Dimethyl Sulfoxide → 1-(6-Oxohexyl)-3,7-dimethylxanthine

HRID 1419779노트

반응식

HRID 1419779 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:27](=[O:28])[C:26]2[N:25]([CH3:29])[CH:24]=[N:23][C:22]=2[N:21]([CH3:30])[C:19]1=[O:20].C(N(CC)CC)C>C(Cl)Cl.O>[O:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:27](=[O:28])[C:26]2[N:25]([CH3:29])[CH:24]=[N:23][C:22]=2[N:21]([CH3:30])[C:19]1=[O:20]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 99256901-(6-Hydroxyhexyl)-3,7-dimethylxanthine

생성물 1

HCID 186910651-(6-Oxohexyl)-3,7-dimethylxanthine수율 87.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Dimethyl sulfoxide (156 mL, 172 mg, 2.2 mmol) was slowly added to a solution of oxalyl chloride (103 mL, 150 mg, 1.2 mmol) at -78° C. A solution of 1-(6-hydroxyhexyl)-3,7-dimethylxanthine (300 mg, 1.1 mmol) in methylene chloride (5 mL) was added, followed by 15 minutes of stirring. The cold bath was removed after addition of triethylamine (765 mL, 555 mg, 5.5 mmol). The reaction was added at room temperature to 20 mL water and extracted with methylene chloride (3×50 mL). The organic layers were combined and washed with 1% hydrogen chloride (20 mL), saturated sodium bicarbonate (20 mL), and brine (20 mL) and then dried over sodium sulfate. Evaporation of solvent and recrystallization of the residue in chloroform/petroleum ether yields 267 mg 1-(6-oxohexyl)-3,7-dimethylxanthine (87% yield).

후처리

  1. customThe cold bath was removed
  2. extractionextracted with methylene chloride (3×50 mL)
  3. washwashed with 1% hydrogen chloride (20 mL), saturated sodium bicarbonate (20 mL), and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of solvent and recrystallization of the residue in chloroform/petroleum ether

출처 및 근거

ORD 기록
ord-f6023ad29a5a40d8b9a8c2773a2e8b3a
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05889011

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