Month: February 2021

Related Products of 930-62-1, The chemical industry reduces the impact on the environment during synthesis 930-62-1, name is 2,4-Dimethylimidazole, I believe this compound will play a more active role in future production and life.

Intermediate 18: step a 1-(2,4-Dimethyl-imidazol-1-yl)-ethanone The title compound was prepared according to the procedure described in J. Org. Chem. 1983, 48, 897: To a solution of 2,4-dimethylimidazole (4.00 g, 41.6 mmol) in toluene/chloroform (1/1, v/v, 50 mL) at room temperature was added acetyl chloride (1.48 mL, 20.8 mmol) dropwise over several minutes. The reaction was stirred at room temperature for 2 hours and filtered. The filtrate was evaporated, ethyl acetate was added and the solution was filtered again. The filtrate was evaporated to give the title compound.

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, 2,4-Dimethylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JACKSON, Paul Francis; Manthey, Carl; Rhodes, Kenneth; Scannevin, Robert; Leonard, Kristi Anne; Barbay, Joseph Kent; Todd, Matthew; Springer, Barry A.; US2012/302573; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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 mixture of imidazole (1 mmol), phenylboronic acid (2 mmol), K2CO3 (2 mmol), Cu(CH3COO)2H2O (1 mol %, 1.99 mg) and L1 (1 mol %, 5.7 mg) in ethanol (5 mL) was stirred at room temperature in a 50 mL oven dried round bottomed flask. After the completion of the reaction (as monitored by TLC), conventional workup of the reaction mixture was done with ethyl acetate (3 ¡Á 15 mL) and water (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered and the solvent was evaporated in a rotary evaporator under reduced pressure to get the crude product. The crude product was purified by column chromatography on silica gel (DCM: Methanol = 9:1) to afford the pure product.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baruah, Jayantajit; Gogoi, Kongkona; Dewan, Anindita; Borah, Geetika; Bora, Utpal; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1203 – 1208;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 40197-20-4, name is 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid, 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. name: 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid

[0055] N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg),and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight.A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring atroom temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure.The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. Themixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collectedby filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

The synthetic route of 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; (29 pag.)EP3231424; (2017); 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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., Recommanded Product: (1-Methyl-1H-imidazol-5-yl)methanol

General procedure: The reaction was performed in 2 batches. In a sealed tube, cyanomethylenetributyl phosphorane (9.28 mL, 35.40 mmol) was added to a solution of 3-methyl-5-nitro-lH- pyrazole (1.50 g, 1 1.80 mmol) and 3-hydroxymethyl-3-methyloxethane (3.53 mL, 35.40 mmol) in toluene (100 mL). The solution was heated at 60 ¡ãC for 18 h. The 2 batches were combined and the solvent was evaporated in vacuo. The residue (black oil) was purified by column chromatography on silica gel (irregular SiOH, 15-40 muiotaeta, 330 g, liquid loading on DCM, mobile phase: heptane/EtOAc, gradient from 90: 10 to 50:50). The fractions containing the product were combined and evaporated to dryness to give 3.95 g of intermediate 303 (79percent yield, orange oil) directly used as it in the next step.

The synthetic route of 38993-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 40644-16-4,Some common heterocyclic compound, 40644-16-4, name is 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5BrN2O, 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.

Step 3: 4-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol- 2-one To a solution of 4-bromo-1 ,3-dihydro-benzoimidazol-2-one (701 mg, 3.29 mmol) in dimethyl sulfoxide (2 ml_) was added potassium acetate (803 g, 10.9 mmol), 1,1′-bis(diphenyl phosphino) ferrocene palladium chloride (PdCI2 (dppf)) (134 mg, 0.16 mmol) and bis(pinacolato) diboron (1.67 g, 6.58 mmol). The mixture was degassed and heated in a microwave oven for 30 minutes at 150 0C. The solvent was filtered through a pad of celite, water (60 ml_) was added and the product was extracted with EtOAc (3 x, 30 ml_). The combined organic extracts were dried over Na2SO4 (sodium sulfate), and the solvent removed to provide crude 4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol-2-one which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; WYETH; WO2009/111260; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 17289-19-9, These common heterocyclic compound, 17289-19-9, name is Methyl 1-methyl-1H-imidazole-4-carboxylate, 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 solution of methyl 1 -methyl-1 H-imidazole-4-carboxylate (14.3 mmol, 2 g) in CCI4 (40 ml_), NBS (15.3 mmol, 2.72 g) and AIBN (0.715 mmol, 1 17 mg) were added. The reaction mixture was stirred 4h at 605C and then cooled to room temperature. The solvent was evaporated. The reaction crude was purified by flash chromatography on silica gel using an elution of 8% methanol in ethyl acetate to afford methyl 2-bromo-1 -methyl-1 H-imidazole-4-carboxylate (529 mg, Yield: 17%). 1 H NMR (400 MHz, CDCI3) delta 7.59 (1 H, s), 3.91 (3H, s), 3.67 (3H, s) LC-MS: tR = 1 .60 [M+H] + = 219/221 (method 3)

The synthetic route of 17289-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; DRACONIS PHARMA, S.L.; LABORATORIOS DEL DR. ESTEVE, S.A.; AGUILAR, Nuria; FERNANDEZ, Joan, Carles; TERRICABRAS, Emma; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/149997; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

16042-25-4, name is 2-Imidazolecarboxylic acid, 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 2-Imidazolecarboxylic acid

