (s, 1 H), 6.63 (d, 1 H, J = 6.5 Hz),6.60 (d, 1 H, J = 1.5 Hz), 2.80 (d, 2H, J = 4.5 Hz), 2.59 (s, 2 H), 2.39 – 2.28 (m, 2 H), 2.24 – 2.18 (m, 1H), 2.08 – 1.97 (m, 1 H), 1.97 – 1.84 (m, 2 H), 1.84 – 1.59 (m, 3 H), 1.54 -1.22 (m, 4 H), 0.88 (s, 3 H); 13C NMR (126 MHz, CDCl3) delta147.1, 141.2, 139.7, 137.8, 131.4, 127.4, 121.3, 118.6, 118.2, 87.6, 79.9, 74.3, 49.7, 47.2, 43.9, 39.1, 38.9, 32.9, 29.7, 26.9, 26.3,23.0, 12.9; ESI-MS m/z 427.1 MH+.

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 7189-69-7.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 21252-69-7, A common heterocyclic compound, 21252-69-7, name is 1-Octyl-1H-imidazole, molecular formula is C11H20N2, 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.

Synthesis of 1-octyl-3(propyl-3-sulfonyl) imidazolium 1 equivalent of 1 -octyl-imidazole was reacted with 1 equivalent of propanesultone at reflux temperature in 10percent toluene as solvent. After 10 hours, the mixture was cooled down at room temperature and then filtrated. The cake was washed with 3 portions of toluene before drying under high vacuum at 60°C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ECOLE D’INGENIEURS ET D’ARCHITECTES DE FRIBOURG; MARTI, Roger; VANOLI, Ennio; AEBY, Sandrine; FISCHER, Fabian; HAPPE, Manuel; WO2013/8172; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, 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. Application In Synthesis of 5-Bromo-1H-benzo[d]imidazole

[00512] A. tert-Butyl S-bromo-lH-benzofcphimidazole-l-carboxylate. 5-Bromo- l H-benzo[d] imidazole (0.300 g, 1.52 mmol), di-tert-butyl dicarbonate (0.397 g, 1.82 mmol), triethyl amine (0.307 g, 3.04 mmol) and tetrahydrofuran (10 mL) were stirred at 25 C for 18 h. The solution was condensed under reduced pressure and the product was isolated using Biotage silica gel chromatography (0-80% ethyl acetate in hexanes). Fractions containing product were concentrated to give (0.398 g, 88% yield). MS (ESI) m/z 298 [M+ 1]+.

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5400-75-9, These common heterocyclic compound, 5400-75-9, name is 5-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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.

5-Methyl-1 ,3-diotahydro-2H-benzimiotadazol-2-one (13.1 g, 88.5 mmol) and phosphorus oxychloride(130 rmL, freshly distillated) was charged into three-neck round-bottom flask. The mixture was heated up to boiling point till homogeneous solution was formed. After that the dried hydrogen chloride was bubbled through inlet gas-pipe into the reaction mixture. The mixture was boiled for 15 hours. Excess of phosphorus oxychloride was distillated in vacuo. Mixture of ice and water (250 ml_) was added to residue. The obtained suspension was cooled to room temperature and filtered. Filtrate was alkalinized by aqueous ammonia solution till pH 8, cooled by cold water and filtered crude 2-chloro-6-methyl-1H- benzimidazole. White powder was crystallized from aqueous methanol (water-methanol: 1.1 , 200 mL), washed by aqueous methanol and dried in desiccator under Phosphorous oxide in vacuo. Yield. 8.17 g (55 percent).

Statistics shows that 5-Methyl-1H-benzo[d]imidazol-2(3H)-one is playing an increasingly important role. we look forward to future research findings about 5400-75-9.

