Dimethylformamide → Benzamide,4-fluoro-N-methoxy-N-methyl-3-(1-methylethoxy)-

HRID 238882

반응식

HRID 238882 반응식
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][C:3]=1[OH:14].[CH:15](I)([CH3:17])[CH3:16].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>C(Cl)Cl.O>[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][C:3]=1[O:14][CH:15]([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodide2회HCID 10796Cesium carbonateHCID 594590524-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide

생성물 1

HCID 59459043Benzamide,4-fluoro-N-methoxy-N-methyl-3-(1-methylethoxy)-수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

A 2 L round bottom flask equipped with a mechanical stirrer, a N2 inlet, a condenser and a temperature controller, was charged 4-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide (99.6 g, 0.5 mol), isopropyl iodide (110.5 g, 0.65 mol) and Cs2CO3 (195.5 g) and DMF (300 mL). The reaction mixture was heated at 50° C. for 3 h. Isopropyl iodide (17.0 g, 0.1 mol) was added and the reaction was heated at 50° C. for 12 h. The reaction mixture was allowed to cool to rt and water (1 L) and CH2Cl2 (500 mL) were added. The reaction mixture was stirred at rt for 0.5 h, and the organic phase was separated. The aqueous layer was extracted with CH2Cl2 (3×500 mL). The combined organic extracts were washed with water (2×1 L), brine (1 L), dried over MgSO4, filtered and concentrated in vacuo at 40° C. for 18 h to give 4-fluoro-3-isopropoxy-N-methoxy-N-methlbenzamide as an off-white solid (120.0 g, 100%).

후처리

  1. customA 2 L round bottom flask equipped with a mechanical stirrer, a N2 inlet, a condenser
  2. temperaturethe reaction was heated at 50° C. for 12 h
  3. temperatureto cool to rt
  4. customthe organic phase was separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (3×500 mL)
  6. washThe combined organic extracts were washed with water (2×1 L), brine (1 L)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo at 40° C. for 18 h

출처 및 근거

ORD 기록
ord-f5ebc7c24b174f80a0f49481552bd4ea
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642576B2

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