Sodium Iodide → HCID 88629896, compound

HRID 1195054Notes

Reaction equation

HRID 1195054 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][CH2:16]Br)/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[I-:18].[Na+]>C(C(C)=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][CH2:16][I:18])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 88629807HCID 88629807, compound

Product 1

HCID 88629896HCID 88629896, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

80.55 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(2-bromoethoxy)imino]-acetate and 187.4 g of sodium iodide are boiled under reflux in 1.5 l of methyl ethyl ketone for 1.5 hours. After removal of the solvent by evaporation, the residue is partitioned between 0.6 l of water and 0.2 l of ethyl acetate, the aqueous phase is back-extracted twice with 0.2 l of ethyl acetate each time, the organic extracts are thereupon combined, washed with 0.2 l of aqueous 15% sodium chloride solution, dried and evaporated. The residue is recrystallized from 0.7 l of toluene. 83.5 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(2-iodoethoxy)imino]acetate are obtained.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation
  3. customthe residue is partitioned between 0.6 l of water and 0.2 l of ethyl acetate
  4. extractionthe aqueous phase is back-extracted twice with 0.2 l of ethyl acetate each time
  5. washwashed with 0.2 l of aqueous 15% sodium chloride solution
  6. customdried
  7. customevaporated
  8. customThe residue is recrystallized from 0.7 l of toluene

Sources & evidence

ORD record
ord-7f33a0e95dd1476fa246c8fe81dd3e99
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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