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 553024Notes

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

Participants

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

customThe solvent is removed in vacuum
temperatureafter cooling to room temperature
washThe residue is washed carefully with ethyl acetate
customA dark brown solid is obtained which
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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