Dimethylhydantoin → 3-[4-(4-Pyridylthio)butyl]-5,5-dimethylhydantoin

HRID 6167

반응식

HRID 6167 반응식
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].Cl[CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C1CCN2C(=NCCC2)CC1.C(OCC)(=O)C>CN(C)C=O>[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[N:4]([CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:3]1=[O:8]

참가 물질

6

반응물 4

HCID 6491DimethylhydantoinHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 158169784-(4-Chlorobutylthio)pyridine

생성물 1

HCID 190790983-[4-(4-Pyridylthio)butyl]-5,5-dimethylhydantoin수율 56.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2.56 g (20 mmol) of 5,5-dimethylhydantoin and 4.03 g (20 mmol) of 4-(4-chlorobutylthio)pyridine in 20 ml of N,N-dimethylformamide, 3.00 ml (20 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at room temperature for 43 hours, followed by further stirring at 70° C. for 10 hours. Ethyl acetate was added to the reaction mixture, and the mixture was washed three times with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol =10:1) to give 3.33 g of the desired compound (56.8% yield, colorless crystals).

후처리

  1. stirringby further stirring at 70° C. for 10 hours
  2. washthe mixture was washed three times with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol =10:1)

출처 및 근거

ORD 기록
ord-223b53ba401c4783b307cafc7579f4f4
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246948

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