Sodium Bicarbonate → HCID 22504399, compound

HRID 1838330Notes

Reaction equation

HRID 1838330 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9](SC)=[CH:8][C:7]=1[I:14])=[O:4].O[O:18][S:19]([O-:21])=O.[K+].[C:23](=O)([O-])O.[Na+]>O1CCCC1.O>[CH3:15][C:2]([CH3:1])([CH3:16])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:19]([CH3:23])(=[O:21])=[O:18])=[CH:8][C:7]=1[I:14])=[O:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22504384HCID 22504384, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22504399HCID 22504399, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of 2,2-dimethyl-N-(2-iodo-4-methylthiophenyl)propionamide in a mixture of tetrahydrofuran/water mixture (2:1, 210 ml), OXONE (registered trademark) (22.0 mg) was added and the mixture was stirred at 15 to 30° C. for 2 hours. After completion of the reaction, the reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was recrystallized (ethyl acetate/n-hexane) to obtain 5.22 g of the desired product as a white crystal.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washwashed with a saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was recrystallized (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-fd1c85a7341242d58a3a6b6c682fc717
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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