N-(2,3-Epoxypropyl)phthalimide → AGN-PC-0KLTOI

HRID 2201228Notes

Reaction equation

HRID 2201228 reaction equation
NC(N)=[S:3].O1[CH2:19][CH:6]1[CH2:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18]>CO>[S:3]1[CH2:19][CH:6]1[CH2:7][N:8]1[C:12](=[O:13])[C:11]2[C:10](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]1=[O:18]

Participants

4

Reactant 2

HCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 2723790Thiourea

Product 1

HCID 2828744AGN-PC-0KLTOI

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiourea (1.873 g, 24.61 mmol) was added to a solution of N-(2,3-epoxypropyl)phthalimide (2 g, 9.84 mmol) in methanol (25 mL). The mixture was stirred at room temperature for 16 hours, then concentrated under vacuum. The residue was diluted with water (50 ml) and extracted with ethyl acetate (50 ml). The organic extract was washed with brine (50 ml) passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane, afforded the title compound.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was diluted with water (50 ml)
  3. extractionextracted with ethyl acetate (50 ml)
  4. extractionThe organic extract
  5. washwas washed with brine (50 ml)
  6. customevaporated under vacuum
  7. customPurification by chromatography on silica
  8. washeluting with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-153f62342903406099735512a6d2db4a
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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