Hydrochloric Acid → HCID 86614813, compound

HRID 1686156Notes

Reaction equation

HRID 1686156 reaction equation
[CH2:1]([N+:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([CH3:24])([CH2:16][CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:22])=[O:21])[C:4]=1[CH3:25])[CH3:2].Cl>C(O)(=O)C>[NH:3](/[CH:4]=[CH:5]/[CH:16]=[CH:25]/[C:4]1[C:5]([CH3:24])([CH2:16][CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:22])=[O:21])[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([O-:15])(=[O:13])=[O:14])[CH:7]=2)[N+:3]=1[CH2:1][CH3:2])[C:11]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86614810HCID 86614810, compound

Product 1

HCID 86614813HCID 86614813, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Ethyl-2,3-dimethyl-3-(4-sulphobutyl)-3H-indolium-5-sulphonate, crude (1.1 g), malonaldehyde bis(phenyl)mine) HCl (0.5 g) and acetic acid (20 ml) were heated under nitrogen at 130° C. for 8 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 only 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, with final drying under high vacuum over phosphorus pentoxide to give the title product.

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. dry with materialwith final drying under high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-3464471791124bd68e33d6ca5126eac3
Source dataset
uspto-grants-2012_04
Patent number
US08148539B2

Reaction notes

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