Phthalic Anhydride → HCID 12917679, compound

HRID 1660445Notes

Reaction equation

HRID 1660445 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12>C(O)(=O)C>[CH3:1][S:2][CH:3]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]3[C:15]2=[O:20])=[CH:12][CH:13]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 12819446HCID 12819446, compound

Product 1

HCID 12917679HCID 12917679, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl α-methylthio(p-aminophenyl)acetate (760 mg) and 533 mg of phthalic anhydride were dissolved in 8 ml of acetic acid, and the solution was heated under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, and 100 ml of an aqueous solution of sodium bicarbonate was added. The mixture was extracted once with 20 ml of methylene chloride, and then twice with 10 ml of methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 1.222 g of methyl α-methylthio(p-phthalimidophenyl)acetate as colorless crystals in a yield of 99.5%.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and 100 ml of an aqueous solution of sodium bicarbonate
  4. additionwas added
  5. extractionThe mixture was extracted once with 20 ml of methylene chloride
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ed83f27652042c0bf029211d33d5323
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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