Phthalic Anhydride → HCID 68858747, compound

HRID 2212312Notes

Reaction equation

HRID 2212312 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][C:14]=2[Cl:22])=[CH:9][S:8][C:7]=1[NH2:23])=[O:5])[CH3:2].[C:24]1(=O)[O:29][C:27](=[O:28])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:20])[CH3:21])=[CH:15][C:14]=2[Cl:22])=[CH:9][S:8][C:7]=1[N:23]1[C:27](=[O:28])[C:26]2[C:25](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:24]1=[O:29])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 68831032HCID 68831032, compound

Product 1

HCID 68858747HCID 68858747, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-4-[2-(2-chloro-4-isopropylphenyl)vinyl]-thiophene-3-carboxylic acid ethyl ester (2 mmol, Example 31, Part B) and phthalic anhydride (2.2 mmol) in glacial acetic acid (20 mL) is heated at reflux overnight. After cooling to room temperature, the acetic acid is removed in vacuo and the residue triturated with petroleum ether. The crude product is collected by filtration, suspended in acetyl chloride (5 mL), and heated to reflux for one hour. After removing the solvent in vacuo, the residue is dissolved in ethyl acetate (30 mL), washed sequentially with 5% aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Recrystallization affords the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. customthe acetic acid is removed in vacuo
  4. customthe residue triturated with petroleum ether
  5. filtrationThe crude product is collected by filtration
  6. temperatureheated
  7. temperatureto reflux for one hour
  8. customAfter removing the solvent in vacuo
  9. dissolutionthe residue is dissolved in ethyl acetate (30 mL)
  10. washwashed sequentially with 5% aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL)
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customRecrystallization

Sources & evidence

ORD record
ord-edafb816e31b4d7da4ad278a20f99ea2
Source dataset
uspto-grants-2006_09
Patent number
US07101905B2

Reaction notes

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