N-Iodosuccinimide → HCID 131723500, compound

HRID 1282260

Reaction equation

HRID 1282260 reaction equation
[CH3:1][S:2][CH2:3][O:4]CSC.[P:8]([O-])([O:18][CH2:19][C:20]1C=CC=[CH:22][CH:21]=1)([O:10][CH2:11][C:12]1C=CC=[CH:14][CH:13]=1)=[O:9].IN1C(=O)CCC1=O>C1COCC1.C(OCC)(=O)C>[CH3:1][S:2][CH2:3][O:4][P:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:9]

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 4193600DibenzylphosphateHCID 21902172(Methylsulfanyl)[(methylsulfanyl)methoxy]methane

Product 1

HCID 131723500HCID 131723500, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bis(methylthiomethyl)ether (30 mg, 2.34 mmol) and molecular sieves (300 mg) in THF (100 ml) at room temperature was added dibenzyl phosphate (2.74 g, 9.85 mmol) followed by N-iodosuccinimide (608 mg, 2.71 mmol) and the solution was stirred for 4 h. The reaction mixture was then diluted with ethyl acetate and filtered through a pad of celite. The filtrate was treated with a 1:1 (v:v) solution of saturated aqueous sodium bicarbonate and 5% aqueous sodium thiosulfate. The colorless organic extract was then washed with brine, dried over sodium sulfate and concentrated in vacuo to provide 600 mg (69%) of the title compound:

Workup

  1. filtrationfiltered through a pad of celite
  2. additionThe filtrate was treated with a 1:1 (v:v) solution of saturated aqueous sodium bicarbonate and 5% aqueous sodium thiosulfate
  3. extractionThe colorless organic extract
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3055ee1053f64d82a480eaa4622c6a1f
Source dataset
uspto-grants-2002_09
Patent number
US06455575B2

Linked notes

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