Sodium Hydroxide → 2-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

HRID 1291364ノート

反応式

HRID 1291364 の反応式
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[SH:14].[Si]([O: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(C)(C)C)(C)C.[OH-].[Na+]>CO>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[S:14][CH2:33][C:32]1[CH:31]=[CH:30][C:29]([C:27](=[O:28])[C:26]2[CH:37]=[CH:38][C:23]([OH:22])=[CH:24][CH:25]=2)=[CH:36][CH:35]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 18918912HCID 18918912、化合物HCID 178424003HCID 178424003、化合物

生成物 1

HCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone収率 69.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 3,5-dimethyl-2-mercapto-4(3H)-quinazolinone (952 mg), 4-(4-t-butyldimethylsilyloxybenzoyl)benzyl bromide (2.90 g) and 1N-aqueous sodium hydroxide solution (4.6 ml) in methanol (20 ml) was stirred at room temperature for 4 hours. This reaction mixture was concentrated and extracted with chloroform and the extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=19:1). The resulting 2-[4-(4-t-butyldimethylsilyloxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone was dissolved in tetrahydrofuran (15 ml). To this solution was added 1M tetrabutylammonium fluoride/tetrahydrofuran (3.8 ml), and the mixture was stirred at room temperature for 1 hour. This reaction mixture was diluted with water and the resulting precipitate was collected by filtration, rinsed with water, and dried to provide the title compound as colorless solid (1.332 g).

後処理

  1. concentrationThis reaction mixture was concentrated
  2. extractionextracted with chloroform
  3. washthe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=19:1)
  7. dissolutionThe resulting 2-[4-(4-t-butyldimethylsilyloxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone was dissolved in tetrahydrofuran (15 ml)
  8. additionTo this solution was added 1M tetrabutylammonium fluoride/tetrahydrofuran (3.8 ml)
  9. additionThis reaction mixture was diluted with water
  10. filtrationthe resulting precipitate was collected by filtration
  11. washrinsed with water
  12. customdried

出典と根拠

ORDレコード
ord-4ff04bb3bbe844b7a75b4b7400d549b2
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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