Dimethylformamide → Epoxide resin

HRID 1861236Notes

Reaction equation

HRID 1861236 reaction equation
[CH2:1](N)[CH:2]=[CH2:3].[CH:5]1[CH:10]=[C:9](Cl)[CH:8]=[C:7]([C:12]([O:14]O)=O)[CH:6]=1.[CH3:16]N([CH:19]=[O:20])C>C(Cl)Cl>[CH2:3]=[CH:2][C:1]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1.[CH2:3]=[CH:2][C:1]1[CH:9]=[CH:8][C:7]([CH:6]=[CH2:5])=[CH:12][CH:16]=1.[CH2:19]1[O:20][CH:1]1[CH2:2][O:14][CH2:12][C:7]1[CH:6]=[CH:5][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7853AllylamineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 16213861Epoxide resin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To PNP resin (23a) (0.5 g, 0.77 mmol/g loading) at room temperature was added allylamine (125 μL, 1.67 mmol) in 2 mL of DMF. The resin was shaken overnight and then filtered. It was sequentially washed with DMF and DCM. After being dried in vacuo, the olefin resin (24a, 100 mg) was treated with mCPBA (80%, 72 mg, 0.355 mmol) in DCM for 16 hrs. The reaction mixture was filtered, and the resin was washed with DCM. Epoxide resin 12a was provided upon drying in vacuo. See FIG. 25.

Workup

  1. filtrationfiltered
  2. washIt was sequentially washed with DMF and DCM
  3. customAfter being dried in vacuo
  4. filtrationThe reaction mixture was filtered
  5. washthe resin was washed with DCM

Sources & evidence

ORD record
ord-db4b0936c9e744b580ffe4b5516cfa1a
Source dataset
uspto-grants-2003_03
Patent number
US06531470B1

Reaction notes

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