Dimethylcarbamoyl Chloride → HCID 22939428, compound

HRID 748430Notes

Reaction equation

HRID 748430 reaction equation
[CH3:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].ClC1C=CC=C(C(OO)=O)C=1.C[Si]([C:30]#[N:31])(C)C.CN(C)C(Cl)=O>C(OCC)(=O)C.O>[C:30]([C:13]1[CH:14]=[C:9]([CH2:8][CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:10]=[CH:11][N:12]=1)#[N:31]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 70297m-Chloroperbenzoic acidHCID 82115Trimethylsilyl cyanideHCID 22939399HCID 22939399, compound

Product 1

HCID 22939428HCID 22939428, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Ethyl 2-methyl-3-(4-pyridyl)propionate (5.9 g, 30.5 mmol) was dissolved in ethyl acetate (25 ml) and 3-Chloroperbenzoic acid (ca. 77%, 7.5 g, 33.4 mmol) was added thereto. The reaction mixture was stirred at room temperature for 14 hrs and subjected to a silica gel (120 g) column chromatography. The fractions eluted with ethyl acetate-ethanol (3:1, v/v) were collected and concentrated. The residue was dissolved in acetonitrile (18 ml), and trimethylsilyl cyanide (4.5 g, 45.0 mmol) and N,N-dimethylcarbamoyl chloride (3.5 g, 32.5 mmol) were added thereto. The reaction mixture was stirred at room temperature for 18 hrs and combined with ethyl acetate and water. The organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (50 g) column chromatography. The fractions eluted with hexane-ethylacetate (4:1, v/v) were collected and concentrated to give the titled compound (3.7 g, 76%).

Workup

  1. washThe fractions eluted with ethyl acetate-ethanol (3:1
  2. customv/v) were collected
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in acetonitrile (18 ml)
  5. stirringThe reaction mixture was stirred at room temperature for 18 hrs
  6. washThe organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. washThe fractions eluted with hexane-ethylacetate (4:1
  10. customv/v) were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-04c50af3ec094135a214933517652e21
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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