Acetic Anhydride → HCID 19733881, compound

HRID 2073339Notes

Reaction equation

HRID 2073339 reaction equation
[C:1]1([NH:7][C:8](=[O:14])/[CH:9]=[CH:10]\[C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](OC(=O)C)(=O)[CH3:16].C(N(CC)CC)C>CC(C)=O.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[CH:15]1[C:4]2[CH:3]=[CH:2][C:1]([N:7]3[C:8](=[O:14])[CH:9]=[CH:10][C:11]3=[O:12])=[CH:6][C:5]=2[CH:16]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1550938Maleic acid anilide

Product 1

HCID 19733881HCID 19733881, compound

Reagents, catalysts & solvents 2

HCID 62601Nickel acetate tetrahydrateCatalystHCID 180AcetoneSolvent

Procedure

N-phenyl-maleamic acid (6.00 g, 27.62 mmol) was partially dissolved in about 100 ml of acetone in a 250 ml round-bottomed flask. To this stirred heterogeneous mixture was added solid nickel acetate tetrahydrate (0.25 g), followed by the mixture of acetic anhydride (6.27 g. 61.42 mmol) and triethylamine (1.82 g, 23.0 mmol). Gradually, almost all the solids dissolved and the resultant reaction mixture was stirred at room temperature for two days. After all the solvent had been removed by rotary evaporation, the residual oil (smell of acetic acid) was mixed with a small amount of methylene chloride. The solution was passed through a small column containing silica gel saturated with hexane. The column was eluted with hexane until the yellow band developed reached its bottom. Then, it was eluted with methylene chloride. The second yellow fraction collected was then subjected to rotary evaporation and hexane was then added slowly to the concentrated solution to precipitate the product as a yellow solid. The product was collected, washed with hexane and air-dried overnight. Yield: 4.34 g (78.9%). Anal Calc. for C12H9NO2 : C, 72.35; H, 4.55; N, 7.03. Found: C, 71.84; H, 4.54; N, 6.90. Mass Spectroscopy: M+ , 199 (100%). Proton NMR (CDCl3),δ(ppm): 3.23 (singlet, 4H, alicyclic protons); 6.87 (singlet, 2H, olefinic protons); 7.03-7.33 (complex, 3H, aromatic protons). IR (KBr): ν(maleimide): 1710 cm-1, vs; 1772 cm-1, W.

Workup

  1. dissolutionGradually, almost all the solids dissolved
  2. customthe resultant reaction mixture
  3. customAfter all the solvent had been removed by rotary evaporation
  4. additionthe residual oil (smell of acetic acid) was mixed with a small amount of methylene chloride
  5. additioncontaining silica gel saturated with hexane
  6. washThe column was eluted with hexane until the yellow band
  7. washThen, it was eluted with methylene chloride
  8. customThe second yellow fraction collected
  9. customwas then subjected to rotary evaporation and hexane
  10. additionwas then added slowly to the concentrated solution
  11. customto precipitate the product as a yellow solid
  12. customThe product was collected
  13. washwashed with hexane
  14. customair-dried overnight

Sources & evidence

ORD record
ord-05c5aa55f8684c399cb19213419aabf7
Source dataset
uspto-grants-1990_04
Patent number
US04916235

Reaction notes

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