N-Iodosuccinimide → HCID 59155826, compound

HRID 1662884Notes

Reaction equation

HRID 1662884 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[I:14]N1C(=O)CCC1=O.P([O-])([O-])(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[I:14][C:12]1[S:11][CH:10]=[C:9]([P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])[CH:13]=1

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 153633033-(Diethoxyphosphoryl)thiopheneHCID 86630341Sodium phosphate (Na3(PO4)2)

Product 1

HCID 59155826HCID 59155826, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

In 5 ml of a mixed solvent of chloroform:acetic acid=1:1, 0.1101 g (0.5 mmols) of 3-(diethoxyphosphoryl)thiophene was dissolved, to which 0.2362 g (1.05 mmols) of commercially available N-iodosuccinimide was added at room temperature. Thereafter, the reaction mixture was stirred at room temperature for 4 days. After the reaction, a disodium hydrogen phosphate/sodium dihydrogen phosphate buffer solution, adjusted to pH=7, was added, followed by extraction with chloroform. The organic phase was washed with a 0.2N sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed, and the resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane 1:1) to obtain the specified substance in the form of a yellow oil at a yield of 0.1263 g (yield: 73%). The thus obtained substance was used as it is for reaction in Example 12(9).

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. additionwas added
  4. extractionfollowed by extraction with chloroform
  5. washThe organic phase was washed with a 0.2N sodium hydroxide aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane 1:1)
  9. customto obtain the specified substance in the form of a yellow oil at a yield of 0.1263 g (yield: 73%)
  10. customis for reaction in Example 12(9)

Sources & evidence

ORD record
ord-e62db8f22eda466ab3e1fcec2b31b9bd
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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