Water → 1-(9-Octadecenyl)-3,7-dimethylxanthine

HRID 1870853

반응식

HRID 1870853 반응식
[H-].[Na+].[NH:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O>CS(C)=O>[CH2:17]([N:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

참가 물질

6

반응물 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 802021-Bromo-9-octadecene

생성물 1

HCID 537845551-(9-Octadecenyl)-3,7-dimethylxanthine수율 34.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

Sodium hydride (95%, 84 mg, 3.5 mmol) was added to a solution of theobromine (0.595 g, 3.2 mmol) in dimethylsulfoxide (15 ml). After 20 minutes of stirring, 1-bromo-9-octadecene (0.995 g, 3 mmol), prepared above, was added. After 6 hours of stirring at room temperature, the reaction mixture was warmed to 60° C. over 3 hours and then poured into a separatory funnel containing 50 ml of water. The reaction mixture was extracted with five 40 ml aliquots of dichloromethane. The organic extracts were combined, washed with water (50 ml) and brine (50 ml) and dried over anhydrous magnesium sulfate. Removing the solvent under reduced pressure resulted in a crude product further purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant, yielding 0.44 g of 1-(9-octadecenyl)-3,7-dimethylxanthine (34% yield).

후처리

  1. additionwas added
  2. stirringAfter 6 hours of stirring at room temperature
  3. additionpoured into a separatory funnel
  4. extractionThe reaction mixture was extracted with five 40 ml aliquots of dichloromethane
  5. washwashed with water (50 ml) and brine (50 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoving the solvent under reduced pressure
  8. customresulted in a crude product
  9. customfurther purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant

출처 및 근거

ORD 기록
ord-835f5f6191cb49a5aa6d5bc1f57a77ed
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100271

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