) A/-(3,5-Difluorophenyl)-1 H-imidazole-2-carboxamideTo a solution of 1 /-/-imidazole-2-carboxylic acid (2.50 g, 22.3 mmol) in DMF (30 mL) were added 3,5-difluoroaniline (2.23 mL, 22.3 mmol), EDC-HCI (6.41 g, 33.46 mmol) and HOBt (4.52 g, 33.46 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuum and the crude was dissolved in dichloromethane. The solution was washed with a diluted aqueous solution of potassium carbonate, dried over sodium sulphate, filtered and concentrated. 2.75 g (55% yield) of the title compound were obtained as a solid.LRMS (m/z): 224 (M+1 )

The synthetic route of 16042-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 35203-44-2,Some common heterocyclic compound, 35203-44-2, name is 1-Propyl-1H-imidazole, molecular formula is C6H10N2, 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 100-mL two-neck flask was placed, N-propylimidazole (2.10 g, 18.0 mmol) and 35 mL of toluene were added, and 3-bromopropyldiethoxyphosphine oxide (5.18 g, 20.0 mmol) was added dropwise with heating and stirring.And reacted at 85 ¡ãC for 6 h and cooled to room temperature. Pour out the upper toluene,100 mL of deionized water was added to dissolve the product to obtain an aqueous phase. The aqueous phase was washed with an EtOAc_PE=3:1 organic phase (30 mL¡Á4) to separate the aqueous phase II; di(2-ethylhexyl) phosphate (P204). ) (5.80 g, 18.0 mmol) was refluxed under the action of sodium for 24 h. The resulting sodium salt was dissolved in methylene chloride and the separated aqueous phase was stirred at room temperature for 3 h.Add 50 mL of CH2Cl2 and stir to separate the organic phase. The organic phase was washed with deionized water (20 mL¡Á5) and the organic phase was obtained after liquid separation. The organic phase was dried by adding anhydrous Na 2 SO 4 , filtered, and most of the CH 2 Cl 2 was evaporated under reduced pressure and dried in vacuum at 70¡ã C. for 3 h. Yellow sticky liquid product 9.45g (yield 86percent),

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

Reference:
Patent; Ningbo University; Wang Junping; Liang Hongze; Feng Da; Zhao Jieying; Kang Xinchun; Zhang Xiaozhen; Shen Fei; Huang Feilong; (21 pag.)CN104945435; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 128293-62-9,Some common heterocyclic compound, 128293-62-9, name is Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, molecular formula is C7H11N3O2, 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 231: N-[2-(tert-butylcarbamoyl)-1-methyl-1H-imidazol-4-yl]-4,4-dimethyl- l-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide Step 1: Synthesis of ethyl 4-{[(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2- a]indol-7-yl)carbonyl]amino}-1-methyl-1H-imidazole-2-carboxylateTo a solution of 4,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7- carboxylic acid (336 mg, 1.3 mmol, Intermediate E) in DMF (1 mL) are added N- hydroxybenzotriazole (351 mg, 2.6 mmol) and l-ethyl-3-(3-dimethylaminopropyl) carbodiimide (498 mg, 2.6 mmol). After stirring for 10 min, 4-amino-1-methyl-lH- imidazole-2-carboxylic acid ethyl ester (535 mg, 2.6 mmol), N,N-diisopropylethylamine (0.45 mL, 2.6 mmol) and 4-dimethylaminopyridine (32 mg, 0.26 mmol) are added. The reaction mixture is heated at 60 C for 16 h. DMF is removed under a stream of N2 at 40 C and EtOAc (2 mL) and water (2 mL) are added. After stirring for 15min, a white solid is formed and it is filtered and dried to afford the title compound (490 mg, 92%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17464-88-9, 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. 17464-88-9 name is 1,3,4,6-Tetrakis(methoxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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.

60 g (0.188 mol) of tetramethoxymethylglycoluril (product name: POWDERLINK [registered trademark] 1174 commercially available from Japan Cytec Industries, hereinafter abbreviated as PL-LI in this specification), 1,200 g of propylene glycol monomethyl ether (hereinafter abbreviated as PGME in this specification), and 120 g of a washed ion-exchange resin for a catalyst (product name: AMBERLYST [registered trademark] 15JWET, commercially available from Dow Chemical Company, hereinafter abbreviated as 15JWET in this specification) were put into a 2,000 mL flask, and the mixture was stirred and dissolved at 25¡ã C. and then heated and stirred under a reduced pressure (80 Torr to 100 Torr) at 60¡ã C. for 7 hours. Then, the pressure inside the flask was recovered and cooling was performed to 25¡ã C., and then 15JWET was filtered off to obtain a desired compound (hereinafter abbreviated as PGME-PL in this specification). The obtained compound was identified by 1H NMR. As a result, it was confirmed that a peak (31.9 ppm) of a methoxy group of PL-LI disappeared and about 4 molecules of PGME were introduced into one molecule of PL-LI, and the glycoluril derivative of Formula (1A-1) (hereinafter abbreviated as PGME-PL in this specification) was obtained. [1.0 to 1.1 ppm (3H, ?CH3), 3.2 to 3.3 ppm (20H, ?OCH3 and ?CH2O?), 3.6 to 3.8 ppm (4H, ?OCH<)] At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3,4,6-Tetrakis(methoxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, and friends who are interested can also refer to it. Reference:
Patent; NISSAN CHEMICAL CORPORATION; SAKAIDA, Yasushi; TAKASE, Kenji; KISHIOKA, Takahiro; SAKAMOTO, Rikimaru; (14 pag.)US2019/163063; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem