Acetic Anhydride → HCID 86699468, Verbindung

HRID 1480507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480507
[Cl:1][C:2]1[CH:3]=[C:4]2[C:17]([CH3:19])([CH3:18])[C:16]([CH3:20])=[N:15][C:5]2=[N+:6]([CH2:8][CH2:9][CH2:10][S:11]([O-:14])(=[O:13])=[O:12])[CH:7]=1.[CH3:21][C:22]1[C:30]([CH3:32])([CH3:31])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([S:33]([O-:36])(=[O:35])=[O:34])[CH:28]=2)[N+:23]=1[CH2:37][CH2:38][CH2:39][S:40]([O-:43])(=[O:42])=[O:41].[Na+:44].[Br-].[Br:46]/[C:47](=[CH:56]\NC1C=CC=CC=1)/[CH:48]=[NH+]/C1C=CC=CC=1.C(OC(=O)C)(=O)C>C(OCC)C.N1C=CC=CC=1>[Br:46]/[C:47](/[CH:56]=[CH:20]/[C:16]1[C:17]([CH3:19])([CH3:18])[C:4]2[C:5]([N:15]=1)=[N+:6]([CH2:8][CH2:9][CH2:10][S:11]([O-:14])(=[O:13])=[O:12])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:48]\[CH:21]=[C:22]1\[N:23]([CH2:37][CH2:38][CH2:39][S:40]([O-:43])(=[O:42])=[O:41])[C:24]2[C:29]([C:30]\1([CH3:31])[CH3:32])=[CH:28][C:27]([S:33]([O-:36])(=[O:35])=[O:34])=[CH:26][CH:25]=2.[Na+:44].[Na+:44]

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 71692790HCID 71692790, VerbindungHCID 866994663-(5-Chloro-2,3,3-trimethyl-3H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)propane-1-sulfonateHCID 178419561HCID 178419561, Verbindung

Produkt 1

HCID 86699468HCID 86699468, VerbindungAusbeute 130,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A 100-mL round-bottom flask fitted with a reflux condenser was charged with 3-(5-chloro-2,3,3-trimethyl-3H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)propane-1-sulfonate (55, 500 mg), sodium 2,3,3-trimethyl-1-(3-sulfonatopropyl)-3H-indolium-5-sulfonate (4, 500 mg), (E)-N—((Z)-2-bromo-3-(phenylamino)allylidene)benzenaminium bromide (8, 100 mg), pyridine (1 mL), and acetic anhydride (10 mL) were added to the flask. The mixture was heated at 115° C. for 2 h, allowed to cool to room temperature, and diluted with ethyl ether (25 mL). The resulting dark blue dye precipitate was collected by filtration, dissolved in water (20 mL), and purified by preparative reverse-phase HPLC to afford the 9 as a blue powder (285 mg, 50%, UV 668 nm).

Aufarbeitung

  1. customA 100-mL round-bottom flask fitted with a reflux condenser
  2. additionwere added to the flask
  3. temperatureto cool to room temperature
  4. filtrationThe resulting dark blue dye precipitate was collected by filtration
  5. dissolutiondissolved in water (20 mL)
  6. custompurified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-428cdf4a8421424d8459f21d0a920e98
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09408924B2

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