Sodium Iodide → HCID 70142577, compound

HRID 1956006Notes

Reaction equation

HRID 1956006 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([OH:18])[C:10](=[CH:16][CH:17]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4].[I-:19].[Na+]>CC(C)=O>[I:19][CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([OH:18])[C:10](=[CH:16][CH:17]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 70143857HCID 70143857, compound

Product 1

HCID 70142577HCID 70142577, compoundYield 130.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl N-chloroacetyl-4-aminomethylsalicylate (0.11 g, 0.40 mmoles) was dissolved in acetone (5 mL) and sodium iodide (0.06 g, 0.40 mmoles) was added. The solution was refluxed for 2.5 hours, then cooled to room temperature and filtered. The filtrate was evaporated to dryness to afford a white solid of ethyl N-iodoacetyl-4-aminomethylsalicylate (0.19 g, 100% yield) (m.p. 105°-108° C).

Workup

  1. temperatureThe solution was refluxed for 2.5 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-80962ac25f154a78bdd4ea5f56db2413
Source dataset
uspto-grants-1998_07
Patent number
US05777148

Reaction notes

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