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

HRID 1874874Notes

Reaction equation

HRID 1874874 reaction equation
[C:1]([CH:3]([NH:13][C:14](=O)[CH2:15][CH2:16][CH3:17])[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:39]>C(#N)C>[Cl:39][C:1]1[N:2]=[C:14]([CH2:15][CH2:16][CH3:17])[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 594513703-Benzyloxy-a-(N-butyryl)-aminopropionitrile

Product 1

HCID 594513894-chloro-5-{[(phenylmethyl)oxy]methyl}-2-propyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}butanamide (1.60 g, 6.5 mmol), triphenylphosphine (4.3 g, 16.3 mmol), and carbon tetrachloride (1.6 mL, 16.3 mmol) in acetonitrile (65 mL) was heated at 42° C. for 12 h. The reaction was then concentrated and the residue was stirred in CH2Cl2 (70 mL) and 0.5 N NaOH (60 mL) for 15 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-40% EtOAc:hexanes) to give the title compound as a light yellow solid, in assumed quantitative yield due to inseparable triphenylphosphine oxide. 1H NMR (400 MHz, CDCl3) δ 7.30-7.40 (m, 5H), 4.52 (s, 4H), 2.58-2.68 (m, 2H), 1.68-1.82 (m, 2H), 0.97 (t, 3H).

Workup

  1. concentrationThe reaction was then 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 (5-40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-1a4f210af72d457085213dad455d377e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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