Dimethylcarbamoyl Chloride → 3-(Azidomethyl)-6-methyl-2-pyridinecarbonitrile

HRID 1295987Notes

Reaction equation

HRID 1295987 reaction equation
C[Si]([C:5]#[N:6])(C)C.CN(C)C(Cl)=O.[N:13]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH3:24])=[N+:21]([O-])[CH:22]=1)=[N+:14]=[N-:15].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:13]([CH2:16][C:17]1[C:22]([C:5]#[N:6])=[N:21][C:20]([CH3:24])=[CH:19][CH:18]=1)=[N+:14]=[N-:15]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 22929836HCID 22929836, compound

Product 1

HCID 229298063-(Azidomethyl)-6-methyl-2-pyridinecarbonitrileYield 77.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trimethylsilyl cyanide (6.4 ml, 48 mmol) and dimethylcarbamyl chloride (4.2 ml, 46 mmol) were added in that order to a solution of the 5-(azidomethyl)-2-methyl-1-pyridiniumolate (7.08 g, 43.2 mmol) in methylene chloride (80 ml) at room temperature and the mixture was stirred at the same temperature for 23 hours. After confirming completion of the reaction by thin layer chromatography, saturated aqueous sodium hydrogencarbonate (80 ml) was added and the mixture was stirred for 10 minutes. The reaction mixture was diluted with ethyl acetate, the aqueous layer was separated and extraction was performed with ethyl acetate. The collected organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (5.79 g, 56%, two steps) as a colorless oil.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 10 minutes
  3. customthe aqueous layer was separated
  4. extractionextraction
  5. washThe collected organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-10e015eea24c4a74b5f0c1ecba813f20
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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