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

HRID 1874874노트

반응식

HRID 1874874 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1a4f210af72d457085213dad455d377e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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