Category: 5955-72-6

Electric Literature of 5955-72-6, 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. 5955-72-6 name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-6-nitro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); 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. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4ClN3O2

Methanamine (2M in THF, 15 mL) was added to a sealable tube containing 2-chloro-5-nitro- 1 H-benzo[d]imidazole (1 g). The reaction flask was sealed and stirred at 80 C for 16 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was washed with diethyl ether (15 mL) and dried in vacuo to afford the crude title product as a black tar (600 mg), which was used directly without purification. LCMS m/z 193.06 (M+H)+.

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 5955-72-6.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (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. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-6-nitro-1H-benzo[d]imidazole

Dimethylamine (2M in THF, 15 ml_) was added to a sealable tube containing 2-chloro-5- nitro-1 H-benzo[d]imidazole (1 g, Example 181 (a)). The reaction flask was sealed and heated at 80 C for 16 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to afford the crude title product as a black tar (800 mg). This was used directly without purification. LCMS m/z 207.16 (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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5955-72-6, A common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, molecular formula is C7H4ClN3O2, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil. Step 4. To a solution of methyl glycolate in dry THF (8 ml) cooled at 0 C was added NaH (60%) in mineral oil. The reaction was stirred at room temperature for 2h. The suspension was cooled at 0 C and a solution of A/1482/82/1 was added dropwise. The reaction mixture was stirred at room temperature for 16h. UPLC showed ~70% reaction completion, and another 1.1 eq of NaH was added. After stirring for 16h, UPLC showed formation of side products. The reaction was stopped, and S. NH4C1 and EtOAC were added. The organic phase was separated, dried and evaporated to give a crude product, which was then purified by silica column (CyHex to CyHex: EtOAc= 85:15). The product named A/1482/83/1 was recovered with a 50% of purity grade (by NMR), with the UPLC retention time of the impurity that same as that of the desired product. Step 5. To a stirred solution oh the A/1482/83/1 cooled to 0 C in THF, a solution of LiOH in water was added dropwise. The mixture was then stirred at room temperature for 2h. UPLC showed complete conversion. The solvent was evaporated under vacuum. The residue was portioned between water and EtOAc, the organic phase was separated and discarded. The water phase was evaporated to give the desired product as the corresponding lithium salt A/1482/84/1. Step 6. To a stirred solution of A/1482/84/1, 4-aminobenzonitrile and TEA in THF 3: 1, HATU was added at room temperature. After stirring for 5h, UPLC showed complete conversion. The solvent was evaporated and the residue partitioned between saturated aqueous NaHC03 and DCM. The organic phase was separated, dried and the solvent evaporated to give an impure product, which was further purified by Si02 column (DCM to DCM:MeOH). The desired product named A/1540/23/1 was recovered as a white solid.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5955-72-6, These common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, 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.

[0635] A mixture of 2-chloro-5-nitro-benzimidazole (985 mg, 5.0 mmole) and 1-(3-aminopropyl)-imidazole (1.8 mL, 3 eq) in toluene (15 mL) was heated at reflux for 5 hr. The reaction was partitioned between EtOAc and brine to give a precipitate that was collected by filtration. Flash chromatography of this material (silica gel; stepwise gradient elution with mixtures of DCM containing 1, 2, 3, . . . 10% MeOH) afforded 2-[3-[imidazo-1-yl]-propylamino]-5-nitro-benzimidazole (550 mg) as a solid. This material was combined with 10% Pd on charcoal (500 mg), suspended in EtOH, and stirred under a hydrogen atmosphere (balloon) overnight. Removal of the catalyst by filtration and the solvent under reduced pressure left the crude 5-amino-2-[3-imidazo-1-ylpropylamino]-benzimidazole as a solid. A portion of this material (77 mg, 0.30 mmole) was added to a mixture of 319A (99 mg, 1.0 eq), an aqueous solution of HCl (0.60 mL, 1.0 M, 2 eq) and n-BuOH (1.5 mL). This was heated in a sealed vial at 120 C. for 20 hr. After cooling to RT, 572 (HPLC retention time (YMC ODS S7 3×50 mm): 1.20 min) was isolated by preparative HPLC.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5955-72-6, A common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, molecular formula is C7H4ClN3O2, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil. Step 4. To a solution of methyl glycolate in dry THF (8 ml) cooled at 0 C was added NaH (60%) in mineral oil. The reaction was stirred at room temperature for 2h. The suspension was cooled at 0 C and a solution of A/1482/82/1 was added dropwise. The reaction mixture was stirred at room temperature for 16h. UPLC showed ~70% reaction completion, and another 1.1 eq of NaH was added. After stirring for 16h, UPLC showed formation of side products. The reaction was stopped, and S. NH4C1 and EtOAC were added. The organic phase was separated, dried and evaporated to give a crude product, which was then purified by silica column (CyHex to CyHex: EtOAc= 85:15). The product named A/1482/83/1 was recovered with a 50% of purity grade (by NMR), with the UPLC retention time of the impurity that same as that of the desired product.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5955-72-6, A common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, molecular formula is C7H4ClN3O2, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil. Step 4. To a solution of methyl glycolate in dry THF (8 ml) cooled at 0 C was added NaH (60%) in mineral oil. The reaction was stirred at room temperature for 2h. The suspension was cooled at 0 C and a solution of A/1482/82/1 was added dropwise. The reaction mixture was stirred at room temperature for 16h. UPLC showed ~70% reaction completion, and another 1.1 eq of NaH was added. After stirring for 16h, UPLC showed formation of side products. The reaction was stopped, and S. NH4C1 and EtOAC were added. The organic phase was separated, dried and evaporated to give a crude product, which was then purified by silica column (CyHex to CyHex: EtOAc= 85:15). The product named A/1482/83/1 was recovered with a 50% of purity grade (by NMR), with the UPLC retention time of the impurity that same as that of the desired product. Step 5. To a stirred solution oh the A/1482/83/1 cooled to 0 C in THF, a solution of LiOH in water was added dropwise. The mixture was then stirred at room temperature for 2h. UPLC showed complete conversion. The solvent was evaporated under vacuum. The residue was portioned between water and EtOAc, the organic phase was separated and discarded. The water phase was evaporated to give the desired product as the corresponding lithium salt A/1482/84/1.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H4ClN3O2