Reference:
Patent; CRYSOPTIX K.K.; WO2009/109782; (2009); A2;,
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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 33543-78-1

General procedure: A mixture of 0.68 g of imidazole, 2.13 g of oxidant(chloramine-B) in presence of 2.5 cm3 (0.01 mol dm-3) of aqueous perchloric acid was stirred at 303 K for 8?10 h. After completion of the reaction (monitored by TLC), the reaction products were neutralized with alkali and extracted with ether. The organic products were subjected to spottests and chromatographic analysis (TLC technique). Further, the reaction mixture was extracted with ethyl acetate and dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain crude products. The crude products were purified on silica gel column by using petroleum ether and ethyl acetate as solvents to get the pure products. Above analyses revealed the formation of corresponding imidazolones as the oxidation products of imidazoles. 3,5-Dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, 2-ethyl-3,5-dihydroimidazol-4-one,3,5-dihydro-4-oxoimidazol-2-carbaldehyde, and 3,5-dihydro-4-oxoimidazol-2-ester are the oxidation products of1H-imidazole, 2-methyl-1H-imidazole, 2-ethyl-1H-imidazole,1H-imidazole-2-carbaldehyde, and 1H-imidazole-2-ester, respectively. The mass spectra showed a molecularion peak at m/z = 84 amu (Fig. 1), 99 amu (M 1,Fig. 2), and 112 amu (Fig. 3), clearly confirming 3,5-dihydroimidazol-4-one, 2-methyl-3,5-dihydroimidazol-4-one, and 2-ethyl-3,5-dihydroimidazol-4-one as oxidation products of 1H-imidazole, 2-methyl-1H-imidazole, and2-ethyl-1H-imidazole, respectively. Further these productswere confirmed by NMR data (supplementary material,Figs. 1s?3s). Furthermore, we have succeeded in estimating the products, imidazolones, in case of all the five imidazoles. In some typical experiments, the weight of imidazolones and their percentage yield obtained are recorded in Table 1. The recovery of imidazolones was 87?93 percent yields. Further no reaction was noticed between oxidation products and CAB under prevailing experimental conditions.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manjunatha; Puttaswamy; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1517 – 1529;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, 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. HPLC of Formula: C5H5N3

A 25 mL flask is charged with powdered KOH (211 mg, 3.23 mmol), DMSO (3 mL), purged with Argon and is cooled at 10CC with a water bath. A solution of 2-imidazol-1-ylacetonitrile (166 mg, 1.55 mmol) and CS2 (0.195 mL, 3.23 mmol) in DMSO (3 mL) is then added slowly to give an orange mixture. The cooling bath is removed and the reaction is stirred at room temperature for 30 minutes. A solution of [2-chloro-1-(2,5-dichloro-3-thienyl)ethyl] methanesulfonate (400 mg, 1.29 mmol) in DMSO (2 mL) isthen added dropwise. After 30 minutes, the reaction mixture is poured into H20 (15 mL). The aqueous phase is extracted with dichloromethane, the combined organic phases are washed with brine, dried with Na2504, filtered and evaporated to give a crude pale yellow residue. Purification by chromatography on silica gel (heptanes Iethyl acetate, 5:1-* 1:1 -* 1:3) afford (2E)-2-[4-(2,5-dichloro- 3-thienyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile (Compound l.h.25) as a white solid. Mp =117-1 19CC. 1H-NMR (400 MHz, CDCI3): oe = 7.63 (s, 1H), 7.18 (s, 1H), 7.05 (t, J = 1.3 Hz, 1H), 6.96 (s,1H), 5.39 (dd, J= 5.2, 8.7 Hz, 1H), 3.74 (dd, J= 5.2, 11.9 Hz, 1H), 3.63 (dd, J= 8.7, 11.9 Hz, 1H). MS (ESI): m/z= 360, 362 (M+1).

The synthetic route of 2-(1H-Imidazol-1-yl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien Daniel Henri; MAITY, Pulakesh; JEANMART, Stephane Andre Marie; LAMBERTH, Clemens; WO2015/162269; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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.

