p-Anisoyl chloride → 3-(4-Methoxybenzoyl)-4-oxothiazolidine

HRID 34909Notes

Reaction equation

HRID 34909 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[O:12]=[C:13]1[CH2:17][S:16][CH2:15][NH:14]1.C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:14]2[C:13](=[O:12])[CH2:17][S:16][CH2:15]2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 6375914-Thiazolidinone

Product 1

HCID 138539863-(4-Methoxybenzoyl)-4-oxothiazolidineYield 62.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-methoxybenzoyl chloride (20.7 g) in tetrahydrofuran (50 ml) was added dropwise to a mixture of 4-oxo-thiazolidine (12.5 g) and triethylamine (16.9 ml) in tetrahydrofuran (200 ml) at -5° C. with stirring. The mixture was stirred at that temperature for 3 hours and at room temperature for 4 hours, and allowed to stand overnight. After the solvent was evaporated in vacuo, the residue was mixed with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate and then with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(4-methoxybenzoyl)-4-oxothiazolidine (18.1 g) as slightly brown prisms.

Workup

  1. stirringThe mixture was stirred at that temperature for 3 hours and at room temperature for 4 hours
  2. customAfter the solvent was evaporated in vacuo
  3. additionthe residue was mixed with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialwith water, dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-2ff8a32f1b9e40a49bf580642295e58a
Source dataset
uspto-grants-1988_08
Patent number
US04764514

Reaction notes

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