Sulfite → Sodium 7-(1,4,5-triphenylimidazol-2-yloxy)heptanesulphonate

HRID 1376372Notes

Reaction equation

HRID 1376372 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]=[C:8]2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:33]([O-:36])([O-:35])=[O:34].[Na+:37].[Na+].S([O-])([O-])=O>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]=[C:8]2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][S:33]([O-:36])(=[O:35])=[O:34])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+:37]

Participants

6

Reactant 3

HCID 1099SulfiteHCID 24437Sodium SulfiteHCID 229164121,4,5-Triphenyl-2-(7-bromoheptyloxy)imidazole

Product 1

HCID 23679430Sodium 7-(1,4,5-triphenylimidazol-2-yloxy)heptanesulphonateYield 15%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 1,4,5-triphenyl-2-(7-bromoheptyloxy)-imidazole (2.0 g) in ethanol (10 ml) was refiuxed with a solution of sodium sulphite (0.55 g) in water (5 ml) for 20 hours. More sodi,,m sulphite (0.2 g) in water (1 ml) was added and refiuxed a further 20 hours. The mixture was evaporated to dryness, boiling ethanol added and filtered hot. Chromatography of the flitrate on silica gel (dichloromethane/methanol 5:1) followed by crystallisation from ethanol/isopropanol gave sodium 7-(1,4,5-triphenylimidazol-2-yloxy)heptanesulphonate (0.3 g, 15%) as a colourless solid, m.p. 246-8° C. Found: C, 64.47; H, 5.85; N, 5.09; S, 5.50%; C28H29N2Na04S +2% isopropanol +2% water; Requires: C, 64.19; H, 5.96; N, 5.25; S, 6.01%.

Workup

  1. customThe mixture was evaporated to dryness
  2. additionadded
  3. filtrationfiltered hot
  4. customChromatography of the flitrate on silica gel (dichloromethane/methanol 5:1) followed by crystallisation from ethanol/isopropanol

Sources & evidence

ORD record
ord-47e5e7bd1f094e6c8f225363abad49ca
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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