Sodium Thiosulfate → 4-{[4-(Methylsulfonyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

HRID 1644765Notes

Reaction equation

HRID 1644765 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:31])[NH:23][C:24]2[S:25][CH:26]=[C:27](SC)[N:28]=2)=[CH:18][CH:17]=1)(=[O:14])[CH3:13].[S:32]([O-:36])([O-])(=[O:34])=S.[Na+].[Na+]>ClCCl.O>[C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:31])[NH:23][C:24]2[S:25][CH:26]=[C:27]([S:32]([CH3:2])(=[O:36])=[O:34])[N:28]=2)=[CH:18][CH:17]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 575718874-{[4-(Methylthio)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Product 1

HCID 251869354-{[4-(Methylsulfonyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetateYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (1.0 g, 6.0 mmol, maximum 77%) dissolved in dichloromethane (30 mL) was added to a suspension of 82 (0.63 g, 2.0 mmol) in dichloromethane (60 mL). The reaction became homogeneous and the dark brown solution became lighter with time. After 1.25 hours, saturated aqueous sodium thiosulfate was added to the reaction and the reaction mixture was stirred vigorously for 20 minutes. The yellow mixture was diluted with water and the resulting layers separated. The organic layer was washed twice with saturated aqueous sodium bicarbonate, once with brine, dried with anhydrous sodium sulfate and concentrated in vacuo to give a beige solid. The crude product was recrystallized from 50% ethyl acetate/hexane (220 mL). After 4 days the suspension was filtered, the filter pad was washed with hexanes and then diethyl ether, and dried in vacuo at 55° C. overnight to give 83 (0.20 g, 30%) as a light orange solid. Concentration of the filtrate in vacuo followed by triturating the resulting residue with diethyl ether and filtering off the resulting solid yielded an additional 45 mg of 83 as a tan solid.

Workup

  1. customthe resulting layers separated
  2. washThe organic layer was washed twice with saturated aqueous sodium bicarbonate, once with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a beige solid
  6. customThe crude product was recrystallized from 50% ethyl acetate/hexane (220 mL)
  7. filtrationAfter 4 days the suspension was filtered
  8. washthe filter pad was washed with hexanes
  9. dry with materialdiethyl ether, and dried in vacuo at 55° C. overnight

Sources & evidence

ORD record
ord-cc0e14ef450647909e54803c711376a7
Source dataset
uspto-grants-2012_02
Patent number
US08124632B2

Reaction notes

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