Dimethylcarbamoyl Chloride → tert-butyl N-[2-(6-cyanopyridin-2-yl)ethyl]carbamate

HRID 499484Notes

Reaction equation

HRID 499484 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH+:9]([O-])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].C[Si]([C:22]#[N:23])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:22]([C:6]1[N:1]=[C:2]([CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=[CH:4][CH:5]=1)#[N:23]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86628981tert-Butyl 2-(2-pyridyl)ethylcarbamate N-oxide

Product 1

HCID 22939284tert-butyl N-[2-(6-cyanopyridin-2-yl)ethyl]carbamateYield 83%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

tert-Butyl 2-(2-pyridyl)ethylcarbamate N-oxide (6.2 g, 26 mmol) was dissolved in nitroethane (80 ml), and trimethylsilyl cyanide (7.8 g, 78 mmol) and N,N-dimethylcarbamoyl chloride (5.5 g, 51 mmol) were added thereto. The mixture was stirred at room temperature for 48 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (1:2, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (5.3 g, 83%).

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with ethyl acetate-hexane (1:2
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ab06ac3ba76b4d23bb83fe04094f3194
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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