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

HRID 1874868ノート

反応式

HRID 1874868 の反応式
[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

参加物

5

反応物 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59451375N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}propanamide

生成物 1

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

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}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).

後処理

  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)

出典と根拠

ORDレコード
ord-12cf6e9dc7f347a6ba91c7196a7d8d8f
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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