Dimethylcarbamoyl Chloride → HCID 22929930, compound

HRID 1296006Notes

Reaction equation

HRID 1296006 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12][CH3:13])=[N+:9]([O-])[CH:10]=1)=[N+:2]=[N-:3].[CH3:14][N:15](C)C(Cl)=O.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(#N)C>[N:1]([CH2:4][C:5]1[C:10]([C:14]#[N:15])=[N:9][C:8]([CH2:12][CH3:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22929772HCID 22929772, compound

Product 1

HCID 22929930HCID 22929930, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After dissolving 5-(azidomethyl)-2-ethyl-1-pyridiniumolate (2.16 g, 12.1 mmol) in acetonitrile (25 ml), 1.77 ml of trimethylsilylnitrile (13.3 mmol) and 1.23 ml of dimethylcarbamoyl chloride (13.3 mmol) were added under a nitrogen stream and the mixture was stirred at room temperature for 66 hours. Saturated aqueous sodium hydrogencarbonate was added for treatment and extraction was performed with ethyl acetate. The extract was dried over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (2.05 g) as a colorless oil. (90.4% yield)

Workup

  1. additionwere added under a nitrogen stream
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b720f980eef247fd9c6152126c878968
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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