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

HRID 1291271ノート

反応式

HRID 1291271 の反応式
[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

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 178424003HCID 178424003、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9016e0357b644b1f97896df44b913a0e
出典データセット
uspto-grants-1998_05
特許番号
US05753664

反応ノート

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