Example 35: r4-(5-Amino- Pl .3.41 oxadiazol-2-yl)-pyridin-3-vn-f4-bromo-2-chloro- phenvU-amine; To a solution of 3-(4-Bromo-2-chloro-phe?ylamino)-iso?icotinic acid hydrazide (200mg, 0.59mmol, 1eq) in DMSO (2mL) C- (Di-imidazol-i-yl)-methyleneamine (188mg, 1.17mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight and then poured into water. A solid precipitated out that was filtered and washed with methanol to give the desired product (125 mg). LC/MS (Method A) [4.77min; 367(M+1)]

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

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
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. 57531-37-0, name is 2-Chloro-5-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-5-nitroimidazole

Example 3 Preparation of 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole 2-Chloro-4-nitro-1H-imidazole (6.78 g, 46 mmol) and 2-methyloxiran-2-ylmethyl 4-nitrobenzoate (12 g, 51 mmol) were dissolved in ethyl acetate (24 ml), and triethylamine (1.3 ml, 9.2 mmol) was added to the solution. The resulting mixture was stirred under reflux for 14 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml) was added to the residue. The resulting precipitates were filtered off, and dissolved in methanol (120 ml). To the solution, potassium carbonate (318 mg, 2.3 mmol) was added, and the resulting mixture was stirred at room temperature for 1 hour. To the resulting mixture, 6 N hydrochloric acid (0.8 ml) and magnesium sulfate (8 g) were added in this order with cooling on ice-bath, and the resulting mixture was stirred for 30 minutes. Insoluble matters were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. To the residue, ethyl acetate (6 ml) and toluene (60 ml) were added. The resulting precipitates were filtered off and dried at 50C to afford 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole (7.88 g, yield 72%) as a white powder. 1H-NMR (DMSO-d6) deltappm: 1.02 (3H, s), 3.25 (2H, d, J = 5.3 Hz), 4.04 (2H, s), 4.98 (1H, s), 5.10 (1H, t, J = 5.4 Hz), 8.29 (1H, s).

According to the analysis of related databases, 57531-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP1555267; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17228-38-5, 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. 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

2-((5R,8aS)-3-Chloro-5-methyl-5,6,8a,9-tetrahydro-8H-7, 1 0-dioxa-2,4,4b-triaza-phenanthren-1 -yl)-propan-2-ol (154,51 mg; 0,500 mmol; 100,00 mol%), (1H-benzimidazol-2-yl)-methyl-amine (73,59 mg; 0,500 mmol; 100,00 mol%), tris(dibenzylideneacetone)dipalladium(0) (91,57 mg; 0,100 mmol; 20,00 mol%) and dicyclohexyl-(2?,4?,6?-triisopropyl-biphenyl-2-yl)-phosphane (95,34 mg; 0,200 mmol; 40,00 mol%) were dissolved in dioxane (1,36 ml; 15,845 mmol;31 69,00 mol%), lithium tert-butoxide (1,0 M solution in tetrahydrofuran)(700,00 p1; 0,700 mmol; 140,00 mol%) was added and the mixture was stirredfor 1 h at 80 00. The reaction mixture was purified by column chromatography(petroleum benzene I ethyl acetate) to afford the product as yellow solid(14.8mg, 6.5%); LCMS (method C): 1 .29 mm (purity 89.6%); [MH+] 411 .3 mlz;1H NMR (400 MHz, DMSO-d6)o 13.08 (5, 1H), 7.42 (d, J 7.1 Hz, 1H), 7.37-7.23 (m, 1 H), 7.16-7.00 (m, 2H), 5.37 (5, 1 H), 4.69-4.57 (m, 1 H), 4.35 (dd,J = 10.9, 3.2 Hz, 1 H), 3.97 – 3.84 (m, 2H), 3.81 (d, J = 11 .5 Hz, 1 H), 3.74 -3.71 (m, 1 H), 3.65 (dd, J = 11 .6, 3.3 Hz, 1 H), 3.29 (5, 3H), 3.23 – 3.09 (m, 1 H),1 .52 (5, 3H), 1 .51 (5, 3H), 1 .27 (d, J = 6.8 Hz, 3H).

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

Reference:
Patent; MERCK PATENT GMBH; BURGDORF, Lars; DORSCH, Dieter; TSAKLAKIDIS, Christos; (189 pag.)WO2017/202748; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem