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

HRID 964155

反応式

HRID 964155 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][CH2:17][S:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.[CH2:25]1[CH2:35][CH2:34][N:33]2C(=NC[CH2:31][CH2:32]2)CC1.O>CN(C)C=O>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:18][CH2:17][CH2:16][CH2:15][CH2:14][N:12]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7](=[O:8])[N:9]([CH2:14][CH2:15][CH2:16][CH2:17][S:18][C:32]2[CH:31]=[CH:25][CH:35]=[CH:34][N:33]=2)[C:10]1=[O:11]

参加物

6

反応物 4

HCID 962WaterHCID 64048QuinazolinedioneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 190791862-(4-Chlorobutylthio)pyridine

生成物 1

HCID 190792321,3-bis[4-(2-pyridylthio)butyl]quinazoline-2,4(1H,3H)-dione収率 9%

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 2.02 g (10 mmol) of 2-(4-chlorobutylthio)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: hexane/ethyl acetate=2:1 to 1:2). First, 221 mg of the desired product was obtained (4.6% yield, yellow oil), and then, 292 mg of 3-[4-(2-pyridylthio)butyl]quinazoline-2,4(1H,3H)-dione was obtained (8.9% yield, white crystals).

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: hexane/ethyl acetate=2:1 to 1:2)

出典と根拠

ORDレコード
ord-65d00281e8b841259304b18007498ff0
出典データセット
uspto-grants-1998_06
特許番号
US05767121

関連ノート

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