Tag: M.W=200-300

Related Products of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

Preparation of olmesartan medoxomil Example 1 17.3 g (124.8 mmol) of K2CO3, 15 g (62.4 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (III) and 38.3 g (68.7 mmol) 4-[2-(trityltetrazol-5-yl)phenyl]-benzyl bromide (IVa) were suspended in 750 ml of acetonitrile. The suspension was then heated under reflux until the reaction was completed (7 h). 510 ml of acetonitrile were distilled off and the concentrate was cooled to 23 to 25 C. The mixture was stirred at this temperature overnight, then the suspension was cooled to 0 C and stirred at this temperature for 1 h. The crude product (Va) was filtered off and washed 2x with 20 ml of cooled acetonitrile. Wet product was suspended in 450 ml of water, stirred for 1.5 h and after that filtered off. The mass of dried product (Va) was 39.5 g (89 %). T=165-169C IR: 1666, 1525, 1291, 1446, 1177, 881, 756, 699, 640

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KRKA, tovarna zdravil, d.d., Novo mesto; EP1816131; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 870837-18-6, name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Under ice-cooling, L-selectride (1.3 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (10 mi) solution containing (R)-6-[(S)-3,4-difluorophenyl]-l-metyltetrahydropyrrolo[2,1-c][1,4]oxazin-3,4-dione (297 mg). Stirring was continued for 1.5 hours at the same temperature. A 5 N sodium hydroxide solution (197 muL) was added to the reaction solution, and stirring was continued for 10 minutes at 0 C., and next hydrogen peroxide solution (96 muL, 35% solution) was added, and stirring was continued for 10 minutes at 0 C. Sodium bisulfite (103 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (10 mL) and triphenyl phosphonium bromide (345 mg) were added to the residue, and the resultant was heated under reflux for 2 hours. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzaldehyde (235 mg) and triethylamine (274 muL) were added, and the resultant was stirred at room temperature for 20 hours. The solvent was removed under a vacuum, and ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (carrier: Chromatrex NH and Chromatrex, eluting solvent: hexane/ethyl acetate?ethyl acetate?ethyl acetate/methanol), and the title compound (260 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 466 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.47 (d, J=6.8 Hz, 3H), 1.80-1.91 (m, 1H), 2.02-2.07 (m, 1H), 2.10-2.17 (m, 1H), 2.29 (s, 3H), 2.35-2.46 (m, 1H), 3.84 (s, 3H), 4.23-4.28 (m, 1H), 4.78-4.84 (m, 1H), 5.11 (d, J=9.6 Hz, 1H), 6.81 (s, 1H), 6.91 (dd, J=1.2, 1.2 Hz, 1H), 7.04-7.15 (m, 3H), 7.19 (d, J=8.0 Hz, 1H), 7.38-7.40 (m, 1H), 7.38 (s, 1H), 7.69 (d, J=1.2 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14813-85-5,Some common heterocyclic compound, 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C13H10N2O, 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-phenyl-1,3-dihydro-benzimidazole-2-one, and 52g (250 mmol), in the first and K2CO3 of 38g (275 mmol), is introduced into the DMF of 100ml. After 1 hour at room temperature, it is added dropwise a solution of 2-bromobenzyl bromide 62g in DMF in 500 ml (250 mmol). The reaction mixture was then stirred for 25 hours at room temperature. After this time, the reaction mixture was poured onto ice, and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4, and evaporated. The residue was extracted with hot toluene, recrystallized from toluene / n-heptane. The yield is 65g (70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; STOESSEL, PHILIPP; PARHAM, AMIR HOSSAIN; PFLUMM, CHRISTOF; JATSCH, ANJA; EBERLE, THOMAS; KROEBER, JONAS VALENTIN; (86 pag.)JP2016/500675; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 28890-99-5, The chemical industry reduces the impact on the environment during synthesis 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, I believe this compound will play a more active role in future production and life.

5.00 g ( 36.0 mmol) 2,3-difluorobenzonitrile, 14.9 g (72.0 mmol) 6H-benzimidazolo[1 ,2- a]benzimidazole and 30.5 (144 mmol) potassium phosphate tribasic in 120 ml NMP (N-Methyl- 2-pyrrolidon) are stirred at 185 C under nitrogen for 6 h. The reaction mixture is filtered hot and the organic phase is poured on water. The product is filtered of. Column chromatography on silica gel with chloroform gives 6.25 g 33.9 % of the product. 1H NMR (300 MHz, DMSO-D6): rotamers: delta 8.43-8.57 (m, 2H), 7.58-8.20 (m, 6H), 6.86-7.42 (m, 9H), 6.63-7.78 (m, 1 H), 6.48-6.54 (m, 1 H).

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, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; RAIMANN, Thomas; SCHAeFER, Thomas; SAITO, Masatoshi; WOLLEB, Heinz; BENEDITO, Flavio Luiz; NISHIMAE, Yuichi; NAKANO, Yuki; NAGASHIMA, Hideaki; (111 pag.)WO2016/157113; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 67085-11-4, A common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, molecular formula is C13H15ClN2O, 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.

PREPARATION 7 A mixture of 1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]imidazole (20 g) in dry pyridine (100 ml) was cooled in an ice bath and treated dropwise with stirring with 7.0 ml of methanesulfonyl chloride. The mixture was allowed to come to room temperature overnight and diluted to 500 ml by the addition of ethyl acetate, with stirring. The resulting solid was then filtered off, washed with acetone and dried in air to give 1-[4-(4-chlorophenyl)-2-(methanesulfonyloxy)-n-butyl]imidazole hydrochloride as a white solid (27.4 g).

