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Chemical Structure| 53484-16-5 Chemical Structure| 53484-16-5

Structure of 53484-16-5

Chemical Structure| 53484-16-5

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Product Details of [ 53484-16-5 ]

CAS No. :53484-16-5
Formula : C8H7BrN2
M.W : 211.06
SMILES Code : CN1C=NC2=CC=C(Br)C=C12
MDL No. :MFCD09027271
InChI Key :QDXJAGXUNYFXRG-UHFFFAOYSA-N
Pubchem ID :23537644

Safety of [ 53484-16-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Application In Synthesis of [ 53484-16-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 53484-16-5 ]

[ 53484-16-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 337915-79-4 ]
  • [ 149-73-5 ]
  • [ 53484-16-5 ]
YieldReaction ConditionsOperation in experiment
54.74% With toluene-4-sulfonic acid; In toluene; for 2h;Heating / reflux; To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCI2.2H2O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and 1N NaOH (100ml). After extraction with CH2CI2, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2/MeOH (95/5). The title compound was obtained as a cream powder (2.5g, 54.74%); m.p. 126-128C.
54.74% With toluene-4-sulfonic acid; In toluene; for 2h;Heating / reflux; To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCl2.2H2O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and NaOH 1N (100ml). After extraction with CH2CI2, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2/MeOH (95/5). The title compoundwas obtained as a cream powder (2.5g, 54.74%); m.p. 126-128C
With toluene-4-sulfonic acid; at 100℃; for 4h; [00320] To a solution of 5-bromo-Nl-methylbenzene-l,2-diamine (7.4 g, 37 mmol) in trimethyl orthoformate (100 mL) was added p-toluenesulfonic acid (0.36g, 1.9 mmol). The reaction mixture was heated at 100 C for 4 h, cooled, concentrated, dissolved in ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The crude product was used in next step without further purification. (7.3 g, yield 93%) MS (ESI+) e/z: 212.1.
With toluene-4-sulfonic acid; at 100℃; for 4h; To a solution of <strong>[337915-79-4]5-bromo-N1-methylbenzene-1,2-diamine</strong> (7.4 g, 37 mmol) in HC(OMe)3 (100 mL) was added TsOH (0.36 g, 1.9 mmol). The reaction mixture was heated at 100 C for 4 h and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with brine, dried over Na2SO4, and concentrated. The crude product was used in next step without further purification (7.3 g, 93%). LCMS (mlz): 212.1 (M+ 1).

  • 2
  • [ 302800-13-1 ]
  • [ 149-73-5 ]
  • [ 53484-16-5 ]
YieldReaction ConditionsOperation in experiment
44% Step 3: 6-Bromo-l-methyl-117-benzoimidazole; [0311] To a suspension of (5-bromo-2-nitro-phenyl)-methyl-amine (1.2 g, 5.19 mmol) in ethanol (25 mL) was added tin(II) chloride (1.97 g, 10.39 mmol). The reaction mixture was stirred at 8O0C for 4h, then it was concentrated in vacuo. To the residue was added toluene (12 mL), trimethyl orthoformate (0.625 mL, 5.71 mmol), and para-toluenesulfonic acid (49 mg, 0.26 mmol). The reaction mixture was stirred at HO0C for 15h, then it was concentrated in vacuo and the residue was adsorbed on silica gel. Purification by flash chromatography on silica gel using a gradient of 0-8% methanol/dichloromethane afforded 482 mg of 6- bromo-1 -methyl- l//-benzoimidazole as a dark orange solid (44% yield): 1H NMR (DMSO- EPO <DP n="84"/>d6) δ 3.83 (s, 3H), 7.33 (dd, IH), 7.59 (d, IH), 7.86 (d, IH), 8.21 (s, IH); MS (m/z) 211, 213 [M+H+]+.
  • 4
  • [ 64-18-6 ]
  • [ 302800-13-1 ]
  • [ 53484-16-5 ]
YieldReaction ConditionsOperation in experiment
98% With iron; ammonium chloride; In isopropyl alcohol; for 24h;Reflux; [0444j Step B: Preparation of 6-bromo-1-methyl-benzimidazole: A mixture of 5- bromo-N-methyl-2-nitro-aniline (6.0 g, 26 mmol), iron powder (14.5 g, 260 mmol), ammonium chloride (13.9 g, 260 mmol) and formic acid (49.0 mL, 1298 mmol) in 2- propanol (75 mL) was stirred under reflux for 24 hours. After cooling to ambient temperature, ethyl acetate (50 mL) was added. The solid was removed by filtering through a pad of celite. The filtrate was concentrated. Saturated sodium bicarbonate (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by flash chromatography on silica gel 10:1 ethyl acetate/MeOH to give 6-bromo-1-methyl-benzimidazole (5.35 g, 98%) as solid.
  • 5
  • [ 53484-16-5 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; copper(l) chloride; at 100℃; for 5h;Sealed tube; [0003901 To a stirred solution of compound 1 (0.2 g, 1 eq) in aq. ammonia solution (2 mL), copper chloride (catalytic amount) was added and heated at 100 °C for 5 h in a sealed tube. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20percent methanol in dichloromethane and filtered. The filtrate was concentrated under reduced pressure to afford title compound 2. LCMS (mlz): 148.00 (M + 1).
 

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