Methanol → [5-(1,2-Dithiolan-3-yl)pentyl]urea

HRID 849570Notes

Reaction equation

HRID 849570 reaction equation
CO.C([NH2:7])CCC.[S:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2C(=O)C3C(=CC=CC=3)[C:19]2=[O:28])[S:9]1>C1(C)C=CC=CC=1>[S:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH2:7])=[O:28])[S:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 8007ButylamineHCID 183579972-[5-(1,2-Dithiolan-3-yl)pentyl]isoindole-1,3-dione

Product 1

HCID 18357983[5-(1,2-Dithiolan-3-yl)pentyl]urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 ml of methanol and 2 ml of butylamine were added to a solution of 1:6 mmol of 2-[5-(1,2-dithiolan-3-yl)pentyl]isoindole-1,3-dione in 3 ml of toluene. The resulting mixture was stirred at room temperature for 5 hours and 30 minutes. The reaction mixture was then allowed to stand overnight at room temperature. At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the resulting residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. 5 ml of tetrahydrofuran were added to the residue. 0.32 ml of trimethylsilyl isocyanate was then added dropwise to the resulting mixture, whilst ice-cooling, and then the mixture was stirred at room temperature for 3 hours and 30 minutes. At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure and the residue was subjected to silica gel column chromatography, using 1:0 and 5:1 by volume mixtures of ethyl acetate and methanol as eluent. The solvent was removed from the eluate by distillation under reduced pressure. The residue was recrystallized from ethyl acetate, to give 80 mg of the title compound as yellow crystals, melting at 74 to 78° C.

Workup

  1. waitto stand overnight at room temperature
  2. customAt the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure
  3. additionWater was added to the resulting residue
  4. extractionafter which it was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEthyl acetate was removed from the
  8. extractionextract by distillation under reduced pressure
  9. addition5 ml of tetrahydrofuran were added to the residue
  10. addition0.32 ml of trimethylsilyl isocyanate was then added dropwise to the resulting mixture, whilst ice-
  11. temperaturecooling
  12. stirringthe mixture was stirred at room temperature for 3 hours and 30 minutes
  13. customAt the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure
  14. additionWater was added to the residue
  15. extractionafter which it was extracted with ethyl acetate
  16. washThe extract was washed with a saturated aqueous solution of sodium chloride
  17. dry with materialdried over anhydrous sodium sulfate
  18. customEthyl acetate was removed from the
  19. extractionextract by distillation under reduced pressure
  20. customThe solvent was removed from the
  21. distillationeluate by distillation under reduced pressure
  22. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-caf3389df2a442bf8f03f79d295719fb
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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