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 508303

Reaktionsgleichung

Reaktionsgleichung von HRID 508303
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 866953434-[2-[6-anilino-1,3,5-hexatrienyl]-3-methyl-5-sulfo-3-(4-sulfobutyl)-3H-1-indoliumyl]-1-butanesulfonateAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21895370AcOH AcOAcLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-cb08a2ebd89547888a95bf1a38c5ffb1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09095612B2

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