Dimethylformamide → HCID 69901210, 화합물

HRID 1884219노트

반응식

HRID 1884219 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:25])[C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:16][OH:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].CN(C)C=O.Br[CH2:34][F:35]>O.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:25])[C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:16][O:17][CH2:34][F:35])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 61108BromofluoromethaneHCID 69898186HCID 69898186, 화합물

생성물 1

HCID 69901210HCID 69901210, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
-5 °C

실험 절차

Two hundred milligrams (200 mg) of N-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-2-(4-methylphenyl)acrylamide (0.586 mmol), 28 mg (0.70 mmol) of 60% sodium hydride, 2 ml of anhydrous N,N-dimethylformamide and 1 ml of anhydrous diethyl ether were mixed and 0.5 ml of bromofluoromethane was added thereto at −5° C. The mixture was stirred at −5° C. for 30 minutes and then stirred at 0° C. for 1 hour. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with 5% hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated brine subsequently, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel preparative thin layer chromatography (eluent, hexane:ethyl acetate=2:1) to give 205 mg of N-[2-(3,4-dimethoxyphenyl)ethyl]-3-fluoromethoxy-2-(4-methylphenyl)acrylamide (the present compound 1-4).

후처리

  1. customat −5° C
  2. stirringstirred at 0° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 5% hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated brine subsequently
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7edc828b53cb49e7b8695ab3d0125b4f
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06762321B2

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