1,4-Dichlorobenzene → 1-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodide

HRID 389235

Reaction equation

HRID 389235 reaction equation
[CH3:1][C:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N+:13]([C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[CH2:19][I:20])([O-:15])=[O:14].C1C(Cl)=CC=C(Cl)C=1>>[I-:20].[N+:13]([C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[CH2:19][N+:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH3:12])([CH3:11])[C:2]=1[CH3:1])([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 46851,4-DichlorobenzeneHCID 154273H-Indole, 2,3,3-trimethyl-HCID 226090731-(Iodomethyl)-3,5-dinitrobenzene

Product 1

HCID 179021401-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodideYield 55.9%

Conditions

Temperature
90 °C

Procedure

To 2,3,3-trimethylindolenine (1.64 g) was added 3,5-dinitrobenzyl iodide (3.71 g) and dichlorobenzene (15 ml). After heating to 90° C. for 6 hours the mixture was allowed to cool and the resultant precipitate removed by filtration. The solid was washed with dichlorobenzene (2×10 ml) and ether (2×50 ml). The material was dried in a vacuum oven to give the product as a yellow solid (2.69 g).

Workup

  1. temperatureto cool
  2. customthe resultant precipitate removed by filtration
  3. washThe solid was washed with dichlorobenzene (2×10 ml) and ether (2×50 ml)
  4. customThe material was dried in a vacuum oven

Sources & evidence

ORD record
ord-754140fff8a546979a083679d9b20aac
Source dataset
uspto-grants-2013_02
Patent number
US08378120B2

Linked notes

Loading…