Water → 3-[3-(4-pyridylthio)propyl]quinazoline-2,4(1H,3H)-dione

HRID 274722

반응식

HRID 274722 반응식
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=[O:11])=[O:8].Cl[CH2:14][CH2:15][CH2:16][S:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[N:21]1[CH:22]=[CH:23][C:18]([S:17][CH2:16][CH2:15][CH2:14][N:9]2[C:7](=[O:8])[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[NH:12][C:10]2=[O:11])=[CH:19][CH:20]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 64048QuinazolinedioneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 158169844-[(3-Chloropropyl)sulfanyl]pyridine

생성물 1

HCID 190790923-[3-(4-pyridylthio)propyl]quinazoline-2,4(1H,3H)-dione수율 31.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of 1.62 g (10 mmol) of benzoylene urea and 1.88 g (10 mmol) of 4-(3-chloropropylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/ethanol=25:1 to 10:1 to 2:1). First, 0.973 g of 3-[3-(4-pyridylthio)propyl]quinazoline-2,4-(1H,3H)-dione (31.1% yield, pale yellow crystals) was obtained, and then, 0.487 of the desired product was obtained (10.4% yield, yellow oil).

후처리

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=25:1 to 10:1 to 2:1)

출처 및 근거

ORD 기록
ord-c1a66e78774b4757adf3b1f2bf316a4b
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389658

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