1,4-Butane sultone → 2,3-Dimethyl-1,3-bis(4-sulfobutyl)-5-sulfo-3H-indole

HRID 500099

Reaktionsgleichung

Reaktionsgleichung von HRID 500099
[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]1[S:29](=[O:31])(=[O:30])[O:28][CH2:27][CH2:26][CH2:25]1.S1(CCCC1)(=O)=O>C(OCC)C>[CH3:1][CH: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:21])=[O:22])[CH:8]=2)[N:3]1[CH2:27][CH2:26][CH2:25][CH2:24][S:29]([OH:31])(=[O:30])=[O:28]

Komponenten

5

Edukt 3

HCID 154111,4-Butane sultoneHCID 31347SulfolaneHCID 593662262,3-Dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid

Produkt 1

HCID 866461922,3-Dimethyl-1,3-bis(4-sulfobutyl)-5-sulfo-3H-indoleAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To 2,3-dimethyl-3-(4-sulfobutyl)-5-sulfo-3H-indole (10 g) was added butane sultone (30 g) and the mixture heated to 140° C. overnight. On cooling to room temperature, sulfolan (20 ml) was added and the mixture poured into diethyl ether (500 ml). The resultant precipitate was removed by filtration and dried to give the desired product (12 g).

Aufarbeitung

  1. temperatureOn cooling to room temperature
  2. customThe resultant precipitate was removed by filtration
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-967fe06e8ce64cbea94cfa6f6fa5c726
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767829B2

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