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Chemical Structure| 57547-55-4 Chemical Structure| 57547-55-4

Structure of 57547-55-4

Chemical Structure| 57547-55-4

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Product Details of [ 57547-55-4 ]

CAS No. :57547-55-4
Formula : C5H3ClO3
M.W : 146.53
SMILES Code : O=C(O1)C(C)=C(Cl)C1=O
MDL No. :MFCD23160730

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Application In Synthesis of [ 57547-55-4 ]

* 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 [ 57547-55-4 ]

[ 57547-55-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6154-04-7 ]
  • [ 57547-55-4 ]
  • 3-chloro-4-methyl-1-(1-methyl-1H-1,2,4,5-tetrazol-3-yl)-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With acetic acid; for 2h;Reflux; 3-Chloro-4-methylfuran-2,5-dione (500 mg, 3.41 mmol, 1.00 equiv) and <strong>[6154-04-7]1-methyl-1H-1,2,4,5-tetrazole-3-amine</strong> (338 mg, 3.41 mmol, 1.00 equiv) were dissolved in conc. acetic acid (5 ml) and stirred under reflux conditions for 2 hours. After cooling to room temperature, water and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 3-chloro-4-methyl-1-(1-methyl-1H-1,2,4,5-tetrazol-3-yl)-1H-pyrrole-2,5-dione in the form of a colorless solid (487 mg, 62% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 4.42 (s, 3H), 2.20 (s, 3H).3-Chloro-4-methyl-1-(1-methyl-1H-1,2,4,5-tetrazol-3-yl)-1H-pyrrole-2,5-dione (420 mg, 1.85 mmol, 1.0 equiv) was dissolved in a mixture of tetrahydrofuran and methanol (5 ml, ratio 1:1) and cooled to a temperature of -30 C., and sodium borohydride (70 mg, 1.85 mmol, 1.0 equiv) was added. The resulting reaction mixture was stirred at -30 C. for 1 h and then slowly warmed to room temperature. After the reaction had ended, acetic acid was added carefully to adjust the pH to 4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over sodium sulfate, filtered and concentrated. By final purification by column chromatography (gradient ethyl acetate/heptane) of the resulting crude product, it was possible to separate 3-chloro-5-hydroxy-4-methyl-1-(1-methyl-1H-1,2,4,5-tetrazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one from the isomeric 4-chloro-5-hydroxy-3-methyl-1-(1-methyl-1H-1,2,4,5-tetrazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one (1.84-2) also obtained and to isolate the compound in the form of a colorless solid (218 mg, 51% of theory). 1H-NMR (600 MHz, CDCl3 delta, ppm) 7.18 (d, 1H), 6.03 (d, 1H), 4.34 (s, 3H), 2.08 (s, 3H); 13C-NMR (150 MHz, CDCl3 delta, ppm) 161.5; 157.8; 153.2; 122.4; 82.9; 40.1; 11.8.
  • 2
  • [ 57547-55-4 ]
  • [ 49607-51-4 ]
  • 3-chloro-4-methyl-1-(1-methyl-1H-1,2,4-triazol-3-yl)-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% With toluene-4-sulfonic acid; In toluene; at 100℃; for 0.5h;Microwave irradiation; 3-Chloro-4-methylfuran-2,5-dione (625 mg, 4.27 mmol, 1.00 equiv) and <strong>[49607-51-4]1-methyl-1H-1,2,4-triazole-3-amine</strong> (419 mg, 4.15 mmol, 1.00 equiv) were dissolved in toluene (10 ml), 4-toluenesulfonic acid monohydrate (12 mg, 0.06 mmol, 0.02 equiv.) was added and the mixture was stirred under microwave conditions at a temperature of 100 C. for 30 minutes. After cooling to room temperature, water and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 3-chloro-4-methyl-1-(1-methyl-1H-1,2,4-triazol-3-yl)-1H-pyrrole-2,5-dione in the form of a colorless solid (110 mg, 11% of theory). 1H-NMR (400 MHz, d6-DMSO delta, ppm) 8.13 (s, 1H), 3.80 (s, 3H), 2.09 (s, 3H).
 

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