Tag: M.W=100-200

Electric Literature of 1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-1-methyl-1H-imidazole (10.4 g, 64.4 mmol) in THF (100 mL) under a nitrogen atmosphere in an ice bath. A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, Intermediate 1: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHCO3. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2SO4), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of EtOAc:heptanes (1:1, 150 mL). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

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; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 934-32-7, 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 934-32-7 as follows.

General procedure: In a 50-mL round-bottomed flask, a mixture of 2-aminobenzimidazole 1 (2 mmol), aldehyde 2a-p (2 mmol), 1,3-cyclohexadione 3 (2 mmol), and deep eutectic solvent (5 mL) was stirred at 80 C for specified time (Scheme 2, Table 2). After reaction completion (monitored by TLC), the reaction mixture was cooled to room temperature then poured into crushed ice to obtain solid product, which was filtered, dried, and recrystallized from ethanol to afford pure product.

According to the analysis of related databases, 934-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mahire, Vilas N.; Patel, Vijay E.; Mahulikar, Pramod P.; Research on Chemical Intermediates; vol. 43; 3; (2017); p. 1847 – 1861;,
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., COA of Formula: C4H6N2S

3-hydroxysalicylaldehyde 5 (1 mmol), malononitrile 6 (2.1 mmol), 2-mercapto-1-methylimidazole 7 (1.1 mmol), Compound 4 (22 mol%) and ethanol (5 mL) were sequentially added to a 50 mL round bottom flask, and fully reacted to completion at 80 C (TLC followed Trace monitoring). After cooling to room temperature, suction filtration, the product was washed with a small amount of water, dissolved in N,N-dimethylformamide, filtered, and filtered. Distilled water was added, and a solid was precipitated, suction filtered, and recrystallized (DMSO) to give compound 8b in a yield of 83%.8b C17H13N6O2S 2,4–9–5-(1–1H–2-)-5H-[2, 3-b]-3- 2,4-diamino-9-hydroxy-5-(1-methyl-1H-imidazol-2-ylthio)- 5H-chromeno[2,3-b]pyridine-3-carbonitrile

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 60-56-0.

Reference:
Patent; Jiangsu Normal University; Wu Hui; Yuan Rui; Ren Xuanxuan; Fang Yue; Chen Wen; Zhou Shengliang; Zhang Peng; Wan Yu; (15 pag.)CN108610348; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10597-52-1, A common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, 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 a suspension of sodium hydride (0.014 g, 0.607 mmol) in dry DMF (5 mL) under Ar in an ice bath was added solid Intermediate 15 (0.090 g, 0.552 mmol) in one portion, and then the ice bath was removed. After 30 minutes at room temperature, the reaction was returned to an ice bath, then ethyl iodide (0.049 ml, 0.607 mmol) added dropwise, and the reaction stirred cold. The bath was removed, and the reaction stirred at room temperature for 12 hours, then heated to 65 C. The reaction was concentrated, taken up in EtOAc and washed five times with brine, filtered through cotton, dried (Na2SO4), filtered, and concentrated. The resulting brown oil was purified by flash column chromatography (Silica gel, 0-60% EtOAc/Heptane). The product fractions were concentrated to yield the title compound.

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; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 360-97-4,Some common heterocyclic compound, 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, molecular formula is C4H6N4O, 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.

A mixture of 0.252 g 5-amino-1H-imidazole-4-carboxamide(Acros Organics, 2 mmol) and 0.764 g 3Me-STB(2 mmol) in 10 cm3 MeOH was heated to reflux for 3 h.The reaction mixture was left at room temperature (24 h)and filtered. The formed solid was crystallized from 5 cm3MeOH to give 0.37 g (69 %) light brown crystals of 3a.M.p.: [410 C; 1H NMR (500 MHz, DMSO-d6):d = 10.43 (s, 1H, NH), 10.19 (s, 1H, C(20)-OH), 10.16(s, 1H, C(40)-OH), 8.26 (s, 1H, C(2)-H), 7.37 (s, 1H,C(60)-H), 6.43 (d, J = 8.90 Hz, 1H, C(50)-H), 2.03 (s, 3H,CH3) ppm; 13C NMR (125 MHz, DMSO-d6): d = 161.7,158.6, 154.7, 136.9. 134.9, 133.4, 126.1, 122.6, 111.2,110.1, 107.4, 8.0 ppm; MS (70 eV): m/z (%) = 275 (M?,100), 274 (5), 259 (5), 192 (20), 167 (26), 151 (25), 110(5), 68 (16).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1H-imidazole-5-carboxamide, its application will become more common.

