Carbon Tetrachloride → HCID 59451471, compound

HRID 1874863Notes

Reaction equation

HRID 1874863 reaction equation
[C:1]([CH:3]([NH:13][C:14](=O)[CH3:15])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:37]>C(#N)C>[Cl:37][C:1]1[N:2]=[C:14]([CH3:15])[NH:13][C:3]=1[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59451498HCID 59451498, compound

Product 1

HCID 59451471HCID 59451471, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}acetamide (1.64 g, 7.5 mmol), triphenylphosphine (4.9 g, 18.8 mmol), and carbon tetrachloride (1.8 mL, 18.8 mmol) in acetonitrile (75 mL) was heated at 45° C. for 6 h. The reaction was concentrated and the residue was stirred in CH2Cl2 (80 mL) and 0.5 N NaOH (70 mL) for 15 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-70% EtOAc:hexanes) to give the title compound as a yellow solid, in assumed quantitative yield due to inseparable triphenylphosphine oxide. 1H NMR (400 MHz, CDCl3) δ ppm 7.28-7.37 (m, 5H), 4.50 (s, 2H), 4.48 (s, 2H), 2.37 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. customThe organic layer was isolated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel flash column chromatography (5-70% EtOAc:hexanes)

Sources & evidence

ORD record
ord-364355bba100410c8b98fe8133bcdd01
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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