PROCEDURE: 2-chloro-5-nitro-1H-benzo[d]imidazole (200 mg, 1.012 mmol) is slurried with ethanol (6 mL), water (2 mL), and dimethylformamide (0.5 mL). Iron (283 mg, 5.06 mmol), and ammoniumchloride (271 mg, 5.06 mmol) were added and the reaction mixture was heated to reflux for 30 mm. The crude mixture was filtered and the resulting filtrate was concentrated and compound was purified by flash column chromatography (2% CH3OH/CH2C12) afforded the title compound 2-chloro-1H-benzo[d]imidazol-5-amine (150 mg, 0.877 mmol, 87 % yield) as a solid. Proton nuclear magnetic resonance (?1HNMR?) (400 MHz, DMSO-d6): oe 7.14 (d, 1H, J = 8.4 Hz), 6.56 (s, 1H), 6.49 (d, 1H, J = 8.8 Hz), 4.92 (bs, 2H).

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF UTAH; VANKAYALAPATI, Hairprasad; SHARMA, Sunil; SORNA, Venkataswamy; WO2015/31564; (2015); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]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 5955-72-6, 5955-72-6

To a suspension of 3.952 g (20 mmole) of 19 in 100 mL of 1,2-dichloroethane, was added 5 mL (20 mmole) of BSA. The reaction mixture was stirred at 75 C. for 15 min to give a clear solution. This solution was cooled to ~ 20 C. and treated with 7.0 g (22 mmole) of 1,2,3,5-tetra-O-acetyl-b-D-ribofuranose and 4.638 mL (24 mmole) of TMSOTf at room temperature for 2 h. The reaction mixture was diluted with 200 mL of CHCl3. The CHCl3 solution was washed with sat. NaHCO3 solution (200 mL*2), sat. NaCl solution (200 mL), dried (Na2 SO4), and evaporated. The residue was chromatographed on a silica column (5*35 cm, eluted with CHCl3 and 0.5% MeOH/CHCl3). Evaporation of the appropriate fractions gave 6.50 g (71% one spot on TLC) of 74 and 75 as a white foam. Fractional recrystallization of this foam (5 times from MeOH) give 1.59 g (17%) of the pure 6-nitro isomer 75. MP 127-129 C. MS (EI) m/e 455.0750 (2%, M+ =455.0732). 1 H NMR (DMSO-d6): d 8.68 (d, 1, 7-H, J7-5 =2.0 Hz), 8.21 (dd, 1, 5-H, J5-4 =9.0 Hz), 7.88 (d, 1, 4-H), 6.41 (d, 1, 1′-H, J1′-2′ =7.0 Hz), 5.58 (t, 1, 2′-H, J2′-3′ =7.0 Hz), 5.45 (dd, 1, 3′-H, J3′-4′ =4.0 Hz), 4.50, 4.40 (2*m, 3, 4′-H and 5′-H), 2.15, 2.12, 2.03 (3*s,9, 3*Ac). 13 C NMR (DMSO-d6): d 170.12, 169.49, 169.25 (3*OCOCH3), 145.60 (C3a), 143.96 (C2), 143.65 (C6), 132.46 (C7a), 119.65 (C4), 118.92 (C5), 108.47 (C7), 86.96 (C1′), 79.67 (C4′). 71.12 (C2′), 68.75 (C3′), 62.56 (C5′), 20.39, 20.31, 20.03 (3*OCOCH3).

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-Chloro-6-nitro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Regents of the University of Michigan; US5574058; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem