Phthalaldehydic acid → HCID 19086265, compound

HRID 1032981Notes

Reaction equation

HRID 1032981 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[C:15](O)(=O)[C:16]1[C:17](=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:18]=[O:19].[BH4-].[Na+]>C(O)C>[O:19]=[C:18]1[C:17]2[C:16](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][N:1]1[C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[S:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8406Phthalaldehydic acidHCID 4311764Sodium borohydrideHCID 128509725-(4-Aminophenyl)thiazolidine-2,4-dione

Product 1

HCID 19086265HCID 19086265, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into 50 ml of ethanol were dissolved 4.90 g of 5-(4-aminophenyl)-thiazolidine-2,4-dione and 3.54 g of phthalaldehydic acid, and the solution was refluxed for 2 hours. After cooling by standing, 1.78 g of sodium borohydride were added and the mixture was stirred for 20 minutes at room temperature. Thereafter, solvent was distilled off under reduced pressure and 10 ml of glacial acetic acid were added to the residue, which was stirred for 10 minutes at 100 ° C. After cooling by standing, 100 ml of water were added and the crystals deposited were collected by filtration, washed with water and dried. These were recrystallized from ethanol to obtain 6.90 g of title compound.

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. temperatureAfter cooling
  3. distillationThereafter, solvent was distilled off under reduced pressure and 10 ml of glacial acetic acid
  4. additionwere added to the residue, which
  5. stirringwas stirred for 10 minutes at 100 ° C
  6. temperatureAfter cooling
  7. addition100 ml of water were added
  8. filtrationthe crystals deposited were collected by filtration
  9. washwashed with water
  10. customdried
  11. customThese were recrystallized from ethanol

Sources & evidence

ORD record
ord-720e7ed39ba74a2ea9b99e00f6037b11
Source dataset
uspto-grants-1994_05
Patent number
US05308856

Reaction notes

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