Dimethylcarbamoyl Chloride → HCID 22939314, compound

HRID 748336Notes

Reaction equation

HRID 748336 reaction equation
[CH3:1][CH2:2][O:3][P:4]([O:15][CH2:16][CH3:17])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][N+:11]([O-])=[CH:10][CH:9]=1)=[O:5].C[Si]([C:22]#[N:23])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:22]([C:12]1[CH:13]=[C:8]([CH2:7][CH2:6][P:4](=[O:5])([O:15][CH2:16][CH3:17])[O:3][CH2:2][CH3:1])[CH:9]=[CH:10][N:11]=1)#[N:23]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 59750481HCID 59750481, compound

Product 1

HCID 22939314HCID 22939314, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

Diethyl 2-(4-pyridyl)ethylphosphonate N-oxide (9.9 g, 38 mmol) was dissolved in nitroethane (200 ml), and trimethylsilyl cyanide (7.5 g, 75 mmol) and N,N-dimethylcarbamoyl chloride (6.1 g, 56 mmol) were added thereto. The mixture was stirred at room temperature for 12 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-methanol (15:1) were collected and concentrated to give the titled compound (7.3 g, 71%).

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with ethyl acetate-methanol (15:1)
  3. customwere collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa6df52787784a8280637e9b628f5920
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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