Sodium Sulfite → Sodium 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanesulphonate

HRID 1742275Notes

Reaction equation

HRID 1742275 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)[C:8]2=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:33]([O-:36])([O-:35])=[O:34].[Na+:37].[Na+]>C(O)C.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:33]([O-:36])(=[O:35])=[O:34])[C:8]2=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+:37]

Participants

5

Reactant 2

HCID 24437Sodium Sulfite2×HCID 229163881,4,5-Triphenyl-3-(7-bromoheptyl)imidazol-2-one

Product 1

HCID 23671144Sodium 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanesulphonateYield 23.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1,4,5-triphenyl-3-(7-bromoheptyl)-imidazol-2-one (2.0 g) in ethanol (10 ml) was refluxed with a solution of sodium sulphite (0.55 g) in water (5 ml) for 20 hours. More sodium sulphite (0.2 g) was added and refluxing continued for a further 20 hours. The mixture was evaporated to dryness, boiled in ethanol, filtered hot and evaporated to an oil. This was taken up in a small volume of ethanol, excess diethyl ether added and the precipitated solid filtered off and chromatographed on silica gel (dichloromethane/methanol 5:1). The resulting oil in methanol/water 1:1 was passed down an Amberlyst 15 ion exchange resin (Na form) and evaporated to a solid. This was taken up in ethanol and precipitated with diethyl ether giving sodium 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanesulphonate (0.49 g), 23%) as a white solid, m.p. 160° C.

Workup

  1. temperaturerefluxing
  2. customThe mixture was evaporated to dryness
  3. filtrationfiltered hot
  4. customevaporated to an oil
  5. additionadded
  6. filtrationthe precipitated solid filtered off
  7. customchromatographed on silica gel (dichloromethane/methanol 5:1)
  8. customevaporated to a solid
  9. customprecipitated with diethyl ether

Sources & evidence

ORD record
ord-7608b3cc5c944635b7cd0d567d7bea6e
Source dataset
uspto-grants-1994_08
Patent number
US05338752

Reaction notes

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