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

HRID 1874874ノート

反応式

HRID 1874874 の反応式
[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

参加物

5

反応物 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 594513703-Benzyloxy-a-(N-butyryl)-aminopropionitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1a4f210af72d457085213dad455d377e
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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