Sodium Iodide → HCID 70142577, compound

HRID 363146Notes

Reaction equation

HRID 363146 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-chloroacetyl4-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-iodoacetyl4-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-c798b1eb8d9c4699ba533b3ccb50aa82
Source dataset
uspto-grants-1999_02
Patent number
US05872224

Reaction notes

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