Hydrochloric Acid → 4-(1,1-Dioxo-1,2-thiazolidin-2-yl)benzoic acid

HRID 2411138Notes

Reaction equation

HRID 2411138 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:21][CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].Cl>ClCCl>[O:25]=[S:24]1(=[O:26])[CH2:23][CH2:22][CH2:21][N:1]1[C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 66250114-(1,1-Dioxo-1,2-thiazolidin-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-aminobenzoate (0.92 g) and triethylamine (1.5 mL) were dissolved in dichloromethane (10 mL), 3-chloropropane-1-sulfonyl chloride (0.9 mL) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, 1N hydrochloric acid was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in N,N-dimethylformamide (8 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1 mL) was added, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue (1.5 g) was dissolved in ethanol (20 mL), 1N aqueous sodium hydroxide solution (8.4 mL) was added, and the mixture was stirred at 60° C. for 3 hr. To the reaction mixture were added 1N hydrochloric acid (9.2 mL) and water, and the precipitate was collected by filtration to give the title compound (0.98 g).

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (8 mL)
  7. addition1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1 mL) was added
  8. stirringthe mixture was stirred at room temperature for 3 hr
  9. additionTo the reaction mixture was added 1N hydrochloric acid
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with saturated brine
  12. customthe solvent was evaporated
  13. dissolutionThe obtained residue (1.5 g) was dissolved in ethanol (20 mL)
  14. addition1N aqueous sodium hydroxide solution (8.4 mL) was added
  15. stirringthe mixture was stirred at 60° C. for 3 hr
  16. additionTo the reaction mixture were added 1N hydrochloric acid (9.2 mL) and water
  17. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b98230c0bf7444bba18e1820bac1443f
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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