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

HRID 500099

Reaction equation

HRID 500099 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]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]

Participants

5

Reactant 3

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

Product 1

HCID 866461922,3-Dimethyl-1,3-bis(4-sulfobutyl)-5-sulfo-3H-indoleYield 86.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-967fe06e8ce64cbea94cfa6f6fa5c726
Source dataset
uspto-grants-2010_08
Patent number
US07767829B2

Linked notes

Loading…