N,N'-Diphenylformamidine → 3-methyl-2-((E)-2-phenylamino-vinyl)-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

HRID 553022Notes

Reaction equation

HRID 553022 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:27]1([NH:33][CH:34]=NC2C=CC=CC=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO>[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:34]/[NH:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 94888N,N'-DiphenylformamidineHCID 866399822,3-dimethyl-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

Product 1

HCID 866399813-methyl-2-((E)-2-phenylamino-vinyl)-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.822 g (2 mmol) 2,3-dimethyl-1,3-bis-(3-sulfo-propyl)-3H-indolium sodium salt 7 and 0.49 g (2.5 mmol) N,N′-diphenyl-formamidine are dissolved in 20 ml methanol and stirred for about four hours under reflux. The solvent is removed in vacuum after cooling to room temperature. The residue is washed carefully with ethyl acetate. A dark yellow solid is obtained which is processed without further purification.

Workup

  1. temperatureunder reflux
  2. customThe solvent is removed in vacuum
  3. washThe residue is washed carefully with ethyl acetate
  4. customA dark yellow solid is obtained which
  5. customis processed without further purification

Sources & evidence

ORD record
ord-1fb798efe658416a8eba39e595841675
Source dataset
uspto-grants-2011_05
Patent number
US07951959B2

Reaction notes

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