Dimethylcarbamoyl Chloride → HCID 22939273, compound

HRID 499485Notes

Reaction equation

HRID 499485 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH+:9]([O-])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:3][CH:2]=1.C[Si]([C:22]#[N:23])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:22]([C:2]1[CH:3]=[C:4]([CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][N:1]=1)#[N:23]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86628983HCID 86628983, compound

Product 1

HCID 22939273HCID 22939273, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

tert-Butyl 2-(4-pyridyl)ethylcarbamate N-oxide (7.4 g, 31 mmol) was dissolved in nitroethane (100 ml), and trimethylsilyl cyanide (9.2 g, 92 mmol) and N,N-dimethylcarbamoyl chloride (6.7 g, 62 mmol) were added thereto. The mixture was stirred at room temperature for 10 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (1:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (6.6 g, 86%).

Workup

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

Sources & evidence

ORD record
ord-6d4d6f11176f4f49bacf9fe6374d5f5b
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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