Tetrahydrofuran → 2-[4-(4-Fluorobenzoyl)benzylthio]-3,5-dimethyl-quinazolin-4-one

HRID 1291271노트

반응식

HRID 1291271 반응식
[SH:1][C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH3:14])[N:3]=1.C1COCC1.[OH-].[Na+].[F:22][C:23]1[CH:38]=[CH:37][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=2)=[O:28])=[CH:25][CH:24]=1>C(O)C.C(OCC)(=O)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33][S:1][C:2]3[N:11]([CH3:12])[C:10](=[O:13])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][C:8]=4[CH3:14])[N:3]=3)=[CH:31][CH:30]=2)=[O:28])=[CH:37][CH:38]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 178424003HCID 178424003, 화합물

생성물 1

HCID 189193452-[4-(4-Fluorobenzoyl)benzylthio]-3,5-dimethyl-quinazolin-4-one수율 72%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of 2-mercapto-3,5-dimethylquinazolin-4-one (0.492 g) as obtained in Reference Example 18-in ethanol (10.0 ml)-THF (10.0 ml) was added 1N-sodium hydroxide (2.50 ml). Then, 4-(4-fluorobenzoyl)benzyl bromide (0.700 g) was added and the mixture was stirred at 60° C. for 3.5 hours. This reaction mixture was diluted with ethyl acetate and washed with saturated aqueous NaCl solution and the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to provide the title compound as colorless needles (0.717 g, yield 72%). 1H-NMR (CDCl3) δ: 2.85(3H,s), 3.55(3H,s), 4.60(2H,s), 7.10-7.20(3H,m), 7.46-7.63(4H,m), 7.72-7.87(4H,m).

후처리

  1. washwashed with saturated aqueous NaCl solution
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-9016e0357b644b1f97896df44b913a0e
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

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