Water → 3-[3-(2-Aminopyridin-3-yloxy)propyl]thiazolidine-2,4-dione

HRID 357145Notes

Reaction equation

HRID 357145 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11]Cl)=[CH:6][CH:5]=[CH:4][N:3]=1.[Na].[S:14]1[CH2:18][C:17](=[O:19])[NH:16][C:15]1=[O:20].[I-].[Na+].O>CN(C)C=O>[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][N:16]2[C:17](=[O:19])[CH2:18][S:14][C:15]2=[O:20])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 189368002-Amino-3-(3-chloropropyloxy)pyridineHCID 867387272,4-Thiazolidinedione sodium salt

Product 1

HCID 189367993-[3-(2-Aminopyridin-3-yloxy)propyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 9.33 g (50 mmol) of 2-amino-3-(3-chloropropyloxy)pyridine and 6.97 g (50 mmol) of thiazolidine-2,4-dione sodium salt in 200 ml of N,N-dimethylformamide, 7.49 g (50 mmol) of sodium iodide was added, followed by refluxing at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate) to yield 8.14 g (60.9%, yellow solid) of the desired product.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. distillationafter which the solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate)

Sources & evidence

ORD record
ord-a122f5d4ee1141fe8b1e32748c526b27
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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