Methyl iodide → 4-(1-(N-acetyl-N-methylamino)cyclopropyl)anisole

HRID 481490노트

반응식

HRID 481490 반응식
[H-].[Na+].[C:3]([NH:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)(=[O:5])[CH3:4].I[CH3:19]>CN(C=O)C.[NH4+].[Cl-].O>[C:3]([N:6]([C:7]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:9][CH2:8]1)[CH3:19])(=[O:5])[CH3:4]

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 190664314-(1-(N-Acetylamino)cyclopropyl)anisole

생성물 1

HCID 190664974-(1-(N-acetyl-N-methylamino)cyclopropyl)anisole수율 73.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

실험 절차

To a stirred suspension of 60% sodium hydride (234 mg, 5.85 mmol) (washed with pentane) in dry DMF (20 ml) was added Compound 8 (1.00 g, 4.87 mmol) portionwise at room temperature. After 15 min., to this was added iodomethane (1.04 g, 7.31 mmol) at same temperature. The reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with sat. NH4Cl aq. (20 ml)-H2O (20 ml) and extracted with toluene-AcOEt (1:2). The combined solution was washed with water and brine, dried(MgSO4) and concentrated in vacuo to give crude product (1.05 g) as a yellow solid. The crude product was recrystallized from hexane-ethyl acetate to give Compound 9 (784 mg, 73%) as a white solid.

후처리

  1. extractionextracted with toluene-AcOEt (1:2)
  2. washThe combined solution was washed with water and brine, dried(MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give crude product (1.05 g) as a yellow solid
  5. customThe crude product was recrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-93e42b44c33b4d50a7f666f8061788fc
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789423

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