Sodium Iodide → HCID 13424016, compound

HRID 1981065Notes

Reaction equation

HRID 1981065 reaction equation
S(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:9]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(C)(=O)=O.[Na+].[I-:26]>C(#N)C>[I:26][CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:9]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13424015HCID 13424015, compound

Product 1

HCID 13424016HCID 13424016, compoundYield 118.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 1-(2-mesyloxyethyl)-3-carboethoxy-4-methylpyrrole-2-acetate (11.6 g) and 27 g of NaI was heated to reflux with 150 ml of acetonitrile for 1 hour. Solvent was removed by distillation and the residue triturated with water. The insoluble product was separated by filtration, air dried and crystallized from methylenechloride/hexane to yield 14.9 g of ethyl 1-(2-iodoethyl)-3-carboethoxy-4-methylpyrrole-2-acetate as a white solid.

Workup

  1. customSolvent was removed by distillation
  2. customthe residue triturated with water
  3. customThe insoluble product was separated by filtration, air
  4. customdried
  5. customcrystallized from methylenechloride/hexane

Sources & evidence

ORD record
ord-7bb7fecf3e13467f8798de66ddb44aff
Source dataset
uspto-grants-1985_04
Patent number
US04511724

Reaction notes

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