Reference:
Article; Matysiak, Joanna; Skrzypek, Alicja; Niewiadomy, Andrzej; Juszczak, Malgorzata; Langner, Ewa; Lemieszek, Marta; Rzeski, Wojciech; Karpiska, Monika M.; Walczak, Katarzyna; Monatshefte fur Chemie; vol. 146; 8; (2015); p. 1315 – 1327;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 705-09-9, A common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

A mixture of 2-difluoromethyl-lH-benzimidazole (0.168 g), 4,6-dichloro- 2-morpholinopyrimidine (0.233 g), sodium bicarbonate (0.168 g) and DMA (5 ml) was stirred under nitrogen and heated to 90C for 20 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1 : 1 mixture of isohexane and diethyl ether. There was thus obtained 6-chloro-4-(2-difluoromethylbenzimidazol- 1 -yl)-2-morpholinopyrimidine (0.075 g); NMR Spectrum: (DMSOd6) 3.7 (m, 4eta), 3.78 (m, 4H), 7.2 (s, IH), 7.39-7.72 (m, 3H), 7.84 (d, IH), 7.9 (d, IH); Mass Spectrum: M+H+ 366.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; HILL, George, Beresford; PASS, Martin; WO2008/32089; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 401567-00-8,Some common heterocyclic compound, 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, molecular formula is C8H4ClN3, 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.

A mixture of 2-chloro-1H-benzimidazole~5-carbonitrile (3.0 g, 17 mmol, 1.0 eq), (2S)-2-[(4-tert-0 butylphenoxy)methyl]oxirane (1-2) (3.5 g, 19 mmol, 1.1 eq) and cesium carbonate (0.10 g, 0,31 mmol, 0.020 eq) were heated under microwave irradiation at 130 C for 45 minutes. Ethyl acetate was added (200 ml) and the organic layer was washed with water (50 ml) and dried over sodium sulfate. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) followed by purification by super critical fluid chromatography (ChiraiPak AS-5 H, 21x250mm, 90/10 CO2/Methanol, 70 ml/min) to separate regioisomers and yield (2S)-2- ( { [tert-butyl(dimethyl )si Iy I ]oxy } methy l)-2 , 3 -dihydro [1,3] oxazolo [3 ,2 -a] benzi midazole-7 – carbonitrile (1-3) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.80 (s, 1H), 7.42 (d, 1H, J = 8.2 Hz), 7.19 (d, 1H, J = 8.2 Hz), 5.51-5.44 (m, 1H), 4.35-4.26 (m, 2H), 4.10 (dd, 1H, J – 1 1.8, 3.8 Hz), 3.95 (d, 1H, J – 3.1 Hz), 0.76 (s, 9 H), 0.00 (s, 6 H). LRMS m/z (M+H) 330.0 found,0 330.2 required. The alternative regioisomer (1-4) was also isolated and characterized.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2009/140163; (2009); A1;,
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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., SDS of cas: 68282-53-1

4-[(3-Carbamoylphenyl)(piperidin-4-yliden e)methyl]-N, N-dimethylbenzamide (40 mg, 11 mmcl) and4-methyl-IH-imidazole-5-carbaldehyde (13.3 mg, 0.12 mmol) were dissolved in dichloroethane (1.5mL). Acetic acid (6.3 pL, 0.11 mmol) was added and the reaction was stirred for 10 minutes at room temperature before NaBH(OAc)3 (37.3 mg, 0.18 mmcl) was added. The reaction mixture was stirred at room temperature for 2 days. Methylene chloride (1 mL) was added and the mixture was washed with water (1 mL). The water phase was extracted with methylene chloride (1 mL x 3). The combined organic phases were dried with Na2SO4, filtered and evaporated. The crude product waspurified by preparative HPLC (10 to 50% CH3CN in 50 mM NH4HCOS(aq)) to give the title compound (14 mg, 28% yield) as a white solid. MS ESI m/z 458 [M+H].

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; PHARMNOVO AB; VON MENTZER, Bengt; STARKE, Ingemar; BRANDT, Peter; (20 pag.)WO2016/99393; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 934-22-5, A common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

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:
Article; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13435-22-8,Some common heterocyclic compound, 13435-22-8, name is 1-Butyl-2-methyl-1H-imidazole, molecular formula is C8H14N2, 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.

Ex is of a 1-butyl-2-methyl-3(propyl-3-sulfonyl) imidazolium 1-Butyl-2-methylimidazol (710 mg, 0.9 mmol, 1 equivalent) was dissolved in 10 ml toluene and propanesultone (610 mg, 0.9 mmol, 1 equivalent) was added. The clear solution was heated at reflux temperature for 3h at which time a some withe precipitate was formed. The reaction mixture was cooled to room temperature and the white suspension was then filtered and washed with 5 ml toluene. The white solid was dried under high vacuum at 60C for 4 h, yielding the desired product (89 mg, 38% yield). H NMR analysis confirms the structure and a purity of >98 %. Melting point by DSC: 160 C.

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

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