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

HRID 274723

반응식

HRID 274723 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][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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

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

출처 및 근거

ORD 기록
ord-4e5491567a1d47698ca87d7f0297994e
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389658

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