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2,3-dimethyl-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt → 3-methyl-2-((1E,3E)-4-phenylamino-buta-1,3-dienyl)-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

HRID 553024
Notes
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Reaction equation

HRID 553024 reaction equation
[Na+:1].[CH3:2][C:3]1[C:11]([CH3:19])([CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:17])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]=1[CH2:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24]>C(O)(=O)C.C(OC(=O)C)(=O)C>[Na+:1].[CH3:19][C:11]1([CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:16])=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]([CH2:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:24])=[O:25])=[C:3]1/[CH:2]=[CH:12]/[CH:11]=[CH:3]/[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 866399822,3-dimethyl-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

Product 1

HCID 866399833-methyl-2-((1E,3E)-4-phenylamino-buta-1,3-dienyl)-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

0.822 g (2 mmol) 2,3-dimethyl-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt 7 and 0.65 g (2.5 mmol) malonaldehyde-bisphenylimine-hydrochloride are dissolved in a mixture of 10 ml acetic acid and 20 ml acetic anhydride and stirred at 120° C. for four hours. The solvent is removed in vacuum after cooling to room temperature. The residue is washed carefully with ethyl acetate. A dark brown solid is obtained which is processed without further purification.

Workup

  1. customThe solvent is removed in vacuum
  2. temperatureafter cooling to room temperature
  3. washThe residue is washed carefully with ethyl acetate
  4. customA dark brown solid is obtained which
  5. customis processed without further purification

Sources & evidence

ORD record
ord-4abccfd6646140b48614b4901aa44c6b
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951959B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes