N-Iodosuccinimide → HCID 178469615, compound

HRID 982703Notes

Reaction equation

HRID 982703 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH:13]=[CH:14][S:15][C:3]=12.[I:16]N1C(=O)CCC1=O>>[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH:13]=[C:14]([I:16])[S:15][C:3]=12

Participants

3

Reactant 2

HCID 120273N-IodosuccinimideHCID 178469639HCID 178469639, compound

Product 1

HCID 178469615HCID 178469615, compoundYield 76.3%

Procedure

To a stirring solution of ethyl 7-hydroxythieno[3,2-b]pyridine-6-carboxylate (Elliot, R. L, O'Hanlon, P. J., Rogers, N. H. Tetrahedron 43 (14) 3295-3302 (1987)) (2.50 g, 10.96 mmol) in trifluomethanesulfonic acid (50 mL) at 0° C. was added N-iodo succinimide (2.46 g, 10.96 mmol) portion wise. The mixture was stirred for 1 hour, allowing the solution to warm to ambient temperature. Ice (50 g) was added and the resulting aqueous extracted with CH2Cl2 (3×100 mL). The organic layers were combined, dried over MgSO4 and solvent removed to afford 2.92 g title compound as a white solid.

Workup

  1. extractionthe resulting aqueous extracted with CH2Cl2 (3×100 mL)
  2. dry with materialdried over MgSO4 and solvent
  3. customremoved

Sources & evidence

ORD record
ord-a7a381836fbf4767b769ea31ce9be6e4
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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