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

HRID 1874868노트

반응식

HRID 1874868 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-12cf6e9dc7f347a6ba91c7196a7d8d8f
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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