Sodium Sulfite → Sodium 7-(2,4,5-tri-phenylimidazol-1-yl)heptane-sulphonate

HRID 265394Notes

Reaction equation

HRID 265394 reaction equation
[C:1]1([C:7]2[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:32]([O-:35])([O-:34])=[O:33].[Na+:36].[Na+]>C(O)C.O>[C:1]1([C:7]2[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:32]([O-:35])(=[O:34])=[O:33])[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+:36]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 229163771-(7-Bromoheptyl)-2,4,5-triphenylimidazole

Product 1

HCID 23679429Sodium 7-(2,4,5-tri-phenylimidazol-1-yl)heptane-sulphonateYield 32.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,4,5-Triphenyl-1-(7-bromoheptyl)imidazole (0.95 g) was dissolved in hot ethanol (10 ml) and a solution of sodium sulphite (0.38 g) in hot water (5 ml) was added. The white suspension was heated at reflux temperature for 20 hours then evaporated to dryness. The mixture was taken up in dichloromethane, filtered and the filtrate evaporated to an oil which was chromatographed on silica gel (dichloromethane/methanol). The resulting oil was dissolved in methanol and excess ether added giving an oil which slowly solidified to give sodium 7-(2,4,5-tri-phenylimidazol-1-yl)heptane-sulphonate (0.32 g; 32%) as a white solid, m.p. 310° C.

Workup

  1. temperatureThe white suspension was heated
  2. temperatureat reflux temperature for 20 hours
  3. customthen evaporated to dryness
  4. filtrationfiltered
  5. customthe filtrate evaporated to an oil which
  6. customwas chromatographed on silica gel (dichloromethane/methanol)
  7. dissolutionThe resulting oil was dissolved in methanol
  8. additionexcess ether added
  9. customgiving an oil which

Sources & evidence

ORD record
ord-34cd3fdd468a46808ed1ed3e5507a979
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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