4-Methoxybenzenesulfonyl chloride → 3-(4-Methoxybenzenesulfonyl)-4-oxothiazolidine

HRID 34911Notes

Reaction equation

HRID 34911 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:8][S:7][CH2:6][NH:5]1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>O1CCCC1>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([N:5]2[C:4](=[O:3])[CH2:8][S:7][CH2:6]2)(=[O:19])=[O:18])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 6375914-Thiazolidinone

Product 1

HCID 138540063-(4-Methoxybenzenesulfonyl)-4-oxothiazolidineYield 41.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil) (0.58 g) was added portionwise to a solution of 4-oxothiazolidine (1.50 g) and 4-methoxybenzenesulfonyl chloride (3.01 g) in tetrahydrofuran (30 ml) at 0° C. with stirring and the mixture was stirred for 1 hour at the same temperature. After the solvent was evaporated in vacuo, the residue was mixed with ethyl acetate (10 ml) and water (50 ml) and the resultant precipitate was collected by filtration. The cake was washed with water and diisopropyl ether and recrystallized from a mixture of ethanol and ethyl acetate to give 3-(4-methoxybenzenesulfonyl)-4-oxothiazolidine (1.65 g) as slightly brown prisms.

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. customAfter the solvent was evaporated in vacuo
  3. additionthe residue was mixed with ethyl acetate (10 ml) and water (50 ml)
  4. filtrationthe resultant precipitate was collected by filtration
  5. washThe cake was washed with water and diisopropyl ether
  6. customrecrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-8b82961fc33c472597258e60e2e37873
Source dataset
uspto-grants-1988_08
Patent number
US04764514

Reaction notes

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