Water → HCID 13312663, compound

HRID 1262569Notes

Reaction equation

HRID 1262569 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([S:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:16])=[C:6]([CH:8]2[NH:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])[CH:7]=1.[Mn]([O-])(=O)(=O)=[O:24].[K+].O.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH2:17]([S:15]([C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=1[CH:8]1[NH:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])(=[O:24])=[O:16])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 20456972HCID 20456972, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13312663HCID 13312663, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(5-chloro-2-hexylsulfinylphenyl)hydantoin (4.8 g, 0.014 mol) in glacial acetic acid (50 ml) was added potassium permanganate (2.2 g, 0.014 mol) and water (5 ml). The mixture was stirred at room temperature for 45 minutes then poured into 10% sodium bisulfite solution (50 ml). The resulting solution was extracted with ether, the ethereal extract then dried (MgSO4) and evaporated under reduced pressure. The brown oily residue was chromatographed on silica gel and the product eluted with ethyl acetate:hexane (40:60). Evaporation of the eluate under reduced pressure afforded 1.32 g of product as a white solid (26% yield). M.P. 188°-189° C.

Workup

  1. extractionThe resulting solution was extracted with ether
  2. extractionthe ethereal extract
  3. dry with materialthen dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe brown oily residue was chromatographed on silica gel
  6. washthe product eluted with ethyl acetate:hexane (40:60)
  7. customEvaporation of the eluate under reduced pressure

Sources & evidence

ORD record
ord-811248095efc428a974e3194bbe7632c
Source dataset
uspto-grants-1984_06
Patent number
US04452806

Reaction notes

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