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Chemical Structure| 59256-47-2 Chemical Structure| 59256-47-2

Structure of 59256-47-2

Chemical Structure| 59256-47-2

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Product Details of [ 59256-47-2 ]

CAS No. :59256-47-2
Formula : C10H8BrNO3
M.W : 270.08
SMILES Code : O=C(O)/C=C\C(NC1=CC=C(Br)C=C1)=O
MDL No. :MFCD00134952

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Application In Synthesis of [ 59256-47-2 ]

* 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 [ 59256-47-2 ]

[ 59256-47-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 59256-47-2 ]
  • [ 13380-67-1 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic anhydride; for 2h;Reflux; General procedure: The synthesis of maleimides 1-47 was performed by mixing an equimolar amount of the appropriate maleic anhydrides 68-72 in 5 mL of CHCl3 and anilines 73, 78-90, amines 91-94 or phenylalkylamines 74-77 (5 mmol) dissolved in 1 mL of CHCl3 and stirred during 1 h. The solid (maleamic acid) which precipitated out of the reaction mixture was filtered off. The whole amount of maleamic acid was dissolved in 5 mL of acetic anhydride and 100 mg of sodium acetate was added. The mixture was heated for 2 h under reflux. The reaction was cooled and quenched with water; then, the aqueous solution was extracted with Et2O, dried with Na2SO4, filtered, and the solvent was evaporated. The product was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (9:1) as eluent. Compounds 1-10, 16-26, 31-34, 36, 38-42 and 43-47 were previously reported.[3], [8], [21], [22], [23], [24], [25], [26], [27] and [28]
With sulfuric acid; acetic acid; at 60℃; for 0.75h; General procedure: Maleic anhydride (1.1 eq) was added at once with vigorous stirring in the solution of aniline (1.0 eq)in acetic acid (15 mL). It was stirred for another 10 minute while the reaction mixture turned into a suspension.To this reaction mixture concentrated sulphuric acid (2.0eq) was added at once while stirring. The temperature increased by 10oC and suspension turned into a clear solution. The temperature of reaction mixture was increased to 60oC and stirred furtherfor 45 minutes. It was allowed to come at room temperature and poured onto crushed ice. Thesolid separated was filtered and washed with water. The solid was transferred to the aqueous solution of sodium bicarbonate and stirred for 10 minutes to remove maleanilic acid if present. Then filtered and washed with water and recrystallized in ethanol. Yield: quantitative.
With sodium acetate; acetic anhydride; at 80℃; for 0.5h; General procedure: The maleamic acid was allowed to cyclodehydrated by using acetic anhydride and fused sodium acetate. The solution was stirred for 0.5 h at 80 C. The prepared produced is precipitated in ice, filtered and washed by water. The product was then crystallized by ethanol [6] (Fig. 1).
 

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