Phthalimide → HCID 11608126, compound

HRID 720751Notes

Reaction equation

HRID 720751 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]([C@H:14]1[O:16][CH2:15]1)Cl.C(=O)([O-])[O-].[Na+].[Na+].CC(C)([O-])C.[K+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(O)(C)C>[CH2:12]([C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6])[C@@H:14]1[O:16][CH2:15]1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 10340Sodium CarbonateHCID 149428(+)-EpichlorohydrinHCID 23665647Potassium tert-butoxide

Product 1

HCID 11608126HCID 11608126, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 3776IsopropanolSolvent2×

Conditions

Temperature
15 °C

Procedure

Into a reaction vessel were put phthalimide (200.0 g, 1.36 mol), (S)-epichlorohydrin (226.4 g, 2.45 mol), anhydrous sodium carbonate (14.40 g, 0.136 mol), benzyltrimethylammonium chloride (25.24 g, 0.136 mol) and isopropanol (1.2 L) and the mixture was reacted at 25° C. for 22 hours to give crude N-(3-chloro-2-hydroxypropyl)phthalimide. The reaction mixture is cooled to 15° C. and then thereto was dropped a mixture of potassium tert-butoxide (183.0 g, 1.63 mol) and isopropanol (0.8 L) over a two hours period and the mixture was stirred for 2 hours at the same temperature. The solvent was removed and to the residue was added ethyl acetate (1.3 L). The mixture was washed with water (0.65 L), and then ethyl acetate was removed to give crude (S)-glycidylphthalimide. The crude product was crystallized from ethyl acetate-hexane to give the object (S)-glycidylphthalimide (206.3 g, yield: 75%, optical purity: 98% e.e.) as white crystals. mp 99–101° C.

Workup

  1. customInto a reaction vessel were put
  2. customto give crude N-(3-chloro-2-hydroxypropyl)phthalimide
  3. additionwas dropped
  4. customThe solvent was removed and to the residue
  5. additionwas added ethyl acetate (1.3 L)
  6. washThe mixture was washed with water (0.65 L)
  7. customethyl acetate was removed
  8. customto give crude (S)-glycidylphthalimide
  9. customThe crude product was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-948448bd84a3437f9ef6a2035e685fad
Source dataset
uspto-grants-2006_11
Patent number
US07135576B2

Reaction notes

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