Phthalic Anhydride → HCID 67073891, compound

HRID 270174Notes

Reaction equation

HRID 270174 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:19])=[O:5])[CH3:2].[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)=[CH:9][S:8][C:7]=1[N:19]1[C:23](=[O:24])[C:22]2[C:21](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]1=[O:25])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 904007HCID 904007, compound

Product 1

HCID 67073891HCID 67073891, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-4-(3,4-dichlorophenyl)-thiophene-3-carboxylic acid ethyl ester (2 mmol, Example 6 & 7, Part B) and phthalic anhydride (2.2 mmol) in glacial acetic acid (20 mL) was heated at reflux overnight. After cooling to room temperature, the acetic acid was removed in vacuo and the residue triturated with petroleum ether. The crude product was collected by filtration, suspended in acetyl chloride (5 mL), and heated to reflux for one hour. After removing the solvent in vacuo, the residue was 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 from petroleum ether afforded the desired product as a yellow solid in 74% yield.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe acetic acid was removed in vacuo
  4. customthe residue triturated with petroleum ether
  5. filtrationThe crude product was collected by filtration
  6. temperatureheated
  7. temperatureto reflux for one hour
  8. customAfter removing the solvent in vacuo
  9. dissolutionthe residue was 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 from petroleum ether

Sources & evidence

ORD record
ord-7215df2a3ba5454199a138f351885cf8
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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