Sodium Iodide → N,N-Diethyl-2-[(iodomethyl)dimethylsilyl]-1-naphthalenecarboxamide

HRID 1604229Notes

Reaction equation

HRID 1604229 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Si:16]([CH2:19]Cl)([CH3:18])[CH3:17])=[O:5])[CH3:2].[Na+].[I-:24]>C(#N)C.CCOCC>[CH2:1]([N:3]([CH2:21][CH3:22])[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Si:16]([CH2:19][I:24])([CH3:18])[CH3:17])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 15457429N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide

Product 1

HCID 19602320N,N-Diethyl-2-[(iodomethyl)dimethylsilyl]-1-naphthalenecarboxamideYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of this naphthalenecarboxamide (1.0 g, 3.0 mmol) and NaI (13.5 g, 90 mmol) in acetonitrile (90 mL) was refluxed overnight, then was diluted with ether and filtered through celite to remove most of the salts. The filtrate was then concentrated and eluted through a plug of silica gel with ethyl acetate. Concentration of the ethyl acetate afforded 1.25 g of the desired compound as a yellow oil, a 98% yield.

Workup

  1. filtrationfiltered through celite
  2. customto remove most of the salts
  3. concentrationThe filtrate was then concentrated
  4. washeluted through a plug of silica gel with ethyl acetate

Sources & evidence

ORD record
ord-5319c1614a934c5cba9514c313d71226
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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