The synthetic route of 67085-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Syntex (U.S.A.) Inc.; US4518607; (1985); A;,
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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 1-Decyl-1H-imidazole

Equipped with a stirrer, a thermometer, a three-necked flask was added 1.67 g (8.0 mmol) N- decyl-imidazole, 0.56 g (4.4 mmol) 1,3- dichloro-2-propanol, at 115 ~ 125 C The reaction was stirred after, TLC tracking progress of the reaction, the reaction of about 8 ~ 12 h, the crude product was mixed with chloroform and ethyl acetate solvent was recrystallized to give a white powdery solid 1,1′-didecyl-3,3 ‘- (2- hydroxy-1,3-propylene) imidazole hydrochloride 1.42 g, yield 65.2%.

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; Qiqihar university; Wang, LiYan; Deng, QiGang; Zheng, YongJie; Huo, shichao; Liu, Jia; Sun, zhu; (10 pag.)CN103951702; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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: 1450-93-7

EXAMPLE 2 5-(4-Pyridyl)imidazo[1,2-a]pyrimidine A mixture of 5.29 g of 2-aminoimidazole hemisulfate, 3.28 g of anhydrous sodium acetate and 7.04 g of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one (prepared according to the procedure of Example 63 in U.S. Pat. No. 4,281,000) in 100 ml of glacial acetic acid was heated under reflux for 16 hours. The procedure of the above Example 1 was followed and the title compound was obtained as pale yellow needles, mp 244-245 C.

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4551530; (1985); A;,
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. 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 53484-15-4

To a solution of 5-bromo-1-methyl-1H-benzo[d]imidazole (200 mg, 0.33 mmol, 1 eq.) in 1,4-dioxane (10 mL) was added 5-(4,4,5,5-bis(pinacolato)diboron (287 mg, 1.13 mmol, 1.2 eq.), KOAc (276 mg, 2.82 mmol, 2 eq.), PdCl2(dppf).DCM (76 mg, 0.09 mmol, 0.09 eq.). The reaction mixture was deoxygenated with N2 and the reaction mixture was stirred at 80 C. for 16 h. The reaction was monitored by LCMS and found to be complete after 18 h. The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with ethyl acetate (2*50 mL). Combined organic layer was washed with brine (20 mL) and dried over sodium sulfate. Removal of solvent under reduced pressure gave crude which was purified by Combi-Flash (0-100% EtOAC-Hexane) to afford the desired product (120 mg, 49%) as brown oil.

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 53484-15-4.

Reference:
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (314 pag.)US2019/23702; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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 14741-71-0, category: imidazoles-derivatives

General procedure: To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (30 mL) containing piperidine (0.50 mL) either benzaldehyde (1.06 g, 0.01 mol) or 4-methoxy benzaldehyde (1.31 g, 0.01 mol) or 4-chlorobenzaldehyde (1.34 g, 0.01 mol) was added. The reaction mixture, in each case, was heated under reflux for 3 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Ethyl 2-(1H-benzo[d]imidazol-2-yl)-3-phenylacrylate (7a). Gray crystals from ethanol; yield:2.45 g (77%); m.p. > 300 oC. IR, : 3478-3329 (NH), 3057 (CH aromatic), 2962, 2873 (CH3,CH2), 1688 (C=O), 1646 (C=N), 1630 (C=C). 1H-NMR: : 1.14 (t, 3H, J = 7.66 Hz, CH3), 4.21(q, 2H, J = 7.66 Hz, CH2), 6.24 (s, 1H, CH=C), 7.29-7.38 (m, 9H, C6H5, C6H4), 8.26 (s, 1H, NH,D2O exchangeable). 13C NMR (DMSO): 16.3 (ester CH3), 52.5 (ester CH2), 89.3, 90.2 (CH=C),120.6, 122.1, 123.2, 123.9, 124.1, 124.6, 125.8, 126.2, 127.8, 128.2, (C6H5, C6H4), 164.8 (CO),172.6 (C=N); Anal. calcd for C18H16N2O2: C, 73.95; H, 5.52; N, 9.58%. Found: C, 72.73; H,5.49; N, 9.37%. MS: m/z: (%) 292 (M+, 64%).

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, Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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 1450-93-7, name: 1H-imidazol-2-amine sulfate(2:1)

EXAMPLE 13 7-Methyl-5-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine A mixture of 5.14 g of (3-dimethylamino)-1[3-(trifluoromethyl)phenyl]-2-butene-1-one, 1.64 g of anhydrous sodium acetate and 2.64 g of 2-aminoimidazole hemisulfate in 100 ml of glacial acetic acid was refluxed for six hours. The solvent was removed in vacuo and the solid residue was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was separated and dried over powdered anhydrous sodium sulfate, then passed through a short column of a hydrous magnesium silicate. The effluent was refluxed on a steam bath with the gradual addition of hexane until crystallization was noted. On cooling the product was separated and collected by filtration and gave 2.55 g of the desired compound as off-white crystals, m.p. 170-172 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-imidazol-2-amine sulfate(2:1), and friends who are interested can also refer to it.

Reference:
Patent; American Cyanamid Company; US5037980; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem