Water → 1-(11-Dodecenyl)-3,7-dimethylxanthine

HRID 964544노트

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HRID 964544 반응식
[NH:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3].[Na].CS([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])(=O)=O.O>CS(C)=O>[CH2:30]([N:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=[CH2:19]

참가 물질

5

반응물 3

HCID 962WaterHCID 2329589712-Methanesulfonyl-1-dodeceneHCID 66980828Theobromine sodium

생성물 1

HCID 232958711-(11-Dodecenyl)-3,7-dimethylxanthine수율 67%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
60 °C

실험 절차

To a solution of l1 -dodecen-1-ol (5.5 g, 29.9 mmol) in dichloromethane (70 ml) at 0° C. was added methanesulfonyl chloride (3.55 g, 2.40 ml, 31.0 mmol) followed by triethylamine (4.38 g, 46.0 mmol). After stirring for 10 minutes at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hours. The reaction was poured into water (60 ml), separated and washed with dichloromethane (50 ml). The organic portions were combined, dried with magnesium sulfate, and evaporated, yielding 12-methanesulfonyl-1-dodecene as a yellow oil which was used without further purification. To a suspension of sodium theobromine (6.00 g, 30.0 mmol) in dimethylsulfoxide (60 mL) was added 12-methanesulfonyl-1-dodecene. The resulting reaction mixture was stirred for 16 hours at 60° C. The mixture was then poured into water (120 ml) and extracted with diethyl ether (2×100 ml). The organic portions were combined, dried with magnesium sulfate. The evaporated solvent left a cream-colored solid. Recrystallization from ethyl acetate/hexane (1:1) yielded 6.97 g of a white solid, 1-(l1-dodecenyl)-3,7-dimethylxanthine as a white solid (67% yield).

후처리

  1. customwas used without further purification
  2. customThe resulting reaction mixture
  3. extractionextracted with diethyl ether (2×100 ml)
  4. dry with materialdried with magnesium sulfate
  5. waitThe evaporated solvent left a cream-colored solid
  6. customRecrystallization from ethyl acetate/hexane (1:1)

출처 및 근거

ORD 기록
ord-8228e720d2cc4ad1a384f59c88942300
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770595

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