Water → Phthalimide

HRID 2290552Notes

Reaction equation

HRID 2290552 reaction equation
COC1C=C(C=CC=1C1SC=CC=1)[NH2:6].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.O>C(O)(=O)C>[C:18]1(=[O:19])[C:17]2[C:16](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15](=[O:20])[NH:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 137686283-Methoxy-4-(2-thienyl)benzenamine

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 5.1 g (0.025 mole) of 3-methoxy-4-(thien-2-yl)aniline (prepared in Example 4) and 4.1 g (0.03 mole) of phthalic anhydride in 20 ml of glacial acetic acid was heated at reflux for approximately 18 hours. The hot reaction mixture was poured into 700 ml of distilled water forming a precipitate. The precipitate was collected by filtration and the filter cake dissolved in methylene chloride. The methylene chloride solution was washed first with a 10% aqueous potassium carbonate solution and then with an aqueous sodium chloride solution. The washed organic solution was dried over anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by evaporation under reduced pressure to yield 8.2 g of 2-[4-thien-2-yl)-3-methoxyphenyl]-1H-isoindol-1,3-(2H)-dione as a solid (mp 153°-155° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. filtrationThe precipitate was collected by filtration
  4. dissolutionthe filter cake dissolved in methylene chloride
  5. washThe methylene chloride solution was washed first with a 10% aqueous potassium carbonate solution
  6. dry with materialThe washed organic solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-78ffe7c6cddf4cdbac7ac79ba891dd3e
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

Loading…