Iodine → HCID 19106992, compound

HRID 1460588Notes

Reaction equation

HRID 1460588 reaction equation
[CH2:1]1[C@@H:14]2[C@@:5]([C:15]([OH:17])=[O:16])([C:6]3[C:11]([CH2:12][CH2:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH:3]=[CH:2]1.C(=O)(O)[O-].[Na+].[I-:23].[K+].II.S(=O)(O)[O-].[Na+]>O>[I:23][CH:2]1[CH:3]2[CH2:4][C:5]3([C:6]4[C:11]([CH2:12][CH2:13][CH:14]3[CH2:1]1)=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:15](=[O:17])[O:16]2

Participants

7

Reactant 5

HCID 807IodineHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 15657729HCID 15657729, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 19106992HCID 19106992, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of the compound from Example 6 (10 g, 44 mmol) and sodium bicarbonate (4 g, 48 mmol) in 150 ml water was heated on a steam bath until a solution was obtained. Potassium iodide (14.6 g, 88 mmol) and iodine (22.4 g, 88 mmol) were dissolved in 150 ml water and added to the reaction mixture via an addition funnel. The reaction mixture was placed in a separatory funnel and shaken with sodium bisulfite and then extracted with methylene chloride. The organic phase was dried over sodium sulfate, filtered and evaporated to give the title compound as a yellow solid (13.7 g, 88% yield).

Workup

  1. temperaturewas heated on a steam bath until a solution
  2. customwas obtained
  3. additionadded to the reaction mixture via an addition funnel
  4. customThe reaction mixture was placed in a separatory funnel
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-86dee2d3174e4549a85357f168e1e8dd
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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