Dimethylcarbamoyl Chloride → HCID 22939414, compound

HRID 499604Notes

Reaction equation

HRID 499604 reaction equation
[CH3:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N: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:11]1[N:10]=[C:9]([CH2:8][CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:14]=[CH:13][CH:12]=1)#[N:31]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 70297m-Chloroperbenzoic acidHCID 82115Trimethylsilyl cyanideHCID 22939391HCID 22939391, compound

Product 1

HCID 22939414HCID 22939414, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Ethyl 2-methyl-3-(2-pyridyl)propionate (1.0 g, 5.2 mmol) was dissolved in ethyl acetate (4 ml), and 3-chloroperbenzoic acid (ca. 77%, 1.2 g, 5.2 mmol) was added thereto. The reaction mixture was stirred at room temperature for 14 hrs and subjected to a silica gel (50 g) column chromatography. The fractions eluted with ethyl acetate-ethanol (4:1, v/v) were collected and concentrated. The residue was dissolved in acetonitrile (10 ml), and trimethylsilyl cyanide (0.95 g, 9.6 mmol) and N,N-dimethylcarbamoyl chloride (0.77 g, 7.2 mmol) were added thereto. The reaction mixture was stirred at room temperature for 16 hrs and combined with ethyl acetate and water. The organic layer was 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-ethyl acetate (4:1, v/v) were collected and concentrated to give the titled compound (0.80 g, 76%).

Workup

  1. washThe fractions eluted with ethyl acetate-ethanol (4:1
  2. customv/v) were collected
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in acetonitrile (10 ml)
  5. stirringThe reaction mixture was stirred at room temperature for 16 hrs
  6. washThe organic layer was 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-ethyl acetate (4:1
  10. customv/v) were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-25258251359d4135a1ad391e3b6683d2
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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