Sodium Iodide → 1-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodide

HRID 2306533Notes

Reaction equation

HRID 2306533 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[CH3:15][C:16]1[C:24]([CH3:26])([CH3:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.[I-:27].[Na+]>S1(CCCC1)(=O)=O>[I-:27].[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7][N+:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24]([CH3:26])([CH3:25])[C:16]=1[CH3:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 154273H-Indole, 2,3,3-trimethyl-HCID 94673Benzene, 1-(chloromethyl)-3,5-dinitro-

Product 1

HCID 179021401-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodideYield 57%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

3,5-Dinitrobenzyl chloride (100 mg, 0.46 mmol), 2,3,3-trimethylindole (74 μ, 73.2 mg, 0.46 mmol) and sodium iodide (69 mg, 0.46 mmol) were heated at 100° C. in sulpholane (5 ml) for 16 hours. After cooling to room temperature the product was isolated by reverse phase HPLC (89.7 mg, 0.26 mmol, 57% yield).

Workup

  1. customwas isolated by reverse phase HPLC (89.7 mg, 0.26 mmol, 57% yield)

Sources & evidence

ORD record
ord-0dd40617dc424c7cac1f85de59099d2b
Source dataset
uspto-grants-2004_12
Patent number
US06828116B1

Reaction notes

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