Carbon Tetrachloride → 4-chloro-2-ethyl-5-{[(phenylmethyl)oxy]methyl}-1H-imidazole

HRID 1874868Notes

Reaction equation

HRID 1874868 reaction equation
[C:1]([CH:3]([NH:13][C:14](=O)[CH2:15][CH3:16])[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:38]>C(#N)C>[Cl:38][C:1]1[N:2]=[C:14]([CH2:15][CH3:16])[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 59451375N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}propanamide

Product 1

HCID 594516374-chloro-2-ethyl-5-{[(phenylmethyl)oxy]methyl}-1H-imidazoleYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}propanamide (3.62 g, 15.6 mmol), triphenylphosphine (10.2 g, 39.0 mmol), and carbon tetrachloride (3.8 mL, 39.0 mmol) in acetonitrile (150 mL) was heated at 45° C. for 4.5 h. The reaction was concentrated and the residue was stirred in CH2Cl2 (170 mL) and 0.5 N NaOH (150 mL) for 15 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-50% EtOAc:hexanes) to give the title compound (2.51 g, 64%) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.29-7.38 (m, 5H), 4.52 (s, 2H), 4.50 (s, 2H), 2.65 (q, 2H), 1.26 (t, 3H). ES-LCMS: m/z 250.6, 252.9 (M+H).

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 (5-50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-12cf6e9dc7f347a6ba91c7196a7d8d8f
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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