Dimethylcarbamoyl Chloride → HCID 22939362, compound

HRID 748445Notes

Reaction equation

HRID 748445 reaction equation
[CH2:1]([N+:3]1([O-])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:4]1=[O:14])[CH3:2].C[Si]([C:20]#[N:21])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[CH2:1]([N:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:20]#[N:21])[CH:9]=2)[C:4]1=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86596470HCID 86596470, compound

Product 1

HCID 22939362HCID 22939362, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

1-Ethyl-3-(4-pyridyl)-2-imidazolidinone N-oxide (0.56 g, 2.7 mmol) was dissolved in nitroethane (20 ml), and trimethylsilyl cyanide (0.55 g, 5.5 mmol) and N,N-dimethylcarbamoyl chloride (0.44 g, 4.1 mmol) were added thereto. The mixture was stirred at room temperature for 20 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (5:1, v/v) were collected, concentrated and recrystallized from tetrahydrofuran-hexane to give the titled compound (0.17 g, 29%) as white crystals.

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with ethyl acetate-hexane (5:1
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customrecrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-da64c067e412436da23edf0c8f3ad7e2
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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