Phthalic Anhydride → HCID 68860548, compound

HRID 270217Notes

Reaction equation

HRID 270217 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)=[C:9]([CH3:20])[S:8][C:7]=1[NH2:21])=[O:5])[CH3:2].[C:22]1(=O)[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=2)=[C:9]([CH3:20])[S:8][C:7]=1[N:21]1[C:25](=[O:26])[C:24]2[C:23](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]1=[O:27])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 68836937HCID 68836937, compound

Product 1

HCID 68860548HCID 68860548, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-4-[2-(4-bromophenyl)ethyl]-5-methyl-thiophene-3-carboxylic acid ethyl ester (2 mmol, Example 30, 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-a14f74d04adb45b7b2568565b3af94ec
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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