N-(5-(phenylamino)penta-2,5-dienylidene)aniline monohydrochloride → 4-[2-[6-anilino-1,3,5-hexatrienyl]-3-methyl-5-sulfo-3-(4-sulfobutyl)-3H-1-indoliumyl]-1-butanesulfonate

HRID 579412

Reaction equation

HRID 579412 reaction equation
[CH3:1][C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:17])=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([OH:23])(=[O:22])=[O:21])[CH:8]=2)[N+:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][S:28]([OH:31])(=[O:30])=[O:29].Cl.[C:33]1([NH:39][CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=NC2C=CC=CC=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OC(=O)C)(=O)C.C(O)(=O)C>[NH:39]([CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=[CH:1][C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:16])=[O:17])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([OH:23])(=[O:22])=[O:21])[CH:8]=2)[N+:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][S:28]([O-:31])(=[O:29])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 73902N-(5-(phenylamino)penta-2,5-dienylidene)aniline monohydrochlorideHCID 584902382,3-dimethyl-5-sulfo-1,3-di(4-sulfobutyl)-3H-indolium

Product 1

HCID 866953434-[2-[6-anilino-1,3,5-hexatrienyl]-3-methyl-5-sulfo-3-(4-sulfobutyl)-3H-1-indoliumyl]-1-butanesulfonateYield 66.8%

Reagents, catalysts & solvents 1

HCID 21895370AcOH AcOAcSolvent

Procedure

300 mg (0.55 mmol) of 2,3-dimethyl-5-sulfo-1,3-di(4-sulfobutyl)-3H-indolium and 190 mg (0.66 mmol) of N-[5-(phenylamino)-2,4-pentadienylidene]aniline monohydrochloride were heated in 6 mL acetic anhydride-acetic acid (1:1, v/v) mixture for 30 min at 110° C. After cooling the product was precipitated with ethyl acetate, filtered off and washed with ether to give 240 mg (56%) of 4-[2-[6-anilino-1,3,5-hexatrienyl]-3-methyl-5-sulfo-3-(4-sulfobutyl)-3H-1-indoliumyl]-1-butanesulfonate. λmax (abs) 505 nm (methanol). This product was used for following step without additional purification.

Workup

  1. temperatureAfter cooling the product
  2. customwas precipitated with ethyl acetate
  3. filtrationfiltered off
  4. washwashed with ether

Sources & evidence

ORD record
ord-cf309041b4994bbdb4a834b8285c9d4f
Source dataset
uspto-grants-2015_05
Patent number
US09040721B2

Linked notes

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