Hydrochloric Acid → HCID 86646803, compound

HRID 1686158Notes

Reaction equation

HRID 1686158 reaction equation
[CH3:1][C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([O-:18])(=[O:17])=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([O-:23])(=[O:22])=[O:21])[CH:8]=2)[N+:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][S:28]([O-:31])(=[O:30])=[O:29].[Na+].[Na+].Cl>C(O)(=O)C>[NH:3](/[CH:2]=[CH:10]/[CH:11]=[CH:1]/[C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:16])=[O:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([O-:23])(=[O:22])=[O:21])[CH:8]=2)[N+:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][S:28]([OH:31])(=[O:29])=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86614818HCID 86614818, compound

Product 1

HCID 86646803HCID 86646803, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Disodium 2,3-dimethyl-1,3-bis(4-sulphonatobutyl)-3H-indolium-5-sulphonate, crude (1.0 g) and malonaldehyde bis(phenyl)mine) HCl (1.0 g) and acetic acid (10 ml) were heated under nitrogen at 130° C. for 10 hrs to give a dark orange-red solution. The solvent was then evaporated under vacuum; the residue was partitioned in a water/dichloromethane/methanol mixture. UV/Vis analysis (ethanol) confirmed the presence of the product in the upper, aqueous layer (λmax=524 nm) while the malonaldehyde starting material was present mainly in the lower, organic layer (λmax=384 nm). The aqueous layer was evaporated under vacuum and purified by HPLC (water/0.1% TFA and acetonitrile/0.1% TFA eluants). Fractions containing the product were pooled and evaporated, freeze-dried from aqueous solution, with final drying under high vacuum over phosphorus pentoxide to give the title product. Yield 240 mg as a red foam.

Workup

  1. customto give a dark orange-red solution
  2. customThe solvent was then evaporated under vacuum
  3. customthe residue was partitioned in a water/dichloromethane/methanol mixture
  4. customThe aqueous layer was evaporated under vacuum
  5. custompurified by HPLC (water/0.1% TFA and acetonitrile/0.1% TFA eluants)
  6. additionFractions containing the product
  7. customevaporated
  8. customfreeze-dried from aqueous solution
  9. dry with materialwith final drying under high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-d05c39dbef3347739d632945f5405fdd
Source dataset
uspto-grants-2012_04
Patent number
US08148539B2

Reaction notes

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