Sodium Iodide → 2-Iodo-1-[2-[(2-methoxyphenoxy)methyl]-3-thiazolidinyl]ethanone

HRID 1722832Notes

Reaction equation

HRID 1722832 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[O:4].[I-:20].[Na+]>CC(C)=O.O>[I:20][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[O:4]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 10447619HCID 10447619, compound

Product 1

HCID 103858742-Iodo-1-[2-[(2-methoxyphenoxy)methyl]-3-thiazolidinyl]ethanoneYield 75.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 3-α-chloroacetyl-2-(o-methoxyphenoxy)methyl-thiazolidine (6 g) in acetone (80 ml) is heated to reflux temperature in the presence of sodium iodide (5 g) for 3 hours and then poured in ice and water (400 ml). The precipitate is collected, dissolved in methylene dichloride and washed with water, 5% aqueous NaHCO3, 2N sodium thiosulphate, water and dried on Na2SO4. After the usual work-up, the residue is crystallized from acetone and isopropanol to give 5.92 g of 3-α-iodoacetyl-2-(o-methoxyphenoxy)methyl-thiazolidine m.p. 81°-83° C. Using this procedure sodium bromide, the 3-α-bromoacetyl-2-(o-methoxyphenoxy)methyl-thiazolidine is obtained, m.p. 82°-84° C.

Workup

  1. additionpoured in ice
  2. customThe precipitate is collected
  3. dissolutiondissolved in methylene dichloride
  4. washwashed with water, 5% aqueous NaHCO3, 2N sodium thiosulphate, water
  5. customdried on Na2SO4
  6. customAfter the usual work-up, the residue is crystallized from acetone and isopropanol

Sources & evidence

ORD record
ord-fab2b065c09e4cecb1382ab3e0989764
Source dataset
uspto-grants-1989_08
Patent number
US04857643

Reaction notes

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