Dimethylcarbamoyl Chloride → tert-Butyl 6-cyano-2-pyridylmethylcarbamate

HRID 499466Notes

Reaction equation

HRID 499466 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH+:8]([O-])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].C[Si]([C:21]#[N:22])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:21]([C:6]1[N:1]=[C:2]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=[CH:4][CH:5]=1)#[N:22]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86596464tert-Butyl 2-pyridylmethylcarbamate N-oxide

Product 1

HCID 22939432tert-Butyl 6-cyano-2-pyridylmethylcarbamateYield 58%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

tert-Butyl 2-pyridylmethylcarbamate N-oxide (3.0 g, 13.3 mmol) was dissolved in nitroethane (50 ml), and trimethylsilyl cyanide (2.8 g, 28.6 mmol) and N,N-dimethylcarbamoyl chloride (1.7 g, 16.2 mmol) were added thereto. The mixture was stirred at room temperature for 24 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (2:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (1.8 g, 58%) as white crystals.

Workup

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

Sources & evidence

ORD record
ord-9af0a5c6301c483e8ec9e9e51c2b3bb3
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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