Methyl iodide → 2-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide

HRID 1841639노트

반응식

HRID 1841639 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:26])[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:30]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:26][CH3:30])[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11474256Cga-380778

생성물 1

HCID 111883752-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(4-Chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (2.6 g, 7.0 mmol) is dissolved in N,N-dimethylformamide (30 ml). Sodium hydride (0.18 g, 7.5 mmol) is added in portions at +5° C. The mixture is stirred for 30 minutes at room temperature. Subsequently iodomethane (1.1 g, 7.5 mmol) is added dropwise and the resulting mixture is stirred for further 3 hours at room temperature. The reaction mixture is poured on ice/water (200 ml) and extracted with ethyl acetate (2×200 ml). The combined organic layer is washed with brine (200 ml) and dried over magnesium sulfate. After evaporation of the solvent, the residue is purified by chromatography (ethyl acetate/hexane) to yield 2-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide. 1H-NMR (300 MHz, CDCl3): 2.53 (t, 1H, C≡CH), 2.80 (t, 2H, CH2CH2), 3.34 (s, 3H, OCH3), 3.55 (t, 2H, CH2CH2), 3.84 (s, 3H, OCH3), 4.58 (s, 1H, CHOH), 4.79 (m, 2H, OCH2), 6.68-7.34 (m, 8H, CH arom., NH).

후처리

  1. stirringthe resulting mixture is stirred for further 3 hours at room temperature
  2. additionThe reaction mixture is poured on ice/water (200 ml)
  3. extractionextracted with ethyl acetate (2×200 ml)
  4. washThe combined organic layer is washed with brine (200 ml)
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue is purified by chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-763e605affde4167876d10832a10edb0
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683211B1

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