Sodium Iodide → 3-Iodomethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione

HRID 231560

Reaction equation

HRID 231560 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:4]1=[O:16].[I-:17].[Na+]>CC(C)=O>[I:17][CH2:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:4]1=[O:16]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 200334793-Chloromethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione

Product 1

HCID 200335443-Iodomethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 15.2 g (0.06 moles) 3-chloromethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione (according to Example 1) and 10.7 g (0.066 moles) sodium iodide in acetone were refluxed for 8 hours in acetone. The precipitated sodium chloride was then filtered off, and the filtrate was concentrated, extracted with chloroform and the extract once more concentrated. The desired product was obtained in a yield of 92%. Melting point: 156° C.

Workup

  1. filtrationThe precipitated sodium chloride was then filtered off
  2. concentrationthe filtrate was concentrated
  3. extractionextracted with chloroform
  4. extractionthe extract once more
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-24dd3ef3458d4214aa2f8d4a0a3fc612
Source dataset
uspto-grants-1989_07
Patent number
US04847285

Linked notes

Loading…