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

HRID 864020

反応式

HRID 864020 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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 g of the desired product was obtained (10.4% yield, yellow oil).

後処理

  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)

出典と根拠

ORDレコード
ord-23d280a50411417ca88c8e86ccf73a33
出典データセット
uspto-grants-1996_10
特許番号
US05561147

関連ノート

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