Sodium Thiosulfate → 4,3'-Bis(diethoxyphosphoryl)-5'-iodo-[2,2']-bithiophene

HRID 1662886Notes

Reaction equation

HRID 1662886 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:10]=[C:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[S:12][CH:13]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[I:27]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[CH2:7]([O:6][P:4]([C:9]1[CH:10]=[C:11]([C:14]2[S:15][C:16]([I:27])=[CH:17][C:18]=2[P:19]([O:21][CH2:22][CH3:23])([O:24][CH2:25][CH3:26])=[O:20])[S:12][CH:13]=1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 591558484,3'-Bis(diethoxyphosphoryl)-[2,2']-bithiophene

Product 1

HCID 591558664,3'-Bis(diethoxyphosphoryl)-5'-iodo-[2,2']-bithiopheneYield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

In a mixed solvent of chloroform and acetic acid at 1:1, 0.0877 g (0.2 mmols) of 4,3′-bis(diethoxyphosphoryl)-[2,2′]-bithiophene was dissolved, to which 0.2250 g (1.0 mmol) of commercially available N-iodosuccinimide was added at room temperature. Thereafter, the reaction mixture was stirred at room temperature for 8 hours. After the reaction, a sodium thiosulfate aqueous solution was added, followed by extraction with chloroform. The organic phase was washed with a 0.2 N sodium hydroxide aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=2:1) to obtain the specified substance in the form of a yellow solid at a yield of 0.0880 g (yield: 78%). The thus obtained product was used as it is for reaction in Example 12(12).

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. extractionfollowed by extraction with chloroform
  4. washThe organic phase was washed with a 0.2 N sodium hydroxide aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distilling off under reduced pressure
  8. customthe resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=2:1)
  9. customto obtain the specified substance in the form of a yellow solid at a yield of 0.0880 g (yield: 78%)
  10. customis for reaction in Example 12(12)

Sources & evidence

ORD record
ord-71c92725a88a48a79f8402022c9ea4f7
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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