Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 86614818 | HCID 86614818 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 86646803 | HCID 86646803 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08148539B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-d05c39dbef3347739d632945f5405fdd |
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| Source note | uspto-grants-2012_04 |
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