Sodium Thiosulfate → HCID 86748315, compound

HRID 2210279Notes

Reaction equation

HRID 2210279 reaction equation
[CH3:1][C:2]1([OH:15])[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7]SC1C=CC=CC=1.C([O-])(O)=O.[Na+].[CH:21]1[CH:26]=[C:25](Cl)[CH:24]=[C:23](C(OO)=O)[CH:22]=1.[O-:32][S:33]([O-:36])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[C:25]1([S:33]([CH2:7][CH:3]2[CH2:4][CH2:5][CH2:6][C:2]2([CH3:1])[OH:15])(=[O:36])=[O:32])[CH:24]=[CH:23][CH:22]=[CH:21][CH:26]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium Bicarbonate2×HCID 86748316HCID 86748316, compound

Product 1

HCID 86748315HCID 86748315, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 9a (1.84 g, 8.28 mmol) and NaHCO3 (2.45 g, 29.2 mmol) in a mixture of CH2Cl2 (40mL) and water (17 mL) was added mCPBA (85%, 3.36 g, 16.5 mmol) in portionwise with stirring vigorously in an ice bath. The mixture 19 was stirred for 15 min. To the mixture were added water (16 mL), NaHCO3 (2.45 g) and mCPBA (1.68 g), and stirring was continued for 20 min. The excess amount of peracid was decomposed with Na2S2O3 solution in the presence of a catalytic amount of KI. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with NaCl solution, and dried over Na2SO4. Filtration and concentration gave 2.69 g of 10a, as white solids, which was used in the next reaction without further purification.

Workup

  1. stirringstirring
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-9e7f10beeb7d4d3c849923423b3e8575
Source dataset
uspto-grants-1995_10
Patent number
US05457217

Reaction notes

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