Sodium Iodide → methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetate

HRID 224463Notes

Reaction equation

HRID 224463 reaction equation
S(O[CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[C:9]1[CH2:17][C:18]([O:20][CH3:21])=[O:19])(C)(=O)=O.[I-:22].[Na+]>C(#N)C>[I:22][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[C:9]1[CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 12795003methyl N-(2-mesyloxyethyl)-3-carbomethoxypyrrole-2-acetate

Product 1

HCID 12795009methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 785 mg of methyl N-(2-mesyloxyethyl)-3-carbomethoxypyrrole-2-acetate and 1.83 g of sodium iodide in 10 ml of acetonitrile is refluxed for 1 hour. The cooled reaction mixture is evaporated to dryness under reduced pressure and the residue is triturated with water. The insoluble material is separated by filtration and is air dried, thus obtaining 840 mg (97%) of methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetate (VI, R=H), m.p. 137°-138° C.

Workup

  1. customThe cooled reaction mixture
  2. customis evaporated to dryness under reduced pressure
  3. customthe residue is triturated with water
  4. customThe insoluble material is separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-6182539114784b43bf875b3133e853f1
Source dataset
uspto-grants-1980_11
Patent number
US04232038

Reaction notes

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